Ascaloside microparticle composition and method for use

Abstract

This disclosure provides an ascaloside microparticle composition that can be used to form an ascaloside solution. In one embodiment, the ascaloside microparticle composition comprises one or more ascalosides and a microparticle carrier composition. The ascaloside microparticle composition can be dissolved in water and used to treat plants and crops. This disclosure provides a soluble solid ascaloside composition that is convenient for growers to use but is not plagued by the inherent inefficiencies of the above-mentioned diluted liquid formulations. The provided soluble solid formulation is compatible with ascaloside, has a long shelf life, good handling properties, dissolves rapidly and completely in water, is compatible with other pesticides, and is biocompatible (e.g., non-toxic to plants, humans, or the environment).

Description

[Technical Field]

[0001] Cross-reference of related applications This application claims priority to U.S. Provisional Application No. 63 / 519,978, filed on 16 August 2023, which is incorporated herein by reference in its entirety.

[0002] This invention relates to solid ascaoside compositions and methods for using solid ascaoside compositions. [Background technology]

[0003] Ascalosides are natural products of secondary metabolites produced by nematodes. Numerous, structurally diverse ascalosides have been identified in nature, and the molecules are thought to function as an evolutionarily conserved chemical language that nematodes use to control many aspects of their development. Ascalosides are also perceived by other organisms and have been shown to have various effects on a wide range of organisms, including bacteria, fungi, plants, and mammals, including humans. Ascalosides have potential as products for human pharmaceuticals, pesticides, and other diverse and valuable applications.

[0004] Ascaloside treatments, when applied to plants, have been shown to be effective in increasing plant resistance to certain pathogens and / or in inducing and priming plant defense responses (which can inhibit pathogen growth and / or parasitism). By activating and / or priming the plant's innate defenses, ascaloside can prevent pathogen proliferation and / or protect crops from harmful effects caused by a variety of pathogens.

[0005] A distinctive characteristic of ascalosides is their high potency. Plants respond to very low concentrations of ascaloside, resulting in a very low effective application ratio required to prime plant defenses. This, in turn, presents challenges for growers and supply chain logistics. This invention provides solutions to these challenges and related problems. [Overview of the project]

[0006] The inventors have found that the concentration of ascaloside in foliar sprays required to prime or induce a plant defense response can be as low as 10 nanomoles. This corresponds to ascaloside concentrations in applied foliar sprays that are orders of magnitude lower than one billionth of a percent. In addition, the inventors have found that foliar application of ascaloside at concentrations too high to crops can lead to a reduction in their beneficial effects. Therefore, there is a great need for practical yet accurate methods for applying these products at low concentrations. Using pure ascaloside to achieve suitably low application ratios requires dissolving very small amounts of ascaloside (in some cases as few milligrams) in a tank holding several hundred liters of water. This type of measurement and mixing is typically impractical for growers due to a lack of the necessary equipment to accurately measure and handle such small amounts. Furthermore, it can be difficult to completely and homogeneously dissolve small amounts of solid ascaloside in large quantities of water, and ascaloside in its pure form is solid and can also be in the form of a fine powder. Such powdered ascaloside may not dissolve immediately when added to water, and may also tend to float on the surface of the water and / or adhere to the edges of the container. These factors may lead to incomplete dissolution and / or inconsistent application ratios.

[0007] One solution to this problem is the use of pre-formulated liquid concentrates of ascaloside, which can be conveniently measured and mixed in agricultural spray tanks. Many pesticides are supplied as liquid concentrates and are typically formulated for growers to use about 1 / 2 fluid ounce to about 16 fluid ounces (most typically about 1 oz to about 4 oz per acre) of the crop being treated. Before field application, the appropriate amount of concentrate for the number of acres to be treated is diluted in a suitable amount of water (typically in a large spray tank) to produce a spray solution that is applied to the crop at a ratio that ensures good foliage coverage (typically about 10 to 20 gallons per acre for row crops).

[0008] The inventors determined that certain ascaloside foliar spray treatments are remarkably effective when applied to field crops by foliar spray at very low application rates (5 mg to 100 mg / acre), and have developed a prototype liquid concentrate formulation of ascaloside that can be conveniently applied by growers using familiar methods to achieve these application rates. While such formulations are easy to use and function well, they are unfortunately very inefficient from a logistical standpoint. For example, a prototype ascaloside concentrate was manufactured to enable convenient application of ascaloside at rates of approximately 25 to 100 mg / acre. The prototype is designed so that an application of 2 fluid ounces per acre delivers 25 mg of ascaloside per acre. Although this formulation is technically a concentrate, the solution is still very diluted compared to typical pesticides and contains less than 0.05% by weight of ascaloside. Distribution of such a product is inefficient because it requires the transport and storage of large amounts of water.

[0009] This disclosure provides a soluble solid ascaloside composition that is convenient for growers to use but is not plagued by the inherent inefficiencies of the above-mentioned diluted liquid formulations. The provided soluble solid formulation is compatible with ascaloside, has a long shelf life, good handling properties, dissolves rapidly and completely in water, is compatible with other pesticides, and is biocompatible (e.g., non-toxic to plants, humans, or the environment).

[0010] In one embodiment, a soluble solid ascaloside composition is provided that can be dissolved to conveniently produce a liquid ascaloside concentrate suitable for further dilution and application to crops. In one embodiment, the provided ascaloside composition comprises one or more ascalosides and a soluble solid carrier composition, wherein the ascaloside comprises one or more ascalosides in an amount of 20% by weight or less. In some embodiments, the ascaloside composition comprises one or more ascalosides in an amount of about 1% by weight to about 20% by weight.

[0011] In another embodiment, a soluble solid ascaloside composition is provided that can be dissolved to conveniently produce a spray-ready formulation suitable for application to plants. In one embodiment, the provided composition comprises one or more ascalosides and a soluble solid carrier composition, wherein the ascaloside composition contains one or more ascalosides in an amount of about 0.2% by weight or less. In some embodiments, the ascaloside composition contains one or more ascalosides in an amount of about 0.005% by weight to about 0.2% by weight.

[0012] The provided solid ascaloside composition can be dissolved in water and used to treat plants and crops. In some embodiments, the dissolution of the solid ascaloside composition provides a concentrated solution that is further diluted before use. [Modes for carrying out the invention]

[0013] The present disclosure provides solid ascaroside compositions comprising one or more ascarosides and a solid carrier composition, and methods of use. In some embodiments, the solid particulate composition comprises less than 20% by weight of one or more ascarosides. In other embodiments, the composition comprises less than 0.01% by weight of one or more ascarosides. As used herein, the term "ascaroside" includes ascarosides, derivatives or analogs of ascarosides, or combinations thereof, as described in further detail herein.

[0014] Ascaroside Ascarosides are secondary metabolites produced by nematodes. Many structurally diverse ascarosides have been identified in nature and are thought to function as an evolutionarily conserved chemical language that nematodes use to control many aspects of their development.

[0015] Ascarosides are derivatives of the sugar ascarylose, a dideoxy sugar that lacks hydroxyl groups at the 3 and 6 positions. The ascaroside has the formula I:

Chemical Formula

[0016] In a particular embodiment, Z is (i)-CH(CH3)-R 1 (R 1 This is C, which has been replaced by an optional substitution. 1-40 (It is an aliphatic group.) (ii)-CH(CH3)-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other askaloside molecules, or linkage via a carbon-containing linker moiety), (iii)-CH(CH3)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other askaloside molecules, or linkage via a carbon-containing linker moiety), (iv)-CH(CH3)-(CH2) n -CH(OH)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other askaloside molecules, or linkage via a carbon-containing linker moiety), (v)-CH(CH3)-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other askaloside molecules, or linkage via a carbon-containing linker moiety), (vi)-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other askaloside molecules, or linkage via a carbon-containing linker moiety), (vii)-(CH2) n -CH=CH-CO2R2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other askaloside molecules, or linkage via a carbon-containing linker moiety), (viii)-(CH2) n -CH(OH)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted. 1-20 Aliphatic group, optionally substituted C 1-20 This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety, or (ix)-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 This includes a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another askaloside molecule via a carbon-containing linker moiety.

[0017] In a particular embodiment, Z is (x)-CH(CH3)-(CH2) n -CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20(This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xi)-CH(CH3)-(CH2) n -CH=CH-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xii)-CH(CH3)-(CH2) n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xiii)-CH(CH3)-(CH2) n -C(O)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xiv)-(CH2) n -CON(R 3)2 (n is an integer of 1 to 40, and each R 3 is independently -H, optionally substituted C 1-20 aliphatic group, optionally substituted C 1-20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or a bond to another ascaroside molecule or linking via a carbon-containing linker moiety), (xv) -(CH2) n -CH=CH-CON(R 3 )2 (n is an integer of 1 to 40, and each R 3 is independently -H, optionally substituted C 1-20 aliphatic group, optionally substituted C 1-20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or a bond to another ascaroside molecule or linking via a carbon-containing linker moiety), (xvi) -(CH2) n -CH(OH)-CH2-CON(R 3 )2 (n is an integer of 1 to 40, and each R 3 is independently -H, optionally substituted C 1-20 aliphatic group, optionally substituted C 1-20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or a bond to another ascaroside molecule or linking via a carbon-containing linker moiety), (xvii) -(CH2) n -C(O)-CH2-CON(R 3 )2 (n is an integer of 1 to 40, and each R 3 is independently -H, optionally substituted C 1-20 aliphatic group, optionally substituted C 1-20This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety, or (xviii) A optionally unsaturated and optionally substituted carbon chain that terminates at a chain end containing a nitrogen-containing functional group, an oxygen-containing functional group, or a sulfur-containing functional group. 2-40 It is a side chain.

[0018] As defined above and described herein, in some embodiments, Z includes a nitrogen-containing functional group, an oxygen-containing functional group, or a sulfur-containing functional group. It will be understood that “oxygen-containing functional group” means a moiety containing one or more oxygen atoms (e.g., carbonyl-containing groups such as esters, aldehydes, carboxylic acids, orthoesters, and ketones; ethers, hydroxyls, and heterocycles containing one or more oxygen atoms and / or one of the aforementioned functional groups); “nitrogen-containing functional group” means a moiety 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” means a moiety containing one or more sulfur atoms (e.g., thioethers, sulfones, sulfonic acids, sulfoxides, thiols, thiocyanates, or disulfides).

[0019] In some embodiments, Z is optionally unsaturated and optionally substituted C, which terminates at a chain end containing an oxygen-containing functional group. 2-40 It is a side chain. In certain embodiments, Z is optionally unsaturated and optionally substituted with a chain terminus containing a carboxylic acid. 2-40 It is a side chain. In certain embodiments, Z is optionally unsaturated and optionally substituted with C, which terminates at the chain end containing an aldehyde. 2-40 It is a side chain. In certain embodiments, Z is optionally unsaturated and optionally substituted with C, which terminates at the chain end containing an ester. 2-40It is a side chain. In some embodiments, Z-CO2R 2 A chain terminator that terminates with a C, which is optionally unsaturated and optionally substituted. 2-40 Side chain. In some embodiments, Z is optionally unsaturated and optionally substituted with C, ending at a chain end containing -CO2H. 2-40 It is a side chain. In some embodiments, Z is optionally unsaturated and optionally substituted with C, which terminates at a chain end containing -CO2CH3. 2-40 It is a side chain. In some embodiments, Z is -CON(R 3 ) terminates at the end of the chain containing 2, optionally unsaturated and optionally substituted C 2-40 It is a side chain. In some embodiments, Z is -N(R 3 ) terminates at the end of the chain containing 2, optionally unsaturated and optionally substituted C 2-40 It is a side chain. In some embodiments, Z is optionally unsaturated and optionally substituted with C, which terminates at a chain end containing an ester containing a linker moiety covalently bonded to one or more additional askaloside molecules. 2-40 It is a side chain.

[0020] As described above, the ascarilose sugar portion in the provided compound can be substituted or unsubstituted (i.e., functional groups other than -OH may be present at the 2nd and 4th positions of the sugar, or in other words, in any of the formulas herein, the variable R a and / or R b (This can be anything other than -H).

[0021] As defined above and as described herein, R a and R b Each of these is independently -H or C 1-20 aliphatic, C 1-20 Ashiru, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bond functional group, sulfur bond functional group, silicon bond functional group, C 2-20 Carbonate (e.g., partial C(O)OR) c ), C 2-20Carbamates (e.g., partial-C(O)N(R) c )2), C 2-20 Thioesters (e.g., partial-C(S)R) c ), C 2-20 Thiocarbonates (e.g., partial-C(S)OR c ), C 2-20 Dithiocarbonates (e.g., partial-C(S)SR) c ), C 1-20 Thiocarbamates (e.g., partial-C(S)N(R) c )2) A portion that is optionally substituted from the group consisting of a sugar portion, a peptide, a polymer chain, or a linkage to an ascaloside molecule or a carbon-containing linker portion.

[0022] In a particular embodiment, R a is -H. In a particular embodiment, R b is -H. In a particular embodiment, R a and R b They are the same. In a particular embodiment, R a and R b Both are -H. In a particular embodiment, R a and R b They are different. In a particular embodiment, R a is -H, and R b is anything other than -H. In a particular embodiment, R a is anything other than -H, and R b is -H. In a particular embodiment, R a is -H, and R b is a p-hydroxybenzoate. In certain embodiments, R a is -H, and R b R is indole-3-carboxylate. In certain embodiments, R a is -H, and R b is (E)-2-methyl-2-butenoate. In certain embodiments, R a is -H, and R b is picolinate. In a particular embodiment, R ais -H, and R b is nicotinate. In a particular embodiment, R a is -H, and R b is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, R a is -H, and R b R is 4-((4-hydroxyphenylethyl)amino)-4-oxobutanoate. In certain embodiments, R a This includes glycosides, amino acids, peptides, or nucleotides. In certain embodiments, R b This includes glycosides, amino acids, peptides, or nucleotides. In certain embodiments, R a This includes linking to a second ascaloside molecule. In certain embodiments, R b This includes linking to an askaloside molecule. In certain embodiments, R a It contains sugar. In a particular embodiment, R b It contains sugar.

[0023] In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-20 It is aliphatic. In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-6 It is aliphatic. In some embodiments, R a C 1-20 It is aliphatic. In some embodiments, R a C 1-6 It is aliphatic. In some embodiments, R a R is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or t-butyl. In some embodiments, R a C 1-20 In some embodiments, R a is -C(O)R c In some embodiments, R a is -C(O)H. In some embodiments, R ais -C(O)CH3. In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-20 It is heteroaliphatic. In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-6 It is heteroaliphatic. In some embodiments, R a C 1-20 It is heteroaliphatic. In some embodiments, R a C 1-6 It is heteroaliphatic. In some embodiments, R a R is an optionally substituted 3-membered and 8-membered saturated or partially unsaturated heterocycline having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R a R is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocycline having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R a R is an aryl that has been optionally replaced. In some embodiments, R a R is a phenyl compound that is optionally substituted. In some embodiments, R a R is phenyl. In some embodiments, R a R is an optionally substituted heteroaryl group. In some embodiments, R a R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R a R is an optionally substituted 8-12 member heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R a This is C, which has been replaced by an optional substitution. 2-20 It is a carbonate. In some embodiments, R a is -C(O)OR c In some embodiments, R a This is C, which has been replaced by an optional substitution. 2-20It is a carbamate. In some embodiments, R a is -C(O)N(R c )2. In some embodiments, R a This is C, which has been replaced by an optional substitution. 2-20 It is a thioester. In some embodiments, R a is -C(S)R c In some embodiments, R a This is C, which has been replaced by an optional substitution. 2-20 It is a thiocarbonate. In some embodiments, R a is -C(S)OR c In some embodiments, R a This is C, which has been replaced by an optional substitution. 2-20 It is a dithiocarbonate. In some embodiments, R a is -C(S)SR c In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-20 It is a thiocarbamate. In some embodiments, R a is -C(S)N(R c )2.

[0024] In some embodiments, R a This is an optionally substituted hydroxyl protecting group. Suitable hydroxyl protecting groups are well known in the art, as seen in Protecting Groups in Organic Synthesis, TW Greene and PGMWuts, 3 rdThis includes those described in detail in edition, John Wiley & Sons, 1999. Examples of suitable oxygen protecting groups include, but are not limited to, acetyl, benzoyl benzyl, β-methoxyethoxymethyl ether (MEM), dimethoxytrityl (DMT), methoxymethyl ether (MOM), methoxytrityl (MMT), p-methoxybenzyl ether (PMB), methylthiomethyl ether, pivaloyl, tetrahydropyranyl (THP), tetrahydrofuran (THF), trityl, silyl ethers (e.g., trimethylsilyl (TMS), tert-butyldimethylsilyl (TBDMS), triisopropylsilyloxymethyl (TOM), and triisopropylsilyl (TIPS) ethers), methyl ethers, and ethoxyethyl ethers. In some embodiments, R a is -OR c That is the case.

[0025] In some embodiments, R a R is an optionally substituted phosphorus-bonded functional group. As used herein, “phosphorus-bonded functional group” will be understood to refer to a moiety containing one or more phosphorus atoms (e.g., phosphine, phosphodiester, phosphonic acid, phosphoric acid). In some embodiments, R a R is an optionally substituted sulfur-bonded functional group. As used herein, “sulfur-bonded functional group” will be understood to refer 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 This is a silicon-bonded functional group that has been optionally substituted. As used herein, “silicon-bonded functional group” will be understood to refer to a moiety containing one or more silicon atoms (e.g., silanol, thuroxide, siloxane, silyl ether, silyl chloride, silyl hydrogenate, silene, or silole).

[0026] In some embodiments, R a R is an optionally substituted sugar moiety. In some embodiments, R ais a peptide that has been optionally substituted. In some embodiments, R a R is a polymer chain that has been optionally substituted. In some embodiments, R a This is a bond to the askaloside molecule or a linkage via a carbon-containing linker moiety. In some embodiments, R a This includes ascaloside, and optionally substituted C 1-6 It is aliphatic or heteroaliphatic.

[0027] In some embodiments, R b This is C, which has been replaced by an optional substitution. 1-20 It is aliphatic. In some embodiments, R b This is C, which has been replaced by an optional substitution. 1-6 It is aliphatic. In some embodiments, R b C 1-20 It is aliphatic. In some embodiments, R b C 1-6 It is aliphatic. In some embodiments, R b R is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or t-butyl. In some embodiments, R b C 1-20 In some embodiments, R b is -C(O)R c In some embodiments, R b is -C(O)H. In some embodiments, R b is -C(O)CH3. In some embodiments, R b This is C, which has been replaced by an optional substitution. 1-20 It is heteroaliphatic. In some embodiments, R b This is C, which has been replaced by an optional substitution. 1-6 It is heteroaliphatic. In some embodiments, R b C 1-20 It is heteroaliphatic. In some embodiments, R b C 1-6 It is heteroaliphatic. In some embodiments, R bR is an optionally substituted 3-membered and 8-membered saturated or partially unsaturated heterocycline having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R b R is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocycline having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R b R is an aryl that has been optionally replaced. In some embodiments, R b R is a phenyl compound that is optionally substituted. In some embodiments, R b R is phenyl. In some embodiments, R b R is an optionally substituted heteroaryl group. In some embodiments, R b R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R b R is an optionally substituted 8-12 member heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R b This is C, which has been replaced by an optional substitution. 2-20 It is a carbonate. In some embodiments, R b is -C(O)OR c In some embodiments, R b This is C, which has been replaced by an optional substitution. 2-20 It is a carbamate. In some embodiments, R b is -C(O)N(R c )2. In some embodiments, R b This is C, which has been replaced by an optional substitution. 2-20 It is a thioester. In some embodiments, R b is -C(S)R c In some embodiments, R b This is C, which has been replaced by an optional substitution. 2-20 It is a thiocarbonate. In some embodiments, R b is -C(S)ORc In some embodiments, R b This is C, which has been replaced by an optional substitution. 2-20 It is a dithiocarbonate. In some embodiments, R b is -C(S)SR c In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-20 It is a thiocarbamate. In some embodiments, R b is -C(S)N(R c )2.

[0028] In some embodiments, R b R is an optionally substituted hydroxyl protecting group. In some embodiments, R b is -OR c That is the case.

[0029] In some embodiments, R b R is an optionally substituted phosphorus-bonded functional group. In some embodiments, R b R is an optionally substituted sulfur-bonded functional group. In some embodiments, R b This is a silicon-bonded functional group that has been optionally substituted.

[0030] In some embodiments, R b R is an optionally substituted sugar moiety. In some embodiments, R a is a peptide that has been optionally substituted. In some embodiments, R b R is a polymer chain that has been optionally substituted. In some embodiments, R b This is a bond to the askaloside molecule or a linkage via a carbon-containing linker moiety. In some embodiments, R b This includes ascaloside, and optionally substituted C 1-6 It is aliphatic or heteroaliphatic.

[0031] In some embodiments, R a and R bTogether, they can form an optionally substituted ring that optionally contains one or more heteroatoms and optionally contains one or more unsaturated sites. In some embodiments, R a and R b Together, they can form optionally substituted 3-12 membered monocyclic or bicyclic saturated or partially unsaturated carbocyclyl or heterocyclyl rings having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R a and R b These can combine to form optionally substituted 5-12 membered monocyclic or bicyclic aryl or heteroaryl rings having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0032] In a particular embodiment, R a , is -H, R b is a p-hydroxybenzoate. In certain embodiments, R a is -H, and R b R is indole-3-carboxylate. In certain embodiments, R a is -H, and R b is (E)-2-methyl-2-butenoate. In certain embodiments, R a is -H, and R b is picolinate. In a particular embodiment, R a is -H, and R b is nicotinate. In a particular embodiment, R a is -H, and R b is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, R a is -H, and R b It is 4-((4-hydroxyphenylethyl)amino)-4-oxobutanoate.

[0033] In a particular embodiment, R a and R bBoth are -H, and Z is selected from the formulas defined in (i) to (ix) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (i) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (ii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (iii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (iv) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (v) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (vi) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (vii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (viii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (ix) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (x) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xi) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xiii) above. In a particular embodiment, Ra and R b Both are -H, and Z conforms to equation (xiv) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xv) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xvi) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xvii) above.

[0034] As defined above and described herein, each R c In each occurrence, independently, -H is replaced by C of any choice. 1-12 Aliphatic, C substituted by choice 1-12 The linkage can be selected from heteroaliphatic molecules, optionally substituted aryl molecules, optionally substituted heteroaryl molecules, polymer chains, or linkage to another ascaloside molecule via a carbon-containing linker moiety.

[0035] In some embodiments, R c In each occurrence, independently, -H is replaced by C of any choice. 1-12 Aliphatic, C substituted by choice 1-12 The selection is made from heteroaliphatic compounds, optionally substituted aryl compounds, and optionally substituted heteroaryl compounds.

[0036] In some embodiments, R c The appearance of is -H. In some embodiments, R c This is C, which has been replaced by an optional substitution. 1-12 It is an aliphatic group. In some embodiments, R c This is C, which has been replaced by an optional substitution. 1-6 It is an aliphatic group. In some embodiments, R c This is C, which has been replaced by an optional substitution. 1-12 It is a heteroaliphatic group. In some embodiments, R c This is C, which has been replaced by an optional substitution.1-6 It is a heteroaliphatic group. In some embodiments, R c R is an optionally substituted 3-membered and 8-membered saturated or partially unsaturated heterocycline having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R c R is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocycline having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R c R is an optionally substituted aryl group. In some embodiments, R c R is a phenyl compound that is optionally substituted. In some embodiments, R 2 R is phenyl. In some embodiments, R c R is an optionally substituted heteroaryl group. In some embodiments, R c R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R c It is an optionally substituted 8-12 membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0037] As defined above and as described herein, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 The linkage is to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another askaloside molecule, or to a linkage via a carbon-containing linker moiety. In some embodiments, R 2 -H, C which is substituted by choice. 1-20 Aliphatic group, optionally substituted C 1-20 These are heteroaliphatic groups, or optionally substituted aromatic groups, or optionally substituted heteroaryl groups.

[0038] In some embodiments, R 2 is -H. In some embodiments, R 2 is a metal cation. In a particular embodiment, R 2 is an organic cation (for example, a nitrogen or phosphorus-centered cationic group). In some embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-20 It is an aliphatic group. In certain embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-12 It is an aliphatic group. In certain embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-8 It is an aliphatic group. In certain embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-6 It is an aliphatic group. In certain embodiments, R 2 R is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In some embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-6 It is an aliphatic group. In some embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-20 It is a heteroaliphatic group. In some embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-6 It is a heteroaliphatic group. In some embodiments, R 2 R is an optionally substituted 3-membered and 8-membered saturated or partially unsaturated heterocycline having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 2 R is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocycline having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 2 R is an optionally substituted aromatic group. In some embodiments, R 2 R is a phenyl compound that is optionally substituted. In some embodiments, R 2R is phenyl. In some embodiments, R 2 R is an optionally substituted heteroaryl group. In some embodiments, R 2 R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 2 It is an optionally substituted 8-12 membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0039] In some embodiments, R 2 It is a glycoside. A glycoside is understood to refer to a portion containing sugar that is linked to another functional group via a glycosidic bond.

[0040] In some embodiments, R 2 R is a nucleotide. In some embodiments, R 2 R is adenosine monophosphate, cytidine monophosphate, guanosine monophosphate, or uridine monophosphate. In some embodiments, R 2 These are deoxyadenosine monophosphate, deoxycytidine monophosphate, deoxyguanosine monophosphate, or deoxythymidine monophosphate.

[0041] In some embodiments, R 2 This is bonding to another askaloside molecule or linking via a carbon-containing linker moiety. In some embodiments, R 2 This includes ascaloside, and optionally substituted C 1-6 It is aliphatic or heteroaliphatic.

[0042] In a particular embodiment, R 2 It contains amino acids. In certain embodiments, R 2 It contains peptides.

[0043] As defined above and described herein, each R 3 These are independently replaced by -H and C of any choice.1-20 Aliphatic group, optionally substituted C 1-20 The linkage is to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another askaloside molecule, or to a linkage via a carbon-containing linker moiety. In some embodiments, each R 3 These are independently -H and C 1-8 Selected from aliphatic species. In some embodiments, one R 3 is -H, and the other R 3 is anything other than -H. In some embodiments, R 3 None of these are -H. In some embodiments, each R 3 is -H. In some embodiments, R 3 The appearance of C is a substitution of C by choice. 1-20 It is an aliphatic group. In some embodiments, R 3 The appearance of C is a substitution of C by choice. 1-6 It is an aliphatic group. In some embodiments, R 3 The appearance of C is a substitution of C by choice. 1-20 It is a heteroaliphatic group. In some embodiments, R 3 The appearance of C is a substitution of C by choice. 1-6 It is a heteroaliphatic group. In some embodiments, R 3 R is an optionally substituted 3-membered and 8-membered saturated or partially unsaturated heterocycline having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 3 R is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocycline having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 3 The appearance of is an optionally substituted aryl group. In some embodiments, R 3 R is a phenyl compound that is optionally substituted. In some embodiments, R 3 R is phenyl. In some embodiments, R 3R is an optionally substituted heteroaryl group. In some embodiments, R 3 R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 3 It is an optionally substituted 8-12 membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0044] In a particular embodiment, at least one R 3 is -H. In certain embodiments, both R 3 The base is -H. In certain embodiments, at least one R 3 This is C, which has been replaced by an optional substitution. 1-20 It is an aliphatic group. In certain embodiments, both R 3 The base is a C that can be the same or different, and can be substituted by any choice. 1-20 It is an aliphatic group. In certain embodiments, at least one R 3 This is C, which has been replaced by an optional substitution. 1-12 It is an aliphatic group. In certain embodiments, at least one R 3 This is C, which has been replaced by an optional substitution. 1-8 It is an aliphatic group. In certain embodiments, at least one R 3 This is C, which has been replaced by an optional substitution. 1-6 It is an aliphatic group. In certain embodiments, at least one R 3 R is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In certain embodiments, at least one R 3 is -CH2CH2OH. In certain embodiments, at least one R 3 is -CH2CH2OR 2 R 2 These are as defined in the genera and subgenera herein. In certain embodiments, at least one R 3 is an optionally substituted aromatic group. In certain embodiments, at least one R3 It contains a glycoside. In a particular embodiment, at least one R 3 It contains amino acids. In certain embodiments, at least one R 3 at least one R 3 It contains peptides. In certain embodiments, at least one R 3 It contains nucleotides.

[0045] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x is an integer from 1 to 22, R a , R b , and R 2 Each of these is as defined above and in the genera and subgenera herein.

[0046] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x, R a , and R b Each of these is as defined above and in the genera and subgenera of this specification.

[0047] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where y is an integer from 1 to 20, R a , R b , and R 2 Each of these is as defined above and in the genera and subgenera of this specification.

[0048] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where y, R a , and R b Each of these is as defined above and in the genera and subgenera of this specification.

[0049] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x and R 2 Each of these is as defined above and in the genera and subgenera of this specification.

[0050] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x is as defined in the genera and subgenera above and herein.

[0051] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, in the formula, y and R 2 Each of these is as defined above and in the genera and subgenera of this specification.

[0052] In a particular embodiment, ascaroside is [ka] A group consisting of is selected, where y is as defined above and in the genera and subgenera of this specification.

[0053] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x, Ra , R b , and R 3 Each of these is as defined above and in the genera and subgenera of this specification.

[0054] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x and R 3 Each of these is as defined above and in the genera and subgenera of this specification.

[0055] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where y, R a , R b , and R 2 Each of these is as defined above and in the genera and subgenera of this specification.

[0056] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, in the formula, y and R 3 Each of these is as defined above and in the genera and subgenera of this specification.

[0057] In one embodiment, an ascaloside useful in the context of this disclosure has a general structure (I), where Z is -CH(CH3)-(CH2) n -CO2R 2 And n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted. 1-20 These are aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0058] In one embodiment, an ascaloside useful in the context of this disclosure has a general structure (I), where Z is -CH(CH3)-(CH2) n -CH=CH-CO2R 2 And n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted. 1-20 These are aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0059] Specific ascalosides useful in the context of this disclosure include, but are not limited to, ascr#7 and ascr#18. [ka]

[0060] In certain embodiments, the ascaloside used in the provided method and composition is selected from the group consisting of ascr#9, ascr#12, ascr#14, ascr#1, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, ascr#24, ascr#26, ascr#28, ascr#30, ascr#32, ascr#34, and ascr#36. In certain embodiments, the ascaloside used in the provided method is selected from the group consisting of ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. In certain embodiments, the ascaloside used in the provided method is selected from the group consisting of ascr#9, ascr#14, ascr#10, and ascr#18.

[0061] In certain embodiments, the ascaloside used in the provided method and composition is selected from the group consisting of ascr#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 certain embodiments, the ascaloside used in the provided method is selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22. In certain embodiments, the ascaloside 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 certain embodiments, the ascaloside used in the provided method is selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

[0062] In a particular embodiment, the ascaloside used in the provided method and composition 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.

[0063] In certain embodiments, the ascaloside used in the provided method and composition 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.

[0064] In certain embodiments, the ascaloside used in the provided method and composition is selected from the group consisting of ascr#18, oscr#16, oscr#17, oscr#18, 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.

[0065] In certain embodiments, the ascaloside used in the provided method and composition is selected from the group consisting of ascr#18, oscr#16, oscr#18, and any combination of two or more of these.

[0066] In certain embodiments, the ascaloside used in the provided method and composition is a blend comprising two or more of ascr#18, ascr#17, ascr#10, ascr#3, ascr#1, ascr#7, and ascr#9.

[0067] In certain embodiments, the ascaloside used in the provided method and composition is a blend comprising two or more of oscr#18, oscr#17, oscr#16, oscr#15, oscr#10, oscr#3, oscr#14, oscr#1, oscr#7, oscr#12, and oscr#9. In certain embodiments, the ascaloside used in the provided method and composition is a blend comprising two or more of oscr#18, oscr#16, oscr#10, oscr#14, oscr#1, oscr#12, and oscr#9. In certain embodiments, the ascaloside used in the provided method and composition is ascr#18. In certain embodiments, the ascaloside used in the provided method and composition is ascr#16.

[0068] Ascalosides can be obtained from natural sources (e.g., nematodes) or they can be prepared synthetically. Ascalosides can be prepared synthetically, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascarilose. An exemplary method for preparing ascalosides includes 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 1-O-substituted ascarilose. In certain embodiments, the formation of the monosulfonate ester is carried out on a substrate that does not contain a hydroxyl protecting group at the 2- or 4-position of the rhamnose starting material. In certain embodiments, such a method includes contacting the starting material with a sulfonating agent (i.e., a sulfonyl halide, sulfonic anhydride, or similar reagent) in the presence of a Lewis acid. Specific details relating to the synthesis of 1-O-substituted ascarilose can be found in International Publication No. WO2022 / 024067, incorporated herein by reference.

[0069] Ascaloside Salt In certain embodiments, the ascaloside in the provided solid composition comprises an ascaloside salt. The ascaloside salt can be formed with a suitable reagent, for example, any suitable acidic or basic functional group on the ascaloside molecule.

[0070] In some embodiments, the salt provided is of formula II', [A] p - M p+ (Formula II) In the formula, A, M, and p are defined and described below and in this specification.

[0071] For example, in some embodiments, carboxylic acid salts (also known as carboxylate salts) are provided. Such salts may be described according to the following formula II, where "M" is a metal (or other cation) and "A" is the remainder of the askaloside molecule to which the carboxylic acid moiety is attached (e.g., the structure according to formula I provided herein). [A-(C(O)O) - ] p M p+ (Formula II) p represents an integer between 1 and 4. In some embodiments, p is 1, and the salt contains one askaroside anion and one "M" cation (with a +1 charge). In some embodiments, p is 2, and the salt contains two askaroside anions and one "M" cation (with a +2 charge). In some embodiments, p is 3, and the salt contains three askaroside anions and one "M" cation (with a +3 charge). In some embodiments, p is 4, and the salt contains four askaroside anions and one "M" cation (with a +4 charge). In embodiments where p is greater than 1, the askaroside anions present in the salt may be the same or different.

[0072] Referring to the structure of ascaloside in formula I above, the carboxylate salt is, for example, the "OR" of the tetrahydropyranyl ring. a " and / or "OR b Note that it can be formed with substituents. In some embodiments, the carboxylic acid is OR a and / or OR b It may be formed by substituents, R a and / or R b is -LC(O)OR c L is an optionally substituted divalent linker containing one or more carbon atoms and optionally containing one or more heteroatoms, and R c is H. In some embodiments, the carboxylic acid is OR a and / or OR bIt may be formed by substituents, R a and / or R b This is a sugar moiety containing a carboxylic acid group (e.g., a sugar acid). In some embodiments, the carboxylic acid is OR a and / or OR b It may be formed by substituents, R a and / or R b It is a peptide containing a carboxylic acid group. In some embodiments, the carboxylic acid is OR a and / or OR b It may be formed by substituents, R a and / or R b It is a polymer containing a carboxylic acid group. In some embodiments, the carboxylic acid is OR a and / or OR b It may be formed by substituents, R c This is a polymer chain containing a carboxylic acid group. In some embodiments, the carboxylic acid is OR a and / or OR b It may be formed by substituents, R a and / or R b is a monoester of a dibasic acid. In certain embodiments, such a compound is R a and / or R b These compounds originate from the reaction of a compound with -H with a cyclic acid anhydride such as phthalic anhydride, succinic anhydride, maleic anhydride, or glutaric anhydride, or their substituted analogs. Representative examples of such ascaloside anions are shown below. [ka] In the formula, x and R 2 Each of these is as defined above and in the genera and subgenera of this specification.

[0073] Referring again to the structure of the ascaloside of formula I described above, it should be noted that the carboxylic acid can be formed, for example, by an OZ substituent on a tetrahydropyranyl ring. In some embodiments, the carboxylic acid is, for example, Z is -CH(CH3)-(CH2) n -CO2R 2-CH(CH3)-(CH2) n -CH=CH-CO2R 2 ,-CH(CH3)-(CH2) n -CH(OH)-CH2-CO2R 2 -CH(CH3)-(CH2) n -C(O)-CH2-CO2R 2 ,-(CH2) n -CO2R 2 ,-(CH2) n -CH=CH-CO2R 2 , and -(CH2) n -CH(OH)-CH2-CO2R 2 Selected from, where n is an integer from 1 to 40, R 2 However, C is replaced by -H or of any choice. 1-20 If selected from nucleotides containing aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or carboxylic acid groups, they can be formed with OZ substituents.

[0074] In certain embodiments, the linker group -L- is optionally replaced with C 1-20 aliphatic, C 1-20 The linkers include heteroaliphatic, aryl, or heteroaryl groups. Such linkers may contain ether bonds, ester bonds, carbonate bonds, or carbamate bonds (e.g., A-OC(O)NR). 3 -), thioester bond (e.g., A-OC(S)-), thiocarbamate bond (e.g., A-OC(S)NR) 3 It can bond to the oxygen atom on the ascaloside molecule via a thiocarbonate bond (e.g., A-OC(S)O-), a dithiocarbonate bond (e.g., A-OC(S)S-), a sulfonate ester bond (e.g., A-OSO2-), or via a bond through the phosphorus atom.

[0075] In one embodiment, a salt of ascr#18 is provided, for example, according to the following formula. [ka] In the formula, the negative charge is shown to be delocalized on the oxygen atom of the carboxylic acid.

[0076] This disclosure is not limited to carboxylate salts of ascaloside. Salts that may be formed on ascaloside molecules with other functional groups are also included in this disclosure. For example, ascaloside may have an amine group (e.g., R a , R b If the askaloside contains a hydroxyl (-OH) group, the ammonium salt may be formed with a suitable anionic group. Furthermore, in some embodiments in which the askaloside contains a hydroxyl (-OH) group, a specific M group may coordinate to it to form a salt, such as in a borate or silicate derivative of the askaloside.

[0077] The following are representative non-restrictive metal salts of ascalosides formed via the carboxylic acid group of the side chain. [ka] In the formula, x is as defined above and in the genera and subgenera herein.

[0078] The following are representative "ate" salts of ascalosides formed via the hydroxyl group of ascarilose sugar. [ka] In the formula, x is as defined above and in the genera and subgenera herein.

[0079] The composition of "M" (for example, as shown in formulas II and IIb above) can vary widely. In some embodiments, M is a metal. Preferred metals are not particularly limited and in various embodiments are selected from alkali / group 1 metals, alkaline earth / group 2 metals, and transition metals. In some embodiments, M is a metalloid or nonmetal selected from the main group elements. In some embodiments, M is an organic cation such as ammonium, guanidinium, amidinium, pyridinium, phosphonium, sulfonium, or any similar nitrogen, phosphorus, or sulfur-centered cation or analogue.

[0080] In some embodiments, M comprises plant micronutrients or plant macronutrients. Plant micronutrients and macronutrients include, but are not limited to, nitrogen (N), phosphorus (P), potassium (K), calcium (Ca), magnesium (Mg), boron (B), silicon (Si), zinc (Zn), manganese (Mn), iron (Fe), copper (Cu), molybdenum (Mo), and nickel (Ni). Those skilled in the art will understand that not all such micronutrients and macronutrients can form salts with ascalosides in the same manner.

[0081] For example, salts of plant nutrients such as potassium, calcium, magnesium, zinc, manganese, iron, copper, molybdenum, and nickel can be formed in some embodiments with carboxylic acids on ascalosides (e.g., according to formula II or IIb above). Nitrogen is provided by ammonium or guanidinium salts of ascalosides (e.g., M is NH4). + or H2N + =C(NH2)2) or ammonium or guanidinium analog salts of ascaloside (e.g., NH4 + or H2N +It may be provided in the form of (=C(NH2)2 in which one or more of the H atoms are replaced by alkyl groups). Plant nutrients such as boron, silicon, and molybdenum may not readily form salts with carboxylic acids, but may coordinate to the free OH present on the askaloside molecule, for example in the form of borate, silicate, or molybdate, to form suitable salts. Thus, in some embodiments, salts containing at least one boron atom coordinated to the askaloside, salts containing at least one silicon atom coordinated to the askaloside, or salts containing at least one molybdenum atom coordinated to the askaloside are provided.

[0082] Further details relating to ascaloside salts can be found in International Publication No. 2023 / 220174, filed on 10 May 2023, which is incorporated herein by reference.

[0083] Solid ascaloside composition Ascaloside may be applied to plants and crops by various means, and the mode of application is not particularly limited, as plants can respond systemically to ascaloside. Non-limiting examples of preferred modes of application of ascaloside include seed treatment, foliar spraying or application, root immersion or drenching, soil application, application of time-release formulations, injection into stems or trunks, or application of compositions for absorption through the bark (e.g., stems, trunks, branches, or vines). Most of these methods of applying ascaloside rely on the use of an aqueous solution of ascaloside.

[0084] For typical agricultural applications, the application rate of ascaloside in a field ranges from approximately 5 mg / acre to approximately 100 mg / acre, with 25 mg / acre to 50 mg / acre being preferable for most crops. For spraying rates ranging from 5 gallons / acre to 50 gallons / acre, the required ascaloside concentration in the sprayer tank ranges from approximately 5 mg / 50 gallons (0.1 mg / gallon) to approximately 100 mg / 5 gallons (20 mg / gallon). Accurate measurement of amounts less than 1 g is impractical in agricultural fields. Furthermore, even if it is possible to measure subgram amounts of ascaloside, or if subgram amounts of the material can be supplied to growers (e.g., as material packets), ensuring the complete and homogeneous dissolution of less than 1 g of ascaloside in several gallons of water is difficult, if not impossible, in typical agricultural fields.

[0085] One way to mitigate these problems is to supply a liquid concentrate containing one or more ascalosides that can be easily dispensed into a sprayer tank. In one embodiment, a concentrated solution of one or more ascalosides can be prepared to have a volume of 1 quart (1 L) to 2.5 gallons (10 L). For example, at an application ratio of 25 mg / acre, an aqueous concentrate containing 422 mg of one or more ascalosides per liter provides a concentrate requiring application of approximately 2 ounces (60 mL) of concentrate per acre. For each acre to be treated, dilute 2 ounces of concentrate in water (typically 5–20 gallons (19–76 L)) for spraying. This formulation, packaged in standard 2.5-gallon (10 L) watering cans, provides sufficient material to treat 160 acres, meeting grower expectations. Even in concentrate form, the solution contains only 422 ppm of ascaloside and is 99.96% water. Shipping, storing, and distributing the concentrate form is an inefficient cost in terms of the actual amount of ascaloside delivered.

[0086] In one embodiment, instead of providing crop farmers / cultivators with a pre-mixed aqueous concentrate, a solid ascaloside composition comprising one or more ascalosides and a solid carrier composition can be dispensed. By providing a sufficient amount of the solid carrier composition, one or more ascalosides are provided in a form that can be easily measured and mixed with water (e.g., at any point before use or immediately before use). Transporting such a solid ascaloside composition substantially reduces the cost of transporting ascalosides to cultivators and provides a composition that cultivators can handle with ease. Such a solid ascaloside formulation can be provided as fine particles (e.g., a powder or granular composition) or in other solid forms such as tablets, wafers, or similar regular aggregate forms, each containing a specified amount of ascaloside.

[0087] In one embodiment, the provided solid ascaloside composition is a particulate composition comprising one or more ascalosides and a particulate carrier. The one or more ascalosides include, but are not limited to, any ascalosides or salts of ascalosides described herein. The one or more ascalosides are blended with the particulate carrier composition. The particulate carrier provides additional bulk to the ascaloside particulate composition and facilitates the convenient preparation of highly diluted solutions of ascalosides. In addition, the particulate carrier composition may contain one or more compounds that improve the solubility of one or more ascalosides in water.

[0088] In one embodiment, the provided solid ascaloside composition comprises a tablet composition comprising one or more ascalosides and a solid carrier formed into an integrated shape, preferably such tablets being of a specific weight and shape to allow for simple measurement of the target ascaloside application amount by using an appropriate number of tablets. The one or more ascalosides include, but are not limited to, any ascalosides or salts of ascalosides described herein. The provided tablets comprise one or more ascalosides blended with the solid carrier composition and, optionally, a binder or coating necessary to form an integrated tablet. The carrier provides additional bulk to the ascaloside composition and facilitates the convenient preparation of highly diluted solutions of ascalosides. In addition, the tablet composition may contain one or more compounds that improve the solubility of one or more ascalosides in water.

[0089] The concentration of one or more ascalosides in a solid ascaloside composition can be pre-selected based on the intended use. In certain embodiments, the solid ascaloside composition contains one or more ascalosides in an amount of 20% by weight or less. In additional embodiments, the ascaloside fine particle composition contains one or more ascalosides in an amount of 15% by weight or less, one or more ascalosides in an amount of 10% by weight or less, one or more ascalosides in an amount of 5% by weight or less, one or more ascalosides in an amount of 2% by weight or less, or one or more ascalosides in an amount of 1% by weight or less. In certain embodiments, the solid ascaloside composition contains one or more ascalosides in an amount of about 5% to about 20% by weight. In certain embodiments, the solid ascaloside composition contains one or more ascalosides in an amount of about 5% to about 15% by weight. In certain embodiments, the solid ascaloside composition contains one or more ascalosides in an amount of about 5% to about 10% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in about 1% to about 20% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in about 10% to about 20% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in about 10% to about 15% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in about 15% to about 20% by weight. The solid askaloside composition having one or more askalosides in about 1% to about 20% by weight is particularly useful for forming concentrated solutions of askaloside intended to be further diluted before use. This may be more convenient for growers than directly mixing solid askaloside formulations into a spray tank, as visibility may be poor and / or the options for vigorous mixing may be limited, and it may be difficult to ensure complete dissolution of the solid in the spray tank. Such compositions are particularly useful in commercial settings for preparing compositions for large-area treatments, such as row crop acres or large-scale hydroponic systems.In certain embodiments, such a solid ascaloside composition may be provided in a container suitable for forming such a concentrate, for example, a pre-measured amount of solid can be provided in a nearly empty 2.5-gallon jug that can be filled with water on-site, before use, to provide 2.5 gallons of liquid ascaloside concentrate for application at a rate of 1 to 4 fluid ounces per acre.

[0090] To prepare a solution of askaloside suitable for direct use without further dilution, a solid askaloside composition is provided containing one or more askalosides in less than about 0.5% by weight. In certain embodiments, such a composition contains one or more askalosides in less than about 0.4% by weight, less than about 0.3% by weight, less than about 0.25% by weight, less than about 0.2% by weight, less than about 0.15% by weight, less than about 0.1% by weight, less than about 0.05% by weight, less than about 0.01% by weight, or less than about 0.005% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in about 0.005% to about 1% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in about 0.005% to about 0.05% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in about 0.005% to about 0.5% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in an amount of about 0.005% to about 0.1% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in an amount of about 0.1% to about 1% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in an amount of about 0.05% to about 1% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in an amount of about 0.5% to about 1% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in an amount of about 0.05% to about 0.5% by weight. In certain embodiments, the solid askaloside composition contains one or more askalosides in an amount of about 0.01% to about 0.1% by weight. Ascaloside particulate compositions containing one or more ascalosides in an amount of approximately 0.01% to approximately 0.1% by weight are particularly useful for forming ascaloside compositions that do not require further dilution before use. Such compositions are particularly convenient for preparing compositions for treatment of relatively small areas such as home gardens, ornamental plants, lawns, or individual trees and shrubs.In certain embodiments, such a solid ascaloside composition may be provided in a container suitable for forming a liquid formulation in the field, for example, in a quart or gallon spray bottle, in which a pre-measured amount of solid can be filled with water in the field and sprayed directly onto plants to provide an effective application ratio of ascaloside.

[0091] To avoid any ambiguity, whereever a solid ascaloside composition is referred to in this disclosure as "weight %", it will be understood that "weight %" refers to the weight of the individual components relative to the total weight of the composition.

[0092] In some embodiments, the ascaloside in the provided solid ascaloside composition exists in salt form. The counterions of the salt form of ascaloside may include elements that are also useful as phytonutrients. Phytonutrients include, but are not limited to, nitrogen (N), phosphorus (P), potassium (K), calcium (Ca), magnesium (Mg), boron (B), silicon (Si), zinc (Zn), manganese (Mn), iron (Fe), copper (Cu), molybdenum (Mo), and nickel (Ni). Phytonutrients can exist in cationic or anionic form. These elements may be oxidized to form ionic forms.

[0093] In one embodiment, the carrier composition comprises one or more water-soluble fillers. Examples of water-soluble fillers include, but are not limited to, carbohydrates, neutral inorganic salts, polyethylene glycol, and polypropylene glycol.

[0094] Examples of carbohydrates that can be used as water-soluble fillers include, but are not limited to, lactose, glucose, fructose, mannose, mannitol, sucrose, powdered sugar, microcrystalline cellulose, starch, and powdered cellulose.

[0095] Examples of neutral inorganic salts that can be used as water-soluble fillers include, but are not limited to, calcium nitrate, calcium chloride, copper(II) phosphate, copper(I) chloride, copper(II) carbonate, copper(I) iodide, iron(II) molybdate, potassium sulfate, potassium bromide, potassium chloride, potassium nitrate, magnesium nitrate, magnesium chloride, magnesium sulfate, sodium sulfate, sodium chloride, sodium nitrite, and sodium nitrate.

[0096] As described herein, when used in ascaloside particulate compositions, polyethylene glycol or polypropylene glycol must be solid at temperatures up to about 40°C. For example, polyethylene glycol having an average molecular weight of about 3000 to about 8000 is generally suitable as a water-soluble filler. Polyethylene glycol and polypropylene glycol may have the additional advantage of improving the solubility of ascalosides in water. In one embodiment, the amount of polyethylene glycol and / or polypropylene glycol present in the particulate carrier composition is sufficient to increase the solubility of one or more ascalosides in water.

[0097] In one embodiment, the solid carrier composition in the provided solid ascaloside composition contains one or more pH adjusting agents. The one or more pH adjusting agents that may be included in the carrier composition include pH reducing agents and pH increasing agents. pH reducing agents decrease the pH of water when dissolved in pure water. pH increasing agents increase the pH of water when dissolved in pure water.

[0098] Examples of pH-reducing agents include, but are not limited to, ammonium sulfate, calcium dihydrogen phosphate, copper(II) nitrate, copper(II) bromide, copper(II) chloride, copper(II) sulfate, boric acid, potassium dihydrogen phosphate, sodium sulfite, sodium dihydrogen phosphate, sodium bisulfite, sodium bisulfite, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium bisulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide.

[0099] Examples of pH-increasing agents include, but are not limited to, ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium bicarbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium bicarbonate (potassium hydrogen carbonate), potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium bicarbonate (sodium bicarbonate), sodium hydroxide, ammonium bicarbonate, zinc hydroxide, and zinc carbonate.

[0100] In preferred embodiments, the pH increasing agent is a carbonate, bicarbonate, or phosphate salt. In some embodiments, the pH increasing agent is a bicarbonate. In some embodiments, the pH increasing agent contains one or more carbonates, bicarbonates, or phosphate salts. In some embodiments, the pH increasing agent contains one or more carbonates. In some embodiments, the pH increasing agent contains one or more bicarbonates. In some embodiments, the pH increasing agent contains one or more phosphate salts. In some embodiments, the pH increasing agent contains sodium bicarbonate and potassium bicarbonate. In some embodiments, the pH increasing agent is sodium bicarbonate. In some embodiments, the pH increasing agent is potassium bicarbonate. In addition to acting as pH increasing agents, carbonates, bicarbonates, and phosphate salts are also useful for buffering soil pH against acidification. In addition, carbonates can sequester heavy metals in the soil surrounding plants. Phosphates are used as fertilizers to promote plant growth and development.

[0101] In some embodiments, the solid askaloside composition contains about 80% to about 99% by weight of a pH increasing agent. In some embodiments, the solid askaloside composition contains about 80% to about 95% by weight of a pH increasing agent. In some embodiments, the solid askaloside composition contains about 80% to about 90% by weight of a pH increasing agent. In some embodiments, the solid askaloside composition contains about 99% to about 99.995% by weight of a pH increasing agent. In some embodiments, the solid askaloside composition contains about 99% to about 99.95% by weight of a pH increasing agent. In some embodiments, the solid askaloside composition contains about 99% to about 99.9% by weight of a pH increasing agent.

[0102] In some embodiments, the advantage of a pH increaser is that increasing the pH of the solution can increase the solubility of ascalosides having a carboxylic acid moiety. In addition, or alternatively, if the ascaloside is in salt form, and the water used to prepare the composition is acidic, the use of a pH increaser can help maintain the salt form of the ascaloside.

[0103] In some embodiments, the provided solid askaloside composition comprises one or more askalosides, characterized in that the one or more askalosides exhibit solubility of at least 1, 3, 6, 9, 12, 15, 20, or 25 grams / gallon of water. In some embodiments, the provided solid askaloside composition comprises one or more askalosides, characterized in that the one or more askalosides exhibit solubility of at least 0.1, 1, 10, 50, or 100 mM of water. In some embodiments, the provided solid askaloside composition comprises one or more askalosides, characterized in that the one or more askalosides exhibit solubility of at least 0.2, 0.3, 0.4, 0.5, 0.75, or 1 M of water. In some embodiments, solubility is measured at room temperature (e.g., 25°C).

[0104] In some embodiments, the provided solid askaloside composition comprises one or more askalosides, characterized in that the one or more askalosides exhibit solubility in water at least 50%, 75%, 100%, 1,000%, 5,000%, or 10,000% higher than the reference. In some embodiments, the reference is a corresponding composition containing only one or more askalosides.

[0105] Ascalosides containing carboxylic acids can react with pH increasing agents (e.g., carbonates) to form carboxylate salts. Carboxylate salts of ascalosides have increased water solubility. The use of pH increasing agents has the advantage of promoting in-situ salt formation in ascalosides containing carboxylic acids. In some embodiments, a solid ascaloside composition consists essentially of or comprises one or more ascalosides and carbonate salts. In some embodiments, a solid ascaloside composition consists essentially of or comprises one or more ascalosides and bicarbonate salts. In some embodiments, a solid ascaloside composition consists essentially of or comprises one or more ascalosides and phosphate salts. In some embodiments, such carbonate salts, bicarbonate salts, or phosphate salts contain potassium, sodium, or quaternary ammonium cations. A solid ascaloside composition may contain one or more ascalosides, one or more water-soluble fillers, and one or more pH adjusters.

[0106] In some embodiments, the solid askaloside composition consists essentially of one or more askalosides and sodium bicarbonate. In some embodiments, the solid askaloside composition consists essentially of one or more askalosides and potassium bicarbonate. In some embodiments, the solid askaloside composition consists of one or more askalosides and sodium bicarbonate. In some embodiments, the solid askaloside composition consists of one or more askalosides and potassium bicarbonate.

[0107] In some embodiments, the solid askaloside composition consists essentially of one or more askalosides and sodium carbonate. In some embodiments, the solid askaloside composition consists essentially of one or more askalosides and potassium carbonate. In some embodiments, the solid askaloside composition consists of one or more askalosides and sodium carbonate. In some embodiments, the solid askaloside composition consists of one or more askalosides and potassium carbonate.

[0108] In some embodiments, the present disclosure provides solid ascaloside compositions comprising: One or more ascalosides, and A means for dissolving one or more ascalosides in water at concentrations of at least approximately 0.1, 1, 10, 50, or 100 mM.

[0109] In some embodiments, the present disclosure provides solid ascaloside compositions comprising: One or more ascalosides, and A means for dissolving one or more ascalosides in water at a concentration of at least about 0.2, 0.3, 0.4, 0.5, 0.75, or 1 M.

[0110] In some embodiments, the present disclosure provides solid ascaloside compositions comprising: One or more ascalosides, and A means for dissolving one or more ascalosides in water at a concentration of at least about 1, 3, 6, 9, 12, 15, 20, or 25 grams / gallon.

[0111] In some embodiments, the means for dissolving one or more ascalosides includes a pH adjuster. In some embodiments, the means for dissolving one or more ascalosides includes a pH increaser. In some embodiments, solubility is measured at room temperature (e.g., 25°C).

[0112] In some embodiments, the present disclosure provides solid ascaloside compositions comprising: One or more ascalosides, and A means for enhancing the solubility (e.g., in water) of one or more ascalosides.

[0113] In some embodiments, means for enhancing the solubility of one or more ascalosides include a pH adjuster. In some embodiments, means for enhancing the solubility of one or more ascalosides include a pH increaser. In some embodiments, the solubility of one or more ascalosides is increased by at least 50%, 75%, 100%, 1,000%, 5,000%, or 10,000% above the reference value. In some embodiments, the solubility is measured at room temperature (e.g., 25°C).

[0114] In some embodiments, the present disclosure provides solid ascaloside compositions comprising: One or more ascalosides, and A means for providing an aqueous ascaloside composition in which the concentration of one or more ascalosides is at least about 0.1, 1, 10, 50, or 100 mM.

[0115] In some embodiments, the present disclosure provides solid ascaloside compositions comprising: One or more ascalosides, and A means for providing an aqueous ascaloside composition in which the concentration of one or more ascalosides is at least about 0.2, 0.3, 0.4, 0.5, 0.75, or 1 M.

[0116] In some embodiments, the present disclosure provides solid ascaloside compositions comprising: One or more ascalosides, and A means for providing an aqueous ascaloside composition in which the concentration of one or more ascalosides is at least about 1, 3, 6, 9, 12, 15, 20, or 25 grams / gallon.

[0117] In some embodiments, the means for providing the ascaloside aqueous composition includes a pH adjuster. In some embodiments, the means for providing the ascaloside aqueous composition includes a pH increaser. In some embodiments, solubility is measured at room temperature (e.g., 25°C).

[0118] Microorganisms, including fungi and molds, have been found to be able to grow in aqueous ascaloside solutions containing the ascaloside aqueous concentrate described above, which can be addressed by packaging such solutions under sterile conditions. However, problems still arise when such solution packaging is opened and then stored in a non-sterile environment (e.g., a farm), as this may impair the shelf life of the product after opening. This is a further drawback of providing commercially available ascaloside formulations as diluted aqueous solutions. Solutions produced from the solid ascaloside formulations provided herein have been found to have higher stability against microbial contamination than pure ascaloside solutions. Fungal growth can be reduced or inhibited in such solutions, particularly when pH adjusters are used to raise the pH of the ascaloside solution. In certain embodiments, a solid ascaloside composition is provided that, when dissolved in water, provides an ascaloside solution having enhanced stability against microbial contamination or growth (e.g., growth of mold or fungi). In certain embodiments, such a composition comprises one or more ascalosides and one or more pH adjusters that increase the pH of the resulting solution. In certain embodiments, such pH adjusters are provided in molar excess for any acidic functionality of the ascaloside(s) such that when the composition is dissolved in water, the ascaloside solution has a pH greater than 7 (e.g., greater than 7.5, greater than 8, greater than 8.5, greater than 9, or greater than 9.5).

[0119] Solid ascaloside compositions can be prepared from any technique used in dry blending. Dry blending techniques include, but are not limited to, dry mixing, dry granulation, wet granulation, melt granulation, high-shear mixing, and low-shear mixing. Solid ascaloside particulate compositions can be formed into granular materials by known means, including the use of binders and granulation. Powder formulations may benefit from including anti-caking agents or moisture-controlling additives to keep the material in a free-flowing state. Solid ascaloside compositions, including tablets, pellets, wafers, spheres, or similar regular solid forms, can be prepared by known means, including pressing, molding, and extrusion. Such compositions may benefit from incorporating binders to help the materials adhere in the solid and / or coating to improve the appearance, handling properties, or stability of such solid forms.

[0120] Granulation is generally the process by which powder particles adhere to each other to form granules. Granulation is useful because it produces a relatively uniform mixture of particles of various sizes. Dry granulation processes can be used to form ascaloside fine particle compositions without the use of liquid solutions. Dry granulation may be performed on a press using slugging tooling or on a roller compactor, commonly referred to as a chill sonar.

[0121] Wet granulation involves forming granules using a granulation fluid or wetting agent, which is later removed by drying. Suitable solvents include, but are not limited to, acetone, methanol, ethanol, ethyl ether, ethyl acetate, chlorinated solvents, or mixtures thereof. Granulators can be low-shear, medium-shear, or high-shear. Shear is the amount of mechanical force applied to the granulator. Low-shear granulators use very little mechanical force to combine the powder. Fluidized bed granulators use a large volume of airflow to raise the powder in the chamber for mixing. Fluidized bed granulators form lightly held powder into granules by relying instead on the powder properties and binding solution, rather than by applying mechanical energy. After the granulation process is complete, the resulting mixture may be dried to remove at least some of the solvent.

[0122] Melt granulation is a process in which powder is converted into a solid aggregate or granule while heated. It is similar to wet granulation, except that the binder acts as a wetting agent only after it has melted.

[0123] Use of solid ascaloside compositions Solid ascaloside compositions, as disclosed herein, generally dissolve in water to form a solution containing one or more ascalosides. In one embodiment, the solid ascaloside composition is provided to the user in a container. Examples of containers include, but are not limited to, canisters, cans, drums, bottles, bags, or pouches. Containers can be made from polymers, glass, or metal. Ascaloside particulate compositions are generally provided with instructions on how to prepare a solution from the solid ascaloside composition. Such instructions may include the amount (e.g., by weight or volume) of the ascaloside particulate composition and the amount of water to which the solid ascaloside composition is added. For example, the instructions may include the weight of the ascaloside particulate composition per gallon of water. In another example, the instructions may include the volume of the ascaloside particulate composition per gallon of water. To aid mixing, a scoop designed to contain the appropriate amount of ascaloside particulate composition per given amount of water may be provided.

[0124] Alternatively, the ascaloside particulate composition can be packaged in single-use containers. In one embodiment, a single-use container may contain enough ascaloside particulate composition to be added to a predetermined amount of water. For example, a single-use container may contain enough ascaloside composition to be added to 1 gallon (3.8 L) of water. The single-use container may include instructions for adding the entire contents of the ascaloside container to a separate container containing an appropriate amount of water.

[0125] Single-use containers may be designed to form ascaloside concentrated solutions. As used herein, “concentrated solution” refers to a solution of one or more ascalosides in water, where the concentration of ascaloside is greater than the concentration of ascaloside in water required for application. Before use, the concentrated solution must be diluted. In certain embodiments, the ascaloside in the single-use container is intended to be added to approximately 1 quart (e.g., a 1-quart bottle) to approximately 300 gallons (e.g., an IBC tote). In a particular embodiment, the provided solid ascaloside composition is packaged in single-use packaging sufficient to produce a concentrated ascaloside solution when dissolved in a bottle or bucket (for example, having a volume of about 0.5 gallons (1.9 L), about 1.0 gallon (3.8 L), about 1.5 gallons (5.7 L), about 2.0 gallons (7.6 L), about 2.5 gallons (9.5 L), about 3 gallons (11.4 L), 4 gallons (15.1 L), or 5 gallons (18.9 L)). In certain embodiments, the provided solid ascaloside composition is packaged in single-use packaging sufficient to produce a concentrated ascaloside solution when dissolved in a drum or tank (e.g., a plastic or metal drum having a volume of about 10 gallons, about 20 gallons, about 30 gallons, or about 55 gallons, or an IBC tote having a volume of about 110 gallons, about 120 gallons, about 140 gallons, about 180 gallons, about 220 gallons, about 250 gallons, about 275 gallons, about 300 gallons, about 330 gallons, about 350 gallons, about 450 gallons, or about 550 gallons). The concentrated solution obtained from dissolving the solid ascaloside composition according to the provided instructions typically has an ascaloside concentration of about 0.05 mM to 10 mM.

[0126] In general, the amount of solid ascaloside composition added to a concentrate should not exceed the solubility of the components of the solid ascaloside composition. In certain embodiments, the provided solid ascaloside composition has an ascaloside content and associated instructions for use such that the concentrated ascaloside solution obtained from the dissolution of the provided ascaloside solid composition according to the instructions has a concentration such that the application of the concentrate (e.g., after further dilution to an appropriate spray volume) of about 0.5 fluid ounces (15 mL) to about 8 ounces (240 mL) per acre of crop to be treated provides effective application of ascaloside to the crop (e.g., reducing crop damage by pathogens). In certain embodiments, the provided solid ascaloside composition is formulated so that the dissolution of the solid is in the range of about 1 tablespoon (15 mL) to about 1 / 2 cup (120 mL) per gallon (high concentration). This provides a good balance between producer convenience (easily measurable and rapidly dissolving quantities) and logistical efficiency (minimizing storage and transport of inactive components). In certain embodiments, the provided solid ascaloside composition is formulated such that dissolving approximately one tablespoon (15 mL) of solid per gallon provides a concentrated solution.

[0127] Single-use containers can also be designed to contain an amount of ascaloside such that the dissolution of the entire contents provides an ascaloside solution of the approximate concentration needed for application to plants without further dilution. For example, a single-use product targeted at row crop growers may be provided in an amount such that the entire contents of the single-use package, when added directly to a spray tank, treats several acres (e.g., 1 to 100 acres). Such single-use packages can also target smaller growers or home gardeners by providing packaging that provides a volume of ready-to-spray solution that conveniently delivers an effective amount of ascaloside when applied to smaller areas such as gardens or individual plants, when its entire contents are dissolved in a smaller volume of water (e.g., 0.5 to 5 gallons). The ready-to-use solution obtained from the dissolution of a solid ascaloside composition according to the provided instructions typically has an ascaloside concentration of about 25 nM to about 10 uM. In certain embodiments, the provided solid askaloside composition is formulated such that dissolving about 1 tablespoon (15 mL) of solid per gallon provides a solution with an askaloside concentration of about 1 micromol / liter. In certain embodiments, the provided solid askaloside composition is formulated such that dissolving about 1 tablespoon (15 mL) of solid per gallon provides a solution with an askaloside concentration of about 5 micromoles / liter. In certain embodiments, the provided solid askaloside composition is formulated such that dissolving about 1 tablespoon (15 mL) of solid per gallon provides a solution with an askaloside concentration of about 100 nanomoles.

[0128] In an alternative embodiment, the solid ascaloside composition can be dispensed to an end user in a nearly empty container configured to hold a predetermined amount of water. Therefore, the instructions only include instructions for adding the appropriate amount of water to the container. The container may be designed for the formation of a concentrated solution of the ascaloside particulate composition. Alternatively, the container may be designed for the formation of a ready-to-use ascaloside solution having the appropriate concentration of ascaloside after water is added to the container.

[0129] In addition, the formulation may contain “adjuvant surfactants” that can enhance the deposition, wetting, and penetration of the compound into target crops and organisms. These “adjuvant surfactants” may be used as components of the composition. The amount of adjuvant surfactant typically varies from 0.01 to 1.0% by weight, preferably from 0.05 to 0.5% by weight. Suitable adjuvant surfactants include ethoxylated nonylphenol, ethoxylated synthetic or natural alcohols, esters or sulfosuccinate salts, ethoxylated organosilicones, ethoxylated fatty amines, blends of surfactants with mineral oil or vegetable oil, crop oil concentrates (mineral oil (85%) + emulsifier (15%)), nonylphenol ethoxylate, benzyl cocoalkyldimethylquaternary ammonium salts, petroleum hydrocarbons, alkyl esters, organic acids, and blends of anionic surfactants, C9-Cu alkyl polyglycoside, phosphoric acid alcohol ethoxylate, natural primary alcohol (C 12 -C 16 Examples include, but are not limited to, ethoxylates, di-sec-butylphenol EO-PO block copolymers, polysiloxane-methyl caps, nonylphenol ethoxylate + ammonium urea nitrate, emulsified methylated seed oils, tridecyl alcohol (synthetic) ethoxylate (8EO), tallow amine ethoxylate (15EO), and PEG(400)-dioleate-99. The formulation may also include oil-in-water emulsions.

[0130] In the case of hydrated formulations, the "surfactant" may account for approximately 0.5% to 10% of the composition. Suitable "surfactants" for hydrated formulations include nonionic surfactants such as sulfonated lignin, condensed naphthalene sulfonate, naphthalene sulfonate, alkylbenzene sulfonate, alkyl sulfonate, or ethylene oxide adducts of alkylphenols, or mixtures thereof.

[0131] Typical organic solvents that can be used when preparing solutions from solid ascaloside compositions include xylene, aromatic fractions such as propylbenzene fraction; or mixed naphthalene fraction, mineral oil, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkylamides of various fatty acids, in particular dimethylamide of fatty glycols, and glycol derivatives such as n-butyl ether, ethyl ether, or methyl ether of diethylene glycol, and methyl ether of triethylene glycol; amides of simple carboxylic acids such as dimethylformamide and dimethylacetamide; petroleum fraction or mineral oil; aromatic solvents; hydrocarbons such as paraffin oil; terpene solvents; rosin derivatives; aliphatic ketones such as cyclohexanone; complex aliphatic and aromatic alcohols such as 2-ethoxyethanol; soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, etc.; and esters of the above-mentioned vegetable oils. A mixture of two or more organic liquids may also be used in the preparation of the emulsifying concentrate. The organic liquids include xylene and propylbenzene fractions, with xylene being most preferred in some cases.

[0132] The “emulsifiers” for emulsifiable concentrates are typically mixed ionic and / or nonionic surfactants or their equivalents, such as those described herein. Examples of nonionic emulsifiers useful for the preparation of emulsifiable concentrates include polyalkylene glycol ethers, as well as ethoxylated alkylphenols and carboxylic acid esters solubilized with alkylphenols and arylphenols, aliphatic alcohols, aliphatic amines or fatty acids and ethylene oxide, propylene oxide, e.g., polyols or polyoxyalkylenes. Cationic emulsifiers include quaternary ammonium compounds and aliphatic amine salts. Anionic emulsifiers include oil-soluble salts of alkylarylsulfonic acids (e.g., calcium), oil-soluble salts of sulfated polyglycol ethers, and suitable salts of phosphorylated polyglycol ethers.

[0133] The compositions described herein may contain one or more inert carriers. Examples of inert carriers include, but are not limited to, prophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, and refined silicates.

[0134] An aqueous suspension can be prepared from a solid ascaloside composition when the composition is dispersed in an aqueous vehicle at a concentration typically ranging from about 5% to about 50% by weight. The suspension is prepared by finely grinding the solid ascaloside composition and vigorously mixing it with water, a surfactant, and a dispersant vehicle. Inert components such as inorganic salts and synthetic or natural gums may also be used to increase the density and / or viscosity of the aqueous vehicle, as desired.

[0135] In some embodiments, the present disclosure relates to a method for preparing an ascaloside composition ready for use, To provide solid ascaoside compositions as defined and described above and herein, The solid ascaloside composition is combined with a liquid solvent (e.g., water) at a first concentration, This includes further adding a liquid solvent (e.g., water), A method is provided in which a solid ascaloside composition comprises one or more ascalosides in an amount of 20% by weight or less.

[0136] In some embodiments, the present disclosure relates to a method for preparing an ascaloside composition ready for use, To provide solid ascaoside compositions as defined and described above and herein, This method involves combining a solid ascaloside composition with a liquid solvent (e.g., water) at a first concentration, A method is provided in which a solid ascaloside composition contains one or more ascalosides in an amount of 0.2% by weight or less. [Examples]

[0137] Example 1. Formation and Use of Solid Particulate Ascaloside Composition for Agricultural Use: A solid ascaloside composition consisting of ascr#18 sodium bicarbonate was formulated by combining 10 grams of ascaloside as a fine powder with 70 grams of sodium bicarbonate as a fine powder. The mixture was placed in an industrial blender and homogenized for 1 minute. The resulting powder was packaged in a polyethylene bottle containing a measuring cup (e.g., a shovel) with a volume of 1 tablespoon (15 mL). For field use, the measuring cup is used to measure 1 level shovel of solid ascaloside composition, which is dissolved in 1 gallon (3.8 L) of water to form a concentrated solution. This concentrated solution is added to a spray tank at a ratio of 2 fluid ounces per acre of crop to be treated. 1 gallon of the solution treats 64 acres of crop, resulting in an effective application ratio of approximately 25 mg of ascr#18 per acre.

[0138] Example 2. Formulation and Use of Alternative Solid Particulate Ascaloside Composition for Agriculture: A solid ascaloside composition consisting of ascr#18 and potassium bicarbonate was formulated by combining 100 grams of ascaloside as a fine powder with 700 grams of potassium bicarbonate as a fine powder. The mixture was placed in an industrial blender and homogenized for 1 minute. The resulting powder was packaged in a polyethylene bottle containing a measuring cup (e.g., a shovel) with a volume of 1 tablespoon (15 mL). For field use, the measuring cup is used to measure 1 level shovel of solid ascaloside composition, which is dissolved in 1 gallon (3.8 L) of water to form a concentrated solution. This concentrated solution is added to a spray tank at a ratio of 2 fluid ounces per acre of crop to be treated. 1 gallon of the solution treats 64 acres of crop, resulting in an effective application ratio of approximately 25 mg of ascr#18 per acre. This formulation also delivers a small amount of potassium nutrients to the treated crop.

[0139] Example 2b. Formulation and Use of Alternative Solid Microparticle Ascaloside Composition for Agriculture: The mixture was formed as described in Example 2, except that potassium bicarbonate was replaced with a commercially available formulation of potassium bicarbonate (MilStop® SP) containing additional components such as an anticoagulant and a surfactant. The product of Example 2 tended to aggregate into solid lumps that were difficult to remove from the packaging and difficult to measure accurately. In contrast, the product of Example 2b remained a free-flowing powder that was convenient for measurement and dissolution.

[0140] Example 3. Comparative solubility of pure ascaloside and the provided solid ascaloside composition: Two 1-gallon plastic containers were filled 1 / 3 full with clean tap water. One scoop of the composition described in Example 1 was added to the first container. The solid sank to the bottom of the container and dissolved within 30 seconds of gentle mixing with a polyethylene paddle. 1.5 g of pure ascr#18 powder was added to the second container, and some of the ascaloside floated on the surface of the water as fine particles, while some formed clumps. Mixing resulted in slow dissolution after vigorous mixing for several minutes, and the solid was still visible, with some of the ascaloside adhering to the sides of the container and the polyethylene paddle at the water level. Additional clean water was then added to each container until it reached 1 gallon. The solution from the provided solid formulation remained clear and colorless, with no visible solid present. The solution from the direct addition of ascaloside still contained a visible solid at the bottom of the container and adhering to the sides.

[0141] Example 4. Comparative stability of solutions from pure ascaloside or the provided solid ascaloside composition: 100 mL of the 1-gallon concentrate produced in Example 1, and 100 mL of a comparative concentrate produced by dissolving 1.5 g of pure ascaloside in 1 gallon of sterile water were placed in polyethylene bottles and contaminated with fungal spores. The containers were covered and left at room temperature for 4 weeks. The solution from the solid ascaloside composition showed no change in appearance or evidence of fungal growth, while the solution from ascaloside was cloudy and contained visible fungal growth suspended therein.

[0142] Example 5. Formation and Use of Ascaloside Tablet Composition for Agricultural Use: A solid ascaloside composition consisting of ascr#18 and potassium bicarbonate is formulated by combining 100 grams of ascaloside as a fine powder with 850 grams of potassium bicarbonate as a fine powder. The mixture is placed in an industrial blender and homogenized for 1 minute. Then, 50 grams of polyvinylpyrrolidone is added to the blender and the mixture is further homogenized for 30 seconds. The resulting mixture is divided into 5 g portions. Each portion is then formed into tablets using a high-pressure press with appropriate molds and punches. The resulting tablets are placed in polyethylene bottles for storage. For field use, one tablet is placed in one quart of water and stirred until dissolved. The concentrate of this quart is added to a spray tank for application to a 20-acre crop. Each tablet is used to treat a 20-acre crop to deliver an effective application ratio of 25 mg of ascr#18 per acre, or an effective application ratio of 50 mg / acre to a 10-acre crop. This formulation also delivers small amounts of potassium nutrients to the treated crops.

[0143] Example 6. In another example, a desired application ratio of 25 mg of ascaloside per acre is preferred. To treat 160 acres at this application ratio, 4000 mg (4 g) of ascaloside is required. An ascaloside microparticle composition containing 20% ​​ascaloside / 80% microparticle carrier composition is prepared by mixing 4 g of ascr#18 and 50 g of sodium bicarbonate (NaHCO3). The additional bulk of microparticle carrier makes it easier for the user to measure the composition while reducing transportation costs associated with shipping volume or water. The use of sodium bicarbonate in the microparticle carrier composition helps dissolve ascr#18 because this ascaloside has higher solubility in alkaline solutions.

[0144] Example 7. Formulation and Use of Solid Ascaloside Microparticle Composition for Residential Use: A solid ascaloside composition consisting of ascr#18 and potassium bicarbonate was formulated by combining 32 milligrams of ascaloside as a fine powder with 500 grams of potassium bicarbonate as a fine powder. The mixture was placed in an industrial blender and homogenized for 5 minutes. Ten 0.10 g samples were taken from the mixture, stirring between each sample to ensure that the sample represented the bulk composition. The samples were dissolved in water and analyzed by HPLC-MS, and it was found that they contained a consistent amount of ascaloside indicating that the solid mixture was homogeneous. The resulting powder was then packaged in a polyethylene bottle containing a measuring cup (e.g., a scoop) with a volume of 1 tablespoon (15 mL). For use, the measuring cup was used to measure 1 level scoop of solid ascaloside composition, which was dissolved in 1 gallon (3.8 L) of water to form a solution ready for spraying. This solution has an ascaloside concentration of approximately 1 micromol / liter, a concentration that is effective for pathogen control in most plants tested.

[0145] definition To facilitate understanding of this disclosure, certain terms are defined below. Additional definitions of the terms below and other terms are provided throughout this specification. In this application, unless otherwise clearly stated in context, the term “one (a)” may be understood to mean “at least one.”

[0146] As used in this application, the term "or" may be understood to mean "and / or". As used in this application, the terms "comprising" and "including" may be understood to encompass the itemized component or step, whether indicated by itself or with one or more additional components or steps. As used in this application, the term "comprise" and its variations, such as "comprising" and "comprises," are not intended to exclude other appendices, components, elements, or steps.

[0147] Approximately, roughly: Where used herein, the terms “approximately” and “roughly” are used interchangeably. Unless otherwise specified, the terms “approximately” and “roughly” can be understood to allow for standard variation, as understood by those skilled in the art. Where ranges are provided herein, they include the endpoints. Any figures used in this application, with or without “approximately,” are intended to cover any normal variation as understood by those skilled in the art. Unless otherwise specified, the above terms refer to within 25 percent of a given value. In some embodiments, the terms “approximately” or “about” refer to a range of values ​​that fall within 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, or less in either direction (greater than or less than) of a given standard reference value, unless otherwise specified or the context makes clear (except when such a number exceeds 100% of the possible value).

[0148] 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 version, Handbook of Chemistry and Physics, 75th Ed., inside cover, and specific functional groups are generally defined as described therein. In addition, general principles of organic chemistry, as well as specific functional parts and reactivity, are described in 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; and Carruthers, Some Modern Methods of Organic Synthesis, 3rd Edition, Cambridge University Press, Cambridge, 1987, the entire contents of each of which are incorporated herein by reference.

[0149] Certain compounds provided herein may contain one or more chiral centers and therefore may exist in various stereoisomeric forms, such as enantiomers and / or diastereomers. Accordingly, the compounds of the present invention and their compositions may be in the form of individual enantiomers, diastereomers or geometric isomers, or in the form of mixtures of stereoisomers. In certain embodiments, the compounds described herein are enanthopureous compounds. In certain other embodiments, mixtures of enantiomers or diastereomers are provided.

[0150] Furthermore, certain compounds described herein may have one or more double bonds that can exist as either Z or E isomers unless otherwise indicated. Compounds can be provided as individual isomers substantially free of other isomers, and alternatively, as mixtures of various isomers, for example, as a racemic mixture of enantiomers.

[0151] As used herein, the term “isomer” includes any and all geometric isomers and stereoisomers. For example, “isomer” includes cis and trans isomers, E and Z isomers, R and S isomers, diastereomers, (D)-isomers, (L)-isomers, racemic mixtures thereof, and other mixtures thereof, as is within the scope of this disclosure. For example, in some embodiments, a compound may be provided substantially free of one or more corresponding stereoisomers and may be referred to as “stereochemically concentrated.”

[0152] Where a particular enantiomer is preferred, in some embodiments the compound may be provided substantially without the opposite enantiomer, and may be referred to as “optically concentrated.” As used herein, “optically concentrated” means that the compound of the present invention is composed of a significantly higher proportion of one enantiomer. In some particular embodiments, the compound is composed of at least about 90% by weight of one enantiomer. In some embodiments, the compound is composed of at least about 95% by weight, 97% by weight, 98% by weight, 99% by weight, 99.5% by weight, 99.7% by weight, 99.8% by weight, or 99.9% by weight of one enantiomer. In some embodiments, the enantiomer excess of the compound provided is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9%. In some embodiments, enantiomers may be separated from the racemic mixture by any known method such as chiral high-performance liquid chromatography (HPLC) and the formation and crystallization of chiral salts, or they may be prepared by asymmetric synthesis. 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, NY, 1962), and Wilen, SH, Tables of Resolving Agents and Optical Resolutions p.268 (ELEliel, Ed., Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0153] As used herein, the terms "halo" and "halogen" refer to an atom selected from fluorine (fluoro, -F), chlorine (chloro, -Cl), bromine (bromo, -Br), and iodine (iodo, -I).

[0154] As used herein, the terms “aliphatic” or “aliphatic group” refer to a hydrocarbon moiety that may be linear (i.e., unbranched), branched, or cyclic (including condensed, cross-linked, and spiro-condensed polycyclic), and may be fully saturated or contain one or more unsaturated units, but is not aromatic. Unless otherwise specified, an aliphatic group contains 1 to 30 carbon atoms. In certain embodiments, an aliphatic group contains 1 to 12 carbon atoms. In certain embodiments, an aliphatic group contains 1 to 8 carbon atoms. In certain embodiments, an aliphatic group contains 1 to 6 carbon atoms. In some embodiments, an aliphatic group contains 1 to 5 carbon atoms, in some embodiments, an aliphatic group contains 1 to 4 carbon atoms, in yet another embodiment, an aliphatic group contains 1 to 3 carbon atoms, and in yet another embodiment, an 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, as well as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl hybrids thereof.

[0155] As used herein, the terms “heteroaliphatic” or “heteroaliphatic group” refer 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 heterocyclyl group.

[0156] As used herein, the term “unsaturated” means that a part has one or more double or triple bonds.

[0157] As used herein, the term “alkyl” refers to a saturated, linear, or branched hydrocarbon radical derived from an aliphatic moiety containing 1 to 6 carbon atoms by the removal of a single hydrogen atom. Unless otherwise specified, alkyl groups contain 1 to 12 carbon atoms. In certain embodiments, alkyl groups contain 1 to 8 carbon atoms. In certain embodiments, alkyl groups contain 1 to 6 carbon atoms. In some embodiments, alkyl groups contain 1 to 5 carbon atoms, in some embodiments, alkyl groups contain 1 to 4 carbon atoms, in yet another embodiment, alkyl groups contain 1 to 3 carbon atoms, and in yet another embodiment, alkyl groups contain 1 to 2 carbon atoms. Examples of alkyl radicals include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, sec-pentyl, iso-pentyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, n-decyl, n-undecyl, and dodecyl.

[0158] As used herein, the term “alkenyl” refers to a monovalent group derived from a linear or branched aliphatic moiety having at least one carbon-carbon double bond by the removal of a single hydrogen atom. Unless otherwise specified, alkenyl groups contain 2 to 12 carbon atoms. In certain embodiments, alkenyl groups contain 2 to 8 carbon atoms. In certain embodiments, alkenyl groups contain 2 to 6 carbon atoms. In some embodiments, alkenyl groups contain 2 to 5 carbon atoms, in some embodiments, alkenyl groups contain 2 to 4 carbon atoms, in yet another embodiment, alkenyl groups contain 2 to 3 carbon atoms, and in yet another embodiment, alkenyl groups contain 2 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, butenyl, and 1-methyl-2-buten-1-yl.

[0159] The term “aryl,” used alone or as part of a larger term, such as “aralkyl,” “aralkoxy,” or “aryloxyalkyl,” refers to monocyclic and polycyclic ring systems having a total of 5 to 20 ring members, where at least one ring in the system is aromatic, and each ring in the system contains 3 to 12 ring members. The term “aryl” may be used interchangeably with the term “aryl ring.” In certain embodiments, “aryl” refers to aromatic ring systems, including but not limited to phenyl, biphenyl, naphthyl, and anthrasyl, which may have one or more substituents. The scope of the term “aryl” as used herein also includes groups into which the aromatic ring is condensed with one or more additional rings, such as benzofuranyl, indanyl, phthalimidyl, naphthoimidyl, phenantridinyl, or tetrahydronaphthyl.

[0160] The terms "heteroaryl" and "heteroar-" used alone or as part of a larger phrase, such as "heteroaralkyl" or "heteroaralkoxy," refer to a group having 5 to 10 ring atoms, preferably 5, 6, or 9 ring atoms, sharing 6, 10, or 14 π electrons within the cyclic arrangement, and having 1 to 5 heteroatoms in addition to carbon atoms. 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, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, indolidinyl, prinyl, naphthilidinyl, and pteridinyl. As used herein, the terms “heteroaryl” and “hetero-” also include groups in which a heteroaromatic ring is condensed with one or more aryl, alicyclic, or heterocyclyl rings, and the radical or bond site is located on the heteroaromatic ring. Non-limiting examples include indolyl, isoindolyl, benzothienyl, benzofuranyl, dibenzofuranyl, indazolyl, benzimidazolyl, benzthiazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 4H-quinolidinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, and pyrido[2,3-b]-1,4-oxazine-3(4H)-one. Heteroaryl groups can be monocyclic, bicyclic, bridging bicyclic, or spirocyclic. The term "heteroaryl" may be used interchangeably with the terms "heteroaryl ring," "heteroaryl group," or "heteroaromatic," any of which may include a optionally substituted ring. The term "heteroaralkyl" refers to an alkyl group substituted with a heteroaryl group, where the alkyl and heteroaryl moieties are independently and optionally substituted.The term "heteroarylenyl" refers to a divalent heteroaryl group (e.g., pyridylenyl).

[0161] As used herein, the terms “heterocycle,” “heterocyclyl,” “heterocyclic radical,” and “heterocyclic ring” are used interchangeably and refer to stable 5-7 member monocyclic or 7-10 member bicyclic heterocyclic moieties having one or more, preferably 1-4, heteroatoms in addition to the carbon atom, as defined above, and being either saturated or partially unsaturated. When used in relation to the ring atoms of a heterocycle, the term “nitrogen” includes substituted nitrogen. For example, in a saturated or partially unsaturated ring having 0-3 heteroatoms selected from oxygen, sulfur, or nitrogen, the nitrogen may be N (as in 3,4-dihydro-2H-pyrrolyl), NH (as in pyrrolidinyl), or +NR (as in N-substituted pyrrolidinyl).

[0162] A heterocyclic ring can be bonded to its pendant group with any heteroatom or carbon atom that results in a stable structure, and any of the ring atoms can be optionally substituted. Examples of such saturated or partially unsaturated heterocyclic radicals include, but are not limited to, tetrahydrofuranyl, tetrahydrothiophenylpyrrolidinyl, piperidinyl, pyrrolinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl, oxazolidinyl, piperazinyl, dioxanyl, dioxolanyl, diazepinyl, oxazepinyl, thiazepinyl, morpholinyl, and quinuclidinyl. The terms “heterocyclic ring,” “heterocyclyl,” “heterocyclyl ring,” “heterocyclic group,” “heterocyclic moiety,” and “heterocyclic radical” are used interchangeably herein and also include groups in which a heterocyclyl ring is fused to one or more aryl, heteroaryl, or alicyclic rings, such as indolinyl, 3H-indolyl, chromanyl, phenantridinyl, or tetrahydroquinolinyl. In some embodiments, the heterocycle may be a 5- to 12-membered bicyclic, bridging bicyclic, or spirocyclic ring. The heterocycle may contain one or more oxo (=O) or thioxo (=S) substituents. The term "heterocyclylalkyl" refers to an alkyl group substituted with a heterocyclyl, where the alkyl and heterocyclyl moieties are independently and optionally substituted.

[0163] 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 encompass rings having multiple unsaturated moies, but not to include aryl or heteroaryl moies as defined herein.

[0164] As described herein, the compounds provided herein may contain “optionally substituted” moieties. Generally, the term “substituted” means that one or more hydrogens of a designated moiety are replaced with preferred substituents, whether or not the term “optionally” precedes it. Unless otherwise indicated, an “optionally substituted” group may have preferred substituents at each substituted position of the group, and if more than one position in any given structure can be replaced with more than one substituent selected from a particular group, the substituents may be the same at all positions or different at all positions. The assumed substituent combinations preferably result in the formation of a stable or chemically feasible compound. The term “stable,” as used herein, means a compound that remains substantially unchanged when placed under conditions that enable their production, detection, and, in certain embodiments, their recovery, purification, and use in one or more of the purposes disclosed herein.

[0165] Suitable monovalent substituents on the replaceable carbon atoms of the "optionally substituted" group are, independently, halogens, -(CH2) 0-4 R°, -(CH2) 0-4 OR°, -O-(CH2) 0-4 C(O)OR°, -(CH2) 0-4 CH(OR°)2, -(CH2) 0-4 -(CH2) can be substituted with SR° and R°. 0-4 (CH2) can be substituted with pH and R°. 0-4 O(CH2) 0-1 -CH=CHPh, -NO2, -CN, -N3, -(CH2) can be substituted with Ph and R°. 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) 0-4C(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) 0-4 S(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 alkylenes)ON(R°)2, or -(C 1-4 The linear or branched alkylene is C(O)ON(R°)2, where each R° can be substituted as defined below, independently of hydrogen, C 1-8 Aliphatic, -CH2Ph, -O(CH2) 0-1 A 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or, notwithstanding the above definition, a 3-12 member saturated, partially unsaturated, or aryl monocyclic or polycyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, which together with their intervening atom(s) may be substituted as defined below.

[0166] The intervening atoms along with the preferred monovalent substituents of R° are, independently, halogens, -(CH2) 0-2 R ● ,-(HaroR ● ), -(CH2) 0-2 OH, -(CH2) 0-2 Ure ● ,-(CH2) 0-2 CH(OR ● )2, -O(HaroR ● ), -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 Linear or branched alkylene)C(O)OR ● , or -SSR ● And each R ● It is either unsubstituted, or if preceded by "halo", it is substituted by only one or more halogens and independently, C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1 The R° saturated, partially unsaturated, or aryl ring is selected from 5-6 membered saturated, partially unsaturated, or rings having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Preferred divalent substituents on the saturated carbon atom of R° include =O and =S.

[0167] Suitable divalent substituents on the saturated carbon atom of the "optionally substituted" group are, =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)) 2-3 S- was mentioned, R * Each independent occurrence of C can be substituted with hydrogen, as defined below. 1-6 Selected from an aliphatic, or unsubstituted 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. A suitable divalent substituent to bond to the substituted carbon proximal to the "optionally substituted" group is -O(CR * 2) 2-3 O- is mentioned, R * Each independent occurrence of C can be substituted with hydrogen, as defined below. 1-6 Selected from aliphatic, or unsubstituted 5-6 member saturated, partially unsaturated, or aryl rings having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0168] R * Suitable substituents on the aliphatic group include halogens, -R ● ,-(HaroR ● ), -OH, -OR ● ,-O(HaroR ● ), -CN, -C(O)OH, -C(O)OR ● -NH2, -NHR ● , -NR ● 2, or -NO2 is included, each R ● It is either unsubstituted, or if preceded by "halo", it is substituted by only one or more halogens and independently, C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1 It is a 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from pH, nitrogen, oxygen, or sulfur.

[0169] A suitable substituent on the substituted nitrogen of the "optionally substituted" group is -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 † These are listed, and each R † C can be substituted independently of hydrogen, as defined below. 1-6 Aliphatic, unsubstituted-OPh, or unsubstituted 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or notwithstanding the above definition, R † The two independent occurrences, together with their intervening atom(s), form an unsubstituted 3-12 member saturated, partially unsaturated, or aryl monocyclic or bicyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0170] R † Suitable substituents on the aliphatic group are, independently, halogens, -R ● ,-(HaroR ● ), -OH, -OR ● ,-O(HaroR ● ), -CN, -C(O)OH, -C(O)OR ● -NH2, -NHR ● , -NR ● 2, or -NO2, and each R ● If it is unsubstituted, or if preceded by "halo", it is substituted by only one or more halogens, independently, C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1It is a 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from pH, nitrogen, oxygen, or sulfur.

[0171] As used herein, the term “substantially” refers to a qualitative state indicating the whole or nearly whole range or degree of the desired feature or characteristic.

[0172] There is a convention to name ascalosides with a prefix of several letters followed by a pound sign (#) 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 is associated with a specific chemical structure of a known composition and will immediately understand the structure of the molecule indicated using this nomenclature. Unless otherwise indicated, all compound identifiers of this form used herein conform to the definitions listed in the C. elegans Small Molecule Identifier Database (SMID-DB), maintained at smid-db.org on the World Wide Web.

[0173] Embodiments of the present invention include the following: 1. An ascaloside composition comprising one or more ascalosides and a soluble solid carrier composition, wherein the ascaloside composition contains 20% by weight or less of the one or more ascalosides. 2. The composition according to Embodiment 1, wherein the ascaloside composition comprises 1% to 20% by weight of one or more ascalosides. 3. The one or more ascalosides include an ascaloside having structure (I), [ka] During the ceremony, Z is replaced by C of any choice. 3-40 It is an aliphatic group, R a and R b Each of these independently corresponds to -H or C 1-20 aliphatic, C 1-20 Ashiru, C1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bond functional group, sulfur bond functional group, silicon bond functional group, C 2-20 Carbonate (e.g., partial C(O)OR) c ), C 2-20 Carbamates (e.g., partial-C(O)N(R) c )2), C 2-20 Thioesters (e.g., partial-C(S)R) c ), C 2-20 Thiocarbonates (e.g., partial-C(S)OR c ), C 2-20 Dithiocarbonates (e.g., partial-C(S)SR) c ), C 1-20 Thiocarbamates (e.g., partial-C(S)N(R) c )2) A portion that is optionally substituted from the group consisting of a sugar portion, a peptide, a polymer chain, or bond to another ascaloside molecule or linkage via a carbon-containing linker portion, R c However, in each occurrence, independently, -H and C are substituted by any choice. 1-12 Aliphatic, C substituted by choice 1-12 Selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain, or linkage to another ascaloside molecule or via a carbon-containing linker moiety, R a and R b The composition according to Embodiment 1 or 2, wherein together they can form an optionally substituted ring that optionally contains one or more heteroatoms and optionally contains one or more unsaturated moieties. 4.Z is, i.-CH(CH3)-R 1 (R 1 This is C, which has been replaced by an optional substitution. 1-40 (It is an aliphatic group.) ii.-CH(CH3)-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20(Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), iii.-CH(CH3)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), iv.-CH(CH3)-(CH2) n -CH(OH)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), v.-CH(CH3)-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), vi.-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), vii.-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), viii.-(CH2) n -CH(OH)-CH2-CO2R2 (n is an integer from 1 to 40, R 2 C is a -H, a 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 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 The composition according to Embodiment 3, selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 5.Z is, (x)-CH(CH3)-(CH2) n -CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xi)-CH(CH3)-(CH2) n -CH=CH-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xii)-CH(CH3)-(CH2) n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xiii)-CH(CH3)-(CH2) n -C(O)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xiv)-(CH2) n -CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xv)-(CH2) n -CH=CH-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xvi)-(CH2)n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety, or (xvii)-(CH2) n -C(O)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 The composition according to Embodiment 3, selected from the group consisting of a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another askaloside molecule via a carbon-containing linker moiety. 6.R a and R b The composition according to any one of Embodiments 3 to 5, wherein each of them is -H. 7. Z is -CH(CH3)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 However, C is substituted with -H, a metal cation, or optionally. 1-20 A composition according to any one of Embodiments 3 to 6, comprising an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 8. The composition according to any one of Embodiments 1 to 7, wherein the at least one ascaloside comprises an ascaloside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. 9. The composition according to any one of Embodiments 1 to 8, wherein the at least one ascaloside comprises ascr#18. 10. The composition according to any one of Embodiments 1 to 9, wherein the at least one ascaloside is an ascaloside salt. 11. The composition according to any one of Embodiments 1 to 10, wherein the carrier composition comprises a water-soluble filler. 12. The composition according to Embodiment 11, wherein the water-soluble filler is a carbohydrate. 13. The composition according to Embodiment 12, wherein the carbohydrate water-soluble filler is selected from the group consisting of lactose, glucose, fructose, mannose, mannitol, sucrose, powdered sugar, black sugar, brown sugar, soft brown sugar, microcrystalline cellulose, starch, and powdered cellulose. 14. The composition according to Embodiment 11, wherein the water-soluble filler is a neutral inorganic salt. 15. The composition according to Embodiment 14, wherein the inorganic salt is calcium nitrate, calcium chloride, copper(II) phosphate, copper(I) chloride, copper(II) carbonate, copper(I) iodide, iron(II) molybdate, potassium sulfate, potassium bromide, potassium chloride, potassium nitrate, magnesium nitrate, magnesium chloride, magnesium sulfate, sodium sulfate, sodium chloride, sodium nitrite, and sodium nitrate. 16. The composition according to Embodiment 11, wherein the water-soluble filler is polyethylene glycol. 17. The composition according to Embodiment 16, wherein the polyethylene glycol has an average molecular weight of 3000 to 8000. 18. The composition according to Embodiments 1 to 17, wherein the particulate carrier composition comprises one or more pH adjusting agents. 19. The composition according to Embodiment 18, wherein the pH adjusting agent reduces the pH of the aqueous solution when dissolved in water. 20. The composition according to Embodiment 19, wherein the pH adjusting agent is selected from the group consisting of ammonium sulfate, calcium dihydrogen phosphate, copper(II) nitrate, copper(II) bromide, copper(II) chloride, copper(II) sulfate, boric acid, potassium dihydrogen phosphate, sodium sulfite, sodium dihydrogen phosphate, sodium bisulfite, sodium bisulfite, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium bisulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide. 21. The composition according to Embodiment 18, wherein the pH adjusting agent increases the pH of the aqueous solution when dissolved in water. 22. The composition according to Embodiment 21, wherein the pH adjusting agent is selected from the group consisting of ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium bicarbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium bicarbonate, potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium bicarbonate, sodium hydroxide, sodium hydroxide, ammonium bicarbonate, zinc hydroxide, and zinc carbonate. 23. The composition according to any one of Embodiments 1 to 22, wherein the ascaloside microparticle composition comprises one or more ascalosides and one or more carbonate salts. 24. The composition according to any one of Embodiments 1 to 22, wherein the particulate carrier composition comprises one or more water-soluble fillers and one or more pH adjusters. 25. The composition according to Embodiment 1, wherein the particulate composition essentially consists of one or more ascalosides and one or more carbonate salts. 26. A method of treating a crop or plant with one or more ascalosides, wherein the method is To obtain a soluble solid ascaloside composition comprising one or more ascalosides and a soluble solid carrier composition, wherein the ascaloside composition contains 20% by weight or less of the one or more ascalosides, The ascaloside composition is mixed with water to form an ascaloside solution, A method comprising applying the ascaloside solution to the crop or plant. 27. The method according to Embodiment 26, wherein the particulate composition is mixed with about 2 L to about 10 L of water. 28. The method according to Embodiment 26 or 27, wherein the particulate composition is placed in a container before being mixed with water. 29. The method according to any one of embodiments 26 to 28, wherein the concentration of the one or more ascalosides in the water is about 0.5 mM to about 2 mM after mixing. 30. The method according to any one of embodiments 26 to 29, wherein the ascaloside microparticle composition is mixed with water to form a concentrated solution, and the method further comprises diluting the concentrated solution with water to form a diluted solution. 31. The method according to Embodiment 30, wherein the diluted solution is applied to the crop or plant. 32. The method according to any one of Embodiments 26 to 31, wherein the ascaloside composition comprises 1% to 20% by weight of one or more ascalosides. 33. The one or more ascalosides include an ascaloside having structure (I), [ka] During the ceremony, Z is replaced by C of any choice. 3-40 It is an aliphatic group, R a and R b Each of these independently corresponds to -H or C 1-20 aliphatic, C 1-20 Ashiru, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bond functional group, sulfur bond functional group, silicon bond functional group, C 2-20Carbonate (e.g., partial C(O)OR) c ), C 2-20 Carbamates (e.g., partial-C(O)N(R) c )2), C 2-20 Thioesters (e.g., partial-C(S)R) c ), C 2-20 Thiocarbonates (e.g., partial-C(S)OR c ), C 2-20 Dithiocarbonates (e.g., partial-C(S)SR) c ), C 1-20 Thiocarbamates (e.g., partial-C(S)N(R) c )2) A portion that is optionally substituted from the group consisting of a sugar portion, a peptide, a polymer chain, or bond to another ascaloside molecule or linkage via a carbon-containing linker portion, R c However, in each occurrence, independently, -H and C are substituted by any choice. 1-12 Aliphatic, C substituted by choice 1-12 Selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain, or linkage to another ascaloside molecule or via a carbon-containing linker moiety, R a and R b The method according to any one of embodiments 26 to 32, wherein together they can form an optionally substituted ring that optionally contains one or more heteroatoms and optionally contains one or more unsaturated sites. 34.Z is, x.-CH(CH3)-R 1 (R 1 This is C, which has been replaced by an optional substitution. 1-40 (It is an aliphatic group.) xi.-CH(CH3)-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), xii.-CH(CH3)-(CH2) n-CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), xiii.-CH(CH3)-(CH2) n -CH(OH)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), xiv.-CH(CH3)-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), xv.-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), xvi.-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), xvii.-(CH2) n -CH(OH)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20(Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides), and xviii.-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 The method according to Embodiment 33, selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 35.Z is, (x)-CH(CH3)-(CH2) n -CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xi)-CH(CH3)-(CH2) n -CH=CH-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xii)-CH(CH3)-(CH2) n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20(This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xiii)-CH(CH3)-(CH2) n -C(O)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xiv)-(CH2) n -CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xv)-(CH2) n -CH=CH-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xvi)-(CH2) n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety, or (xvii)-(CH2) n -C(O)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 The composition according to Embodiment 32, selected from the group consisting of a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another askaloside molecule via a carbon-containing linker moiety. 36.R a and R b The method according to any one of embodiments 33 to 35, wherein each is -H. 37.Z is -CH(CH3)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 However, C is substituted with -H, a metal cation, or optionally. 1-20 The method according to any one of embodiments 33 to 36, wherein the aliphatic group is an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 38. The method according to any one of embodiments 26 to 37, wherein the at least one ascaloside comprises an ascaloside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. 39. The method according to any one of embodiments 26 to 38, wherein the at least one ascaloside comprises ascr#18. 40. The method according to any one of embodiments 26 to 39, wherein the at least one ascaloside is an ascaloside salt. 41. The method according to any one of Embodiments 26 to 40, wherein the particulate carrier composition comprises a water-soluble filler. 42. The method according to Embodiment 41, wherein the water-soluble filler is a carbohydrate. 43. The method according to Embodiment 42, wherein the carbohydrate water-soluble filler is selected from the group consisting of lactose, glucose, fructose, mannose, mannitol, sucrose, powdered sugar, black sugar, brown sugar, soft brown sugar, microcrystalline cellulose, starch, and powdered cellulose. 44. The method according to Embodiment 41, wherein the water-soluble filler is a neutral inorganic salt. 45. The method according to Embodiment 44, wherein the inorganic salt is calcium nitrate, calcium chloride, copper(II) phosphate, copper(I) chloride, copper(II) carbonate, copper(I) iodide, iron(II) molybdate, potassium sulfate, potassium bromide, potassium chloride, potassium nitrate, magnesium nitrate, magnesium chloride, magnesium sulfate, sodium sulfate, sodium chloride, sodium nitrite, and sodium nitrate. 46. ​​The method according to Embodiment 41, wherein the water-soluble filler is polyethylene glycol. 47. The method according to Embodiment 46, wherein the polyethylene glycol has an average molecular weight of 3000 to 8000. 48. The method according to Embodiments 26 to 47, wherein the particulate carrier composition comprises one or more pH adjusting agents. 49. The method according to Embodiment 48, wherein the pH adjusting agent reduces the pH of the aqueous solution when dissolved in water. 50. The method according to Embodiment 49, wherein the pH adjusting agent is selected from the group consisting of ammonium sulfate, calcium dihydrogen phosphate, copper(II) nitrate, copper(II) bromide, copper(II) chloride, copper(II) sulfate, boric acid, potassium dihydrogen phosphate, sodium sulfite, sodium dihydrogen phosphate, sodium bisulfite, sodium bisulfite, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium bisulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide. 51. The method according to Embodiment 48, wherein the pH adjusting agent increases the pH of the aqueous solution when dissolved in water. 52. The method according to Embodiment 51, wherein the pH adjusting agent is selected from the group consisting of ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium bicarbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium bicarbonate, potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), trisodium phosphate, sodium bicarbonate, sodium hydroxide, ammonium bicarbonate, zinc hydroxide, and zinc carbonate. 53. The method according to any one of Embodiments 26 to 52, wherein the ascaloside microparticle composition comprises one or more ascalosides and one or more carbonate salts. 54. The method according to any one of embodiments 26 to 53, wherein the particulate carrier composition comprises one or more water-soluble fillers and one or more pH adjusters. 55. The method according to Embodiment 26, wherein the particulate composition essentially consists of one or more ascalosides and one or more carbonate salts. 56. An ascaloside composition comprising one or more ascalosides and a solid soluble carrier composition, wherein the ascaloside composition contains 0.2% by weight or less of the one or more ascalosides. 57. The composition of embodiment 56, wherein the ascarylose composition comprises 0.005 wt% to 0.2 wt% of said one or more ascarylosides. 58. The one or more ascarylosides comprise an ascaryloside having structure (I),

Chemical Structure

[0174] The compounds, compositions, and methods of this application are intended to encompass modifications and adaptations developed using information from the embodiments described herein. Adaptations or modifications of the methods and processes described herein can be carried out by those skilled in the art.

[0175] The use of headings in this disclosure will be understood to be provided for the convenience of the reader. The presence and / or placement of headings is not intended to limit the scope of the subject matter described herein. Unless otherwise specified, embodiments located in one section of this application are applicable throughout this application, both individually and in combination, to other embodiments.

[0176] Throughout this description, where a composition, compound, or product is described as having, containing, or comprising a particular component, or where a process and method is described as having, containing, or comprising a particular step, in addition, it is intended that there exist articles, devices, and systems of this application which are essentially composed of or comprise the listed components, and that there exist processes and methods of this application which are essentially composed of or comprise the listed processing steps.

[0177] Please understand that the order of steps or sequences for performing a particular action is not important, as long as the described method is functional. Furthermore, two or more steps or actions can be performed simultaneously.

[0178] All publications and patent applications described herein are indicators of the level of skill of those skilled in the art in the field relating to the present invention. All publications and patent applications are incorporated herein by reference to the same extent as each individual publication or patent application is specifically and individually indicated as being incorporated by reference.

[0179] While the aforementioned invention is described in some detail as an illustration and example for the purpose of clarifying understanding, it will be apparent that certain modifications and alterations may be practiced within the scope of the attached claims.

Claims

1. An ascaloside composition comprising one or more ascalosides and a soluble solid carrier composition, wherein the ascaloside composition contains about 20% by weight or less of the one or more ascalosides.

2. The composition according to claim 1, wherein the ascaloside composition comprises about 1% by weight to about 20% by weight of one or more ascalosides.

3. The one or more ascalosides include an ascaloside having structure (I), 【Chemistry 23】 During the ceremony, Z is replaced by C of arbitrary choice. ３－４０ It is an aliphatic group, R ａ and R ｂ is each independently -H, or C １－２０ aliphatic, C １－２０ acyl, C １－２０ heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus-bonded functional group, sulfur-bonded functional group, silicon-bonded functional group, C ２－２０ carbonate (e.g., -moiety-C(O)OR ｃ ), C ２－２０ carbamate (e.g., -moiety-C(O)N(R ｃ ) ２ ), C ２－２０ thioester (e.g., moiety-C(S)R ｃ ), C ２－２０ thiocarbonate (e.g., moiety-C(S)OR ｃ ), C ２－２０ dithiocarbonate (e.g., moiety-C(S)SR ｃ ), C １－２０ thiocarbamate (e.g., moiety-C(S)N(R ｃ ) ２ ), an optionally substituted moiety selected from the group consisting of a sugar moiety, a peptide, a polymer chain, or a bond to another ascaroside molecule or a linkage via a carbon-containing linker moiety, and R ｃ at 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, a polymer chain, or a bond to another ascaroside molecule or a linkage via a carbon-containing linker moiety, and R ａ and R ｂ taken together may form an optionally substituted ring optionally containing one or more heteroatoms and optionally containing one or more sites of unsaturation, the composition according to claim 1 or 2.

4. Z is i. -CH(CH ３ )-R １ (R １ C is replaced by an optional substitution. １－４０ (It is an aliphatic group.) ii. -CH(CH ３ )-(CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) iii. -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) iv. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) v. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) vi. - (CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) vii. - (CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) viiii. - (CH ２ ) ｎ -CH(OH)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides), and ix. - (CH ２ ) ｎ -C(O)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ The composition according to claim 3, selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

5. Z is x. -CH(CH ３ )-(CH ２ ) ｎ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ is independently -H, optionally substituted C １－２０ aliphatic group, optionally substituted C １－２０ heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or a bond to another ascaroside molecule or a linkage via a carbon-containing linker moiety), xi.-CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ is independently -H, optionally substituted C １－２０ aliphatic group, optionally substituted C １－２０ heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or a bond to another ascaroside molecule or a linkage via a carbon-containing linker moiety), xii. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH ２ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xiii. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH ２ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xiv. - (CH ２ ) ｎ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xv. - (CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xvi. - (CH ２ ) ｎ -CH(OH)-CH ２ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xvii. - (CH ２ ) ｎ -C(O)-CH ２ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), or xviiii. A optionally unsaturated and optionally substituted C chain that terminates at a chain end containing a nitrogen-containing functional group, an oxygen-containing functional group, or a sulfur-containing functional group. ２－４０ The composition according to claim 3, selected from the group consisting of side chains.

6. The composition according to any one of claims 1 to 5, wherein one or more ascalosides comprises ascalosides selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24.

7. The composition according to any one of claims 1 to 6, wherein one or more ascalosides contain ascr#18.

8. The composition according to any one of claims 1 to 7, wherein the at least one ascaloside is an ascaloside salt.

9. The composition according to any one of claims 1 to 8, wherein the soluble solid carrier composition comprises a water-soluble filler.

10. The composition according to claims 1 to 9, wherein the soluble solid carrier composition comprises one or more pH adjusting agents.

11. The composition according to claim 10, wherein the pH adjusting agent increases the pH of the aqueous solution when dissolved in water.

12. The composition according to claim 11, wherein the pH adjusting agent is selected from the group consisting of ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium bicarbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium bicarbonate (potassium bicarbonate), potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium bicarbonate (sodium bicarbonate), sodium hydroxide, ammonium bicarbonate, zinc hydroxide, and zinc carbonate.

13. The composition according to any one of claims 1 to 11, wherein the ascaloside composition comprises one or more ascalosides and one or more carbonate salts (for example, sodium bicarbonate or potassium bicarbonate).

14. The composition according to any one of claims 1 to 13, wherein the ascaloside composition essentially consists of one or more ascalosides and one or more carbonate salts (e.g., sodium bicarbonate or potassium bicarbonate).

15. The composition according to any one of claims 1 to 14, characterized in that the composition has a solubility of at least 1, 3, 6, 9, 12, 15, 20, or 25 grams / gallon of water for one or more ascalosides.

16. The composition according to any one of claims 1 to 14, characterized in that the composition has one or more ascalosides exhibiting a solubility in water of at least 0.1, 1, 10, 50, or 100 mM.

17. The composition according to any one of claims 1 to 14, characterized in that the composition has one or more ascalosides that exhibit solubility in water at least 50%, 75%, 100%, 1,000%, 5,000%, or 10,000% higher than the reference.

18. The composition according to claim 17, wherein the reference is a corresponding composition containing only one or more ascalosides.

19. A method of treating a crop or plant with one or more ascalosides, wherein the method is To obtain the ascaloside composition described in any one of claims 1 to 18, The ascaloside composition is mixed with water to form an ascaloside solution, A method comprising applying the ascaloside solution to the crop or plant.

20. The method according to claim 19, wherein the ascaloside composition is mixed with about 2 L to about 10 L of water.

21. The method according to claim 19 or 20, wherein the concentration of one or more ascalosides in the water is about 0.5 mM to about 2 mM after mixing.

22. The method according to any one of claims 19 to 21, wherein the ascaloside composition is mixed with water to form a concentrated solution, and the method further comprises diluting the concentrated solution with water to form a diluted solution.

23. The method according to claim 22, wherein the diluted solution is applied to the crop or plant.

24. An ascaloside composition comprising one or more ascalosides and a solid soluble carrier composition, wherein the ascaloside composition contains 0.2% by weight or less of the one or more ascalosides.

25. The composition according to claim 24, wherein the ascaloside composition comprises about 0.005% by weight to about 0.05% by weight of one or more ascalosides.

26. The one or more ascalosides include an ascaloside having structure (I), 【Chemistry 24】 During the ceremony, Z is replaced by C of arbitrary choice. ３－４０ It is an aliphatic group, R ａ and R ｂ Each of these independently corresponds to -H or C １－２０ aliphatic, C １－２０ Ashiru, C １－２０ Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bond functional group, sulfur bond functional group, silicon bond functional group, C ２－２０ Carbonates (e.g., partial-C(O)OR) ｃ ), C ２－２０ Carbamates (e.g., partial-C(O)N(R) ｃ ) ２ ), C ２－２０ Thioesters (e.g., partial-C(S)R) ｃ ), C ２－２０ Thiocarbonates (e.g., partial-C(S)OR) ｃ ), C ２－２０ Dithiocarbonates (e.g., partial-C(S)SR) ｃ ), C １－２０ Thiocarbamates (e.g., partial-C(S)N(R) ｃ ) ２ ), a portion optionally substituted from the group consisting of a sugar portion, a peptide, a polymer chain, or bonding to another ascaloside molecule or linkage via a carbon-containing linker portion, R ｃ However, in each occurrence, independently, -H and C are substituted by any choice. １－１２ Aliphatic C, optionally substituted １－１２ Selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain, or linkage to another ascaloside molecule or via a carbon-containing linker moiety, R ａ and R ｂ The composition according to claim 24 or 25, wherein together they can form an optionally substituted ring that optionally contains one or more heteroatoms and optionally contains one or more unsaturated moieties.

27. Z is i. -CH(CH ３ )-R １ (R １ C is replaced by an optional substitution. １－４０ (It is an aliphatic group.) ii. -CH(CH ３ )-(CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) iii. -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) iv. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) v. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) vi. - (CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) vii. - (CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide) viiii. - (CH ２ ) ｎ -CH(OH)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ (Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides), and ix. - (CH ２ ) ｎ -C(O)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ The composition according to claim 26, selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

28. Z is x. -CH(CH ３ )-(CH ２ ) ｎ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xi. -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xii. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH ２ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xiii. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH ２ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xiv. - (CH ２ ) ｎ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xv. - (CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xvi. - (CH ２ ) ｎ -CH(OH)-CH ２ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xvii. - (CH ２ ) ｎ -C(O)-CH ２ -CON(R) ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic groups, optionally substituted C １－２０ (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), or xviiii. A optionally unsaturated and optionally substituted C chain that terminates at a chain end containing a nitrogen-containing functional group, an oxygen-containing functional group, or a sulfur-containing functional group. ２－４０ The composition according to claim 26, selected from the group consisting of side chains.

29. The composition according to any one of claims 24 to 28, wherein the at least one ascaloside comprises an ascaloside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24.

30. The composition according to any one of claims 24 to 29, wherein the at least one ascaloside comprises ascr#18.

31. The composition according to any one of claims 24 to 30, wherein the at least one ascaloside is an ascaloside salt.

32. The composition according to any one of claims 24 to 31, wherein the solid soluble carrier composition comprises a water-soluble filler.

33. The composition according to claims 24 to 32, wherein the solid soluble carrier composition comprises one or more pH adjusting agents.

34. The composition according to claim 33, wherein the pH adjusting agent increases the pH of the aqueous solution when dissolved in water.

35. The composition according to claim 33 or 34, wherein the pH adjusting agent is selected from the group consisting of ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium bicarbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium bicarbonate (potassium bicarbonate), potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium bicarbonate (sodium bicarbonate), sodium hydroxide, ammonium bicarbonate, zinc hydroxide, and zinc carbonate.

36. The composition according to any one of claims 24 to 35, wherein the ascaloside composition comprises one or more ascalosides and one or more carbonate salts (for example, sodium bicarbonate or potassium bicarbonate).

37. The composition according to claim 36, wherein the ascaloside composition essentially consists of one or more ascalosides and one or more carbonate salts (for example, sodium bicarbonate or potassium bicarbonate).

38. The composition according to any one of claims 24 to 37, characterized in that the composition has a solubility of at least 1, 3, 6, 9, 12, 15, 20, or 25 grams / gallon of water for one or more ascalosides.

39. The composition according to any one of claims 24 to 37, characterized in that the composition has one or more ascalosides that exhibit a solubility in water of at least 0.1, 1, 10, 50, or 100 mM.

40. The composition according to any one of claims 24 to 37, characterized in that the composition has one or more ascalosides that exhibit solubility in water at least 50%, 75%, 100%, 1,000%, 5,000%, or 10,000% higher than the reference.

41. The composition according to claim 40, wherein the reference is a corresponding composition containing only one or more ascalosides.

42. A method of treating a crop or plant with one or more ascalosides, wherein the method is To obtain the ascaloside composition described in any one of claims 24 to 41, The ascaloside composition is mixed with water to form an ascaloside solution, A method comprising applying the ascaloside solution to the crop or plant.

43. The method according to claim 42, wherein the ascaloside composition is mixed with about 2 L to about 10 L of water.

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