Ascaroside particulate compositions and methods for use

Abstract

An ascaroside particulate composition is provided that can be used to form an ascaroside solution. In an embodiment, an ascaroside particulate composition comprises one or more ascarosides and a particulate carrier composition. The ascaroside particulate composition can be dissolved in water and used to treat plants and crops.

Description

ASCAROSIDE PARTICULATE COMPOSITIONSAND METHODS FOR USECROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of priority to U.S. Provisional Appl. No. 63 / 519,978, filed August 16, 2023, the entirety of which is hereby incorporated by reference.FIELD OF THE INVENTION

[0002] The invention is drawn to solid ascaroside compositions and methods relating to use of solid ascaroside compositions.BACKGROUND OF THE INVENTION

[0003] Ascaroside natural products are secondary metabolites produced by nematodes. A large number of structurally diverse ascarosides have been identified in nature and the molecules are believed to function as an evolutionarily conserved chemical language used by nematodes to control many aspects of their development. Ascarosides are also perceived by other organisms and have been demonstrated to have a range of effects on numerous organisms including bacteria, fungi, plants, and mammals including humans. Ascarosides hold potential as human medicines, agrichemicals, and products for other diverse and valuable applications.

[0004] Ascaroside treatments have been demonstrated to show efficacy in increasing plant resistance to certain pathogens and / or in inducing and priming plant defense responses (which can inhibit pathogen growth and / or infestation) when applied to the plant. By activating and / or priming plants’ innate defenses, ascarosides can thereby prevent proliferation of pathogens and / or protect crops from the damaging effects caused by diverse pathogens.

[0005] A unique characteristic of ascarosides is their high potency. Plants respond to extremely low concentrations of ascarosides and as a consequence, the effective application rates needed to prime plant defenses can be very low. This in turn presents challenges with respect to grower convenience and supply chain logistics. The present invention provides solutions to these challenges and related problems.SUMMARY OF THE INVENTION

[0006] The inventors have found that the concentration of ascarosides in a foliar spray needed to prime or induce plant defense responses can be as low as 10 nanomolar. This can correspond to low single digit parts per billion concentrations of ascarosides in an applied foliar spray.Additionally, the inventors have found that foliar application of too high a concentration of ascarosides to crops can lead to a diminution of their beneficial effects. There is therefore a crucial need for practical but accurate methods to apply these products at low concentrations. Use of pure ascarosides to achieve suitably low application rates would require dissolving an extremely small amount of the ascaroside (in some cases only a few milligrams) into tanks holding hundreds of liters of water. This type of measurement and mixing is impractical for growers since they typically lack the equipment required to accurately measure and handle such small quantities. Furthermore, ensuring complete and homogenous dissolution of small quantities of solid ascarosides into large volumes of water can be difficult — ascarosides in their pure form are solids and may be in the form of fine powders. Such powdered ascarosides may not dissolve immediately when added to water and additionally have a tendency to float on the surface of water and / or adhere to the edges of containers. These factors may lead to incomplete dissolution and / or inconsistent application rates.

[0007] One solution to this problem is the use of pre-formulated liquid concentrates of ascaroside which can be conveniently measured and mixed into the agricultural spray tanks. Many agrichemicals are provided as liquid concentrates and are typically formulated so that a grower uses between about ½ a fluid ounce and about 16 fluid ounces of concentrate per acre of crop to be treated (most typically about 1 oz to about 4 oz per acre). Prior to field application, an appropriate volume of concentrate for the acreage to be treated is diluted into a suitable volume of water (typically in a large spray tank) to generate a spray solution that is applied the crop at a rate that ensures good coverage of the foliage (typically about 10-20 gallons per acre for row crops).

[0008] The inventors have determined that certain ascaroside foliar spray treatments are surprisingly efficacious when applied to field crops by foliar spray at extremely low application rates (5 mg to 100 mg / acre) and have created prototype liquid concentrate formulations of ascarosides that growers can conveniently apply using familiar methods to achieve these application rates. Such formulations are convenient to use and work well, but unfortunately are quite inefficient from a logistics standpoint. For example, a prototype ascaroside concentrate was produced to enable convenient application of an ascaroside at rates between around 25- 100 mg / acre. The prototype was designed such that application of 2 fluid ounces per acre will deliver 25 mg of ascaroside per acre. Though this formulation is technically a concentrate, the solution is still very dilute compared to typical agrichemicals and contains less than 0.05 wt%ascaroside. This is inefficient since distribution of such products requires the transport and storage of large amounts of water.

[0009] The present disclosure provides soluble solid ascaroside compositions that are convenient for growers to use but do not suffer from the inefficiencies inherent in the dilute liquid formulations describe above. The provided soluble solid formulations are compatible with ascarosides and have a long shelf life, have good handling characteristics, dissolve in water quickly and completely, are compatible with other agrichemicals and are biocompatible (e.g. nontoxic to plants, humans or the environment).

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

[0011] In another embodiment, a soluble solid ascaroside composition is provided that can be dissolved to conveniently generate a ready-to-spray formulation suitable for application to plants. In an embodiment, the provided composition comprises one or more ascarosides and a soluble solid carrier composition, wherein the ascaroside composition comprises 0.2 wt% or less of the one or more ascarosides. In some embodiments, the ascaroside composition comprises from about 0.005 wt% to about 0.2 wt% of the one or more ascarosides.

[0012] The provided solid ascaroside compositions can be dissolved in water and used to treat plants and crops. In some embodiments, dissolution of the solid ascaroside compositions provides a concentrated solution that is further diluted prior to use. DETAILED DESCRIPTION OF THE INVENTION

[0013] The disclosure provides solid ascaroside compositions that include one or more ascarosides and a solid carrier composition and methods of use. In some embodiments, the solid particulate composition comprises less than 20 wt% of one or more ascarosides. In other embodiments, the composition comprises less than 0.01 wt.% of the one or more ascarosides. As used herein, the term “ascaroside” includes the ascaroside, a derivative or an analog of the ascaroside, or combinations thereof, as will be described in further detail herein.Ascarosides

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

[0015] Ascarosides are derivatives of the sugar ascarylose—a di-deoxy sugar lacking hydroxyl groups at its 3- and 6-positions. Ascarosides have the general structure shown in Formula I:wherein: Z is an optionally substituted C2-40aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group, a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g. -a moiety -C(O)ORc), a C2-20carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

[0016] In certain embodiments, Z is: (i) –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic group(ii) –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (iii) –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is - H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (iv) –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (v) –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (vi) –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (vii) –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, ora linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (viii) –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; or (ix) –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule.

[0017] In certain embodiments, Z is: (x) –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xi) –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xii) –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule;(xiii) –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiv) –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xv) –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvi) –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvii) –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; or (xviii) an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising a nitrogen-, oxygen- or sulfur-containing functional group.

[0018] As defined above and described herein, in some embodiments, Z comprises a nitrogen- , oxygen-, or sulfur-containing functional group. It will be appreciated that “an oxygen-containing functional group” refers to moieties that comprise one or more oxygen atoms (e.g., carbonyl-containing groups such as esters, aldehydes, carboxylic acids, ortho esters, and ketones; ethers, hydroxyls, and heterocyclic rings comprising one or more oxygen atoms and / or one of the foregoing functional groups); “a nitrogen-containing functional group” refers to moieties that comprise one or more nitrogen atoms (e.g., amines, amides, carbamates, imines, ureas, oximes, amidines, guanidines, nitriles, azo groups, azides, and heterocyclic rings comprising one or more nitrogen atoms and / or one of the foregoing functional groups); and “a sulfur-containing functional group” refers to moieties that comprise one or more sulfur atoms (e.g., thioether, sulfone, sulfonic acid, sulfoxide, thiol, thiocyanate, or disulfide).

[0019] In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising an oxygen-containing functional group. In certain embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising a carboxylic acid. In certain embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising an aldehyde. In certain embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising an ester. In some embodiments, Z an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising -CO2R2. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising -CO2H. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising -CO2CH3. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising -CON(R3)2. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising -N(R3)2. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising an ester comprising a linker moiety covalently attached to one or more additional ascaroside molecules.

[0020] As described above, the ascarylose sugar moiety in the provided compounds can be substituted or unsubstituted (i.e., there can be functional groups other than -OH at 2- and 4- positions of the sugar or, stated differently, variables Raand / or Rbcan be other than -H in any of the formulae herein).

[0021] As defined above and described herein, each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl,C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group, a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g., -a moiety -C(O)ORc), a C2-20carbamate (e.g., -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to an ascaroside molecule.

[0022] In certain embodiments, Rais -H. In certain embodiments, Rbis -H. In certain embodiments, Raand Rbare the same. In certain embodiments Raand Rbare both -H. In certain embodiments, Raand Rbare different. In certain embodiments, Rais -H, and Rbis other than - H. In certain embodiments, Rais other than -H and Rbis -H. In certain embodiments, Rais -H and Rbis p-hydroxybenzoate. In certain embodiments, Rais -H and Rbis indole-3-carboxylate. In certain embodiments, Rais -H and Rbis (E)-2-methyl-2-butenoate. In certain embodiments, Rais -H and Rbis picolinate. In certain embodiments, Rais -H and Rbis nicotinate. In certain embodiments, Rais -H and Rbis (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4- oxobutanoate. In certain embodiments, Rais -H and Rbis 4-((4-hydroxyphenethyl)amino)-4- oxobutanoate. In certain embodiments, Racomprises a glycoside, amino acid, a peptide, or nucleotide. In certain embodiments, Rbcomprises a glycoside, amino acid, a peptide, or nucleotide. In certain embodiments, Racomprises a linkage to a second ascaroside molecule. In certain embodiments, Rbcomprises a linkage to an ascaroside molecule. In certain embodiments, Racomprises a sugar. In certain embodiments, Rbcomprises a sugar.

[0023] In some embodiments, Rais an optionally substituted C1-20aliphatic. In some embodiments, Rais an optionally substituted C1-6aliphatic. In some embodiments, Rais C1-20aliphatic. In some embodiments, Rais C1-6aliphatic. In some embodiments, Rais methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, sec-butyl, or t-butyl. In some embodiments, Rais C1-20acyl. In some embodiments, Rais -C(O)Rc. In some embodiments, Rais -C(O)H. In some embodiments, Rais -C(O)CH3. In some embodiments, Rais an optionally substituted C1-20heteroaliphatic. In some embodiments, Rais an optionally substituted C1-6heteroaliphatic. In some embodiments, Rais C1-20heteroaliphatic. In some embodiments, Rais C1-6heteroaliphatic. In some embodiments, Rais an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatomsindependently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais optionally substituted aryl. In some embodiments, Rais optionally substituted phenyl. In some embodiments, Rais phenyl. In some embodiments, Rais an optionally substituted heteroaryl group. In some embodiments, Rais an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais an optionally substituted C2-20carbonate. In some embodiments, Rais -C(O)ORc. In some embodiments, Rais an optionally substituted C2-20carbamate. In some embodiments, Rais -C(O)N(Rc)2. In some embodiments, Rais an optionally substituted C2-20thioester. In some embodiments, Rais -C(S)Rc. In some embodiments, Rais an optionally substituted C2-20thiocarbonate. In some embodiments, Rais -C(S)ORc. In some embodiments, Rais an optionally substituted C2-20dithiocarbonate. In some embodiments, Rais -C(S)SRc. In some embodiments, Rais an optionally substituted C1-20thiocarbamate. In some embodiments, Rais -C(S)N(Rc)2.

[0024] In some embodiments, Rais an optionally substituted hydroxyl protecting group. Suitable hydroxyl protecting groups are well known in the art and include those described in detail in Protecting Groups in Organic Synthesis, T. W. Greene and P. G. M. Wuts, 3rdedition, 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), tri-iso- propylsilyloxymethyl (TOM), and triisopropylsilyl (TIPS) ethers), methyl ethers, and ethoxyethyl ethers. In some embodiments, Rais -ORc.

[0025] In some embodiments, Rais an optionally substituted phosphorous-linked functional group. It will be appreciated that “phosphorous-linked functional group” as used herein refers to moieties that comprise one or more phosphorous atoms (e.g., phosphine, phosphodiester, phosphonic acid, phosphate). In some embodiments, Rais an optionally substituted sulfur- linked functional group. It will be appreciated that “sulfur-linked functional group” as used herein refers to moieties that comprise one or more sulfur atoms (e.g., thioether, sulfone, sulfonic acid, sulfoxide, thiol, thiocyanate, or disulfide). In some embodiments, Rais an optionally substituted silicon-linked functional group. It will be appreciated that “silicon-linked functional group” as used herein refers to moieties that comprise one or more silicon atoms (e.g., silanol, suloxides, siloxanes, silyl ethers, silyl chlorides, silyl hydrides, silenes, or siloles).

[0026] In some embodiments, Rais an optionally substituted sugar moiety. In some embodiments, Rais an optionally substituted peptide. In some embodiments, Rais an optionally substituted polymer chain. In some embodiments, Rais a linkage via a bond or a carbon-containing linker moiety to an ascaroside molecule. In some embodiments, Rais an optionally substituted C1-6aliphatic or heteroaliphatic comprising an ascaroside.

[0027] In some embodiments, Rbis an optionally substituted C1-20aliphatic. In some embodiments, Rbis an optionally substituted C1-6aliphatic. In some embodiments, Rbis C1-20aliphatic. In some embodiments, Rbis C1-6aliphatic. In some embodiments, Rbis methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, sec-butyl, or t-butyl. In some embodiments, Rbis C1-20acyl. In some embodiments, Rbis -C(O)Rc. In some embodiments, Rbis -C(O)H. In some embodiments, Rbis -C(O)CH3. In some embodiments, Rbis an optionally substituted C1-20heteroaliphatic. In some embodiments, Rbis an optionally substituted C1-6heteroaliphatic. In some embodiments, Rbis C1-20heteroaliphatic. In some embodiments, Rbis C1-6heteroaliphatic. In some embodiments, Rbis an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis optionally substituted aryl. In some embodiments, Rbis optionally substituted phenyl. In some embodiments, Rbis phenyl. In some embodiments, Rbis an optionally substituted heteroaryl group. In some embodiments, Rbis an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis an optionally substituted C2-20carbonate. In some embodiments, Rbis -C(O)ORc. In some embodiments, Rbis an optionally substituted C2-20carbamate. In some embodiments, Rbis -C(O)N(Rc)2. In some embodiments, Rbis an optionally substituted C2-20thioester. In some embodiments, Rbis -C(S)Rc. In some embodiments, Rbis an optionally substituted C2-20thiocarbonate. In some embodiments, Rbis -C(S)ORc. In some embodiments, Rbis an optionally substituted C2-20dithiocarbonate. In some embodiments, Rbis -C(S)SRc. In someembodiments, Rais an optionally substituted C1-20thiocarbamate. In some embodiments, Rbis -C(S)N(Rc)2.

[0028] In some embodiments, Rbis an optionally substituted hydroxyl protecting group. In some embodiments, Rbis -ORc.

[0029] In some embodiments, Rbis an optionally substituted phosphorous-linked functional group. In some embodiments, Rbis an optionally substituted sulfur-linked functional group. In some embodiments, Rbis an optionally substituted silicon-linked functional group.

[0030] In some embodiments, Rbis an optionally substituted sugar moiety. In some embodiments, Rais an optionally substituted peptide. In some embodiments, Rbis an optionally substituted polymer chain. In some embodiments, Rbis a linkage via a bond or a carbon-containing linker moiety to an ascaroside molecule. In some embodiments, Rbis an optionally substituted C1-6aliphatic or heteroaliphatic comprising an ascaroside.

[0031] In some embodiments, Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation. In some embodiments, Raand Rbmay be taken together to form an optionally substituted 3- to 12- membered monocyclic or bicyclic saturated or partially unsaturated carbocyclyl or heterocyclyl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Raand Rbmay be taken together to form an optionally substituted 5- to 12-membered monocyclic or bicyclic aryl or heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0032] In certain embodiments, Rais -H and Rbis p-hydroxybenzoate. In certain embodiments, Rais -H and Rbis indole-3-carboxylate. In certain embodiments, Rais -H and Rbis (E)-2- methyl-2-butenoate. In certain embodiments, Rais -H and Rbis picolinate. In certain embodiments, Rais -H and Rbis nicotinate. In certain embodiments, Rais -H and Rbis (R)-2- hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, Rais -H and Rbis 4-((4-hydroxyphenethyl)amino)-4-oxobutanoate.

[0033] In certain embodiments Raand Rbare both -H, and Z is selected from the formulae defined in (i) to (ix) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (i) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (ii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (iii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (iv) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (v) above. In certainembodiments Raand Rbare both -H, and Z conforms to formula (vi) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (vii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (viii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (ix) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (x) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xi) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xiii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xiv) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xv) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xvi) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xvii) above.

[0034] As defined above and described herein, each Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule.

[0035] In some embodiments, Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl.

[0036] In some embodiments, an occurrence of Rcis -H. In some embodiments, Rcis an optionally substituted C1-12aliphatic group. In some embodiments, Rcis an optionally substituted C1-6aliphatic group. In some embodiments, Rcis an optionally substituted C1-12heteroaliphatic group. In some embodiments, Rcis an optionally substituted C1-6heteroaliphatic group. In some embodiments, Rcis an optionally substituted 3- and 8- membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rcis an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rcis an optionally substituted aryl group. In some embodiments, Rcis optionally substituted phenyl. In some embodiments, R2is phenyl. In some embodiments, Rcis an optionally substituted heteroaryl group. In some embodiments, Rcis an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rcis an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0037] As defined above and described herein, R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. In some embodiments, R2is -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, or an optionally substituted aromatic group, an optionally substituted heteroaryl group.

[0038] In some embodiments, R2is -H. In some embodiments, R2is a metal cation. In certain embodiments, R2is an organic cation (e.g. a nitrogen or phosphorous centered cationic group). In some embodiments, R2is an optionally substituted C1-20aliphatic group. In certain embodiments, R2is an optionally substituted C1-12aliphatic group. In certain embodiments, R2is an optionally substituted C1-8aliphatic group. In certain embodiments, R2is an optionally substituted C1-6aliphatic group. In certain embodiments, R2is selected from methyl, ethyl, n- propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In some embodiments, R2is an optionally substituted C1-6aliphatic group. In some embodiments, R2is an optionally substituted C1-20heteroaliphatic group. In some embodiments, R2is an optionally substituted C1-6heteroaliphatic group. In some embodiments, R2is an optionally substituted 3- and 8- membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R2is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R2is an optionally substituted aromatic group. In some embodiments, R2is optionally substituted phenyl. In some embodiments, R2is phenyl. In some embodiments, R2is an optionally substituted heteroaryl group. In some embodiments, R2is an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R2is an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0039] In some embodiments, R2is a glycoside. It will be appreciated that a glycoside refers to a moiety comprising a sugar bound to another functional group via a glycosidic bond.

[0040] In some embodiments, R2is nucleotide. In some embodiments, R2is adenosine monophosphate, cytidine monophosphate, guanosine monophosphate, or uridine monophosphate. In some embodiments, R2is deoxyadenosine monophosphate, deoxycytidine monophosphate, deoxyguanosine monophosphate, or deoxythymidine monophosphate.

[0041] In some embodiments, R2is a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. In some embodiments, R2is an optionally substituted C1-6aliphatic or heteroaliphatic comprising an ascaroside.

[0042] In certain embodiments, R2comprises an amino acid. In certain embodiments, R2comprises a peptide.

[0043] As defined above and described herein, each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. In some embodiments, each R3is independently selected from -H and C1-8aliphatic. In some embodiments, one R3is -H and the other R3is other than -H. In some embodiments, neither R3is -H. In some embodiments, each R3is -H. In some embodiments, an occurrence of R3is an optionally substituted C1-20aliphatic group. In some embodiments, an occurrence of R3is an optionally substituted C1-6aliphatic group. In some embodiments, an occurrence of R3is an optionally substituted C1-20heteroaliphatic group. In some embodiments, an occurrence of R3is an optionally substituted C1-6heteroaliphatic group. In some embodiments, R3is an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R3is an optionally substituted 8- and 12- membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, occurrence of R3is an optionally substituted aryl group. In some embodiments, R3is optionally substituted phenyl. In some embodiments, R3is phenyl. In some embodiments, R3is an optionally substituted heteroaryl group. In some embodiments, R3is an optionally substituted 5- to 6- membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R3is an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0044] In certain embodiments, at least one R3is -H. In certain embodiments, both R3groups are -H. In certain embodiments, at least one R3is an optionally substituted C1-20aliphatic group.In certain embodiments, both R3groups are an optionally substituted C1-20aliphatic group which may be the same or different. In certain embodiments, at least one R3is an optionally substituted C1-12aliphatic group. In certain embodiments, at least one R3is an optionally substituted C1-8aliphatic group. In certain embodiments, at least one R3is an optionally substituted C1-6aliphatic group. In certain embodiments, at least one R3is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In certain embodiments, at least one R3is -CH2CH2OH. In certain embodiments, at least one R3is -CH2CH2OR2. where R2is as defined in the genera and subgenera herein. In certain embodiments, at least one R3is an optionally substituted aromatic group. In certain embodiments, at least one R3comprises a glycoside. In certain embodiments, at least one R3comprises an amino acid. In certain embodiments, at least one R3at least one R3comprises a peptide. In certain embodiments, at least one R3comprises a nucleotide.

[0045] In certain embodiments, an ascaroside is selected from the group consisting of:where x is an integer from 1 to 22, and each of Ra, Rb, and R2is as defined above and in the genera and subgenera herein.

[0046] In certain embodiments, an ascaroside is selected from the group consisting of:where each of x, Ra, and Rb, is as defined above and in the genera and subgenera herein.

[0047] In certain embodiments, an ascaroside is selected from the group consisting of:where y is an integer from 1 to 20, and each of Ra, Rb, and R2is as defined above and in the genera and subgenera herein.

[0048] In certain embodiments, an ascaroside is selected from the group consisting of:where each of y, Ra, and Rb, is as defined above and in the genera and subgenera herein.

[0049] In certain embodiments, an ascaroside is selected from the group consisting of:where each of x and R2is as defined above and in the genera and subgenera herein.

[0050] In certain embodiments, an ascaroside is selected from the group consisting of:where x is as defined above and in the genera and subgenera herein.

[0051] In certain embodiments, an ascaroside is selected from the group consisting of:where each of y and R2is as defined above and in the genera and subgenera herein.

[0052] In certain embodiments, an ascaroside is selected from the group consisting of:where y is as defined above and in the genera and subgenera herein.

[0053] In certain embodiments, an ascaroside is selected from the group consisting of:where each of x, Ra, Rb, and R3is as defined above and in the genera and subgenera herein.

[0054] In certain embodiments, an ascaroside is selected from the group consisting of:where each of x and R3is as defined above and in the genera and subgenera herein.

[0055] In certain embodiments, an ascaroside is selected from the group consisting of:where each of y, Ra, Rb, and R2is as defined above and in the genera and subgenera herein.

[0056] In certain embodiments, an ascaroside is selected from the group consisting of:where each of y and R3is as defined above and in the genera and subgenera herein.

[0057] In an embodiment, ascarosides useful in the context of the present disclosure have the general structure (I), where Z is –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40,and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0058] In an embodiment, ascarosides useful in the context of the present disclosure have the general structure (I) where Z is –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0059] Specific ascarosides that are useful in the context of the present disclosure include, but are not limited to, ascr#7 and ascr#18.

[0060] In certain embodiments, an ascaroside used in the provided methods and compositions 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, an ascaroside used in the provided methods is selected from the group consisting of: ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. In certain embodiments, an ascaroside used in the provided methods is selected from the group consisting of: ascr#9, ascr#14, ascr#10, and ascr#18.

[0061] In certain embodiments, an ascaroside used in the provided methods and compositions 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, an ascaroside used in the provided methods is selected from the group consisting of: oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22. In certain embodiments, an ascaroside used in the provided methods 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, an ascaroside used in the provided methods is selected from the group consisting of: oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

[0062] In certain embodiments, an ascaroside used in the provided methods and compositions is selected from the group consisting of: bhas#9, bhas#10, bhas#16, bhas#18, bhas#22,bhas#24, bhas#26, bhas#28, bhas#30, bhas#32, bhas#34, bhas#36, bhas#38, bhas#40, and bhas#42.

[0063] In certain embodiments, an ascaroside used in the provided methods and compositions is selected from the group consisting of: bhos#10, bhos#16, bhos#18, bhos#22, bhos#24, bhos#26, bhos#28, bhos#30, bhos#32, bhos#34, bhos#36, bhos#38, bhos#40, and bhos#42.

[0064] In certain embodiments, an ascaroside used in the provided methods and compositions 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, an ascaroside used in the provided methods and compositions 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, an ascaroside used in the provided methods and compositions is a blend comprising two or more of: ascr#18, ascr#17, ascr#10, ascr#3, ascr#1, ascr#7, and ascr#9. In certain embodiments, an ascaroside used in the provided methods and compositions is a blend comprising two or more of: ascr#18, ascr#10, ascr#1, and ascr#9.

[0067] In certain embodiments, an ascaroside used in the provided methods and compositions 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, an ascaroside used in the provided methods and compositions 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, an ascaroside used in the provided methods and compositions is ascr#18. In certain embodiments, an ascaroside used in the provided methods and compositions is oscr#16.

[0068] Ascarosides can be obtained from natural sources (e.g., nematodes) or they may be prepared synthetically. Ascarosides can be prepared synthetically, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascarylose. An exemplary method of preparing ascarosides includes: providing as a feedstock a 1-O-substituted rhamnose; forming a mono- sulfonate ester at the 3-OH group of the feedstock; and treating the mono-sulfonate ester with a hydride source to form a 1-O-substituted ascarylose. In certain embodiments, forming the mono-sulfonate ester is conducted on a substrate without hydroxyl protecting groups at the 2- or 4-position of the rhamnose feedstock. In certain embodiments, such methods comprise contacting the feedstock with a sulfonating agent (i.e., a sulfonyl halide, sulfonic anhydride, orsimilar reagent) in the presence of a Lewis acid. Specific details regarding the synthesis of 1- O-substituted ascarylose can be found in international publication No. WO 2022 / 024067, which is incorporated herein by reference. Ascaroside Salts

[0069] In certain embodiments, ascarosides in provided solid compositions comprise ascaroside salts. Ascaroside salts can be formed with appropriate reagents, e.g., at any suitable acidic or basic functional group on the ascaroside molecule.

[0070] In some embodiments, a provided salt is of Formula II’: [A]p- Mp+(Formula II) wherein each of A, M, and p is as defined and described below and herein.

[0071] For example, in some embodiments, carboxylic acid salts (also referred to as carboxylate salts) are provided. Such salts can be depicted according to Formula II, below, where “M” is a metal (or other cation) and “A” is the remainder of the ascaroside molecule to which the carboxylic acid moiety is attached (e.g., the structures according to Formula I, provided herein above): [A-(C(O)O)-]p Mp+(Formula II) where p represents an integer from 1 to 4. In some embodiments, p is 1 and the salt comprises one ascaroside anion and one “M” cation (with +1 charge). In some embodiments, p is 2 and the salt comprises two ascaroside anions and one “M” cation (with +2 charge). In some embodiments, p is 3 and the salt comprises three ascaroside anions and one “M” cation (with +3 charge). In some embodiments, p is 4 and the salt comprises four ascaroside anions and one “M” cation (with +4 charge). In embodiments wherein p is greater than 1, the ascaroside anions present in the salt can be the same or different.

[0072] Referring to the structure of the ascaroside in Formula I, above, it is noted that a carboxylic acid salt can be formed, e.g., at the “ORa” and / or “ORb” substituent of the tetrahydropyranyl ring. In some embodiments, a carboxylic acid can be formed at the ORaand / or ORbsubstituent where Raand / or Rbis –L-C(O)ORc, where L is an optionally-substituted bivalent linker comprising one or more carbon atoms and optionally containing one or more heteroatoms and where Rcis H. In some embodiments, a carboxylic acid can be formed at the ORaand / or ORbsubstituent where Raand / or Rbis a sugar moiety (e.g., a sugar acid) comprisinga carboxylic acid group. In some embodiments, a carboxylic acid can be formed at the ORaand / or ORbsubstituent where Raand / or Rbis a peptide comprising a carboxylic acid group. In some embodiments, a carboxylic acid can be formed at the ORaand / or ORbsubstituent where Raand / or Rbis a polymer comprising a carboxylic acid group. In some embodiments, a carboxylic acid can be formed at the ORaand / or ORbsubstituent where Rcis a polymer chain comprising a carboxylic acid group. In some embodiments, a carboxylic acid can be formed at the ORaand / or ORbsubstituent where Ra and / or Rbis a mono-ester of a diacid. In certain embodiments, such compounds are derived from reaction of a compound where Raand / or Rbis -H with a cyclic acid anhydride such as phthalic, succinic, maleic or glutaric anhydride or any of their substituted analogs. Representative examples of such ascaroside anions are shown below:where each of x and R2is as defined above and in the genera and subgenera herein.

[0073] Again referring to the structure of the ascaroside in Formula I, above, it is noted that a carboxylic acid can be formed, e.g., at the OZ substituent of the tetrahydropyranyl ring. In some embodiments, a carboxylic acid can be formed at the OZ substituent, e.g., when Z is selected from –CH(CH3)–(CH2)n–CO2R2; –CH(CH3)–(CH2)n–CH=CH-CO2R2, –CH(CH3)–(CH2)n– CH(OH)–CH2-CO2R2; –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2; –(CH2)n–CO2R2; –(CH2)n– CH=CH-CO2R2; and –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40 and R2is -H or an optionally substituted C1-20aliphatic group, optionally substituted aromatic group, a glycoside, amino acid, a peptide, or nucleotide that contains a carboxylic acid group.

[0074] In certain embodiments, a linker group -L- comprises an optionally substituted C1-20aliphatic, C1-20heteroaliphatic, aryl, or heteroaryl. Such linkers may be attached to an oxygen atom on the ascaroside molecule via an ether linkage, an ester linkage, a carbonate linkage, acarbamate linkage (e.g., A-OC(O)NR3-), a thioester linkage (e.g., A-OC(S)-), a thiocarbamate linkage (e.g., A-OC(S)NR3-), a thiocarbonate linkage (e.g., A-OC(S)O-), a dithiocarbonate linkage (a thiocarbonate linkage (e.g., A-OC(S)S-), a sulfonate ester linkage (e.g., A-OSO2-), or via a linkage through a phosphorus atom.

[0075] In one embodiment, a salt of ascr#18 is provided, e.g., according to the following formula:where negative charge is shown delocalized over the oxygen atoms of the carboxylic acid.

[0076] The disclosure is not limited to carboxylic acid salts of ascarosides. Salts that can be formed with other functional groups on an ascaroside molecule are also encompassed within the present disclosure. For example, where an ascaroside comprises an amine group (e.g., within the Ra, Rb, or Z substituent), an ammonium salt can be formed with suitable anionic groups. Further, in some embodiments, where an ascaroside comprises a hydroxyl (-OH) group, certain M groups may coordinate thereto to form a salt, e.g., as in a borate or silicate derivative of an ascaroside.

[0077] Shown below are non-limiting, representative metal salts of ascarosides formed through the carboxylic acid group of the sidechain:where x is as defined above and in the genera and subgenera herein.

[0078] Shown below are representative “ate” salts of ascarosides formed through the hydroxy groups of the ascarylose sugar:where x is as defined above and in the genera and subgenera herein.

[0079] The composition of “M” (e.g., as shown in Formula II and IIb above) can vary widely. In some embodiments, M is a metal. Suitable metals are not particularly limited and, in various embodiments, are selected from alkali / Group 1 metals, alkaline earth / Group 2 metals, andtransition metals. In some embodiments, M is a semi-metal or a non-metal, selected from the main group elements. In some embodiments, M is an organic cation such as an ammonium, guanidinium, amidinium, pyridinium, phosphonium, sulfonium, or any similar nitrogen-, phosphorus- or sulfur-centered cation or analog thereof.

[0080] In some embodiments, M comprises a plant micronutrient or a plant macronutrient. 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). One of skill in the art will appreciate that not all such micronutrients and macronutrients can form salts with ascarosides in the same manner.

[0081] For example, salts of plant nutrients such as potassium, calcium, magnesium, zinc, manganese, iron, copper, molybdenum, and nickel can, in some embodiments, be formed with a carboxylic acid on an ascaroside (e.g., according to Formula II or IIb above). Nitrogen may be provided in the form of an ammonium or guanidinium salt of an ascaroside (e.g., wherein M is NH4+or H2N+=C(NH2)2or an ammonium or guanidinium analogue salt of an ascaroside (e.g., wherein one or more of the H atoms of NH4+or H2N+=C(NH2)2is replaced with an alkyl group). Plant nutrients such as boron, silicon and molybdenum may not easily form salts with carboxylic acids but may, for example, coordinate in the form of a borate, a silicate, or a molybdate to a free OH present on the ascaroside molecule to form a suitable salt. As such, in some embodiments, a salt comprising at least one boron atom coordinated to an ascaroside, a salt comprising at least one silicon atom coordinated to an ascaroside, or a salt comprising at least one molybdenum atom coordinated to an ascaroside is provided.

[0082] Further details regarding ascaroside salts can be found in international publication WO 2023 / 220174, filed May 10, 2023, which is incorporated herein by reference. Solid Ascaroside Compositions

[0083] Ascarosides may be applied to plants and crops by various means, and the mode of application is not particularly limited since plants can respond systemically to ascarosides. Non-limiting examples of suitable modes of ascaroside application include seed treatment, foliar spray or dusting, application by root dip or drench, application to soil, application of time-release formulations, injection into stems or trunks, or application of compositions for absorption through bark (e.g. on stems, trunks, branches or vines). Most of these methods of applying ascarosides rely on the use of an aqueous solution of the ascaroside.

[0084] In typical agricultural use, field application rates for ascarosides range from about 5 mg / acre to about 100 mg / acre, with 25 mg / acre to 50 mg / acre being preferred for most crops. At a range of spray rates from 5 gallons per acre to 50 gallons per acre, the concentration of ascaroside needed in the sprayer tank would range from about 5 mg / 50 gallons (0.1 mg / gallon) to about 100 mg / 5 gallons (20 mg / gallon). The accurate measurement of amounts smaller than 1 g is impractical at an agricultural site. Additionally, even if the measurement of sub-gram amounts of ascarosides can be made, or sub-gram quantities of the material can be supplied to the growers (e.g., as a packet of material), ensuring complete and homogenous dissolution of less than 1 g of an ascaroside into many gallons of water is difficult, if not impossible at a typical agricultural site.

[0085] One way to mitigate these problems is to supply a liquid concentrate containing one or more ascarosides that can be easily dispensed into a sprayer tank. In one embodiment, a concentrated solution of one or more ascarosides can be prepared having a volume of 1 quart (1L) to 2.5 gallons (10 L). For example, for an application rate of 25 mg / acre, an aqueous concentrate that includes 422 mg of one or more ascarosides per liter provides a concentrate that would require an application of about 2 oz. (60 mL) of the concentrate per acre. For each acre being treated, 2 oz. of the concentrate would be diluted into water (typically 5 – 20 gallons (19L to 76L) for spraying. This formulation when packaged as a standard 2.5-gallon (10 L) jug provides enough material to treat 160 acres which is in line with the growers’ expectations. Even in concentrate form, the solution contains only 422 parts per million of ascarosides and is 99.96% water. Shipment, storage and distribution of the concentrated form is cost inefficient, with respect to the actual amount of ascaroside being provided.

[0086] In an embodiment, rather than providing a pre-mixed aqueous concentrate to crop farmers / growers, a solid ascaroside composition comprising one or more ascarosides and a solid carrier composition can be distributed. By providing a sufficient amount of a solid carrier composition, the one or more ascarosides are provided in a form that can be easily measured and mixed with water (e.g., at any time prior to use or immediately prior to use). The transportation of such a solid ascaroside composition would substantially reduce the shipping costs of ascaroside to the growers, while providing the growers with a composition that they would be comfortable handling. Such solid ascaroside formulations can be provided as particulates (e.g. as a powder or granular composition), or in other solid forms such as tablets, wafers, or similar regular consolidated forms, each containing a specified amount of ascaroside.

[0087] In one embodiment, a provided solid ascaroside composition is a particulate composition that includes one or more ascarosides and a particulate carrier. The one or more ascarosides include, but are not limited to, any ascarosides or salts of ascarosides as described herein. The one or more ascarosides are blended with a particulate carrier composition. The particulate carrier provides additional bulk to the ascaroside particulate composition, which facilitates the convenient preparation of highly dilute solutions of ascarosides. Additionally, the particulate carrier composition can include one or more compounds that improve the solubility of the one or more ascarosides in water.

[0088] In one embodiment, a provided solid ascaroside composition comprises a tablet composition that includes one or more ascarosides and a solid carrier formed into consolidated shape, preferably, such tablets are of a specific weight and shape to enable simple measurement of a target ascaroside application amount by using an appropriate number of tablets. The one or more ascarosides include, but are not limited to, any ascarosides or salts of ascarosides as described herein. The provided tablets comprise one or more ascarosides blended with a solid carrier composition and optionally binders or coatings necessary to form a cohesive tablet. The carrier provides additional bulk to the ascaroside composition, which facilitates the convenient preparation of highly dilute solutions of ascarosides. Additionally, the tablet composition can include one or more compounds that improve the solubility of the one or more ascarosides in water.

[0089] The concentration of one or more ascarosides in the solid ascaroside compositions can be preselected based on the intended use. In certain embodiments, the solid ascaroside composition comprises 20 wt.% or less of the one or more ascarosides. In additional embodiments, the ascaroside particulate composition comprises 15 wt.% or less of the one or more ascarosides; 10 wt.% or less of the one or more ascarosides; 5 wt.% or less of the one or more ascarosides; 2 wt.% or less of the one or more ascarosides; or 1 wt.% or less of the one or more ascarosides. In certain embodiments, the solid ascaroside composition comprises between about 5 wt.% to about 20 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside composition comprises between about 5 wt.% to about 15 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside composition comprises between about 5 wt.% to about 10 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside composition comprises between about 1 wt.% to about 20 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside composition comprises between about 10 wt.% to about 20 wt.% of the one or more ascarosides. In certainembodiments, the solid ascaroside composition comprises between about 10 wt.% to about 15 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside composition comprises between about 15 wt.% to about 20 wt.% of the one or more ascarosides. Provided solid ascaroside compositions having between about 1 to about 20 wt.% of one or more ascarosides are particularly useful for forming concentrated solutions of ascarosides intended for further dilution prior to use. This can be more convenient for a grower than mixing a solid ascaroside formulation directly into a spray tank since it may be difficult to ensure complete dissolution of a solid in a spray tank where visibility may be poor and / or options for vigorous mixing are limited. Such compositions are especially convenient for preparing compositions for treatment of large areas such as row-crop acreage or large hydroponic systems in commercial settings. In certain embodiments, such solid ascaroside compositions may be provided in a container that is suitable for forming such a concentrate: for example a pre- measured amount of the solid can be provided in a mostly-empty 2.5 gallon jug that can filled with water on site and prior to use to provide 2.5 gallons of a liquid ascaroside concentrate for application at a rate of 1-4 fluid oz per acre.

[0090] For making solutions of ascarosides suitable for direct use without further dilution, a solid ascaroside composition is provided that contains less than about 0.5 wt.% of the one or more ascarosides. In certain embodiments, such compositions contain less than about 0.4 wt.%, less than about 0.3 wt.%, less than about 0.25 wt.%, less than about 0.2 wt.%, less than about 0.15 wt.%, less than about 0.1 wt.%, less than about 0.05 wt.%, less than about 0.01 wt.% or less than about 0.005 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside compositions comprises between about 0.005 wt.% and about 1 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside compositions comprises between about 0.005 wt.% and about 0.05 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside compositions comprises between about 0.005 wt.% and about 0.5 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside compositions comprises between about 0.005 wt.% and about 0.1 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside compositions comprises between about 0.1 wt.% and about 1 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside compositions comprises between about 0.05 wt.% and about 1 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside compositions comprises between about 0.5 wt.% and about 1 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside compositions comprises between about 0.05 wt.% and about0.5 wt.% of the one or more ascarosides. In certain embodiments, the solid ascaroside compositions comprises between about 0.01 wt.% and about 0.1 wt.% of the one or more ascarosides. Ascaroside particulate compositions having between about 0.01 wt.% and about 0.1 wt.% of one or more ascarosides are particularly useful for forming compositions of ascarosides that do not require further dilution prior to use. Such compositions are especially convenient for preparing compositions for treatment of relatively small areas such as home gardens, houseplants, lawns, or individual trees and shrubs. In certain embodiments, such solid ascaroside compositions may be provided in a container that is suitable for forming a liquid formulation on site: for example a pre-measured amount of the solid can be provided in a 1 quart or 1 gallon spray bottle that can filled with water on site and sprayed directly on plants to provide an effective application rate of ascarosides.

[0091] To avoid any doubt, will be understood that, within the present disclosure, when solid ascaroside compositions reference “wt.%,” the “wt.%” refers to the weight of the individual component relative to the total weight of the composition.

[0092] In some embodiments, ascarosides in the provided solid ascaroside compositions are present in a salt form. The counter ion for the salt form of the ascaroside can include an element that is also useful as a plant nutrient. Plant nutrient elements 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). Plant nutrient elements can exist in cationic form or anionic form. These elements can be oxidized to form ionic forms.

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

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

[0095] Exemplary 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] When used in ascaroside particulate compositions, as described herein, a polyethylene glycol or polypropylene glycol should be a solid at temperatures up to about 40 ºC. For example, polyethylene glycols having an average molecular weight between about 3000 to about 8000 are generally suitable as water-soluble fillers. Polyethylene glycol and polypropylene glycol can have the added benefit of improving the solubility of the ascarosides 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 the one or more ascarosides in water.

[0097] In one embodiment, the solid carrier composition in a provided solid ascaroside composition comprises one or more pH adjusting agents. One or more pH adjusting agents that can be included in the carrier composition include pH decreasing agents and pH increasing agents. A pH decreasing agent decreases the pH of water when dissolved in pure water. A pH increasing agent increases the pH of water when dissolved in pure water.

[0098] Exemplary pH decreasing 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 hydrogen sulfite, sodium hydrogen sulfate, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium hydrogen sulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide.

[0099] Exemplary pH increasing agents include, but are not limited to, ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium hydrogen carbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium hydrogen carbonate (potassium hydrogen bicarbonate), potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium hydrogen carbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium hydrogen carbonate (sodium bicarbonate), sodium hydroxide, ammonium hydrogen carbonate, 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 someembodiments, 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 comprises 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. Carbonate, bicarbonate, and phosphate salts, in addition to acting as a pH increasing agent, are also useful for buffering soil pH against acidification. Additionally, carbonates can sequester heavy metals in the soil surrounding the plants. Phosphates are used as fertilizers to promote plant grown and development.

[0101] In some embodiments, the solid ascaroside composition comprises between about 80 wt.% and about 99 wt.% of the pH increasing agent. In some embodiments, the solid ascaroside composition comprises between about 80 wt.% and about 95 wt.% of the pH increasing agent. In some embodiments, the solid ascaroside composition comprises between about 80 wt.% and about 90 wt.% of the pH increasing agent. In some embodiments, the solid ascaroside composition comprises between about 99 wt.% and about 99.995 wt.% of the pH increasing agent. In some embodiments, the solid ascaroside composition comprises between about 99 wt.% and about 99.95 wt.% of the pH increasing agent. In some embodiments, the solid ascaroside composition comprises between about 99 wt.% and about 99.9 wt.% of the pH increasing agent.

[0102] In some embodiments, an advantage of pH increasing agents is that increasing the pH of the solution can increase the solubility of the ascarosides having a carboxylic acid moiety. Additionally or alternatively, if the ascaroside is in a salt form, the use of pH increasing agents can help maintain the salt form of the ascasroside if the water used to prepare the composition is acidic.

[0103] In some embodiments, provided solid ascaroside compositions comprise one or more ascarosides, wherein the solid ascaroside compositions are characterized in that the one or more ascarosides display solubilities in water of at least 1, 3, 6, 9, 12, 15, 20, or 25 grams / gallon. In some embodiments, provided solid ascaroside compositions comprise one or more ascarosides, wherein the solid ascaroside compositions are characterized in that the one or more ascarosides display solubilities in water of at least 0.1, 1, 10, 50, or 100 mM. In some embodiments, provided solid ascaroside compositions comprise one or more ascarosides, wherein the solidascaroside compositions are characterized in that the one or more ascarosides display solubilities in water of at least 0.2, 0.3, 0.4, 0.5, 0.75, or 1 M. In some embodiments, solubility is measured at room temperature (e.g., 25 °C).

[0104] In some embodiments, provided solid ascaroside compositions comprise one or more ascarosides, wherein the solid ascaroside compositions are characterized in that the one or more ascarosides display solubilities in water of at least 50%, 75%, 100%, 1,000%, 5,000%, or 10,000% higher than a reference. In some embodiments, the reference is a corresponding composition containing solely the one or more ascarosides.

[0105] Ascarosides that include a carboxylic acid can react with a pH increasing agent (e.g., a carbonate) to form a carboxylate salt. The carboxylate salt of an ascaroside has an increased water solubility. The use of pH increasing agents has the advantage of promoting in situ salt formation in ascarosides having a carboxylic acid. In some embodiments, the solid ascaroside composition consists essentially of, or consists of, one or more ascarosides and a carbonate salt. In some embodiments, the solid ascaroside composition consists essentially of, or consists of, one or more ascarosides and a bicarbonate salt. In some embodiments, the solid ascaroside composition consists essentially of, or consists of, one or more ascarosides and a phosphate salt. In some embodiments, such carbonate- bicarbonate- or phosphate-salts comprise a potassium, sodium, or quaternary ammonium cation. Solid ascaroside compositions can include one or more ascarosides, one or more water-soluble fillers and one or more pH adjusting agents.

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

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

[0108] In some embodiments, the present disclosure provides a solid ascaroside composition, comprising: one or more ascarosides, and means for dissolving the one or more ascarosides in water at a concentration of at least about 0.1, 1, 10, 50, or 100 mM.

[0109] In some embodiments, the present disclosure provides a solid ascaroside composition, comprising: one or more ascarosides, and means for dissolving the one or more ascarosides 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 a solid ascaroside composition, comprising: one or more ascarosides, and means for dissolving the one or more ascarosides 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 the one or more ascarosides comprises a pH adjusting agent. In some embodiments, the means for dissolving the one or more ascarosides comprises a pH increasing agent. In some embodiments, solubility is measured at room temperature (e.g., 25 °C).

[0112] In some embodiments, the present disclosure provides a solid ascaroside composition, comprising: one or more ascarosides, and means for enhancing the solubility (e.g., in water) of the one or more ascarosides.

[0113] In some embodiments, the means for enhancing the solubility of the one or more ascarosides comprises a pH adjusting agent. In some embodiments, the means for enhancing the solubility of the one or more ascarosides comprises a pH increasing agent. In some embodiments, the solubility of the one or more ascarosides is increased by at least 50%, 75%, 100%, 1,000%, 5,000%, or 10,000% higher than a reference. In some embodiments, solubility is measured at room temperature (e.g., 25 °C).

[0114] In some embodiments, the present disclosure provides a solid ascaroside composition, comprising: one or more ascarosides, and means for providing an aqueous ascaroside composition, wherein the concentration of the one or more ascarosides is at least about 0.1, 1, 10, 50, or 100 mM.

[0115] In some embodiments, the present disclosure provides a solid ascaroside composition, comprising: one or more ascarosides, and means for providing an aqueous ascaroside composition, wherein the concentration of the one or more ascarosides 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 a solid ascaroside composition, comprising: one or more ascarosides, and means for providing an aqueous ascaroside composition, wherein the concentration of the one or more ascarosides is at least about 1, 3, 6, 9, 12, 15, 20, or 25 grams / gallon.

[0117] In some embodiments, the means for providing the aqueous ascaroside composition comprises a pH adjusting agent. In some embodiments, the means for providing the aqueous ascaroside composition comprises a pH increasing agent. In some embodiments, solubility is measured at room temperature (e.g., 25 °C).

[0118] It has been found that microbes including fungi and molds can grow in aqueous ascaroside solutions including the aqueous ascaroside concentrates described above, this can be addressed by packaging such solutions under sterile conditions. But problems still arise in situations where packages of such solutions are opened and then stored in non-sterile environments (e.g. on farms) since the product shelf life after opening may be compromised. This is an additional drawback of providing commercial ascaroside formulations as dilute aqueous solutions. It has been found that solutions generated from the solid ascaroside formulations provided herein have greater stability against microbial contamination than pure ascaroside solutions. Fungal growth may be reduced or inhibited in such solution, particularly when a pH adjusting agent that raises the pH of the ascaroside solution is used. In certain embodiments, solid ascaroside compositions are provided that, when dissolved in water provide ascaroside solutions with enhanced stability against microbial contamination or growth(e.g. mold or fungal growth). In certain embodiments, such compositions comprise one or more ascarosides and one or more pH adjusting agents that raise the pH of the resulting solution. In certain embodiments, such pH increasing agents are provided in a molar excess relative to any acid functionalities of the ascaroside(s) so that when the composition is dissolved in water, the ascaroside solution has a pH above 7 (e.g., above 7.5, above 8, above 8.5, above 9, or above 9.5).

[0119] Solid ascaroside compositions can be made from any technique used for 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 ascaroside particulate compositions can be formed into a granular material by known means including use of binders, prilling, etc. Powder formulations may benefit from inclusion of anti-caking agents or moisture controlling additives to keep the material in a free-flowing form. Solid ascaroside compositions comprising tablets, pellets, wafers, spheres, or similar regular solid forms can be made by known means including pressing, molding, extruding, and the like. Such compositions may benefit from incorporation of binders to aid in adhesion of the material in the solid and / or coatings to improve the appearance, handling characteristics or stability of such solid forms.

[0120] Granulation generally is the process wherein particles of powder are made to adhere to one another to form granules. Granulation is useful because it produces relatively homogeneous mixing of different sized particles. A dry granulation process can be used to form an ascaroside particulate composition without using a liquid solution. Dry granulation may be conducted on a press using slugging tooling or on a roller compactor commonly referred to as a chilsonator.

[0121] Wet granulation involves forming granules using a granulating fluid or wetting agent that is subsequently removed by drying. Examples of 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 of the granulator. A low-shear granulator uses very little mechanical force to combine powders. The fluid-bed granulator uses a high volume of air flow to elevate powders in a chamber for mixing. A fluid-bed granulator does not impart mechanical energy but instead relies on the powder characteristics and the binding solution to form the lightly held powders into granules. After the granulation process is completed, the resulting mixture may be dried to remove at least a portion of the solvent.

[0122] Melt granulation is a process in which powders are transformed into solid aggregates or agglomerates while being heated. It is similar to wet granulation except that a binder acts as a wetting agent only after it has melted. Use of Solid Ascaroside Compositions

[0123] Solid ascaroside compositions, as disclosed herein, are generally dissolved in water to form a solution that includes one or more ascarosides. In one embodiment, the solid ascaroside composition is provided to a user in a container. Examples of containers include, but are not limited to a canister, a can, a drum, a bottle, a bag, or a pouch. The container can be made from a polymer, glass, or metal. The ascaroside particulate composition is generally provided with instructions on how to prepare a solution from the solid ascaroside composition. Such instructions may include an amount of the ascaroside particulate composition (e.g., by weight or by volume) and the amount of water to which the solid ascaroside composition is added. For example, instructions can include a weight of the ascaroside particulate composition per gallon of water. In another example, the instructions can include the volume of ascaroside particulate composition per gallon of water. To aid in the mixing, a scoop designed to contain the proper amount of the ascaroside particulate composition for a predetermined volume of water can be provided.

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

[0125] The single use container can be designed for forming an ascaroside concentrated solution. As used herein a “concentrated solution” refers to a solution of one or more ascarosides in water, wherein the concentration of the ascarosides is greater than the concentration of ascarosides in water needed for application. Prior to use a concentrated solution requires dilution. In certain embodiments, the ascaroside in the single use container is intended to be added to between about 1 quart (e.g. a 1-quart bottle) to about 300 gallons (e.g. an IBC tote). In certain embodiments, provided solid ascaroside compositions are packaged in a single use package sufficient to generate a concentrated ascaroside solution when dissolved in a bottle or pail (for example, having a volume of about 0.5 Gal. (1.9 L), about 1.0Gal. (3.8 L), about 1.5 Gal. (5.7 L), about 2.0 Gal. (7.6 L), about 2.5 Gal. (9.5 L), about 3 Gal. (11.4 L), 4 Gal. (15.1 L), or 5 Gal. (18.9 L)). In certain embodiments, provided solid ascaroside compositions are packaged in a single use package sufficient to generate a concentrated ascaroside solution when dissolved in a drum or tank (for example, a plastic or metal drum having a volume of about 10 Gal, about 20 Gal. about 30 Gallons, or about 55 Gal., or an IBC tote having a volume of about 110 Gal., about 120 Gal., about 140 Gal., about 180 Gal., about 220 Gal., about 250 Gal., about 275 Gal., about 300 Gal., about 330 Gal., about 350 Gal., about 450 Gal., or about 550 Gal.. Concentrated solutions resulting from dissolution of the solid ascaroside composition according to the provided instructions typically have a concentration of ascarosides of about 0.05 mM to 10 mM.

[0126] In general, the amount of solid ascaroside composition added to the concentrate should not exceed the solubility of the components of the solid ascaroside composition. In certain embodiments, a provided solid ascaroside composition has an ascaroside content and associated instructions for use, such that the concentrated ascaroside solution resulting from dissolution of the provided ascaroside solid composition according to the instructions has a concentration such that application of from about 0.5 fluid ounces (15 mL) to about 8 ounces (240 mL) of the concentrate per acre of crop to be treated (e.g. after further dilution into an appropriate spray volume) provides an effective application of ascaroside to the crop (e.g. to reduce damage of the crop by pathogens). In certain embodiments, a provided solid ascaroside composition is formulated such that dissolution of the solid within a range from about 1 tablespoon (15 mL) per 5 gallons to about 1 / 2 cup (120 mL) per gallon (high concentration). This provides a good balance of convenience for the grower (amounts that are easily measured and dissolve quickly) and logistical efficiency (minimizing storage and transport of inert ingredients). In certain embodiments, a provided solid ascaroside composition is formulated such that dissolution of the about 1 tablespoon (15 mL) of solid per 1 gallon provides a concentrated solution.

[0127] The single use container can also be designed to contain an amount of ascaroside such that dissolution of the entire contents provide an ascaroside solution at approximately the concentration needed to apply to plants without further dilution. For example, a single use product targeting row crop growers can be provided in a quantity such that the entire contents of the single use package when added directly to a spray tank treats a number of acres (e.g.1- 100 acres). Such a single use package can also be targeted to smaller growers or home gardeners by providing a package which, when its entire contents are dissolved in a smallervolume of water (e.g. 0.5 to 5 gallons) provides volume of ready-to-spray solution which sill conveniently deliver an efficacious amount of ascarosides when applied to smaller areas such as a garden or an individual plant. Ready-to-use solutions resulting from dissolution of the solid ascaroside composition according to the provided instructions typically have a concentration of ascarosides of about 25 nM to about 10 uM. In certain embodiments, a provided solid ascaroside composition is formulated such that dissolution of the about 1 tablespoon (15 mL) of solid per 1 gallon provides a solution with a concentration of ascarosides of about 1 micromolar. In certain embodiments, a provided solid ascaroside composition is formulated such that dissolution of the about 1 tablespoon (15 mL) of solid per 1 gallon provides a solution with a concentration of ascarosides of about 5 micromolar. In certain embodiments, a provided solid ascaroside composition is formulated such that dissolution of the about 1 tablespoon (15 mL) of solid per 1 gallon provides a solution with a concentration of ascarosides of about 100 nanomolar.

[0128] In an alternate embodiment, the solid ascaroside composition can be distributed to end-users in a mostly-empty container configured such that it can hold a predetermined volume of water. The instructions would then only include directions for adding the appropriate amount of water to the container. The container can be designed for formation of a concentrated solution of the ascaroside particulate composition. Alternatively, the container can be designed for formation of a solution of the ascaroside that is ready-to use, having the appropriate concentration of ascarosides after water is added to the container.

[0129] The formulations may additionally contain “adjuvant surfactants” to enhance deposition, wetting, and penetration of the compounds onto the target crop and organism. These “adjuvant surfactants” may be employed as a component of the compositions. The amount of adjuvant surfactant will typically vary from 0.01 to 1.0 percent by weight preferably 0.05 to 0.5 percent by weight. Suitable adjuvant surfactants include, but are not limited to ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts of the esters or sulfosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines, blends of surfactants with mineral or vegetable oils, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-Cu alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C12-C16) ethoxylate; di-sec- butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate(8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99. The formulations may also include oil-in-water emulsions.

[0130] In the case of wettable formulations, “Surfactants” may comprise about 0.5% to about 10% of the composition. Suitable “Surfactants” for wettable powders include sulfonated lignins, condensed naphthalene-sulfonates, the naphthalene-sulfonates, alkyl- benzenesulfonates, alkylsulfonates or nonionic surfactants such as ethylene oxide adducts of alkylphenols or mixtures thereof.

[0131] Representative organic solvents which may be employed in preparing solutions from the solid ascaroside compositions are aromatic liquids such as xylene, propyl benzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, particularly the dimethyl amides of fatty glycols and glycol derivatives such as the n-butyl ether, ethyl ether or methyl ether of diethylene glycol, the methyl ether of triethylene glycol, amides of simple carboxylic acids, such as dimethyl formamide and dimethyl acetamide, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; terpenic solvents, rosin derivatives, aliphatic ketones such as cyclohexanone, complex aliphatic and aromatic alcohols such as 2-ethoxyethanol, vegetable oils such as soy bean oil, rape seed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cotton seed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; and the like. Mixtures of two or more organic liquids may also be employed in the preparation of the emulsifiable concentrate. Organic liquids include xylene, and propyl benzene fractions, with xylene being most preferred in some cases.

[0132] “Emulsifiers” for emulsifiable concentrates are typically mixed ionic and / or nonionic surfactants such as those mentioned herein or their equivalents. Examples of nonionic emulsifiers useful in preparing the emulsifiable concentrates include the polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with the polyol or polyoxyalkylene. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include the oil soluble salts (e.g., calcium) of alkylaryl sulphonic acids, oil-soluble salts or sulfated polyglycol ethers and appropriate salts of phosphated- polyglycol ether.

[0133] Compositions described herein may include 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 clays, diatomaceous earths, purified silicates, or the like.

[0134] “Aqueous suspensions” may be prepared of the solid ascaroside compositions where the composition is dispersed in an aqueous vehicle at a concentration typically in the range of between about 5% to about 50% by weight. The suspensions are prepared by finely grinding the solid ascaroside composition and vigorously mixing it into a vehicle of water, surfactants, and dispersants. Inert ingredients such as inorganic salts and synthetic or natural gums may also be employed to increase the density and / or viscosity of the aqueous vehicle as is desired.

[0135] In some aspects, the present disclosure provides methods of preparing ready-to-use ascaroside compositions, comprising: providing a solid ascaroside composition as defined and described above and herein; combining the solid ascaroside composition with a liquid solvent (e.g., water) at a first concentration; and further adding the liquid solvent (e.g., water); wherein the solid ascaroside composition comprises 20% or less by weight of the one or more ascarosides.

[0136] In some aspects, the present disclosure provides methods of preparing ready-to-use ascaroside compositions, comprising: providing a solid ascaroside composition as defined and described above and herein; and combining the solid ascaroside composition with a liquid solvent (e.g., water) at a first concentration; wherein the solid ascaroside composition comprises 0.2 wt.% or less by weight of the one or more ascarosides. EXAMPLES

[0137] Example 1. Formation and Use of a Solid Particulate Ascaroside Composition for Agricultural Application: A solid ascaroside composition composed of ascr#18 sodium bicarbonate was formulated by combining 10 grams of the ascaroside as a fine powder and 70grams of the 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 jar including a measuring cup (e.g., a scoop) having a volume of 1 tablespoon (15 mL). For field use, the measuring cup is used to measure one level scoop of the solid ascaroside composition and dissolved in 1 gallon (3.8 L) of water to form a concentrate solution. This concentrate solution is added to a spray tank at a rate of two fluid ounces per acre of crop to be treated. The one gallon of solution treats 64 acres of crop and delivers an effective application rate of ascr#18 of about 25 mg per acre.

[0138] Example 2. Formulation and Use of an Alternate Solid Particulate Ascaroside Composition for Agriculture: A solid ascaroside composition composed of ascr#18 and potassium bicarbonate was formulated by combining 100 grams of the ascaroside as a fine powder and 700 grams of the 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 jar including a measuring cup (e.g., a scoop) having a volume of 1 tablespoon (15 mL). For field use, the measuring cup is used to measure one level scoop of the solid ascaroside composition and dissolved in 1 gallon (3.8 L) of water to form a concentrate solution. This concentrate solution is added to a spray tank at a rate of two fluid ounces per acre of crop to be treated. The one gallon of solution treats 64 acres of crop and delivers an effective application rate of ascr#18 of about 25 mg per acre. This formulation also delivers a small amount of potassium nutrient to the treated crop.

[0139] Example 2b. Formulation and Use of an Alternate Solid Particulate Ascaroside Composition for Agriculture: A mixture was formed as described in Example 2, except the potassium bicarbonate was substituted with a commercial formulation of potassium bicarbonate (MilStop™ SP) which contains additional components such as anticaking agents and surfactants. The product of Example 2 had a tendency to clump into a solid mass which was difficult to remove from the packaging and hard to accurately measure. In contrast, the product of Example 2b remained a free flowing powder that was convenient to measure and dissolve.

[0140] Example 3. Comparative solubility of pure ascarosides and a provided solid ascaroside composition: Two one-gallon plastic containers were filled 1 / 3 full of clean tap water. To the first container 1 scoop of the composition described in Example 1 was added. The solid sank to the bottom of the container and dissolved within 30 seconds of gentle mixing with a polyethylene paddle. To the second container was added 1.5g of pure ascr#18 powder, someof the ascaroside floated on the surface of the water as fine particulates and some formed clumps. Mixing resulted in slow dissolution after several minutes of vigorous mixing, solid was still visible, and some of the ascaroside had adhered to the side of container at the water line and to the polyethylene paddle. Each container was then filled with additional clean water to reach 1 gallon. The solution from the provided solid formulation remained clear and colorless with no visible solid present. The solution from direct addition of ascaroside still contained solids visible at the bottom of the container and adhered to the sides.

[0141] Example 4. Comparative stability of solutions derived from pure ascarosides or a provided solid ascaroside composition: A 100 mL portion of the 1 gallon of concentrate produced in Example 1, and 100 mL of a comparative concentrate produced by dissolving 1.5g of pure ascaroside 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 derived from the solid ascaroside composition showed no change in appearance or evidence of fungal growth, while the solution derived directly from ascaroside became cloudy and had visible fungal growth suspended within it.

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

[0143] Example 6. In another example, an application rate of 25 mg ascarosides per acre is desired. To treat 160 acres at this application rate, 4000 mg (4 g) of ascaroside is needed. An ascaroside particulate composition that includes 20% of ascaroside / 80% particulate carrier composition is prepared by mixing 4 g of ascr#18 and 50 g of sodium bicarbonate (NaHCO3). The added bulk of the particulate carrier makes measurement of the composition easier for theuser to measure, while reducing transportation costs associated with shipment of quantities or water. The use of sodium bicarbonate in the particulate carrier composition aids dissolution of the ascr#18 since this ascaroside has higher solubility in alkaline solutions.

[0144] Example 7. Formulation and Use of a Solid Ascaroside Particulate Composition for Residential Application: A solid ascaroside composition composed of ascr#18 and potassium bicarbonate was formulated by combining 32 milligrams of the ascaroside as a fine powder and 500 grams of the potassium bicarbonate as a fine powder. The mixture was placed in an industrial blender and homogenized for 5 minutes. Ten 0.10g samples were removed from the mixture which was agitated between the removal of each sample to ensure samples represent the bulk composition. The samples were dissolved in water and analyzed by HPLC-MS and found to contain a consistent amount of ascaroside indicating the solid mixture is homogenous. The resulting powder was then packaged in a polyethylene jar including a measuring cup (e.g., a scoop) having a volume of 1 tablespoon (15 mL). For use, the measuring cup is used to measure one level scoop of the solid ascaroside composition and dissolved in 1 gallon (3.8 L) of water to form a ready to spray solution. This solution has an ascaroside concentration of approximately 1 micromolar, a concentration that is effective for pathogen control in most plants tested. DEFINITIONS

[0145] In order for the present disclosure to be more readily understood, certain terms are defined below. Additional definitions for the following terms and other terms are set forth throughout the specification. In this application, unless otherwise clear from context, the term “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.” In this application, the terms “comprising” and “including” may be understood to encompass itemized components or steps whether presented by themselves or together with one or more additional components or steps. As used in this application, the term “comprise” and variations of the term, such as “comprising” and “comprises,” are not intended to exclude other additives, components, integers, or steps.

[0147] About, Approximately: As used herein, the terms “about” and “approximately” are used as equivalents. Unless otherwise stated, the terms “about” and “approximately” may be understood to permit standard variation as would be understood by those of ordinary skill in the art. Where ranges are provided herein, the endpoints are included. Any numerals used inthis application with or without about / approximately are meant to cover any normal fluctuations appreciated by one of ordinary skill in the relevant art. Unless otherwise stated, the term above refers to within 25% of a given value. In some embodiments, the term “approximately” or “about” refers 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 the stated reference value unless otherwise stated or otherwise evident from the context (except where such number would exceed 100 % of a possible value).

[0148] Definitions of specific functional groups and chemical terms are described in more detail below. For purposes of this invention, the chemical elements are identified in accordance with 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. Additionally, general principles of organic chemistry, as well as specific functional moieties 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; 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 can comprise one or more asymmetric centers, and thus can exist in various stereoisomeric forms, e.g., enantiomers and / or diastereomers. Thus, inventive compounds and compositions thereof may be in the form of an individual enantiomer, diastereomer or geometric isomer, or may be in the form of a mixture of stereoisomers. In certain embodiments, compounds described herein are enantiopure compounds. In certain other embodiments, mixtures of enantiomers or diastereomers are provided.

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

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

[0152] Where a particular enantiomer is preferred, it may, in some embodiments be provided substantially free of the opposite enantiomer and may also be referred to as “optically enriched.” “Optically enriched,” as used herein, means that the compound is made up of a significantly greater proportion of one enantiomer. In certain embodiments the compound is made up of at least about 90% by weight of an enantiomer. In some embodiments the compound is made up of at least about 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9% by weight of an enantiomer. In some embodiments the enantiomeric excess of provided compounds is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9%. In some embodiments, enantiomers may be isolated from racemic mixtures by any method known to those skilled in the art, including chiral high pressure liquid chromatography (HPLC) and the formation and crystallization of chiral salts or prepared by asymmetric syntheses. See, for example, Jacques, et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981); Wilen, S.H., et al., Tetrahedron 33:2725 (1977); Eliel, E.L. Stereochemistry of Carbon Compounds (McGraw–Hill, NY, 1962); Wilen, S.H. Tables of Resolving Agents and Optical Resolutions p.268 (E.L. Eliel, Ed., Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0153] The terms “halo” and “halogen” as used herein refer to an atom selected from fluorine (fluoro, –F), chlorine (chloro, –Cl), bromine (bromo, –Br), and iodine (iodo, –I).

[0154] The term “aliphatic” or “aliphatic group”, as used herein, denotes a hydrocarbon moiety that may be straight–chain (i.e., unbranched), branched, or cyclic (including fused, bridging, and spiro–fused polycyclic) and may be completely saturated or may contain one or more units of unsaturation, but which is not aromatic. Unless otherwise specified, aliphatic groups contain 1–30 carbon atoms. In certain embodiments, aliphatic groups contain 1–12 carbon atoms. In certain embodiments, aliphatic groups contain 1–8 carbon atoms. In certain embodiments, aliphatic groups contain 1–6 carbon atoms. In some embodiments, aliphatic groups contain 1– 5 carbon atoms, in some embodiments, aliphatic groups contain 1–4 carbon atoms, in yet other embodiments aliphatic groups contain 1–3 carbon atoms, and in yet other embodiments aliphatic groups contain 1–2 carbon atoms. Suitable aliphatic groups include, but are not limited to, linear or branched, alkyl, alkenyl, and alkynyl groups, and hybrids thereof such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl or (cycloalkyl)alkenyl.

[0155] The term “heteroaliphatic” or “heteroaliphatic group”, as used herein, denotes an aliphatic group where one or more carbon or hydrogen atoms are replaced by a heteroatom (e.g. oxygen, nitrogen, sulfur, phosphorous, boron, etc.). In some embodiments, a heteroaliphatic group is a heterocyclyl group.

[0156] The term "unsaturated", as used herein, means that a moiety has one or more double or triple bonds.

[0157] The term “alkyl,” as used herein, refers to saturated, straight– or branched–chain hydrocarbon radicals derived from an aliphatic moiety containing between one and six carbon atoms by removal of a single hydrogen atom. Unless otherwise specified, alkyl groups contain 1–12 carbon atoms. In certain embodiments, alkyl groups contain 1–8 carbon atoms. In certain embodiments, alkyl groups contain 1–6 carbon atoms. In some embodiments, alkyl groups contain 1–5 carbon atoms, in some embodiments, alkyl groups contain 1–4 carbon atoms, in yet other embodiments alkyl groups contain 1–3 carbon atoms, and in yet other embodiments alkyl groups contain 1–2 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, dodecyl, and the like.

[0158] The term “alkenyl,” as used herein, denotes a monovalent group derived from a straight– or branched–chain aliphatic moiety having at least one carbon–carbon double bond by the removal of a single hydrogen atom. Unless otherwise specified, alkenyl groups contain 2–12 carbon atoms. In certain embodiments, alkenyl groups contain 2–8 carbon atoms. In certain embodiments, alkenyl groups contain 2–6 carbon atoms. In some embodiments, alkenyl groups contain 2–5 carbon atoms, in some embodiments, alkenyl groups contain 2–4 carbon atoms, in yet other embodiments alkenyl groups contain 2–3 carbon atoms, and in yet other embodiments alkenyl groups contain 2 carbon atoms. Alkenyl groups include, for example, ethenyl, propenyl, butenyl, 1–methyl–2–buten–1–yl, and the like.

[0159] The term “aryl” used alone or as part of a larger moiety as in “aralkyl”, “aralkoxy”, or “aryloxyalkyl”, refers to monocyclic and polycyclic ring systems having a total of five to 20 ring members, wherein at least one ring in the system is aromatic and wherein each ring in the system contains three to twelve ring members. The term “aryl” may be used interchangeably with the term “aryl ring”. In certain embodiments, “aryl” refers to an aromatic ring system which includes, but is not limited to, phenyl, biphenyl, naphthyl, anthracyl and the like, whichmay bear one or more substituents. Also included within the scope of the term “aryl”, as it is used herein, is a group in which an aromatic ring is fused to one or more additional rings, such as benzofuranyl, indanyl, phthalimidyl, naphthimidyl, phenantriidinyl, or tetrahydronaphthyl, and the like.

[0160] The terms “heteroaryl” and “heteroar–,” used alone or as part of a larger moiety, e.g., “heteroaralkyl,” or “heteroaralkoxy,” refer to groups having 5 to 10 ring atoms, preferably 5, 6, or 9 ring atoms; having 6, 10, or 14 ^electrons shared in a cyclic array; and having, in addition to carbon atoms, from one to five heteroatoms. The term “heteroatom” refers to nitrogen, oxygen, or sulfur, and includes any oxidized form of nitrogen or sulfur, and any quaternized form of a basic nitrogen. Heteroaryl groups include, without limitation, thienyl, furanyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolizinyl, purinyl, naphthyridinyl, and pteridinyl. The terms “heteroaryl” and “heteroar–”, as used herein, also include groups in which a heteroaromatic ring is fused to one or more aryl, cycloaliphatic, or heterocyclyl rings, where the radical or point of attachment is on the heteroaromatic ring. Nonlimiting examples include indolyl, isoindolyl, benzothienyl, benzofuranyl, dibenzofuranyl, indazolyl, benzimidazolyl, benzthiazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 4H–quinolizinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, and pyrido[2,3–b]–1,4–oxazin– 3(4H)–one. A heteroaryl group may be monocyclic, bicyclic, bridged bicyclic, or spirocyclic. The term “heteroaryl” may be used interchangeably with the terms “heteroaryl ring,” “heteroaryl group,” or “heteroaromatic,” any of which terms include rings that are optionally substituted. The term “heteroaralkyl” refers to an alkyl group substituted by a heteroaryl, wherein the alkyl and heteroaryl portions independently are optionally substituted. The term “heteroarylenyl” refers to bivalent heteroaryl groups (e.g., pyridylenyl).

[0161] As used herein, the terms “heterocycle,” “heterocyclyl,” “heterocyclic radical,” and “heterocyclic ring” are used interchangeably and refer to a stable 5– to 7–membered monocyclic or 7–10–membered bicyclic heterocyclic moiety that is either saturated or partially unsaturated, and having, in addition to carbon atoms, one or more, preferably one to four, heteroatoms, as defined above. When used in reference to a ring atom of a heterocycle, the term "nitrogen" includes a substituted nitrogen. As an example, in a saturated or partially unsaturated ring having 0–3 heteroatoms selected from oxygen, sulfur or nitrogen, the nitrogenmay 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 attached to its pendant group at 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, without limitation, tetrahydrofuranyl, tetrahydrothiophenyl pyrrolidinyl, piperidinyl, pyrrolinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl, oxazolidinyl, piperazinyl, dioxanyl, dioxolanyl, diazepinyl, oxazepinyl, thiazepinyl, morpholinyl, and quinuclidinyl. The terms “heterocycle,” “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 cycloaliphatic rings, such as indolinyl, 3H–indolyl, chromanyl, phenanthridinyl, or tetrahydroquinolinyl. In some embodiments, a heterocyclic ring may be a 5-12 membered bicyclic, bridged bicyclic, or spirocyclic ring. A heterocyclic ring may include one or more oxo (=O) or thioxo (=S) substituent. The term “heterocyclylalkyl” refers to an alkyl group substituted by a heterocyclyl, wherein the alkyl and heterocyclyl portions independently are optionally substituted.

[0163] As used herein, the term “partially unsaturated” refers to a ring moiety that includes at least one double or triple bond. The term “partially unsaturated” is intended to encompass rings having multiple sites of unsaturation, but is not intended to include aryl or heteroaryl moieties, as herein defined.

[0164] As described herein, compounds as provided herein may contain “optionally substituted” moieties. In general, the term “substituted”, whether preceded by the term “optionally” or not, means that one or more hydrogens of the designated moiety are replaced with a suitable substituent. Unless otherwise indicated, an “optionally substituted” group may have a suitable substituent at each substitutable position of the group, and when more than one position in any given structure may be substituted with more than one substituent selected from a specified group, the substituent may be either the same or different at every position. Combinations of substituents envisioned are preferably those that result in the formation of stable or chemically feasible compounds. The term “stable,” as used herein, refers to compounds that are not substantially altered when subjected to conditions to allow for their production, detection, and, in certain embodiments, their recovery, purification, and use for one or more of the purposes disclosed herein.

[0165] Suitable monovalent substituents on a substitutable carbon atom of an “optionally substituted” group are independently halogen; –(CH2)0–4Rº; –(CH2)0–4ORº; -O-(CH2)0-4C(O)OR°; –(CH2)0–4CH(ORº)2; –(CH2)0–4SRº; –(CH2)0–4Ph, which may be substituted with R°; –(CH2)0–4O(CH2)0–1Ph which may be substituted with R°; –CH=CHPh, which may be substituted with R°; –NO2; –CN; –N3; –(CH2)0–4N(Rº)2; –(CH2)0–4N(Rº)C(O)Rº; –N(Rº)C(S)Rº; –(CH2)0-4N(Rº)C(O)NRº2; –N(Rº)C(S)NRº2; –(CH2)0–4N(Rº)C(O)ORº; -N(Rº)N(Rº)C(O)Rº; –N(Rº)N(Rº)C(O)NRº2; –N(Rº)N(Rº)C(O)ORº; – (CH2)0–4C(O)Rº; -C(S)Rº; –(CH2)0–4C(O)ORº; –(CH2)0–4C(O)N(Rº)2; –(CH2)0–4C(O)SRº; – (CH2)0–4C(O)OSiRº3; –(CH2)0–4OC(O)Rº; –OC(O)(CH2)0–4SR–, SC(S)SR°; –(CH2)0–4SC(O)Rº; –(CH2)0–4C(O)NRº2; -C(S)NRº2; –C(S)SR°; –SC(S)SR°, –(CH2)0–4OC(O)NRº2; – C(O)N(ORº)Rº; –C(O)C(O)Rº; -C(O)CH2C(O)Rº; –C(NORº)Rº; –(CH2)0–4SSRº; –(CH2)0–4S(O)2Rº; –(CH2)0–4S(O)2ORº; -(CH2)0–4OS(O)2Rº; –S(O)2NRº2; –(CH2)0–4S(O)Rº; – N(Rº)S(O)2NRº2; –N(Rº)S(O)2Rº; -N(ORº)Rº; –C(NH)NRº2; –P(O)2Rº; –P(O)Rº2; – OP(O)Rº2; –OP(O)(ORº)2; SiRº3; –(C1–4straight or branched alkylene)O–N(Rº)2; or –(C1–4straight or branched alkylene)C(O)O–N(Rº)2, wherein each Rº may be substituted as defined below and is independently hydrogen, C1-8aliphatic, –CH2Ph, –O(CH2)0–1Ph, or a 5–6– membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or, notwithstanding the definition above, two independent occurrences of Rº, taken together with their intervening atom(s), form a 3–12– membered saturated, partially unsaturated, or aryl mono– or polycyclic ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, which may be substituted as defined below.

[0166] Suitable monovalent substituents of Rº together with their intervening atoms), are independently halogen, –(CH2)0–2R●, –(haloR●), –(CH2)0–2OH, –(CH2)0–2OR●, –(CH2)0–2CH(OR●)2; -O(haloR●), –CN, –N3, –(CH2)0–2C(O)R●, –(CH2)0–2C(O)OH, –(CH2)0–2C(O)OR●, -(CH2)0-4C(O)N(Rº)2; –(CH2)0–2SR●, –(CH2)0–2SH, –(CH2)0–2NH2, –(CH2)0–2NHR●, -(CH2)0–2NR●2, –NO2, –SiR●3, –OSiR●3, –C(O)SR●, –(C1–4straight or branched alkylene)C(O)OR●, or –SSR●wherein each R●is unsubstituted or where preceded by “halo” is substituted only with one or more halogens, and is independently selected from C1–4aliphatic, -CH2Ph, –O(CH2)0–1Ph, or a 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents on a saturated carbon atom of Rº include =O and =S.

[0167] Suitable divalent substituents on a saturated carbon atom of an “optionally substituted” group include the following: =O, =S, =NNR*2, =NNHC(O)R*, =NNHC(O)OR*, =NNHS(O)2R*, =NR*, =NOR*, –O(C(R*2))2–3O–, or –S(C(R*2))2–3S–, wherein each independent occurrence of R*is selected from hydrogen, C1–6aliphatic which may be substituted as defined below, or an unsubstituted 5–6–membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents that are bound to vicinal substitutable carbons of an “optionally substituted” group include: –O(CR*2)2–3O–, wherein each independent occurrence of R*is selected from hydrogen, C1–6aliphatic which may be substituted as defined below, or an unsubstituted 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0168] Suitable substituents on the aliphatic group of R*include halogen, –R●, -(haloR●), – OH, –OR●, –O(haloR●), –CN, –C(O)OH, –C(O)OR●, –NH2, –NHR●, –NR●2, or –NO2, wherein each R●is unsubstituted or where preceded by “halo” is substituted only with one or more halogens, and is independently C1–4aliphatic, –CH2Ph, –O(CH2)0–1Ph, or a 5–6– membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0169] Suitable substituents on a substitutable nitrogen of an “optionally substituted” group include –R†, –NR†2, –C(O)R†, –C(O)OR†, –C(O)C(O)R†, –C(O)CH2C(O)R†, – S(O)2R†, -S(O)2NR†2, –C(S)NR†2, –C(NH)NR†2, or –N(R†)S(O)2R†; wherein each R†is independently hydrogen, C1–6aliphatic which may be substituted as defined below, unsubstituted –OPh, or an unsubstituted 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or, notwithstanding the definition above, two independent occurrences of R†, taken together with their intervening atom(s) form an unsubstituted 3–12–membered saturated, partially unsaturated, or aryl mono– or bicyclic ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0170] Suitable substituents on the aliphatic group of R†are independently halogen, –R●, – (haloR●), –OH, –OR●, –O(haloR●), –CN, –C(O)OH, –C(O)OR●, –NH2, –NHR●, –NR●2, or -NO2, wherein each R●is unsubstituted or where preceded by “halo” is substituted only with one or more halogens, and is independently C1–4aliphatic, –CH2Ph, –O(CH2)0–1Ph, or a 5-6-membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0171] As used herein, the term “substantially” refers to the qualitative condition of exhibiting total or near-total extent or degree of a characteristic or property of interest.

[0172] The convention of naming ascarosides by a several-letter prefix followed by a pound sign (#) and a number is sometimes used (for example ascr#18). This convention is used in the scientific literature and the skilled artisan will understand that each such name is associated with a specific chemical structure of known composition and will readily apprehend the structure of the molecule referred to using this naming convention. Unless otherwise indicated, all compound identifiers of this format used herein conform to the definitions described in the C. elegans Small Molecule Identifier Database (SMID-DB) maintained on the World Wide Web at smid-db.org.

[0173] Embodiments of the invention include: 1. An ascaroside composition comprising one or more ascarosides and a soluble solid carrier composition, wherein the ascaroside composition comprises 20% or less by weight of the one or more ascarosides. 2. The composition of embodiment 1, wherein the ascaroside composition comprises 1% by weight to 20% by weight of the one or more ascarosides. 3. The composition of embodiment 1 or 2, wherein said one or more one ascarosides comprises an ascaroside having the structure (I):where: Z is an optionally substituted C3-40aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g. -a moiety -C(O)ORc), a C2-20carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugarmoiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation. 4. The composition of embodiment 3, wherein Z is selected from the group consisting of: i. –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic group ii. –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iii. –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iv. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; v. –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; vi. –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; vii. –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide;viii. –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is - H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and ix. –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 5. The composition of embodiment 3, wherein Z is selected from the group consisting of: (x) –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xi) –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xii) –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiii) –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule;(xiv) –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xv) –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvi) –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; or (xvii) –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule. 6. The composition of any one of embodiments 3-5, wherein Raand Rbare each -H. 7. The composition of any one of embodiments 3-6, wherein Z is –CH(CH3)–(CH2)n– CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 8. The composition of any one of embodiments 1-7, wherein said at least one ascaroside comprises an ascaroside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24.9. The composition of any one of embodiments 1-8, wherein said at least one ascaroside comprises ascr#18.10. The composition of any one of embodiments 1-9, wherein at least one ascaroside is an ascaroside salt.11. The composition of any one of embodiments 1-10, wherein the carrier composition comprises a water-soluble filler.12. The composition of embodiment 11, wherein the water-soluble filler is a carbohydrate.13. The composition of embodiment 12, wherein the carbohydrate water-soluble filler is selected from the group consisting of lactose, glucose, fructose, mannose, mannitol, sucrose, confectioner's sugar, black sugar, brown sugar, soft brown sugar, microcrystalline cellulose, starch, and powdered cellulose.14. The composition of embodiment 11, wherein the water-soluble filler is a neutral inorganic salt.15. The composition of embodiment 14, wherein the inorganic salt is calcium nitrate, calcium chloride, copper(II) phosphate, copper(l) chloride, copper(II) carbonate, copper(l) 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 of embodiment 11, wherein the water-soluble filler is a polyethylene glycol.17. The composition of embodiment 16, wherein the polyethylene glycol has an average molecular weight between 3000 and 8000.18. The composition of embodiment 1-17, wherein the particulate carrier composition comprises one or more pH adjusting agents.19. The composition of embodiment 18, wherein the pH adjusting agent decreases the pH of an aqueous solution when dissolved in water.20. The composition of 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 hydrogen sulfite, sodium hydrogen sulfate, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium hydrogen sulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide. 21. The composition of embodiment 18, wherein the pH adjusting agent increases the pH of an aqueous solution when dissolved in water. 22. The composition of 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 hydrogen carbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium hydrogen carbonate, potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium hydrogen carbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium hydrogen carbonate, sodium hydroxide, ammonium hydrogen carbonate, zinc hydroxide, and zinc carbonate. 23. The composition of any one of embodiments 1-22, wherein the ascaroside particulate composition comprises one or more ascarosides and one or more carbonate salts. 24. The composition of any one of embodiments 1-22, wherein the particulate carrier composition comprises one or more water-soluble fillers and one or more pH adjusting agents. 25. The composition of embodiment 1, wherein the particulate composition consists essentially of one or more ascarosides and one or more carbonate salts. 26. A method of treating crops or plants with one or more ascarosides, the method comprising: obtaining a soluble solid ascaroside composition comprising one or more ascarosides and a soluble solid carrier composition, wherein the ascaroside composition comprises 20% or less by weight of the one or more ascarosides,mixing the ascaroside composition with water to form an ascaroside solution; and applying the ascaroside solution to the crops or plants. 27. The method of embodiment 26, wherein the particulate composition is mixed with about 2L to about 10L of water. 28. The method of embodiment 26 or 27, wherein the particulate composition is placed in a container prior to mixing with the water. 29. The method of any one of embodiments 26-28, wherein the concentration of the one or more ascarosides in the water, after mixing, is about 0.5 mM to about 2 mM. 30. The method of any one of embodiments 26-29, wherein the ascaroside particulate composition is mixed with water forming a concentrated solution and wherein the method further comprises diluting the concentrated solution with water to form a diluted solution. 31. The method of embodiment 30, wherein the diluted solution is applied to the crops or plants. 32. The method of any one of embodiments 26-31, wherein the ascaroside composition comprises 1% by weight to 20% by weight of the one or more ascarosides. 33. The method of any one of embodiments 26-32, wherein said one or more one ascarosides comprises an ascaroside having the structure (I):where: Z is an optionally substituted C3-40aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g. -a moiety -C(O)ORc), a C2-20carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20dithiocarbonate(e.g. a moiety -C(S)SRc), a C1-20thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation. 34. The method of embodiment 33, wherein Z is selected from the group consisting of: x. –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic group xi. –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xii. –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xiii. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xiv. –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xv. –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xvi. –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionallysubstituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xvii. –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is - H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and xviii. –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 35. The composition of embodiment 32, wherein Z is selected from the group consisting of: (x) –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xi) –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xii) –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiii) –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substitutedaromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xiv) –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xv) –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvi) –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; or (xvii) –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule. 36. The method of any one of embodiments 33-35, wherein Raand Rbare each -H. 37. The method of any one of embodiments 33-36, wherein Z is –CH(CH3)–(CH2)n– CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.38. The method of any one of embodiments 26-37, wherein said at least one ascaroside comprises an ascaroside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. 39. The method of any one of embodiments 26-38, wherein said at least one ascaroside comprises ascr#18. 40. The method of any one of embodiments 26-39, wherein at least one ascaroside is an ascaroside salt. 41. The method of any one of embodiments 26-40, wherein the particulate carrier composition comprises a water-soluble filler. 42. The method of embodiment 41, wherein the water-soluble filler is a carbohydrate. 43. The method of embodiment 42, wherein the carbohydrate water-soluble filler is selected from the group consisting of lactose, glucose, fructose, mannose, mannitol, sucrose, confectioner's sugar, black sugar, brown sugar, soft brown sugar, microcrystalline cellulose, starch, and powdered cellulose. 44. The method of embodiment 41, wherein the water-soluble filler is a neutral inorganic salt. 45. The method of 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 of embodiment 41, wherein the water-soluble filler is a polyethylene glycol. 47. The method of embodiment 46, wherein the polyethylene glycol has an average molecular weight between 3000 and 8000. 48. The method of embodiment 26-47, wherein the particulate carrier composition comprises one or more pH adjusting agents.49. The method of embodiment 48, wherein the pH adjusting agent decreases the pH of an aqueous solution when dissolved in water. 50. The method of 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 hydrogen sulfite, sodium hydrogen sulfate, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium hydrogen sulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide. 51. The method of embodiment 48, wherein the pH adjusting agent increases the pH of an aqueous solution when dissolved in water. 52. The method of 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 hydrogen carbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium hydrogen carbonate, potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium hydrogen carbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), trisodium phosphate, sodium hydrogen carbonate, sodium hydroxide, ammonium hydrogen carbonate, zinc hydroxide, and zinc carbonate. 53. The method of any one of embodiments 26-52, wherein the ascaroside particulate composition comprises one or more ascarosides and one or more carbonate salts. 54. The method of any one of embodiments 26-53, wherein the particulate carrier composition comprises one or more water-soluble fillers and one or more pH adjusting agents. 55. The method of embodiment 26, wherein the particulate composition consists essentially of one or more ascarosides and one or more carbonate salts.56. An ascaroside composition comprising one or more ascarosides and a solid soluble carrier composition, wherein the ascaroside composition comprises 0.2% or less by weight of the one or more ascarosides. 57. The composition of embodiment 56, wherein the ascaroside composition comprises 0.005% by weight to 0.2% by weight of the one or more ascarosides. 58. The composition of embodiment 56 or 57, wherein said one or more one ascarosides comprises an ascaroside having the structure (I):where: Z is an optionally substituted C3-40aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g. -a moiety -C(O)ORc), a C2-20carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation. 59. The composition of embodiment 58, wherein Z is selected from the group consisting of: xix. –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic groupxx. –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxi. –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxii. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxiii. –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxiv. –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxv. –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxvi. –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is - H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and xxvii. –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 60. The composition of embodiment 58, wherein Z is selected from the group consisting of:(x) –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xi) –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xii) –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiii) –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xiv) –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xv) –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an aminoacid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvi) –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; or (xvii) –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule. 61. The composition of any one of embodiments 58-60, wherein Raand Rbare each -H. 62. The composition of any one of embodiments 58-61, wherein Z is –CH(CH3)–(CH2)n– CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 63. The composition of any one of embodiments 56-62, wherein said at least one ascaroside comprises an ascaroside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. 64. The composition of any one of embodiments 56-63, wherein said at least one ascaroside comprises ascr#18. 65. The composition of any one of embodiments 56-64, wherein at least one ascaroside is an ascaroside salt. 66. The composition of any one of embodiments 56-65, wherein the particulate carrier composition comprises a water-soluble filler. 67. The composition of embodiment 66, wherein the water-soluble filler is a carbohydrate.68. The composition of embodiment 67, wherein the carbohydrate water-soluble filler is selected from the group consisting of lactose, glucose, fructose, mannose, mannitol, sucrose, confectioner's sugar, black sugar, brown sugar, soft brown sugar, microcrystalline cellulose, starch, and powdered cellulose.69. The composition of embodiment 66, wherein the water-soluble filler is a neutral inorganic salt.70. The composition of embodiment 69, wherein the inorganic salt is calcium nitrate, calcium chloride, copper(II) phosphate, copper(I) chloride, copper(II) carbonate, copper(I) iodide, iron(Il) molybdate, potassium sulfate, potassium bromide, potassium chloride, potassium nitrate, magnesium nitrate, magnesium chloride, magnesium sulfate, sodium sulfate, sodium chloride, sodium nitrite, and sodium nitrate.71. The composition of embodiment 66, wherein the water-soluble filler is a polyethylene glycol.72. The composition of embodiment 71, wherein the polyethylene glycol has an average molecular weight between 3000 and 8000.73. The composition of embodiment 56-72, wherein the particulate carrier composition comprises one or more pH adjusting agents.74. The composition of embodiment 73, wherein the pH adjusting agent decreases the pH of an aqueous solution when dissolved in water.75. The composition of embodiment 74, 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 hydrogen sulfite, sodium hydrogen sulfate, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium hydrogen sulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide.76. The composition of embodiment 73, wherein the pH adjusting agent increases the pH of an aqueous solution when dissolved in water.77. The composition of embodiment 76, 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 hydrogen carbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium hydrogen carbonate, potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium hydrogen carbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium hydrogen carbonate, sodium hydroxide, ammonium hydrogen carbonate, zinc hydroxide, and zinc carbonate.78. The composition of any one of embodiments 56-77, wherein the ascaroside particulate composition comprises one or more ascarosides and one or more carbonate salts.79. The composition of any one of embodiments 56-78, wherein the particulate carrier composition comprises one or more water-soluble fillers and one or more pH adjusting agents.80. The composition of embodiment 56, wherein the particulate composition consists essentially of one or more ascarosides and one or more carbonate salts.81. A method of treating crops or plants with one or more ascarosides, the method comprising: obtaining a soluble solid ascaroside composition comprising one or more ascarosides and a soluble solid carrier composition, wherein the ascaroside composition comprises 0.2% or less by weight of the one or more ascarosides, mixing the ascaroside particulate composition with water to form an ascaroside solution; and applying the ascaroside solution to the crops or plants.82. The method of embodiment 81, wherein the particulate composition is mixed with about 2L to about 10L of water.83. The method of embodiment 81 or 82, wherein the particulate composition is placed in a container prior to mixing with the water.84. The method of any one of embodiments 81-83, wherein the ascaroside composition comprises 0.005% by weight to 0.2% by weight of the one or more ascarosides. 85. The method of any one of embodiments 81-84, wherein said one or more one ascarosides comprises an ascaroside having the structure (I):where: Z is an optionally substituted C3-40aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g. -a moiety -C(O)ORc), a C2-20carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation. 86. The method of embodiment 85, wherein Z is selected from the group consisting of: xxviii. –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic group xxix. –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide;xxx. –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxxi. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxxii. –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxxiii. –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxxiv. –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; xxxv. –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is - H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and xxxvi. –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 87. The method of embodiment 85, wherein Z is selected from the group consisting of: (x) –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, anamino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xi) –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xii) –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiii) –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (xiv) –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xv) –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvi) –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, anoptionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; or (xvii) –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule. 88. The method of any one of embodiments 85-87, wherein Raand Rbare each -H. 89. The method of any one of embodiments 85-88, wherein Z is –CH(CH3)–(CH2)n– CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 90. The method of any one of embodiments 81-89, wherein said at least one ascaroside comprises an ascaroside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. 91. The method of any one of embodiments 81-90, wherein said at least one ascaroside comprises ascr#18. 92. The method of any one of embodiments 81-91, wherein at least one ascaroside is an ascaroside salt. 93. The method of any one of embodiments 81-92, wherein the particulate carrier composition comprises a water-soluble filler. 94. The method of embodiment 93, wherein the water-soluble filler is a carbohydrate. 95. The method of embodiment 94, wherein the carbohydrate water-soluble filler is selected from the group consisting of lactose, glucose, fructose, mannose, mannitol, sucrose, confectioner's sugar, black sugar, brown sugar, soft brown sugar, microcrystalline cellulose, starch, and powdered cellulose.96. The method of embodiment 93, wherein the water-soluble filler is a neutral inorganic salt. 97. The method of embodiment 96, 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. 98. The method of embodiment 93, wherein the water-soluble filler is a polyethylene glycol. 99. The method of embodiment 98, wherein the polyethylene glycol has an average molecular weight between 3000 and 8000. 100. The method of embodiment 81-99, wherein the particulate carrier composition comprises one or more pH adjusting agents. 101. The method of embodiment 100, wherein the pH adjusting agent decreases the pH of an aqueous solution when dissolved in water. 102. The method of embodiment 101, 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 hydrogen sulfite, sodium hydrogen sulfate, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium hydrogen sulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide. 103. The method of embodiment 100, wherein the pH adjusting agent increases the pH of an aqueous solution when dissolved in water. 104. The method of embodiment 103, 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 hydrogen carbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium hydrogencarbonate, potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium hydrogen carbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium hydrogen carbonate, sodium hydroxide, ammonium hydrogen carbonate, zinc hydroxide, and zinc carbonate.105. The method of any one of embodiments 81-104, wherein the ascaroside particulate composition comprises one or more ascarosides and one or more carbonate salts.106. The method of any one of embodiments 81-105, wherein the particulate carrier composition comprises one or more water-soluble fillers and one or more pH adjusting agents.107. The method of embodiment 81, wherein the particulate composition consists essentially of one or more ascarosides and one or more carbonate salts.

[0174] It is contemplated that compounds, compositions, and methods of the present application encompass variations and adaptations developed using information from the embodiments described in the present disclosure. Adaptation or modification of the methods and processes described in this specification may be performed by those of ordinary skill in the relevant art.

[0175] It will be appreciated that use of headers in the present disclosure are provided for the convenience of the reader. The presence and / or placement of a header is not intended to limit the scope of the subject matter described herein. Unless otherwise specified, embodiments located in one section of the application apply throughout the application to other embodiments, both singly and in combination.

[0176] Throughout the description, where compositions, compounds, or products are described as having, including, or comprising specific components, or where processes and methods are described as having, including, or comprising specific steps, it is contemplated that, additionally, there are articles, devices, and systems of the present application that consist essentially of, or consist of, the recited components, and that there are processes and methods according to the present application that consist essentially of, or consist of, the recited processing steps.

[0177] It should be understood that the order of steps or order for performing certain action is immaterial so long as the described method remains operable. Moreover, two or more steps or actions may be conducted simultaneously.

[0178] All publications and patent applications mentioned in the specification are indicative of the level of those skilled in the art to which this invention pertains. All publications and patent applications are herein incorporated by reference to the same extent as if each individual publication or patent application was specifically and individually indicated to be incorporated by reference.

[0179] Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, it will be obvious that certain changes and modifications may be practiced within the scope of the appended claims.

Claims

CLAIMS What is claimed is:

1. An ascaroside composition comprising one or more ascarosides and a soluble solid carrier composition, wherein the ascaroside composition comprises about 20 wt.% or less of the one or more ascarosides.

2. The composition of claim 1, wherein the ascaroside composition comprises about 1 wt.% to about 20 wt.% of the one or more ascarosides.

3. The composition of claim 1 or 2, wherein said one or more one ascarosides comprises an ascaroside having the structure (I):where: Z is an optionally substituted C3-40aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g. -a moiety -C(O)ORc), a C2-20carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

4. The composition of claim 3, wherein Z is selected from the group consisting of: i. –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic group ii. –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iii. –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iv. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; v. –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; vi. –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; vii. –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; viii. –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is - H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and ix. –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

5. The composition of claim 3, wherein Z is selected from the group consisting of: x. –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; xi. –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; xii. –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xiii. –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; xiv. –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xv. –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromaticgroup, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xvi. –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; xvii. –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; or xviii. an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising a nitrogen-, oxygen- or sulfur-containing functional group.

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

7. The composition of any one of claims 1-6, wherein one or more ascarosides comprises ascr#18.

8. The composition of any one of claims 1-7, wherein at least one ascaroside is an ascaroside salt.

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

10. The composition of claim 1-9, wherein the soluble solid carrier composition comprises one or more pH adjusting agents.

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

12. The composition of 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 hydrogen carbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium hydrogen carbonate (potassium bicarbonate), potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium hydrogen carbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium hydrogen carbonate (sodium bicarbonate), sodium hydroxide, ammonium hydrogen carbonate, zinc hydroxide, and zinc carbonate.

13. The composition of any one of claims 1-11, wherein the ascaroside composition comprises one or more ascarosides and one or more carbonate salts (e.g., sodium bicarbonate or potassium bicarbonate).

14. The composition of any one of claims 1-13, wherein the ascaroside composition consists essentially of one or more ascarosides and one or more carbonate salts (e.g., sodium bicarbonate or potassium bicarbonate).

15. The composition of any one of claims 1-14, wherein the composition is characterized in that the one or more ascarosides display solubilities in water of at least 1, 3, 6, 9, 12, 15, 20, or 25 grams / gallon.

16. The composition of any one of claims 1-14, wherein the composition is characterized in that the one or more ascarosides display solubilities in water of at least 0.1, 1, 10, 50, or 100 mM.

17. The composition of any one of claims 1-14, wherein the composition is characterized in that the one or more ascarosides display solubilities in water of at least 50%, 75%, 100%, 1,000%, 5,000%, or 10,000% higher than a reference.

18. The composition of claim 17, wherein the reference is a corresponding composition containing solely the one or more ascarosides.

19. A method of treating crops or plants with one or more ascarosides, the method comprising: obtaining the ascaroside composition of any one of claims 1-18, mixing the ascaroside composition with water to form an ascaroside solution; and applying the ascaroside solution to the crops or plants.

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

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

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

23. The method of claim 22, wherein the diluted solution is applied to the crops or plants.

24. An ascaroside composition comprising one or more ascarosides and a solid soluble carrier composition, wherein the ascaroside composition comprises 0.2 wt.% or less of the one or more ascarosides.

25. The composition of claim 24, wherein the ascaroside composition comprises about 0.005 wt.% to about 0.05 wt.% of the one or more ascarosides.

26. The composition of claim 24 or 25, wherein said one or more one ascarosides comprises an ascaroside having the structure (I):where: Z is an optionally substituted C3-40aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, ahydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g. -a moiety -C(O)ORc), a C2-20carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

27. The composition of claim 26, wherein Z is selected from the group consisting of: i. –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic group ii. –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iii. –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iv. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; v. –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide;vi. –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; vii. –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; viii. –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is - H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and ix. –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

28. The composition of claim 26, wherein Z is selected from the group consisting of: x. –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; xi. –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; xii. –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, apolymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xiii. –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; xiv. –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xv. –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xvi. –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; xvii. –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; orxviii. an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising a nitrogen-, oxygen- or sulfur-containing functional group.

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

30. The composition of any one of claims 24-29, wherein said at least one ascaroside comprises ascr#18.

31. The composition of any one of claims 24-30, wherein at least one ascaroside is an ascaroside salt.

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

33. The composition of claim 24-32, wherein the solid soluble carrier composition comprises one or more pH adjusting agents.

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

35. The composition of 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 hydrogen carbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium hydrogen carbonate (potassium bicarbonate), potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium hydrogen carbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium hydrogen carbonate (sodium bicarbonate), sodium hydroxide, ammonium hydrogen carbonate, zinc hydroxide, and zinc carbonate.

36. The composition of any one of claims 24-35, wherein the ascaroside composition comprises one or more ascarosides and one or more carbonate salts (e.g., sodium bicarbonate or potassium bicarbonate).

37. The composition of claim 36, wherein the ascaroside composition consists essentially of one or more ascarosides and one or more carbonate salts (e.g., sodium bicarbonate or potassium bicarbonate).

38. The composition of any one of claims 24-37, wherein the composition is characterized in that the one or more ascarosides display solubilities in water of at least 1, 3, 6, 9, 12, 15, 20, or 25 grams / gallon.

39. The composition of any one of claims 24-37, wherein the composition is characterized in that the one or more ascarosides display solubilities in water of at least 0.1, 1, 10, 50, or 100 mM.

40. The composition of any one of claims 24-37, wherein the composition is characterized in that the one or more ascarosides display solubilities in water of at least 50%, 75%, 100%, 1,000%, 5,000%, or 10,000% higher than a reference.

41. The composition of claim 40, wherein the reference is a corresponding composition containing solely the one or more ascarosides.

42. A method of treating crops or plants with one or more ascarosides, the method comprising: obtaining the ascaroside composition of any one of claims 24-41, mixing the ascaroside composition with water to form an ascaroside solution; and applying the ascaroside solution to the crops or plants.

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

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