Aascaroside particle compositions and methods of use

Abstract

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

Description

[0001] Cross-reference to related applications

[0002] This application claims priority to U.S. Provisional Application No. 63 / 519,978, filed August 16, 2023, the entire contents of which are hereby incorporated by reference. Technical Field

[0003] This invention relates to solid ascaroside compositions and methods related to the use of solid ascaroside compositions. Background Technology

[0004] Ascaroside is a natural product of nematodes, a secondary metabolite produced by them. A large number of structurally diverse ascarosides have been identified in nature, and these molecules are believed to function as an evolutionarily conserved chemical language used by nematodes to control many aspects of their development. Ascaroside is also sensed by other organisms and has been shown to have a range of effects on many organisms, including bacteria, fungi, plants, and mammals (including humans). Ascaroside has the potential to be used as a human medicine, agrochemical, and for other diverse and valuable applications.

[0005] It has been demonstrated that, when applied to plants, ascaroside treatment exhibits the efficacy of increasing plant resistance to certain pathogens and / or inducing and triggering plant defense responses that can inhibit pathogen growth and / or infection. By activating and / or triggering the plant's innate defenses, ascaroside can thus prevent the proliferation of pathogens and / or protect crops from damage caused by various pathogens.

[0006] A unique characteristic of ascaroside is its high potency. Plants can respond to extremely low concentrations of ascaroside, therefore, the effective application rate required to trigger plant defense can be very low. This, in turn, poses challenges to grower convenience and supply chain logistics. This invention provides solutions to these challenges and related problems. Summary of the Invention

[0007] The inventors have discovered that the concentration of ascaridone in foliar sprays required to trigger or induce plant defense responses can be as low as 10 nanomoles per liter. This corresponds to a low single-digit ppb level concentration of ascaridone in the applied foliar spray. Furthermore, the inventors have found that applying excessively high concentrations of ascaridone to crop foliar surfaces can lead to a reduction in its beneficial effects. Therefore, there is an urgent need for practical and precise methods for applying these products at low concentrations. Achieving appropriately low application rates using pure ascaridone requires dissolving extremely small amounts (in some cases only a few milligrams) of ascaridone in containers filled with hundreds of liters of water. This type of measurement and mixing is impractical for growers, who often lack the equipment required to accurately measure and handle such small quantities. Moreover, ensuring that small amounts of solid ascaridone are completely and uniformly dissolved in large quantities of water can be difficult—pure ascaridone is solid and may be in fine powder form. This powdered ascaridone may not dissolve immediately upon addition to water and also tends to float on the surface and / or adhere to the edges of the container. These factors can lead to incomplete dissolution and / or inconsistent application rates.

[0008] One solution to this problem is to use pre-formulated liquid concentrates of ascaridone, which can be easily measured and mixed into agricultural spray cans. Many agricultural chemicals are supplied as liquid concentrates and are typically formulated so that growers use between about 1 / 2 and 16 liquid ounces per acre of crop treated (most commonly about 1 to 4 ounces per acre). Before field application, the appropriate volume of concentrate for the planted area to be treated is diluted with a suitable volume of water (usually in a large spray can) to create a spray solution that ensures a good foliage coverage rate (typically about 10-20 gallons per acre for row-planted crops) applied to the crop.

[0009] The inventors have determined that certain ascaridone foliar spray treatments are surprisingly effective when applied to field crops at extremely low application rates (5 mg to 100 mg / acre) via foliar spraying, and prototype liquid concentrate formulations of ascaridone have been developed that growers can conveniently apply using familiar methods to achieve these application rates. Such formulations are convenient to use and effective, but unfortunately, they are quite inefficient from a logistical perspective. For example, prototype ascaridone concentrates have been produced to allow for convenient application of ascaridone at ratios between approximately 25-100 mg / acre. This prototype is designed so that an application of 2 liquid ounces per acre will deliver 25 mg of ascaridone per acre. While this formulation is technically a concentrate, the solution is still very dilute compared to typical agrochemicals and contains less than 0.05% by weight of ascaridone. This approach is inefficient because the dispensing of such products requires the transportation and storage of large quantities of water.

[0010] This disclosure provides soluble solid ascaroside compositions that are easy for growers to use, but do not suffer from the inefficiency inherent in the aforementioned diluted liquid formulations. The provided soluble solid formulations are compatible with ascaroside and have a long shelf life, good handling characteristics, dissolve rapidly and completely in water, are compatible with other agrochemicals, and are biocompatible (e.g., non-toxic to plants, humans, or the environment).

[0011] In one embodiment, a soluble solid ascaridone composition is provided, which can be dissolved to conveniently produce a liquid ascaridone concentrate suitable for further dilution and application to crops. In one embodiment, the provided ascaridone composition comprises one or more ascaridones and a soluble solid carrier composition, wherein the ascaridone comprises 20% by weight or less of the one or more ascaridones. In some embodiments, the ascaridone composition comprises between about 1% by weight and about 20% by weight of the one or more ascaridones.

[0012] In another embodiment, a soluble solid ascaridone composition is provided, which can be dissolved to conveniently produce an easily sprayable formulation suitable for application to plants. In one embodiment, the provided composition comprises one or more ascaridones and a soluble solid carrier composition, wherein the ascaridone composition comprises 0.2% by weight or less of the one or more ascaridones. In some embodiments, the ascaridone composition comprises about 0.005% by weight to about 0.2% by weight of the one or more ascaridones.

[0013] The provided solid ascaroside composition is soluble in water and can be used to treat plants and crops. In some embodiments, the dissolution of the solid ascaroside composition provides a concentrated solution, which is further diluted before use. Detailed Implementation

[0014] This disclosure provides solid ascaroside compositions and methods of use, the solid ascaroside compositions comprising one or more ascarosides and a solid carrier composition. In some embodiments, the solid particulate composition comprises less than 20% by weight of one or more ascarosides. In other embodiments, the composition comprises less than 0.01% by weight of the one or more ascarosides. As used herein, the term "ascaroside" includes ascaroside, derivatives or analogs of ascaroside, or combinations thereof, as will be described in further detail herein.

[0015] ascaroside

[0016] Ascaroside is a secondary metabolite produced by nematodes. Many structurally diverse ascarosides have been identified in nature, and these ascarosides are believed to function as an evolutionarily conserved chemical language used by nematodes to control many aspects of their development.

[0017] Ascaroside is a derivative of ascaroside, a dideoxysugar lacking hydroxyl groups at positions 3 and 6. Ascaroside has the general structure shown in Formula I:

[0018]

[0019] (Formula I),

[0020] in:

[0021] Z represents C, which is arbitrarily substituted. 2-40 Aliphatic groups, and

[0022] R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., part-C(O)OR) c C 2-20 Carbamates (e.g., -partial-C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c 2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker. Among them, R... c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, wherein R a and R b Together they can form an optionally substituted ring, which optionally contains one or more heteroatoms and optionally contains one or more unsaturated sites.

[0023] In some implementations, Z is:

[0024] (i)–CH(CH3)–R 1, where R 1 C is arbitrarily substituted 1-40 Aliphatic groups

[0025] (ii)–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0026] (iii)–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0027] (iv)–CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0028] (v)–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0029] (vi)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0030] (vii)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0031] (viii)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 A heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker; or

[0032] (ix)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker.

[0033] In some implementations, Z is:

[0034] (x)–CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0035] (xi)–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0036] (xii)–CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0037] (xiii)–CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0038] (xiv)–(CH2) n –CON(R3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0039] (xv)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0040] (xvi)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0041] (xvii)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkages to another ascaridone molecule via bonds or carbon-containing linker portions; or

[0042] (xviii) Optionally unsaturated, optional substituted C 2-40 Side chains terminate at chain ends containing functional groups of nitrogen, oxygen, or sulfur.

[0043] As defined above and described herein, in some embodiments, Z includes a nitrogen-, oxygen-, or sulfur-containing functional group. It should be understood that "oxygen-containing functional group" refers to a portion containing one or more oxygen atoms (e.g., carbonyl groups, such as esters, aldehydes, carboxylic acids, orthoesters, and ketones; ethers, hydroxyl groups, and heterocycles containing one or more oxygen atoms and / or one of the aforementioned functional groups); "nitrogen-containing functional group" refers to a portion containing one or more nitrogen atoms (e.g., amines, amides, carbamates, imines, ureas, oximes, amidines, guanidines, nitriles, azo groups, azides, and heterocycles containing one or more nitrogen atoms and / or one of the aforementioned functional groups); and "sulfur-containing functional group" refers to a portion containing one or more sulfur atoms (e.g., thioethers, sulfones, sulfonic acids, sulfoxides, thiols, thiocyanates, or disulfides).

[0044] In some implementations, Z is optionally unsaturated, optionally substituted C 2-40 Side chains terminate at chain ends containing oxygen-containing functional groups. In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 A side chain terminating at a chain end containing a carboxylic acid. In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 Side chains that terminate at the aldehyde-containing chain end. In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 Side chain, terminating at the end containing the ester. In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 Side chain, which terminates at a point containing -CO2R 2 The chain end. In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 Side chains terminating at chain ends containing -CO2H. In some embodiments, Z is optionally unsaturated, optionally substituted C. 2-40 Side chains that terminate at chain ends containing -CO2CH3. In some embodiments, Z is optionally unsaturated, optionally substituted C 2-40 Sidechain, which terminates at a point containing -CON(R) 3 The chain end of )2. In some embodiments, Z is optionally unsaturated, optionally substituted C 2-40 Sidechains that terminate at points containing -N(R) 3 The chain end of )2. In some embodiments, Z is optionally unsaturated, optionally substituted C 2-40 Side chain, which terminates at the end of an ester containing a linker portion covalently attached to one or more other ascaroside molecules.

[0045] As described above, the sucralose moiety in the provided compound can be substituted or unsubstituted (i.e., the 2 and 4 positions of the sugar can have functional groups other than -OH, or in other words, the variable R in any of the formulas herein). a and / or R b It can be omitted (-H).

[0046] As defined above and described in this article, R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., part-C(O)OR) c C 2-20 Carbamates (e.g., -partial-C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c )2) The sugar moiety, peptide, polymer chain or the ascaroside molecule is linked to the ascaroside molecule via a bond or carbon-containing linker.

[0047] In some implementations, R a For –H. In some implementations, R b For –H. In some implementations, R a and R b Same. In some implementations, R a and R b All are -H. In some implementations, R a and R b Different. In some implementations, R a It is -H, and R b Not –H. In some implementations, R a Not –H and R b For –H. In some implementations, R a For –H and R b It is a para-hydroxybenzoic acid ester. In some embodiments, R a For –H and Rb It is an indole-3-carboxylic acid ester. In some embodiments, R a For –H and R b It is (E)-2-methyl-2-butyrate. In some embodiments, R a For –H and R b It is a pyridine carboxylate. In some embodiments, R a For –H and R b It is a nicotinic acid ester. In some embodiments, R a For –H and R b It is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutyrate. In some embodiments, R a -H and R b It is 4-((4-hydroxyphenylethyl)amino)-4-oxobutyrate. In some embodiments, R a It contains glycosides, amino acids, peptides, or nucleotides. In some embodiments, R b It contains glycosides, amino acids, peptides, or nucleotides. In some embodiments, R a It includes a link to a second ascaroside molecule. In some embodiments, R b It includes a link to an ascaroside molecule. In some embodiments, R a Contains sugar. In some implementations, R b It contains sugar.

[0048] In some implementation schemes, R a C is arbitrarily substituted 1-20 Aliphatic. In some implementations, R a C is arbitrarily substituted 1-6 Aliphatic. In some implementations, R a C 1-20 Aliphatic. In some implementations, R a C 1-6 Aliphatic. In some implementations, R a It can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl. In some embodiments, R a C 1-20 Acyl group. In some embodiments, R a -C(O)R c In some implementations, R a It is -C(O)H. In some implementations, R a It is -C(O)CH3. In some implementations, R a C is arbitrarily substituted 1-20 Aliphatic. In some implementations, R aC is arbitrarily substituted 1-6 Aliphatic. In some implementations, R a C 1-20 Aliphatic. In some implementations, R a C 1-6 Aliphatic. In some implementations, R a It is a optionally substituted 3- or 8-membered saturated or partially unsaturated heterocyclic group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R a It is an optionally substituted 8- or 12-membered saturated or partially unsaturated bicyclic heterocyclic group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R a The aryl group is optionally substituted. In some embodiments, R a The phenyl group is optionally substituted. In some embodiments, R... a It is phenyl. In some embodiments, R a Optionally substituted heteroaryl groups. In some embodiments, R a It is a optionally substituted 5- to 6-membered heteroaryl group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R a It is an optionally substituted 8- to 12-membered heteroaryl group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R a C is arbitrarily substituted 2-20 Carbonate. In some implementations, R a -C(O)OR c In some implementations, R a C is arbitrarily substituted 2-20 Carbamate. In some embodiments, R a -C(O)N(R) c )2. In some implementation schemes, R a C is arbitrarily substituted 2-20 Thioesters. In some implementations, R a -C(S)R c In some implementations, R a C is arbitrarily substituted 2-20 Thiocarbonate. In some embodiments, R a -C(S)OR c In some implementations, R a C is arbitrarily substituted 2-20 Dithiocarbonate. In some embodiments, R a -C(S)SR c In some implementations, Ra C is arbitrarily substituted 1-20 Thiocarbamate. In some embodiments, R a -C(S)N(R) c )2.

[0049] In some implementation schemes, R a The hydroxyl protecting group is optionally substituted. Suitable hydroxyl protecting groups are well known in the art and are included in those described in Protecting Groups in Organic Synthesis, TWGreene and PGM Wuts, 3rd edition, John Wiley & Sons, 1999. Examples of suitable oxygen protecting groups include, but are not limited to, acetyl, benzoylbenzyl, β-methoxyethoxymethyl ether (MEM), dimethoxytriphenylmethyl (DMT), methoxymethyl ether (MOM), methoxytriphenylmethyl (MMT), p-methoxybenzyl ether (PMB), methyl thiomethyl ether, pivaloyl, tetrahydropyranyl (THP), tetrahydrofuranyl (THF), triphenylmethyl, silyl ethers (e.g., trimethylsilyl (TMS), tert-butyldimethylsilyl (TBDMS), triisopropylsilyloxymethyl (TOM), and triisopropylsilyl (TIPS) ether), methyl ethers, and ethoxyethyl ethers. In some embodiments, R a For -OR c .

[0050] In some implementation schemes, R a The phosphorus-linked functional group is optionally substituted. It will be understood that, as used herein, "phosphorus-linked functional group" refers to a moiety containing one or more phosphorus atoms (e.g., phosphine, phosphate diester, phosphonic acid, phosphate ester). In some embodiments, R... a R is an optionally substituted sulfur-linked functional group. It will be understood that, as used herein, "sulfur-linked functional group" refers to a moiety containing one or more sulfur atoms (e.g., thioethers, sulfones, sulfonic acids, sulfoxides, thiols, thiocyanates, or disulfides). In some embodiments, R a The silicon-linked functional group is optionally substituted. It will be understood that, as used herein, "silicon-linked functional group" refers to a portion containing one or more silicon atoms (e.g., silanol, sulfoxide, siloxane, silyl ether, silyl chloride, silyl hydride, silene, or thiophene).

[0051] In some implementation schemes, R a For optionally substituted sugar portions. In some embodiments, R a The peptide is optionally substituted. In some embodiments, R aFor optionally substituted polymer chains. In some embodiments, R a This is via a bond or a carbon-containing linker to the ascaroside molecule. In some embodiments, R a C-type compounds containing ascaroside, optionally substituted 1-6 Aliphatic or mixed adipose.

[0052] In some implementation schemes, R b C is arbitrarily substituted 1-20 Aliphatic. In some implementations, R b C is arbitrarily substituted 1-6 Aliphatic. In some implementations, R b C 1-20 Aliphatic. In some implementations, R b C 1-6 Aliphatic. In some implementations, R b It can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl. In some embodiments, R b C 1-20 Acyl group. In some embodiments, R b -C(O)R c In some implementations, R b It is -C(O)H. In some implementations, R b It is -C(O)CH3. In some implementations, R b C is arbitrarily substituted 1-20 Aliphatic. In some implementations, R b C is arbitrarily substituted 1-6 Aliphatic. In some implementations, R b C 1-20 Aliphatic. In some implementations, R b C 1-6 Aliphatic. In some implementations, R b It is a optionally substituted 3- or 8-membered saturated or partially unsaturated heterocyclic group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R b It is an optionally substituted 8- or 12-membered saturated or partially unsaturated bicyclic heterocyclic group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R b The aryl group is optionally substituted. In some embodiments, R b The phenyl group is optionally substituted. In some embodiments, R... b It is phenyl. In some embodiments, R b Optionally substituted heteroaryl groups. In some embodiments, Rb It is a optionally substituted 5- to 6-membered heteroaryl group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R b It is an optionally substituted 8- to 12-membered heteroaryl group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R b C is arbitrarily substituted 2-20 Carbonate. In some implementations, R b -C(O)OR c In some implementations, R b C is arbitrarily substituted 2-20 Carbamate. In some embodiments, R b -C(O)N(R) c )2. In some implementation schemes, R b C is arbitrarily substituted 2-20 Thioesters. In some implementations, R b -C(S)R c In some implementations, R b C is arbitrarily substituted 2-20 Thiocarbonate. In some embodiments, R b -C(S)OR c In some implementations, R b C is arbitrarily substituted 2-20 Dithiocarbonate. In some embodiments, R b -C(S)SR c In some implementations, R a C is arbitrarily substituted 1-20 Thiocarbamate. In some embodiments, R b -C(S)N(R) c )2.

[0053] In some implementation schemes, R b The hydroxyl protecting group is optionally substituted. In some embodiments, R b For -OR c .

[0054] In some implementation schemes, R b The functional group is optionally substituted with a phosphorus-linked group. In some embodiments, R b R is an optionally substituted sulfur-linked functional group. In some embodiments, R b These are optional silicon-linked functional groups.

[0055] In some implementation schemes, R bFor optionally substituted sugar portions. In some embodiments, R a The peptide is optionally substituted. In some embodiments, R b For optionally substituted polymer chains. In some embodiments, R b This is via a bond or a carbon-containing linker to the ascaroside molecule. In some embodiments, R b C-type compounds containing ascaroside, optionally substituted 1-6 Aliphatic or mixed adipose.

[0056] In some implementation schemes, R a and R b Together they can form optionally substituted rings, which optionally contain one or more heteroatoms and optionally one or more unsaturated sites. In some embodiments, R a and R b Together, they can form optionally substituted 3- to 12-membered monocyclic or bicyclic saturated or partially unsaturated carbocyclic or heterocyclic rings having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R a and R b They can be combined to form optional substituted 5- to 12-membered monocyclic or bicyclic aryl or heteroaryl rings having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen or sulfur.

[0057] In some implementations, R a For –H and R b It is a para-hydroxybenzoic acid ester. In some embodiments, R a For –H and R b It is an indole-3-carboxylic acid ester. In some embodiments, R a For –H and R b It is (E)-2-methyl-2-butyrate. In some embodiments, R a For –H and R b It is a pyridine carboxylate. In some embodiments, R a For –H and R b It is a nicotinic acid ester. In some embodiments, R a For –H and R b It is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutyrate. In some embodiments, R a -H and R b It is 4-((4-hydroxyphenylethyl)amino)-4-oxobutyrate.

[0058] In some implementations, R a and R bAll are -H, and Z is selected from the formulas defined in (i) to (ix) above. In some implementations, R a and R b Both are -H, and Z conforms to equation (i) above. In some implementations, R a and R b Both are -H, and Z conforms to equation (ii) above. In some implementations, R a and R b Both are -H, and Z conforms to equation (iii) above. In some implementations, R a and R b Both are -H, and Z conforms to equation (iv) above. In some implementations, R a and R b Both are -H, and Z conforms to the above equation (v). In some implementations, R a and R b Both are -H, and Z conforms to the above equation (vi). In some implementations, R a and R b Both are -H, and Z conforms to the above equation (vii). In some implementations, R a and R b Both are -H, and Z conforms to the above equation (viii). In some implementations, R a and R b Both are -H, and Z conforms to the above equation (ix). In some implementations, R a and R b Both are -H, and Z conforms to the above equation (x). In some implementations, R a and R b Both are -H, and Z conforms to the above equation (xi). In some implementations, R a and R b Both are -H, and Z conforms to the above equation (xii). In some implementations, R a and R b Both are -H, and Z conforms to equation (xiii) above. In some implementations, R a and R b Both are -H, and Z conforms to the above equation (xiv). In some implementations, R a and R b Both are -H, and Z conforms to the above equation (xv). In some implementations, R a and R b Both are -H, and Z conforms to the above equation (xvi). In some implementations, R a and R b Both are -H, and Z satisfies the above formula (xvii).

[0059] As defined above and described in this article, each R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linked to another ascaridin molecule via a bond or carbon-containing linker.

[0060] In some implementation schemes, R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl.

[0061] In some implementation schemes, the R that appears c For -H. In some implementations, R c C is arbitrarily substituted 1-12 Aliphatic groups. In some implementations, R c C is arbitrarily substituted 1-6 Aliphatic groups. In some implementations, R c C is arbitrarily substituted 1-12 Heteroaliphatic groups. In some embodiments, R c C is arbitrarily substituted 1-6 Heteroaliphatic groups. In some embodiments, R c It is a optionally substituted 3- or 8-membered saturated or partially unsaturated heterocyclic group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R c It is an optionally substituted 8- or 12-membered saturated or partially unsaturated bicyclic heterocyclic group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R c The aryl group is optionally substituted. In some embodiments, R c The phenyl group is optionally substituted. In some embodiments, R... 2 It is phenyl. In some embodiments, R c Optionally substituted heteroaryl groups. In some embodiments, R c It is a optionally substituted 5- to 6-membered heteroaryl group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R c It is an 8- to 12-membered heteroaryl group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen or sulfur, which are optionally substituted.

[0062] As defined above and described in this article, R 2-H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker. In some embodiments, R 2 -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups or optionally substituted aromatic groups, optionally substituted heteroaryl groups.

[0063] In some implementation schemes, R 2 For -H. In some implementations, R 2 It is a metal cation. In some embodiments, R 2 It is an organic cation (e.g., a cation group centered on nitrogen or phosphorus). In some embodiments, R 2 C is arbitrarily substituted 1-20 Aliphatic group. In some embodiments, R 2 C is arbitrarily substituted 1-12 Aliphatic group. In some embodiments, R 2 C is arbitrarily substituted 1-8 Aliphatic group. In some embodiments, R 2 C is arbitrarily substituted 1-6 Aliphatic group. In some embodiments, R 2 Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl. In some embodiments, R 2 C is arbitrarily substituted 1-6 Aliphatic groups. In some implementations, R 2 C is arbitrarily substituted 1-20 Heteroaliphatic groups. In some embodiments, R 2 C is arbitrarily substituted 1-6 Heteroaliphatic groups. In some embodiments, R 2 It is a optionally substituted 3- or 8-membered saturated or partially unsaturated heterocyclic group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 2 It is an optionally substituted 8- or 12-membered saturated or partially unsaturated bicyclic heterocyclic group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 2 R is an optionally substituted aromatic group. In some embodiments, R 2 The phenyl group is optionally substituted. In some embodiments, R...2 It is phenyl. In some embodiments, R 2 Optionally substituted heteroaryl groups. In some embodiments, R 2 It is a optionally substituted 5- to 6-membered heteroaryl group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 2 It is an 8- to 12-membered heteroaryl group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen or sulfur, which are optionally substituted.

[0064] In some implementation schemes, R 2 Glycosides. It will be understood that a glycoside is a portion of a sugar that is linked to another functional group via a glycosidic bond.

[0065] In some implementation schemes, R 2 It is a nucleotide. In some implementations, R 2 It is adenosine monophosphate, cytidine monophosphate, guanosine monophosphate, or uridine monophosphate. In some embodiments, R 2 It is deoxyadenosine monophosphate, deoxycytidine monophosphate, deoxyguanosine monophosphate, or deoxythymidine monophosphate.

[0066] In some implementation schemes, R 2 This is for linkage to another ascaroside molecule via a bond or a carbon-containing linker. In some embodiments, R 2 C-type compounds containing ascaroside, optionally substituted 1-6 Aliphatic or mixed adipose.

[0067] In some implementations, R 2 It contains amino acids. In some implementations, R 2 It contains peptides.

[0068] As defined above and described in this article, each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linked to another ascaridone molecule via a bond or carbon-containing linker. In some embodiments, each R 3 Independently selected from -H and C 1-8 Aliphatic. In some implementations, an R 3 For -H and another R 3 Not -H. In some implementations, two Rs 3 None of them are -H. In some implementations, each R 3 All are -H. In some implementations, R appears. 3It is C that is arbitrarily substituted. 1-20 Aliphatic groups. In some embodiments, the R group appears... 3 C is arbitrarily substituted 1-6 Aliphatic groups. In some embodiments, the R group appears... 3 C is arbitrarily substituted 1-20 Heteroaliphatic groups. In some embodiments, the R group appears... 3 C is arbitrarily substituted 1-6 Heteroaliphatic groups. In some embodiments, R 3 It is a optionally substituted 3- or 8-membered saturated or partially unsaturated heterocyclic group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 3 It is an optionally substituted 8- or 12-membered saturated or partially unsaturated bicyclic heterocyclic group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 3 The presence of is an optionally substituted aryl group. In some embodiments, R 3 The phenyl group is optionally substituted. In some embodiments, R... 3 It is phenyl. In some embodiments, R 3 Optionally substituted heteroaryl groups. In some embodiments, R 3 It is a optionally substituted 5- to 6-membered heteroaryl group having 1 to 3 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur. In some embodiments, R 3 It is an 8- to 12-membered heteroaryl group having 1 to 4 independently selected heteroatoms chosen from nitrogen, oxygen or sulfur, which are optionally substituted.

[0069] In some implementations, at least one R 3 For -H. In some implementations, the two Rs 3 All groups are -H. In some embodiments, at least one R 3 C is arbitrarily substituted 1-20 Aliphatic groups. In some embodiments, the two R groups... 3 The group is an optionally substituted C 1-20 Aliphatic groups, which may be the same or different. In some embodiments, at least one R 3 C is arbitrarily substituted 1-12 Aliphatic group. In some embodiments, at least one R 3 C is arbitrarily substituted 1-8 Aliphatic group. In some embodiments, at least one R 3 C is arbitrarily substituted 1-6 Aliphatic group. In some embodiments, at least one R 3The compound is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl. In some embodiments, at least one R 3 It is -CH2CH2OH. In some embodiments, at least one R 3 -CH2CH2OR 2 Among them, R 2 It is as defined in the genera and subgenus herein. In some embodiments, at least one R 3 It is an optionally substituted aromatic group. In some embodiments, at least one R 3 Contains a glycoside. In some embodiments, at least one R 3 It contains amino acids. In some embodiments, at least one R 3 At least one R 3 Contains peptides. In some embodiments, at least one R 3 It contains nucleotides.

[0070] In some implementations, ascaroside is selected from the group consisting of:

[0071]

[0072] Where x is an integer from 1 to 22, and R a R b and R 2 Each of them is as defined above and in this text as a genus and subgenus.

[0073] In some implementations, ascaroside is selected from the group consisting of:

[0074]

[0075] Where x and R a and R b Each of them is as defined above and in this text as a genus and subgenus.

[0076] In some implementations, ascaroside is selected from the group consisting of:

[0077]

[0078] Where y is an integer from 1 to 20, and R a R b and R 2 Each of them is as defined above and in this text as a genus and subgenus.

[0079] In some implementations, ascaroside is selected from the group consisting of:

[0080]

[0081] Where y and R a and R b Each of them is as defined above and in this text as a genus and subgenus.

[0082] In some implementations, ascaroside is selected from the group consisting of:

[0083]

[0084] Where x and R 2 Each of them is as defined above and in this text as a genus and subgenus.

[0085] In some implementations, ascaroside is selected from the group consisting of:

[0086]

[0087] Where x is defined as above and as in this article as genus and subgenus.

[0088] In some implementations, ascaroside is selected from the group consisting of:

[0089]

[0090] Where y and R 2 Each of them is as defined above and in this text as a genus and subgenus.

[0091] In some implementations, ascaroside is selected from the group consisting of:

[0092]

[0093] Where y is defined as above and as in this article as genus and subgenus.

[0094] In some implementations, ascaroside is selected from the group consisting of:

[0095]

[0096] Where x and R a R b and R 3 Each of them is as defined above and in this text as a genus and subgenus.

[0097] In some implementations, ascaroside is selected from the group consisting of:

[0098]

[0099] Where x and R 3 Each of them is as defined above and in this text as a genus and subgenus.

[0100] In some implementations, ascaroside is selected from the group consisting of:

[0101]

[0102] Where y and R a R b and R 2 Each of them is as defined above and in this text as a genus and subgenus.

[0103] In some implementations, ascaroside is selected from the group consisting of:

[0104]

[0105] Where y and R 3 Each of them is as defined above and in this text as a genus and subgenus.

[0106] In the embodiments, the ascaroside available in the context of this disclosure has a universal structure (I), where Z is –CH(CH3)–(CH2). n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0107] In the embodiments, the ascaroside available in the context of this disclosure has a universal structure (I), where Z is –CH(CH3)–(CH2). n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0108] Specific ascarosides available in the context of this disclosure include, but are not limited to, ascr#7 and ascr#18.

[0109]

[0110] In some embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of: ASCII#9, ASCII#12, ASCII#14, ASCII#1, ASCII#10, ASCII#16, ASCII#18, ASCII#20, ASCII#22, ASCII#24, ASCII#26, ASCII#28, ASCII#30, ASCII#32, ASCII#34, and ASCII#36. In some embodiments, the ascaroside used in the provided methods is selected from the group consisting of: ASCII#10, ASCII#16, ASCII#18, ASCII#20, ASCII#22, and ASCII#24. In some embodiments, the ascaroside used in the provided methods is selected from the group consisting of: ASCII#9, ASCII#14, ASCII#10, and ASCII#18.

[0111] In some embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of: oscr#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In some embodiments, the ascaroside used in the provided methods is selected from the group consisting of: oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22. In some embodiments, the ascaroside used in the provided method is selected from the group consisting of: bhas#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In some embodiments, the ascaroside used in the provided method is selected from the group consisting of: oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

[0112] In some embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of: bhas#9, bhas#10, bhas#16, bhas#18, bhas#22, bhas#24, bhas#26, bhas#28, bhas#30, bhas#32, bhas#34, bhas#36, bhas#38, bhas#40, and bhas#42.

[0113] In some embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of: bhos#10, bhos#16, bhos#18, bhos#22, bhos#24, bhos#26, bhos#28, bhos#30, bhos#32, bhos#34, bhos#36, bhos#38, bhos#40, and bhos#42.

[0114] In some embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of: ascr#18, oscr#16, oscr#17, oscr#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.

[0115] In some embodiments, the 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.

[0116] In some embodiments, the ascaroside used in the provided methods and compositions is a blend comprising two or more of the following: ASCII#18, ASCII#17, ASCII#10, ASCII#3, ASCII#1, ASCII#7, and ASCII#9.

[0117] In some embodiments, the ascaroside used in the provided methods and compositions is a blend comprising two or more of the following: oscr#18, oscr#17, oscr#16, oscr#15, oscr#10, oscr#3, oscr#14, oscr#1, oscr#7, oscr#12, and oscr#9. In some embodiments, the ascaroside used in the provided methods and compositions is oscr#18. In some embodiments, the ascaroside used in the provided methods and compositions is oscr#16.

[0118] Ascaroside can be obtained from natural sources (e.g., nematodes) or prepared synthetically. Ascaroside can be prepared synthetically, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascaroside. Exemplary methods for preparing ascaroside include: providing 1-O-substituted rhamnose as a starting material; forming a monosulfonate ester at the 3-OH group of the starting material; and treating the monosulfonate ester with a hydride source to form 1-O-substituted ascaroside. In some embodiments, the formation of the monosulfonate ester is carried out on a substrate without a hydroxyl protecting group at the 2 or 4 position of the rhamnose starting material. In some embodiments, such methods include contacting the starting material with a sulfonating agent (i.e., a sulfonyl halide, sulfonic anhydride, or a similar agent) in the presence of a Lewis acid. Specific details regarding the synthesis of 1-O-substituted ascaroside can be found in International Publication No. WO 2022 / 024067, which is incorporated herein by reference.

[0119] ascaroside

[0120] In some embodiments, the ascaroside in the provided solid composition comprises an ascaroside salt. The ascaroside salt can be formed using suitable reagents, for example, at any suitable acidic or basic functional group on the ascaroside molecule.

[0121] In some embodiments, the provided salt has formula II':

[0122] [A] p - M p+ (Formula II)

[0123] Each of A, M, and p is defined and described below and in this document.

[0124] For example, in some embodiments, a salt of a carboxylic acid (also called a carboxylate) is provided. Such a salt can be described according to Formula II below, where “M” is a metal (or other cation) and “A” is the remaining portion of the ascaroside molecule attached to the carboxylic acid moiety (e.g., according to the structure of Formula I provided above):

[0125] [A-(C(O)O) - ] p M p+ (Formula II)

[0126] Where p represents an integer from 1 to 4. In some embodiments, p is 1, and the salt contains one ascaridin anion and one "M" cation (with a charge of +1). In some embodiments, p is 2, and the salt contains two ascaridin anions and one "M" cation (with a charge of +2). In some embodiments, p is 3, and the salt contains three ascaridin anions and one "M" cation (with a charge of +3). In some embodiments, p is 4, and the salt contains four ascaridin anions and one "M" cation (with a charge of +4). In embodiments where p is greater than 1, the ascaridin anions present in the salt may be the same or different.

[0127] Referring to the structure of ascaroside in Formula I above, it should be noted that the carboxylate can, for example, be in the "OR" of the tetrahydropyranyl ring. a "and / or "OR b "Formed at the substituent. In some embodiments, the carboxylic acid can be formed at the OR." a and / or OR b Formed at the substituent, wherein R a and / or R b –LC(O)OR c Where L is an optionally substituted divalent linker containing one or more carbon atoms and optionally one or more heteroatoms, and where R c For H. In some implementations, the carboxylic acid can be in OR a and / or OR b Formed at the substituent, wherein R a and / or R b This refers to a sugar moiety containing a carboxylic acid group (e.g., a sugar acid). In some embodiments, the carboxylic acid can be in the OR... a and / or OR b Formed at the substituent, wherein R a and / or R b This is a peptide containing a carboxylic acid group. In some embodiments, the carboxylic acid can be in the OR... a and / or OR b Formed at the substituent, wherein R a and / or R b This is a polymer containing a carboxylic acid group. In some embodiments, the carboxylic acid can be in the OR... a and / or OR b Formed at the substituent, wherein R c It is a polymer chain containing a carboxylic acid group. In some embodiments, the carboxylic acid can be in the OR... a and / or OR b Formed at the substituent, wherein R a and / or R b It is a monoester of a diacid. In some embodiments, such compounds are derived from R. aand / or R b Compounds with an -H atom react with cyclic anhydrides such as phthalic anhydride, succinic anhydride, maleic anhydride, or glutaric anhydride, or any of their substituted analogs. Representative examples of such ascaroside anions are shown below:

[0128]

[0129] Where x and R 2 Each of them is as defined above and in this text as a genus and subgenus.

[0130] Referring again to the structure of ascaroside in Formula I above, it should be noted that the carboxylic acid can be formed, for example, at the OZ substituent of the tetrahydropyranyl ring. In some embodiments, the carboxylic acid can be formed at the OZ substituent, for example, when Z is selected from –CH(CH3)–(CH2). n –CO2R 2 ;–CH(CH3)–(CH2) n –CH=CH-CO2R 2 –CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 ;–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 ;–(CH2) n –CO2R 2 ;–(CH2) n –CH=CH-CO2R 2 ; and –(CH2) n –CH(OH)–CH2-CO2R 2 When, where n is an integer from 1 to 40, and R 2 -H or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides containing carboxylic acid groups.

[0131] In some embodiments, the linker group -L- includes optionally substituted C. 1-20 aliphatic, C 1-20 Heteroaliphatic, aryl, or heteroaryl. Such connectors can be via ether linkage, ester linkage, carbonate linkage, or carbamate linkage (e.g., A-OC(O)NR). 3 -), thioester linkage (e.g., A-OC(S)-), thiocarbamate linkage (e.g., A-OC(S)NR) 3-), thiocarbonate linkage (e.g., A-OC(S)O-), dithiocarbonate linkage (thiocarbonate linkage (e.g., A-OC(S)S-), sulfonate linkage (e.g., A-OSO2-) or oxygen atoms attached to the ascaroside molecule via linkage through phosphorus atoms.

[0132] In one implementation, a salt is provided, for example, according to ascr#18 of the following formula:

[0133] (Formula IIb)

[0134] The negative charge is shown as delocalization on the oxygen atom of the carboxylic acid.

[0135] This disclosure is not limited to carboxylates of ascaroside. Salts that can be formed using other functional groups on the ascaroside molecule are also covered within this disclosure. For example, in ascaroside containing an amine group (e.g., in R...),... a R b In the case of (or Z-substituent), an ammonium salt can be formed with a suitable anionic group. Furthermore, in some embodiments, where ascaroside contains a hydroxyl (-OH) group, certain M groups can coordinate with it to form a salt, such as a borate or silicate derivative of ascaroside.

[0136] The following are non-restricted representative metal salts of ascaroside formed via carboxylic acid groups in the side chains:

[0137] Where x is defined as above and as in this article as genus and subgenus.

[0138] The following shows the "acid salts" of representative ascaroside formed by the hydroxyl groups of ascaroside:

[0139] Where x is defined as above and as in this article as genus and subgenus.

[0140] The composition of “M” (e.g., as shown in formulas 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 metals / Group 1 metals, alkaline earth metals / Group 2 metals, and transition metals. In some embodiments, M is a half-metal or non-metal selected from Group 1 elements. In some embodiments, M is an organic cation, such as ammonium ions, guanidine ions, amidine ions, pyridinium ions, phosphonium ions, sulfonium ions, or any similar nitrogen, phosphorus, or sulfur-centered cation or their analogues.

[0141] In some embodiments, M includes plant micronutrients or plant macronutrients. Plant micronutrients and macronutrients include, but are not limited to, nitrogen (N), phosphorus (P), potassium (K), calcium (Ca), magnesium (Mg), boron (B), silicon (Si), zinc (Zn), manganese (Mn), iron (Fe), copper (Cu), molybdenum (Mo), and nickel (Ni). Those skilled in the art will understand that not all such micronutrients and macronutrients can form salts with ascaroside in the same manner.

[0142] For example, in some embodiments, salts of phytonutrients such as potassium, calcium, magnesium, zinc, manganese, iron, copper, molybdenum, and nickel can be formed from carboxylic acids on ascaroside (e.g., according to formula II or IIb above). Nitrogen can be in the form of an ammonium or guanidine salt of ascaroside (e.g., where M is NH4). + or H2N + =C(NH2)2 or ammonium salts or guanidine salts analogues of ascaroside (e.g., where NH4) + or H2N + The phytonutrients, such as boron, silicon, and molybdenum, may not readily form salts with carboxylic acids, but can, for example, coordinate with the free OH groups present on the ascaroside molecule in the form of borates, silicates, or molybdates to form suitable salts. Therefore, in some embodiments, salts containing at least one boron atom coordinated with ascaroside, salts containing at least one silicon atom coordinated with ascaroside, or salts containing at least one molybdenum atom coordinated with ascaroside are provided.

[0143] Further details regarding ascaroside salts can be found in the international publication WO 2023 / 220174, submitted on 10 May 2023, which is incorporated herein by reference.

[0144] Solid ascaroside composition

[0145] Ascaroside can be applied to plants and crops in a variety of ways, and there are no particular limitations on the mode of application because plants can make a systemic response to ascaroside. Non-limiting examples of suitable modes of ascaroside application include seed treatment, foliar spraying or dusting, application via root soaking or saturation, application to soil, application of slow-release formulations, injection into stems or trunks, or application to compositions absorbed through the bark (e.g., on stems, trunks, branches, or vines). Most of these methods of applying ascaroside rely on the use of an aqueous solution of ascaroside.

[0146] In typical agricultural applications, the field application rate of ascaroside ranges from about 5 mg / acre to about 100 mg / acre, with 25 mg / acre to 50 mg / acre being preferred for most crops. At spray rates ranging from 5 gallons / acre to 50 gallons / acre, the required ascaroside concentration in the sprayer can will range from about 5 mg / 50 gallons (0.1 mg / galon) to about 100 mg / 5 gallons (20 mg / galon). Precise measurement of amounts less than 1 g is impractical in agricultural settings. Furthermore, even if subgram amounts of ascaroside could be measured, or subgram amounts of material could be supplied to growers (e.g., as a package), ensuring that less than 1 g of ascaroside is completely and uniformly dissolved in several gallons of water in a typical agricultural setting is extremely difficult, if not impossible.

[0147] One way to alleviate these problems is to supply liquid concentrates containing one or more ascarosides that can be easily dispensed into sprayer cans. In one embodiment, a concentrated solution of one or more ascarosides can be prepared in volumes ranging from 1 quart (1 L) to 2.5 gallons (10 L). For example, for an application rate of 25 mg / acre, an aqueous concentrate containing 422 mg of one or more ascarosides per liter provides a concentrate that would require approximately 2 oz. (60 mL) of concentrate per acre. For each acre treated, 2 oz. of concentrate is diluted in water (typically 5–20 gallons (19 L to 76 L)) for spraying. When packaged in a standard 2.5 gallon (10 L) can, this formulation provides enough to treat 160 acres of material, which meets growers’ expectations. Even in concentrate form, the solution contains only 422 ppm of ascarosides, of which 99.96% is water. The transport, storage, and dispensing of the concentrated form is cost-inefficient relative to the actual amount of ascarosides provided.

[0148] In one embodiment, a solid ascaroside composition comprising one or more ascarosides and a solid carrier composition can be dispensed without providing crop farmers / growers with a premixed aqueous concentrate. By providing a sufficient quantity of the 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 before or immediately before use). The transport of such a solid ascaroside composition would significantly reduce the transportation costs of ascarosides to growers, while providing growers with a composition that they can comfortably handle. This solid ascaroside formulation can be provided as granules (e.g., as a powder or granular composition) or in other solid forms such as tablets, flakes, or similar regular dense forms, each containing a specified amount of ascaroside.

[0149] In one embodiment, the provided solid ascaroside composition is a particulate composition comprising one or more ascarosides and a particulate carrier. The one or more ascarosides include, but are not limited to, any ascaroside or salt of ascaroside as described herein. The one or more ascarosides are blended with the particulate carrier composition. The particulate carrier provides additional volume to the ascaroside particulate composition, which facilitates the convenient preparation of highly diluted ascaroside solutions. Additionally, the particulate carrier composition may contain one or more compounds that enhance the solubility of the one or more ascarosides in water.

[0150] In one embodiment, the provided solid ascaroside composition comprises a tablet composition containing one or more ascarosides and a solid carrier formed into a dense shape. Preferably, such tablets have a specific weight and shape to allow for easy measurement of the target ascaroside dosage using an appropriate number of tablets. The one or more ascarosides include, but are not limited to, any ascaroside or salt of ascaroside as described herein. The provided tablets contain one or more ascarosides blended with the solid carrier composition and optionally a binder or coating necessary for forming a cohesive tablet. The carrier provides additional volume to the ascaroside composition, which facilitates the convenient preparation of highly diluted ascaroside solutions. Additionally, the tablet composition may contain one or more compounds that improve the solubility of the one or more ascarosides in water.

[0151] The concentration of one or more ascaridosin in the solid ascaridosin composition can be pre-selected according to the intended use. In some embodiments, the solid ascaridosin composition contains 20% by weight or less of the one or more ascaridosin. In other embodiments, the ascaridosin granule composition contains 15% by weight or less of the one or more ascaridosin; 10% by weight or less of the one or more ascaridosin; 5% by weight or less of the one or more ascaridosin; 2% by weight or less of the one or more ascaridosin; or 1% by weight or less of the one or more ascaridosin. In some embodiments, the solid ascaridosin composition contains between about 5% by weight and about 20% by weight of the one or more ascaridosin. In some embodiments, the solid ascaridosin composition contains between about 5% by weight and about 15% by weight of the one or more ascaridosin. In some embodiments, the solid ascaridosin composition contains between about 5% by weight and about 10% by weight of the one or more ascaridosin. In some embodiments, the solid ascaridosin composition contains between about 1% by weight and about 20% by weight of the one or more ascaridosin. In some embodiments, the solid ascaridone composition contains between about 10% and about 20% by weight of one or more ascaridones. In some embodiments, the solid ascaridone composition contains between about 10% and about 15% by weight of one or more ascaridones. In some embodiments, the solid ascaridone composition contains between about 15% and about 20% by weight of one or more ascaridones. The provided solid ascaridone composition containing between about 1% and about 20% by weight of one or more ascaridones is particularly useful for forming concentrated solutions of ascaridones intended for further dilution prior to use. This may be more convenient for growers than directly mixing the solid ascaridone formulation into the spray can, where it may be difficult to ensure complete dissolution of the solids in the spray can, especially when visibility in the spray can is poor and / or the option of vigorous mixing is limited. Such compositions are particularly convenient for preparing compositions for treating large-scale hydroponic systems, such as row-planted crop areas or commercial environments. In some embodiments, such solid ascaroside compositions can be provided in containers suitable for forming such concentrates: for example, a pre-measured amount of solids can be provided in a nearly empty 2.5-gallon pot, which can be filled with water on-site and before use to provide 2.5 gallons of liquid ascaroside concentrate for application at a rate of 1-4 liquid oz per acre.

[0152] To formulate a solution of ascaroside suitable for direct use without further dilution, a solid ascaroside composition is provided, containing less than about 0.5% by weight of one or more ascarosides. In some embodiments, such a composition contains less than about 0.4%, less than about 0.3%, less than about 0.25%, less than about 0.2%, less than about 0.15%, less than about 0.1%, less than about 0.05%, less than about 0.01%, or less than about 0.005% by weight of one or more ascarosides. In some embodiments, the solid ascaroside composition contains between about 0.005% by weight and about 1% by weight of one or more ascarosides. In some embodiments, the solid ascaroside composition contains between about 0.005% by weight and about 0.05% by weight of one or more ascarosides. In some embodiments, the solid ascaroside composition contains between about 0.005% by weight and about 0.5% by weight of one or more ascarosides. In some embodiments, the solid ascaroside composition contains one or more ascarosides at a concentration between about 0.005% by weight and about 0.1% by weight. In some embodiments, the solid ascaroside composition contains one or more ascarosides at a concentration between about 0.1% by weight and about 1% by weight. In some embodiments, the solid ascaroside composition contains one or more ascarosides at a concentration between about 0.05% by weight and about 1% by weight. In some embodiments, the solid ascaroside composition contains one or more ascarosides at a concentration between about 0.5% by weight and about 1% by weight. In some embodiments, the solid ascaroside composition contains one or more ascarosides at a concentration between about 0.05% by weight and about 0.5% by weight. In some embodiments, the solid ascaroside composition contains one or more ascarosides at a concentration between about 0.01% by weight and about 0.1% by weight. Ascaroside granule compositions containing one or more ascarosides at a concentration between about 0.01% by weight and about 0.1% by weight are particularly useful for forming ascaroside compositions that do not require further dilution before use. Such compositions are particularly convenient for preparing compositions for treating relatively small areas such as home gardens, indoor plants, lawns, or individual trees and shrubs. In some embodiments, such solid ascaroside compositions can be provided in containers suitable for forming liquid formulations on-site: for example, a pre-measured amount of solid can be provided in a 1-quart or 1-gallon spray bottle that can be filled with water on-site and sprayed directly onto the plants to provide an effective amount of ascaroside.

[0153] For the avoidance of any doubt, it should be understood that, in this disclosure, when referring to "weight%" in solid ascaroside compositions, "weight%" means the weight of the individual component relative to the total weight of the composition.

[0154] In some embodiments, the ascaroside in the provided solid ascaroside composition is present in salt form. The counterions of the ascaroside salt form may include elements that can also be used as phytonutrients. Phytonutrient 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). Phytonutrient elements may exist in cationic or anionic forms. These elements may be oxidized to form ionic forms.

[0155] In one embodiment, the carrier composition comprises one or more water-soluble fillers. Exemplary water-soluble fillers include, but are not limited to, carbohydrates, neutral inorganic salts, polyethylene glycol, and polypropylene glycol.

[0156] Exemplary carbohydrates that can be used as water-soluble fillers include, but are not limited to, lactose, glucose, fructose, mannose, mannitol, sucrose, powdered sugar, microcrystalline cellulose, starch, and powdered cellulose.

[0157] Exemplary neutral inorganic salts that can be used as water-soluble fillers include, but are not limited to, calcium nitrate, calcium chloride, copper phosphate (II), copper chloride (I), copper carbonate (II), copper iodide (I), ferric molybdate (II), potassium sulfate, potassium bromide, potassium chloride, potassium nitrate, magnesium nitrate, magnesium chloride, magnesium sulfate, sodium sulfate, sodium chloride, sodium nitrite, and sodium nitrate.

[0158] When used in ascaroside granule compositions, polyethylene glycol or polypropylene glycol should be solid at temperatures up to about 40°C, as described herein. For example, polyethylene glycol with an average molecular weight between about 3,000 and about 8,000 is generally suitable as a water-soluble filler. Polyethylene glycol and polypropylene glycol may have the additional benefit of improving the solubility of ascaroside in water. In one embodiment, the amount of polyethylene glycol and / or polypropylene glycol present in the granule carrier composition is sufficient to increase the solubility of the one or more ascarosides in water.

[0159] In one embodiment, the solid carrier composition in the provided solid ascaroside composition comprises one or more pH adjusters. The one or more pH adjusters that may be included in the carrier composition include pH lowering agents and pH raising agents. When dissolved in pure water, the pH lowering agent lowers the pH of the water. When dissolved in pure water, the pH raising agent raises the pH of the water.

[0160] Exemplary pH lowering agents include, but are not limited to, ammonium sulfate, calcium dihydrogen phosphate, copper nitrate (II), copper bromide (II), copper chloride (II), copper sulfate (II), boric acid, potassium dihydrogen phosphate, sodium sulfite, sodium dihydrogen phosphate, sodium bisulfite, sodium bisulfite, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium bisulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide.

[0161] Exemplary pH increasers include, but are not limited to, ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium bicarbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium bicarbonate (potassium bicarbonate), potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium bicarbonate (sodium bicarbonate), sodium hydroxide, ammonium bicarbonate, zinc hydroxide, and zinc carbonate.

[0162] In preferred embodiments, the pH-raising agent is a carbonate, bicarbonate, or phosphate. In some embodiments, the pH-raising agent is a bicarbonate. In some embodiments, the pH-raising agent contains one or more carbonates, bicarbonates, or phosphates. In some embodiments, the pH-raising agent contains one or more carbonates. In some embodiments, the pH-raising agent contains one or more bicarbonates. In some embodiments, the pH-raising agent contains one or more phosphates. In some embodiments, the pH-raising agent comprises sodium bicarbonate and potassium bicarbonate. In some embodiments, the pH-raising agent is sodium bicarbonate. In some embodiments, the pH-raising agent is potassium bicarbonate. Besides acting as pH-raising agents, carbonates, bicarbonates, and phosphates can also be used to buffer soil pH to prevent acidification. Additionally, carbonates can chelate heavy metals in the soil surrounding plants. Phosphates are used as fertilizers to promote plant growth and development.

[0163] In some embodiments, the solid ascaroside composition contains between about 80% by weight and about 99% by weight of a pH-raising agent. In some embodiments, the solid ascaroside composition contains between about 80% by weight and about 95% by weight of a pH-raising agent. In some embodiments, the solid ascaroside composition contains between about 80% by weight and about 90% by weight of a pH-raising agent. In some embodiments, the solid ascaroside composition contains between about 99% by weight and about 99.995% by weight of a pH-raising agent. In some embodiments, the solid ascaroside composition contains between about 99% by weight and about 99.95% by weight of a pH-raising agent. In some embodiments, the solid ascaroside composition contains between about 99% by weight and about 99.9% by weight of a pH-raising agent.

[0164] In some embodiments, the advantage of a pH-raising agent is that increasing the pH of the solution can increase the solubility of ascaroside having a carboxylic acid moiety. Additionally or alternatively, if the ascaroside is in salt form, using a pH-raising agent can help maintain the salt form of the ascaroside if the water used to prepare the composition is acidic.

[0165] In some embodiments, the provided solid ascaridone composition comprises one or more ascaridones, wherein the solid ascaridone composition is characterized in that the one or more ascaridones exhibit a water solubility of at least 1, 3, 6, 9, 12, 15, 20, or 25 g / gal. In some embodiments, the provided solid ascaridone composition comprises one or more ascaridones, wherein the solid ascaridone composition is characterized in that the one or more ascaridones exhibit a water solubility of at least 0.1, 1, 10, 50, or 100 mM. In some embodiments, the provided solid ascaridone composition comprises one or more ascaridones, wherein the solid ascaridone composition is characterized in that the one or more ascaridones exhibit a water solubility of at least 0.2, 0.3, 0.4, 0.5, 0.75, or 1 M. In some embodiments, the solubility is measured at room temperature (e.g., 25°C).

[0166] In some embodiments, the provided solid ascaroside composition comprises one or more ascarosides, wherein the solid ascaroside composition is characterized in that the one or more ascarosides exhibit a water solubility at least 50%, 75%, 100%, 1,000%, 5,000%, or 10,000% higher than that of a reference. In some embodiments, the reference is a corresponding composition containing only the one or more ascarosides.

[0167] Ascaroside containing carboxylic acids can react with pH-raising agents (such as carbonates) to form carboxylate salts. The carboxylate salts of ascaroside have increased water solubility. Using pH-raising agents has the advantage of promoting in-situ salt formation from ascaroside containing carboxylic acids. In some embodiments, the solid ascaroside composition consists essentially of or comprises one or more ascarosides and carbonates. In some embodiments, the solid ascaroside composition consists essentially of or comprises one or more ascarosides and bicarbonates. In some embodiments, the solid ascaroside composition consists essentially of or comprises one or more ascarosides and phosphates. In some embodiments, such carbonates, bicarbonates, or phosphates contain potassium, sodium, or quaternary ammonium cations. The solid ascaroside composition may contain one or more ascarosides, one or more water-soluble fillers, and one or more pH adjusters.

[0168] In some embodiments, the solid ascaroside composition is substantially composed of one or more ascarosides and sodium bicarbonate. In some embodiments, the solid ascaroside composition is substantially composed of one or more ascarosides and potassium bicarbonate. In some embodiments, the solid ascaroside composition is composed of one or more ascarosides and sodium bicarbonate. In some embodiments, the solid ascaroside composition is composed of one or more ascarosides and potassium bicarbonate.

[0169] 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.

[0170] In some implementations, this disclosure provides for including

[0171] A solid ascaroside composition of one or more ascarosides, and

[0172] An apparatus for dissolving one or more ascarosides in water at a concentration of at least about 0.1, 1, 10, 50 or 100 mM.

[0173] In some implementations, this disclosure provides for including

[0174] A solid ascaroside composition of one or more ascarosides, and

[0175] An apparatus for dissolving 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.

[0176] In some implementations, this disclosure provides for including

[0177] A solid ascaroside composition of one or more ascarosides, and

[0178] An apparatus for dissolving one or more ascarosides in water at a concentration of at least about 1, 3, 6, 9, 12, 15, 20 or 25 g / gal.

[0179] In some embodiments, the device for dissolving the one or more ascarosides includes a pH adjuster. In some embodiments, the device for dissolving the one or more ascarosides includes a pH enhancer. In some embodiments, the solubility is measured at room temperature (e.g., 25°C).

[0180] In some implementations, this disclosure provides for including

[0181] A solid ascaroside composition of one or more ascarosides, and

[0182] A device for enhancing the solubility of one or more ascarosides (e.g., in water).

[0183] In some embodiments, the device for enhancing the solubility of the one or more ascarosides includes a pH adjuster. In some embodiments, the device for enhancing the solubility of the one or more ascarosides includes a pH enhancer. 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% compared to a reference. In some embodiments, the solubility is measured at room temperature (e.g., 25°C).

[0184] In some implementations, this disclosure provides for including

[0185] A solid ascaroside composition of one or more ascarosides, and

[0186] An apparatus 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.

[0187] In some implementations, this disclosure provides for including

[0188] A solid ascaroside composition of one or more ascarosides, and

[0189] An apparatus 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.

[0190] In some implementations, this disclosure provides for including

[0191] A solid ascaroside composition of one or more ascarosides, and

[0192] An apparatus 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 g / gal.

[0193] In some embodiments, the device for providing the aqueous ascaroside composition includes a pH adjuster. In some embodiments, the device for providing the aqueous ascaroside composition includes a pH enhancer. In some embodiments, solubility is measured at room temperature (e.g., 25°C).

[0194] It has been found that microorganisms, including fungi and molds, can grow in aqueous ascaridone solutions containing the aforementioned aqueous ascaridone concentrate. This can be addressed by packaging such solutions under aseptic conditions. However, problems still arise when the packaging of such solutions is opened and stored in non-sterile environments (e.g., on a farm), as the shelf life of the product may be compromised after opening. This is another disadvantage of providing commercial ascaridone formulations in diluted aqueous solution form. Solutions produced by the solid ascaridone formulations provided herein have been found to have greater resistance to microbial contamination than pure ascaridone solutions. Fungal growth can be reduced or inhibited in such solutions, particularly when using pH adjusters that raise the pH of the ascaridone solution. In some embodiments, solid ascaridone compositions are provided that, when dissolved in water, provide ascaridone solutions with enhanced resistance to microbial contamination or growth (e.g., mold or fungal growth). In some embodiments, such compositions comprise one or more ascaridones and one or more pH adjusters that raise the pH of the resulting solution. In some embodiments, such pH enhancers are provided in a molar excess relative to any acidic functional group of ascaroside, such that when the composition is dissolved in water, the ascaroside solution has a pH greater than 7 (e.g., greater than 7.5, greater than 8, greater than 8.5, greater than 9, or greater than 9.5).

[0195] Solid ascaroside compositions can be prepared using any technique for dry mixing. Dry mixing techniques include, but are not limited to, dry mixing, dry granulation, wet granulation, melt granulation, high-shear mixing, and low-shear mixing. Solid ascaroside granular compositions can be formed into granular materials by known methods, including the use of binders, granulation, etc. Powder formulations can maintain the material in a free-flowing form by including anti-caking agents or moisture control additives. Solid ascaroside compositions comprising tablets, pills, flakes, spheres, or similar regular solid forms can be prepared by known methods, including compression, molding, extrusion, etc. Such compositions can have their appearance, handling characteristics, or stability improved by incorporating binders to aid adhesion of the material in solids and / or coatings.

[0196] Granulation is generally a process of adhering powder particles together to form granules. Granulation can be used because it produces a relatively uniform mixture of particles of different sizes. Dry granulation processes can be used to form ascaroside granule compositions without the use of liquid solutions. Dry granulation can be carried out on presses using heavy impact tools or on roller presses commonly known as chilsonators.

[0197] Wet granulation involves forming granules using a granulating fluid or wetting agent, which is then removed by drying. Examples of suitable solvents include, but are not limited to, acetone, methanol, ethanol, diethyl ether, ethyl acetate, chlorinated solvents, or mixtures thereof. Granulators can be low-shear, medium-shear, or high-shear. Shear force is the amount of mechanical force applied by the granulator. Low-shear granulators use very small mechanical forces to agglomerate powders. Fluidized bed granulators use a high-flow-rate airflow to suspend powders in a chamber for mixing. Fluidized bed granulators do not impart mechanical energy but rely on powder characteristics and a binding solution to form slightly bound powders into granules. After the granulation process is complete, the resulting mixture can be dried to remove at least a portion of the solvent.

[0198] Melt granulation is a process in which powder transforms into solid aggregates or agglomerates when heated. It is similar to wet granulation, except that the binder only acts as a wetting agent after melting.

[0199] Uses of solid ascaroside compositions

[0200] Solid ascaroside compositions disclosed herein are typically dissolved in water to form a solution containing one or more ascarosides. In one embodiment, the solid ascaroside composition is provided to the user in a container. Examples of containers include, but are not limited to, cylinders, cans, drums, bottles, bags, or pouches. Containers may be made of polymer, glass, or metal. Ascaroside granule compositions are typically accompanied by instructions on how to prepare a solution from the solid ascaroside composition. Such instructions may include the amount of the ascaroside granule composition (e.g., by weight or by volume) and the amount of water to which the solid ascaroside composition is added. For example, the instructions may include the weight of the ascaroside granule composition per gallon of water. In another example, the instructions may include the volume of the ascaroside granule composition per gallon of water. To aid mixing, a spoon designed to contain a suitable amount of the ascaroside granule composition for a predetermined volume of water may be provided.

[0201] Alternatively, the ascaroside granule composition may be packaged in a single-use container. In one embodiment, the single-use container may include sufficient ascaroside granule composition to be added to a predetermined amount of water. For example, the single-use container may include sufficient ascaroside composition to be added to one gallon (3.8 L) of water. The single-use container may include instructions for adding the entire contents of the ascaroside container to a separate container containing an appropriate amount of water.

[0202] Single-use containers can be designed to form concentrated ascaroside solutions. As used herein, a “concentrated solution” refers to a solution of one or more ascarosides in water, wherein the concentration of ascarosides is greater than the concentration of ascarosides required for administration in the water. The concentrated solution needs to be diluted before use. In some embodiments, the ascarosides in the single-use container are intended to be added to between about 1 quart (e.g., a 1-quart bottle) and about 300 gallons (e.g., an IBC tote bag). In some embodiments, the provided solid ascaroside composition is packaged in a single-use package sufficient to produce a concentrated ascaroside solution when dissolved in a bottle or drum (e.g., having a volume of about 0.5 gallons (1.9 L), about 1.0 gallon (3.8 L), about 1.5 gallons (5.7 L), about 2.0 gallons (7.6 L), about 2.5 gallons (9.5 L), about 3 gallons (11.4 L), 4 gallons (15.1 L), or 5 gallons (18.9 L)). In some embodiments, the provided solid ascaroside composition is packaged in a single-use package sufficient to produce a concentrated ascaroside solution when dissolved in a drum or can (e.g., a plastic or metal drum having a volume of about 10 gallons, about 20 gallons, about 30 gallons, or about 55 gallons, or an IBC tote bag having a volume of about 110 gallons, about 120 gallons, about 140 gallons, about 180 gallons, about 220 gallons, about 250 gallons, about 275 gallons, about 300 gallons, about 330 gallons, about 350 gallons, about 450 gallons, or about 550 gallons). According to the provided instructions, the concentrated solution obtained by dissolving the solid ascaroside composition typically has an ascaroside concentration of about 0.05 mM to 10 mM.

[0203] Generally, the amount of solid ascaridone composition added to the concentrate should not exceed the solubility of the components of the solid ascaridone composition. In some embodiments, the provided solid ascaridone composition has ascaridone contents and associated instructions for use, such that the concentrated ascaridone solution obtained by dissolving the provided solid ascaridone composition according to the instructions has a concentration such that applying about 0.5 liquid ounces (15 mL) to about 8 ounces (240 mL) of the concentrate per acre of crop to be treated (e.g., after further dilution to an appropriate spray volume) provides effective application of ascaridone to the crop (e.g., to reduce pathogen damage to the crop). In some embodiments, the provided solid ascaridone composition is formulated such that the solid dissolves in the range of about 1 tablespoon (15 mL) / 5 gallons to about 1 / 2 cup (120 mL) / gallon (high concentration). This provides a good balance between grower convenience (easy to measure and rapidly dissolve the amount) and logistical efficiency (minimizing the storage and transport of inert components). In some embodiments, the provided solid ascaroside composition is formulated such that dissolution of approximately 1 tablespoon (15 mL) of solid per gallon provides a concentrated solution.

[0204] Single-use containers can also be designed to contain a quantity of ascaridin such that the dissolution of all contents provides an ascaridin solution with a concentration approximately required for application to plants, without further dilution. For example, a single-use product can be provided in a quantity suitable for row crop growers, such that the entire contents of a single-use package can treat several acres (e.g., 1-100 acres) when added directly to a spray can. Such single-use packaging can also be offered to small growers or home gardeners: when its entire contents are dissolved in a small volume of water (e.g., 0.5 to 5 gallons), the package provides a volume of ready-to-spray solution that still conveniently delivers an effective amount of ascaridin when applied to smaller areas such as gardens or individual plants. According to the provided instructions, the ready-to-use solution obtained by dissolving the solid ascaridin composition typically has an ascaridin concentration of about 25 nM to about 10 μM. In some embodiments, the provided solid ascaroside composition is formulated such that the dissolution of about 1 tablespoon (15 mL) of solid per gallon provides a solution with an ascaroside concentration of 1 μmol / L. In some embodiments, the provided solid ascaroside composition is formulated such that the dissolution of about 1 tablespoon (15 mL) of solid per gallon provides a solution with an ascaroside concentration of 5 μmol / L. In some embodiments, the provided solid ascaroside composition is formulated such that the dissolution of about 1 tablespoon (15 mL) of solid per gallon provides a solution with an ascaroside concentration of 100 μmol / L.

[0205] In an alternative embodiment, the solid ascaroside composition can be dispensed to the end user in a substantially empty container configured to hold a predetermined volume of water. The instructions only include guidance on adding an appropriate amount of water to the container. The container can be designed to form a concentrated solution of the ascaroside granule composition. Alternatively, the container can be designed to form a ready-to-use ascaroside solution with an appropriate ascaroside concentration after water is added to the container.

[0206] Formulations may additionally contain "adjuvant surfactants" to enhance the deposition, wetting, and penetration of the compound on target crops and organisms. These "adjuvant surfactants" may be used as components of the composition. The amount of adjuvant surfactants typically varies from 0.01 to 1.0% by weight, preferably from 0.05 to 0.5% by weight. Suitable adjuvant surfactants include, but are not limited to, ethoxylated nonylphenol, ethoxylated synthetic or natural alcohols, esters or sulfosuccinic acid salts, ethoxylated silicones, ethoxylated fatty amines, blends of surfactants with mineral or vegetable oils, crop oil concentrates (mineral oil (85%) + emulsifier (15%)); nonylphenol ethoxylates; benzyl cocoyl dimethyl quaternary ammonium salts; blends of petroleum hydrocarbons, alkyl esters, organic acids, and anionic surfactants; C9-Cu alkyl polysaccharides; phosphorylated alcohol ethoxylates; natural primary alcohols (C9-Cu alkyl polysaccharides); and natural primary alcohols (C9-Cu alkyl polysaccharides). 12-C 16 Ethoxylated compounds; di-sec-butylphenol EO-PO block copolymer; methyl-terminated polysiloxane; nonylphenol ethoxylated compound + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylated compound (8EO); tallow amine ethoxylated compound (15EO); PEG (400) dioleate-99. Formulations may also include oil-in-water emulsions.

[0207] In the case of wettable formulations, the "surfactant" may comprise about 0.5% to about 10% of the composition. Suitable "surfactants" for wettable powders include sulfonated lignin, condensed naphthalene sulfonates, naphthalene sulfonates, alkylbenzene sulfonates, alkyl sulfonates, or nonionic surfactants such as ethylene oxide adducts of alkylphenols or mixtures thereof.

[0208] Representative organic solvents that can be used to prepare solutions from solid ascaroside compositions are aromatic liquids, such as xylene, propylbenzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, especially dimethyl amides and diol derivatives of fatty glycols such as n-butyl ether, diethyl ether, or methyl ether of diethylene glycol, methyl ether of triethylene glycol, amides of simple carboxylic acids such as dimethylformamide and dimethylacetamide, petroleum fractions or hydrocarbons such as mineral oils, aromatic solvents, paraffin oils, etc.; terpene solvents, rosin derivatives, aliphatic ketones such as cyclohexanone, complex aliphatic and aromatic alcohols such as 2-ethoxyethanol, vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, etc.; esters of the above vegetable oils; etc. Mixtures of two or more organic liquids can also be used to prepare emulsifiable concentrates. Organic liquids include xylene and propylbenzene fractions, with xylene being the preferred choice in some cases.

[0209] "Emulsifiers" used for emulsifiable concentrates are typically mixtures of ionic and / or nonionic surfactants, such as those mentioned herein or their equivalents. Examples of nonionic emulsifiers that can be used to prepare emulsifiable concentrates include polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, fatty alcohols, fatty amines, or fatty acids with ethylene oxide or propylene oxide, such as ethoxylated alkylphenols and carboxylic acid esters solubilized with polyols or polyoxyethylenes. Cationic emulsifiers include quaternary ammonium salts and fatty amine salts. Anionic emulsifiers include oil-soluble salts of alkyl aryl sulfonic acids (e.g., calcium), oil-soluble salts, or suitable salts of sulfated and phosphorylated polyethylene glycol ethers.

[0210] The compositions described herein may contain one or more inert carriers. Examples of inert carriers include, but are not limited to, pyrophyllite, talc, chalk, gypsum, bleaching clay, bentonite, palygorskite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, purified silicates, etc.

[0211] An "aqueous suspension" of a solid ascaroside composition can be prepared, wherein the composition is dispersed in an aqueous medium at a concentration typically ranging from about 5% to about 50% by weight. The suspension is prepared by finely grinding the solid ascaroside composition and vigorously mixing it with a medium of water, a surfactant, and a dispersant. Inert components such as inorganic salts and synthetic or natural gums can also be used to increase the density and / or viscosity of the aqueous medium as needed.

[0212] In some aspects, this disclosure provides methods for preparing ready-to-use ascaroside compositions, these methods comprising:

[0213] Provide solid ascaroside compositions as defined and described above and in this document;

[0214] The solid ascaroside composition is combined with a liquid solvent (e.g., water) at a first concentration; and

[0215] Further add a liquid solvent (e.g., water);

[0216] The solid ascaroside composition contains 20% by weight or less of one or more ascarosides.

[0217] In some aspects, this disclosure provides methods for preparing ready-to-use ascaroside compositions, these methods comprising:

[0218] Provide solid ascaroside compositions as defined and described above and herein; and

[0219] The solid ascaroside composition is combined with a liquid solvent (e.g., water) at a first concentration;

[0220] The solid ascaroside composition contains 0.2% by weight or less of one or more ascarosides.

[0221] Example

[0222] Example 1. Formulation and use of a solid granular ascaroside composition for agricultural applications: A solid ascaroside composition consisting of ASICS#18 sodium bicarbonate was formulated by combining 10 grams of ascaroside in fine powder form and 70 grams of sodium bicarbonate in fine powder form. The mixture was placed in an industrial blender and homogenized for 1 minute. The resulting powder was packaged in a polyethylene wide-mouth bottle comprising a measuring cup (e.g., a spoon) with a volume of 1 tablespoon (15 mL). For field use, one level spoonful of the solid ascaroside composition was measured using the measuring cup and dissolved in 1 gallon (3.8 L) of water to form a concentrated solution. The concentrated solution was added to a spray can at a ratio of 2 liquid ounces per acre of crop to be treated. One gallon of solution treated 64 acres of crop and delivered an effective application rate of approximately 25 mg of ASICS#18 per acre.

[0223] Example 2. Formulation and use of an alternative solid granular ascaroside composition for agriculture: A solid ascaroside composition consisting of ASICS#18 and potassium bicarbonate was formulated by combining 100 g of ascaroside in fine powder form and 700 g of potassium bicarbonate in fine powder form. The mixture was placed in an industrial blender and homogenized for 1 minute. The resulting powder was packaged in a polyethylene wide-mouth bottle containing a measuring cup (e.g., a spoon) with a volume of 1 tablespoon (15 mL). For field use, one level spoonful of the solid ascaroside composition was measured using the measuring cup and dissolved in 1 gallon (3.8 L) of water to form a concentrated solution. The concentrated solution was added to a spray can at a ratio of 2 liquid ounces per acre of crop to be treated. One gallon of solution treated 64 acres of crop and delivered an effective application dose of approximately 25 mg of ASICS#18 per acre. The formulation also delivered a small amount of potassium nutrient to the treated crop.

[0224] Example 2b. Formulation and use of an alternative solid particle ascaroside composition for agriculture: A mixture was formed as described in Example 2, except that potassium bicarbonate was replaced with a commercial formulation (MilStop™ SP) containing additional components such as an anti-caking agent and a surfactant. The product of Example 2 tended to clump together, making it difficult to remove from the packaging and difficult to measure accurately. In contrast, the product of Example 2b remained as a free-flowing powder, facilitating measurement and dissolution.

[0225] Example 3. Comparison of solubility of pure ascaroside and the provided solid ascaroside composition: Two one-gallon plastic containers were filled 1 / 3 full with clean tap water. One spoonful of the composition described in Example 1 was added to the first container. The solid sank to the bottom of the container and dissolved within 30 seconds of gentle mixing with a polyethylene paddle. 1.5g of pure ASICS#18 powder was added to the second container. Some ascaroside floated as fine particles on the surface of the water, while some ascaroside formed clumps. After vigorous mixing for several minutes, the mixture was allowed to dissolve slowly, but the solid remained visible, and some ascaroside adhered to the sides of the container and the polyethylene paddle at the water level. Each container was then filled with additional clean water to a total of 1 gallon. The solution from the provided solid formulation remained clear and colorless, with no visible solids present. The solution obtained by directly adding ascaroside still contained solids visible at the bottom of the container and adhered to the sides.

[0226] Example 4. Comparison of stability of solutions obtained from pure ascaroside or the provided solid ascaroside composition: A 100 mL fraction of the 1-gallon concentrate produced in Example 1 and a 100 mL fraction of a comparative concentrate produced by dissolving 1.5 g of pure ascaroside in 1 gallon of sterile water were placed in polyethylene bottles and contaminated with fungal spores. The containers were capped and left at room temperature for 4 weeks. The solution obtained from the solid ascaroside composition showed no change in appearance or signs of fungal growth, while the solution obtained directly from ascaroside became cloudy and contained visible fungal growth suspended in it.

[0227] Example 5. Formulation and use of an ascaroside tablet composition for agricultural use: A solid ascaroside composition consisting of ASICS#18 and potassium bicarbonate was formulated by combining 100 g of ascaroside in fine powder form and 850 g of potassium bicarbonate in fine powder form. The mixture was placed in an industrial blender and homogenized for 1 minute. Then 50 g of polyvinylpyrrolidone was added to the blender, and the mixture was further homogenized for 30 seconds. The resulting mixture was divided into 5 g portions. Each portion was then formed into tablets using a high-pressure press with suitable molds and dies. The resulting tablets were stored in polyethylene wide-mouth bottles. For field use, one tablet was placed in one quart of water and stirred until dissolved. This quart concentrate was then added to a spray can for application to 20 acres of crop. Each tablet treated 20 acres of crop to deliver an effective application dose of 25 mg / acre of ASICS#18, or treated 10 acres of crop at an effective application dose of 50 mg / acre. The formulation also delivers a small amount of potassium nutrient to the treated crop.

[0228] Example 6. In another example, an application rate of 25 mg ascaroside per acre is required. To treat 160 acres at this application rate, 4000 mg (4 g) of ascaroside is needed. An ascaroside granular composition comprising 20% ​​ascaroside / 80% granular carrier composition is prepared by mixing 4 g of ascr#18 and 50 g of sodium bicarbonate (NaHCO3). The increased volume of the granular carrier makes the composition easier to measure for the user, while reducing transportation costs associated with large-volume or water transport. The use of sodium bicarbonate in the granular carrier composition aids in the dissolution of ascr#18, as this ascaroside has higher solubility in alkaline solutions.

[0229] Example 7. Formulation and Use of a Solid Ascaroside Granule Composition for Residential Applications: A solid ascaroside composition consisting of ASICS#18 and potassium bicarbonate was formulated by combining 32 mg of ascaroside in fine powder form and 500 g of potassium bicarbonate in fine powder form. The mixture was placed in an industrial blender and homogenized for 5 minutes. Ten 0.10 g samples were taken from the mixture, and the mixture was stirred between each sample to ensure that the sample represented the bulk composition. The sample was dissolved in water and analyzed by HPLC-MS, which revealed a consistent amount of ascaroside, indicating that the solid mixture was homogeneous. The resulting powder was then packaged in a polyethylene wide-mouth bottle containing a measuring cup (e.g., a spoon) with a volume of 1 tablespoon (15 mL). In use, a level spoonful of the solid ascaroside composition was measured using the measuring cup and dissolved in 1 gallon (3.8 L) of water to form a spray-on solution. The solution had an ascaroside concentration of approximately 1 μmol / L, which is effective for the control of pathogens in most tested plants.

[0230] definition

[0231] To facilitate understanding of this disclosure, certain terms are defined below. Further definitions for these and other terms are set forth throughout the specification. In this application, unless clearly apparent from the context, the term "an" or "a" may be understood to mean "at least one / a kind".

[0232] As used in this application, the term "or" can be understood to mean "and / or". In this application, the terms "comprising" and "including" can be understood to cover the listed components or steps, whether presented alone or together with one or more other components or steps. As used in this application, the term "comprise" and variations thereof (such as "comprising" and "comprises") are not intended to exclude other additives, components, wholes, or steps.

[0233] About, approximately: As used herein, the terms “about” and “approximately” are used equivalently. Unless otherwise stated, the terms “about” and “approximately” are to be understood as allowing for standard variations as would be understood by one of ordinary skill in the art. Where the scope provided herein includes endpoints. Any numbers used in this application with or without “about” are intended to cover any normal fluctuations as understood by one of ordinary skill in the relevant art. Unless otherwise stated, the above terms refer to within 25% of a given value. In some embodiments, the terms “about” or “approximately” refer to a range of values ​​that are 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1% or less of the reference value in either direction, unless otherwise stated or obvious from the context (unless the number would exceed 100% of a possible value).

[0234] The definitions of specific functional groups and chemical terms are described in more detail below. For the purposes of this invention, chemical elements are identified according to the Periodic Table of the Elements, CAS edition, Handbook of Chemistry and Physics, 75th edition, inner cover, and specific functional groups are generally defined as described herein. Furthermore, general principles of organic chemistry, as well as specific functional groups and reactivity, are described in the following references: Organic Chemistry, Thomas Sorrell, University Science Books, Sausalito, 1999; Smith and March March's Advanced Organic Chemistry, 5th edition, John Wiley & Sons, Inc., New York, 2001; Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989; Carruthers, Some Modern Methods of Organic Synthesis, 3rd edition, Cambridge University Press, Cambridge, 1987; the entire contents of each of these references are incorporated herein by reference.

[0235] Some of the compounds provided herein may include one or more asymmetric centers and therefore may exist in a variety of stereoisomeric forms, such as enantiomers and / or diastereomers. Therefore, the compounds and compositions thereof of the present invention may be in the form of individual enantiomers, diastereomers, or geometric isomers, or may be in the form of mixtures of stereoisomers. In some embodiments, the compounds described herein are enantiomerically pure compounds. In some other embodiments, mixtures of enantiomers or diastereomers are provided.

[0236] Furthermore, unless otherwise indicated, some compounds described herein may have one or more double bonds that can exist as Z or E isomers. Compounds may be provided as single isomers substantially free of other isomers, and alternatively as mixtures of various isomers, such as racemic mixtures of enantiomers.

[0237] As used herein, the term "isomer" includes any and all geometric and stereoisomers. For example, "isomer" includes cis- and trans-isomers, E- and Z-isomers, R- and S-enantiomers, diastereomers, (D)- and (L)-isomers, racemic mixtures thereof, and other mixtures thereof, all of which fall within the scope of this disclosure. For example, in some embodiments, the compound may be provided substantially free of one or more corresponding stereoisomers and may also be referred to as "stereochemically enriched".

[0238] When a particular enantiomer is preferred, in some embodiments it may be provided as substantially free of the opposite enantiomer and may also be referred to as “optically enriched.” As used herein, “optically enriched” means that the compound consists of a significantly larger proportion of one enantiomer. In some embodiments, the compound consists of at least about 90% enantiomers by weight. In some embodiments, the compound consists of at least about 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9% enantiomers by weight. In some embodiments, the compound is provided with an enantiomer excess of at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9%. In some embodiments, the enantiomers may be isolated from the racemic mixture by any method known to those skilled in the art or prepared by asymmetric synthesis, including chiral high-performance liquid chromatography (HPLC) and the formation and crystallization of chiral salts. See, for example, Jacques et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981); Wilen, SH et al., Tetrahedron 33:2725 (1977); Eliel, EL Stereochemistry of Carbon Compounds (McGraw–Hill, NY, 1962); Wilen, SH Tables of Resolving Agents and Optical Resolutions, p. 268 (ELEliel, ed., Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0239] As used herein, the terms “halo” and “halogen” refer to atoms selected from fluorine (fluorinated, -F), chlorine (chlorinated, -Cl), bromine (brominated, -Br), and iodine (iodinated, -I).

[0240] As used herein, the term "aliphatic" or "aliphatic group" means a hydrocarbon moiety that can be straight-chain (i.e., unbranched), branched, or cyclic (including fused, bridged, and spirofused polycyclic rings) and can be fully saturated or may contain one or more unsaturated units but is not aromatic. Unless otherwise stated, an aliphatic group contains 1 to 30 carbon atoms. In some embodiments, the aliphatic group contains 1 to 12 carbon atoms. In some embodiments, the aliphatic group contains 1 to 8 carbon atoms. In some embodiments, the aliphatic group contains 1 to 6 carbon atoms. In some embodiments, the aliphatic group contains 1 to 5 carbon atoms; in some embodiments, the aliphatic group contains 1 to 4 carbon atoms; in still other embodiments, the aliphatic group contains 1 to 3 carbon atoms; and in still other embodiments, the aliphatic group contains 1 to 2 carbon atoms. Suitable aliphatic groups include, but are not limited to, straight-chain or branched alkyl, alkenyl, and alkynyl groups and their hybrids, such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl.

[0241] As used herein, the term "heteroaliphatic" or "heteroaliphatic group" refers to an aliphatic group in which one or more carbon or hydrogen atoms are replaced by heteroatoms (e.g., oxygen, nitrogen, sulfur, phosphorus, boron, etc.). In some embodiments, the heteroaliphatic group is a heterocyclic group.

[0242] As used in this article, the term "unsaturated" means that a portion of the material has one or more double or triple bonds.

[0243] As used herein, the term "alkyl" refers to a saturated straight-chain or branched hydrocarbon group derived by removing a single hydrogen atom from an aliphatic portion containing one to six carbon atoms. Unless otherwise stated, an alkyl group contains 1 to 12 carbon atoms. In some embodiments, the alkyl group contains 1 to 8 carbon atoms. In some embodiments, the alkyl group contains 1 to 6 carbon atoms. In some embodiments, the alkyl group contains 1 to 5 carbon atoms; in some embodiments, the alkyl group contains 1 to 4 carbon atoms; in still other embodiments, the alkyl group contains 1 to 3 carbon atoms; and in still other embodiments, the alkyl group contains 1 to 2 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, sec-pentyl, isopentyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, n-decyl, n-undecyl, dodecyl, etc.

[0244] As used herein, the term "alkenyl" refers to a monovalent group derived by removing a single hydrogen atom from a straight-chain or branched aliphatic moiety having at least one carbon-carbon double bond. Unless otherwise stated, an alkenyl group contains 2 to 12 carbon atoms. In some embodiments, the alkenyl group contains 2 to 8 carbon atoms. In some embodiments, the alkenyl group contains 2 to 6 carbon atoms. In some embodiments, the alkenyl group contains 2 to 5 carbon atoms; in some embodiments, the alkenyl group contains 2 to 4 carbon atoms; in still other embodiments, the alkenyl group contains 2 to 3 carbon atoms; and in still other embodiments, the alkenyl group contains 2 carbon atoms. Alkenyl groups include, for example, vinyl, propenyl, butenyl, 1-methyl-2-buten-1-yl, etc.

[0245] The term "aryl," used alone or as part of a larger part, such as in "aralkyl," "arylalkoxy," or "aryloxyalkyl," refers to a monocyclic or polycyclic system having a total of five to 20 ring members, wherein at least one ring in the system is aromatic and wherein each ring in the system contains three to twelve ring members. The term "aryl" may be used interchangeably with the term "aryl ring." In some embodiments, "aryl" refers to an aromatic ring system including, but not limited to, phenyl, biphenyl, naphthyl, anthracene, etc., which may have one or more substituents. As used herein, the term "aryl" also includes groups within its scope where the aromatic ring is fused to one or more additional rings, such as benzofuranyl, indanyl, phthalimide, naphthimide, phenanthridine, or tetrahydronaphthyl.

[0246] The terms "heteroaryl" and "heteroary-" used alone or as part of a larger portion, such as "heteroarylalkyl" or "heteroarylalkoxy," refer to groups having 5 to 10 ring atoms, preferably 5, 6, or 9 ring atoms; sharing 6, 10, or 14 π electrons in a cyclic array; and having one to five heteroatoms in addition to carbon atoms. The term "heteroatom" refers to nitrogen, oxygen, or sulfur, and includes any oxidized form of nitrogen or sulfur, as well as any quaternized form of basic nitrogen. Heteroaryl groups include, but are not limited to, thienyl, furanyl, pyrroleyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, indoleazinyl, purine, naphridinyl, and pteridinyl. As used herein, the terms “heteroaryl” and “heteroary-” also include groups fused to one or more aryl, alicyclic, or heterocyclic rings of a heteroaromatic ring, wherein the group or attachment site is located on the heteroaromatic ring. Non-limiting examples include indolyl, isoindolyl, benzothiopheneyl, benzofuranyl, dibenzofuranyl, indazoleyl, benzimidazolyl, phenthiazolyl, quinolinyl, isoquinolinyl, cenolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 4H-quinazinyl, carbazolyl, acridineyl, phenazinyl, phenothiazinyl, phenotoxazinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, and pyrido[2,3–b]–1,4–oxazin–3(4H)–one. Heteroaryl groups can be monocyclic, bicyclic, bridged bicyclic, or spirocyclic. The term "heteroaryl" may be used interchangeably with the terms "heteroaryl ring," "heteroaryl group," or "heteroaromatic," any of which includes an optionally substituted ring. The term "heteroarylalkyl" refers to an alkyl group substituted with a heteroaryl group, wherein the alkyl and heteroaryl portions are independently optionally substituted. The term "heteroarylenyl" refers to a divalent heteroaryl group (e.g., pyridinylenyl).

[0247] As used herein, the terms “heterocycle,” “heterocyclic group,” “heterocyclic group,” and “heterocyclic ring” are used interchangeably and refer to a stable 5- to 7-membered monocyclic or 7- to 10-membered bicyclic heterocyclic portion that is saturated or partially unsaturated and has one or more, preferably one to four, heteroatoms as defined above, in addition to a carbon atom. When used with respect to the ring atom of the heterocycle, the term “nitrogen” includes substituted nitrogen. As an example, in a saturated or partially unsaturated ring having 0 to 3 heteroatoms selected from oxygen, sulfur, or nitrogen, nitrogen can be N (as in 3,4-dihydro-2H-pyrrole), NH (as in pyrrolidinyl), or +NR (as in N-substituted pyrrolidinyl).

[0248] Heterocycles can have their side groups attached to any heteroatom or carbon atom to produce a stable structure, and any ring atom can optionally be substituted. Examples of such saturated or partially unsaturated heterocyclic groups include, but are not limited to, tetrahydrofuranyl, tetrahydrothiophenyl, pyrrolyl, piperidinyl, pyrrololinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl, oxazolidinyl, piperazine, dioxalyl, dioxopentyl, diazazyl, oxonitrile, thioazazyl, morpholinyl, and quininecycloyl. The terms “heterocycle,” “heterocyclic group,” “heterocyclic ring,” “heterocyclic moiety,” and “heterocyclic group” are used interchangeably herein and also include groups fused with one or more aryl, heteroaryl, or alicyclic rings, such as dihydroindolyl, 3H-indolyl, benzodihydropyranyl, phenanthridine, or tetrahydroquinolinyl. In some embodiments, the heterocycle may be a 5-12 membered bicyclic, bridged bicyclic, or spirocyclic. The heterocycle may contain one or more oxo (=O) or thio (=S) substituents. The term "heterocyclic alkyl" refers to an alkyl group substituted with a heterocyclic group, wherein the alkyl and heterocyclic portions are optionally substituted independently.

[0249] As used herein, the term "partially unsaturated" refers to a ring moiety containing at least one double or triple bond. The term "partially unsaturated" is intended to cover rings having multiple unsaturated sites, but not to include aryl or heteroaryl moiety as defined herein.

[0250] As described herein, compounds provided herein may contain an "optionally substituted" moiety. Generally, the term "substituted," whether or not preceded by the term "optionally," means that one or more hydrogen atoms of the specified moiety are replaced by suitable substituents. Unless otherwise indicated, the "optionally substituted" group may have suitable substituents at each substituted position of the group, and the substituents at each position may be the same or different when more than one position in any given structure is substituted by more than one substituent selected from the specified group. The contemplated combinations of substituents are preferably those that result in the formation of stable or chemically viable compounds. The term "stable" as used herein means that the compound remains substantially unchanged when subjected to conditions that allow it to be generated, detected, and, in some embodiments, recovered, purified, and used for one or more purposes disclosed herein.

[0251] The suitable monovalent substituent on the substituted carbon atom of the "optionally substituted" group is independently a halogen; –(CH2) 0–4 R°;–(CH2) 0–4 OR°;-O-(CH2) 0-4 C(O)OR°;–(CH2) 0–4 CH(OR°)2;–(CH2) 0–4 SR°;–(CH2)0– 4Ph, which can be replaced by R°; –(CH2) 0–4 O(CH2) 0–1 Ph, which can be substituted by R°; –CH=CHPh, which can be substituted by R°; –NO2; –CN; –N3; –(CH2) 0–4 N(R°)2;–(CH2) 0–4 N(R°)C(O)R°; –N(R°)C(S)R°; –(CH2) 0-4 N(R°)C(O)NR°2; –N(R°)C(S)NR°2; –(CH2) 0–4 N(R°)C(O)OR°; -N(R°)N(R°)C(O)R°; –N(R°)N(R°)C(O)NR°2; –N(R°)N(R°)C(O)OR°; –(CH2) 0–4 C(O)R°;-C(S)R°;–(CH2) 0–4 C(O)OR°;–(CH2) 0–4 C(O)N(R°)2;–(CH2) 0–4 C(O)SR°;–(CH2) 0–4 C(O)OSiR°3;–(CH2) 0–4 OC(O)R°;–OC(O)(CH2) 0–4 SR–, SC(S)SR°; –(CH2) 0–4 SC(O)R°;–(CH2) 0–4 C(O)NR°2; -C(S)NR°2; –C(S)SR°; –SC(S)SR°, –(CH2) 0–4 OC(O)NR°2; –C(O)N(OR°)R°; –C(O)C(O)R°; –C(O)CH2C(O)R°; –C(NOR°)R°; –(CH2) 0–4 SSR°;–(CH2) 0– 4S(O)2R°;–(CH2) 0–4 S(O)₂OR°;-(CH₂) 0–4 OS(O)2R°; –S(O)2NR°2; –(CH2) 0–4 S(O)R°; –N(R°)S(O)2NR°2; –N(R°)S(O)2R°; –N(OR°)R°; –C(NH)NR°2; –P(O)2R°; –P(O)R°2; –OP(O)R°2; –OP(O)(OR°)2; SiR°3; –(C 1–4 (linear or branched alkylene)O–N(R°)2; or –(C 1–4(straight-chain or branched alkylene)C(O)O–N(R°)2, wherein each R° can be substituted as defined below and is independently hydrogen, C 1-8 Aliphatic, –CH2Ph, –O(CH2) 0–1 Ph or a 5-6 saturated, partially unsaturated or aryl ring having 0-4 independent heteroatoms selected from nitrogen, oxygen or sulfur; or, in addition to the above definitions, two independently occurring R° together with their intermediate atom to form a 3-12 saturated, partially saturated or aryl monocyclic or polycyclic ring having 0-4 independent heteroatoms selected from nitrogen, oxygen or sulfur, which may be substituted as defined below.

[0252] A suitable monovalent substituent of R°, together with its intermediate atom, is independently a halogen, –(CH2). 0–2 R ● –(halogenated R) ● ), –(CH2) 0–2 OH, –(CH2) 0–2 OR ● –(CH2) 0–2 CH(OR ● )2;-O(halogenated R ● –CN, –N3, –(CH2) 0–2 C(O)R ● –(CH2) 0–2 C(O)OH, –(CH2) 0–2 C(O)OR ● -(CH2) 0-4 C(O)N(R°)2;–(CH2) 0–2 SR ● –(CH2) 0–2 SH, –(CH2) 0–2 NH2、–(CH2) 0–2 NHR ● -(CH2) 0-2 NR ● 2. –NO2, –SiR ● 3. –OSiR ● 3. –C(O)SR ● 、 –(C 1–4 (straight-chain or branched alkylene)C(O)OR ● Or –SSR ● , where each R ● It is either unsubstituted or, in the case of the prefix "halogenated", substituted with only one or more halogens, and independently selected from C. 1–4 Aliphatic, -CH2Ph, –O(CH2) 0–1Ph or a 5-6 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents on the saturated carbon atom of R° include =O and =S.

[0253] Suitable divalent substituents on the saturated carbon atom of the "optionally substituted" group include the following: =O, =S, =NNR * 2、=NNHC(O)R * =NNHC(O)OR * =NNHS(O)2R * =NR * =NOR * 、 –O(C(R) * 2)) 2–3 O – or –S(C(R) * 2)) 2– 3S–, where each independently occurring R * Selected from hydrogen, and C that can be substituted as defined below. 1–6 Aliphatic, or an unsubstituted 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 independent heteroatoms selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents bonded to the ortho-substituted carbon of the "optionally substituted" group include: –O(CR * 2) 2–3 O–, where each independently occurring R * Selected from hydrogen, and C that can be substituted as defined below. 1–6 Aliphatic, or having 0-4 unsubstituted 5-6 saturated, partially unsaturated or aryl rings independently selected from nitrogen, oxygen or sulfur.

[0254] R * Suitable substituents on aliphatic groups include halogens, -R ● -(halogenated R) ● –OH, –OR ● –O (halogenated R) ● ), –CN, –C(O)OH, –C(O)OR ● –NH2, –NHR ● –NR ● 2 or –NO2, where each R ● It is either unsubstituted or, in the case of the prefix "halogenated", substituted with only one or more halogens, and is independently C. 1–4 Aliphatic, –CH2Ph, –O(CH2) 0–1 Ph or a 5-6 member saturated, partially unsaturated or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur.

[0255] Suitable substituents on the substituted nitrogen of the "optionally substituted" group include –R † –NR † 2. –C(O)R † –C(O)OR † –C(O)C(O)R † –C(O)CH2C(O)R † –S(O)2R † -S(O)2NR † 2. –C(S)NR † 2. –C(NH)NR † 2 or –N(R) † )S(O)2R † ; where each R † Independently, hydrogen can be substituted C as defined below. 1-6 Aliphatic, unsubstituted -OPh, or an unsubstituted 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 independently selected heteroatoms chosen from nitrogen, oxygen, or sulfur; or, in addition to the above definitions, two independently occurring R... † Together with its intermediate atom, it forms an unsubstituted 3-12 saturated, partially unsaturated, or aryl monocyclic or bicyclic ring with 0-4 independent heteroatoms selected from nitrogen, oxygen, or sulfur.

[0256] R † Suitable substituents on the aliphatic group can be halogens, -R ● –(halogen R) ● –OH, –OR ● –O (halogen R) ● ), –CN, –C(O)OH, –C(O)OR ● –NH2, –NHR ● –NR ● 2 or -NO2, where each R ● It is either unsubstituted or, in the case of the prefix "halogenated", substituted with only one or more halogens, and is independently C. 1–4 Aliphatic, –CH2Ph, –O(CH2) 0–1 Ph or a 5-6-membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0257] As used in this article, the term “substantially” refers to a qualitative condition that exhibits all or nearly all of the scope or degree of the intended characteristics or properties.

[0258] Sometimes, a convention is used to name ascarosides with a few letters prefixed by a hash symbol (#) and a number (e.g., ascr#18). This convention is used in scientific literature, and those skilled in the art will understand that each such name relates to a specific chemical structure of known composition and will readily understand the structure of the molecule referred to using this naming convention. Unless otherwise indicated, all compound identifiers in this format used herein conform to the definitions described in the Small Molecule Identifiers Database for Caenorhabditis elegans (SMID-DB) maintained on the World Wide Web smid-db.org.

[0259] The embodiments of the present invention include:

[0260] 1. An ascaroside composition comprising one or more ascarosides and a soluble solid carrier composition, wherein the ascaroside composition comprises 20% by weight or less of the one or more ascarosides.

[0261] 2. The composition according to embodiment 1, wherein the ascaroside composition comprises 1% to 20% by weight of one or more of the ascaroside.

[0262] 3. The composition according to embodiment 1 or 2, wherein the one or more ascarosides comprises ascaroside having structure (I):

[0263]

[0264] in:

[0265] Z represents C, which is arbitrarily substituted. 3-40 Aliphatic groups, and

[0266] R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., part-C(O)OR) c C 2-20 Carbamates (e.g., -partial-C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C1-20 Thiocarbamates (e.g., partially -C(S)N(R) c )2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker, wherein R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, wherein R a and R b They can together form optionally substituted rings, which optionally contain one or more heteroatoms and optionally one or more unsaturated sites.

[0267] 4. The composition according to embodiment 3, wherein Z is selected from the group consisting of:

[0268] i.–CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic groups

[0269] ii.–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0270] iii.–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0271] iv.–CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0272] v.–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0273] vi. –(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0274] vii.–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0275] viii.–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; and

[0276] ix.–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0277] 5. The composition according to embodiment 3, wherein Z is selected from the group consisting of:

[0278] (x)–CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0279] (xi)–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0280] (xii)–CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0281] (xiii)–CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0282] (xiv)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0283] (xv)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0284] (xvi)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkages to another ascaridone molecule via bonds or carbon-containing linker portions; or

[0285] (xvii)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or carbon-containing linker.

[0286] 6. The composition according to any one of embodiments 3 to 5, wherein R a and R b Each is -H.

[0287] 7. The composition according to any one of embodiments 3 to 6, wherein Z is –CH(CH3)–(CH2). n –CO2R 2 , where n is an integer from 1 to 40, and R 2-H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0288] 8. The composition according to any one of embodiments 1 to 7, wherein the at least one ascaroside comprises ascaroside selected from the group consisting of: ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22 and ascr#24.

[0289] 9. The composition according to any one of embodiments 1 to 8, wherein the at least one ascaroside comprises ascr#18.

[0290] 10. The composition according to any one of embodiments 1 to 9, wherein at least one ascaroside is an ascaroside salt.

[0291] 11. The composition according to any one of embodiments 1 to 10, wherein the carrier composition comprises a water-soluble filler.

[0292] 12. The composition according to embodiment 11, wherein the water-soluble filler is a carbohydrate.

[0293] 13. The composition according to embodiment 12, wherein the carbohydrate water-soluble filler is selected from the group consisting of: lactose, glucose, fructose, mannose, mannitol, sucrose, powdered sugar, black sugar, brown sugar, soft brown sugar, microcrystalline cellulose, starch, and powdered cellulose.

[0294] 14. The composition according to embodiment 11, wherein the water-soluble filler is a neutral inorganic salt.

[0295] 15. The composition according to embodiment 14, wherein the inorganic salt is calcium nitrate, calcium chloride, copper phosphate (II), copper chloride (I), copper carbonate (II), copper iodide (I), ferric molybdate (II), potassium sulfate, potassium bromide, potassium chloride, potassium nitrate, magnesium nitrate, magnesium chloride, magnesium sulfate, sodium sulfate, sodium chloride, sodium nitrite, and sodium nitrate.

[0296] 16. The composition according to embodiment 11, wherein the water-soluble filler is polyethylene glycol.

[0297] 17. The composition according to embodiment 16, wherein the polyethylene glycol has an average molecular weight between 3,000 and 8,000.

[0298] 18. The composition according to embodiments 1 to 17, wherein the particulate carrier composition comprises one or more pH adjusters.

[0299] 19. The composition according to embodiment 18, wherein the pH adjuster lowers the pH of the aqueous solution when dissolved in water.

[0300] 20. The composition according to embodiment 19, wherein the pH adjuster is selected from the group consisting of: ammonium sulfate, calcium dihydrogen phosphate, copper nitrate (II), copper bromide (II), copper chloride (II), copper sulfate (II), boric acid, potassium dihydrogen phosphate, sodium sulfite, sodium dihydrogen phosphate, sodium bisulfite, sodium bisulfite, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium bisulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide.

[0301] 21. The composition according to embodiment 18, wherein the pH adjuster increases the pH of the aqueous solution when dissolved in water.

[0302] 22. The composition according to embodiment 21, wherein the pH adjuster is selected from the group consisting of: ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium bicarbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium bicarbonate, potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium bicarbonate, sodium hydroxide, ammonium bicarbonate, zinc hydroxide, and zinc carbonate.

[0303] 23. The composition according to any one of embodiments 1 to 22, wherein the ascaroside granule composition comprises one or more ascarosides and one or more carbonates.

[0304] 24. The composition according to any one of embodiments 1 to 22, wherein the particulate carrier composition comprises one or more water-soluble fillers and one or more pH adjusters.

[0305] 25. The composition according to embodiment 1, wherein the particulate composition is substantially composed of one or more ascaroside and one or more carbonates.

[0306] 26. A method for treating crops or plants with one or more ascarosides, the method comprising:

[0307] A soluble solid ascaroside composition is obtained, comprising one or more ascarosides and a soluble solid carrier composition, wherein the ascaroside composition comprises 20% by weight or less of the one or more ascarosides.

[0308] The ascaroside composition is mixed with water to form an ascaroside solution; and

[0309] The ascaroside solution is applied to the crop or plant.

[0310] 27. The method according to embodiment 26, wherein the particulate composition is mixed with about 2 L to about 10 L of water.

[0311] 28. The method according to embodiment 26 or 27, wherein the particulate composition is placed in a container before being mixed with the water.

[0312] 29. The method according to any one of embodiments 26 to 28, wherein after mixing, the concentration of the one or more ascarosides in the water is about 0.5 mM to about 2 mM.

[0313] 30. The method according to any one of embodiments 26 to 29, wherein the ascaroside granule composition is mixed with water to form a concentrated solution, and wherein the method further comprises diluting the concentrated solution with water to form a diluted solution.

[0314] 31. The method according to embodiment 30, wherein the diluted solution is applied to the crop or plant.

[0315] 32. The method according to any one of embodiments 26 to 31, wherein the ascaroside composition comprises 1% to 20% by weight of one or more of the ascaroside.

[0316] 33. The method according to any one of embodiments 26 to 32, wherein the one or more ascarosides comprises an ascaroside having structure (I):

[0317]

[0318] in:

[0319] Z represents C, which is arbitrarily substituted. 3-40 Aliphatic groups, and

[0320] R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., part-C(O)OR) c C 2-20 Carbamates (e.g., -partial-C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c )2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker, wherein R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, wherein R a and R b They can together form optionally substituted rings, which optionally contain one or more heteroatoms and optionally one or more unsaturated sites.

[0321] 34. The method according to implementation scheme 33, wherein Z is selected from the group consisting of:

[0322] x.–CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic groups

[0323] xi.–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0324] xii.–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0325] xiii.–CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2-H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0326] xiv.–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0327] xv.–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0328] xvi.–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0329] xvii.–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; and

[0330] xviii.–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0331] 35. The composition according to embodiment 32, wherein Z is selected from the group consisting of:

[0332] (x)–CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0333] (xi)–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0334] (xii)–CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0335] (xiii)–CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0336] (xiv)–(CH2) n –CON(R3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0337] (xv)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0338] (xvi)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkages to another ascaridone molecule via bonds or carbon-containing linker portions; or

[0339] (xvii)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or carbon-containing linker.

[0340] 36. The method according to any one of embodiments 33 to 35, wherein R a and R b Each is -H.

[0341] 37. The method according to any one of embodiments 33 to 36, wherein Z is –CH(CH3)–(CH2). n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0342] 38. The method according to any one of embodiments 26 to 37, wherein the at least one ascaroside comprises ascaroside selected from the group consisting of: ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22 and ascr#24.

[0343] 39. The method according to any one of embodiments 26 to 38, wherein the at least one ascaroside comprises ascr#18.

[0344] 40. The method according to any one of embodiments 26 to 39, wherein at least one ascaroside is an ascaroside salt.

[0345] 41. The method according to any one of embodiments 26 to 40, wherein the particulate carrier composition comprises a water-soluble filler.

[0346] 42. The method according to embodiment 41, wherein the water-soluble filler is a carbohydrate.

[0347] 43. The method according to embodiment 42, wherein the carbohydrate water-soluble filler is selected from the group consisting of: lactose, glucose, fructose, mannose, mannitol, sucrose, powdered sugar, black sugar, brown sugar, soft brown sugar, microcrystalline cellulose, starch, and powdered cellulose.

[0348] 44. The method according to embodiment 41, wherein the water-soluble filler is a neutral inorganic salt.

[0349] 45. The method according to embodiment 44, wherein the inorganic salt is calcium nitrate, calcium chloride, copper phosphate (II), copper chloride (I), copper carbonate (II), copper iodide (I), ferric molybdate (II), potassium sulfate, potassium bromide, potassium chloride, potassium nitrate, magnesium nitrate, magnesium chloride, magnesium sulfate, sodium sulfate, sodium chloride, sodium nitrite, and sodium nitrate.

[0350] 46. ​​The method according to embodiment 41, wherein the water-soluble filler is polyethylene glycol.

[0351] 47. The method according to embodiment 46, wherein the polyethylene glycol has an average molecular weight between 3,000 and 8,000.

[0352] 48. The method according to embodiments 26 to 47, wherein the particulate carrier composition comprises one or more pH adjusters.

[0353] 49. The method according to embodiment 48, wherein the pH adjuster lowers the pH of the aqueous solution when dissolved in water.

[0354] 50. The method according to embodiment 49, wherein the pH adjuster is selected from the group consisting of: ammonium sulfate, calcium dihydrogen phosphate, copper nitrate (II), copper bromide (II), copper chloride (II), copper sulfate (II), boric acid, potassium dihydrogen phosphate, sodium sulfite, sodium dihydrogen phosphate, sodium bisulfite, sodium bisulfite, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium bisulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide.

[0355] 51. The method according to embodiment 48, wherein the pH adjuster increases the pH of the aqueous solution when dissolved in water.

[0356] 52. The method according to embodiment 51, wherein the pH adjuster is selected from the group consisting of: ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium bicarbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium bicarbonate, potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), trisodium phosphate, sodium bicarbonate, sodium hydroxide, ammonium bicarbonate, zinc hydroxide, and zinc carbonate.

[0357] 53. The method according to any one of embodiments 26 to 52, wherein the ascaroside granule composition comprises one or more ascarosides and one or more carbonates.

[0358] 54. The method according to any one of embodiments 26 to 53, wherein the particulate carrier composition comprises one or more water-soluble fillers and one or more pH adjusters.

[0359] 55. The method according to embodiment 26, wherein the particulate composition is substantially composed of one or more ascaroside and one or more carbonates.

[0360] 56. An ascaroside composition comprising one or more ascarosides and a solid soluble carrier composition, wherein the ascaroside composition comprises 0.2% by weight or less of the one or more ascarosides.

[0361] 57. The composition according to embodiment 56, wherein the ascaroside composition comprises 0.005% to 0.2% by weight of one or more of the ascaroside.

[0362] 58. The composition according to claim 56 or 57, wherein the one or more ascarosides comprises ascaroside having structure (I):

[0363]

[0364] in:

[0365] Z represents C, which is arbitrarily substituted. 3-40 Aliphatic groups, and

[0366] R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., part-C(O)OR) c C 2-20 Carbamates (e.g., -partial-C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c )2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker, wherein R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, wherein R a and R b They can together form optionally substituted rings, which optionally contain one or more heteroatoms and optionally one or more unsaturated sites.

[0367] 59. The composition according to embodiment 58, wherein Z is selected from the group consisting of:

[0368] xix.–CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic groups

[0369] xx.–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0370] xxi.–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0371] xxii.–CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0372] xxiii.–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0373] xxiv.–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0374] xxv.–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0375] xxvi.–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; and

[0376] xxvii.–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0377] 60. The composition according to embodiment 58, wherein Z is selected from the group consisting of:

[0378] (x)–CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0379] (xi)–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0380] (xii)–CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0381] (xiii)–CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0382] (xiv)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0383] (xv)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0384] (xvi)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkages to another ascaridone molecule via bonds or carbon-containing linker portions; or

[0385] (xvii)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or carbon-containing linker.

[0386] 61. The composition according to any one of embodiments 58 to 60, wherein R a and R b Each is -H.

[0387] 62. The composition according to any one of embodiments 58 to 61, wherein Z is –CH(CH3)–(CH2). n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0388] 63. The composition according to any one of embodiments 56 to 62, wherein the at least one ascaroside comprises ascaroside selected from the group consisting of: ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22 and ascr#24.

[0389] 64. The composition according to any one of embodiments 56 to 63, wherein the at least one ascaroside comprises ascr#18.

[0390] 65. The composition according to any one of embodiments 56 to 64, wherein at least one ascaroside is an ascaroside salt.

[0391] 66. The composition according to any one of embodiments 56 to 65, wherein the particulate carrier composition comprises a water-soluble filler.

[0392] 67. The composition according to embodiment 66, wherein the water-soluble filler is a carbohydrate.

[0393] 68. The composition according to embodiment 67, wherein the carbohydrate water-soluble filler is selected from the group consisting of: lactose, glucose, fructose, mannose, mannitol, sucrose, powdered sugar, black sugar, brown sugar, soft brown sugar, microcrystalline cellulose, starch, and powdered cellulose.

[0394] 69. The composition according to embodiment 66, wherein the water-soluble filler is a neutral inorganic salt.

[0395] 70. The composition according to embodiment 69, wherein the inorganic salt is calcium nitrate, calcium chloride, copper phosphate (II), copper chloride (I), copper carbonate (II), copper iodide (I), ferric molybdate (II), potassium sulfate, potassium bromide, potassium chloride, potassium nitrate, magnesium nitrate, magnesium chloride, magnesium sulfate, sodium sulfate, sodium chloride, sodium nitrite, and sodium nitrate.

[0396] 71. The composition according to embodiment 66, wherein the water-soluble filler is polyethylene glycol.

[0397] 72. The composition according to embodiment 71, wherein the polyethylene glycol has an average molecular weight between 3,000 and 8,000.

[0398] 73. The composition according to embodiments 56 to 72, wherein the particulate carrier composition comprises one or more pH adjusters.

[0399] 74. The composition according to embodiment 73, wherein the pH adjuster lowers the pH of the aqueous solution when dissolved in water.

[0400] 75. The composition according to embodiment 74, wherein the pH adjuster is selected from the group consisting of: ammonium sulfate, calcium dihydrogen phosphate, copper nitrate (II), copper bromide (II), copper chloride (II), copper sulfate (II), boric acid, potassium dihydrogen phosphate, sodium sulfite, sodium dihydrogen phosphate, sodium bisulfite, sodium bisulfite, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium bisulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide.

[0401] 76. The composition according to embodiment 73, wherein the pH adjuster increases the pH of the aqueous solution when dissolved in water.

[0402] 77. The composition according to embodiment 76, wherein the pH adjuster is selected from the group consisting of: ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium bicarbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium bicarbonate, potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium bicarbonate, sodium hydroxide, ammonium bicarbonate, zinc hydroxide, and zinc carbonate.

[0403] 78. The composition according to any one of embodiments 56 to 77, wherein the ascaroside granule composition comprises one or more ascarosides and one or more carbonates.

[0404] 79. The composition according to any one of embodiments 56 to 78, wherein the particulate carrier composition comprises one or more water-soluble fillers and one or more pH adjusters.

[0405] 80. The composition according to embodiment 56, wherein the particulate composition is substantially composed of one or more ascaroside and one or more carbonates.

[0406] 81. A method for treating crops or plants with one or more ascarosides, the method comprising:

[0407] A soluble solid ascaroside composition is obtained, comprising one or more ascarosides and a soluble solid carrier composition, wherein the ascaroside composition comprises 0.2% by weight or less of the one or more ascarosides.

[0408] The ascaroside granule composition is mixed with water to form an ascaroside solution; and

[0409] The ascaroside solution is applied to the crop or plant.

[0410] 82. The method according to embodiment 81, wherein the particulate composition is mixed with about 2 L to about 10 L of water.

[0411] 83. The method according to embodiment 81 or 82, wherein the particulate composition is placed in a container before being mixed with the water.

[0412] 84. The method according to any one of embodiments 81 to 83, wherein the ascaroside composition comprises 0.005% to 0.2% by weight of one or more of the ascaroside.

[0413] 85. The method according to any one of embodiments 81 to 84, wherein the one or more ascarosides comprises an ascaroside having structure (I):

[0414]

[0415] in:

[0416] Z represents C, which is arbitrarily substituted. 3-40 Aliphatic groups, and

[0417] R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., part-C(O)OR) c C 2-20 Carbamates (e.g., -partial-C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c )2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker, wherein R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, wherein R a and Rb They can together form optionally substituted rings, which optionally contain one or more heteroatoms and optionally one or more unsaturated sites.

[0418] 86. The method according to implementation scheme 85, wherein Z is selected from the group consisting of:

[0419] xxviii.–CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic groups

[0420] xxix.–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0421] xxx.–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0422] xxxi.–CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0423] xxxii.–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0424] xxxiii.–(CH2) n –CO2R 2, where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0425] xxxiv.–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides;

[0426] xxxv.–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; and

[0427] xxxi.–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0428] 87. The method according to implementation scheme 85, wherein Z is selected from the group consisting of:

[0429] (x)–CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0430] (xi)–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0431] (xii)–CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0432] (xiii)–CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0433] (xiv)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0434] (xv)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker.

[0435] (xvi)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkages to another ascaridone molecule via bonds or carbon-containing linker portions; or

[0436] (xvii)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or carbon-containing linker.

[0437] 88. The method according to any one of embodiments 85 to 87, wherein R a and R b Each is -H.

[0438] 89. The method according to any one of embodiments 85 to 88, wherein Z is –CH(CH3)–(CH2). n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0439] 90. The method according to any one of embodiments 81 to 89, wherein the at least one ascaroside comprises ascaroside selected from the group consisting of: ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22 and ascr#24.

[0440] 91. The method according to any one of embodiments 81 to 90, wherein the at least one ascaroside comprises ascr#18.

[0441] 92. The method according to any one of embodiments 81 to 91, wherein at least one ascaroside is an ascaroside salt.

[0442] 93. The method according to any one of embodiments 81 to 92, wherein the particulate carrier composition comprises a water-soluble filler.

[0443] 94. The method according to embodiment 93, wherein the water-soluble filler is a carbohydrate.

[0444] 95. The method according to embodiment 94, wherein the carbohydrate water-soluble filler is selected from the group consisting of: lactose, glucose, fructose, mannose, mannitol, sucrose, powdered sugar, black sugar, brown sugar, soft brown sugar, microcrystalline cellulose, starch, and powdered cellulose.

[0445] 96. The method according to embodiment 93, wherein the water-soluble filler is a neutral inorganic salt.

[0446] 97. The method according to embodiment 96, wherein the inorganic salt is calcium nitrate, calcium chloride, copper phosphate (II), copper chloride (I), copper carbonate (II), copper iodide (I), ferric molybdate (II), potassium sulfate, potassium bromide, potassium chloride, potassium nitrate, magnesium nitrate, magnesium chloride, magnesium sulfate, sodium sulfate, sodium chloride, sodium nitrite, and sodium nitrate.

[0447] 98. The method according to embodiment 93, wherein the water-soluble filler is polyethylene glycol.

[0448] 99. The method according to embodiment 98, wherein the polyethylene glycol has an average molecular weight between 3,000 and 8,000.

[0449] 100. The method according to embodiments 81 to 99, wherein the particulate carrier composition comprises one or more pH adjusters.

[0450] 101. The method according to embodiment 100, wherein the pH adjuster lowers the pH of the aqueous solution when dissolved in water.

[0451] 102. The method according to embodiment 101, wherein the pH adjuster is selected from the group consisting of: ammonium sulfate, calcium dihydrogen phosphate, copper nitrate (II), copper bromide (II), copper chloride (II), copper sulfate (II), boric acid, potassium dihydrogen phosphate, sodium sulfite, sodium dihydrogen phosphate, sodium bisulfite, sodium bisulfite, ammonium bromide, ammonium chloride, ammonium dihydrogen phosphate, ammonium bisulfate, ammonium iodide, ammonium nitrate, zinc nitrate, zinc bromide, zinc chloride, and zinc iodide.

[0452] 103. The method according to embodiment 100, wherein the pH adjuster increases the pH of the aqueous solution when dissolved in water.

[0453] 104. The method according to embodiment 103, wherein the pH adjuster is selected from the group consisting of: ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium bicarbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, potassium aluminum sulfate, potassium bicarbonate, potassium nitrite, potassium hydroxide, lithium hydroxide, lithium carbonate, lithium bicarbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium bicarbonate, sodium hydroxide, ammonium bicarbonate, zinc hydroxide, and zinc carbonate.

[0454] 105. The method according to any one of embodiments 81 to 104, wherein the ascaroside granule composition comprises one or more ascarosides and one or more carbonates.

[0455] 106. The method according to any one of embodiments 81 to 105, wherein the particulate carrier composition comprises one or more water-soluble fillers and one or more pH adjusters.

[0456] 107. The method according to embodiment 81, wherein the particulate composition is substantially composed of one or more ascaroside and one or more carbonates.

[0457] The compounds, compositions, and methods of this application are intended to cover variations and adaptations developed using information from the embodiments described in this disclosure. Those skilled in the art can adjust or modify the methods and processes described in this specification.

[0458] It will be understood that the use of headings in this disclosure is for the convenience of the reader. The presence and / or placement of headings are not intended to limit the scope of the subject matter described herein. Unless otherwise stated, embodiments located in one part of this application are applicable individually or in combination to other embodiments throughout the application.

[0459] Throughout this specification, where a composition, compound, or product is described as having, including, or containing specific components, or where a process or method is described as having, including, or containing specific steps, it is contemplated that the articles, apparatus, and systems of this application are also substantially composed of, or consist of, the said components, and that the processes and methods according to this application are also substantially composed of, or consist of, the said process steps.

[0460] It should be understood that the order of steps or the order in which an action is performed is irrelevant as long as the method remains operational. Furthermore, two or more steps or actions can be performed simultaneously.

[0461] All publications and patent applications mentioned in this specification are intended to be of the skill of a person skilled in the art to which this invention pertains. All publications and patent applications are incorporated herein by reference as if each individual publication or patent application were specifically and individually indicated to be incorporated by reference.

[0462] Although the invention has been described in detail by way of illustration and examples for clarity, it will be apparent that certain changes and modifications may be made within the scope of the appended claims.

Claims

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

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

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

4. The composition according to claim 3, wherein Z is selected from the group consisting of: i.–CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic groups ii.–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; iii.–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; iv.–CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; v.–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; vi. –(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; vii.–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; viii.–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; and ix.–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

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

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

7. The composition according to any one of claims 1 to 6, wherein the one or more ascarosides include ascr#18.

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

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

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

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

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

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

14. The composition according to any one of claims 1 to 13, wherein the ascaroside composition is substantially composed of one or more ascarosides and one or more carbonates (e.g., sodium bicarbonate or potassium bicarbonate).

15. The composition according to any one of claims 1 to 14, wherein the composition is characterized in that the one or more ascarosides exhibit a water solubility of at least 1, 3, 6, 9, 12, 15, 20 or 25 g / gal.

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

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

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

19. A method for treating crops or plants with one or more ascarosides, the method comprising: To obtain the ascaroside composition according to any one of claims 1 to 18, The ascaroside composition is mixed with water to form an ascaroside solution; as well as The ascaroside solution is applied to the crop or plant.

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

22. The method according to any one of claims 19 to 21, wherein the ascaroside composition is mixed with water to form 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 crop or plant.

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

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

26. The composition according to claim 24 or 25, wherein the one or more ascarosides comprises ascaroside having structure (I): in: Z represents C, which is arbitrarily substituted. 3-40 Aliphatic groups, and R a and R b Each of them is independently -H or an optionally substituted portion of a group consisting of the following: C 1-20 aliphatic, C 1-20 Acyl group, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-linked functional groups, sulfur-linked functional groups, silicon-linked functional groups, C 2-20 Carbonates (e.g., part-C(O)OR) c C 2-20 Carbamates (e.g., -partial-C(O)N(R) c )2) C 2-20 Thioesters (e.g., partially -C(S)R) c C 2-20 Thiocarbonates (e.g., partially -C(S)OR) c C 2-20 Dithiocarbonates (e.g., partially -C(S)SR) c C 1-20 Thiocarbamates (e.g., partially -C(S)N(R) c )2) The sugar moiety, peptide, polymer chain, or linker to another ascaridin molecule via a bond or carbon-containing linker, wherein R c Each occurrence is independently selected from -H, optionally substituted C. 1-12 Aliphatic, optionally substituted C 1-12 Heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain or linkage to another ascaridin molecule via a bond or carbon-containing linker, wherein R a and R b They can together form optionally substituted rings, which optionally contain one or more heteroatoms and optionally one or more unsaturated sites.

27. The composition of claim 26, wherein Z is selected from the group consisting of: i.–CH(CH3)–R 1 , where R 1 C is arbitrarily substituted 1-40 Aliphatic groups ii.–CH(CH3)–(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; iii.–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; iv.–CH(CH3)–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; v.–CH(CH3)–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; vi. –(CH2) n –CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; vii.–(CH2) n –CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides; viii.–(CH2) n –CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides; and ix.–(CH2) n –C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 -H, metal cation, or optionally substituted C 1-20 Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

28. The composition of claim 26, wherein Z is selected from the group consisting of: x.–CH(CH3)–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. xi.–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. xii.–CH(CH3)–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. xiii.–CH(CH3)–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. xiv.–(CH2) n –CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. xv.–(CH2) n –CH=CH-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. xvi.–(CH2) n –CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 The heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaridone molecule via a bond or carbon-containing linker. xvii.–(CH2) n –C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 Independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 Heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkages to another ascaridone molecule via bonds or carbon-containing linker portions; or xviii. Optionally unsaturated, Optionally substituted C 2-40 Side chains terminate at chain ends containing functional groups of nitrogen, oxygen, or sulfur.

29. The composition according to any one of claims 24 to 28, wherein the at least one ascaroside comprises 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 according to any one of claims 24 to 29, wherein the at least one ascaroside comprises ascr#18.

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

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

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

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

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

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

37. The composition of claim 36, wherein the ascaroside composition is substantially composed of one or more ascarosides and one or more carbonates (e.g., sodium bicarbonate or potassium bicarbonate).

38. The composition according to any one of claims 24 to 37, wherein the composition is characterized in that the one or more ascarosides exhibit a water solubility of at least 1, 3, 6, 9, 12, 15, 20 or 25 g / gal.

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

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

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

42. A method for treating crops or plants with one or more ascarosides, the method comprising: To obtain the ascaroside composition according to any one of claims 24 to 41, The ascaroside composition is mixed with water to form an ascaroside solution; as well as The ascaroside solution is applied to the crop or plant.

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

Images