Ascaroside salts

Abstract

The present application relates to salts of ascaroside, which can provide a variety of beneficial effects compared to the corresponding ascaroside. For example, certain ascaroside salts can provide beneficial nutrients to or nearby plants to which the salts are applied. Also provided herein are compositions and methods relating to such ascaroside salts.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to U.S. Provisional Patent Application No. 63 / 341,332, filed on May 12, 2022, entitled “Ascaroside Salts,” which is incorporated herein by reference. Technical Field

[0003] The present application generally relates to agrochemical compounds, compositions and methods for treating plants to enhance resistance to pathogens. Background Art

[0004] Ascaroside natural products are secondary metabolites produced by nematodes. A large number of structurally diverse ascarosides have been found in nature, and these molecules are thought to function as an evolutionarily conserved chemical language that nematodes use to control multiple aspects of their development. Ascarosides are also sensed by other organisms and have been shown to have a range of effects on a variety of organisms including bacteria, fungi, plants, and mammals, including humans. Ascarosides have the potential to be used as human pharmaceuticals, agrochemicals, and products for other diverse and valuable applications.

[0005] Studies have shown that when ascarosides are applied to plants, ascaroside treatments have been shown to enhance plant resistance to certain pathogens and / or induce and initiate plant defense responses that can inhibit pathogen growth and / or infection. By activating and / or activating the plant's innate defenses, ascarosides can thereby prevent the proliferation of pathogens and / or protect crops from the destructive effects of various pathogens.

[0006] It would be useful to provide other forms of ascarosides to alter the physical properties of the compounds, as well as to provide additional beneficial effects to the plants or other organisms to which the ascarosides are applied or administered. Summary of the invention

[0007] The present disclosure provides compositions and methods for ascaroside delivery. In certain embodiments, such compositions and methods can be used in an agrochemical context. Such compositions and methods generally relate to salts of ascarosides, which in some embodiments can provide various beneficial effects to an organism (e.g., a plant, an animal, or a microorganism) to which such salts are applied or administered.

[0008] The present disclosure includes, but is not limited to, the following embodiments.

[0009] Embodiment 1: A formula [A-(C(O)O) - ] p M p+A salt of , wherein: A is an ascaroside moiety; M is a metal or ammonium cation; and p is an integer from 1 to 3, and wherein, when p is 2 or 3, each A may be the same or different.

[0010] Embodiment 2: The salt according to Embodiment 1, wherein p is 1.

[0011] Embodiment 3: The salt according to Embodiment 1, wherein p is 2.

[0012] Embodiment 4: The salt according to Embodiment 1, wherein p is 3.

[0013] Embodiment 5: The salt of any one of Embodiments 1 to 4, wherein M is a metal.

[0014] Embodiment 6: The salt of Embodiment 5, wherein the metal is selected from the group consisting of potassium (K), calcium (Ca), magnesium (Mg), zinc (Zn), manganese (Mn), iron (Fe), copper (Cu), molybdenum (Mo) and nickel (Ni).

[0015] Embodiment 7: The salt of Embodiment 6, wherein the metal is selected from the group consisting of copper (Cu), zinc (Zn), manganese (Mn) and iron (Fe).

[0016] Embodiment 8: A salt as described in any one of Embodiments 1 to 4, wherein M is an ammonium cation or an analog thereof.

[0017] Embodiment 9: A salt comprising at least one boron atom coordinated to the ascaroside (A).

[0018] Embodiment 10: A salt as described in any one of Embodiments 1 to 9, wherein A has structure (I) Where: Z is an optionally substituted C 2-40 aliphatic group, and R a and R b Each of which is independently -H, or an optionally substituted moiety selected from the group consisting of: C 1-20 Aliphatic group, C 1-20 Acyl, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus-linked functional group, sulfur-linked functional group, silicon-linked functional group, C 2-20 Carbonate (e.g. part -C(O)OR c ), C 2-20 Carbamate (e.g., part -C(O)N(R c )2) C 2-20 Thioesters (e.g., moieties -C(S)R c ), C 2-20Thiocarbonates (e.g., moieties -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., part-C(S)SR c ), C 1-20 Thiocarbamates (e.g., moieties -C(S)N(R c ) 2), a sugar moiety, a peptide, a polymer chain, or a linker to another ascaroside molecule via a bond or a carbon-containing linker. c is independently selected at each occurrence from -H, optionally substituted C 1-12 aliphatic, optionally substituted C 1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linker to another ascaroside molecule via a bond or a carbon-containing linker, and wherein R a and R b Together they may form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

[0019] Embodiment 11: A salt as described in Embodiment 10, wherein Z is selected from the group consisting of: i. -CH(CH3)-R 1 , where R 1 is an optionally substituted C 1-40 Aliphatic group; ii.-CH(CH3)-(CH2) n -CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; ii. -CH(CH3)-(CH2) n -CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; iv. -CH(CH3)-(CH2) n -CH(OH)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; v. -CH(CH3)-(CH2) n -C(O)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; vi. -(CH2) n -CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; vii. -(CH2) n -CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; viii. -(CH2) n -CH(OH)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; and ix.-(CH2) n -C(O)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C1-20 heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0020] Embodiment 12: A salt as described in Embodiment 10 or Embodiment 11, wherein R a and R b Each is -H.

[0021] Embodiment 13: A salt as described in any one of Embodiments 10 to 12, wherein Z is -CH(CH3)-(CH2) n -CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0022] Embodiment 14: A salt as described in any one of Embodiments 1 to 13, wherein A is ascr#18.

[0023] Embodiment 15: A salt of the formula:

[0024]

[0025] wherein M is a metal or an ammonium cation; and p is an integer from 1 to 3.

[0026] Embodiment 16: A composition comprising the salt of any one of Embodiments 1 to 14.

[0027] Embodiment 17: The composition of embodiment 16, which is in solid form.

[0028] Embodiment 18: The composition of Embodiment 17, wherein the solid form comprises powder or granules.

[0029] Embodiment 19: The composition of embodiment 16, which is in liquid form.

[0030] Embodiment 20: The composition of Embodiment 19, wherein the liquid form is a sprayable formulation.

[0031] Embodiment 21: A composition as described in any of Embodiments 16 to 20, which further comprises one or more additional components selected from the group consisting of: surfactants, including emulsifiers, dispersants, foam formers, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, ultraviolet radiation absorbers, weathering stabilizers, plasticizers, release agents, fragrances, thermal insulation additives (e.g., silica), cross-linking agents, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, extenders / stickers, tackifiers, plant penetrants, safeners, spreaders, and wetting agents.

[0032] Embodiment 22: A method of enhancing the physical properties of ascarosides and providing one or more nutrients to a plant, comprising: contacting a plant or a part thereof, or soil surrounding the plant or a part thereof, with a salt as described in any one of Embodiments 1 to 15 or a composition as described in any one of Embodiments 16 to 21.

[0033] Embodiment 23: The method of Embodiment 22, wherein the part thereof is selected from the group consisting of roots, stems, leaves, seeds and flowers.

[0034] Embodiment 24: The method of Embodiment 22 or Embodiment 23, wherein the plant is a vegetable or fruit plant.

[0035] By reading the following specific embodiments and the accompanying drawings briefly described below, these and other features, aspects and advantages of the present disclosure will be understood. The present invention includes any combination of two, three, four or more of the above-mentioned embodiments and any two, three, four or more features or the combination of elements set forth in the present disclosure, regardless of whether these features or elements are clearly combined in the specific embodiment description of this paper. The present disclosure is intended to be read in an integral manner, so that any separable features or elements (in any one of its various aspects and embodiments) of the disclosed invention should be considered as intended to be combinable, unless the context clearly indicates otherwise. Other aspects and advantages of the present disclosure can be understood from the following.

[0036] definition

[0037] In order to make the present disclosure more easily understood, certain terms will first be defined below. Additional definitions of the following terms and other terms are set forth throughout the specification.

[0038] In this application, unless the context clearly indicates otherwise, the terms "a" and "an" may be understood to mean "at least one". As used in this application, the term "or" may be understood to mean "and / or". In this application, the terms "comprising" and "including" may be understood to cover the listed components or steps, either alone or with one or more additional 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, integers or steps.

[0039] As used herein, the terms "about" and "approximately" are used as equivalents. Unless otherwise specified, the terms "about" and "approximately" can be understood to allow standard variations, as understood by those of ordinary skill in the art. If a range is provided herein, endpoints are included. Any numeral with or without about / approximately used in this application is intended to cover any normal fluctuations understood by those of ordinary skill in the relevant art. In some embodiments, the term "about" or "approximately" refers to falling into 25%, 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1% or a numerical range in a smaller range on either direction (greater than or less than) of the reference value, unless otherwise specified or apparent from the context (unless the numeral exceeds 100% of a possible value).

[0040] The definitions of specific functional groups and chemical terms are described in more detail below. For purposes of the present invention, chemical elements are identified according to the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75th edition, inside cover, and specific functional groups are generally defined as described therein. In addition, the general principles of organic chemistry and specific functional moieties and reactivities are described in Organic Chemistry, Thomas Sorrell, University Science Books, Sausalito, 1999; Smith and March March's Advanced Organic Chemistry, 5th edition, John Wiley & Sons, Inc., New York, 2001; Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989; Carruthers, Some Modern Methods of Organic Synthesis, 3rd edition, Cambridge University Press, Cambridge, 1987; each of which is incorporated herein by reference in its entirety.

[0041] Some compounds provided herein may contain one or more asymmetric centers and therefore may exist in various stereoisomeric forms, for example, enantiomers and / or diastereomers. Therefore, the salts of the present invention and compositions thereof may be in the form of individual enantiomers, diastereomers or geometric isomers, or in the form of mixtures of stereoisomers. In certain embodiments, the salts and compositions of the present invention described herein may include enantiomerically pure salts. In certain other embodiments, a mixture of enantiomers or diastereomers is provided.

[0042] In addition, certain salts as described herein may have one or more double bonds, which may exist as Z or E isomers unless otherwise specified. Salts may be provided as individual isomers substantially free of other isomers, or as mixtures of various isomers (e.g., racemic mixtures of enantiomers).

[0043] As used herein, the term "isomer" includes any and all geometric isomers and stereoisomers. For example, "isomer" includes cis and trans isomers, E- and Z-isomers, R- and S-enantiomers, diastereomers, (D)-isomers, (L)-isomers, racemic mixtures thereof, and other mixtures thereof as fall within the scope of the present disclosure. For example, in some embodiments, a salt may be provided that is substantially free of one or more corresponding stereoisomers, and may also be referred to as "stereochemically enriched".

[0044] When a particular enantiomer is preferred, in some embodiments, the enantiomer may be substantially free of the opposite enantiomer, also referred to as "optically enriched". As used herein, "optically enriched" means that the salt consists of one enantiomer, and the ratio is significantly increased. In certain embodiments, the salt is composed of at least about 90% by weight of the enantiomer. In some embodiments, the salt is composed of at least about 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9% by weight of the enantiomer. In some embodiments, the enantiomeric excess of the provided salt is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9%. In some embodiments, enantiomers can be separated from the racemic mixture by any method known to those skilled in the art, including chiral high pressure liquid chromatography (HPLC) and the formation and crystallization of chiral salts, or prepared by asymmetric synthesis. See, for example, Jacques et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981); Wilen, SH et al., Tetrahedron 33: 2725 (1977); Eliel, EL Stereochemistry of Carbon Compounds (McGraw-Hill, NY, 1962); and Wilen, SH Tables of Resolving Agents and Optical Resolutions p. 268 (EL Eliel, Univ. of Notre Dame Press, Notre Dame, IN 1972), which are incorporated herein by reference.

[0045] As used herein, the terms "halo" and "halogen" refer to an atom selected from fluorine (F, -F), chlorine (Cl, -Cl), bromine (Br, -Br) and iodine (I, -I).

[0046] As used herein, the term "aliphatic" or "aliphatic group" means a hydrocarbon moiety that may be straight chain (i.e., unbranched), branched, or cyclic (including fused, bridged, and spiro-fused polycyclics) and may be fully saturated or may contain one or more unsaturated units but is not aromatic. Unless otherwise specified, aliphatic groups contain 1-30 carbon atoms. In certain embodiments, aliphatic groups contain 1-12 carbon atoms. In certain embodiments, aliphatic groups contain 1-8 carbon atoms. In certain embodiments, aliphatic groups contain 1-6 carbon atoms. In some embodiments, aliphatic groups contain 1-5 carbon atoms, in some embodiments, aliphatic groups contain 1-4 carbon atoms, in other embodiments, aliphatic groups contain 1-3 carbon atoms, and in other embodiments, aliphatic groups contain 1-2 carbon atoms. Suitable aliphatic groups include, but are not limited to, straight or branched alkyl, alkenyl, and alkynyl groups and mixtures thereof such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl.

[0047] 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 a heteroatom (eg, oxygen, nitrogen, sulfur, phosphorus, boron, etc.).

[0048] As used herein, the term "unsaturated" means a moiety having one or more double or triple bonds.

[0049] The term "alkyl" as used herein refers to a saturated, straight or branched hydrocarbon group derived from an aliphatic portion containing one to six carbon atoms by removing a single hydrogen atom. Unless otherwise specified, an alkyl group contains 1-12 carbon atoms. In certain embodiments, the alkyl group contains 1-8 carbon atoms. In certain embodiments, the alkyl group contains 1-6 carbon atoms. In some embodiments, the alkyl group contains 1-5 carbon atoms, in some embodiments, the alkyl group contains 1-4 carbon atoms, in other embodiments, the alkyl group contains 1-3 carbon atoms, and in other embodiments, the alkyl group contains 1-2 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.

[0050] As used herein, the term "alkenyl" refers to a monovalent group derived from a straight or branched aliphatic moiety, the alkenyl having at least one carbon-carbon double bond by removing a single hydrogen atom. Unless otherwise specified, the alkenyl group contains 2-12 carbon atoms. In certain embodiments, the alkenyl group contains 2-8 carbon atoms. In certain embodiments, the alkenyl group contains 2-6 carbon atoms. In some embodiments, the alkenyl group contains 2-5 carbon atoms, in some embodiments, the alkenyl group contains 2-4 carbon atoms, in other embodiments, the alkenyl group contains 2-3 carbon atoms, and in other embodiments, the alkenyl group contains 2 carbon atoms. Alkenyl groups include, for example, vinyl, propenyl, butenyl, 1-methyl-2-butene-1-yl, etc.

[0051] The term "aryl", used alone or as part of a larger moiety in "aralkyl", "aralkyloxy", or "aryloxyalkyl", refers to monocyclic and polycyclic ring systems having a total of 5 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" can be used interchangeably with the term "aromatic ring". In certain embodiments, "aryl" refers to an aromatic ring system including, but not limited to, phenyl, biphenyl, naphthyl, anthracenyl, etc., which may carry one or more substituents. Also included within the scope of the term "aryl", as used herein, are groups in which an aromatic ring is fused to one or more additional rings, such as benzofuranyl, indanyl, phthalimido, or tetrahydronaphthyl, etc.

[0052] As described herein, salts as provided herein may contain "optionally substituted" parts. In general, whether or not the term "optionally" is added in front, the term "substituted" means that one or more hydrogens of the specified part are replaced by suitable substituents. Unless otherwise specified, the "optionally substituted" group may have a suitable substituent at each substitutable position of the group, and when more than one position in a given structure can be substituted by more than one substituent selected from a specified group, the substituent may be the same or different at each position. The combination of the envisioned substituents is preferably a combination of compounds / salts that form stability or chemical feasibility. The term "stable" as used herein refers to a compound or salt that is substantially unchanged when subjected to conditions that allow compound preparation, detection, and in certain embodiments, its recovery, purification, and use for one or more purposes disclosed herein.

[0053] Suitable monovalent substituents on the substitutable carbon atoms of the "optionally substituted" group are independently halogen; -(CH2) 0-4 R°; -(CH2) 0-4 OR°; -O-(CH2) 0-4 C(O)OR°; -(CH2) 0-4 CH(OR°)2; -(CH2)0-4 SR°; -(CH2) 0- 4Ph, which can be substituted 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) 0-4 S(O)2R°; -(CH2) 0-4 S(O)2OR°; -(CH2) 0-4 OS(O)2R°;-S(O)2NR°2;-(CH2) 0-4 S(O)R°; -N(R°)S(O)2NR°2; -N(R°)S(O)2R°; -N(OR°)R°; -C(NH)NR°2; -P(O)2R°; -P(O)R°2; -OP(O)R°2; -OP(O)(OR°)2; SiR°3; -(C 1-4 Straight or branched alkylene)ON(R°)2; or -(C1-4 linear or branched alkylene) C(O)ON(R°)2, wherein each R° may be substituted as defined below and is independently hydrogen, C 1-8 Aliphatic, -CH2Ph, -O(CH2) 0-1 Ph, or a 5-6 membered saturated, partially unsaturated and or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur, or, although as defined above, two independent occurrences of R° together with their intervening atoms form a 3-12 membered saturated, partially unsaturated or aryl monocyclic or polycyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur, said R° may be substituted as defined below.

[0054] Suitable monovalent substituents on R° (or two independent occurrences of R° together with their intervening atoms to form a ring) are independently halogen, -(CH2) 0-2 R · 、-(halogen R · )、-(CH2) 0-2 OH, -(CH2) 0-2 OR · 、-(CH2) 0-2 CH(OR · )2; -O(halogen 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 or branched alkylene)C(O)OR · or -SSR · Each R · is unsubstituted or, in the case of being preceded by "halo", is substituted only by one or more halogens, and is independently selected from 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. Suitable divalent substituents on a saturated carbon atom of R° include =0 and =S.

[0055] Suitable divalent substituents on a saturated carbon atom of an "optionally substituted" group include the following: =O, =S, =NNR*2, =NNHC(O)R*, =NNHC(O)OR*, =NNHS(O)2R*, =NR*, =NOR*, -O(C(R*2)) 2-3 O-or-S(C(R*2)) 2-3 S-, wherein each independent occurrence of R* is selected from hydrogen, C 1-6 aliphatic (which may be substituted as defined below) or an unsubstituted 5-6 membered saturated, partially unsaturated or aromatic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur. Suitable divalent substituents attached to adjacent substitutable carbons of an "optionally substituted" group include: -O(CR*2) 2-3 O-, wherein each independent occurrence of R* is selected from hydrogen, C 1-6 an aliphatic group, or an unsubstituted 5-6 membered saturated, partially unsaturated or aromatic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur.

[0056] Suitable substituents on the aliphatic group of R* include halogen, -R · 、-(halogen R · ), -OH, -OR · 、-O(halogen R · )、-CN、-C(O)OH、-C(O)OR · 、-NH2、-NHR · 、-NR · 2 or -NO2, where each R · is unsubstituted or, when preceded by "halo", substituted only by 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.

[0057] Suitable substituents on a substitutable nitrogen of an "optionally substituted" group include

[0058] or Each of these are independently hydrogen, substituted C1-6 aliphatic, unsubstituted -OPh or an unsubstituted 5-6 membered saturated, partially unsaturated or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur, or, notwithstanding the definitions given above, two independent occurrences of Together with their intervening atom(s), they form a 3-12 membered saturated, partially unsaturated or aromatic monocyclic or bicyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur.

[0059] Suitable substituents on the aliphatic group are independently halogen, -R · 、-(halogen R · ), -OH, -OR · 、-O(halogen R · )、-CN、-C(O)OH、-C(O)OR · 、-NH2、-NHR · 、-NR · 2 or -NO2, where each R · is unsubstituted or, when preceded by "halo", substituted only by one or more halogens, and is independently C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0- 1Ph or a 5-6 membered saturated, partially unsaturated or aromatic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur.

[0060] As used herein, the term "substantially" refers to the qualitative condition of exhibiting the full or nearly full extent or degree of a characteristic or property of interest.

[0061] A convention of naming ascarosides with a prefix of several letters followed by a pound sign (#) and a number is sometimes used (e.g., ascr#18). This convention is used in the scientific literature, and one skilled in the art will understand that each such name is associated with 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 C. elegans Small Molecule Identifier Database (SMID-DB) (maintained at http: / / www.smid-db.org).

[0062] The term "pathogen" refers to any bacterium, fungus, oomycete, virus, nematode (eg, cyst nematode or root knot nematode), or insect that is pathogenic to plants. BRIEF DESCRIPTION OF THE DRAWINGS

[0063] The present teachings described herein may be more fully understood through the following description of various illustrative embodiments when read in conjunction with the accompanying drawings. It should be understood that the drawings described below are for illustrative purposes only and are not intended to limit the scope of the present teachings in any way. The foregoing and other objects, aspects, features and advantages of the present disclosure may be more readily appreciated and better understood by reference to the following description in conjunction with the accompanying drawings, wherein:

[0064] Figure 1 Shown is a graph of the relative activity of ascr#18 and its zinc salt in an assay measuring protection of wheat plants from the fungal pathogen Bipolaris sorokiniana. DETAILED DESCRIPTION

[0065] The present disclosure relates to ascarosides in salt form (also referred to herein as "ascaroside salts"), and compositions and methods relating to such ascaroside salts. In some embodiments, use of ascarosides in salt form can provide various formulation benefits (e.g., improved handling characteristics and / or simplified or improved incorporation in an agrochemical or pharmaceutical composition) compared to the corresponding ascarosides. In some embodiments, use of certain salt forms of ascarosides can also provide beneficial effects to plants to which the ascaroside salts are applied, beyond those typically provided by application of ascarosides, e.g., provision of micronutrients, macronutrients, and / or other beneficial molecules.

[0066] Ascarosides are derivatives of ascarylose, a dideoxy sugar lacking hydroxyl groups at positions 3 and 6. Ascarosides have the general structure shown in Formula I:

[0067]

[0068] in:

[0069] Z is an optionally substituted C 2-40 an aliphatic group, and

[0070] R a and R b Each of the following is independently -H, or an optionally substituted moiety selected from the group consisting of: C 1-20 Aliphatic group, C 1-20 Acyl, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus-linked functional group, sulfur-linked functional group, silicon-linked functional group, C 2-20 Carbonate (e.g. part -C(O)OR c ), C 2-20 Carbamate (e.g., part -C(O)N(R c )2) C 2-20 Thioesters (e.g., moieties -C(S)R c), C 2-20 Thiocarbonates (e.g., moieties -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., part-C(S)SR c ), C 1-20 Thiocarbamates (e.g., moieties -C(S)N(R c ) 2), a sugar moiety, a peptide, a polymer chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, wherein R c is independently selected at each occurrence from -H, optionally substituted C 1-12 aliphatic, optionally substituted C 1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, and wherein R a and R b Can be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

[0071] In certain embodiments, Z is:

[0072] (i)-CH(CH3)-R 1 , where R 1 is an optionally substituted C 1-40 aliphatic groups;

[0073] (ii) -CH(CH3)-(CH2) n -CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0074] (iii) -CH(CH3)-(CH2) n -CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0075] (iv) -CH(CH3)-(CH2) n -CH(OH)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0076] (v) -CH(CH3)-(CH2) n -C(O)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0077] (vi)-(CH2) n -CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0078] (vii)-(CH2) n -CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0079] (viii)-(CH2) n -CH(OH)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; or

[0080] (ix)-(CH2) n -C(O)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0081] In certain embodiments, Z is:

[0082] (x)-CH(CH3)-(CH2) n -CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0083] (xi)-CH(CH3)-(CH2) n -CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0084] (xii)-CH(CH3)-(CH2) n -CH(OH)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0085] (xiii) -CH(CH3)-(CH2) n -C(O)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0086] (xiv)-(CH2) n -CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0087] (xv)-(CH2) n -CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0088] (xvi)-(CH2) n -CH(OH)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; or

[0089] (x)-(CH2) n -C(O)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0090] In certain embodiments, R a Yes -H.

[0091] In certain embodiments, R b Yes -H.

[0092] In certain embodiments, R a and R b In certain embodiments, R a and R b All are -H.

[0093] In certain embodiments, R a and R b In certain embodiments, R a Yes -H, and R b is a group other than -H. In certain embodiments, R a is a group other than -H and R b is -H. In certain embodiments, R a Yes -H and R b is a paraben. In certain embodiments, R a Yes -H and R b is indole-3-carboxylate. In certain embodiments, R a Yes -H and R b is (E)-2-methyl-2-butenoate. In certain embodiments, R a Yes -H and R b is a picolinate. In certain embodiments, R a Yes -H and R b In certain embodiments, R a Yes -H and R b is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, R a Yes -H and R b It is 4-((4-hydroxyphenethyl)amino)-4-oxobutanoate.

[0094] In certain embodiments, R a and R b are all -H, and Z is selected from the formulae defined in (i) to (ix) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (i) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (ii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (iii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (iv) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (v) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (vi) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (vii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (viii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (ix) above. In certain embodiments, R a and R b are -H, and Z conforms to Formula (x) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (xi) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (xii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (xiii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (xiv) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (xv) above. In certain embodiments, R a and R bare -H, and Z conforms to formula (xvi) above. In certain embodiments, R a and R b All are -H, and Z conforms to formula (xvii) above.

[0095] In certain embodiments, R 2 is -H. In certain embodiments, R 2 is a metal cation. In certain embodiments, R 2 is an organic cation (e.g., a nitrogen or phosphorus-centered cationic group). 2 is an optionally substituted C 1-20 In certain embodiments, R 2 is an optionally substituted C 1-12 In certain embodiments, R 2 is an optionally substituted C 1-8 In certain embodiments, R 2 is an optionally substituted C 1-6 In certain embodiments, R 2 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl. 2 is an optionally substituted aromatic group. In certain embodiments, R 2 is a glycoside. In certain embodiments, R 2 In certain embodiments, R 2 In certain embodiments, R 2 Contains nucleotides.

[0096] In certain embodiments, at least one R 3 is -H. In certain embodiments, both R 3 The group is -H. In certain embodiments, at least one R 3 is an optionally substituted C 1-20 In certain embodiments, two R 3 The group is an optionally substituted C 1-20 aliphatic groups, which may be the same or different. In certain embodiments, at least one R 3 is an optionally substituted C 1-12 In certain embodiments, at least one R 3 is an optionally substituted C 1-8 In certain embodiments, at least one R 3 is an optionally substituted C 1-6 In certain embodiments, at least one R 3is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl. 3 is -CH2CH2OH. In certain embodiments, at least one R 3 Yes -CH2CH2OR 2 , where R 2 As defined in the genus and subgenus herein. In certain embodiments, at least one R 3 is an optionally substituted aromatic group. In certain embodiments, at least one R 3 In certain embodiments, at least one R 3 In certain embodiments, at least one R 3 At least one R 3 In certain embodiments, at least one R 3 Contains nucleotides.

[0097] In certain embodiments, the ascaroside is selected from the group consisting of:

[0098]

[0099] Where x is an integer from 1 to 22, and R a , R b and R 2 Each of which is as defined above and in the genera and subgenera herein.

[0100] In certain embodiments, the ascaroside is selected from the group consisting of:

[0101]

[0102] Where x, R a and R b Each of which is as defined above and in the genera and subgenera herein.

[0103] In certain embodiments, the ascaroside is selected from the group consisting of:

[0104]

[0105] Where y is an integer from 1 to 20, and R a , R b and R 2 Each of which is as defined above and in the genera and subgenera herein.

[0106] In certain embodiments, the ascaroside is selected from the group consisting of:

[0107]

[0108] Where y, R a and R b Each of which is as defined above and in the genera and subgenera herein.

[0109] In certain embodiments, the ascaroside is selected from the group consisting of:

[0110]

[0111] Where x is an integer from 1 to 22, and R 2 As defined above and in the genus and subgenera herein.

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

[0113]

[0114] wherein x is as defined above and in the genera and subgenera herein.

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

[0116]

[0117] Where y is an integer from 1 to 20, and R 2 As defined above and in the genus and subgenera herein.

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

[0119]

[0120] wherein y is as defined above and in the genus and subgenera herein.

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

[0122]

[0123] Where x is an integer from 1 to 22, and R a , R b and R 3 Each of which is as defined above and in the genera and subgenera herein.

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

[0125]

[0126] where x and R 3 Each of which is as defined above and in the genera and subgenera herein.

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

[0128]

[0129] Where y is an integer from 1 to 20, and R a , R b and R 2 Each of which is as defined above and in the genera and subgenera herein.

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

[0131]

[0132] where y and R 3 Each of which is as defined above and in the genera and subgenera herein.

[0133] In one embodiment, the ascarosides used in the context of the present disclosure have the general structure (I), wherein Z is -CH(CH3)-(CH2) n -CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides, and can be used to inhibit the growth of human pathogenic bacteria in or on plants.

[0134] In one embodiment, the ascarosides used in the context of the present disclosure have the general structure (I), wherein Z is -CH(CH3)-(CH2) n -CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0135] In one embodiment, the ascaroside used in the present invention has the general structure (I), wherein Z is -CH(CH3)-(CH2) n -CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 The aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides may be used to inhibit the growth of pathogenic bacteria in or on plants.

[0136] In one embodiment, the ascarosides useful in the present invention have the general structure (I), wherein Z is -CH(CH3)-(CH2) n -CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0137] Specific ascarosides useful in the present invention include, but are not limited to, ascr#7 and ascr#18.

[0138]

[0139] In certain embodiments, the ascarosides used in the provided salts, compositions, and / or methods are selected from the group consisting of ascr#9, ascr#12, ascr#14, ascr#1, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, ascr#24, ascr#26, ascr#28, ascr#30, ascr#32, ascr#34, and ascr#36. In certain embodiments, the ascarosides used in the provided salts, compositions, and / or methods are selected from the group consisting of ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. In certain embodiments, the ascarosides used in the provided methods are selected from the group consisting of ascr#9, ascr#14, ascr#10, and ascr#18.

[0140] In certain embodiments, the ascaroside used in provided salts, compositions, and / or methods is selected from the group consisting of ascr#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, the ascaroside used in provided salts, compositions, and / or methods is selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22. In certain embodiments, the ascaroside used in provided salts, compositions, and / or methods is selected from the group consisting of bhas#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, the ascaroside used in provided salts, compositions, and / or methods is selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

[0141] In certain embodiments, the ascaroside used in provided salts, compositions, and / or methods 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.

[0142] In certain embodiments, the ascaroside used in provided salts, compositions, and / or methods 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.

[0143] In certain embodiments, the ascaroside used in provided salts, compositions, and / or methods is selected from the group consisting of ascr#18, oscr#16, oscr#17, oscr#15, bhas#18, bhos#16, glas#18, dhas#18, ibha#18, ibho#16, icas#18, icos#15, icos#16, and any combination of two or more of these.

[0144] Ascarosides can be obtained from natural sources (e.g., nematodes) or prepared synthetically. Ascarosides can be prepared synthetically, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascarosides. An exemplary method for preparing ascarosides includes: providing 1-O-substituted rhamnose as a raw material; forming a monosulfonate on the 3-OH group of the raw material; and treating the monosulfonate with a hydride source to form a 1-O-substituted ascarosides. In certain embodiments, the formation of the monosulfonate is carried out on a substrate without a hydroxyl protecting group at position 2 or 4 of the rhamnose raw material. In certain embodiments, such methods include contacting the raw material with a sulfonating agent (i.e., a sulfonyl halide, a sulfonic anhydride, or a similar reagent) in the presence of a Lewis acid. Specific details about the synthesis of 1-O-substituted ascarosides can be found in PCT application PCT / IB2021 / 056981, which is incorporated herein by reference.

[0145] As described above, the present disclosure provides ascarosides in salt form. Ascaroside salts can be formed by appropriate reagents, for example, at any suitable acidic or basic functional group on the ascaroside molecule.

[0146] For example, in some embodiments, carboxylate salts (also referred to as carboxylate salts) are provided. Such salts can be described according to Formula II below, where "M" is a metal (or other cation) and "A" is the remainder of the ascaroside molecule to which the carboxylic acid moiety is attached (e.g., the structure according to Formula I provided above):

[0147]

[0148] wherein p represents an integer from 1 to 4. In some embodiments, p is 1 and the salt comprises one ascaroside anion and one "M" cation (charged with +1). In some embodiments, p is 2 and the salt comprises two ascaroside anions and one "M" cation (charged with +2). In some embodiments, p is 3 and the salt comprises three ascaroside anions and one "M" cation (charged with +3). In some embodiments, p is 4 and the salt comprises four ascaroside anions and one "M" cation (charged with +4). In embodiments where p is greater than 1, the ascaroside anions present in the salt may be the same or different.

[0149] Referring to the structure of the ascaroside in Formula I above, it is noteworthy that carboxylates can be formed, for example, at the "OR a " and / or "OR b "Substituents to form carboxylates. In some embodiments, the carboxylic acid may be in the OR a and / or b Substituents are formed, where R a and / or R b Yes-LC(O)OR c , wherein L is an optionally substituted divalent linking group comprising one or more carbon atoms and optionally containing one or more heteroatoms, and wherein R c is H. In some embodiments, the carboxylic acid may be in OR a and / or b Substituents are formed, where R a and / or R b is a sugar moiety (e.g., a sugar acid) comprising a carboxylic acid group. In some embodiments, the carboxylic acid may be present in the OR a and / or b Substituents are formed, where R a and / or R b is a peptide comprising a carboxylic acid group. In some embodiments, the carboxylic acid may be present in the OR a and / or b Substituents are formed, where R a and / or R b is a polymer comprising carboxylic acid groups. In some embodiments, the carboxylic acid may be present in the OR a and / or b Substituents are formed, where R c is a polymer chain containing carboxylic acid groups. In some embodiments, the carboxylic acid can be in the OR a and / or b Substituents are formed, where R a and / or R b is a monoester of a diacid. In certain embodiments, such compounds are derived from the reaction of compounds wherein R a and / or R b is -H, wherein a cyclic anhydride 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:

[0150]

[0151] where x and R 2 Each of which is as defined above and in the genera and subgenera herein.

[0152] Referring again to the structure of the ascaroside in Formula I above, it is noteworthy that a carboxylic acid can be formed, for example, at the OZ substituent of the tetrahydropyranyl ring. In some embodiments, a 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)-CH-CO2R 2 ; -CH(CH3)-(CH2) n -C(O)-CH-CO2R 2 ; -(CH2) n -CO2R 2 ; -(CH2) n -CH=CH-CO2R 2 ; and -(CH2) n -CH(OH)-CH-CO2R 2 When n is an integer from 1 to 40, and R 2 is -H or optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside containing a carboxylic acid group, an amino acid, a peptide or a nucleotide.

[0153] In certain embodiments, the linker group -L- comprises an optionally substituted C 1-20 Aliphatic group, C 1-20 Such linking groups may be via ether bonds, ester bonds, carbonate bonds, carbamate bonds (e.g., A-OC(O)NR 3 -), thioester bonds (e.g., A-OC(S)-), thiocarbamate bonds (e.g., A-OC(S)NR 3 -), a thiocarbonate bond (e.g., A-OC(S)O-), a dithiocarbonate bond (e.g., A-OC(S)S-)), a sulfonate bond (e.g., A-OSO2-), or attached to an oxygen atom on the ascaroside molecule through a phosphorus atom.

[0154] In one embodiment, a salt of ascr#18 is provided, for example, according to the following formula:

[0155]

[0156] The negative charge is shown to be delocalized on the oxygen atom of the carboxylic acid.

[0157] The present disclosure is not limited to carboxylate salts of ascarosides. Salts that can be formed with other functional groups on the ascaroside molecule are also encompassed by the present disclosure. For example, when the ascaroside contains an amine group (e.g., in R a , R b When the ascaroside is present in the substituent group (e.g., ...

[0158] Non-limiting, representative metal salts of ascarosides formed via pendant carboxylic acid groups are shown below:

[0159]

[0160] wherein x is as defined above and in the genera and subgenera herein.

[0161] Representative "salts" of ascarosides formed via the hydroxyl groups of the ascarylose are shown below:

[0162]

[0163] wherein x is as defined above and in the genera and subgenera herein.

[0164] The composition of "M" (e.g., as shown in Formula II and IIb above) can vary greatly. In some embodiments, M is a metal. Suitable metals are not particularly limited and are selected from alkali metals / Group 1 metals, alkaline earth metals / Group 2 metals and transition metals in various embodiments. In some embodiments, M is a semimetal or nonmetal selected from the main group elements. In some embodiments, M is an organic cation such as ammonium, guanidinium, amidinium, pyridinium, phosphonium, sulfonium or any similar cation centered on nitrogen, phosphorus or sulfur or its analogs.

[0165] In some embodiments, M comprises a plant micronutrient or a plant macronutrient. Plant micronutrients and macronutrients include, but are not limited to, nitrogen (N), phosphorus (P), potassium (K), calcium (Ca), magnesium (Mg), boron (B), silicon (Si), zinc (Zn), manganese (Mn), iron (Fe), copper (Cu), molybdenum (Mo), and nickel (Ni). Those skilled in the art will appreciate that not all such micronutrients and macronutrients can form salts with ascaroside in the same manner.

[0166] For example, salts of plant nutrients such as potassium, calcium, magnesium, zinc, manganese, iron, copper, molybdenum, and nickel can be formed with the carboxylic acid on the ascaroside in some embodiments (e.g., according to Formula II or IIb above). Nitrogen can be provided in the form of an ammonium or guanidinium salt of the ascaroside (e.g., where M is NH 1 or H2N 1=C(NH2)2 or an ammonium or guanidinium salt of an ascaroside analog) (e.g., wherein NH4 + or H2N + =C(NH2)2, one or more of the H atoms are replaced by an alkyl group). Phytonutrients such as boron, silicon, and molybdenum may not readily form salts with carboxylic acids, but may coordinate to free OH present on the ascaroside molecule, for example in the form of borates, silicates, or molybdates, to form suitable salts. Thus, in some embodiments, salts comprising at least one boron atom coordinated to an ascaroside, salts comprising at least one silicon atom coordinated to an ascaroside, or salts comprising at least one molybdenum atom coordinated to an ascaroside are provided.

[0167] The salts provided herein can be prepared by modifying conventional methods known in the art. For example, salts are generally the result of reactions between acids and bases. Thus, ascaroside salts provided in Formula II or IIb above can be prepared, for example, by combining one or more ascaroside molecules (the number of molecules corresponding to the number "p", i.e., equal to the charge on "M" (e.g., a metal or ammonium cation)) with M in solution. P+ The solution is prepared by combining the two salts, the pH of which is sufficient to provide the desired salt. In other embodiments, the salt can be produced by a metathesis reaction, in which the cation and / or anion in the first salt is replaced by a different cation or anion in the second salt.

[0168] In some embodiments, the ascaroside salts disclosed herein can exhibit enhanced physical properties compared to the corresponding ascaroside molecules. For example, in some embodiments, the ascaroside salts can exhibit greater solubility in certain solvents (e.g., water) than the corresponding ascaroside, thereby simplifying the preparation of certain formulations. In some embodiments, providing the ascaroside in salt form (rather than in neutral / free acid or free base form) renders the ascaroside more compatible with certain components of a desired composition, thereby stabilizing the resulting ascaroside-containing composition.

[0169] In some embodiments, for example, where M is a plant micronutrient or macronutrient, ascaroside salts as provided herein provide advantages beyond the beneficial effects of the formulation, for example, providing nutrients to the applied plant (or nearby plants). Thus, in some embodiments, the salts provided herein can be referred to as ascaroside-based micronutrients or ascaroside-based macronutrients. In some embodiments, the salts described herein have improved application characteristics (e.g., enhanced ability to wet or adhere to surfaces such as leaves or skin), enhanced bioavailability, and / or enhanced absorption (e.g., absorption by plants, microorganisms, or animals such as mammals).

[0170] In certain embodiments, the ascaroside salts and compositions containing ascaroside salts provided herein comprise "multifunctional" products. In addition to providing nutrients as described above, in certain embodiments, such multifunctional products combine ascarosides with molecules having other different or complementary biological activities. In certain embodiments, such multifunctional products include salts formed by anions of ascarosides and cations of molecules having biological activity as pesticides (e.g., insecticides, fungicides, herbicides, miticides, nematicides), as antimicrobials (e.g., antibiotics, antifungals, etc.), as antivirals, as signaling molecules (e.g., pheromones, hormones, etc.), or as vitamins or nutrients. Such multifunctional products can avoid the need for multiple applications (e.g., drug or agricultural treatment application), thereby saving costs and / or simplifying treatment methods.

[0171] In certain embodiments, provided herein are salts or compositions comprising salts of ascaroside anions and cationic insecticide molecules. In certain embodiments, provided herein are salts or compositions comprising salts of ascaroside anions and cationic insecticide molecules. In certain embodiments, provided herein are salts or compositions comprising salts of ascaroside anions and cationic herbicides molecules. In certain embodiments, provided herein are salts or compositions comprising salts of ascaroside anions and cationic fungicides molecules. In certain embodiments, provided herein are salts or compositions comprising salts of ascaroside anions and cationic antimicrobial molecules. One skilled in the art will appreciate the identification (and provision or synthesis) of suitable bioactive cationic molecules, just as such salts are formed using simple acid-base chemistry or ion metathesis reaction techniques.

[0172] In certain embodiments, the salts or compositions provided herein comprise salts of ascaroside anions and cationic signaling molecules. In certain embodiments, the salts or compositions provided herein comprise salts of ascaroside anions and cationic plant hormones. In certain embodiments, the salts or compositions provided herein comprise salts of ascaroside anions and cationic pheromones.

[0173] In certain embodiments, provided herein are salts or compositions comprising salts of ascaroside anions and cationic therapeutic molecules. In certain embodiments, provided herein are salts or compositions comprising salts of ascaroside anions and cationic vitamins. In certain embodiments, provided herein are salts or compositions comprising salts of ascaroside anions and cationic drugs. In certain embodiments, provided herein are salts or compositions comprising salts of ascaroside anions and cationic hormones. In certain embodiments, provided herein are salts or compositions comprising salts of ascaroside anions and cationic vitamins.

[0174] In certain embodiments, the ascaroside salts described herein can be used to treat living plants, soil surrounding plants, or soil in which seeds / seedlings are to be planted. In some embodiments, an ascaroside salt (or a composition comprising such an ascaroside salt) is applied to a portion of a plant, e.g., one or more of a root, stem, leaf, seed, and / or flower. Such methods can be performed at any one or more stages of a plant's life cycle, e.g., from seed to seedling to growing plant to before harvest.

[0175] In certain embodiments, provided ascaroside salts include a second biologically active molecule that can be an anion, and the composition can include a mixed salt in which the ascaroside and the second biologically active anionic molecule share a common cation. In certain embodiments, such mixed salts can include a polycation that is capable of forming a salt with both the ascaroside and the second biologically active anionic molecule. In certain embodiments, such mixed salts can include a common monocationic species or a mixture of monocations that balance the anionic charge of the ascaroside and the second biologically active anionic molecule.

[0176] In some embodiments, the disclosed treatment methods can protect growing plants in the manner described in U.S. Pat. No. 10,136,595, which is incorporated herein by reference in its entirety. For example, such methods can enhance pathogen resistance and / or induce one or more plant defense responses (thereby inhibiting pathogen growth and / or infection) in (or near) plants to which an ascaroside salt (or a composition comprising such an ascaroside salt) is applied. The disclosed methods can enhance resistance to pathogens including, but not limited to, oomycetes, bacteria, nematodes, viruses, and insects, such as, but not limited to, Pseudomonas syringae, Phytophthora infestans, Blepharitis graminis, Heterodera schachtii, Meloidogyne incognita, Meloidogyne hapla, and turnip crinkle virus.

[0177] In some embodiments, the disclosed treatment methods can protect plants or plant-based products from contamination by pathogens, or prevent or delay the onset of plant spoilage, or function in a manner as described in patent applications PCT / US22 / 81895 and PCT / US23 / 17947 (each of which is incorporated herein by reference in its entirety).

[0178] The exact method of treating plants or soil with ascaroside salts or compositions containing ascaroside salts is not particularly limited. Plants and / or soil can be treated in accordance with the present disclosure, for example, by soaking, spraying, evaporation, atomization, broadcasting, painting, side application, or in-furrow application. For example, in certain embodiments, plants or soil can be sprayed with a suitable liquid composition, a solid plastic mulch composition can be applied to the soil around the plant, and / or in-furrow application or side application of a granular composition can be provided.

[0179] The plant type that can be processed according to the method disclosed in the present invention is not particularly limited, and can be, for example, fruit and vegetable plants, trees and shrubs. The non-limiting examples of the plant that can be processed according to the disclosed method include, but are not limited to, the plant selected from the group consisting of the following: tobacco, Arabidopsis, tomato, barley, potato, sweet potato, yam, cotton, soybean, strawberry, beet, corn, rice, wheat, rye, oat, sorghum, millet, bean, pea, apple, banana, pear, cherry, peach, plum, apricot, almond, grape, kiwi, mango, melon, papaya, walnut, hazelnut, pistachio, raspberry, blackberry, loganberry, blueberry, cranberry, orange, lemon, grapefruit, tangerine, lettuce, carrot, onion, broccoli, cabbage, avocado, cocoa, cassava, cotton and flax.

[0180] In the methods provided herein, the ascaroside salts can be applied directly to plants and / or soil, or can be formulated into compositions that can be applied to plants and / or soil. Therefore, the compositions provided by the present disclosure generally comprise at least one ascaroside salt and one or more inert ingredients (e.g., one or more agronomically acceptable carriers). Preferably, the methods of the present disclosure use non-toxic carriers.

[0181] The term "agronomically acceptable carrier" includes any carrier suitable for application to plants or soil, for example, conventional excipients in formulation technology, such as for forming solutions (e.g., directly sprayable or directly dilutable solutions), emulsions (e.g., emulsion concentrates and diluted emulsions), wettable powders, suspensions, soluble powders, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, polymer material encapsulation agents, coatable pastes, natural and synthetic materials impregnated with active compounds / salts, and microcapsules in polymeric substances. These compositions can be produced in a known manner, for example, by mixing the ascaroside salts with one or more agriculturally acceptable carriers, such as liquid solvents or solid carriers, optionally with additional components including, but not limited to, surfactants, including emulsifiers, dispersants, foam formers, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, ultraviolet radiation absorbers, weathering stabilizers, plasticizers, release agents, fragrances, thermal insulation additives (e.g., silica), crosslinking agents, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, extenders / stickers, tackifiers, plant penetrants, safeners, spreaders and wetting agents, and the like.

[0182] In some embodiments, the ascaroside salt is the only active agent in the composition. In some embodiments, the composition comprises one or more additional ascarosides (e.g., in another salt form or in a non-salt form). In some embodiments, the composition comprises one or more other active agents (e.g., one or more pesticides (e.g., insecticides, fungicides, herbicides, miticides, nematicides), antimicrobials (e.g., antibiotics, antifungals, etc.), antivirals, signaling molecules (e.g., pheromones, hormones, etc.), vitamins, nutrients or fertilizers, etc.). The compositions containing ascaroside salts provided herein can be in a variety of forms, including solid and liquid forms.

[0183] If the agronomically acceptable carrier is water, in some embodiments, an organic solvent as an auxiliary liquid solvent may be optionally added. Suitable liquid solvents include, for example, aromatic compounds (e.g., xylene, toluene, and alkylnaphthalene); chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons (e.g., chlorobenzene, vinyl chloride, and methylene chloride); aliphatic hydrocarbons (e.g., cyclohexane); paraffins (e.g., petroleum fractions, mineral oils, and vegetable oils); alcohols (e.g., ethanol, butanol, or glycols and their ethers and esters, including propylene glycol); ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone) and strong polar solvents (e.g., dimethylformamide and dimethyl sulfoxide).

[0184] Suitable agriculturally acceptable solid carriers include, for example, ammonium salts and ground natural minerals (e.g., kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth); ground synthetic minerals (e.g., highly dispersed silica, alumina and silicates); crushed and fractionated natural rocks (e.g., calcite, marble, pumice, sepiolite and dolomite); synthetic particles of inorganic and organic flours; and / or particles of organic material (e.g., sawdust, coconut shells, corn cobs and tobacco stalks).

[0185] Suitable emulsifiers and foam formers include, for example, nonionic emulsifiers and anionic emulsifiers (eg, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates and aryl sulfonates) and protein hydrolysates.

[0186] Suitable dispersants include, for example, lignin sulfite waste liquors and methylcellulose. Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in powder, granular or lattice form, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids, can be used in the disclosed compositions. Other additives can include, for example, mineral oils and vegetable oils.

[0187] Colorants such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts may also be included in the composition.

[0188] Methods for preparing solid and liquid compositions for agrochemicals are generally known and can be used according to the present disclosure (wherein such methods involve adding one or more ascaroside salts to such compositions). In some embodiments, the composition according to the present disclosure can be in the form of a granular material (including dust, pellets, soluble powders, flowable powders, water-dispersible granules, etc.). In some embodiments, the composition according to the present disclosure can be in liquid form (e.g., solutions, suspensions, concentrates, or emulsions). In some embodiments, the composition is in the form of a granular material treated with a modified ascaroside salt-containing liquid. In some embodiments, the composition comprising ascaroside salts is formed into fibers or filaments, and in some such embodiments, woven or nonwoven textiles (e.g., films) can be produced from fibers or filaments. In some embodiments, the composition is made into particles as provided herein. In some embodiments, the composition is in the form of a film as provided herein, for example, a plastic mulch. Any of the solid compositions provided herein can be optionally coated by methods well known in the art to delay the release of ascaroside salts. See, for example, the methods and compositions for modified release disclosed in PCT / US2023 / 20472, filed April 28, 2023, which is incorporated herein by reference.

[0189] It is expected that the compounds (including salts), compositions and methods of the present application will encompass variations and modifications developed using the information of the embodiments described in this disclosure. The methods and processes described in this specification may be adapted or modified by one of ordinary skill in the relevant art.

[0190] It is understood that the use of titles in this disclosure is for the convenience of the reader. The presence and / or placement of titles is not intended to limit the scope of the subject matter described herein. Unless otherwise indicated, an embodiment located in a certain section of an application may be applied to other embodiments throughout the application, either alone or in combination.

[0191] Throughout the specification, when compositions, compounds or products are described as having, including or comprising specific components, or when processes and methods are described as having, including or comprising specific steps, it is also contemplated that there are articles, devices and systems of the present application that essentially consist of or consist of the components, and that there are processes and methods according to the present application that essentially consist of or consist of the processing steps.

[0192] Example

[0193] In order to more fully understand the present application, the following examples are listed. It should be understood that these examples are only for illustrative purposes and should not be considered as limiting in any way.

[0194] Various salts of the ascaroside ascr#18 were produced and tested for their ability to protect plants from pathogens.

[0195] Salt preparation:

[0196] To 2.5 mL of 1 mM ascr#18 in water was added an equal volume of 0.5 mM zinc acetate in water. The mixture was stirred for 1 h and then evaporated in vacuo to give (ascr#18)2Zn as a white solid.

[0197] To 2.5 mL of 1 mM ascr#18 in water was added an equal volume of 1 mM potassium hydroxide in water. The mixture was stirred for 1 h and then evaporated in vacuo to afford (ascr#18)K as a white solid.

[0198] To 2.5 mL of degassed 1 mM ascr#18 solution was added an equal volume of degassed 0.5 mM iron(II) acetate. The mixture was stirred under nitrogen for 1 h and then evaporated in vacuo to give (ascr#18)2Fe as a yellow-orange solid which was stored under nitrogen until use.

[0199] To 2.5 mL of 1 mM ascr#18 solution was added an equal volume of 0.5 mM nickel(II) acetate trihydrate. The mixture was stirred for 1 h and then evaporated in vacuo to give (ascr#18)2Ni as a green solid.

[0200] To 2.5 mL of 1 mM ascr#18 solution was added an equal volume of 0.5 mM manganese(II) acetate tetrahydrate. The mixture was stirred for 1 h and then evaporated in vacuo to afford (ascr#18)2Mn as a brown solid.

[0201] Salt Testing

[0202] The efficacy of the zinc salt of ascr#18 was compared to that of free ascr#18 in a greenhouse plant pathogen assay. Two-week-old wheat plants were sprayed with a solution containing 1 μM ascr#18 or 1 μM of the zinc salt (ascr#18) 2Zn. Twenty-four hours after treatment, the plants were inoculated with spores of Helicoverpa spp., the causative agent of root rot and brown spot blight. Ten days after inoculation, disease symptoms were quantified by measuring the symptomatic area on leaves. Figure 1 As shown, zinc salt was able to better protect against pathogens than unmodified ascr#18 (data are mean ± SEM (n≥13). *P≤0.04; two-tailed t-test).

[0203] It should be understood that the order of steps or the order in which certain actions are performed is not important as long as the method is still feasible. In addition, two or more steps or actions can be performed simultaneously.

[0204] All publications and patent applications mentioned in the specification are indicative of the levels of those skilled in the art to which the invention pertains. All publications and patent applications are incorporated herein by reference to the same extent as if each individual publication or patent application was specifically and individually indicated to be incorporated by reference.

[0205] Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, it will be apparent that certain changes and modifications may be practiced within the scope of the appended claims.

Claims

1. A compound of the formula [A-(C(O)O) - ] p M P+ of salt, wherein: A is the ascaroside moiety; M is a metal or ammonium cation; and p is an integer from 1 to 3, And wherein, when p is 2 or 3, each A may be the same or different.

2. The salt of claim 1, wherein p is 1.

3. The salt of claim 1, wherein p is 2.

4. The salt of claim 1, wherein p is 3.

5. The salt of any one of claims 1 to 4, wherein M is a metal.

6. The salt of claim 5, wherein the metal is selected from the group consisting of potassium (K), calcium (Ca), magnesium (Mg), zinc (Zn), manganese (Mn), iron (Fe), copper (Cu), molybdenum (Mo) and nickel (Ni).

7. The salt of claim 6, wherein the metal is selected from the group consisting of copper (Cu), zinc (Zn), manganese (Mn) and iron (Fe).

8. The salt of any one of claims 1 to 4, wherein M is an ammonium cation or an analog thereof.

9. A salt comprising at least one boron atom coordinated to an ascaroside (A).

10. The salt of any one of claims 1 to 9, wherein A has structure (I) in: Z is an optionally substituted C 2-40 an aliphatic group, and R a and R b Each of the following is independently -H, or an optionally substituted moiety selected from the group consisting of: C 1-20 Aliphatic group, C 1-20 Acyl, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus-linked functional group, sulfur-linked functional group, silicon-linked functional group, C 2-20 Carbonate (e.g. part -C(O)OR c ), C 2-20 Carbamate (e.g., moiety -C(O)N(R c )2) C 2-20 Thioesters (e.g., moieties -C(S)R c ), C 2-20 Thiocarbonates (e.g., moieties -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., part-C(S)SR c ), C 1-20 Thiocarbamates (e.g., moieties -C(S)N(R c ) 2), a sugar moiety, a peptide, a polymer chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, wherein R c is independently selected at each occurrence from -H, optionally substituted C 1-12 aliphatic, optionally substituted C 1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, and wherein R a and R b Can be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

11. The salt of claim 10, wherein Z is selected from the group consisting of: i.-CH(CH3)-R 1 , where R 1 is an optionally substituted C 1-40 aliphatic groups; ii.-CH(CH3)-(CH2) n -CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; iii.-CH(CH3)-(CH2) n -CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; iv.-CH(CH3)-(CH2) n -CH(OH)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; v.-CH(CH3)-(CH2) n -C(O)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; vi.-(CH2) n -CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; vii.-(CH2) n -CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; viii.-(CH2) n -CH(OH)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; and ix.-(CH2) n -C(O)-CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

12. The salt of claim 10 or claim 11, wherein R a and R b Each is -H.

13. The salt of any one of claims 10 to 12, wherein Z is -CH(CH3)-(CH2) n -CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

14. The salt of any one of claims 1 to 13, wherein A is ascr#18.

15. A salt of the formula: wherein M is a metal or ammonium cation; and p is an integer from 1 to 3.

16. A composition comprising the salt of any one of claims 1 to 15.

17. The composition of claim 16 which is in solid form.

18. The composition of claim 17, wherein the solid form comprises a powder or granules.

19. The composition of claim 16, which is in liquid form.

20. The composition of claim 19, wherein the liquid form is a sprayable formulation.

21. The composition of any one of claims 16 to 20, further comprising one or more additional components selected from the group consisting of: surfactants, including emulsifiers, dispersants, foam formers, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, ultraviolet radiation absorbers, weathering stabilizers, plasticizers, release agents, fragrances, thermal insulation additives (e.g., silica), cross-linking agents, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, extenders / stickers, tackifiers, plant penetrants, safeners, spreaders, and wetting agents.

22. A method for enhancing the physical properties of ascarosides and providing one or more nutrients to a plant, comprising: The plant or part thereof or the soil surrounding the plant or part thereof is contacted with a salt as claimed in any one of claims 1 to 15 or a composition as claimed in any one of claims 16 to 21.

23. The method of claim 22, wherein the part thereof is selected from the group consisting of roots, stems, leaves, seeds and flowers.

24. A method as claimed in claim 22 or claim 23, wherein the plant is a vegetable or fruit plant.

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