Modified release of ascarosides

Abstract

The present application relates to modified release compounds and compositions comprising one or more ascarosides that can be applied to plants to provide increased disease resistance. Certain compounds are structurally modified ascarosides, for example in the form of ascaroside-containing polymers. Certain compounds are physically modified ascarosides in the form of one or more ascarosides formulated with organic and / or inorganic components. Ascarosides are biodegradable and have been shown to break down rapidly in soil and be metabolized by other organisms, including plants.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Patent Application No. 63 / 336,738, entitled "Modified Release of Ascarosides," filed April 29, 2022, which is incorporated herein by reference.

[0002] FIELD OF THE DISCLOSURE This application relates generally to pesticidal compounds, compositions and methods of treating plants to promote resistance to pathogens. [Background technology]

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

[0004] Ascaroside treatments, when applied to plants, have been shown to increase plant resistance to certain pathogens by inducing or priming one or more plant defense responses that can inhibit pathogen growth and / or infestation. Ascarosides can activate and / or prime the plant's innate defenses, thereby preventing pathogen growth and / or protecting the crop from the harmful effects of the pathogen.

[0005] The application of pesticides to plants and the surrounding soil generally suffers from various drawbacks such as runoff / drift, etc. It would be useful to provide compositions and methods that can provide modified release of these compounds to plants during growth. Summary of the Invention

[0006] The present disclosure provides compositions and methods for modified release of ascarosides. In some embodiments, such modified release is achieved by making structural changes to the ascaroside molecule. In other embodiments, such modified release is provided by a composition-based approach, which may or may not result in structural changes to the ascaroside(s) contained within the formulation. The present disclosure further provides methods for extending the period during which ascaroside-based treatments can affect modulation of disease resistance in plants.

[0007] Ascarosides have been shown to be biodegradable, breaking down rapidly in soil and being metabolized by other organisms, including plants. This poses a challenge to some commercial applications of ascarosides. For example, in agricultural settings, it may be desirable to apply ascarosides as seed treatments or provide them via in-furrow applications when crops are planted, and in pharmaceutical applications, it may be desirable to develop time-release or implantable devices that release ascarosides over time. In the case of use on plants, the inventors have observed that such applications are not always reliable, and hypothesize that this is because the ascaroside molecules degrade before they can be taken up by the crop plant. For example, if seeds coated with seed treatments containing unmodified ascarosides take more than a week to germinate, there is a risk that much of the ascaroside in the coating will biodegrade while in contact with the soil before the plant leaves the seed. This may result in the intended ascaroside-based response in the germinating plant not being achieved or being attenuated. To address this problem, the present invention provides ascaroside compositions that are less susceptible to rapid biodegradation and / or are designed to release the ascaroside over an extended period of time, which delay or extended release increases the opportunity for crop plants to absorb or respond to the ascaroside, improving the reliability and / or convenience of applying such products.

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

[0009] Embodiment 1: A structurally modified ascaroside selected from the group consisting of: a) an ascaroside-based oligomer or polymer comprising two or more ascaroside moieties, optionally comprising a linker moiety between adjacent ascaroside moieties; b) an oligomeric or polymeric functionalized ascaroside comprising an ascaroside moiety, having one, two, or three oligomers or polymers attached to said ascaroside moiety; and c) an ascaroside pendant polymer comprising a polymer, having one or more pendant ascaroside moieties attached to said polymer, optionally comprising a linker moiety between said polymer and said pendant ascaroside moiety.

[0010] Embodiment 2: The structurally modified ascaroside of embodiment 1, wherein said modified ascaroside is an ascaroside-based oligomer or polymer, said oligomer or polymer comprising two or more ascaroside moieties having no linker moieties between said adjacent ascaroside moieties.

[0011] Embodiment 3: The structurally modified ascaroside of embodiment 1 or 2, wherein the modified ascaroside is an ascaroside-based oligomer or polymer, and the adjacent ascaroside moieties are linked to each other via ester bonds formed from a hydroxyl group on a first ascaroside molecule and a carboxylic acid on a second ascaroside molecule.

[0012] Embodiment 4: The structurally modified ascaroside of embodiment 1, wherein the modified ascaroside is an ascaroside-based oligomer or polymer, said oligomer or polymer comprising two or more ascaroside moieties having a linker moiety between said adjacent ascaroside moieties.

[0013] Embodiment 5: The structurally modified ascaroside of embodiment 1, wherein said linker moiety is selected from the group consisting of ether, ester, amide, glycoside, urethane, carbonate, and siloxane moieties.

[0014] Embodiment 6: The structurally modified ascaroside of any of embodiments 1-5, wherein the modified ascaroside is an ascaroside-based oligomer or polymer, the oligomer or polymer comprising between 2 and 1000 ascaroside moieties.

[0015] Embodiment 7: The structurally modified ascaroside of embodiment 6, wherein the oligomer or polymer comprises between 2 and 500 ascaroside moieties.

[0016] Embodiment 8: The structurally modified ascaroside of embodiment 6, wherein the oligomer or polymer comprises between 2 and 100 ascaroside moieties.

[0017] Embodiment 9: The structurally modified ascaroside of embodiment 6, wherein said oligomer or polymer comprises 2 to 10 ascaroside moieties.

[0018] Embodiment 10: The structurally modified ascaroside of embodiment 6, wherein said oligomer or polymer comprises at least 10 ascaroside moieties.

[0019] Embodiment 11: The structurally modified ascaroside of embodiment 6, wherein said oligomer or polymer comprises at least 20 ascaroside moieties.

[0020] Embodiment 12: The structurally modified ascaroside of embodiment 6, wherein said oligomer or polymer comprises at least 50 ascaroside moieties.

[0021] Embodiment 13: The structurally modified ascaroside of embodiment 1, wherein said modified ascaroside is an oligomer- or polymer-functionalized ascaroside, said oligomer- or polymer-functionalized ascaroside comprising one oligomer or polymer attached to said ascaroside.

[0022] Embodiment 14: The structurally modified ascaroside of embodiment 1, wherein said modified ascaroside is an oligomeric or polymeric functionalized ascaroside, said oligomeric or polymeric functionalized ascaroside comprising two oligomers or polymers attached to said ascaroside.

[0023] Embodiment 15: The structurally modified ascaroside of embodiment 1, wherein said modified ascaroside is an oligomer- or polymer-functionalized ascaroside, said oligomer- or polymer-functionalized ascaroside comprising three oligomers or polymers attached to said ascaroside.

[0024] Embodiment 16: The structurally modified ascaroside of embodiment 1, wherein said modified ascaroside is an ascaroside pendant polymer, said ascaroside pendant polymer comprising from about 5 to about 500 pendant ascaroside moieties attached to said ascaroside pendant polymer.

[0025] Embodiment 17: The structurally modified ascaroside of embodiment 1 or 16, wherein said modified ascaroside is an ascaroside pendant polymer, and said one or more pendant ascaroside moieties are directly attached to said polymer.

[0026] Embodiment 18: The structurally modified ascaroside of embodiment 1 or 16, wherein said modified ascaroside is an ascaroside pendant polymer, said ascaroside pendant polymer comprising a linker moiety between said polymer and said one or more pendant ascaroside moieties.

[0027] Embodiment 19: The structurally modified ascaroside of embodiment 18, wherein said linker moiety is selected from the group consisting of ether, ester, amide, glycoside, urethane, carbonate, and siloxane moieties.

[0028] Embodiment 20: The structurally modified ascaroside of any of embodiments 13-19, wherein the oligomer or polymer comprises a biodegradable polymer.

[0029] Embodiment 21: The structurally modified ascaroside of any of embodiments 13-20, wherein the oligomer or polymer is selected from the group consisting of chitosan, chitin, starch, lignin, agar, pectin, cellulose, other polysaccharides (e.g., bark, sawdust, other cellulosic wastes), poly(ethylene glycol), poly(caprolactone), poly(lactide), poly(glycolic acid), polybutylene, poly(vinyl alcohol), poly(vinyl chloride), poly(citric acid), poly(acrylate), poly(aspartic acid), poly(ethylene), polyethylene vinyl acetate (PEVA), polystyrene, divinylbenzene, and derivatives and copolymers thereof.

[0030] Embodiment 22: The ascaroside moiety has the structure (I): [ka] During the ceremony, Z is an optionally substituted C 3-40 is an aliphatic group, R a and R b each independently is -H or C 1-20 aliphatic, C 1-20 Achill, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-bonded functional groups, sulfur-bonded functional groups, silicon-bonded functional groups, C 2-20 Carbonates (e.g., the moiety -C(O)OR c ), C 2-20 Carbamates (e.g., the moiety -C(O)N(R c )2) C 2-20Thioesters (e.g., the moiety -C(S)R c ), C 2-20 Thiocarbonates (e.g., the moiety -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., the moiety -C(S)SR c ), C 1-20 Thiocarbamates (e.g., the moiety -C(S)N(R c 2) an optionally substituted moiety selected from the group consisting of a sugar moiety, a peptide, a polymer chain, or a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule; c is independently in each occurrence -H, optionally substituted C 1-12 Aliphatic, optionally substituted C 1-12 R is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a bond or linkage to another ascaroside molecule via a carbon-containing linker moiety; a and R b may be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, optionally containing one or more sites of unsaturation. Embodiment 23: Z is i.-CH(CH3)-R 1 (R 1 is an optionally substituted C 1-40 aliphatic groups), ii. -CH(CH3)-(CH2) n -CO2R 2 (n is an integer from 1 to 40, 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; iii. -CH(CH3)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 is -H, a metal cation, an optionally substituted C 1-20an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iv. -CH(CH3)-(CH2) n -CH(OH)-CH-COR 2 (n is an integer from 1 to 40, 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; v.-CH(CH3)-(CH2) n -C(O)-CH-COR 2 (n is an integer from 1 to 40, 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; vi.-(CH2) n -CO2R 2 (n is an integer from 1 to 40, 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; vii.-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, 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; viii.-(CH2) n -CH(OH)-CH-COR 2 (n is an integer from 1 to 40, 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; ix.-(CH2) n -C(O)-CH-COR 2(n is an integer from 1 to 40, 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; x.-CH(CH3)-(CH2) n -CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xi. -CH(CH3)-(CH2) n -CH=CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xii. -CH(CH3)-(CH2) n -CH(OH)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xiii. -CH(CH3)-(CH2) n -C(O)-CH-CON(R 3) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xiv.-(CH2) n -CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xv.-(CH2) n -CH=CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xvi.-(CH2) n -CH(OH)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linker moiety to another ascaroside molecule; or xvii.-(CH2) n -C(O)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 23. The structurally modified ascaroside of embodiment 22, wherein the ascaroside is selected from the group consisting of a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond or a linker moiety to another ascaroside molecule.

[0031] Embodiment 24: R a and R b and R are each -H.

[0032] Embodiment 25: Z is -CH(CH3)-(CH2) n -CO2R 2 n is an integer from 1 to 40; R 2 is -H, a metal cation, an optionally substituted C 1-20 25. The structurally modified ascaroside of any of embodiments 22-24, which is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0033] Embodiment 26: The structurally modified ascaroside of any of embodiments 1 to 25, wherein at least one of the ascaroside moieties is ascr#18.

[0034] Embodiment 27: Physically modified ascarosides comprising one or more ascarosides compounded with organic or inorganic materials.

[0035] Embodiment 28: The physically modified ascaroside of embodiment 27, wherein said ascaroside is blended with an organic material selected from coir, peat, and / or pine bark.

[0036] Embodiment 29: The physically modified ascaroside of embodiment 27, wherein said ascaroside is formulated with a polymer resin.

[0037] Embodiment 30: The physically modified ascaroside of embodiment 29, wherein said polymeric resin is a biodegradable polymer.

[0038] Embodiment 31: The physically modified ascaroside of embodiment 29 or 30, wherein said polymer resin is a melt-processable polymer.

[0039] Embodiment 32: The physically modified ascaroside of any of embodiments 29-31, wherein the polymer resin is selected from the group consisting of polypropylene, polyethylene, poly(vinyl chloride), polystyrene, polyethylene terephthalate, polyethylene-vinyl acetate, polyurethane, acrylonitrile butadiene styrene (ABS), nylon, vegetable starch, polylactic acid (PLA), polyhydroxyalkanoates (PHAs), and derivatives and copolymers of any two or more thereof.

[0040] Embodiment 33: The physically modified ascaroside of embodiment 27, wherein the ascaroside is compounded with an inorganic material selected from the group consisting of perlite, vermiculite, sand, clay, talc, wood flour, peat, silica gel, mica, activated carbon, and combinations thereof.

[0041] Embodiment 34: The physically modified ascaroside of embodiment 27, wherein the ascaroside is combined with an inorganic material selected from a fertilizer (e.g., ammonium phosphate, ammonium sulfate, urea, muriate of potash, superphosphate), a herbicide (e.g., sodium chlorate or sodium sulfate), an insoluble silica-type material (e.g., sand or crushed walnut hulls), an argillaceous material (e.g., montmorillonite, kaolinite, or other types of clay), diatomaceous earth, granulated corn cob, soapstone, quartz, lead, iron, and agricultural minerals (e.g., sulfur, gypsum, lime, calcium carbonate, etc.), and combinations thereof.

[0042] Embodiment 35: The physically modified ascaroside of any one of embodiments 27-34, comprising one or more bonds between one or more of the ascarosides and the organic material or the inorganic material.

[0043] Embodiment 36: The physically modified ascaroside of any one of embodiments 27 to 36, 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, UV absorbers, weathering stabilizers, plasticizers, release agents, fragrances, thermal additives (e.g., silica), crosslinkers, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, bulking / adhesives, tackifiers, plant penetrating agents, toxicity mitigants, spreading agents, and wetting agents.

[0044] Embodiment 37: At least one of the ascarosides has the structure (I): [ka] During the ceremony, Z is an optionally substituted C 3-40 is an aliphatic group, R a and R b each independently is -H or C 1-20 aliphatic, C 1-20 Achill, C 1-20Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-bonded functional groups, sulfur-bonded functional groups, silicon-bonded functional groups, C 2-20 Carbonates (e.g., the moiety -C(O)OR c ), C 2-20 Carbamates (e.g., the moiety -C(O)N(R c )2) C 2-20 Thioesters (e.g., the moiety -C(S)R c ), C 2-20 Thiocarbonates (e.g., the moiety -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., the moiety -C(S)SR c ), C 1-20 Thiocarbamates (e.g., the moiety -C(S)N(R c 2) an optionally substituted moiety selected from the group consisting of a sugar moiety, a peptide, a polymer chain, or a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule; c is independently in each occurrence -H, optionally substituted C 1-12 Aliphatic, optionally substituted C 1-12 R is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a bond or linkage to another ascaroside molecule via a carbon-containing linker moiety; a and R b may be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, optionally containing one or more sites of unsaturation.

[0045] Embodiment 38: Z is i.-CH(CH3)-R 1 (R 1 is an optionally substituted C 1-40 aliphatic groups), ii. -CH(CH3)-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 is -H, a metal cation, an optionally substituted C1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iii. -CH(CH3)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, 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; iv. -CH(CH3)-(CH2) n -CH(OH)-CH-COR 2 (n is an integer from 1 to 40, 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; v.-CH(CH3)-(CH2) n -C(O)-CH-COR 2 (n is an integer from 1 to 40, 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; vi.-(CH2) n -CO2R 2 (n is an integer from 1 to 40, 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; vii.-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, 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; viii.-(CH2) n-CH(OH)-CH-COR 2 (n is an integer from 1 to 40, 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; ix.-(CH2) n -C(O)-CH-COR 2 (n is an integer from 1 to 40, 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; x.-CH(CH3)-(CH2) n -CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xi. -CH(CH3)-(CH2) n -CH=CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xii. -CH(CH3)-(CH2) n -CH(OH)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xiii. -CH(CH3)-(CH2) n -C(O)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xiv.-(CH2) n -CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xv.-(CH2) n -CH=CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; xvi.-(CH2) n -CH(OH)-CH-CON(R 3) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linker moiety to another ascaroside molecule; or xvii.-(CH2) n -C(O)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 38. The physically modified ascaroside of embodiment 37, wherein the ascaroside is selected from the group consisting of a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule.

[0046] Embodiment 39: R a and R b The physically modified ascaroside of embodiment 37 or 38, wherein each is -H.

[0047] Embodiment 40: Z is -CH(CH3)-(CH2) n -CO2R 2 n is an integer from 1 to 40; R 2 is -H, a metal cation, an optionally substituted C 1-20 The physically modified ascaroside of any one of embodiments 37-39, which is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0048] Embodiment 41: The physically modified ascaroside of any one of embodiments 27 to 40, wherein at least one of the ascaroside moieties is ascr#18.

[0049] Embodiment 42: A composition comprising a structurally modified ascaroside of any one of embodiments 1-26 and / or a physically modified ascaroside of any one of embodiments 27-41, and one or more agriculturally acceptable excipients or additives.

[0050] Embodiment 43: The composition of embodiment 42, in liquid form.

[0051] Embodiment 44: The composition of embodiment 43, wherein the liquid is a sprayable formulation.

[0052] Embodiment 45: The composition of embodiment 42, in solid form.

[0053] Embodiment 46: The composition of embodiment 45, wherein the solid comprises a granule.

[0054] Embodiment 47: The composition of embodiment 45, wherein the solid comprises plastic mulch.

[0055] Embodiment 48: The composition of embodiment 45, wherein the solid composition is a film.

[0056] Embodiment 49: A method comprising contacting a plant or part thereof, or soil surrounding said plant or part thereof, with a structurally modified ascaroside of any of embodiments 1-26, a physically modified ascaroside of any of embodiments 27-41, or a composition of any of embodiments 42-48, wherein said ascaroside or said composition is effective for increasing the resistance of a plant to one or more pathogens and / or for inducing an immune response in said plant or part thereof.

[0057] Embodiment 50: The method of embodiment 49, wherein the part thereof is selected from the group consisting of roots, stems, leaves, seeds, and flowers.

[0058] Embodiment 51: The method of embodiment 49 or 50, wherein the plant is a vegetable or fruit plant.

[0059] These and other features, aspects, and advantages of the present disclosure will become apparent from reading the following detailed description in conjunction with the accompanying drawings, which are briefly described below. The present invention includes any combination of two, three, four, or more of the above-described embodiments, as well as any combination of two, three, four, or more of the features or elements described in the present disclosure, regardless of whether such features or elements are explicitly combined in a particular embodiment herein. The present disclosure is intended to be read in its entirety such that it should be considered as intended that any separable features or elements of the disclosed invention can be combined in any of its various aspects and embodiments, unless the context clearly indicates otherwise. Other aspects and advantages of the present disclosure will become apparent from the following.

[0060] definition In order that this disclosure may be more readily understood, certain terms are first defined below. Further definitions of these terms, as well as other terms, are found throughout the specification.

[0061] In this application, unless otherwise clear from the context, the term "a" may be understood to mean "at least one." As used in this application, the term "or" may be understood to mean "and / or." As used in this application, the terms "comprising" and "including" may be understood to encompass the itemized recited components or steps, whether presented by themselves alone or together with one or more additional components or steps. As used in this application, the term "comprise," as well as variations of this term, such as "comprising" and "comprises," are not intended to exclude other additives, components, integers, or steps.

[0062] About, Approximately: 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 for standard deviation as understood by those of ordinary skill in the art. When ranges are provided herein, the endpoints are included. Any numbers used in this application, with or without about / approximately, are meant to cover any normal variation that would be understood by a person of ordinary skill in the relevant art. In some embodiments, the term "about" or "approximately" refers to a range of values ​​that falls within 25%, 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, or less in either direction (greater or less) of the stated standard reference value, unless otherwise specified or clear from the context (except where such number exceeds 100% of possible values).

[0063] Definitions of certain functional groups and chemical terms are described in more detail below. For purposes of the present invention, chemical elements are defined as defined in The Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75 th Ed., inside cover, and specific functional groups are generally defined as described therein. In addition, general principles of organic chemistry, as well as specific functional moieties and reactivities, are described in Organic Chemistry, Thomas Sorrell, University Science Books, Sausalito, 1999, Smith and March March's Advanced Organic Chemistry, 5 thEdition, John Wiley & Sons, Inc., New York, 2001, Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989, Carruthers, Some Modern Methods of Organic Synthesis, 3 rd Edition, Cambridge University Press, Cambridge, 1987, the entire contents of each of which are incorporated herein by reference.

[0064] Certain compounds provided herein may contain one or more asymmetric centers and therefore may exist in various stereoisomeric forms, for example, enantiomers and / or diastereomers.Thus, the compounds of the present invention and their compositions may be in the form of individual enantiomers, diastereomers or geometric isomers, or may be in the form of a mixture of stereoisomers.In certain embodiments, the compounds described herein are enantiopure compounds.In certain other embodiments, mixtures of enantiomers or diastereomers are provided.

[0065] Additionally, certain compounds described herein may have one or more double bonds that can exist as either Z or E isomers, unless otherwise indicated. The compounds may be provided as individual isomers substantially free of other isomers, and alternatively, as mixtures of various isomers, e.g., racemic mixtures of enantiomers.

[0066] 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 isomers, diastereomers, (d)-isomers, (l)-isomers, racemic mixtures thereof, and other mixtures thereof, as they fall within the scope of this disclosure. For example, in some embodiments, a compound may be provided substantially free of one or more corresponding stereoisomers, and may be referred to as "stereochemically enriched."

[0067] When a particular enantiomer is preferred, in some embodiments it may be provided substantially free of the opposite enantiomer, and may be referred to as "optically enriched." As used herein, "optically enriched" means that the compound of the present invention is made up of a significantly higher proportion of one enantiomer. In certain embodiments, the compound is made up of at least about 90% by weight of one enantiomer. In some embodiments, the compound is made up of at least about 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8% or 99.9% by weight of one enantiomer. In some embodiments, the enantiomeric excess of the compound provided is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8% or 99.9%. In some embodiments, enantiomers can be separated from racemic mixtures by any known method, such as chiral high performance liquid chromatography (HPLC) and the formation and crystallization of chiral salts, or can be prepared by asymmetric synthesis.See, for example, Jacques, et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981); Wilen, SH, et al., Tetrahedron 33:2725 (1977); Eliel, ELStereochemistry of Carbon Compounds (McGraw-Hill, NY, 1962); Wilen, SHTables of Resolving Agents and Optical Resolutions p.268 (EL Eliel, Ed., Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0068] As used herein, the terms "halo" and "halogen" refer to an atom selected from fluorine (fluoro, -F), chlorine (chloro, -Cl), bromine (bromo, -Br), and iodine (iodo, -I).

[0069] As used herein, the terms "aliphatic" or "aliphatic group" refer to a hydrocarbon moiety that may be linear (i.e., unbranched), branched, or cyclic (including fused, bridged, and spiro-fused polycyclic), may be fully saturated or may contain one or more units of unsaturation, but is not aromatic. Unless otherwise specified, an aliphatic group contains 1-30 carbon atoms. In certain embodiments, an aliphatic group contains 1-12 carbon atoms. In certain embodiments, an aliphatic group contains 1-8 carbon atoms. In certain embodiments, an aliphatic group contains 1-6 carbon atoms. In some embodiments, an aliphatic group contains 1-5 carbon atoms, in some embodiments, an aliphatic group contains 1-4 carbon atoms, in still other embodiments, an aliphatic group contains 1-3 carbon atoms, and in still other embodiments, an aliphatic group contains 1-2 carbon atoms. Suitable aliphatic groups include, but are not limited to, linear or branched alkyl, alkenyl, and alkynyl, as well as hybrids thereof, such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl.

[0070] As used herein, the terms "heteroaliphatic" or "heteroaliphatic group" refer to an aliphatic group in which one or more carbon or hydrogen atoms are replaced by a heteroatom (e.g., oxygen, nitrogen, sulfur, phosphorus, boron, etc.).

[0071] As used herein, the term "unsaturated" means that a moiety has one or more double or triple bonds.

[0072] As used herein, the term "alkyl" refers to a saturated, straight or branched chain hydrocarbon radical derived from an aliphatic moiety containing 1-6 carbon atoms by removing one hydrogen atom. Unless otherwise specified, an alkyl group contains 1-12 carbon atoms. In certain embodiments, an alkyl group contains 1-8 carbon atoms. In certain embodiments, an alkyl group contains 1-6 carbon atoms. In some embodiments, an alkyl group contains 1-5 carbon atoms, in some embodiments, an alkyl group contains 1-4 carbon atoms, in still other embodiments, an alkyl group contains 1-3 carbon atoms, and in still other embodiments, an alkyl group contains 1-2 carbon atoms. Examples of alkyl radicals include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, sec-pentyl, iso-pentyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, n-decyl, n-undecyl, dodecyl, and the like.

[0073] As used herein, the term "alkenyl" refers to a monovalent group derived from a straight or branched chain aliphatic moiety having at least one carbon-carbon double bond by the removal of one hydrogen atom. Unless otherwise specified, an alkenyl group contains 2-12 carbon atoms. In certain embodiments, an alkenyl group contains 2-8 carbon atoms. In certain embodiments, an alkenyl group contains 2-6 carbon atoms. In some embodiments, an alkenyl group contains 2-5 carbon atoms, in some embodiments, an alkenyl group contains 2-4 carbon atoms, in still other embodiments, an alkenyl group contains 2-3 carbon atoms, and in still other embodiments, an alkenyl group contains 2 carbon atoms. Alkenyl groups include, for example, ethenyl, propenyl, butenyl, 1-methyl-2-buten-1-yl, and the like.

[0074] The term "aryl," used alone or as part of a larger moiety, such as "aralkyl," "aralkoxy," or "aryloxyalkyl," refers to monocyclic and polycyclic ring systems having a total of 5-20 ring members, in which at least one ring in the system is aromatic, and in which each ring in the system contains 3-12 ring members. The term "aryl" may be used interchangeably with the term "aryl ring." In certain embodiments, "aryl" refers to aromatic ring systems, including, but not limited to, phenyl, biphenyl, naphthyl, anthracyl, and the like, which may bear one or more substituents. Also, as used herein, 「 Also included within the scope of the term "aryl" are groups in which an aromatic ring is fused to one or more additional rings, such as benzofuranyl, indanyl, phthalimidyl, naphthoimidyl, phenanthridinyl, or tetrahydronaphthyl.

[0075] As described herein, the compounds provided herein may contain "optionally substituted" moieties. In general, the term "substituted", whether preceded by the term "optionally" or not, means that one or more hydrogens of the specified moiety are replaced with a suitable substituent. Unless otherwise specified, an "optionally substituted" group may have a suitable substituent at each substitutable position of the group, and when two or more positions in any given structure may be substituted with two or more substituents selected from a specified group, the substituents may be the same or different at each and every position. The combinations of substituents envisioned are preferably those that result in the formation of stable or chemically feasible compounds. As used herein, the term "stable" refers to compounds that are substantially unchanged when subjected to conditions that allow for their preparation, detection, and, in certain embodiments, their recovery, purification, and use for one or more of the purposes disclosed herein.

[0076] Suitable monovalent substituents on a substitutable carbon atom of an "optionally substituted" group are independently halogen, -(CH) 0-4 R°, -(CH2) 0-4OR°, -O-(CH2) 0-4 C(O)OR°, -(CH2) 0-4 CH(OR°)2, -(CH2) 0-4 SR°, R° may be substituted -(CH2) 0-4 Ph, R° may be substituted -(CH2) 0-4 O(CH2) 0-1 Ph, R° may be substituted with -CH=CHPh, -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) 0-4S(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)ON(R°)2, or -(C 1-4 linear or branched alkylene)C(O)ON(R°), 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, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or, notwithstanding the above definition, two independent occurrences of R° may be taken together with their intervening atom(s) to 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.

[0077] Suitable monovalent substituents on R° (or the ring formed by two independent occurrences of R° together with their intervening atoms) are independently halogen, -(CH2), 0-2 R λ , -(Halo R λ ), -(CH2) 0-2 OH, -(CH2) 0-2 OR λ , -(CH2) 0-2 CH(OR λ )2, -O(HaloR λ ), -CN, -N3, -(CH2) 0-2 C(O)R λ , -(CH2) 0-2 C(O)OH, -(CH2) 0-2 C(O)OR λ , -(CH2) 0-4 C(O)N(R°)2, -(CH2) 0-2 S.R. λ , -(CH2) 0-2 SH, -(CH2) 0-2 NH2, -(CH2) 0-2 NHRλ , -(CH2) 0-2 NR λ 2, -NO2, -SiR λ 3. -OSiR λ 3. -C(O)SR λ 、 -(C 1-4 Linear or branched alkylene)C(O)OR λ , or -SSR λ And each R λ is unsubstituted or, if preceded by "halo", is substituted only with one or more halogens, and 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. Suitable divalent substituents on a saturated carbon atom of R° include =O and =S.

[0078] 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- is mentioned, R * Each independent occurrence of 1-6 Aliphatic or unsubstituted 5-6 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents attached to the proximal substitutable carbon of an "optionally substituted" group include -O(CR * 2) 2-3 O- and R * Each independent occurrence of 1-6It is selected from aliphatic or unsubstituted 5-6 membered saturated, partially unsaturated, or aryl rings having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0079] R * Suitable substituents on the aliphatic group include halogen, -R λ , -(Halo R λ ), -OH, -OR λ , -O(HaloR λ ), -CN, -C(O)OH, -C(O)OR λ , -NH2, -NHR λ , -NR λ 2, or -NO2, where each R λ is unsubstituted or, if preceded by "halo", is substituted only with one or more halogens, and 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.

[0080] Suitable substituents on a substitutable nitrogen of an "optionally substituted" group include -R † , -NR † 2. -C(O)R † , -C(O)OR † , -C(O)C(O)R † , -C(O)CH2C(O)R † , -S(O)2R † , -S(O)NR † 2. -C(S)NR † 2. -C(NH)NR † 2, or -N(R † )S(O)2R † Each R † are independently hydrogen, C which may be substituted as defined below 1~6 an 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 above definitions, R †two independent occurrences of together with their intervening atom(s) form an unsubstituted 3-12 membered saturated, partially unsaturated, or aryl monocyclic or bicyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0081] R † Suitable substituents on the aliphatic groups are independently halogen, -R λ , -(Halo R λ ), -OH, -OR λ , -O(HaloR λ ), -CN, -C(O)OH, -C(O)OR λ , -NH2, -NHR λ , -NR λ 2, or -NO2, and each R λ is unsubstituted or, if preceded by "halo", is substituted only with one or more halogens, and 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.

[0082] As used herein, the term "substantially" refers to the qualitative condition of exhibiting the entire or nearly the entire extent or degree of a characteristic or property of interest.

[0083] It is a convention to name ascarosides with a few letter prefix followed by a pound sign (#) and a number (e.g., ascr#18). This convention is used in the scientific literature, and one of skill in the art will understand that each such name is associated with a specific chemical structure of a known composition and will immediately understand the structure of a molecule depicted using this nomenclature. Unless otherwise indicated, all compound identifiers of this format used herein conform to the definitions set forth in the C. elegans Small Molecule Identifier Database (SMID-DB), maintained at http: / / www.smid-db.org.

[0084] The term "pathogen" refers to any bacterium, fungus, oomecyte, virus, nematode (e.g., cyst or root-knot nematodes) or insect that has a pathogenic effect on plants.

[0085] In the drawings, features are not necessarily drawn to scale, with emphasis instead generally placed upon illustrating principles of the disclosed compositions and methods and not intended as limitations. For purposes of clarity, not all components may be labeled in the drawings. In the following description, various embodiments are described with reference to the following drawings: [Brief description of the drawings]

[0086] [Figure 1A] FIG. 2 is a non-limiting depiction of examples of ascaroside oligomers according to certain embodiments of the present disclosure. [Figure 1B] FIG. 2 is a non-limiting depiction of examples of ascaroside oligomers according to certain embodiments of the present disclosure. [Figure 1C] FIG. 2 is a non-limiting depiction of examples of ascaroside oligomers according to certain embodiments of the present disclosure. [Figure 1D] FIG. 2 is a non-limiting depiction of examples of ascaroside oligomers according to certain embodiments of the present disclosure.

[0087] [Diagram 2] FIG. 1 is a non-limiting representation of oligomeric or polymeric modified ascarosides containing ester linkages between adjacent ascaroside moieties.

[0088] [Figure 3A] FIG. 1 is a non-limiting diagram of examples of dimeric ascarosides with no linker between them. [Figure 3B] FIG. 1 is a non-limiting diagram of examples of dimeric ascarosides with no linker between them.

[0089] [Figure 4A] 1A-1D are non-limiting representations of ascaroside moieties containing 1, 2, and 3 polymer arms, respectively. [Figure 4B] 1A-1D are non-limiting representations of ascaroside moieties containing 1, 2, and 3 polymer arms, respectively. [Figure 4C] 1A-1D are non-limiting representations of ascaroside moieties containing 1, 2, and 3 polymer arms, respectively.

[0090] [Diagram 5] FIG. 1 is a non-limiting illustration of polymers containing pendant ascaroside moieties. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0091] Compounds, compositions, and methods for timed release of ascarosides are provided. The present disclosure is directed to delivering an ascaroside or derivative thereof via a modified release profile. The modified release profile may be, for example, extended, delayed, and / or controlled release, and may be useful for maintaining an effective concentration of the ascaroside or derivative thereof over an extended period of time. Some such modified release profiles may be provided via modifications to the structure of the ascaroside (or derivative thereof) such that the desired ascaroside molecule or derivative thereof is released from the modified composition over time and / or upon specific environmental exposure / trigger. Some such modified release profiles may be provided via a composition-based approach such that the desired ascaroside molecule or derivative thereof is released upon degradation of the composition in which it is contained.

[0092] Ascarosides are secondary metabolites produced by nematodes. A large number of structurally diverse ascarosides have been identified in nature, and the molecules are thought to function as an evolutionarily conserved chemical language that nematodes use to control many aspects of their development. Ascarosides are also perceived by other organisms and have been shown to have a variety of effects on a number of organisms, including bacteria, fungi, plants, and mammals, including humans.

[0093] Ascarosides are derivatives of the sugar ascarylose, a dideoxy sugar lacking hydroxyl groups at positions 3 and 6. Ascarosides have the formula I: [ka] and having the general structure shown in the formula: Z is an optionally substituted C 2-40 is an aliphatic group, R a and R b each independently is -H or C 1-20 aliphatic, C 1-20 Achill, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting groups, phosphorus-bonded functional groups, sulfur-bonded functional groups, silicon-bonded functional groups, C 2-20 Carbonates (e.g., the moiety -C(O)OR c ), C 2-20 Carbamates (e.g., the moiety -C(O)N(R c )2) C 2-20 Thioesters (e.g., the moiety -C(S)R c ), C 2-20 Thiocarbonates (e.g., the moiety -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., the moiety -C(S)SR c ), C 1-20 Thiocarbamates (e.g., the moiety -C(S)N(R c 2) an optionally substituted moiety selected from the group consisting of a sugar moiety, a peptide, a polymer chain, or a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule; c is independently in each occurrence -H, optionally substituted C 1-12 Aliphatic, optionally substituted C 1-12 R is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a bond or linkage to another ascaroside molecule via a carbon-containing linker moiety; a and R bmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

[0094] In certain embodiments, Z is (i) -CH(CH3)-R 1 (R 1 is an optionally substituted C 1-40 aliphatic groups), (ii) -CH(CH3)-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, 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 a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule; (iii) -CH(CH3)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, 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 a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule; (iv) -CH(CH3)-(CH2) n -CH(OH)-CH-COR 32 (n is an integer from 1 to 40, R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule; (v) -CH(CH3)-(CH2) n -C(O)-CH-COR 2 (n is an integer from 1 to 40, R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, 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 a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule; (vi)-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, 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 a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule; (vii)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, 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 a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule; (viii)-(CH2) n -CH(OH)-CH-COR 2 (n is an integer from 1 to 40, R 2is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, 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 another ascaroside molecule, or linked via a carbon-containing linker moiety; (ix)-(CH2) n -C(O)-CH-COR 2 (n is an integer from 1 to 40, R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, 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 a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule. In certain embodiments, Z is (x)-CH(CH3)-(CH2) n -CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; (xi) -CH(CH3)-(CH2) n -CH=CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; (xii) -CH(CH3)-(CH2) n -CH(OH)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; (xiii) -CH(CH3)-(CH2) n -C(O)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; (xiv)-(CH2) n -CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; (xv)-(CH2) n -CH=CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linkage via a carbon-containing linker moiety to another ascaroside molecule; (xvi)-(CH2) n -CH(OH)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or a linker moiety to another ascaroside molecule; or (xvii)-(CH2) n -C(O)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, 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 a bond or linkage via a carbon-containing linker moiety to another ascaroside molecule. In certain embodiments, R a is -H. In certain embodiments, R b is -H. In certain embodiments, a and R b are the same. In certain embodiments, R a and R b are both -H. In certain embodiments, R a and R b In certain embodiments, R a is -H, R b is other than -H. In certain embodiments, R a is other than -H, and Rb is -H. In certain embodiments, R a is -H, R b is p-hydroxybenzoate. In certain embodiments, R a is -H, R b is indole-3-carboxylate. In certain embodiments, R a is -H, R b is (E)-2-methyl-2-butenoate. In certain embodiments, R a , is -H, R b is a picolinate. In certain embodiments, R a is -H, R b is nicotinate. In certain embodiments, R a is -H, R b is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, R a is -H, R b is 4-((4-hydroxyphenylethyl)amino)-4-oxobutanoate. In certain embodiments, R a and R b are both -H and Z is selected from the formulas defined in (i) to (ix) above. a and b are both -H and Z conforms to formula (i) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (ii) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (iii) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (iv) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (v) above. In certain embodiments, R a and R bare both -H and Z conforms to formula (vi) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (vii) above. a and R b are both -H and Z conforms to formula (viii) above. a and R b are both -H and Z conforms to formula (ix) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (x) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xi) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xii) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xiii) above. a and R b are both -H and Z conforms to formula (xiv) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xv) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xvi) above. In certain embodiments, R a and R b are both -H and Z is in accordance with formula (xvii) above. 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). In certain embodiments, R 2 is an optionally substituted C 1-20In 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 methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-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 comprises a nucleotide. In certain embodiments, at least one R 3 is -H. In certain embodiments, both R 3 In certain embodiments, at least one R 3 is an optionally substituted C 1-20 In certain embodiments, both R 3 The groups may be the same or different, optionally substituted C 1-20 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 3 is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. 3is -CHCHOH. In certain embodiments, at least one R 3 is -CH2CH2OR 2 R 2 is 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 In certain embodiments, at least one R 3 comprises a nucleotide. In certain embodiments, the ascaroside is [ka] wherein x is an integer from 1 to 22; a , R b , and R 2 Each of the above is as defined in the genus and subgenera herein. In certain embodiments, the ascaroside is [ka] wherein x, R a , and R b Each of the above is as defined in the genus and subgenera herein. In certain embodiments, the ascaroside is [ka] wherein y is an integer from 1 to 20; a , R b , and R 2 Each of the above is as defined in the genus and subgenera herein. In certain embodiments, the ascaroside is [ka] wherein y, R a , and R b Each of the above is as defined in the genus and subgenera herein. In certain embodiments, the ascaroside is [ka] wherein x is an integer from 1 to 22; 2 are as defined by genus and subgenera above and herein. In certain embodiments, the ascaroside is [ka] where x is as defined above and in the genus and subgenus herein. In certain embodiments, the ascaroside is [ka] wherein y is an integer from 1 to 20; 2 are as defined by genus and subgenera above and herein. In certain embodiments, the ascaroside is [ka] where y is as defined above and in the genus and subgenus herein. In certain embodiments, the ascaroside is [ka] wherein x is an integer from 1 to 22; a , R b , and R 3 Each of the above is as defined in the genus and subgenera herein. In certain embodiments, the ascaroside is [ka] wherein x and R 3 Each of the above is as defined above and in the genus and subgenera herein. In certain embodiments, the ascaroside is [ka] wherein y is an integer from 1 to 20; a , R b , and R 2 Each of the above is as defined in the genus and subgenera herein. In certain embodiments, the ascaroside is [ka] wherein y and R 3 Each of the above is as defined above and in the genus and subgenera herein.

[0095] In certain embodiments, x in any of the structures herein is an integer from 2 to 18, inclusive. In certain embodiments, x in any of the structures herein is an integer from 4 to 10, inclusive. In certain embodiments, x in any of the structures herein is an integer from 6 to 12, inclusive. In certain embodiments, x in any of the structures herein is an integer from 5 to 9, inclusive. In certain embodiments, x in any of the structures herein is 7, 8, or 9. In certain embodiments, x in any of the structures herein is 6. In certain embodiments, x in any of the structures herein is 7. In certain embodiments, x in any of the structures herein is 8. In certain embodiments, x in any of the structures herein is 9. In certain embodiments, x in any of the structures herein is 10. In certain embodiments, x in any of the structures herein is 11. In certain embodiments, x in any of the structures herein is 12.

[0096] In certain embodiments, x in any of the structures herein is an integer greater than 5. In certain embodiments, x in any of the structures herein is an integer greater than 6, greater than 7, greater than 9, or greater than 10. In certain embodiments, x in any of the structures herein is an integer between 10 and 20.

[0097] In certain embodiments, the modified ascarosides provided may comprise a mixture of ascarosides that vary only in the value of x (i.e., the modified ascaroside comprises a mixture of congeners having various side chain lengths). In certain embodiments, such modified ascarosides are characterized in that the average value of x in the modified ascarosides is from about 2 to about 20. In certain embodiments, such modified ascarosides are characterized in that the average value of x in the composition is from about 3 to about 10, from about 4 to about 12, from about 6 to about 10, or from about 7 to about 9. In certain embodiments, such modified ascarosides are characterized in that the average value of x is greater than about 4, greater than about 5, greater than about 6, greater than about 7, or greater than about 8. The average value of x in such modified ascarosides is 1 This can be determined by a variety of methods well known in the art, including, but not limited to, analyzing the mixture by 1 H NMR spectroscopy, mass spectrometry, high performance liquid chromatography, and the like.

[0098] In certain embodiments, y in any of the structures herein is an integer from 2 to 18, inclusive. In certain embodiments, y in any of the structures herein is an integer from 4 to 10, inclusive. In certain embodiments, y in any of the structures herein is an integer from 6 to 12, inclusive. In certain embodiments, y in any of the structures herein is an integer from 5 to 9, inclusive. In certain embodiments, y in any of the structures herein is 7, 8, or 9. In certain embodiments, y in any of the structures herein is 6. In certain embodiments, y in any of the structures herein is 7. In certain embodiments, y in any of the structures herein is 8. In certain embodiments, y in any of the structures herein is 9. In certain embodiments, y in any of the structures herein is 10. In certain embodiments, y in any of the structures herein is 11. In certain embodiments, y in any of the structures herein is 12.

[0099] In certain embodiments, y in any of the structures herein is an integer greater than 5. In certain embodiments, y in any of the structures herein is an integer greater than 6, greater than 7, greater than 9, or greater than 10. In certain embodiments, y in any of the structures herein is an integer between 10 and 20.

[0100] In certain embodiments, the modified ascarosides provided may comprise a mixture of ascarosides that vary only in the value of y (i.e., the modified ascaroside comprises a mixture of congeners having various side chain lengths). In certain embodiments, such modified ascarosides are characterized in that the average value of y in the composition is from about 2 to about 20. In certain embodiments, such modified ascarosides are characterized in that the average value of y in the composition is from about 3 to about 10, from about 4 to about 12, from about 6 to about 10, or from about 7 to about 9. In certain embodiments, such modified ascarosides are characterized in that the average value of y is greater than about 4, greater than about 5, greater than about 6, greater than about 7, or greater than about 8. The average value of y in such modified ascarosides is 1 This can be determined by a variety of methods well known in the art, including, but not limited to, analyzing the mixture by 1 H NMR spectroscopy, mass spectrometry, high performance liquid chromatography, and the like.

[0101] In one embodiment, the ascarosides useful in the present invention have the general structure (I), where Z is -CH(CH)-(CH). n -CO2R 2 where n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0102] In one embodiment, the ascarosides useful in the present invention have the general structure (I), where Z is -CH(CH)-(CH). n -CH=CH-CO2R 2where n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0103] Particular ascarosides useful in the present invention include, but are not limited to, ascr#7 and ascr#18. [ka]

[0104] In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of ascr#9, ascr#12, ascr#14, ascr#1, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, ascr#24, ascr#26, ascr#28, ascr#30, ascr#32, ascr#34, and ascr#36. In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of ascr#9, ascr#14, ascr#10, and ascr#18.

[0105] In certain embodiments, the ascaroside used in the provided 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 the provided 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 the provided methods is selected from the group consisting of bhas#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, 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.

[0106] In certain embodiments, the ascaroside used in the methods provided 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.

[0107] In certain embodiments, the ascaroside used in the provided 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.

[0108] In certain embodiments, the ascaroside used in the methods provided 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 thereof.

[0109] Ascarosides can be obtained from natural sources (e.g., nematodes) or they can be synthetically prepared. Ascarosides can be synthetically prepared, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascarylose. An exemplary method for preparing ascarosides includes providing 1-O-substituted rhamnose as a feedstock, forming a monosulfonate ester at the 3-OH group of the feedstock, and treating the monosulfonate ester with a hydride source to form 1-O-substituted ascarylose. In certain embodiments, the formation of the monosulfonate ester is carried out on a substrate that does not contain a hydroxyl protecting group at the 2- or 4-position of the rhamnose feedstock. In certain embodiments, such a method includes contacting the feedstock with a sulfonating agent (i.e., a sulfonyl halide, sulfonic anhydride, or similar reagent) in the presence of a Lewis acid. Specific details regarding the synthesis of 1-O-substituted ascarylose can be found in PCT Application No. PCT / IB2021 / 056981, which is incorporated herein by reference. Structurally Modified Ascarosides

[0110] As referenced above, in some embodiments of the present disclosure, ascaroside molecules are modified to provide compounds that result in modified release of the ascaroside molecule during use (e.g., when applied to a plant, an animal, or the environment surrounding the plant or animal). Some such structurally modified ascarosides include oligomers or polymers that are at least partially composed of ascarosides. In some embodiments, the structural modifications are generally such that the modifications are reversible, i.e., the structurally modified ascaroside may release one or more ascaroside molecules upon one or more environmental exposures / triggers or upon degradation.

[0111] In some embodiments, structurally modified ascarosides are ascaroside-based oligomers or polymers, which include oligomers (e.g., dimers, trimers, tetramers, etc.) or polymers (i.e., containing ascaroside-containing repeating units) of ascarosides. The oligomers or polymers can include two or more connected ascarosides of the same formula and / or can include two or more connected ascarosides of different formulas. In some embodiments, the ascaroside molecules are directly connected to each other via a covalent bond between functional groups already present on the ascaroside molecules. For example, in some embodiments, such structurally modified ascarosides may be formed by combining a carboxylic acid on the side chain of one ascaroside (e.g., present within certain embodiments as a component of the "Z" group in formula (I) above) with a hydroxyl functional group on another ascaroside molecule (e.g., present within certain embodiments as a component of the "Z" group in formula (I) above). a or R b is H, or the ascaroside may contain an ester bond that may be formed by condensation with a polyvalent linker that otherwise contains an OH substituent (e.g., the Z group of formula (I) contains an OH substituent). In some embodiments, the ascaroside molecules are indirectly connected to each other via a covalent bond between a polyvalent linker and a functional group present on the ascaroside molecule.

[0112] In some embodiments, such ascaroside-based oligomers or polymers include oligomers or polymers that consist essentially of ascaroside molecules (e.g., oligomers or polymers in which the ascaroside comprises the primary monomer that makes up the oligomer or polymer), while in other embodiments, such compositions include copolymers or cooligomers of ascaroside molecules with polyvalent linkers or other monomers.

[0113] In certain embodiments, provided ascaroside-based oligomers or polymers conform to the following formula (II): A-[(L) m -A] p or L-[A-(L) m ] p (Formula II), wherein each A is independently an ascaroside molecule, L is a polyvalent linker moiety covalently attached to A, m is 0 or 1, and p is an integer from 1 to 1000. In some embodiments, the oligomer or polymer comprises a covalent bond to a carboxylic acid functionality on A (e.g., via an ester or amide bond). In some embodiments, the oligomer or polymer comprises a covalent bond to a hydroxyl functionality on A (e.g., via an ether, ester, glycoside, urethane, carbonate, or siloxane bond). Thus, the composition of the optional polyvalent linker L can vary widely.

[0114] In certain embodiments, provided ascaroside-based oligomers or polymers conform to formula (III): [(L) m -A] p or [A-(L) m ] p (Formula III), wherein each A is independently an ascaroside molecule, L is a polyvalent linker moiety covalently attached to A, m is 0 or 1, and p is an integer from 1 to 1000. In some embodiments, the oligomer or polymer comprises a covalent bond to a carboxylic acid functionality on A (e.g., via an ester or amide bond). In some embodiments, the oligomer or polymer comprises a covalent bond to a hydroxyl functionality on A (e.g., via an ether, ester, glycoside, urethane, carbonate, or siloxane bond). Thus, the composition of the optional polyvalent linker L can vary widely.

[0115] Such ascaroside-based oligomers and polymers provided according to the present disclosure may be linear or branched. A specific, non-limiting example of an oligomer containing five linked ascaroside ("A") moieties is shown in FIG. 1A, where each of A1, A2, A3, A4, and A5, as well as all of the "L" groups, may be the same or different. Each "a" is an integer that is 0 or 1, i.e., each A may be directly linked to an adjacent A via a bond or may include a linker (L) between them. For modified ascarosides in the form of further oligomers and polymers, it will be understood that each bond between the ascaroside moieties may result in the formation of linear or branched sections of the respective oligomer or polymer, depending, for example, on the point of attachment between the ascaroside moiety and the adjacent ascaroside moiety, or between the ascaroside moiety and the L.

[0116] In some embodiments, such ascaroside-based oligomers or polymers may contain ester linkages between adjacent ascaroside moieties. Non-limiting representative structures of oligomeric or polymeric modified ascarosides containing such ester linkages are shown in FIG. 2, where A′ represents portions of the ascaroside molecule not explicitly represented in the figure (i.e., the tetrahydropyranyl ring and the OR a -, OR b-, and / or at least a portion (or all) of the OZ substituents), each A' may be the same or different, and p is an integer from 1 to 1000. Oligomers and polymers within the scope of the present disclosure may be linear (e.g., all A'-containing subunits are connected to at most two adjacent subunits) or branched (e.g., at least some A'-containing subunits are connected directly or via a linker to two or more adjacent A subunits). In some embodiments, except for the terminal A' subunits, each A' is connected to two other A' subunits via ester bonds. In some embodiments, except for the terminal A' subunits, at least some A' subunits are connected to three other A' subunits.

[0117] Chemical reactions that can be suitably used to generate oligomers and polymers from molecules containing hydroxyl groups and / or carboxylic acids are well known in the art and can be readily adapted to provide oligomers or polymers containing ascarosides. For example, catalysts, methods, and processing techniques that can be used are described in Textbook of Polymer Science, 3rd Edition by Fred W. Billmeyer (ISBN: 978-0-471-03196-3), which is incorporated herein by reference in its entirety. Depending on the targeted oligomer or polymer structure, it may be desirable to utilize ascaroside precursors that have one or more reactive functional groups masked with protecting groups. In this approach, covalent bonds can be formed at specific functional groups on the ascaroside molecule without the participation or interference of other functional groups. Once the desired oligomer or polymer is formed, such protecting groups can be removed. Suitable protecting groups and strategies for their formation and removal are described in Greene's Protective Groups in Organic Synthesis by Peter G.M.Wuts and Theodora W. Greene (ISBN:9780471697541), which is incorporated herein by reference in its entirety. In certain embodiments, ascaroside precursors having one or more of the hydroxyl groups on the ascarylose sugar protected are oligomerized via reaction of a carboxylic acid group (or a reactive derivative thereof) present on the ascaroside side chain. In certain embodiments, ascaroside precursors having protecting groups that mask the reactivity of the carboxylic acid group present on the ascaroside side chain are oligomerized via reaction of one or more hydroxyl groups present on the ascaroside sugar.

[0118] In certain embodiments, ascarylose oligomers or polymers are formed by first reacting ascarylose or a derivative thereof with a reagent that attaches a polymerizable group to the molecule, such as a polymerizable functional group, for example, an olefin, amine, isocyanate, epoxide, acyl halide, etc., for which known polymerization processes exist. Such polymerizable functional groups can be introduced by means well known in the art of synthetic organic chemistry. Methods for incorporating polymerizable functional groups onto ascarosides may require the use of protecting groups as described above to ensure that the group is attached at the desired position or that other functional groups present on the ascaroside do not interfere with the functional group attachment process or subsequent processes required to form the oligomer or polymer. Such polymerizable functional groups are preferably attached to the ascaroside substrate via a bond that is labile under biological or environmental conditions, such that free ascaroside molecules can be liberated when the resulting oligomer or polymer degrades.

[0119] In certain embodiments, the polyvalent linker "L" may comprise an oligomeric or polymeric group (e.g., L may be composed of a chain of repeating monomeric subunits). In certain embodiments, L comprises a polyester, polyamide, polyether, polycarbonate, or polyolefin. In certain embodiments, L comprises a biopolymer. In certain embodiments, L comprises a carbohydrate, a peptide, a protein, RNA, or DNA. In certain embodiments, L comprises a carbohydrate. In certain embodiments, L comprises a starch, cellulose, chitosan, or chitin. In certain embodiments, L comprises a peptide or protein. In certain embodiments, L comprises a polynucleotide.

[0120] Non-limiting examples of certain specific ascaroside dimers within the scope of this disclosure are provided in Figures 3A and 3B (where a=0, i.e., no "L" linker groups are present between the ascaroside moieties). One of skill in the art will recognize that each ascaroside has an OR on adjacent ascarosides. a OR bthrough its OZ group (condensed with a carboxyl moiety in an OZ substituent on an adjacent ascaroside) or through its OR group (esterified with a carboxyl moiety in an OZ substituent on an adjacent ascaroside) a OR b It will be appreciated that adjacent ascarosides may be connected via an R group. In certain embodiments, oligomers in which each ascaroside is connected in the same manner (e.g., the Z group on a first ascaroside is connected to the R group on a second ascaroside). a The Z group on the second ascaroside is esterified to an R group on the third ascaroside. a The Z group on the third ascaroside is esterified to the R group on the fourth ascaroside. a In other embodiments, oligomers are provided in which each ascaroside is randomly connected (e.g., a Z group on a first ascaroside is esterified with an R group on a second ascaroside). a The Z group on the second ascaroside is esterified to an R group on the third ascaroside. b group, and the R a The group is esterified to a Z group on a fourth ascaroside.

[0121] In some embodiments, the structurally modified ascarosides provided herein are oligomeric or polymeric functionalized ascarosides, which include ascarosides chemically bonded to natural or synthetic oligomers or polymers. For example, the Z, R on the ascaroside of formula (I) above. a , and R bAny one or more of may be functionalized with an oligomer or polymer. Three exemplary embodiments are shown in FIG. 4, where each of polymer 1, polymer 2, and polymer 3 may be the same or different in composition and / or length, and each of the reference polymers may be present or absent in different embodiments (e.g., the molecule may include only one polymer attached to the ascaroside, the molecule may include two polymers attached to different moieties on the ascaroside, or the molecule may include three polymers attached to different moieties on the ascaroside). The polymer(s) may be covalently attached to the ascaroside in a manner similar to that described above with respect to ascaroside-based oligomers or polymers. Specifically, considering the ascaroside structure of formula (I), the pendant polymer may be selected from the group consisting of Z, OR, and Zn, and may be selected from the group consisting of Zn, OR, and Zn. a OR b One, two, or all of the substituents can be incorporated to obtain a polymeric functionalized ascaroside. The polymer(s) on the polymeric functionalized ascaroside can be linear, branched, hyperbranched, bottle-brush, or dendritic. The polymer can contain a single repeating unit or can be a copolymer (e.g., block, random, graft, tapered, or alternating). The number / length of repeating units of the oligomer or polymer can vary. In some embodiments, the oligomer or polymer contains about 2 to about 1000 repeating units. The polymer can be natural or synthetic, or a hybrid thereof.

[0122] Suitable polymers include any agriculturally acceptable polymer that can be suitably functionalized to covalently attach to moieties present on the ascaroside molecule. In preferred embodiments, such polymers are biodegradable polymers. In some embodiments, such polymers are bio-based or natural polymers. In some embodiments, such polymers are synthetic polymers. Specific non-limiting examples of suitable polymers include chitosan, chitin, starch, lignin, agar, pectin, cellulose, other polysaccharides (e.g., bark, sawdust, other cellulosic wastes), poly(ethylene glycol), poly(caprolactone), poly(lactide), poly(glycolic acid), polybutylene, poly(vinyl alcohol), poly(vinyl chloride), poly(citric acid), poly(acrylates), poly(aspartic acid), poly(ethylene), poly(ethylene vinyl acetate), polyethylene vinyl acetate (PEVA), polystyrene, polydivinylbenzene, and derivatives and copolymers thereof.

[0123] Suitable polymers include pharma- ceutically acceptable polymers that may be suitably functionalized to covalently attach to moieties present on the ascaroside molecule. In preferred embodiments, such polymers are biocompatible and / or metabolically labile polymers.

[0124] In further embodiments, the structurally modified ascaroside is an ascaroside pendant polymer, where one or more ascarosides are attached directly or indirectly to the backbone of the polymer as pendant groups thereon, as shown, for example, in FIG. 5. Note that in FIG. 5, for simplicity, the polymer is shown as having five pendant ascaroside ("A") groups. However, it should be understood that the disclosure is not so limited. The number of pendant A groups on a given polymer chain can range, in some embodiments, for example, from 2 to about 1,000. The composition of the polymer can vary widely, and can be, for example, any of the agriculturally acceptable polymers referenced herein above. In certain embodiments, the composition includes a polymer, such as polyvinyl alcohol or polyvinyl acetate, having pendant hydroxy or acyloxy groups that can be esterified or transesterified with carboxyl groups of the ascaroside or modified ascaroside. In certain embodiments, the compositions include polymers such as polyvinyl alcohol, polyvinyl chloride, or polyvinyl acetate having pendant functional groups such as halide, alcohol, or acyloxy groups that can form ether bonds with hydroxyl groups on the ascaroside or ascaroside derivative, hi certain embodiments, the compositions include polymers such as polyacrylic acid or polyacrylates having pendant carboxy or carboxy ester groups that can be esterified or transesterified with hydroxyl groups on the ascaroside or modified ascaroside, or can form anhydride bonds with carboxyl groups on the ascaroside.

[0125] In some embodiments, the structurally modified ascarosides provided herein are oligomeric or polymeric functionalized ascarosides, including ascarosides bound to naturally occurring oligomers, polymers, or biomolecules, hi some embodiments, the structurally modified ascarosides include ascarosides covalently bound to starch, cellulose, lignin, or similar biopolymeric materials.

[0126] In some embodiments of the ascaroside pendant polymer, the pendant ascaroside molecule is attached to the polymer via a non-covalent bond, e.g., hydrogen bond and / or ionic bond. In some embodiments, the ascaroside molecule is covalently attached to the polymer directly or through various types of linkages, advantageously cleavable via an environmental trigger, such that under certain conditions the linkage is cleaved and the ascaroside or its derivative is released. Examples of non-covalent bonds include mixtures of polycationic polymers or oligomers with carboxylate anions of ascarosides, e.g., those derived from ascarosides having carboxylic acid moieties on the side chain, or ascarosides modified to provide such carboxylic acid groups (i.e., via reaction of the ascaroside hydroxyl group with a cyclic anhydride, such as succinic anhydride, maleic anhydride, or phthalic anhydride). Examples of suitable covalent bonds include, but are not limited to, ether, ester, amide, glycoside, urethane, carbonate, or siloxane bonds. Examples of particularly suitable covalent bonds include ester, amide, and glycoside bonds.

[0127] The release rate of the ascaroside moiety from such structurally modified ascarosides may, in some embodiments, depend on the respective polymer properties, such as the hydrophilic / hydrophobic ratio, linear / branched nature, length of the polymer, degree of crosslinking, extent of non-covalent interactions (e.g., hydrogen bonding and / or ionic interactions), and the nature of the type(s) of bond(s) within the structure. In some embodiments, the release profile depends at least in part on the nature of the bond(s) linking the ascaroside(s) to the remainder of the molecule, and in some embodiments, the ascaroside may be released by hydrolysis, thermodynamic dissociation, microbial degradation, or another chemical reaction that breaks the linkage(s) to the ascaroside. The release profile may be effectively tuned by modifying these properties. Physically Modified Ascarosides

[0128] In some embodiments, the release of the ascaroside is modified by physical methods, such as by incorporating the ascaroside within a matrix designed for its modified release. In some such embodiments, the release of the ascaroside from the matrix can be based on, for example, diffusion and / or matrix degradation. It should be noted that while such embodiments are referred to herein as including "physical" modifications, such modifications do not exclude the presence of structural modifications, i.e., some of the methods provided below may result in changes to the ascaroside such that the ascaroside structure may in fact be modified to some extent (e.g., by introducing (covalent or ionic) bonds to one or more other moieties).

[0129] In certain embodiments, physically modified ascarosides are provided by mixing or blending one or more ascarosides with polymeric materials ("organic formulations") and / or inorganic materials ("inorganic formulations"). In some embodiments, nanocomposites are provided that include ascarosides blended with both polymeric and inorganic materials.

[0130] In some embodiments, organically compounded ascarosides are provided. Organic compounding may include mixing and / or blending an organic component (e.g., a polymeric resin) with one or more additives (here, one or more ascarosides and, optionally, one or more additional components such as agriculturally acceptable excipients and additive types referenced herein below). In some embodiments, such embodiments may be described as formulations in which the ascaroside is impregnated within the organic component. Compounding in some embodiments may involve heating (e.g., such that the organic component (e.g., polymeric resin) is in molten form during mixing and / or blending). In some embodiments, compounding is performed during an extrusion process known in the art such that the resulting extrudate (which may be of various sizes and shapes) contains one or more ascarosides.

[0131] In some such embodiments, the combining involves the formation of a covalent bond between the organic (e.g., polymeric) material and at least one of the one or more ascarosides, while in other embodiments, substantially no covalent bond is formed between the organic (e.g., polymeric) material and the ascaroside(s).

[0132] In certain embodiments, the ascaroside compositions that are blended with the polymer include compositions that result from reactive extrusion of a polymer having one or more ascarosides. For example, such compositions may include compositions that result from reactive extrusion of a polyester (particularly a biodegradable polyester) with an ascaroside. Such reactive extrusion may result in partial or complete incorporation of the ascaroside into the polymer structure, for example, via the formation of covalent bonds (e.g., by condensation or transesterification) to one or more carboxylic acid or hydroxyl groups present on the ascaroside.

[0133] The types of organic components with which the ascarosides may be blended can vary widely. In some embodiments, the ascarosides are blended with materials such as coir, peat, and / or pine bark. In some embodiments, the ascarosides are blended with a polymeric resin, and in such embodiments, generally any melt-processable polymer can be used to provide the organically blended ascaroside. Certain such melt-processable polymers are biocompatible and / or biodegradable. Suitable polymers include, but are not limited to, the types of polymers mentioned herein above, as well as, for example, polypropylene, polyethylene, poly(vinyl chloride), polystyrene, polyethylene terephthalate, polyethylene-vinyl acetate, polyurethane, acrylonitrile butadiene styrene (ABS), nylon, vegetable starch, cellulose, methylcellulose, cellulose acetate, polylactic acid (PLA), polyhydroxyalkanoates (PHAs), and derivatives and copolymers of any two or more thereof.

[0134] In some embodiments, inorganically formulated ascarosides are provided. Inorganic formulation in this context may include mixing and / or blending of an inorganic component with one or more additives (here, one or more ascarosides and, optionally, one or more additional components such as agriculturally acceptable excipients and additive types referenced below). In some embodiments, such embodiments may be described as formulations, in which the ascarosides are impregnated, absorbed, or adsorbed within the inorganic component. Mixing may be performed in a variety of ways, may be performed at room or elevated temperatures, and may or may not include solvents or other adjuvants. The inorganic material may vary, and in some embodiments may include one or more of perlite, vermiculite, sand, clay, talc, wood flour, peat, silica gel, mica, activated carbon, and the like. In some embodiments, the inorganic materials can be fertilizers, e.g., herbicides such as ammonium phosphate, ammonium sulfate, urea, muriate of potash, superphosphates, sodium chlorate and sodium sulfate, insoluble silica-type materials such as sand, clayey materials such as crushed walnut hulls, montmorillonite, kaolinite, or other types of clay, diatomaceous earth, granulated corn cob, soapstone, quartz, and agricultural minerals such as sulfur, gypsum, lime, calcium carbonate, and any combination of two or more thereof.

[0135] In certain embodiments, the present invention provides formulated growth media containing any of the controlled release ascaroside compositions described herein. Examples include formulated soilless mixtures such as those commonly used in plant propagation and indoor horticulture (e.g., mixtures containing defined blends of materials such as peat moss, coconut fiber, vermiculite, perlite, etc.), as well as single component media such as perlite, vermiculite, etc. Providing such growth media pre-enriched with a composition that releases ascarosides over time provides growers with a simple and economical method to treat plants with ascarosides, for example, to protect such plants from pathogens. The ascaroside composition may be present in the growth medium, such as a granule specific for the purpose of releasing ascarosides, or may be incorporated as part of one of the typical components in the medium (e.g., the ascaroside composition may be combined with perlite or vermiculite in such a blend).

[0136] In some embodiments, two or more of the approaches provided herein can be combined. For example, the structurally modified ascarosides described above can be further physically modified by combining the structurally modified ascarosides with organic or inorganic materials.

[0137] Methods of Use and Compositions

[0138] The modified ascarosides described herein can be used to treat living plants, seeds, the soil surrounding the plants, or the soil into which the seeds / saplings are planted. In some embodiments, the modified ascarosides are applied to one or more parts of the plant, such as the roots, stems, leaves, seeds, and / or flowers. Such methods can be carried out at any one or more stages of the plant's life cycle, such as from the seed, seedling, growing plant, immediately before or immediately after harvest.

[0139] Although not the primary focus of the present invention, the inventors also recognize that the compositions and methods herein may have applications for the treatment of animals with ascarosides (including the treatment of humans with ascarosides as therapeutics or dietary supplements). Specifically, in certain embodiments, the present invention includes modified release formulations of ascr#7 (or a derivative or analog thereof) for use in treating or ameliorating health disorders in animals and humans.

[0140] Advantageously, methods using the disclosed modified ascarosides allow for altered release of the ascaroside (compared to methods using unmodified ascarosides), e.g., delayed and / or controlled and / or sustained release. "Delayed release" means that the ascaroside is not provided to the plant (or animal) immediately upon application of the compound or composition to the plant or animal or its environment (e.g., soil), but rather, the ascaroside is released at a later time after application (or upon specific environmental trigger(s) as referenced herein). "Controlled release" means that the ascaroside is released over time, e.g., mostly at a predetermined rate. "Sustained release" means that the ascaroside is released over a longer period of time after application to the plant, animal, or soil than is achieved by application of the corresponding unmodified ascaroside. In some embodiments, the disclosed modified ascarosides release one or more ascarosides substantially only in response to conditions related to an environmental trigger, e.g., light, temperature, soil pH, moisture, enzymatic changes, etc. The modified release provided by the modified ascarosides provided herein can, in some embodiments, allow less ascaroside to be used over the same period of activity than direct application of an unmodified ascaroside composition. In some embodiments, such controlled release can provide reduced leaching of the ascaroside, reduced evaporation, and reduced degradation (by light, hydrolysis, and / or microorganisms), any of which can remove or degrade the ascaroside before it can perform its desired function.

[0141] The disclosed treatment methods can, in some embodiments, protect growing plants in the manner described in U.S. Patent 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 in (or near) the plant to which the modified ascaroside is applied (thereby inhibiting pathogen growth and / or infestation). Pathogens against which the disclosed methods can promote resistance include, but are not limited to, oomycota, bacteria, nematodes, viruses, and insects, including, but not limited to, Pseudomonas syringae, Phytophthora infestans, Blumeria graminis, Heterodera schachtii, Meloidogyne incognita, Meloidogyne hapla, and turnip crinkle virus. In some embodiments, such modified release profiles are such that the modified ascarosides can be effective for a longer period of time than the corresponding treatment with (unmodified) ascarosides.

[0142] The disclosed treatment methods, in some embodiments, protect plants or plant-based products from contamination by pathogens or prevent or delay the onset of plant decay, or can be produced by the methods described in patent applications PCT / US22 / 81895 and PCT / US23 / 17947, each of which is incorporated herein by reference in its entirety.

[0143] The exact manner in which the plant, seed, or soil is treated with the modified ascaroside is not particularly limited. Treatment of the seed, plant, and / or soil according to the present disclosure may be performed, for example, by soaking, spraying, evaporation, misting, scattering, painting, lateral application, or in-furrow application. For example, in certain embodiments, the plant or soil may be sprayed with a suitable liquid composition, a solid plastic mulch composition containing ascarosides as described above may be applied to the soil around the plant, the plant may be grown or propagated in a medium (or a pot or container formed from a composition described herein) containing any of the modified compositions described herein, and / or a granular composition may be provided for in-furrow or lateral application.

[0144] The types of plants that can be treated according to the methods of the present disclosure are not particularly limited and can be, for example, fruit and vegetable plants, trees, and shrubs. Non-limiting examples of plants that can be treated according to the disclosed methods include, but are not limited to, plants selected from the group consisting of tobacco, Arabidopsis, tomato, barley, potato, sweet potato, yam, cotton, soybean, strawberry, sugarcane, sugar 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.

[0145] In the methods provided herein, the modified ascarosides may be applied directly to plants and / or soil or may be formulated into compositions that may be applied to plants and / or soil. Thus, the present disclosure generally provides compositions comprising at least one modified ascaroside (e.g., including structurally modified ascarosides and / or physically modified ascarosides) and one or more inert ingredients, such as one or more agriculturally acceptable carriers. Preferably, non-toxic carriers are used in the methods of the invention.

[0146] The term "agriculturally acceptable carrier" includes any carrier suitable for administration to plants or soil, such as solutions (e.g., directly sprayable or dilutable solutions), emulsions (e.g., emulsion concentrates and diluted emulsions), wettable powders, suspensions, soluble powders, powders, dusts, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, encapsulation in polymeric materials, coatable pastes, natural and synthetic materials impregnated with active compounds, and excipients conventional in the formulation art, such as those used to form microencapsulations in polymeric substances. These compositions may be prepared in a known manner, for example, by mixing the modified ascaroside(s) with one or more agriculturally acceptable carriers, such as liquid solvents or solid carriers, optionally using additional ingredients including, but not limited to, surfactants including emulsifiers, dispersants, foam formers, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, UV absorbers, weathering stabilizers, plasticizers, release agents, fragrances, thermal additives (e.g., silica), crosslinkers, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, extenders / adhesives, tackifiers, plant penetrants, toxic ameliorants, spreading agents, wetting agents, and the like.

[0147] In some embodiments, at least one modified ascaroside is the only active agent in the composition. In some embodiments, the composition includes one or more additional ascarosides (e.g., in another modified or unmodified form). In some embodiments, one or more other active agents are included in the composition (e.g., one or more pesticides, fertilizers, etc.). The modified ascaroside-containing compositions provided herein can be in a variety of forms, including solid and liquid forms.

[0148] When the agriculturally acceptable carrier is water, in some embodiments, an organic solvent can be incorporated as an auxiliary liquid solvent. Suitable liquid solvents include, for example, aromatic compounds (e.g., xylene, toluene and alkylnaphthalenes), chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons (e.g., chlorobenzene, chloroethylene and methylene chloride), aliphatic hydrocarbons (e.g., cyclohexane), paraffins (e.g., petroleum fractions, mineral and vegetable oils), alcohols (e.g., butanol or glycols and their ethers and esters), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone) and strongly polar solvents (e.g., dimethylformamide and dimethylsulfoxide).

[0149] Suitable solid agriculturally acceptable 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), ground and fractionated natural rocks (e.g., calcite, marble, pumice, sepiolite, and dolomite), synthetic granules of inorganic and organic meals, granules of organic materials (e.g., sawdust, coconut shells, corn cobs, and tobacco stalks).

[0150] Suitable emulsifiers and foam-forming agents include, for example, nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers, e.g., alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates and aryl sulfonates), protein hydrolysates.

[0151] Suitable dispersants include, for example, lignin-sulfite waste liquor and methylcellulose. Carboxymethylcellulose in the form of powder, granule or lattice, as well as natural and synthetic polymers, 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.

[0152] Inorganic pigments, e.g., colorants such as iron oxide, titanium oxide, Prussian blue, organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes, and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc may also be included in the composition.

[0153] Methods for preparing solid and liquid compositions for agricultural chemical use are generally known and may be used in accordance with the present disclosure, including incorporating one or more modified ascarosides within such compositions. As referenced above, compositions according to the present disclosure may in some embodiments be in the form of granular materials (including dusts, pellets, soluble powders, flowable powders, water-dispersible granules, etc.). In some embodiments, compositions according to the present disclosure may be in liquid form (e.g., solutions, suspensions, or emulsions). Some modified ascarosides may have limited solubility in water. Thus, in some embodiments, the ascaroside or modified ascaroside is dissolved in a water-miscible co-solvent (e.g., ethanol) to first dissolve the modified ascaroside. Then, in some embodiments, the dissolved modified ascaroside can be added to a suitable amount of water to obtain an aqueous modified ascaroside-containing composition. In some embodiments, the composition is in the form of a granular material that has been treated with a modified ascaroside-containing liquid. In some embodiments, compositions including modified ascarosides are formed into fibers or filaments, and in some such embodiments, woven or nonwoven fabrics (e.g., films) can be produced therefrom. In some embodiments, compositions provided herein are pelletized. In some embodiments, compositions provided herein are in the form of a film, e.g., plastic mulch. In some embodiments, compositions provided herein are in the form of a molded article, e.g., a pot, container, bag, or sleeve in which plants can be propagated or grown. Any of the solid compositions provided herein can be coated, if desired, via methods commonly known in the art, to further delay release of the modified ascarosides.

[0154] In some embodiments, methods of making compositions are provided in which an ascaroside is blended with a polymer (e.g., to form a film, fiber, pellet, molded or extruded article, or filament). Such blending generally involves heating or melting the polymer and blending the softened or molten polymer with the ascaroside. Such methods can produce a physical mixture of the ascaroside and polymer, or can produce a copolymer (e.g., by a process such as reactive extrusion) in which the ascaroside reacts with the polymer during the blending process (e.g., via transesterification or condensation).

[0155] The compounds, compositions, and methods of the present application are intended to encompass variations and adaptations developed using information from the embodiments described in this disclosure. Adaptations or modifications of the methods and processes described herein may be made by one of ordinary skill in the relevant art.

[0156] It will be understood that the use of headings in this disclosure is provided for the convenience of the reader. The presence and / or placement of headings is not intended to limit the scope of the subject matter described herein. Unless otherwise specified, embodiments located in one section of this application apply to other embodiments, both alone and in combination, throughout this application.

[0157] Throughout the description, when compositions, compounds, or articles of manufacture are described as having, containing, or comprising particular ingredients, or when processes and methods are described as having, containing, or comprising particular steps, it is further contemplated that there are articles, devices, and systems of the present application that consist essentially of, or consist of, the recited ingredients, and that there are processes and methods according to the present application that consist essentially of, or consist of, the recited process steps.

[0158] It should be understood that the order of steps or order for performing certain operations is immaterial so long as the method described remains operable. Moreover, two or more steps or operations may be performed simultaneously.

[0159] All publications and patent applications mentioned in this specification are indicative of the level of those skilled in the art to which this invention pertains. All publications and patent applications are herein incorporated by reference to the same extent as if each individual publication or patent application was specifically and individually indicated to be incorporated by reference.

[0160] 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 can be practiced within the scope of the appended claims.

Claims

1. A structurally modified ascaoside, a) an ascaloside-based oligomer or polymer comprising two or more ascaloside moieties, and optionally comprising a linker moiety between adjacent ascaloside moieties, b) Oligomer or polymer-functionalized ascalosides comprising an ascaloside moiety, wherein one, two, or three oligomers or polymers are bonded to the ascaloside moiety, and c) The structurally modified askaloside selected from the group consisting of askaloside pendant polymers, wherein the askaloside pendant polymer comprises a polymer, with one or more pendant askaloside portions bonded to the polymer, and optionally including a linker portion between the polymer and the pendant askaloside portions.

2. The structurally modified ascaloside is an ascaloside-based oligomer or polymer, wherein the ascaloside-based oligomer or polymer is of formula (II): A-[(L) m -A] p or L-[A-(L) m ] p (Formula II) It is, In the formula, each A is independently an ascaloside molecule. L is a multivalent linker portion covalently bonded to A, m is either 0 or 1. The structurally modified ascaloside according to claim 1, wherein p is an integer from 1 to 1000.

3. The structurally modified ascaloside is an ascaloside-based oligomer or polymer, wherein the ascaloside-based oligomer or polymer is of formula (III): [(L) m −A] p or [A−(L) m ] p (Formula III) It is, In the formula, each A is independently an ascaloside molecule. L is a multivalent linker portion covalently bonded to A, m is either 0 or 1. The structurally modified ascaloside according to claim 1, wherein p is an integer from 1 to 1000.

4. The structurally modified askaloside according to claim 1, wherein the modified askaloside is an askaloside-based oligomer or polymer, and the oligomer or polymer comprises two or more askaloside portions that do not have a linker portion between adjacent askaloside portions.

5. The structurally modified askaloside according to claim 4, wherein the adjacent askaloside portions are bonded to each other via ester bonds formed from a hydroxyl group on the first askaloside molecule and a carboxylic acid on the second askaloside molecule.

6. The structurally modified askaloside according to claim 1, wherein the modified askaloside is an askaloside-based oligomer or polymer, and the oligomer or polymer comprises two or more askaloside portions having a linker portion between adjacent askaloside portions.

7. The structurally modified ascaloside according to claim 6, wherein the linker portion is selected from the group consisting of ether, ester, amide, glycoside, urethane, carbonate, and siloxane portions.

8. The structurally modified ascaloside according to claim 1, wherein the modified ascaloside is an ascaloside-based oligomer or polymer, and the oligomer or polymer contains 2 to 1,000 ascaloside moieties.

9. The structurally modified ascaloside according to claim 8, wherein the oligomer or polymer comprises 2 to 500 ascaloside moieties.

10. The structurally modified ascaloside according to claim 8, wherein the oligomer or polymer comprises 2 to 100 ascaloside moieties.

11. The structurally modified ascaloside according to claim 8, wherein the oligomer or polymer comprises 2 to 10 ascaloside moieties.

12. The structurally modified ascaloside according to claim 1, wherein the oligomer or polymer comprises at least 10 ascaloside moieties.

13. The structurally modified ascaloside according to claim 12, wherein the oligomer or polymer comprises at least 20 ascaloside moieties.

14. The structurally modified ascaloside according to claim 12, wherein the oligomer or polymer comprises at least 50 ascaloside moieties.

15. The structurally modified ascaloside according to claim 1, wherein the structurally modified ascaloside is the oligomer or polymer-functionalized ascaloside, and the oligomer or polymer-functionalized ascaloside comprises one oligomer or polymer bonded to the ascaloside.

16. The structurally modified ascaloside according to claim 1, wherein the structurally modified ascaloside is the oligomer or polymer-functionalized ascaloside, and the oligomer or polymer-functionalized ascaloside comprises two oligomers or polymers bonded to the ascaloside.

17. The structurally modified ascaloside according to claim 1, wherein the structurally modified ascaloside is the oligomer or polymer-functionalized ascaloside, and the oligomer or polymer-functionalized ascaloside comprises three oligomers or polymers bonded to the ascaloside.

18. The structurally modified ascaloside according to claim 15, wherein the oligomer or polymer comprises a biodegradable polymer.

19. The structurally modified ascaloside according to claim 15, wherein the oligomer or polymer is selected from the group consisting of chitosan, chitin, starch, lignin, agar, pectin, cellulose, other polysaccharides (e.g., bark, sawdust, other cellulose waste), poly(ethylene glycol), poly(caprolactone), poly(lactide), poly(glycolic acid), polybutylene, poly(vinyl alcohol), poly(vinyl chloride), poly(citric acid), poly(acrylate), poly(aspartic acid), poly(ethylene), polyethylene vinyl acetate (PEVA), polystyrene, divinylbenzene, and derivatives and copolymers thereof.

20. The structurally modified askaloside according to claim 1, wherein the structurally modified askaloside is the askaloside pendant polymer, and the askaloside pendant polymer comprises about 5 to about 500 pendant askaloside portions bonded to the askaloside pendant polymer.

21. The structurally modified askaloside according to claim 1, wherein the structurally modified askaloside is the askaloside pendant polymer, and one or more pendant askaloside portions are directly bonded to the polymer.

22. The structurally modified askaloside according to claim 1, wherein the structurally modified askaloside is the askaloside pendant polymer, and the askaloside pendant polymer includes a linker portion between the polymer and one or more pendant askaloside portions.

23. The structurally modified ascaloside according to claim 22, wherein the linker portion is selected from the group consisting of ether, ester, amide, glycoside, urethane, carbonate, and siloxane portion.

24. The ascaoside portion has structure (I), 【Chemistry 17】 During the ceremony, Z is replaced by C as desired. ３－４０ It is an aliphatic group, R ａ and R ｂ each independently is -H, or C< １－２０ aliphatic, C １－２０ acyl, C １－２０ heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bonding functional group, sulfur bonding functional group, silicon bonding functional group, C ２－２０ carbonate (e.g., - moiety - C(O)OR ｃ ), C ２－２０ carbamate (e.g., - moiety - C(O)N(R ｃ )), C ２ ), C ２－２０ thioester (e.g., moiety - C(S)R ｃ ), C ２－２０ thiocarbonate (e.g., moiety - C(S)OR ｃ ), C ２－２０ dithiocarbonate (e.g., moiety - C(S)SR ｃ ), C １－２０ thiocarbamate (e.g., moiety - C(S)N(R ｃ )), C ２ ), a sugar moiety, a peptide, a polymer chain, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety, and is a optionally substituted moiety selected from the group consisting of R ｃ However, in each occurrence, independently, -H and C as desired are substituted. １－１２ Aliphatic, optionally substituted C １－１２ Selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain, or linkage to another ascaloside molecule via a carbon-containing linker moiety, R ａ and R ｂ The structurally modified askaloside according to claim 1, wherein together they can optionally form a substituted ring containing one or more heteroatoms and optionally one or more unsaturated moieties.

25. Z is (i) - CH(CH ３ )-R １ (R １ C is replaced as desired. １－４０ (It is an aliphatic group.) (ii) -CH(CH ３ )-(CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) (iii)-CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) (iv)-CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) (v)-CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) (vi)-(CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) (vii) - (CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) (viii)-(CH ２ ) ｎ -CH(OH)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules via carbon-containing linker moieties), and (ix) - (CH ２ ) ｎ -C(O)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ A structurally modified askaloside according to claim 24, selected from the group consisting of a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linkage to another askaloside molecule via a carbon-containing linker moiety.

26. Z is (x) - CH(CH ３ ) - (CH ２ ) ｎ - CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ is independently -H, an optionally substituted C １－２０ aliphatic group, an optionally substituted C １－２０ heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety). (xi)-CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) (xii)-CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) (xiii)-CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) (xiv)-(CH ２ ) ｎ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) (xv) - (CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) (xvi) - (CH ２ ) ｎ -CH(OH)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules via carbon-containing linker moieties), and (xvii)-(CH ２ ) ｎ -C(O)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ A structurally modified ascaloside according to claim 24, selected from the group consisting of a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.

27. R ａ and R ｂ The structurally modified ascaloside according to claim 24, wherein each of them is -H.

28. Z is -CH(CH ３ )-(CH ２ ) ｎ -CO ２ R ２ And n is an integer from 1 to 40, R ２ However, -H, metal cation, and optionally substituted C １－２０ A structurally modified ascaloside according to claim 24, which is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

29. The structurally modified askaloside according to claim 24, wherein at least one of the askaloside portions is ascr#18.

30. A physically modified ascaloside comprising one or more ascalosides compounded with organic or inorganic materials.

31. The physically modified ascaloside according to claim 30, wherein the ascaloside is compounded with an organic material selected from coir, peat, and / or pine bark.

32. The physically modified ascaloside according to claim 30, wherein the ascaloside is compounded with a polymer resin.

33. The physically modified ascaloside according to claim 32, wherein the polymer resin is a biodegradable polymer.

34. The physically modified ascaloside according to claim 32, wherein the polymer resin is a melt-processable polymer.

35. The physically modified ascaloside according to claim 32, wherein the polymer resin is selected from the group consisting of polypropylene, polyethylene, poly(vinyl chloride), polystyrene, polyethylene terephthalate, polyethylene-vinyl acetate, polyurethane, acrylonitrile butadiene styrene (ABS), nylon, vegetable starch, cellulose, methylcellulose, cellulose acetate, polylactic acid (PLA), polyhydroxyalkanoate (PHA), and their derivatives and any two or more copolymers.

36. The physically modified ascaloside according to claim 30, wherein the ascaloside is compounded with an inorganic material selected from the group consisting of perlite, vermiculite, sand, clay, talc, wood flour, peat, silica gel, mica, activated carbon, and combinations thereof.

37. The physically modified ascaloside according to claim 30, wherein the ascaloside is compounded with fertilizers (e.g., ammonium phosphate, ammonium sulfate, urea, potassium chloride (muria of potash), superphosphate), herbicides (e.g., sodium chlorate or sodium sulfate), insoluble silica-type materials (e.g., sand or crushed walnut husks), clayey materials (e.g., montmorillonite, kaolinite, or other types of clay), diatomaceous earth, granular corn cob, soapstone, quartz, lead, iron, and agricultural minerals (e.g., sulfur, gypsum, lime, calcium carbonate, etc.), and inorganic materials selected from combinations thereof.

38. A physically modified askaloside according to claim 30, comprising one or more bonds between one or more of the askalosides and the organic material or the inorganic material.

39. A physically modified ascaloside according to claim 30, further comprising one or more additional components selected from the group consisting of surfactants including emulsifiers, dispersants, foaming agents, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, UV absorbers, weather stabilizers, plasticizers, release agents, fragrances, heat retention additives (e.g., silica), crosslinking agents, antioxidants, defoaming agents, buffers, pH adjusters, compatibility agents, drift control additives, bulking agents / tackeners, tackifiers, plant penetration agents, toxicity mitigators, spreading agents, and wetting agents.

40. At least one of the askalosides has structure (I), [Chemistry 18] During the ceremony, Z is replaced by C as desired. ３－４０ It is an aliphatic group, R ａ and R ｂ Each of these independently corresponds to -H or C １－２０ aliphatic, C １－２０ Ashiru, C １－２０ Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bond functional group, sulfur bond functional group, silicon bond functional group, C ２－２０ Carbonates (e.g., partial-C(O)OR) ｃ ), C ２－２０ Carbamates (e.g., partial-C(O)N(R) ｃ ) ２ ), C ２－２０ Thioesters (e.g., partial-C(S)R) ｃ ), C ２－２０ Thiocarbonates (e.g., partial-C(S)OR) ｃ ), C ２－２０ Dithiocarbonates (e.g., partial-C(S)SR) ｃ ), C １－２０ Thiocarbamates (e.g., partial-C(S)N(R) ｃ ) ２ ), a optionally substituted portion selected from the group consisting of a sugar moiety, a peptide, a polymer chain, or linkage to another ascaloside molecule or linkage via a carbon-containing linker moiety, R ｃ However, in each occurrence, independently, -H and C as desired are substituted. １－１２ Aliphatic, optionally substituted C １－１２ Selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain, or linkage to another ascaloside molecule via a carbon-containing linker moiety, R ａ and R ｂ The physically modified askaloside according to claim 30, wherein together they can optionally form a substituted ring containing one or more heteroatoms and optionally one or more unsaturated moieties.

41. Z is i. -CH(CH ３ )-R １ (R １ C is replaced as desired. １－４０ (It is an aliphatic group.) ii. -CH(CH ３ )-(CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) iii. -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) iv. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) v. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) vi. - (CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) vii. - (CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) viiii. - (CH ２ ) ｎ -CH(OH)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules via carbon-containing linker moieties), and ix. - (CH ２ ) ｎ -C(O)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ A physically modified ascaloside according to claim 40, selected from the group consisting of a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.

42. Z is x. -CH(CH ３ )-(CH ２ ) ｎ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) xi. -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) xii. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) xiii. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) xiv. - (CH ２ ) ｎ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) xv. - (CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This may be a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.) xvi. - (CH ２ ) ｎ -CH(OH)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ (This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules via carbon-containing linker moieties), and xvii. - (CH ２ ) ｎ -C(O)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ A physically modified ascaloside according to claim 40, selected from the group consisting of a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.

43. R ａ and R ｂ The physically modified ascaloside according to claim 40, wherein each of them is -H.

44. Z is -CH(CH ３ )-(CH ２ ) ｎ -CO ２ R ２ And n is an integer from 1 to 40, R ２ However, -H, metal cation, and optionally substituted C １－２０ A physically modified ascaloside according to claim 40, which is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

45. The physically modified ascaloside according to claim 40, wherein at least one of the ascaloside moieties is ascr#18.

46. A composition comprising a structurally modified ascaloside according to any one of claims 1 to 29 and / or a physically modified ascaloside according to any one of claims 30 to 45, and one or more agriculturally acceptable excipients or additives.

47. The composition according to claim 46, which is in liquid form.

48. The composition according to claim 47, wherein the liquid is a sprayable formulation.

49. The composition according to claim 46, which is in solid form.

50. The composition according to claim 49, wherein the solid comprises granules.

51. The composition according to claim 49, wherein the solid comprises plastic mulch.

52. The composition according to claim 49, wherein the solid composition is a film.

53. It is a method, This includes bringing a plant or a part thereof, or the soil surrounding the plant or a part thereof, into contact with a structurally modified ascaoside as described in any one of claims 1 to 29. The method wherein the ascaloside is effective in increasing the resistance of a plant to one or more pathogens and / or in inducing an immune response in the plant or a part thereof.

54. The method according to claim 53, wherein the part is selected from the group consisting of roots, stems, leaves, seeds, and flowers.

55. The method according to claim 53, wherein the plant is a vegetable or fruit plant.

56. A method, This includes bringing a plant or a part thereof, or the soil surrounding the plant or a part thereof, into contact with a physically modified ascaoside as described in any one of claims 30 to 45. The method wherein the ascaloside is effective in increasing the resistance of a plant to one or more pathogens and / or in inducing an immune response in the plant or a part thereof.

57. A method, This includes bringing a plant or a part thereof, or the soil surrounding the plant or a part thereof, into contact with the composition described in claim 46. The method wherein the composition is effective in increasing a plant's resistance to one or more pathogens and / or in inducing an immune response in the plant or a part thereof.

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