Ascaroside combinations

Abstract

The present application relates to combinations of one or more ascarosides with one or more additional active agents (e.g., fungicides). Various combinations can provide enhanced crop protection, where certain combinations accidentally exhibit a synergistic effect. Various combinations may be accidentally co-formulated to provide a storage stable composition.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to U.S. Provisional Patent Application Serial No. 63 / 344,937, entitled “Ascaroside Combinations,” filed on May 23, 2022; U.S. Provisional Patent Application Serial No. 63 / 421,340, entitled “Ascarosides and Fungicidal Combinations and Methods for Use,” filed on November 1, 2022; U.S. Provisional Patent Application Serial No. 63 / 421,499, entitled “Ascarosides and Triazole Fungicidal Combinations and Methods for Use,” filed on November 1, 2022; and U.S. Provisional Patent Application Serial No. 63 / 486,018, entitled “Ascarosides and SDHI Fungicidal Combinations and Methods of Use,” filed on February 20, 2023, all of which are incorporated herein by reference in their entirety. Technical Field

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

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

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

[0006] Agrochemical treatments typically involve the application of more than one active agent to plants and the surrounding soil to effectively protect the plants from a variety of pathogens. It would be useful to provide additional combinations, compositions and methods that can provide protection for plants. Summary of the invention

[0007] The present disclosure provides compositions and methods, which involve applying one or more ascarosides in combination with one or more additional activating agents to plants. In some embodiments, the co-application of one or more ascarosides with one or more additional activating agents can provide a synergistic effect in terms of plant protection and / or yield. In some embodiments, the co-application of one or more ascarosides with one or more additional activating agents can include applying components within a single formulation (e.g., a liquid formulation). In some embodiments as described herein, such formulations can advantageously remain stable for a long time. This stability is unexpected because formulations comprising more than one activating agent are typically subject to the effects of instability (e.g., manifested as separation, sedimentation, a reduction in the content of the activating agent relative to the initial content, etc.).

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

[0009] Embodiment 1: A method of enhancing the activity of a fungicide comprising co-applying the fungicide and one or more ascarosides to a plant, plant part, or soil surrounding the plant or plant part.

[0010] Embodiment 2: The method of Embodiment 1, wherein the fungicide is a biofungicide.

[0011] Embodiment 3: The method of Embodiment 1, wherein the fungicide is a chemical fungicide.

[0012] Embodiment 4: The method of embodiment 3, wherein the chemical fungicide is selected from the group consisting of azoles, methoxyacrylates, carboxamides, nitrogen-containing heterocyclic compounds, carbamates and dithiocarbamates, guanidines, antibiotics, organometallic compounds, sulfur-containing heterocyclic compounds, organophosphorus compounds, organochlorine compounds, nitrophenyl derivatives, inorganic active compounds, and combinations thereof.

[0013] Embodiment 5: A method of enhancing the activity of a fungicide comprising co-applying the fungicide and one or more ascarosides to a plant, plant part, or soil surrounding the plant or plant part, wherein the fungicide comprises a triazole fungicide.

[0014] Embodiment 6: The method of Embodiment 5, wherein the triazole fungicide is prothioconazole or tebuconazole.

[0015] Embodiment 7: A method of enhancing the activity of a fungicide comprising co-applying the fungicide and one or more ascarosides to a plant, a plant part, or the soil surrounding the plant or plant part, wherein the fungicide comprises Q o 1. Fungicides.

[0016] Embodiment 8: A method as described in Embodiment 7, wherein the Q o I fungicide is strobilurin.

[0017] Embodiment 9: A method as described in Embodiment 8, wherein the methoxyacrylate is selected from the group consisting of: azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, enoxamyl, orysastrobin, fluoxastrobin, fenoxystrobin, tosoxim-methyl, pyraclostrobin, pyraclostrobin, pyraclostrobin, kresoxim-methyl, fenamidone or famoxadone.

[0018] Embodiment 10: The method of embodiment 9, wherein the strobilurin is azoxystrobin, picoxystrobin or trifloxystrobin.

[0019] Embodiment 11: The method of Embodiment 9, wherein the strobilurin is azoxystrobin.

[0020] Embodiment 12: A method as described in Embodiment 7, wherein the Q o I fungicide is fenamidone or famoxadone.

[0021] Embodiment 13: A method of enhancing the activity of a fungicide comprising co-applying the fungicide and one or more ascarosides to a plant, plant part, or soil surrounding the plant or plant part, wherein the fungicide comprises a SDHI fungicide.

[0022] Embodiment 14: The method of Embodiment 13, wherein the SDHI fungicide comprises a benzamide fungicide that inhibits succinate dehydrogenase (SDH) Complex II.

[0023] Embodiment 15: A method as described in Embodiment 14, wherein the benzamide fungicide is flucarbamide, flurenoxadiazam, flutolanil, o-amide, flutolanil, fluopyram, benzohydroxamic acid, flutolanil, fluopyram, flutolanil, thiocyanate, trchlamide, cyanamide or zoxamide.

[0024] Embodiment 16: The method of Embodiment 13, wherein the SDHI fungicide comprises a formamide fungicide that inhibits succinate dehydrogenase (SDH) Complex II.

[0025] Embodiment 17: The method of Embodiment 16, wherein the formamide fungicide is an oxathiin fungicide.

[0026] Embodiment 18: The method of Embodiment 17, wherein the oxathiin fungicide is carboxin or oxycarboxin.

[0027] Embodiment 19: The method of Embodiment 16, wherein the carboxamide fungicide is a furancarboxamide fungicide.

[0028] Embodiment 20: The method of Embodiment 19, wherein the furanamide fungicide is furamide, difuranamide, or furafuramide.

[0029] Embodiment 21. The method of Embodiment 16, wherein the carboxamide fungicide is a pyrazinecarboxamide fungicide.

[0030] Embodiment 22: The method of Embodiment 21, wherein the pyrazinecarboxamide fungicide is bixafenthrin.

[0031] Embodiment 23: The method of Embodiment 16, wherein the carboxamide fungicide is a pyrazolecarboxamide fungicide.

[0032] Embodiment 24: A method as described in Embodiment 23, wherein the pyrazole carboxamide fungicide is selected from the group consisting of: benzovinflupyr, bixafen, flufenoxam, flutolanil, flutolanil, flutolanil, furazolidone, indopoxylanil, isoproflupyramide, pyraclostrobin, flutolanil, penthiopyrad, flutolanil, pyridinamide, flutolanil, ethaconazole and thiopyrad.

[0033] Embodiment 25: The method of Embodiment 16, wherein the carboxamide fungicide is a pyridinecarboxamide fungicide.

[0034] Embodiment 26: The method of Embodiment 25, wherein the picolinamide fungicide is boscalid or triflupyridinamide.

[0035] Embodiment 27. The method of Embodiment 13, wherein the SDHI fungicide comprises a thiopheneamide fungicide.

[0036] Embodiment 28: A method according to Embodiment 27, wherein the thiopheneamide fungicide is isoflavone.

[0037] Embodiment 29: The method of any one of Embodiments 1 to 28, which provides increased overall yield of the plant.

[0038] Embodiment 30. The method of Embodiment 29, wherein the increased total yield of the plant is greater than the yield of a plant treated with the fungicide alone plus the yield of a plant treated with the one or more ascarosides alone.

[0039] Embodiment 31: The method of any one of Embodiments 1 to 30, which provides enhanced disease protection.

[0040] Embodiment 32. The method of Embodiment 31, wherein the enhanced disease protection is greater than the disease protection provided by treatment with the fungicide alone plus the disease protection provided by treatment with the one or more ascarosides alone.

[0041] Embodiment 33: The method of any one of Embodiments 1 to 32, wherein the co-administration comprises administering the fungicide and the one or more ascarosides in separate formulations.

[0042] Embodiment 34: The method of any one of Embodiments 1 to 32, wherein the co-administration comprises administering the fungicide and the one or more ascarosides in a single formulation.

[0043] Embodiment 35: A method as described in Embodiment 34, wherein the shelf life of the formulation is greater than 6 months.

[0044] Embodiment 36: The method of any one of Embodiments 1 to 35, wherein the one or more ascarosides have structure (I) Where: Z is an optionally substituted C 2-40 aliphatic group, and R a and R b Each of the following is independently -H, or an optionally substituted moiety selected from the group consisting of: C 1-20 Aliphatic group, C 1-20 Acyl, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus-linked functional group, sulfur-linked functional group, silicon-linked functional group, C 2-20 Carbonate (e.g., part -C(O)OR c ), C 2-20 Carbamate (e.g., part -C(O)N(R c )2) C 2-20 Thioesters (e.g., moieties -C(S)R c ), C 2-20 Thiocarbonates (e.g., moieties -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., part-C(S)SR c ), C 1-20Thiocarbamates (e.g., moieties -C(S)N(R c ) 2), a sugar moiety, a peptide, a polymer chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, wherein R c is independently selected at each occurrence from -H, optionally substituted C 1-12 aliphatic, optionally substituted C 1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, and wherein R a and R b Can be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

[0045] Embodiment 37: A method as described in Embodiment 36, wherein Z is selected from the group consisting of: (i) -CH(CH3)-R 1 , where R 1 Optionally substituted C 1-40 Aliphatic group; (ii) –CH(CH3)–(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (iii) -CH(CH3)-(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (iv) CH(CH3)-(CH2) n –CH(OH)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (v) -CH(CH3)-(CH2) n –C(O)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (vi) -(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (viii) -(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (viii) -(CH2) n –CH(OH)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; and (ix)—(CH2) n –C(O)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0046] Embodiment 38: A method as described in Embodiment 36, wherein Z is selected from the group consisting of: (x)-CH(CH3)-(CH2) n –CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xi) -CH(CH3)-(CH2) n –CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xii) -CH(CH3)-(CH2) n –CH(OH)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xiii) -CH(CH3)-(CH2) n –C(O)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xiii) –(CH2) n –CON(R 3)2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xiv)—(CH2) n –CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xv)—(CH2) n –CH(OH)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; and (xvi) —(CH2) n –C(O)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0047] Embodiment 39: A method as described in any one of embodiments 36 to 38, wherein R a and R b Each is -H.

[0048] Embodiment 40: A method as described in any one of Embodiments 36 to 39, wherein Z is -CH(CH3)-(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0049] Embodiment 41: The method of any one of Embodiments 1 to 35, wherein the one or more ascarosides comprises ascr#18.

[0050] Embodiment 42: The method of any one of Embodiments 1 to 41, wherein the plant or plant part is selected from plants or plant parts of crop plants (e.g., corn, alfalfa, sunflower, Brassica, soybean, cotton, safflower, peanut, sorghum, wheat, millet, or tobacco).

[0051] Embodiment 43: A method as described in any of Embodiments 1 to 42, wherein the activity is against plant diseases caused by fungi, viruses or viroids, protozoa, bacteria, and the like (e.g., diseases selected from the group consisting of Asian soybean rust (ASR), gray mold, leaf spot, gray spot, early blight, damping-off complex, brown spot, black mole, root rot, belly rot, sheath blight, powdery mildew, anthracnose leaf spot, downy mildew, pythium wilt, late blight, Fusarium head blight (FHB), sudden death syndrome (SDS), Fusarium wilt, corn stalk rot, brown rust, black rust, yellow rust, wheat rust, rust, apple scab, verticillium wilt, fire blight, and brown rot).

[0052] Embodiment 44: A composition comprising one or more ascarosides and one or more fungicides.

[0053] Embodiment 45: The composition of Embodiment 44, wherein the one or more fungicides comprise a biofungicide.

[0054] Embodiment 46: The composition of Embodiment 44, wherein the one or more fungicides comprise a chemical fungicide.

[0055] Embodiment 47: A composition as described in Embodiment 46, wherein the chemical fungicide is selected from the group consisting of azoles, methoxyacrylates, carboxamides, nitrogen-containing heterocyclic compounds, carbamates and dithiocarbamates, guanidines, antibiotics, organometallic compounds, sulfur-containing heterocyclic compounds, organophosphorus compounds, organochlorine compounds, nitrophenyl derivatives, inorganic active compounds, and combinations thereof.

[0056] Embodiment 48: A composition comprising one or more ascarosides and one or more fungicides comprising a triazole fungicide.

[0057] Embodiment 49: The composition of Embodiment 48, wherein the triazole fungicide is prothioconazole or tebuconazole.

[0058] Embodiment 50: A composition comprising at least one ascaroside and one or more fungicides, the one or more fungicides comprising at least one Q o 1. Fungicides.

[0059] Embodiment 51: A composition as described in Embodiment 50, wherein the Q o I fungicides include strobilurins.

[0060] Embodiment 52: A composition as described in Embodiment 51, wherein the methoxyacrylate is selected from the group consisting of: azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, enoxamyl, orysastrobin, fluoxastrobin, fenoxystrobin, tosoxstrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, kresoxim-methyl, fenamidone and famoxadone

[0061] Embodiment 53: The composition of Embodiment 52, wherein the strobilurin is azoxystrobin, picoxystrobin, or trifloxystrobin.

[0062] Embodiment 54: The composition of Embodiment 52, wherein the strobilurin is azoxystrobin.

[0063] Embodiment 55: A composition comprising at least one ascaroside and one or more fungicides, the one or more fungicides comprising a SDHI fungicide.

[0064] Embodiment 56. The composition of Embodiment 55, wherein the SDHI fungicide comprises a benzamide fungicide that inhibits succinate dehydrogenase (SDH) Complex II.

[0065] Embodiment 57: A composition as described in Embodiment 56, wherein the benzamide fungicide is flucarbamide, flurenoxadiazam, flutolanil, o-amide, flutolanil, fluopyram, benzohydroxamic acid, flutolanil, fluopyram, flutolanil, thiocyanate, trchlamide, cyanamide or zoxamide.

[0066] Embodiment 58. The composition of Embodiment 55, wherein the SDHI fungicide comprises a formamide fungicide that inhibits succinate dehydrogenase (SDHI) Complex II.

[0067] Embodiment 59: The composition of Embodiment 58, wherein the formamide fungicide is an oxathiin fungicide.

[0068] Embodiment 60: The composition of Embodiment 59, wherein the oxathiin fungicide is carboxin or oxycarboxin.

[0069] Embodiment 61. The composition of Embodiment 58, wherein the carboxamide fungicide is a furancarboxamide fungicide.

[0070] Embodiment 62: The composition of Embodiment 61, wherein the furanamide fungicide is furamide, difuranamide, or furafuramide.

[0071] Embodiment 63. The composition of Embodiment 58, wherein the carboxamide fungicide is a pyrazinecarboxamide fungicide.

[0072] Embodiment 64. The composition of Embodiment 63, wherein the pyrazinecarboxamide fungicide is bixafenthrin.

[0073] Embodiment 65. The composition of Embodiment 58, wherein the carboxamide fungicide is a pyrazolecarboxamide fungicide.

[0074] Embodiment 66: A composition as described in Embodiment 65, wherein the pyrazole carboxamide fungicide is selected from the group consisting of: benzovinflupyr, bixafen, flufenoxam, flutolanil, flutolanil, flutolanil, furazolidone, indopoxylanil, isoproflupyramide, pyraclostrobin, flutolanil, penthiopyrad, flutolanil, pyridinamide, flutolanil, ethaboxam and thiopyrad.

[0075] Embodiment 67. The composition of Embodiment 58, wherein the carboxamide fungicide is a pyridinecarboxamide fungicide.

[0076] Embodiment 68: The composition of any one of Embodiments 44 to 67, wherein the at least one ascaroside and the fungicide are present in effective amounts, and wherein the effective amounts provide synergistic activity in controlling fungal diseases.

[0077] Embodiment 69: The composition of any one of Embodiments 44 to 68, wherein the one or more ascarosides have structure (I), Where: Z is an optionally substituted C 3-40 aliphatic group, and R a and R b Each of the following is independently -H, or an optionally substituted moiety selected from the group consisting of: C 1-20 Aliphatic group, C 1-20 Acyl, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus-linked functional group, sulfur-linked functional group, silicon-linked functional group, C 2-20 Carbonate (e.g. part -C(O)OR c), C 2-20 Carbamate (e.g., part -C(O)N(R c )2) C 2-20 Thioesters (e.g., moieties -C(S)R c ), C 2-20 Thiocarbonates (e.g., moieties -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., part-C(S)SR c ), C 1-20 Thiocarbamates (e.g., moieties -C(S)N(R c ) 2), a sugar moiety, a peptide, a polymer chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, wherein R c is independently selected at each occurrence from -H, optionally substituted C 1-12 aliphatic, optionally substituted C 1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, and wherein R a and R b Can be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

[0078] Embodiment 70: A composition as described in Embodiment 69, wherein Z is selected from the group consisting of: (i) -CH(CH3)-R 1 , where R 1 is an optionally substituted C 1-40 Aliphatic group; (ii) –CH(CH3)–(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (iii) -CH(CH3)-(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (iv) -CH(CH3)-(CH2) n –CH(OH)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (v) -CH(CH3)-(CH2) n –C(O)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (vi) -(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (vii) -(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (viii) -(CH2) n –CH(OH)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; and (ix)—(CH2) n –C(O)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0079] Embodiment 71: The composition of claim 69, wherein Z is selected from the group consisting of: (x)—CH(CH3)—(CH2) n –CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xi) -CH(CH3)-(CH2) n –CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xii) -CH(CH3)-(CH2) n –CH(OH)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xiii) -CH(CH3)-(CH2) n –C(O)–CH-CON(R 3)2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xiv)—(CH2) n –CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xv)—(CH2) n –CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; (xvi)—(CH2) n –CH(OH)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linked to another ascaroside molecule via a bond or a carbon-containing linker moiety; and (xvii) —(CH2) n –C(O)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0080] Embodiment 72: A composition as described in any one of embodiments 69 to 71, wherein Ra and R b Each is -H.

[0081] Embodiment 73: A composition as described in any of Embodiments 69 to 72, wherein Z is -CH(CH3)-(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0082] Embodiment 74: The composition of any one of Embodiments 44 to 68, wherein the one or more ascarosides comprises ascr#18.

[0083] Embodiment 75: The composition of any one of Embodiments 44 to 74, which is in solid form.

[0084] Embodiment 76: The composition of Embodiment 75, wherein the solid form comprises powder or granules.

[0085] Embodiment 77: The composition of any one of Embodiments 44 to 74, which is in liquid form.

[0086] Embodiment 78: The composition of Embodiment 77, wherein the liquid form is a sprayable formulation.

[0087] Embodiment 79: The composition of Embodiment 77 or Embodiment 78, wherein the composition has a shelf life of greater than 6 months or greater than 12 months.

[0088] Embodiment 80: A composition as described in any of Embodiments 44 to 79, further comprising one or more additional components selected from the group consisting of: surfactants, including emulsifiers, dispersants, foam formers, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, ultraviolet radiation absorbers, weathering stabilizers, plasticizers, release agents, fragrances, thermal insulation additives (e.g., silica), cross-linking agents, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, extenders / stickers, tackifiers, plant penetrants, safeners, spreaders, and wetting agents.

[0089] Embodiment 81: The composition of any one of Embodiments 44 to 80, wherein the fungicide and the ascaroside are present in a weight ratio of greater than 1000: 1, greater than 1500: 1, greater than 2000: 1, greater than 3000: 1, greater than 5000: 1, or greater than 10,000: 1 fungicide:ascaroside.

[0090] Embodiment 82: The composition of any one of Embodiments 44 to 81, labeled for application to crops at a rate less than the labeled dosage rate of the fungicide alone.

[0091] Embodiment 83: The composition of any one of Embodiments 44 to 82 labeled for application to crops at a rate that delivers less than 4 ounces, less than 3 ounces, or less than 2.5 ounces of said fungicide per acre.

[0092] By reading the following specific embodiments and the accompanying drawings briefly described below, these and other features, aspects and advantages of the present disclosure will be understood. The present invention includes any combination of two, three, four or more of the above-mentioned embodiments and any two, three, four or more features or the combination of elements set forth in the present disclosure, regardless of whether these features or elements are clearly combined in the specific embodiment description of this paper. The present disclosure is intended to be read in an integral manner, so that any separable features or elements (in any one of its various aspects and embodiments) of the disclosed invention should be considered as intended to be combinable, unless the context clearly indicates otherwise. Other aspects and advantages of the present disclosure can be understood from the following. BRIEF DESCRIPTION OF THE DRAWINGS

[0093] The present teachings described herein may be more fully understood through the following description of various illustrative embodiments when read in conjunction with the accompanying drawings. It should be understood that each of the drawings described below is for illustration purposes only and is not intended to limit the scope of the present teachings in any way. The foregoing and other objects, aspects, features and advantages of the present disclosure may be more readily appreciated and better understood by reference to the following description in conjunction with the accompanying drawings, wherein:

[0094] Figure 1 Data are provided for non-limiting combinations of ascarosides with triazole fungicides;

[0095] Figure 2 is a graph of disease severity measurements obtained from a growth chamber / greenhouse experiment in which symptoms of leaf blight (Bipolaris sorokiniana) on spring wheat were scored following treatment with ascarosides. Treatments were performed in combination with the common Class 3 fungicide tebuconazole, and for comparison, treatments were performed with each product alone as well as an untreated control (blank).

[0096] Figure 3 is a graph of disease severity measurements obtained from field trials where Fusarium head blight symptoms (FHB) were scored on spring wheat following treatment with ascarosides ( 25 mg / ac) were treated in combination with the labeled dosage rate of two triazole fungicides (prothioconazole and tebuconazole), as compared to treatments with ascarosides alone or prothioconazole and tebuconazole alone and an untreated control (blank control);

[0097] Figure 4 is a graph of disease severity measurements obtained from field trials where Septoria leaf spot severity on wheat was scored following treatment with ascarosides ( 25 mg / ac) were treated in combination with the labeled dosage rate of prothioconazole, and as a comparison, ascaroside alone or prothioconazole alone were treated or an untreated control (blank control);

[0098] Figure 5 is a graph of Fusarium head blight disease indices obtained from field trials in which wheat was treated with ascarosides ( 25 mg / ac) in combination with the labeled dose rate of propiconazole and fluopicolide, as compared to treatment with ascarosides alone or propiconazole and fluopicolide alone or an untreated control (blank control);

[0099] Figure 6 is a graph of disease severity measurements obtained from field trials where Fusarium head blight symptoms (FHB) were scored on wheat following treatment with ascarosides ( 25 mg / ac) were treated in combination with the labeled dosage rate of prothioconazole, and as a comparison, ascaroside alone or prothioconazole alone were treated or an untreated control (blank control);

[0100] Figure 7 are soybean yield data for ascaroside treatments and control treatments from soybean field trials in Brazil where ASR was present;

[0101] Figure 8 Soybean yield data for ascaroside treatments and control treatments from a second soybean field trial site in Brazil where ASR was present are shown;

[0102] Fig. 9 ASR disease scores from soybean field trial sites in Brazil treated with ascarosides and controls are shown;

[0103] Fig.10 Photographs of representative leaves of soybean plants from a field trial site in Brazil (where ASR was present) treated with a combination of ascaroside and conventional fungicide or with conventional fungicide alone are shown;

[0104] Fig.11The results show that soybeans were scored for Asian soybean rust (ASR) and With fungicides (containing Q o Results of a field trial testing the synergistic effect of a combination of the 1-type fungicide picoxystrobin and the 5-type fungicide thiophanate-methyl (left). The right graph depicts the corresponding yields of the field trial. The fungicides were applied at the indicated dosage rate. Applied at 10 μM (205 mg / acre). Error bars represent standard error of the mean. For one-way ANOVA with Tukey's multiple comparison test, * = P ≤ 0.05 and **** = P ≤ 0.0001;

[0105] Fig.12 Graph showing disease severity measurements obtained from a field trial in which soybeans were inoculated with Asian soybean rust and disease symptoms (FHB) were scored following treatments with ascarosides (50 mg / ac) in combination with the labeled dose rate application of azoxystrobin, as a comparison: ascarosides alone treatment; combination treatment with ascarosides and azoxystrobin; and TRIVAPRO TM (a commercial fungicide containing a 3-way blend of propiconazole, azoxystrobin, and benzovinflumizone);

[0106] Fig.13 Shows the Fig.12 A graph of soybean yields from the trials described in ;

[0107] Fig.14 Graph showing symptoms of "spot blight" disease of wheat (caused by the fungal pathogen Helminthosporium spp.) comparing an untreated control (blank) with treatments with azoxystrobin alone at 1 / 20 of the labeled application rate (azoxystrobin); Treatments at 25 mg / acre equivalent and treatments with azoxystrobin and ascarosides in combination were compared;

[0108] Fig.15 A graph showing symptoms of "spot blight" disease of wheat (caused by the fungal pathogen Helicoverpa spp.) comparing an untreated control (blank) with treatments with fluopoxadim (SDHI fungicide); Treatments at 25 mg / acre equivalent and treatments with a combination of fluopyram and ascarosides were compared;

[0109] Fig.16 showed that the growth of seeds from untreated seeds (blank control), treated with ascaroside Treated seeds, treated with chemical fungicides (Apron Maxx TM ) and seeds treated with ascarosides and chemical fungicides ( Graph showing the incidence of bacterial leaf streak in field trial plots of wheat grown from seeds treated with Apron Maxx;

[0110] Fig.17 showed that the growth of seeds from untreated seeds (blank control), treated with ascaroside Treated seeds, treated with chemical fungicides (Cruiser Maxx TM ) and seeds treated with both ascaroside and chemical fungicides ( +Cruiser Maxx TM ) treated seeds in a field trial plot of corn; and

[0111] Fig.18 The results showed that the growth of seeds with untreated seeds (blank control), treated with ascaroside Treated seeds, treated with chemical fungicides (Apron Maxx TM ) and seeds treated with ascarosides and chemical fungicides ( +Apron Maxx TM )-treated seeds.

[0112] definition

[0113] In order to make the present disclosure more easily understood, certain terms will first be defined below. Additional definitions of the following terms and other terms are set forth throughout the specification.

[0114] In this application, unless the context clearly indicates otherwise, the terms "a" and "an" may be understood to mean "at least one". As used in this application, the term "or" may be understood to mean "and / or". In this application, the terms "comprising" and "including" may be understood to cover the listed components or steps, either alone or with one or more additional components or steps. As used in this application, the term "comprise" and variations thereof, such as "comprising" and "comprises" are not intended to exclude other additives, components, integers or steps.

[0115] As used herein, the terms "about" and "approximately" are used as equivalents. Unless otherwise specified, the terms "about" and "approximately" can be understood to allow standard variations, as understood by those of ordinary skill in the art. If a range is provided herein, endpoints are included. Any numeral with or without about / approximately used in this application is intended to cover any normal fluctuations understood by those of ordinary skill in the relevant art. In some embodiments, the term "about" or "approximately" refers to falling into 25%, 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1% or a numerical range in a smaller range on either direction (greater than or less than) of the reference value, unless otherwise specified or apparent from the context (unless the numeral exceeds 100% of a possible value).

[0116] The definitions of specific functional groups and chemical terms are described in more detail below. For purposes of the present invention, chemical elements are identified according to the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75th edition, inside cover, and specific functional groups are generally defined as described therein. In addition, the general principles of organic chemistry 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, 5th edition, John Wiley & Sons, Inc., New York, 2001; Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989; Carruthers, Some Modern Methods of Organic Synthesis, 3rd edition, Cambridge University Press, Cambridge, 1987; each of which is incorporated herein by reference in its entirety.

[0117] 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. Therefore, the compounds of the present invention and compositions thereof may be in the form of individual enantiomers, diastereomers or geometric isomers, or in the form of a mixture of stereoisomers. In certain embodiments, the compounds described herein are enantiomerically pure compounds. In certain other embodiments, a mixture of enantiomers or diastereomers is provided.

[0118] In addition, certain compounds as described herein may have one or more double bonds, which may exist as Z or E isomers unless otherwise indicated. Compounds may be provided as individual isomers substantially free of other isomers, or as mixtures of various isomers (e.g., racemic mixtures of enantiomers).

[0119] As used herein, the term "isomer" includes any and all geometric isomers and stereoisomers. For example, "isomer" includes cis and trans isomers, E- and Z-isomers, R- and S-enantiomers, diastereomers, (D)-isomers, (L)-isomers, racemic mixtures thereof, and other mixtures thereof as fall within the scope of the present disclosure. For example, in some embodiments, a compound may be provided that is substantially free of one or more corresponding stereoisomers, and it may also be referred to as "stereochemically enriched".

[0120] When a particular enantiomer is preferred, in some embodiments, the enantiomer may be substantially free of the opposite enantiomer, also referred to as "optically enriched". As used herein, "optically enriched" means that the compound consists of one enantiomer, and the ratio is significantly increased. In certain embodiments, the compound is composed of at least about 90% by weight of the enantiomer. In some embodiments, the compound is composed of at least about 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9% by weight of the enantiomer. In some embodiments, the enantiomeric excess of the provided compound is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9%. In some embodiments, enantiomers can be separated from the racemic mixture by any method known to those skilled in the art, including chiral high pressure liquid chromatography (HPLC) and the formation and crystallization of chiral salts, or prepared by asymmetric synthesis. See, for example, Jacques et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981); Wilen, SH et al., Tetrahedron 33: 2725 (1977); Eliel, EL Stereochemistry of Carbon Compounds (McGraw-Hill, NY, 1962); Wilen, SH Tables of Resolving Agents and Optical Resolutions p. 268 (EL Eliel, Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0121] As used herein, the terms "halo" and "halogen" refer to an atom selected from fluorine (F, —F), chlorine (Cl, —Cl), bromine (Br, —Br), and iodine (I, —I).

[0122] As used herein, the term "aliphatic" or "aliphatic group" means a hydrocarbon portion that may be straight chain (i.e., unbranched), branched, or cyclic (including fused, bridged, and spiro-fused polycyclics) and may be fully saturated or may contain one or more unsaturated units but is not aromatic. Unless otherwise specified, 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 other embodiments, an aliphatic group contains 1-3 carbon atoms, and in other embodiments, an aliphatic group contains 1-2 carbon atoms. Suitable aliphatic groups include, but are not limited to, straight or branched alkyl, alkenyl, and alkynyl groups and mixtures thereof such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl.

[0123] As used herein, the term "heteroaliphatic" or "heteroaliphatic group" refers to an aliphatic group in which one or more carbon or hydrogen atoms are replaced by a heteroatom (eg, oxygen, nitrogen, sulfur, phosphorus, boron, etc.).

[0124] As used herein, the term "unsaturated" means a moiety having one or more double or triple bonds.

[0125] The term "alkyl" as used herein refers to a saturated, straight or branched hydrocarbon group derived from an aliphatic portion containing one to six carbon atoms by removing a single hydrogen atom. Unless otherwise specified, an alkyl group contains 1-12 carbon atoms. In certain embodiments, 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 other embodiments, an alkyl group contains 1-3 carbon atoms, and in other embodiments, an alkyl group contains 1-2 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, sec-pentyl, isopentyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, n-decyl, n-undecyl, dodecyl, etc.

[0126] The term "alkenyl" as used herein means a monovalent group derived from a straight or branched aliphatic moiety, wherein the alkenyl group has at least one carbon-carbon double bond by removing a single 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 other embodiments, an alkenyl group contains 2-3 carbon atoms, and in other embodiments, an alkenyl group contains 2 carbon atoms. An alkenyl group includes, for example, vinyl, propenyl, butenyl, 1-methyl-2-butene-1-yl, etc.

[0127] The term "aryl", used alone or as part of a larger moiety in "aralkyl", "aralkyloxy", or "aryloxyalkyl", refers to monocyclic and polycyclic ring systems having a total of 5 to 20 ring members, wherein at least one ring in the system is aromatic and wherein each ring in the system contains three to twelve ring members. The term "aryl" can be used interchangeably with the term "aromatic ring". In certain embodiments, "aryl" refers to an aromatic ring system including, but not limited to, phenyl, biphenyl, naphthyl, anthracenyl, etc., which may carry one or more substituents. Also included within the scope of the term "aryl", as used herein, are groups in which an aromatic ring is fused to one or more additional rings, such as benzofuranyl, indanyl, phthalimido, or tetrahydronaphthyl, etc.

[0128] As described herein, compounds as provided herein may contain "optionally substituted" moieties. In general, whether or not the term "optionally" is added in front, the term "substituted" means that one or more hydrogens of the specified part are replaced by suitable substituents. Unless otherwise specified, the "optionally substituted" group may have a suitable substituent at each substitutable position of the group, and when more than one position in a given structure can be substituted by more than one substituent selected from a specified group, the substituent may be the same or different at each position. The combination of substituents envisioned is preferably a combination of stable or chemically feasible compounds. The term "stable" as used herein refers to a compound that is substantially unchanged when subjected to conditions that allow compound preparation, detection, and in certain embodiments, its recovery, purification, and use for one or more purposes disclosed herein.

[0129] Suitable monovalent substituents on the substitutable carbon atoms of the "optionally substituted" group are independently halogen; -(CH2) 0–4 R o ; –(CH2) 0–4 OR o ; -O-(CH2) 0-4 C(O)OR o; –(CH2) 0–4 CH(OR o )2; –(CH2) 0–4 SR o ; –(CH2) 0–4 Ph, it can be R o Substitution; –(CH2) 0–4 O(CH2) 0–1 Ph, it can be R o Substitution; –CH=CHPh, which can be replaced by R o Substitution; –NO2; –CN; –N3; –(CH2) 0–4 N(R o )2; –(CH2) 0–4 N(R o )C(O)R o ; –N(R o )C(S)R o ; –(CH2) 0-4 N(R o )C(O)NR o 2; –N(R o )C(S)NR o 2; –(CH2) 0–4 N(R o )C(O)OR o ;-N(R o )N(R o )C(O)R o ; –N(R o )N(R o )C(O)NR o 2; –N(R o )N(R o )C(O)OR o ; –(CH2) 0–4 C(O)R o ;-C(S)R o ; –(CH2) 0–4 C(O)OR o ; –(CH2) 0–4 C(O)N(R o )2; –(CH2) 0–4 C(O)SR o ; –(CH2) 0–4 C(O)OSiR o 3; –(CH2) 0–4 OC(O)R o ; –OC(O)(CH2) 0–4 SR–, SC(S)SR o ; –(CH2) 0–4SC(O)R o ; –(CH2) 0–4 C(O)NR o 2; -C(S)NR o 2; –C(S)SR o ; –SC(S)SR o 、–(CH2) 0–4 OC(O)NR o 2; –C(O)N(OR o )R o ; –C(O)C(O)R o ; -C(O)CH2C(O)R o ; –C(NOR o )R o ; –(CH2) 0–4 SSR o ; -(CH2) 0–4 S(O)2R o ; –(CH2) 0–4 S(O)2OR o ; -(CH2) 0–4 OS(O)2R o ; –S(O)2NR o 2; –(CH2) 0–4 S(O)R o ; –N(R o )S(O)2NR o 2; –N(R o )S(O)2R o ;-N(OR o )R o ; –C(NH)NR o 2; –P(O)2R o ; –P(O)R o 2;–OP(O)R o 2;–OP(O)(OR o )2;SiR o 3;–(C 1–4 Straight or branched alkylene)O–N(R o )2; or – (C 1–4 Straight or branched alkylene) C(O)O–N(R o )2, where each R o may be substituted as defined below and are independently hydrogen, C 1-8 Aliphatic, –CH2Ph, –O(CH2) 0–1 Ph or a 5-6 membered saturated, partially unsaturated or aromatic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur, or, notwithstanding the definitions given above, two independent occurrences of Ro Together with their intervening atoms they form a 3-12 membered saturated, partially unsaturated or aromatic monocyclic or polycyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur, said ring may be substituted as defined below.

[0130] In R o (or two independent occurrences of R o Suitable monovalent substituents on the ring formed together with their intervening atoms are independently halogen, –(CH2) 0–2 R · 、–(halogenated R · ),–(CH2) 0–2 OH, –(CH2) 0–2 OR · 、–(CH2) 0–2 CH(OR · )2; -O(halogenated R · )、–CN、–N3、–(CH2) 0–2 C(O)R · 、–(CH2) 0–2 C(O)OH, –(CH2) 0–2 C(O)OR · 、-(CH2) 0-4 C(O)N(R o )2; –(CH2) 0–2 SR · 、–(CH2) 0–2 SH, –(CH2) 0–2 NH2, –(CH2) 0–2 NHR · 、-(CH2) 0-2 NR · 2. –NO2, –SiR · 3. –OSiR · 3. –C(O)SR · ,–(C 1–4 Straight or branched alkylene)C(O)OR · or –SSR · , where each R · is unsubstituted or, when preceded by "halo", is substituted only by one or more halogens, and is independently selected from C 1–4 Aliphatic, -CH2Ph, –O(CH2) 0–1 Ph or a 5-6 membered saturated, partially unsaturated or aromatic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur. o Suitable divalent substituents on a saturated carbon atom of include =0 and =S.

[0131] Suitable divalent substituents on a saturated carbon atom of an "optionally substituted" group include the following: =0, =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–, where each independent occurrence of R * Selected from hydrogen, C 1–6 an aliphatic group (which may be substituted as defined below) or an unsubstituted 5-6 membered saturated, partially unsaturated or aromatic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur. Suitable divalent substituents attached to an adjacent substitutable carbon of an "optionally substituted" group include: -O(CR * 2) 2–3 O–, where each independent occurrence of R * is selected from hydrogen, C which may be substituted as defined below 1–6 aliphatic, or an unsubstituted 5-6 membered saturated, partially unsaturated or aromatic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur.

[0132] R * Suitable substituents on the aliphatic group include halogen, -R · 、-(halogenated R · ), –OH, –OR · 、–O(halogenated R · ), –CN, –C(O)OH, –C(O)OR · , –NH2, –NHR · ,–NR · 2 or –NO2, where each R · is unsubstituted or, when preceded by "halo", is substituted only by one or more halogens, and is independently C 1–4 Aliphatic, –CH2Ph, –O(CH2) 0– 1Ph or a 5-6 membered saturated, partially unsaturated or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur.

[0133] Suitable substituents on a substitutable nitrogen of an "optionally substituted" group include Each of these are independently hydrogen, substituted C 1–6aliphatic, unsubstituted -OPh or an unsubstituted 5-6 membered saturated, partially unsaturated or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur, or, notwithstanding the definitions given above, two independent occurrences of Together with their intervening atom(s), they form a 3-12 membered saturated, partially unsaturated or aromatic monocyclic or bicyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur.

[0134] Suitable substituents on the aliphatic group are independently halogen, -R · 、-(halogenated R · ), –OH, –OR · 、–O(halogenated R · ), –CN, –C(O)OH, –C(O)OR · , –NH2, –NHR · ,–NR · 2 or -NO2, where each R · is unsubstituted or, when preceded by "halo", is substituted only by one or more halogens, and is independently C 1–4 Aliphatic, –CH2Ph, –O(CH2) 0–1 Ph or a 5-6 membered saturated, partially unsaturated or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen or sulfur.

[0135] As used herein, the term "substantially" refers to the qualitative condition of exhibiting the full or nearly full extent or degree of a characteristic or property of interest.

[0136] A convention of naming ascarosides with a prefix of several letters followed by a pound sign (#) and a number is sometimes used (e.g., ascr#18). This convention is used in the scientific literature, and one skilled in the art will understand that each such name is associated with a specific chemical structure of known composition, and will readily understand the structure of the molecule referred to using this naming convention. Unless otherwise indicated, all compound identifiers in this format used herein conform to the definitions described in the C. elegans Small Molecule Identifier Database (SMID-DB) (maintained at http: / / www.smid-db.org).

[0137] The term "pathogen" refers to any bacterium, fungus, oomycete, virus, nematode (eg, cyst nematode or root knot nematode), or insect that is pathogenic to plants. DETAILED DESCRIPTION

[0138] Compositions and methods of use of ascarosides are provided. The present disclosure relates to plant treatments with one or more ascarosides and one or more additional active agents (e.g., fungicides or other antimicrobial agents). In certain embodiments, the present disclosure provides combinations of one or more naturally occurring ascarosides (which have biological origins and modes of action that classify them as biologicals (e.g., biofungicides)) with one or more synthetic chemical fungicides. It is well known that co-application of biologicals with chemical fungicides often results in reduced activity of the biologicals, or creates other challenges related to physical or chemical incompatibilities of the biological and chemical agents or requirements for different application times or methods. In certain embodiments, application of the provided biological / synthetic combinations is unexpectedly stable and exhibits unexpected additive or synergistic effects given very different modes of action and application rates. Certain fungicides suitable for inclusion in the provided compositions and methods include, but are not limited to, chemical fungicides such as triazole fungicides, strobilurin fungicides, or SDHI fungicides. According to the present disclosure, treatment can be performed by administering one or more ascarosides and one or more additional active agents separately, or can be performed by a composition comprising one or more ascarosides and one or more additional active agents. In some embodiments, one or more ascarosides and one or more additional active agents exhibit a synergistic effect.

[0139] Ascarosides

[0140] Ascarosides are derivatives of ascarylose, a dideoxy sugar lacking hydroxyl groups at positions 3 and 6. Ascarosides have the general structure shown in Formula I:

[0141]

[0142] in:

[0143] Z is an optionally substituted C 2-40 an aliphatic group, and

[0144] R a and R b Each of the following is independently -H, or an optionally substituted moiety selected from the group consisting of: C 1-20 Aliphatic group, C 1-20 Acyl, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus-linked functional group, sulfur-linked functional group, silicon-linked functional group, C 2-20 Carbonate (e.g., part -C(O)OR c ), C 2-20 Carbamate (e.g., part -C(O)N(R c )2) C 2-20Thioesters (e.g., moieties -C(S)R c ), C 2-20 Thiocarbonates (e.g., moieties -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., part-C(S)SR c ), C 1-20 Thiocarbamates (e.g., moieties -C(S)N(R c ) 2), a sugar moiety, a peptide, a polymer chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, wherein R c is independently selected at each occurrence from -H, optionally substituted C 1-12 aliphatic, optionally substituted C 1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, and wherein R a and R b Can be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

[0145] In certain embodiments, Z is:

[0146] (i) –CH(CH3)–R 1 , where R 1 is an optionally substituted C 1-40 aliphatic groups;

[0147] (ii) –CH(CH3)–(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0148] (iii) –CH(CH3)–(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0149] (iv) –CH(CH3)–(CH2) n –CH(OH)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0150] (v) –CH(CH3)–(CH2) n –C(O)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0151] (vi)–(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0152] (vii)–(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0153] (viii)–(CH2) n –CH(OH)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; or

[0154] (ix)–(CH2) n –C(O)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0155] In certain embodiments, Z is:

[0156] (x)–CH(CH3)–(CH2) n –CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0157] (xi)–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0158] (xii)–CH(CH3)–(CH2) n –CH(OH)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0159] (xiii) –CH(CH3)–(CH2) n –C(O)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0160] (xiv)–(CH2) n –CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0161] (xv)–(CH2) n –CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety;

[0162] (xvi)–(CH2) n –CH(OH)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; or

[0163] (xvii)–(CH2) n –C(O)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0164] In certain embodiments, R a Yes -H.

[0165] In certain embodiments, R b Yes -H.

[0166] In certain embodiments, R a and R b In certain embodiments, R a and R b All are -H.

[0167] In certain embodiments, R a and R b In certain embodiments, R a Yes -H, and R b is a group other than -H. In certain embodiments, R a is a group other than -H and R b is -H. In certain embodiments, R a Yes -H and R b is a paraben. In certain embodiments, R a Yes -H and R b is indole-3-carboxylate. In certain embodiments, R a Yes -H and R b is (E)-2-methyl-2-butenoate. In certain embodiments, R a Yes -H and R b is a picolinate. In certain embodiments, R a Yes -H and R b In certain embodiments, R a Yes -H and R b is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, R a Yes -H and R b It is 4-((4-hydroxyphenethyl)amino)-4-oxobutanoate.

[0168] In certain embodiments, R a and R b are all -H, and Z is selected from the formulae defined in (i) to (xvii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (i) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (ii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (iii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (iv) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (v) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (vi) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (vii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (viii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (ix) above. In certain embodiments, R a and R b are -H, and Z conforms to Formula (x) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (xi) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (xii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (xiii) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (xiv) above. In certain embodiments, R a and R b are -H, and Z conforms to formula (xv) above. In certain embodiments, R a and R bare -H, and Z conforms to formula (xvi) above. In certain embodiments, R a and R b All are -H, and Z conforms to formula (xvii) above.

[0169] In certain embodiments, R 2 is -H. In certain embodiments, R 2 is a metal cation. In certain embodiments, R 2 is an organic cation (e.g., a nitrogen or phosphorus-centered cationic group). 2 is an optionally substituted C 1-20 In certain embodiments, R 2 is an optionally substituted C 1-12 In certain embodiments, R 2 is an optionally substituted C 1-8 In certain embodiments, R 2 is an optionally substituted C 1-6 In certain embodiments, R 2 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl. 2 is an optionally substituted aromatic group. In certain embodiments, R 2 is a glycoside. In certain embodiments, R 2 In certain embodiments, R 2 In certain embodiments, R 2 Contains nucleotides.

[0170] In certain embodiments, at least one R 3 In certain embodiments, both R 3 The group is -H. In certain embodiments, at least one R 3 is an optionally substituted C 1-20 In certain embodiments, two R 3 The group is an optionally substituted C 1-20 aliphatic groups, which may be the same or different. In certain embodiments, at least one R 3 is an optionally substituted C 1-12 In certain embodiments, at least one R 3 is an optionally substituted C 1-8 In certain embodiments, at least one R 3 is an optionally substituted C 1-6 In certain embodiments, at least one R 3is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl. 3 is -CH2CH2OH. In certain embodiments, at least one R 3 Yes -CH2CH2OR 2 , where R 2 As defined in the genus and subgenus herein. In certain embodiments, at least one R 3 is an optionally substituted aromatic group. In certain embodiments, at least one R 3 In certain embodiments, at least one R 3 In certain embodiments, at least one R 3 At least one R 3 In certain embodiments, at least one R 3 Contains nucleotides.

[0171] In certain embodiments, the ascaroside is selected from the group consisting of:

[0172]

[0173] Where x is an integer from 1 to 22, and R a , R b and R 2 Each of which is as defined above and in the genera and subgenera herein.

[0174] In certain embodiments, the ascaroside is selected from the group consisting of:

[0175]

[0176] Where x, R a and R b Each of which is as defined above and in the genera and subgenera herein.

[0177] In certain embodiments, the ascaroside is selected from the group consisting of:

[0178]

[0179] Where y is an integer from 1 to 20, and R a , R b and R 2 Each of which is as defined above and in the genera and subgenera herein.

[0180] In certain embodiments, the ascaroside is selected from the group consisting of:

[0181]

[0182] Where y, R a and R b Each of which is as defined above and in the genera and subgenera herein.

[0183] In certain embodiments, the ascaroside is selected from the group consisting of:

[0184]

[0185] Where x is an integer from 1 to 22, and R 2 As defined above and in the genus and subgenera herein.

[0186] In certain embodiments, the ascaroside is selected from the group consisting of:

[0187]

[0188] wherein x is as defined above and in the genera and subgenera herein.

[0189] In certain embodiments, the ascaroside is selected from the group consisting of:

[0190]

[0191] Where y is an integer from 1 to 20, and R 2 As defined above and in the genus and subgenera herein.

[0192] In certain embodiments, the ascaroside is selected from the group consisting of:

[0193]

[0194] wherein y is as defined above and in the genus and subgenera herein.

[0195] In certain embodiments, the ascaroside is selected from the group consisting of:

[0196]

[0197] Where x is an integer from 1 to 22, and R a , R b and R 3 Each of which is as defined above and in the genera and subgenera herein.

[0198] In certain embodiments, the ascaroside is selected from the group consisting of:

[0199]

[0200] where x and R 3 Each of which is as defined above and in the genera and subgenera herein.

[0201] In certain embodiments, the ascaroside is selected from the group consisting of:

[0202]

[0203] Where y is an integer from 1 to 20, and R a , R b and R 2 Each of which is as defined above and in the genera and subgenera herein.

[0204] In certain embodiments, the ascaroside is selected from the group consisting of:

[0205]

[0206] where y and R 3 Each of which is as defined above and in the genera and subgenera herein.

[0207] In one embodiment, the ascarosides used in the context of the present disclosure have the general structure (I), wherein Z is -CH(CH3)-(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides, and can be used to inhibit the growth of human pathogenic bacteria in or on plants.

[0208] In one embodiment, the ascarosides used in the context of the present disclosure have the general structure (I), wherein Z is -CH(CH3)-(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0209] Specific ascarosides for use in the context of the present disclosure include, but are not limited to, ascr#7 and ascr#18.

[0210]

[0211] In certain embodiments, the ascarosides used in the provided methods and compositions are selected from the group consisting of ascr#9, ascr#12, ascr#14, ascr#1, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, ascr#24, ascr#26, ascr#28, ascr#30, ascr#32, ascr#34, and ascr#36. In certain embodiments, the ascarosides used in the provided methods are selected from the group consisting of ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. In certain embodiments, the ascarosides used in the provided methods are selected from the group consisting of ascr#9, ascr#14, ascr#10, and ascr#18.

[0212] In certain embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of ascr#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, 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.

[0213] In certain embodiments, the ascarosides used in the provided methods and compositions are 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.

[0214] In certain embodiments, the ascarosides used in the provided methods and compositions are 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.

[0215] In certain embodiments, the ascarosides used in the provided methods and compositions are selected from the group consisting of ascr#18, oscr#16, oscr#17, oscr#15, bhas#18, bhos#16, glas#18, dhas#18, ibha#18, ibho#16, icas#18, icos#15, icos#16, and any combination of two or more of these.

[0216] In some embodiments, the ascaroside used in the provided methods and compositions is an ascaroside salt as disclosed in International Application PCT / US2023 / 21731 filed on May 10, 2023, or an ascaroside modified to provide extended release of the active ingredient as disclosed in International Application PCT / US2023 / 20472 filed on April 28, 2023, both of which are incorporated herein by reference in their entirety.

[0217] Ascarosides can be obtained from natural sources (e.g., nematodes) or prepared synthetically. Ascarosides can be prepared synthetically, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascarosides. An exemplary method for preparing ascarosides includes: providing 1-O-substituted rhamnose as a raw material; forming a monosulfonate on the 3-OH group of the raw material; and treating the monosulfonate with a hydride source to form a 1-O-substituted ascarosides. In certain embodiments, the formation of the monosulfonate is carried out on a substrate having no hydroxyl protecting group at position 2 or 4 of the rhamnose raw material. In certain embodiments, such methods include contacting the raw material with a sulfonating agent (i.e., a sulfonyl halide, a sulfonic anhydride, or a similar reagent) in the presence of a Lewis acid. Specific details about the synthesis of 1-O-substituted ascarosides can be found in PCT application publication WO / 2022 / 024067, which is incorporated herein by reference.

[0218] Additional active agents

[0219] As provided herein, one or more additional active agents in the various methods and compositions encompass all compounds understood to exhibit beneficial activity against one or more pathogens. Such active agents are typically antimicrobial agents, and include but are not limited to antibacterial agents (also referred to as bactericides), antifungal agents (also referred to as fungicides), insecticides (also referred to as insecticides) and anthelmintics (also referred to as nematicides).

[0220] The antimicrobial agents used in the disclosed methods and formulations are not particularly limited. Suitable active agents can be preventive active agents or therapeutic active agents, can have single-site activity or multi-site activity, can be narrow-spectrum active agents or broad-spectrum active agents, and can be organic active agents or inorganic active agents. They can be chemical active agents or biological active agents. In some embodiments, the active agent is a natural active agent, and its active ingredients include but are not limited to sulfur, lime sulfur, copper (e.g., copper sulfate form), oil (e.g., horticultural oil, neem oil, rosemary oil and jojoba oil), bicarbonate (e.g., sodium bicarbonate, potassium bicarbonate and ammonium bicarbonate) and their combinations.

[0221] Certain general chemical classes of suitable fungicidal compounds for use in certain embodiments as disclosed herein include, but are not limited to, substituted benzenes, thiocarbamates, dithiocarbamates, copper thiophthalimide compounds, nitriles / benzonitriles / chloronitriles, benzimidazoles, dicarboximides, carboxamides / anilides, methoxyacrylates, phenylpyrroles, aromatic hydrocarbons, polyoxins, pyridinamines, phenylamides, cyanoimidazoles, phosphonates, and combinations thereof. Fungicides used in the various formulations and methods described herein can also be defined by, for example, the following modes of action: mitotic disruptors (e.g., thiophanates, such as thiophanate-methyl); cell membrane disruptors (e.g., triazoles, such as cyproconazole, difenoconazole, flutriafol, mefentrifluconazole, metconazole, propiconazole, tebuconazole, and tetraconazole; and triazolinethiones, such as prothioconazole); respiratory inhibitors (e.g., succinate dehydrogenase inhibitors / carboxamides, such as pyridinecarboxamides (e.g., boscalid), pyridyl-ethylbenzamides (e.g., fluopyram), and pyrazole-4-carboxamides (e.g., benzophenoneflurofen); oxazolidinone (benzovindiflupyr, bixafen, fluxapyroxad, penthiopyrad, pydiflumetofen) and quinone external inhibitors / strobins, such as strobins (e.g., azoxystrobin and picoxystrobin), dihydro-dioxazines (e.g., fluoxastrobin), methoxy -carbamates (e.g., pyraclostrobin) and oxime-acetates (e.g., trifluoxystrobin); oxidative phosphorylation uncouplers (e.g., 2,6-dinitroanilines such as fluazinam); fungicides of unknown activity (e.g., phosphonates such as phosphorous acid and phosphites); and fungicides with multi-site contact activity (e.g., inorganic fungicides, e.g., copper salts and chloronitriles / phthalonitriles such as Chlorothalonil).

[0222] Suitable specific additional active agents include, but are not limited to, acibenzolar, acibenzoloar-S-methyl, Agrobacterium radiobacter, aldicarb, aliphatic petroleum distillates, allyl isothiocyanate, trialuminum, ametoctradin, 2-aminobutane, Ampelomyces quisqualis, anilazine, Aureobasidium pullulans (e.g., strains DSM 14940 and 14941), azadirachtin, azoxystrobin, Bacillus amyloliquefaciens (e.g., strains D747 or F727), Bacillus firmus (e.g., strains D747 or F727), firmus (e.g., strain I-1582), Bacillus mycoides (e.g., isolate J), ​​Bacillus pumilus (e.g., strain QST 2808), Bacillus subtilis (e.g., strain IAB / BS03, strain QST 713, strain BG03, or strain MBI 600), basic copper carbonate, benomyl, benz ovindiflupyr, bifenazate, bixafen, BLAD, borax, boric acid, boscalid, Burkholderia cepacia, Candida oleifera, oleophila), capric and caprylic acid, captafol, captan, carbendazim, carbofuran, carbon disulfide, carboxin, chitin, chlorfenapyr, chlorine dioxide, chloroneb, chloropicrin, chlorothalonil, cinnamaldehyde, ciproconazole, clove oil, Coniothyrium mi nitans (e.g., strain CON / M / 91-08), copper, copper ammonium complexes (e.g.,ammonium cupric carbonate, tannate complex of ammonium cupric formate), diacetate diamine complex, copper hydroxide, copper octoate, copper oxide, copper oxychloride, copper sulfate, cresol, cyazofamid, cyclohexane polymer, cycloheximide, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, dichlone, dichloran, dichloropropylene, dicofol, difenoconazole, difenoxazole, difolatan, dimethomorph, demeton, dimethyl disulfide, dinocap, dodemorph acetate acetate), dodine, epoxiconazole, ethaboxam, ethoprop, ethoxyquin, ethylene dibromide, ethaboxam, etridiazole, famoxadone, fenamidone, fenaminosulf, fenamiphos, fenarimol, fenazaquin, fenbuconazole, fenhexamid, fenpyrazamine, fensulfothion, ferbam, fluazinam, fludioxonil, fluensulfone, fluopicolide, fluopyram, fluoxastrobin n), fluquinconazole, flusilazole, flutian il, flutolanil, flutriafol, fluxapyroxa d, folpet, formaldehyde, fosetyl-Al, gamma-aminobutyric acid, gibberellic acid, Gliocladium catenalatum (e.g.,strain J1446), Gliocladium virens, harpin, hexachlorobenzene, horticultural mineral oil, slaked lime, hymexazole, imazalil, iodomethane, ipconazole, iprodione, isofetamidopropamide, jojoba oil, kasugamycin, kresoxim-methyl, L-glutamic acid, laminarin, lime sulfur, mandestrobin, mandipropamid, maneb, mancozeb, mefenoxam, mefentrifluconazole, metalaxyl, metamethane sodium), metconazole, methyl bromide, methylcyclopropene, methyl isothiocyanate, metrafenone, methyl bromide, methylcyclopropene, metiram, myclobutanil, Myrothecium verrucaria (e.g., strain AARC-0255), neem oil, oxadixyl, oxamyl, oxthioquinox, oxathiapiprolin, oxycarboxin, oxytetracycline, oxythioquinox, Paecilomyces lilacinus (e.g., strain 251), Pantoea agglomerans (e.g.,strain E325), parinol, pentachloronitrobenzene (PCNB), penthiopyrad, peroxide, peracetic acid, peroxyhydrate, petroleum, phenylmercuric acetate, phosphites, phosphorous acid, picoxystrobin, polyalkylene-modified heptamethyltrisiloxane, polyoxin D, polyoxin D zinc salt, potassium bicarbonate, potassium phosphite, potassium silicate, prohexadione calcium, propamocarb, propiconazole, prothioconazole, Pseudomonas aureofaciens, Pseudomonas chlororaph is (e.g., strain AFS009), Pseudomonas fluorescens, Pseudomonas syringae ... syringae), pydiflumetofen, pyraclostrobin, pyrimethanil, pyr iofenone, quaternary ammonium, quinoxyfen, Reynoutria sacha linensis, rosemary oil, saponins, sedaxane, sodium hypochlorite, spiroxamine, Streptomyces griseoviridis (e.g., strain 61), streptomycin, sulfur, Swinglea glutinosa, tebuconazole tetrathiocarbonate, thiabendazole, thiamethoxam m), thiophanate, thiophanate-methyl, thiram, thyme oil, triadimefon, triadimenol, Trichoderma asperellum (e.g.,strain T34), Trichoderma gamsii, Trichoderma harzianum, trifloxystrobin, triflumazole, triforine, triphenyltin hydroxide, triticonazole, urea, Urocladium oudemansii (e.g., strain U3), vinclozolin, wanilazine, xylenol, zineb, ziram, zoxamid, and combinations thereof.

[0223] In some embodiments, one or more ascarosides are combined with one or more commercially available antimicrobial agents (e.g., one or more fungicides). In some embodiments, such commercially available antimicrobial agents are fungicidal mixtures. Commercially available antimicrobial agents are known in the art and include, but are not limited to (Syngenta), containing azoxystrobin; (Bayer Crop Science), containing tebuconazole and trifloxystrobin; (Syngenta), containing difenoconazole and fludioxonil; (Syngenta), containing acibenzolar-S-methyl; (Bayer Crop Science), containing tebuconazole and trifloxystrobin; (Bayer Crop Science), containing aluminum tris(O-ethylphosphonate); (Syngenta), containing cyproconazole; (Syngenta), which contains thiabendazole; (Syngenta), containing azoxystrobin and difenoconazole; (DuPont TM ), containing picoxystrobin and cyproconazole; (Syngenta), containing benzovinflumizone (alone or in combination with propiconazole or difenoconazole); ARCHIVE (Syngenta), containing fludioxonil and azoxystrobin; Contains pyraclostrobin; (Syngenta), containing fludioxonil; (BASF), containing metconazole; (Syngenta), containing fludioxonil and propiconazole; (Nufarm), containing copper hydroxide and metallic copper equivalents; (Bayer Crop Science), containing trifloxystrobin and prothioconazole; (Syngenta), containing azoxystrobin and benzovinfluazide; (BASF), containing methoxyacrylate; (Bayer Crop Science), containing trifloxystrobin; (Corteva), which contains penthiopyrad; (Syngenta), containing fludioxonil (alone or in combination with azoxystrobin); (BASF), (Syngenta), which contains difenoconazole (alone or in combination with cyprodinil or propiconazole); (Bayer Crop Science), containing fluopyram and pyrimethanil; (Syngenta), which contains propiconazole; (Syngenta), which contains thiabendazole; (Bayer Crop Science), containing Bacillus subtilis strain QST 713; (Syngenta), containing pentocyclamide (alone or in combination with difenoconazole or propiconazole or fludioxonil or azoxystrobin and propiconazole), (Syngenta), which contains fluazinam; (Syngenta), containing fluthiapiprolin (alone or in combination with metalaxyl-M or thiophanate-methyl or mandipropamid); (Bayer Crop Science), containing propamocarb hydrochloride; Contains pyraclostrobin and boscalid; (Bayer Crop Science), containing prothioconazole; (Bayer Crop Science), containing fluopyram and prothioconazole; (Bayer Crop Science), containing prothioconazole and tebuconazole; (Baye r Crop Science), containing prothioconazole and tebuconazole; (Syngenta), containing azoxystrobin (alone or in combination with chlorothalonil, metalaxyl-M, or difenoconazole); (Syngenta), containing azoxystrobin and propiconazole; (Marrone BioInn ovations), containing Sakhalin Knotweed; (Syngenta), containing mandipropamid (alone or in combination with difenoconazole); (Syngenta), containing metalaxyl-M (alone or in combination with chlorothalonil, copper hydroxide or mancozeb), (Bayer Cro p Science), containing pyrimethanil and 1,2-propylene glycol; (Syngenta), containing fludioxonil; (Bayer Crop Science), containing Bacillus subtilis strain QST 713; (Bayer Crop Science), containing propiconazole and trifloxystrobin; (Syngenta), containing azoxystrobin, fludioxonil, and difenoconazole; (Syngenta), containing cyprodinil and fludioxonil; (DuPont TM ), containing famoxadone and cymoxanil; (Syngenta), containing propiconazole (alone or in combination with thiophanate-methyl); (Syngenta), which contains difenoconazole; (Syngenta), which contains propiconazole, azoxystrobin, and benzovinfluazide; (Sy ngenta), containing azoxystrobin and metalaxyl-M; (Syngenta), containing cyprodinil; (Bayer CropScience), containing fluopyram; (Syngenta), containing pentocyclanil, metalaxyl-M, and fludioxonil, as well as thiabendazole or azoxystrobin; (DuPont TM ), including Vaseline; and (BASF), contains formamide.

[0224] Certain non-limiting active combinations of ascarosides and specific types of additional active agents for use in various embodiments of the present disclosure are described in more detail below.

[0225] Ascaroside + triazole fungicide

[0226] In some embodiments, the present disclosure provides compositions and methods involving ascarosides and triazoles (e.g., prothioconazole, tebuconazole, or a fungicide with the same mode of action as prothioconazole or tebuconazole). In some embodiments, ascarosides can be used with any triazole fungicide or any fungicide that inhibits the CYP51A1 enzyme. The CYP51A1 enzyme is required for the biosynthesis of ergosterol, a key component in fungal cell membranes. Using a fungicide with at least one ascaroside enhances the activity of the fungicide, thereby requiring a smaller amount of the fungicide.

[0227] Triazole fungicides include, but are not limited to, myclobutanil, epoxiconazole, phyconazole, metconazole, Uniconazole-P, Uniconazole, trichlorfonazole, tricyclazole, leaf rust, triadimenol, triadimefon, tetrafluconazole, tebuconazole, silfenazole, clofenac, prothioconazole, propiconazole, penconazole, imidazole, hexaconazole, furconazole, furoconazole, flutotriazole, flusilazole, fluquinconazole, trifloxybendazole, nitrobenzazole, ethiconazole, high-efficiency diniconazole, diniconazole, difenoconazole, benzyltriadimenol, cyproconazole, branconazole, bifenthrinol, azaconazole and indazolesulfamide. In a specific embodiment, the triazole fungicide is prothioconazole or tebuconazole. Also contemplated are mixtures of fungicides, especially fungicides used in combination with prothioconazole, tebuconazole or other triazoles. Such fungicides used in combination with prothioconazole include, but are not limited to, azoxystrobin, boscalid, tebuconazole, trifloxystrobin, fluopyram, azoxystrobin, and benzovinflumazole, etc. Such fungicides used in combination with tebuconazole include, but are not limited to, azoxystrobin, boscalid, prothioconazole, trifloxystrobin, fluopyram, azoxystrobin, and benzovinflumazole, etc.

[0228] Prothioconazole (IUPAC: (RS)-2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-1,2,4-triazole-3-thione) is a synthetic chemical produced primarily for its fungicidal properties. Prothioconazole is a systemic, broad-spectrum fungicide in the triazolinithione chemical class. It is a member of the triazole class of compounds, which has a unique toxicity group among this class of fungicides. Its potent fungicidal properties can be attributed to its ability to inhibit CYP51A1. This enzyme is required for the biosynthesis of ergosterol, a key component in fungal cell membranes. Prothioconazole is a fungicide used to control diseases caused by ascomycetes, basidiomycetes, and imperfect fungi. Prothioconazole is usually applied alone or in a tank mix with other agents such as fungicides, insecticides, herbicides, or other crop pesticides. Although any source of prothioconazole can be used, prothioconazole is sold under various trade names including Co-Op Pivot, Nufarm Propiconazole, Princeton, Fitness, Pivot 418EC, Quilt, Topnotch, Trivapro, Proline, Cotegra, Prosaro 250EC, Prosaro XTR, Delaro 325SC, Propulse, and Timor 240EC.

[0229] Prothioconazole is usually formulated as a 4 lb / gal suspension concentrate (equivalent to a flowable concentrate; FIC) formulation ( 480SC fungicide, 41% active ingredient). The product can be used as a post-sowing foliar spray or soil spray (applied to the soil of peanuts) by ground or aerial equipment at 0.088-0.178 lb ai / A / application (0.100-0.200 kg ai / ha / application). The recommended maximum season application rate range is 0.285-0.713 lb ai / A (0.320-0.800 kg ai / ha), and the recommended re-treatment interval is 5-21 days. Use of prothioconazole with at least one ascaroside according to the present disclosure can increase the activity of the fungicide, making it more effective in reducing disease severity and controlling disease. Therefore, lower concentrations or application rates of prothioconazole are needed.

[0230] Tebuconazole (IUPAC: 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-ylmethyl)pentan-3-ol) is a systemic fungicide and has both curative and preventive effects on diseased plants. Tebuconazole is used in a number of different popular fungicide products to control fungi, bacteria and viruses that affect plants. Tebuconazole is a fungicide known as a DMI (demethylation inhibitory fungicide) that inhibits spore germination and fungal growth by affecting the cell wall of the fungus. It also interferes with the production of ergosterol, a molecule that is essential for fungal formation. As a result, fungal formation is slowed down and eventually stopped. Due to this unique mode of action, tebuconazole has a fungistatic or growth-inhibiting effect rather than a fungicidal or fungicide effect. Tebuconazole is a flexible fungicide that has both curative and preventive effects on fungi. It acts systemically and is absorbed into the target plant to protect it from the disease, prevent further spread, or completely eliminate the disease depending on the severity level. Some common fungal and disease problems that tebuconazole is known to treat include rust, sheath blight, leaf spot, and anthracnose. Tebuconazole can also be used on turfgrass and ornamental plants to control a variety of fungal diseases, including but not limited to brown leaf spot, gray leaf spot, and powdery mildew.

[0231] Tebuconazole is applied at a rate of 4–10 fluid ounces per acre. Spray volumes can range from about 5 gallons to as much as 300 gallons per acre, depending on the equipment, plant species, and plant growth stage at the time of application. However, if too much of the triazole active ingredient is absorbed by the plant, it can cause phytotoxicity, poisoning the plant. Some plants are sensitive to triazole active ingredients. Therefore, using tebuconazole with ascarosides provided in accordance with the present disclosure can reduce or prevent phytotoxicity, as less tebuconazole is needed to achieve comparable results.

[0232] In certain embodiments, the present disclosure provides a blend of a triazole fungicide and an ascaroside, wherein the weight ratio of the triazole fungicide to the ascaroside is greater than 1000: 1. In certain embodiments, the present disclosure provides a blend of a triazole fungicide and an ascaroside, wherein the weight ratio of the triazole fungicide to the ascaroside is greater than 1500: 1, greater than 2000: 1, greater than 3000: 1, greater than 5000: 1, greater than 7500: 1, or greater than 10,000: 1.

[0233] In certain embodiments, the disclosure provides a blend of a triazole fungicide and an ascaroside, the blend being characterized in that the blended product is labeled for application to crops at a rate lower than the labeled dosage rate of the triazole fungicide alone. In certain embodiments, the blend is characterized in that the minimum labeled application rate is less than 4 ounces of triazole fungicide per acre, less than 3 ounces per acre, less than 2.5 ounces, less than 2 ounces, or less than 1 ounce of triazole fungicide per acre. In certain embodiments, such blends are characterized in that they are more effective in reducing fungal diseases of the crops to which they are applied than a single triazole fungicide applied at the full labeled dosage rate (e.g., 4-10 ounces per acre).

[0234] In certain embodiments, the present disclosure provides a blend of tebuconazole and ascarosides, wherein the weight ratio of tebuconazole to ascarosides is greater than 1000: 1. In certain embodiments, the present disclosure provides a blend of tebuconazole and ascarosides, wherein the weight ratio of tebuconazole to ascarosides is greater than 1500: 1, greater than 2000: 1, greater than 3000: 1, greater than 5000: 1, greater than 7500: 1, or greater than 10,000: 1.

[0235] In certain embodiments, the disclosure provides blends of tebuconazole and ascarosides, the blends being characterized in that the blended product is labeled for application to crops at a rate lower than the labeled dosage rate of tebuconazole alone. In certain embodiments, the blends are characterized in that the minimum labeled application rate is less than 4 ounces of tebuconazole per acre, less than 3 ounces per acre, less than 2.5 ounces, less than 2 ounces, or less than 1 ounce of tebuconazole per acre. In certain embodiments, such blends are characterized in that they are more effective in reducing fungal diseases of crops to which they are applied than tebuconazole alone applied at the full labeled dosage rate (e.g., 4-10 ounces per acre).

[0236] In certain embodiments, the present disclosure provides a blend of prothioconazole and ascarosides, wherein the weight ratio of prothioconazole to ascarosides is greater than 1000: 1. In certain embodiments, the present disclosure provides a blend of prothioconazole and ascarosides, wherein the weight ratio of prothioconazole to ascarosides is greater than 1500: 1, greater than 2000: 1, greater than 3000: 1, greater than 5000: 1, greater than 7500: 1, or greater than 10,000: 1.

[0237] In certain embodiments, the disclosure provides a blend of prothioconazole and ascaroside, the blend being characterized in that the blended product is labeled for application to crops at a rate lower than the labeled dosage rate of prothioconazole alone. In certain embodiments, the blend is characterized in that the minimum labeled application rate is less than 4 ounces of prothioconazole per acre, less than 3 ounces per acre, less than 2.5 ounces, less than 2 ounces, or less than 1 ounce of prothioconazole. In certain embodiments, such blends are characterized in that they are more effective in reducing fungal diseases of applied crops than prothioconazole alone applied at the full labeled dosage rate (e.g., 4-10 ounces per acre).

[0238] In certain embodiments, the present disclosure provides a blend of propiconazole and ascarosides, wherein the weight ratio of propiconazole to ascarosides is greater than 1000: 1. In certain embodiments, the present disclosure provides a blend of propiconazole and ascarosides, wherein the weight ratio of propiconazole to ascarosides is greater than 1500: 1, greater than 2000: 1, greater than 3000: 1, greater than 5000: 1, greater than 7500: 1, or greater than 10,000: 1.

[0239] In certain embodiments, the disclosure provides blends of propiconazole and ascarosides, the blends being characterized in that the blended product is labeled for application to crops at a rate lower than the labeled dosage rate of propiconazole alone. In certain embodiments, the blends are characterized in that the minimum labeled application rate is less than 4 ounces of propiconazole per acre, less than 3 ounces per acre, less than 2.5 ounces, less than 2 ounces, or less than 1 ounce of propiconazole per acre. In certain embodiments, such blends are characterized in that they are more effective in reducing fungal diseases of crops to which they are applied than propiconazole alone applied at the full labeled dosage rate (e.g., 4-10 ounces per acre).

[0240] Ascaroside + strobilurin fungicide

[0241] In some embodiments, the present disclosure provides compositions and methods involving ascarosides and strobilurins (e.g., azoxystrobin, kresoxim-methyl, picoxystrobin, pyraclostrobin, trifloxystrobin, famoxadone, or fenamidone). In some embodiments, ascarosides can be used with any strobilurin fungicide or any fungicide that inhibits mitochondrial respiration, or specifically, any fungicide that binds to the quinol binding site of the cytochrome complex (e.g., quinone exo-inhibitors or Q oI). In certain embodiments, ascarosides can be used with any strobilurin fungicide (e.g., with a member of the natural products collectively known as strobilurins, or with any substance known as a strobilurin fungicide, including synthetic analogs, derivatives, or mimetics of strobilurin natural products, or with a composition comprising a synthetic molecule having a structure or mode of action similar to strobilurins, including fenamidone and famoxadone). Using a fungicide with at least one ascaroside enhances the activity of the fungicide, thereby requiring a smaller amount of the fungicide. The fungicide used with the ascaroside can better control or prevent plant diseases, thereby promoting plant growth and yield. In addition, the activity of the ascaroside can be enhanced by applying it with a fungicide, thereby requiring less ascaroside.

[0242] According to the present disclosure, ascarosides can be combined with Q o I fungicides (especially strobilurins) are used in combination to enhance fungicidal activity. Q o I fungicides include, but are not limited to, strobilurins, azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, enoxastrobin, diastereamine, fluoxastrobin, fenoxystrobin, tosoxastrobin, pyraclostrobin, pyraclostrobin, kresoxim-methyl, fenamidone and famoxadone.

[0243] As discussed above, strobilurins or fungicides having the same mode of action as strobilurins may be used in the practice of the present invention. Also contemplated are fungicide mixtures, particularly fungicides used in combination with strobilurins. Such fungicides for use with strobilurins include, but are not limited to, boscalid, tebuconazole, propiconazole, myclobutanil, fluconazole, ipiconazole, metconazole, succinimide, succinimide, triadimefon, tetrafluconazole, tebuconazole, silifluazole, clofenac, prothioconazole, propiconazole, penconazole, imipenem, hexaconazole, furconazole, furoconazole, flutoconazole, flusilazole, fluquinconazole, trifluconazole, trifloxybacillus, fenbuconazole, ethoconazole, high-efficiency diniconazole, diniconazole, difenoconazole, benzyltriadol, cyproconazole, branconazole, bifenthrin, azaconazole, indazolesulfamide fluopyram, benzovintriadazole and the like.

[0244] Azoxystrobin (IUPAC: (E)-methyl 2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-methoxyprop-2-enoate) is a synthetic chemical primarily known for its fungicidal properties. Azoxystrobin is a xylem-mobile systemic fungicide with penetrant, protective and curative properties. It is a member of the strobilurin class of compounds. Azoxystrobin is active against a wide range of fungal plant pathogens including members of the phyla Ascomycota, Deuteromycota and Basidiomycota as well as oomycetes. Furthermore, its properties mean that it can move systemically through plant tissues to protect parts of the crop that have not come into contact with the spray. Important diseases it controls include leaf spot, rust, powdery mildew, downy mildew, web blotch and wilt. Azoxystrobin is registered worldwide for use on all important crops. Azoxystrobin is a thiocyanate derivative used in the treatment of wheat, barley, oats, rye, soybeans, cotton, rice, strawberries, peas, beans, onions and many other vegetables. Azoxystrobin can be used alone or in a bucket mix with other agents (such as fungicides, insecticides, herbicides or other crop agents). Although azoxystrobin from any source can be used, azoxystrobin is sold under various trade names, including Amistar, Abound, Heritage, Olympus, Ortiva, Priori Xtra, Scotts DiseaseEx, Haedes and Quadris. Suppliers and other brand names used in the U.S. are listed in the U.S. National Pesticide Information Retrieval System.

[0245] Azoxystrobin is typically formulated as a 2 lb / gal suspension concentrate formulation. Applications are made using ground or aerial equipment at 0.1-0.25 lb ai / A / application (0.100-0.200 kg ai / ha / application). The recommended maximum seasonal application rate range is 1.5 lb ai / A, and the recommended re-treatment interval is 14-21 days. Use of azoxystrobin with at least one ascaroside of the present invention can increase the activity of the fungicide, making it more effective in reducing the severity of disease and controlling disease. Therefore, lower concentrations or application rates of azoxystrobin are needed.

[0246] Picoxystrobin (IUPAC: (E)-3-methoxy-2-(2-(((6-(trifluoromethyl)pyridin-2-yl)oxy)methyl)phenyl)acrylate) is a systemic fungicide and has both curative and preventive effects on diseased plants. Picoxystrobin is a synthetic chemical produced primarily for its fungicidal properties. Picoxystrobin is a xylem-mobile systemic fungicide with penetrant, protective and curative properties. It is a member of the strobilurin class of compounds. Picoxystrobin is active against a wide range of fungal plant pathogens including members of the phyla Ascomycota, Deuteromycota and Basidiomycota as well as oomycetes. In addition, its properties mean that it can move systemically through plant tissues to protect parts of the crop not in contact with the spray. Important diseases it controls include leaf spot, rust, powdery mildew, downy mildew, web blotch and wilt. Picoxystrobin is currently registered in several countries, including: Argentina, Austria, Belgium, Brazil, Canada, Colombia, Czech Republic, Denmark, Estonia, Finland, France, Germany, Hungary, Ireland, Kenya, Latvia, Lithuania, Netherlands, New Zealand, Norway, Poland, Romania, Slovakia, South Africa, Sweden, the United States and the United Kingdom.

[0247] Picoxystrobin is sold as a single ingredient fungicide and in several mixtures with other fungicides, including: cyproconazole (Furlong, Stinger, and Aproach Prima); thiophanate-methyl (Credo and Plinker); and cyprodinil (Acanto Prima). Picoxystrobin can be applied alone or tank mixed with other agents such as fungicides, insecticides, herbicides, or other crop agents. Although any source of picoxystrobin can be used, it is sold under various trade names, including Aproach, Acapela, Cerefit, and Prima. Suppliers and other brand names used in the United States are listed in the National Pesticide Information Retrieval System.

[0248] Picoxystrobin is typically supplied as a solution concentrate (SC) formulated for application at an application rate of 0.05 to 0.2 lb AI per acre. Spray volumes may range from about 5 gallons to as much as 300 gallons per acre, depending on the equipment, plant species, and plant growth stage at the time of application. Use of picoxystrobin with at least one ascaroside of the present invention in various ways as outlined herein can increase the activity of the fungicide, making it more effective in reducing the severity of disease and controlling disease. Therefore, lower concentrations or application rates of azoxystrobin are desired.

[0249] In certain embodiments, the present disclosure provides a blend of a strobilurin fungicide and an ascaroside, wherein the weight ratio of the strobilurin fungicide to the ascaroside is greater than 1000: 1. In certain embodiments, the present disclosure provides a blend of a strobilurin fungicide and an ascaroside, wherein the weight ratio of the strobilurin fungicide to the ascaroside is greater than 1500: 1, greater than 2000: 1, greater than 3000: 1, greater than 5000: 1, greater than 7500: 1, or greater than 10,000: 1.

[0250] In certain embodiments, the present disclosure provides blends of strobilurin fungicides and ascarosides, the blends being characterized in that the blended product is labeled for application to crops at a rate lower than the labeled dosage rate of the strobilurin fungicide alone. In certain embodiments, the blends are characterized in that the minimum labeled application rate is less than 4 ounces of strobilurin fungicide per acre, less than 3 ounces, less than 2.5 ounces, less than 2 ounces, or less than 1 ounce of strobilurin fungicide per acre. In certain embodiments, such blends are characterized in that they are more effective in reducing fungal diseases of the crops to which they are applied than a single strobilurin fungicide applied at the full labeled dosage rate (e.g., 4-10 ounces per acre).

[0251] In certain embodiments, the present disclosure provides a blend of azoxystrobin and ascarosides, wherein the weight ratio of azoxystrobin to ascarosides is greater than 1000: 1. In certain embodiments, the present disclosure provides a blend of azoxystrobin and ascarosides, wherein the weight ratio of azoxystrobin to ascarosides is greater than 1500: 1, greater than 2000: 1, greater than 3000: 1, greater than 5000: 1, greater than 7500: 1, or greater than 10,000: 1.

[0252] In certain embodiments, the disclosure provides a blend of azoxystrobin and ascaroside, the blend being characterized in that the blended product is labeled as being applied to crops at a rate lower than the labeled dosage rate of azoxystrobin alone. In certain embodiments, the blend is characterized in that the minimum labeled application rate is less than 4 ounces of azoxystrobin per acre, less than 3 ounces per acre. Less than 2.5 ounces, less than 2 ounces, or less than 1 ounce of azoxystrobin. In certain embodiments, such blends are characterized in that they are more effective than azoxystrobin alone applied at the full labeled dosage rate (e.g., 4-10 ounces per acre) in reducing fungal diseases of applied crops.

[0253] Ascaroside + SDHI fungicide

[0254] In some embodiments, the present disclosure provides compositions and methods involving ascarosides and succinate dehydrogenase inhibitors (SDHI) fungicides. Succinate dehydrogenase (SDH) complex II is considered to be an important component of the fungal mitochondrial respiratory chain. The SDH enzyme transfers succinate-derived electrons directly to the ubiquinone pool of the respiratory chain, promoting energy transfer in the mitochondria. Succinate dehydrogenase inhibitors (SDHIs) are a class of fungicides that act on mitochondrial SDH complex II, blocking cellular energy transfer, thereby inhibiting the development of fungi. Many SDHIs inhibit fungal respiration by blocking the ubiquinone binding (Qp) site. SDHIs tightly bound to the Qp site can physically block access to the ubiquinone substrate, thereby preventing further circulation of succinate oxidation.

[0255] SDHI fungicides include, but are not limited to, benzamide fungicides that inhibit succinate dehydrogenase (SDH) complex II. Examples of benzamide SDHI fungicides include, but are not limited to, benodanil, flufenoxadiazam, flutolanil, mebenil, mepronil, salicylanilide, fluopyram, benzohydroxamic acid, flumetover, fluopicolid e, fluopimomide, tioxymid, trichlamide, zarilamid, and zoxamide. SDHI fungicides also include formamide fungicides that inhibit succinate dehydrogenase (SDH) complex II. The carboxamide fungicides that inhibit SDH include, but are not limited to, oxathiin fungicides, furancarboxamide fungicides, pyrazinecarboxamide fungicides, pyrazolecarboxamide fungicides, and pyridinecarboxamide fungicides. Examples of oxathiin fungicides include, but are not limited to, carboxin and oxycarboxin. Examples of furancarboxamide fungicides include, but are not limited to, furamide, dimethylfuranamide, or furazolidone. An example of a pyrazinecarboxamide fungicide is bifenthionil. Examples of pyrazole carboxamide fungicides include, but are not limited to, benzovindiflupyr, bixafen, flubeneteram, fluindapyr, fluxapyroxad, furametpyr, inpyrfluxam, isoflucypram, isopyrazam, penflufen, penthiopyrad, pydiflumetofen, pyrapropoyne, sedaxane, ethaboxam, and thifluzamide. Examples of pyridine carboxamide fungicides include, but are not limited to, boscalid or triflupyramide. SDHI fungicides also include the thiopheneamide fungicides which inhibit SDH Complex II, for example, isoflurane.

[0256] In certain embodiments, the present disclosure provides blends of SDHI fungicides and ascarosides, wherein the weight ratio of SDHI fungicides to ascarosides is greater than 1000: 1. In certain embodiments, the present disclosure provides blends of SDHI fungicides and ascarosides, wherein the weight ratio of SDHI fungicides to ascarosides is greater than 1500: 1, greater than 2000: 1, greater than 3000: 1, greater than 5000: 1, greater than 7500: 1, or greater than 10,000: 1.

[0257] In certain embodiments, the disclosure provides blends of tebuconazole and ascarosides characterized in that the blended product is labeled for application to crops at a rate lower than the labeled dosage rate of the SDHI fungicide alone. In certain embodiments, the blend is characterized in that the minimum labeled application rate is less than 4 ounces of SDHI fungicide per acre, less than 3 ounces, less than 2.5 ounces, less than 2 ounces, or less than 1 ounce of SDHI fungicide per acre. In certain embodiments, such blends are characterized in that they are more effective in reducing fungal diseases of the crops to which they are applied than a single SDHI fungicide applied at the full labeled dosage rate (e.g., 4-10 ounces per acre).

[0258] Multi-component blends

[0259] In certain embodiments, the present disclosure provides blends and / or products containing one or more ascarosides and at least two additional active agents for co-application to crops. In certain embodiments, such products comprise blends of ascarosides and two or more chemical fungicides. In certain embodiments, the two or more chemical fungicides are from the same chemical class (e.g., two different triazoles as in Example 4 below). In certain embodiments, the two or more chemical fungicides are from different chemical classes (e.g., a triazole and strobilurin as in Examples 2 and 8 below; or a triazole and SDHI as in Example 6).

[0260] In certain embodiments, the present disclosure provides blends and / or products containing one or more ascarosides and two or more different triazole fungicides (e.g., such as the triazole fungicides described in more detail above) for co-application to crops. In certain embodiments, the present disclosure provides blends and / or products containing one or more ascarosides and two or more different strobilurin fungicides (e.g., such as the strobilurin fungicides described in more detail above) for co-application to crops. In certain embodiments, the present disclosure provides blends and / or products containing one or more ascarosides and two or more different SDHI fungicides (e.g., such as the SDHI fungicides described in more detail above) for co-application to crops. In certain embodiments, the present disclosure provides blends and / or products containing one or more ascarosides, at least one triazole fungicide, and at least one strobilurin fungicide for co-application to crops. In certain embodiments, the present disclosure provides blends and / or products containing one or more ascarosides, at least one triazole fungicide, and at least one SDHI fungicide for co-application to crops. In certain embodiments, the present disclosure provides blends and / or products containing one or more ascarosides, at least one strobilurin fungicide, and at least one SDHI fungicide for co-application to crops.

[0261] In certain embodiments, the present disclosure provides blends and / or products for co-application to crops containing one or more ascarosides and at least two different chemical fungicides, characterized in that the weight ratio of chemical fungicides to ascarosides is greater than 1000: 1. In certain embodiments, the present disclosure provides blends and / or products for co-application to crops containing one or more ascarosides and at least two different chemical fungicides, wherein the weight ratio of chemical fungicides to ascarosides is greater than 1500: 1, greater than 2000: 1, greater than 3000: 1, greater than 5000: 1, greater than 7500: 1, greater than 10,000: 1, greater than 20,000: 1, or greater than 30,000: 1.

[0262] In certain embodiments, the present disclosure provides blends and / or products containing one or more ascarosides and at least two different chemical fungicides for co-application to crops, the blends and / or products being characterized in that the blended product is labeled for application to the crop at a rate that is lower than the labeled dosage rate of the chemical fungicide that does not contain an ascaroside.

[0263] Uses and compositions

[0264] As described above, the disclosed treatments using ascarosides and additional active agents (e.g., including but not limited to the triazole, strobilurin or SDHI fungicides described in detail above) can be used to significantly reduce disease, promote plant growth and / or yield, and reduce dependence on traditional pesticides. The term "treat" or "treating" or its derivatives include substantially inhibiting, slowing or reversing the progression of a condition, substantially ameliorating the symptoms of a condition, or substantially preventing the appearance of symptoms or conditions caused by one or more pathogens (e.g., fungal pathogens). The terms "control" and "protecting plants from pathogens" refer to inhibiting or reducing one or more of the growth, germination, reproduction and / or proliferation of the target pathogen; and / or killing, removing, destroying or reducing the appearance and / or activity of the target pathogen. Thus, plants treated according to the present disclosure may have reduced disease severity or reduced disease development in the presence of statistically significant amounts of plant pathogens. The term "prevent" and its variants refer to controlling a disease state prior to fungal or bacterial proliferation or infection. In this case, the composition is applied prior to exposure to the pathogen. The term "inhibit" and all variations thereof are intended to cover limiting or inhibiting the growth of fungi or pests.

[0265] In some embodiments, treatment with an ascaroside and an additional active agent provides an additive effect and / or exceeds an additive effect and / or a synergistic effect. It is understood by those skilled in the art that synergy occurs when the combined effect of two or more active agents is greater than the sum of the individual effects of the active agents. Thus, in the context of the present disclosure, synergy is manifested as the combined effect of an ascaroside and an additional active agent exhibiting a greater effect (e.g., in terms of greater antiparasitic activity, more extensive antiparasitic activity, increased yield, etc.) than the individual effect of the ascaroside plus the individual effect of the additional active agent. In some embodiments, treatment with an ascaroside and an additional agent can produce results that are expected to be better than treatment with only a single active agent (e.g., an ascaroside and an additional active agent) alone. Thus, plants or plant parts treated with an effective amount of the components described herein can show reduced disease severity, or reduced disease development, in the presence of a statistically significant amount of a plant pathogen. Compared with untreated control plants, the disease severity reduction or disease development reduction can be reduced by about 30% to about 40%, to about 50%, to about 60%, to about 70%, to about 80%, to about 90% or to about 100%. In other cases, compared with untreated control plants, plants treated with an activating agent (e.g., fungicide) provided herein can show at least about 25%, at least about 40%, at least about 50%, at least about 51%, about 60%, about 70%, about 80%, about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, about 99% or about 100% disease severity reduction or disease development reduction in the presence of plant pathogens.

[0266] In some embodiments, treatment with an ascaroside as provided herein and an additional active agent provides a broader spectrum of antiparasitic activity (eg, control of several diseases occurring simultaneously in a given crop).

[0267] In some embodiments, treatment with ascarosides and additional active agents as provided herein can reduce the amount of additional active agents required to achieve comparable results to those seen without the addition of ascarosides. For example, less additional active ingredients (e.g., fungicides or fungicide mixtures) or less ascarosides may be required to achieve beneficial results and control pathogens (e.g., fungal pathogens), or less spraying may be required during the growing season. In some embodiments, the amount of active agent (e.g., fungicide) required to prevent or treat plant diseases can be reduced by about 5%, about 10%, about 20%, about 30%, about 40%, about 50%, about 60%, about 70%, about 90% or more. In some embodiments, for the pathogen, the ratio of the active agent (e.g., fungicide) applied is about 1 / 4X or about 1 / 4X the labeled field use rate, about 1 / 3X or about 1 / 3X the labeled field use rate, or about 1 / 2X or about 1 / 2X the labeled field use rate. Likewise, the amount of the ascaroside composition can also be reduced. The ascaroside can be reduced by about 5%, about 10%, about 20%, about 30%, about 40%, about 50%, about 60%, about 70%, about 90% or more.

[0268] In some embodiments, treatment with the ascarosides provided herein and an additional active agent can provide additional benefits, for example, increasing the health, growth and / or yield of a plant. An increase in yield can include any statistically significant increase, including but not limited to an increase of at least 1%, an increase of at least 3%, an increase of at least 5%, an increase of at least 10%, an increase of at least 20%, an increase of at least 30%, an increase of at least 50%, an increase of at least 70%, an increase of at least 100%, or more, compared to a plant not exposed to the two components.

[0269] One or more ascarosides and one or more additional active agents (e.g., including but not limited to triazoles, strobilurins, and SDHI, as described in detail above) are typically applied in an effective amount. An effective amount is an amount sufficient to control, treat, prevent, or inhibit plant pathogens, and / or reduce plant disease severity or reduce plant disease development. By controlling plant diseases, an effective amount can improve the agronomic traits of interest and promote and increase plant health, growth, and yield. One or more ascarosides and one or more active agents can be applied to plants in a variety of ways. In some embodiments, one or more ascarosides and one or more additional active agents are co-applied in separate formulations / agricultural compositions (e.g., such that both the one or more ascarosides and the one or more additional active agents are applied within a given time period of each other), or co-applied in the same formulation / agricultural composition.

[0270] In some embodiments, co-administration can involve administering two separate formulations (one comprising one or more ascarosides and the other comprising one or more additional active agents) at close time points, e.g., substantially simultaneously or within about 1 minute, within about 5 minutes, within about 10 minutes, within about 30 minutes, within about one hour, within about 4 hours, within about 6 hours, within about 12 hours, within about 24 hours, or within about 2 days of each other. When the one or more ascarosides and the additional active agent are administered separately, the one or more ascarosides can be administered before or after administration of the additional active agent.

[0271] In some embodiments, co-application can involve applying one or more ascarosides and one or more additional active agents in combination to the plant shortly before application (e.g., immediately prior to application). A suitable method for applying one or more ascarosides and one or more additional active agents is to mix the components in situ; for example, one or more ascarosides can be added to a fully formulated tank mix comprising one or more additional active agents.

[0272] In other embodiments, the components to be co-applied can be combined together at a time point prior to application. In these embodiments, an agricultural formulation is prepared that includes one or more ascarosides and one or more additional active agents and one or more inert ingredients. Advantageously, in some embodiments, provided herein are combinations of one or more ascarosides and one or more additional active agents that are compatible with each other, and the resulting formulations can exhibit long-term stability (e.g., one week or more, one month or more, two months or more, three months or more, four months or more, five months or more, six months or more), for example, under standard conditions (e.g., room temperature and contained in a closed system in one or more relative humidity regions). The display of stability in this context can vary. For example, in some embodiments, no obvious separation is observed with the naked eye. In some embodiments, no significant changes in the amount of active ingredients and / or ascarosides are observed by conventional methods (e.g., spectroscopy). In some embodiments, no significant chemical degradation of the active ingredients and / or ascarosides is observed using conventional methods (e.g., spectroscopy).

[0273] Such formulations comprising both one or more ascarosides and one or more additional active agents may vary in composition and form. In some embodiments, such formulations are in solid form, while in some embodiments, such formulations are in liquid form. As described above, in addition to one or more ascarosides and one or more additional active agents, the formulations typically include one or more inert ingredients, for example, one or more agronomically acceptable carriers (also referred to as agriculturally acceptable or suitable adjuvants). It is preferred to use non-toxic carriers in the formulations and methods of the present disclosure. The term "agronomically acceptable carrier" includes any carrier suitable for application to plants or soil, for example, conventional excipients in formulation technology, such as for forming solutions (e.g., solutions that can be directly sprayed or directly diluted), emulsions (e.g., emulsion concentrates and dilute emulsions), wettable powders, suspensions, soluble powders, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, polymeric material encapsulating agents, coatable pastes, natural and synthetic materials impregnated with active compounds, and microcapsules in polymeric substances. In some embodiments, agriculturally acceptable carriers may include surfactants, emulsifiers, oils, salts, and the like.

[0274] These compositions can be produced in a known manner, for example, by mixing one or more ascarosides and one or more additional active agents with one or more agronomically acceptable carriers, such as liquid solvents or solid carriers, optionally with additional components including, but not limited to, surfactants, including emulsifiers, dispersants, foam formers, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, ultraviolet radiation absorbers, weathering stabilizers, plasticizers, release agents, fragrances, thermal insulation additives (e.g., silica), crosslinking agents, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, extenders / stickers, tackifiers, plant penetrants, safeners, spreaders, and wetting agents, etc. In some embodiments, such formulations may include one or more additional active agents and / or one or more plant or plant product treatment compounds. In addition, some compositions will have a residue because they are not easily washed away from the leaves of the plant when it rains, and thus can protect from pests during and after rainy days. The additional components mentioned herein can be added directly to the above-mentioned formulations, or can be added separately, for example, at the time of application. In some embodiments, wetting agents, emulsifiers, spreaders, etc. are used in the formulations. The formulations include concentrated forms in which the active agent is present in a concentration of 0.001% to 98.0%, and the remaining contents are agriculturally acceptable carriers / adjuvants.

[0275] Such formulations, especially those containing less than 50% of the compounds of the invention, can sometimes be used directly, but these formulations can also be diluted with other agriculturally acceptable carriers to form more diluted treatment formulations. These latter formulations can contain low concentrations (0.001% to 0.1%) of the compounds described herein.

[0276] The formulation may also contain "co-surfactants" to enhance deposition, wetting and penetration of the compound on target crops and organisms. These "co-surfactants" may optionally be used as a component or tank mix of the formulation. The amount of the co-surfactant is typically 0.01% to 1.0% by volume, preferably 0.05% to 0.5% by volume, based on the spray volume of water. Suitable auxiliary surfactants include, but are not limited to, ethoxylated nonylphenol, ethoxylated synthetic alcohol or natural alcohol, ester or salt of sulfosuccinic acid, ethoxylated silicone, ethoxylated fatty amine, blends of surfactants with mineral oil or vegetable oil, crop oil concentrate (mineral oil (85%) + emulsifier (15%)); nonylphenol ethoxylate; benzyl coconut oil alkyl dimethyl quaternary ammonium salt; blends of petroleum hydrocarbons, alkyl esters, organic acids and anionic surfactants; C9-Cu alkyl polyglycosides; phosphated alcohol ethoxylates; natural primary alcohol (C12-C16) ethoxylates; di-sec-butylphenol EO-PO block copolymers; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecanol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15EO); PEG (400) dioleate-99. The formulation may also include an oil-in-water emulsion. If the agronomically acceptable carrier is water, then in certain embodiments, an organic solvent as an auxiliary liquid solvent may be added. Suitable liquid solvents include, for example, aromatic compounds (e.g., xylene, toluene, and alkylnaphthalene); chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons (e.g., chlorobenzene, vinyl chloride, and methylene chloride); aliphatic hydrocarbons (e.g., cyclohexane); paraffins (e.g., petroleum fractions, mineral oils, and vegetable oils); alcohols (e.g., butanol or ethylene glycol and their ethers and esters); ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone) and strong polar solvents (e.g., dimethylformamide and dimethyl sulfoxide). Other examples of organic solvents include, but are not limited to, xylene, propylbenzene fractions; or mixed naphthalene fractions, mineral oil, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkylamides of various fatty acids, in particular dimethylamides of fatty glycols and glycol derivatives, such as n-butyl ether, ethyl ether or methyl ether of diethylene glycol, methyl ether of triethylene glycol, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffin oil, etc.; terpene solvents, rosin derivatives, aliphatic ketones such as cyclohexanone, complex aliphatic alcohols and aromatic alcohols such as 2-ethoxyethanol, vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, etc.; esters of the above vegetable oils; and the like. A mixture of two or more organic liquids may also be used when preparing certain emulsifiable concentrates. The organic liquids include xylene and propylbenzene fractions, and in some cases, xylene is most preferred.Surface active dispersants are typically used in liquid formulations in amounts ranging from 0.1 wt % to 20 wt % based on the combined weight of the dispersant and the compound or compounds.

[0277] Suitable agronomically acceptable solid carriers include, for example, ammonium salts and ground natural minerals (e.g., kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth); ground synthetic minerals (e.g., highly dispersed silica, alumina and silicates); crushed and fractionated natural rocks (e.g., calcite, marble, pumice, sepiolite and dolomite); synthetic particles of inorganic and organic powders; particles of organic materials (e.g., sawdust, coconut shells, corn cobs and tobacco stems). In some embodiments, the dry composition may include powders, etc.

[0278] Suitable emulsifiers and foam forming agents include, for example, nonionic emulsifiers and anionic emulsifiers (for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example, alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates and aryl sulfonates) protein hydrolyzates. Suitable dispersants include, for example, lignin sulfite waste liquor and methylcellulose. Viscosifiers such as carboxymethyl cellulose and natural polymers and synthetic polymers in powder, particle or lattice form, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids, such as cephalin and lecithin and synthetic phospholipids, can be used for disclosed compositions. Examples of nonionic emulsifiers for preparing emulsifiable concentrates include polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxide, such as ethoxylated alkylphenols and carboxylic acid esters solubilized with polyols or polyoxyalkylenes. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include oil-soluble salts of alkyl aryl sulfonic acids (eg, calcium salts), oil-soluble salts of sulfated polyethylene glycol ethers, and appropriate salts of phosphated polyethylene glycol ethers. Other additives may include, for example, mineral oils and vegetable oils.

[0279] "Surfactants" (e.g., which may typically comprise from about 0.5% to about 10% of a wettable powder) include sulfonated lignin, condensed naphthalene sulfonates, naphthalene sulfonates, alkylbenzene sulfonates, alkyl sulfonates, or nonionic surfactants such as ethylene oxide adducts of alkylphenols, or mixtures thereof

[0280] Colorants such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts may also be included in the composition.

[0281] Methods for preparing solid and liquid compositions for agrochemicals are generally known and can be used according to the present disclosure (wherein such methods involve adding one or more ascarosides and one or more additional active agents to such compositions). In some embodiments, the composition can be used as a liquid concentrate, a ready-to-use (RTU) liquid spray, a dust or a solid, depending on the needs of the user. In some embodiments, the composition according to the present disclosure can be in the form of a granular material (including dust, granules, soluble powders, flowable powders, water-dispersible granules, etc.). In certain embodiments, the composition according to the present disclosure can be in the form of a liquid (e.g., a solution, a suspension or an emulsion). In some embodiments, the composition is in the form of a granular material treated with a liquid comprising one or more ascarosides and one or more additional active agents. In some embodiments, the composition comprising one or more ascarosides and one or more additional active agents is formed into fibers or filaments, and in some such embodiments, a woven or nonwoven textile (e.g., a film) can be produced from the fibers or filaments. In some embodiments, the composition is made into particles as provided herein. In some embodiments, the composition is in the form of a film as provided herein, for example, a plastic mulch. Any of the solid compositions provided herein may be optionally coated by methods well known in the art to delay the release of one or more ascaroside and one or more additional active agents. The formulation selected will depend on the intended use of the product.

[0282] Dusts containing compounds of the present disclosure can be prepared by thoroughly mixing one or more compounds in powder form with a suitable powdered agricultural carrier (e.g., kaolin, ground volcanic rock, etc.). Dusts can suitably contain from about 1% to about 10% by weight of the compound, based on the total weight of the dust.

[0283] Wettable powders can be agglomerated or compacted to form water-dispersible granules. These granules can include a mixture of a compound, an inert carrier suitable for granular application, and a surfactant. The concentration of the compound is generally about 0.1% to about 90% by weight. "Inert carriers suitable for granular application" are generally pyrophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, purified silicates, and the like. In these operations, the finely divided carrier and surfactant are generally blended and milled with the compound.

[0284] "Aqueous suspensions" can be prepared in which the compound is dispersed in an aqueous vehicle at a concentration generally ranging from about 5% to about 50% by weight. Suspensions can be prepared by grinding and vigorously mixing the compound into a vehicle of water, surfactants, and dispersants. Inert ingredients (such as inorganic salts and synthetic or natural gums) can also be used to increase the density and / or viscosity of the aqueous vehicle as desired.

[0285] The amount of the one or more ascarosides and the one or more active agents included in such formulations can vary. In certain specific embodiments, the amount of the one or more ascarosides and the one or more active agents is a synergistically effective amount. Typically, the formulation contains a lower weight percentage of the one or more ascarosides than the weight percentage of the one or more active agents.

[0286] In certain embodiments, the combinations provided are characterized in that the synergistic amount of one or more ascarosides as a percentage of the formulation is very low. In certain embodiments, the combinations provided are characterized in that the ascarosides are provided in an amount of less than 1% by weight relative to the other active ingredients. In certain embodiments, the combinations provided are characterized in that the ascarosides are provided in an amount of less than 0.1% by weight relative to the other active ingredients. In certain embodiments, the combinations provided are characterized in that the ascarosides are provided in an amount of less than 0.05% by weight relative to the other active ingredients. In certain embodiments, the combinations provided are characterized in that the ascarosides are provided in an amount of less than 0.01% by weight relative to the other active ingredients. In certain embodiments, the combinations provided are characterized in that the ascarosides are provided in an amount of less than 0.001% by weight relative to the other active ingredients.

[0287] In certain embodiments, the co-application of one or more ascarosides and one or more additional active agents as described herein can be used to treat living plants or plant parts, soil around plants, soil to be planted with seeds / seedlings, or plants or plant parts after harvest. As used herein, co-application includes simultaneous application or sequential application, and can refer to application in the same composition or in separate compositions, etc. In some embodiments, one or more ascarosides and one or more additional active agents are applied to a plant part, i.e., a part of a plant, such as one or more of a root, stem, leaf, seed, and / or flower. Such methods can be performed at any one or more stages of the plant life cycle, for example, from seed to seedling to growing plant to before harvest. In certain embodiments, co-application includes spraying one or more ascarosides and one or more additional active agents on plant leaves. In certain embodiments, co-application includes applying a powder or solid to the leaves of a plant. In certain embodiments, co-application includes treating the seeds of a plant (e.g., before planting) with one or more ascarosides and one or more additional active agents. In certain embodiments, co-application comprises treating the trunk, branches or stems of the plant with one or more ascarosides and one or more additional active agents. In certain embodiments, co-application comprises applying one or more ascarosides and one or more additional active agents to the soil in which the plant is growing or in which the plant will grow.

[0288] In some embodiments, the disclosed treatment methods can protect growing plants in the manner described in U.S. Pat. No. 10,136,595, which is incorporated herein by reference in its entirety. For example, such methods can enhance pathogen resistance and / or induce one or more plant defense responses (thereby inhibiting pathogen growth and / or infection) in (or near) plants to which one or more ascarosides and one or more additional active agents are applied. The disclosed methods can enhance resistance to pathogens including, but not limited to, oomycetes, bacteria, nematodes, viruses, and insects, such as, but not limited to, Pseudomonas syringae, Phytophthora infestans, Blepharitis graminis, Heterodera schachtii, Meloidogyne incognita, Meloidogyne hapla, and turnip crinkle virus.

[0289] The disclosed treatment methods can further enhance control of a range of plant pathogens (e.g., fungal pathogens). In some embodiments, such enhanced control can depend on the selection of one or more additional active agents. For example, by combining a given active agent with one or more ascarosides, the known activity of the active agent against certain pathogens in certain crops can be enhanced.

[0290] As a non-limiting example, the combination of ascarosides with triazole fungicides has shown enhanced efficacy against fungal pathogens such as Fusarium. Figure 1 Data from a field trial in which wheat was treated with Proline alone TM (a commercial formulation of the triazole fungicide prothioconazole) sprayed with (products based on ascaroside active ingredients) spraying, and PROLINE TM and The combination products showed evidence of synergy, with both disease control levels and wheat yield increases from the blend exceeding what would be expected from the simple additive effects of the two products.

[0291] The exact method of treating plants or soil with one or more ascarosides and one or more active agents is not particularly limited. Plants and / or soil can be treated in accordance with the present disclosure, for example, by soaking, spraying, evaporation, atomization, broadcasting, smearing, side application, or in-furrow application. For example, in certain embodiments, plants or soil can be sprayed with one or more suitable liquid compositions, solid plastic mulch compositions can be applied to the soil around the plants, and / or in-furrow application or side application of granular compositions can be provided. In some embodiments, the methods provided herein include treating seeds prior to planting.

[0292] The plant type that can be processed according to the method disclosed in the present invention is not particularly limited, and can be, for example, fruit and vegetable plants, trees and shrubs. The non-limiting examples of the plant that can be processed according to the disclosed method include, but are not limited to, the plant selected from the group consisting of the following: tobacco, Arabidopsis, tomato, barley, potato, sweet potato, yam, cotton, soybean, strawberry, beet, corn, rice, wheat, rye, oat, sorghum, millet, bean, pea, apple, banana, pear, cherry, peach, plum, apricot, almond, grape, kiwi, mango, melon, papaya, walnut, hazelnut, pistachio, raspberry, blackberry, loganberry, blueberry, cranberry, orange, lemon, grapefruit, tangerine, lettuce, carrot, onion, broccoli, cabbage, avocado, cocoa, cassava, cotton and flax.

[0293] In some embodiments, the compositions and methods provided herein can be used to protect any plant from fungal or bacterial diseases, and promote plant health, growth and yield, including but not limited to monocots and dicots. Examples of plant species of interest include but are not limited to corn (Zea mays), Brassica species (Brassicasp.) (e.g., B. napus, B. rapa, B. juncea) (especially those Brassica species that can be used as a source of seed oil), alfalfa (Medicago sativa), rice (Oryza sativa), rye (Secale cereale), sorghum (Sorghum bicolor, Sorghum vulgare), millet (e.g., Pennisetum glaucum, Panicum miliaceum), millet (Setaria italica), seeds (Eleusinecoracana), sunflower (Helianthus annuus), safflower (Carthamus tinctorius), wheat (Triticum aestivum), soybean (Glycine max), tobacco (Nicotiana tabacum), potato (Solanum tuberosum), peanut (Arachis hypogaea), cotton (Gossypium barbadense, Gossypium barbadense), sweet potato (Ipomoea batatus), cassava (Mani hot esculenta), coffee (Coffea spp.), coconut (Cocos nucifera), pineapple (Ananas comosus), orange (Citrus spp.), cocoa (Theobroma cacao), tea (Camellia sinensis), banana (Musa spp.), avocado (Perseaamericana), fig (Ficus casica), guava (Psidium guajava), mango (Mangiferaindica), olive (Olea europaea), papaya (Carica papaya), cashew (Anacardium occidentale), macadamia (Macadamia integrifolia), almond (Prunus amygdalus), sugar beet (Betavulgaris), sugar cane (Saccharum spp.), oats, barley, vegetables, ornamentals and conifers.

[0294] Vegetables include tomatoes (Lycopersicon esculentum), lettuce (e.g., Lactuca sativa), beans (Phaseolus vulgaris), butter beans (Phaseolus limensis), butter beans, green beans (Phaseolus vulgaris), cowpeas (Vigna unguiculata), pigeon peas (Cajanus cajan), yam bean, yam bean, peas (Ispp.), and members of the genera such as cucumber (C. sativus), cantaloupe (C. cantalupensis), and musk melon (C. melo). Ornamental plants include azaleas (Rhododendron spp.), hydrangeas (Macrophyllahydrangea), hibiscus (Hibiscus rosasanensis), roses (Rosa spp.), tulips (Tulipa spp.), daffodils (Narcissus spp.), petunias (Petunia hybrida), carnations (Dianthus caryophyllus), poinsettias (Euphorbia pulcherrima), and chrysanthemums.

[0295] Conifers that can be used to practice the present invention include, for example, pines such as loblolly pine (Pinus taeda), slash pine (Pinus elliotii), ponderosa pine (Pinus ponderosa), twisted pine (Pinus contorta), and radiata pine (Pinus radiata); Douglas fir (Pseudotsuga menziesii); western hemlock (Tsuga canadensis); Sitka spruce (Picea glauca); redwood (Sequoia sempervirens); true fir (Abies amabilis) and balsam fir (Abies balsamea); and cedar (Thuja plicata) and Alaska yellow cedar (Chamaecyparis nootkatensis). In a specific embodiment, the plant of the present invention is a crop plant (e.g., corn, alfalfa, sunflower, Brassica, soybean, cotton, safflower, peanut, sorghum, wheat, millet, tobacco, etc.). In other embodiments, corn or soybean plants are employed.

[0296] According to the present disclosure, diseases and infestations that can be effectively reduced by treatment with one or more ascarosides and one or more fungicides can affect any part of the plant (e.g., seeds, roots, stems, leaves, and spikes).

[0297] Fungal and bacterial pathogens that can be controlled with the disclosed combinations include, but are not limited to, those selected from the group consisting of: Botrytis cinerea, Cersospora spp., Cercospora sojina, Cerc ospora beticola, Cercospora canescens, Alternaria solani, Alternaria brassicae, Blumeria graminis f.sp. Tritici, Erysiphe necator, Podosphaera xanthii, Podosphaera leuco tricha, Golovinomyces cichoracearum, Erysiphe lagerstroemiae, Erysiphe cichoracearum), Erysiphe graminis, Sphaerotheca pannosa, Sphaerotheca fuliginea, Colletotrichum cereale, Apiognomonia errabunda, Apiognomonia veneta, Colletotrichum gloeosporiodes, Discula fraxinea, Plasmopara viticola, Pseudoperonospora cubensis, Peronospora belbahrii, Bremia lactucae, Peronosporalamii, Plasmopara obdusce ns, Pythium cryptoirregulare, Pythium aphanidermatum, Pythium irregulare), Pythium sylvaticum, Pythium myriotylum, Pythium ultimum, Phytophthora capsicicapsici), Phytophthora nicotianae, Phytophthora infestans, Phytophthora tropicalis, Phytophthora sojae, Fusarium graminearum, Fusarium solani, Fusarium oxysporum, Fusarium graminicola, Gibberella zeae, Colletotrichum graminicola, Phakopsora sp., Phako psora meibomiae, Phakopsora pachyrizi, Puccinia triticina, Puccinia recondita, Pucc inia striiformis, Puccinia graminis), Puccinia spp., Venturia inaequalis, Verticillium spp., Erwinia amylovora, Monilini a fructicola, Monilinia lax, Monilinia fructigena, Uncinulanecator, Gymnospor angium sabinae, Hemileia vastatrix, Phakopsora pachyrhizi, Phakopsora meibomiae, Uromyces appendiculatus, Albugo candida, Bremia lactucae, Peronospora pisi), Brassicae, Pseudoperonospora humuli, Pseudoperonos pora cubensis, Pythium ultimumultimum; leaf spot, Cladiosporium cucumerinum, Cochliobolus sativus, Cochliobolus miyabeanus, Colletotrichum lindemuthanium, Cycloconium oleaginum, Diaporthe citri, Elsinoe fawcettii, Gloeosporium laeticolor, Glomerella cingulata, Septoria apii, Septoria lycopercisi, Fusarium oxysporum, Rhizoctonia solan, Aspergillus flavus, Fusarium culmorum), Botrytis cinerea, Sclerotiniasclerotiorum, Fusariu m culmorum, Phytophthora cactorum, Pythium ultimum, Rhizoctonia solani, Rhizopus oryzae, Sclerotium rolfsii, Septoria nodorum, Botrytis cinerea, Xanthomonas oryzae, Pseudo monas lachrymans, Erwinia amylovora, Venturia inaequalis, Tilletia caries, Ustilago nuda), Ustilagoavenae, Pellicularia sasakii, Pyricularia oryzae, Le ptosphaeria nodorum, Pseudocercosporrelaherpotrichoides), Pyrenophora teres, Pyrenophora gram inea, etc. In some embodiments, ascarosides and one or more fungicides can be used to control Phoma leaf spot, Phoma stem canker, powdery mildew, yellow rust, brown rust, brown spot, Septoria leaf spot, and glume spot on cereals (including barley, rye, wheat, oats, etc.).

[0298] Specific diseases include, but are not limited to, anthracnose (Colletotrichum spp. / Microdochium panattonianum in lettuce, affects a variety of crops), botrytis rot (e.g., gray mold / Botrytis cinerea, affects a variety of crops), downy mildew (affects a variety of crops), white blister / rust (Albugo candida, typically in Brassica), Fusarium wilt and rot (Fusarium species, including F. solani and F. oxysporum), powdery mildew (affects a variety of crops), rust (several species, e.g., Puccinia sorghi in sweet corn; Puccinia verrucosa in beans, Puccinia oleracea in onions), allii, which affects a variety of crops and includes, for example, Asian soybean rust), Rhizoctonia rot (Rhizoctonia solani, commonly known as lettuce bottom rot / Brassica blackleg, affects a variety of crops), Sclerotinia rot (Sclerotinia solani and S. minor, which affect most vegetable crops), Sclerotinia rot (S. uniformis and S. cepivorum, which affect a variety of crops), Target spot (Alternaria solani, which affects tomatoes); Damping-off (Pythium, Rhizoctonia, Phytophthora, Fusarium, or Aphanomyces, which affect a variety of crops), Cavity spot (Pythium sulphate, which affects carrots) Clubroot (Brassica oleracea, usually in Brassica); Tuber diseases (affecting potatoes and sweet potatoes); Pythium species (affecting many vegetable crops); Carrot leaf blight (Alternaria carrot dauci); black root rot (different species on different crops, affecting multiple crops), and red root complex (affecting beans); Aphanomyces euteiches pv. Phaseoli (affecting beans); pea neck rot (affecting peas); Didymella bryoniae (affecting cucurbits); Alternaria leaf spot (Alternaria cucumerina and A. alternata (Cucurbitaceae)); blackleg (Microsphaerella punctata, affecting brassicas); ring spot (Mycosphaerella brassicicola, affecting brassicas); late blight (Septoria apiicola, affecting celery); Cercospora leaf spot (Cercosporium exigua, affecting sugar beets); leaf blight (Septoria oleracea, affecting sugar beets); petroelini, which affects parsley); Septoria leaf spot (Septoria lettuce, which affects lettuce); leaf blight (Sedum stolonifer, which affects onions); and leaf blight (Alternaria carotovora, which affects carrots).

[0299] In certain embodiments, plant diseases that can be treated or reduced or prevented by the compositions and / or methods described herein include, but are not limited to, plant diseases caused by fungi, viruses or viroids, protozoa, bacteria, and the like, for example, Asian soybean rust (ASR), gray mold, leaf spot, gray spot, early blight, damping-off complex, brown spot, black mole, root rot, belly rot, sheath blight, powdery mildew, anthracnose leaf spot, downy mildew, pythium wilt, late blight, Fusarium head blight (FHB), sudden death syndrome (SDS), Fusarium wilt, corn stalk rot, brown rust, black rust, yellow rust, wheat rust, rust, apple scab, verticillium wilt, fire blight, and brown rot.

[0300] Example

[0301] Example 1 : The composition containing ascaroside was applied at 25 mg / acre alone or with conventional fungicides. The combination was applied to winter wheat crops inoculated with Fusarium head blight. Applying ascarosides in combination with fungicides can provide additional protection against Fusarium head blight.

[0302] Example 2 : Compositions containing ascarosides were administered at 250 mg / ac alone or in combination with certain conventional fungicides (chlorothalonil and APROACH Combinations of picoxystrobin and cyproconazole) were applied to soybean crops. It was found that the application of ascarosides alone provided only low to moderate protection of 20% to 40% against Asian soybean rust. The combination of ascarosides with conventional fungicides can provide additional protection against Asian soybean rust compared to the application of the fungicides alone, while also increasing yield.

[0303] Example 3 : Will contain commercial ascaroside preparations A composition of wheat plants grown under greenhouse and / or growth chamber conditions and a triazole fungicide (tebuconazole) was applied by foliar spray to wheat plants. The composition was applied at a rate equivalent to the labeled dosage rate of tebuconazole and 25 mg / ac ascarosides. Three control groups were treated with: 1) a blank control composition containing no fungicide or ascarosides, 2) a composition containing tebuconazole alone (at the labeled dosage rate), or 3) a composition containing ascarosides alone (at 25 mg / ac equivalent). Forty-eight hours after treatment, the plants were inoculated with the fungal pathogen Helicoverpa spp. A few days after inoculation, all plants were scored for disease symptoms. Figure 2 As shown, the combination treatment was more effective in reducing disease systemically than ascarosides alone or tebuconazole alone.

[0304] Example 4 : Will contain commercial ascaroside preparations and PROSAROTM (a commercial fungicide containing a mixture of two triazole fungicides, tebuconazole and prothioconazole) was applied by foliar spray to wheat plants grown in random plots under field conditions. The application rate of the composition was equivalent to PROSARO TM and 25 mg / ac ascarosides at the labeled dosage rate. Three control groups were treated with: 1) a blank control composition containing no fungicide or ascarosides, 2) a control composition containing only PROSARO TM 3) a composition containing only ascarosides (at the indicated dosage rate). Figure 3 As shown, the combination treatment was more effective in reducing Fusarium head blight (FHB) incidence than either product alone.

[0305] Example 5 : Will contain commercial ascaroside preparations A composition of prothioconazole and chloranil was applied by foliar spray to wheat plants grown in random plots under field conditions. The composition was applied at a rate equivalent to the labeled dosage rate of prothioconazole and 25 mg / ac ascarosides. Three control groups were treated with: 1) a blank control composition containing no fungicide or ascarosides, 2) a composition containing prothioconazole alone (at the labeled dosage rate), or 3) a composition containing ascarosides alone (at 25 mg / ac equivalent). Figure 4 As shown, the combination treatment was more effective in reducing the severity of Septoria leaf spot symptoms than either product alone.

[0306] Example 6 : Will contain commercial ascaroside preparations and a mixture of propiconazole and the Class 7 fungicide fluopicolide by foliar spraying to wheat plants grown in random small plots under field conditions. The application rate of the composition was equivalent to the labeled dosage rate of propiconazole and fluopicolide and 25 mg / ac ascarosides. Three control groups were treated with the following substances: 1) a blank control composition without fungicides or ascarosides, 2) a composition containing only propiconazole and fluopicolide (at the labeled dosage rate), or 3) a composition containing only ascarosides (at 25 mg / ac equivalent). As Figure 5 As shown, the combination treatment was more effective than either product alone in reducing the severity of Fusarium head blight symptoms and was higher in yield than the individual treatments.

[0307] Example 7 : Will contain commercial ascaroside preparations A composition of prothioconazole and prothioconazole was applied by foliar spray to wheat plants grown in random plots under field conditions. The composition was applied at the labeled dosage rate of prothioconazole and 25 mg / ac ascarosides. Three control groups were treated with: 1) a blank control composition without fungicide or ascarosides, 2) a composition containing prothioconazole alone (at the labeled dosage rate), or 3) a composition containing ascarosides alone (at 25 mg / ac equivalent). Figure 6 As shown, the combination treatment was more effective in reducing the severity of Fusarium head blight symptoms than either product alone.

[0308] Example 8 : In two regions of Brazil prone to Asian soybean rust (ASR) infection, a composition containing ascaroside (ascr#18) was applied to soybean crops grown under field conditions by foliar spray at a rate of 250 mg / ac. The ascaroside composition can be used alone or in combination with certain conventional fungicides (chlorothalonil and APROACH Ascaroside alone was found to provide moderate (e.g., 20% to 40%) protection against Asian soybean rust relative to untreated controls. Fig. 9 Combinations of ascarosides with conventional fungicides may provide additional protection against Asian soybean rust compared to either application of the fungicide alone or application of ascarosides alone ( Fig. 9 and 10 Combinations of ascarosides with conventional fungicides can increase yield relative to conventional fungicide treatment alone ( Figure 7 and 8 ).

[0309] Example 9 : Will contain commercial ascaroside preparations A composition containing a commercial fungicide and a blend of the strobilurin fungicides picoxystrobin and thiophanate-methyl was applied by foliar spray to soybean plants grown under field conditions. The composition was applied at a rate equivalent to the labeled dosage rate of the commercial fungicide and 205 mg / ac ascarosides. Three control groups were treated with: 1) a blank control composition containing no fungicide or ascarosides, 2) a composition containing only the commercial fungicide (at the labeled dosage rate), and 3) a composition containing only ascarosides (at the equivalent of 205 mg / ac). Fig.11 As shown, the combination treatment was more effective in reducing disease symptoms than either ascaroside alone or the commercial fungicide alone.

[0310] Example 10 : Will contain ascaroside preparations A composition comprising a blend of a commercial formulation of the strobilurin fungicide azoxystrobin and a commercial formulation of the strobilurin fungicide azoxystrobin was applied by foliar spray to soybean plants grown under field conditions and inoculated with Asian soybean rust. The composition was applied at a rate equivalent to the labeled dosage rate of the commercial fungicide and 50 mg / ac ascarosides. Four control groups were treated with: 1) no fungicide or ascarosides; 2) azoxystrobin fungicide alone (at the labeled rate); and 3) an ascarosides composition alone (at 50 mg / ac equivalent); and 4) Trivapro alone (a best-in-class commercial fungicide containing a 3-way blend of propiconazole, azoxystrobin and benzophenone). Fig.12 and 13 As shown, the ascaroside combination treatment was more effective in reducing disease symptoms and increasing yield than either ascaroside alone or the commercial fungicide alone, and outperformed the best-in-class 3-way blend.

[0311] Embodiment 11 : Will contain ascaroside preparations A composition of a blend of a commercial formulation of the strobilurin fungicide azoxystrobin was applied by foliar spray to wheat plants grown in a growth chamber and inoculated with Helicoverpa spp., the fungal pathogen that causes spot disease. The blend containing the commercial azoxystrobin composition was diluted to provide an application rate equivalent to 1 / 20 of the standard labeled application rate, and the ascaroside composition was applied at a concentration equivalent to 25 mg of ascaroside per acre. Shows excellent disease control effect ( Fig.14 , right column). Three control groups were included for comparison: 1) no fungicide or ascaroside treatment (blank control), 2) treatment with only azoxystrobin fungicide at 1 / 20 of the labeled dosage rate (azoxystrobin), and 3) treatment with only the ascaroside composition at 25 mg / ac equivalent. These data ( Fig.14 ) demonstrated synergy between an ascaroside combination and the strobilurin azoxystrobin and demonstrated that incorporation of the ascaroside in this blend enabled a reduction in the amount of fungicide. Notably, the blend showed the highest level of pathogen inhibition, indicating that resistance is unlikely to develop.

[0312] Example 12 : Will contain ascaroside preparations A composition of a blend of a commercial formulation of the SDHI fungicide, fluopyram, was applied by foliar spray to wheat plants grown in a growth chamber and inoculated with Helicoverpa spp., the fungal pathogen that causes spot disease. The blend containing the commercial fluopyram composition was diluted to provide an application rate equivalent to 1 / 20 of the standard labeled application rate, and the ascaroside composition was applied at a concentration equivalent to 25 mg of ascaroside per acre. Shows excellent disease control effect ( Fig.15Three control groups were included for comparison: 1) no fungicide or ascaroside treatment (blank control), 2) treatment with only SDHI fungicide (fluopyrab) at 1 / 20 of the labeled dosage rate, and 3) treatment with only 25 mg / ac equivalent of the ascaroside composition. These data demonstrate synergy between the ascaroside combination and SDHI fluopyrab, and confirm that inclusion of ascaroside in this blend can reduce the amount of fungicide. Notably, the blend showed the highest level of pathogen inhibition, indicating that resistance is unlikely to develop.

[0313] Example 13 :Research Stability of combinations with various other commercial fungicide products. Two sets of samples were generated to replicate tank mixes (e.g. and commercial products), diluting the sample into water at the indicated dosage rate and preparing a blend, wherein The concentrate was added directly to the formulated commercial product. Samples were stored at room temperature and 40°C (for accelerated aging) and monitored regularly using HPLC / MS quantification. The 6-month results are summarized below. The data unexpectedly showed that The combinations with commercial fungicides were stable (e.g., in terms of ascaroside content) in both the concentrate formulation and tank-mix concentrations, with a shelf life of at least 6 months or at least 12 months, despite the extremely low levels of ascaroside present in each formulation. This finding was particularly unexpected because, in general, formulating mixtures of chemical and biological components can be quite challenging due to the incompatibility of these components with each other.

[0314] Table 1: Stability of ascaroside-containing combination formulations over a 6-month period

[0315]

[0316] Table 2: Stability of ascaroside-containing combination formulations over 12 months

[0317]

[0318] Embodiment 14 : Field trials were conducted to evaluate the efficacy of ascaroside seed treatments alone and in combination with a multi-component commercial fungicide for the control of wheat bacterial leaf streak. (Apply at 2.5 ppm alone or at the labeled rate with Apron Maxx TM (Metalaxyl-M, Fludioxonil) combination) was used to treat wheat seeds. Seeds treated with blank control and seeds treated with Apron Maxx only were TMThe treated seeds were planted in the field as a control. The incidence of bacterial leaf streak in the treatment groups was scored 2 months after planting and the results were plotted on Fig.16 In. Fig.16 As shown, use and Apron Maxx TM Fields planted with seeds treated with the combination had the lowest incidence of bacterial leaf streak, indicating additive and / or synergistic activity exceeding that of either product alone in controlling this pathogen of wheat.

[0319] Embodiment 15 : Field trials were conducted to evaluate the efficacy of seed treatments with ascaroside alone and in combination with a multi-component commercial fungicide to extend the photosynthetic period of corn. (Apply at 5 ppm alone or at the labeled dose rate with Apron Maxx TM (Metalaxyl-M, Fludioxonil) combination) was used to treat corn seeds. Seeds treated with blank control and seeds treated with Apron Maxx only were TM The field planted with treated seeds served as a control. The stay-green effect (grade 1-9) was measured 156 days after planting. Fig.17 As shown. Fig.17 As shown, and Apron Maxx TM The combination of showed the highest stay-green effect score, indicating additive and / or synergistic activity exceeding that of either product alone.

[0320] Example 16 : Field trials were conducted to evaluate the efficacy of seed treatments with ascaroside alone and in combination with a multi-component commercial fungicide to increase germination and emergence of soybean seeds. (Apply at 5 ppm alone or at the labeled dose rate with Apron Maxx TM (Metalaxyl-M, Fludioxonil) combination) was used to treat soybean seeds. Seeds treated with blank control and seeds treated with Apron Maxx only were TM The plots planted with treated seeds served as controls. The stand counts for each plot were measured at 50% germination and then extrapolated to the number of seedlings per acre. The results are plotted on Fig.18 In. Fig.18 As shown, and Apron Maxx TM The combination of showed the highest erection counts, indicating additive and / or synergistic activity exceeding that of either product alone.

[0321] It is expected that the compounds, compositions and methods of the present application cover changes and adjustments developed using the information of the embodiments described in this disclosure. The methods and processes described in this specification may be adjusted or modified by a person of ordinary skill in the relevant art. It should be understood that the use of titles in this disclosure is for the convenience of the reader.

[0322] The existence and / or placement of titles are not intended to limit the scope of the subject matter described herein. Unless otherwise indicated, the embodiments located in a certain section of the application can be applied to other embodiments individually or in combination throughout the application. Throughout the specification, when a composition, compound or product is described as having, including or comprising a specific component, or when a process and method are described as having, including or comprising a specific step, it is also contemplated that there are articles, devices and systems of the present application that are basically composed of or composed of the components, and there are processes and methods according to the present application that are basically composed of or composed of the processing steps. It should be understood that as long as the method is still feasible, the order of the steps or the order in which certain actions are performed is not important. In addition, two or more steps or actions can be performed simultaneously.

[0323] All publications and patent applications mentioned in the specification are indicative of the level of those skilled in the art to which the invention pertains. All publications and patent applications are incorporated herein by reference to the same extent as if each individual publication or patent application was specifically and individually indicated to be incorporated by reference. Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, it will be apparent that certain changes and modifications may be made within the scope of the appended claims.

Claims

1. A method of enhancing the activity of a fungicide comprising co-applying the fungicide and one or more ascarosides to a plant, plant part, or the soil surrounding the plant or plant part.

2. The method of claim 1, wherein the fungicide is a biofungicide.

3. The method of claim 1, wherein the fungicide is a chemical fungicide selected from the group consisting of azoles, strobilurins, carboxamides, nitrogen-containing heterocyclic compounds, carbamates and dithiocarbamates, guanidines, antibiotics, organometallic compounds, sulfur-containing heterocyclic compounds, organophosphorus compounds, organochlorine compounds, nitrophenyl derivatives, inorganic active compounds, and combinations thereof.

4. A method of enhancing the activity of a fungicide comprising co-applying the fungicide and one or more ascarosides to a plant, a plant part, or the soil surrounding the plant or plant part, a. wherein the fungicide comprises a triazole fungicide; b. Wherein the fungicide comprises Q o I. Fungicide; or c. wherein the fungicide comprises a SDHI fungicide.

5. The method of claim 4, wherein the triazole fungicide is prothioconazole or tebuconazole.

6. The method of claim 4, wherein said Q o I fungicide is a strobilurin selected from the group consisting of azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, enoxastrobin, diastereamine, fluoxastrobin, fenoxystrobin, tosoxastrobin, pyraclostrobin, pyraclostrobin, diastereamine, tosoxastrobin, pyraclostrobin, pyraclostrobin, kresoxim-methyl, fenamidone or famoxadone.

7. The method of claim 4, wherein the SDHI fungicide is a benzamide fungicide that inhibits succinate dehydrogenase (SDH) complex II, wherein the benzamide fungicide is selected from the group consisting of fluadoxam, flurenoxadiazam, flutolanil, ortho-amide, bacitracin, fluopyram, benzohydroxamic acid, flutolanil, fluopyram, flutolanil, thiocyanate, trchlamide, cyanamide and zoxamide.

8. The method of claim 4, wherein the SDHI fungicide is a formamide fungicide that inhibits succinate dehydrogenase (SDH) complex II, and wherein the formamide fungicide is selected from the group consisting of: Oxathiin fungicides; Furanamide fungicides; Pyrazinecarboxamide fungicides; Pyrazole carboxamide fungicides; and Pyridinecarboxamide fungicide.

9. The method of claim 8, wherein the formamide fungicide is selected from the group consisting of carboxin, oxycarboxin, furamide, dimethylfuran, furazolidone, bixafen, benzovinflumazole, bixafen, flufenoxamide, fluinoxazolidone, fluopyram, furazolidone, indopyram, isoproflupyram, pyraclostrobin, fluopyram, penthiopyrad, fluopyram, pyridoxamid, pyridoxamid, fluopyram, oxathiapiprolin, pyridoxamid, fluopyram, oxathiapiprolin, pyridoxamid, fluopyram, oxathiapiprolin, thiafuram, boscalid and triflupyramide.

10. The method of claim 4, wherein the SDHI fungicide comprises a thiopheneamide fungicide, and wherein the thiopheneamide fungicide is isoflurane.

11. The method of any one of claims 1 to 10, which provides increased total yield of the plant, wherein the increased total yield of the plant is greater than the yield of a plant treated with the fungicide alone plus the yield of a plant treated with the one or more ascarosides alone.

12. The method of any one of claims 1 to 11, which provides enhanced disease protection, wherein the enhanced disease protection is greater than the disease protection provided by treatment with the fungicide alone plus the disease protection provided by treatment with the one or more ascarosides alone.

13. The method of any one of claims 1 to 12, wherein the co-administration comprises administering the fungicide and the one or more ascarosides in separate formulations.

14. The method of any one of claims 1 to 12, wherein the co-application comprises applying the fungicide and the one or more ascarosides in a single formulation.

15. The method of any one of claims 1 to 14, wherein the one or more ascarosides have structure (I) in: Z is an optionally substituted C 2-40 an aliphatic group, and R a and R b Each of the following is independently -H, or an optionally substituted moiety selected from the group consisting of: C 1-20 Aliphatic group, C 1-20 Acyl, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus-linked functional group, sulfur-linked functional group, silicon-linked functional group, C 2-20 Carbonate (e.g., part -C(O)OR c ), C 2-20 Carbamate (e.g., part -C(O)N(R c )2) C 2-20 Thioesters (e.g., moieties -C(S)R c ), C 2-20 Thiocarbonates (e.g., moieties -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., part-C(S)SR c ), C 1-20 Thiocarbamates (e.g., moieties -C(S)N(R c ) 2), a sugar moiety, a peptide, a polymer chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, wherein R c is independently selected at each occurrence from -H, optionally substituted C 1-12 aliphatic, optionally substituted C 1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, and wherein R a and R b Can be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

16. The method of claim 15, wherein Z is selected from the group consisting of: i.–CH(CH3)–R 1 , where R 1 is an optionally substituted C 1-40 aliphatic groups; ii.–CH(CH3)–(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; iii.–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; iv.–CH(CH3)–(CH2) n –CH(OH)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; v.–CH(CH3)–(CH2) n –C(O)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; vi.–(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; vii.–(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; viii.–(CH2) n –CH(OH)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; and ix.–(CH2) n –C(O)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety. x.–CH(CH3)–(CH2) n –CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xi.–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xii.–CH(CH3)–(CH2) n –CH(OH)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xiii.–CH(CH3)–(CH2) n –C(O)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xiv.–(CH2) n –CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xv.–(CH2) n –CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xvi.–(CH2) n –CH(OH)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; and xvii.–(CH2) n –C(O)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

17. The method of any one of claims 1 to 16, wherein the one or more ascarosides comprises ascr#18.

18. A composition comprising one or more ascarosides and one or more fungicides.

19. The composition of claim 18, wherein the one or more fungicides comprise a biofungicide.

20. The composition of claim 18, wherein the one or more fungicides comprise a chemical fungicide selected from the group consisting of azoles, strobilurins, carboxamides, nitrogen-containing heterocyclic compounds, carbamates and dithiocarbamates, guanidines, antibiotics, organometallic compounds, sulfur-containing heterocyclic compounds, organophosphorus compounds, organochlorine compounds, nitrophenyl derivatives, inorganic active compounds, and combinations thereof.

21. A composition comprising one or more ascarosides and one or more fungicides, a. wherein the one or more fungicides include a triazole fungicide; b. wherein the one or more fungicides include Q o I. Fungicide; or c. wherein the one or more fungicides include a SDHI fungicide.

22. The composition of claim 21, wherein the triazole fungicide is prothioconazole or tebuconazole.

23. The composition of claim 21, wherein Q o I fungicide is a strobilurin selected from the group consisting of azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, enoxastrobin, diastereamine, fluoxastrobin, fenoxystrobin, tosoxastrobin, pyraclostrobin, pyraclostrobin, kresoxim-methyl, fenamidone and famoxadone.

24. The composition of claim 21, wherein the SDHI fungicide is a benzamide fungicide that inhibits succinate dehydrogenase (SDH) complex II, wherein the benzamide fungicide is selected from the group consisting of flucarbamide, flurenoxadiazam, flutolanil, ortho-amide, flutolanil, fluopyram, benzohydroxamic acid, flutolanil, fluopyram, flutolanil, thiocyanate, trchlamide, cyanamide, and zoxamide.

25. The composition of claim 21, wherein the SDHI fungicide is a formamide fungicide that inhibits succinate dehydrogenase (SDH) complex II, and wherein the formamide fungicide is selected from the group consisting of: Oxathiin fungicides; Furanamide fungicides; Pyrazinecarboxamide fungicides; Pyrazole carboxamide fungicides; and Pyridinecarboxamide fungicide.

26. The composition of claim 25, wherein the formamide fungicide is selected from the group consisting of carboxin, oxycarboxin, furamide, dimethylfuran, furazolidone, bixafen, benzovinflumazole, bixafen, flufenoxamide, fluinoxazolidone, flutolanil, fluopyram, furazolidone, indopyram, isoproflupyram, pyraclostrobin, fluopyram, penthiopyrad, fluopyram, pyridoxadone, flutolanil, pyridoxadone, flutolanil, thiamethoxam, boscalid and triflupyramide.

27. The composition of claim 21, wherein the SDHI fungicide comprises a thiopheneamide fungicide, and wherein the thiopheneamide fungicide is isoflavone.

28. The composition of any one of claims 18 to 27, wherein the at least one ascaroside and the fungicide are present in effective amounts, and wherein the effective amounts provide synergistic activity in controlling fungal diseases.

29. The composition of any one of claims 18 to 28, wherein the one or more ascarosides have structure (I) in: Z is an optionally substituted C 3-40 an aliphatic group, and R a and R b Each of the following is independently -H, or an optionally substituted moiety selected from the group consisting of: C 1-20 Aliphatic group, C 1-20 Acyl, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus-linked functional group, sulfur-linked functional group, silicon-linked functional group, C 2-20 Carbonate (e.g. part -C(O)OR c ), C 2-20 Carbamate (e.g., part -C(O)N(R c )2) C 2-20 Thioesters (e.g., moieties -C(S)R c ), C 2-20 Thiocarbonates (e.g., moieties -C(S)OR c ), C 2-20 Dithiocarbonates (e.g., part-C(S)SR c ), C 1-20 Thiocarbamates (e.g., moieties -C(S)N(R c ) 2), a sugar moiety, a peptide, a polymer chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, wherein R c is independently selected at each occurrence from -H, optionally substituted C 1-12 aliphatic, optionally substituted C 1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, and wherein R a and R b Can be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

30. The composition of claim 29, wherein Z is selected from the group consisting of: i.–CH(CH3)–R 1 , where R 1 is an optionally substituted C 1-40 aliphatic groups; ii.–CH(CH3)–(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; iii.–CH(CH3)–(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; iv.–CH(CH3)–(CH2) n –CH(OH)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; v.–CH(CH3)–(CH2) n –C(O)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; vi.–(CH2) n –CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; vii.–(CH2) n –CH=CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; viii.–(CH2) n –CH(OH)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; ix.–(CH2) n –C(O)–CH-CO2R 2 , wherein n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety. x.–CH(CH3)–(CH2) n –CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xi.–CH(CH3)–(CH2) n –CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xii.–CH(CH3)–(CH2) n –CH(OH)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xiii.–CH(CH3)–(CH2) n –C(O)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xiv.–(CH2) n –CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xv.–(CH2) n –CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; xvi.–(CH2) n –CH(OH)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; and xvii.–(CH2) n –C(O)–CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 An aliphatic group, an optionally substituted C 1-20 a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

31. The composition of any one of claims 18 to 30, wherein the one or more ascarosides comprises ascr#18.

32. A composition as claimed in any one of claims 18 to 31 in solid form.

33. The composition of claim 33, wherein the solid form comprises a powder or granules.

34. A composition as claimed in any one of claims 18 to 31 in liquid form.

35. The composition of claim 34, wherein the liquid form is a sprayable formulation.

36. A composition as claimed in claim 35 or claim 36, wherein the composition has a shelf life of greater than 6 months.

37. The composition of any one of claims 18 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, ultraviolet radiation absorbers, weathering stabilizers, plasticizers, release agents, fragrances, thermal insulation additives (e.g., silica), cross-linking agents, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, extenders / stickers, tackifiers, plant penetrants, safeners, spreaders, and wetting agents.

38. The composition of any one of claims 18 to 37, wherein the fungicide and the ascaroside are present in a weight ratio of greater than 1000: 1 fungicide:ascaroside.

39. The composition of any one of claims 18 to 38 which is labeled for application to a crop at a rate less than the labeled dosage rate of the fungicide alone.

40. The composition of any one of claims 18 to 39 indicated for application to crops at a rate to deliver less than 4 ounces of said fungicide per acre.

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