Combinations of ascarosides

Abstract

This application relates to combinations of one or more ascalosides and one or more additional active agents (e.g., fungicides). Various combinations can provide enhanced crop protection, and certain combinations exhibit surprising synergistic effects. Surprisingly, the various combinations can be co-formulated to provide storage-stable compositions. The present disclosure provides compositions and methods that include applying one or more ascalosides in combination with one or more additional active agents to plants.

Description

Technical Field

[0001] Cross - Reference to Related Applications This application claims priority to U.S. Provisional Patent Application No. 63 / 344,937, entitled "Ascaroside Combinations", filed on May 23, 2022; U.S. Provisional Patent Application No. 63 / 421,340, entitled "Ascarosides and Fungicidal Combinations and Methods for Use", filed on November 1, 2022; U.S. Provisional Patent Application 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 No. 63 / 486,018, entitled "Ascarosides and SDHI Fungicidal Combinations and Methods of Use", filed on February 20, 2023, all of which are hereby incorporated by reference in their entirety.

[0002] This application generally relates to pesticidal compounds, compositions, and methods of treating plants to promote resistance to pathogens.

Background Art

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

[0004] When applied to plants, ascaloside treatment has been shown to be effective in increasing plant resistance to specific pathogens and / or inducing and priming the plant's defense response (which can inhibit pathogen growth and / or parasitism). Ascalosides can prevent pathogen proliferation and / or protect crops from the harmful effects caused by various pathogens by activating and / or priming the plant's innate defenses.

[0005] Pesticide treatment generally involves applying two or more active agents to the plant and the surrounding soil to effectively protect the plant from various pathogens. It would be useful to provide additional combinations, compositions, and methods capable of providing plant protection.

Summary of the Invention

[0006] The present disclosure provides compositions and methods comprising applying one or more ascalosides in combination with one or more additional active agents to a plant. In some embodiments, co - applying one or more ascalosides with one or more additional active agents can provide a synergistic effect on plant protection and / or yield. In some embodiments, co - applying one or more ascalosides with one or more additional active agents can include applying the components within a single formulation (e.g., a liquid formulation). In some embodiments described herein, such a formulation can be advantageously stable over a long period. This stability is surprising, as formulations containing two or more active agents are often plagued by instability (e.g., manifested as separation, sedimentation, a decrease in the content of the active agent relative to the starting content, etc.).

[0007] The present disclosure includes, but is not limited to, the following embodiments.

[0008] Embodiment 1: A method of enhancing the activity of a fungicide, the method comprising co - administering the fungicide and one or more ascalosides to a plant, a plant part, or the soil surrounding the plant or the plant part.

[0009] Embodiment 2: The method according to Embodiment 1, wherein the fungicide is a biological fungicide.

[0010] Embodiment 3: The method according to Embodiment 1, wherein the fungicide is a chemical fungicide.

[0011] Embodiment 4: The method according to claim 3, wherein the chemical fungicide is selected from the group consisting of azoles, strobilurins, carboxamides, nitrogenous 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.

[0012] Embodiment 5: A method for enhancing the activity of a fungicide, comprising co-administering the fungicide and one or more ascaryosides to a plant, a plant part, or soil surrounding the plant or the plant part, wherein the fungicide comprises a triazole fungicide.

[0013] Embodiment 6: The method according to Embodiment 5, wherein the triazole fungicide is prothioconazole or tebuconazole.

[0014] Embodiment 7: A method for enhancing the activity of a fungicide, comprising co-administering the fungicide and one or more ascaryosides to a plant, a plant part, or soil surrounding the plant or the plant part, wherein the fungicide comprises a Q o I fungicide.

[0015] Embodiment 8: The Q o I fungicide is strobilurin, according to the method of embodiment 7.

[0016] Embodiment 9: The method according to claim 8, wherein the strobilurin is selected from the group consisting of azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, fenamidone, dimoxystrobin, fluoxastrobin, metominostrobin, mandestrobin, pyra-metostrobin, pyrazooxystrobin, kresoxim-methyl, fenamidone, or famoxadone.

[0017] Embodiment 10: The method according to Embodiment 9, wherein the strobilurin is azoxystrobin, picoxystrobin, or trifloxystrobin.

[0018] Embodiment 11: The method according to Embodiment 9, wherein the strobilurin is azoxystrobin.

[0019] Embodiment 12: The Q o The method according to Embodiment 7, wherein the QI fungicide is fenamidone or famoxadone.

[0020] Embodiment 13: A method for enhancing the activity of a fungicide, comprising co-administering the fungicide and one or more ascarosides to a plant, a plant part, or soil surrounding the plant or plant part, wherein the fungicide comprises an SDHI fungicide.

[0021] Embodiment 14: The method according to Embodiment 13, wherein the SDHI fungicide comprises a benzamide fungicide that inhibits succinate dehydrogenase (SDH) complex II.

[0022] Embodiment 15: The method according to Embodiment 14, wherein the benzamide fungicide is benodanil, flurenoxadiazam, flutolanil, mebenil, mepronil, fluopyram, benzohydroxamic acid, flumetover, flupicolide, flupimomoide, thioxymide, trchlamide, zarilamide, or zoxamide.

[0023] Embodiment 16: The method according to Embodiment 13, wherein the SDHI fungicide comprises a carboxamide fungicide that inhibits succinate dehydrogenase (SDH) complex II.

[0024] Embodiment 17: The method according to Embodiment 16, wherein the carboxamide fungicide is an oxathiine fungicide.

[0025] Embodiment 18: The method according to Embodiment 17, wherein the oxathiine fungicide is carboxin or oxycarboxin.

[0026] Embodiment 19: The method according to Embodiment 16, wherein the carboxamide fungicide is a furancarboxamide fungicide.

[0027] Embodiment 20: The method according to Embodiment 19, wherein the furancarboxamide fungicide is fenfuram, flutolanil, or metalaxyl-M.

[0028] Embodiment 21: The method according to Embodiment 16, wherein the carboxamide fungicide is a pyrazinecarboxamide fungicide.

[0029] Embodiment 22: The method according to Embodiment 21, wherein the pyrazinecarboxamide fungicide is pyraclostrobin.

[0030] Embodiment 23: The method according to Embodiment 16, wherein the carboxamide fungicide is a pyrazolecarboxamide fungicide.

[0031] Embodiment 24: The method according to Embodiment 23, wherein the pyrazolecarboxamide fungicide is selected from the group consisting of benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, fluopyram, flutianil, isopyrazam, penflufen, penthiopyrad, picoxystrobin, pyrapropyzamide, sedaxane, ethaboxam, and difenoconazole.

[0032] Embodiment 25: The method according to embodiment 16, wherein the carboxamide fungicide is a pyridinecarboxamide fungicide.

[0033] Embodiment 26: The method according to embodiment 25, wherein the pyridinecarboxamide fungicide is boscalid or cyclobutrifluram.

[0034] Embodiment 27: The method according to embodiment 13, wherein the SDHI fungicide comprises a thiopheneamide fungicide.

[0035] Embodiment 28: The method according to embodiment 27, wherein the thiopheneamide fungicide is isofetamid.

[0036] Embodiment 29: The method according to any one of embodiments 1 to 28, which provides an increase in the overall yield of the plant.

[0037] Embodiment 30: The method according to embodiment 29, wherein the increased total yield of the plant is greater than the yield of the plant treated with the fungicide alone + the yield of the plant treated with the one or more ascalosides alone.

[0038] Embodiment 31: The method according to any one of embodiments 1 to 30, which provides an increase in disease protection.

[0039] Embodiment 32: The method according to embodiment 31, wherein the increase in disease protection is greater than the disease protection provided by treatment with the fungicide alone + the disease protection provided by treatment with the one or more ascalosides alone.

[0040] Embodiment 33: The method according to any one of embodiments 1 to 32, wherein the co - administration comprises applying the fungicide and the one or more ascalosides in the form of separate formulations.

[0041] Embodiment 34: The method according to any one of embodiments 1 to 32, wherein the co - administration comprises applying the fungicide and the one or more ascalosides in the form of a single formulation.

[0042] Embodiment 35: The method according to embodiment 34, wherein the formulation is storage-stable for a period exceeding 6 months.

[0043] Embodiment 36: The one or more ascaryosides have structure (I) [Chemical formula] wherein Z is an optionally substituted C 2~40 aliphatic group, and each of R a and R b is independently -H, or a C 1~20 aliphatic, C 1~20 acyl, C 1~20 heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus-bonding functional group, sulfur-bonding functional group, silicon-bonding functional group, C 2~20 carbonate (e.g., moiety -C(O)OR c ), C 2~20 carbamate (e.g., moiety -C(O)N(R c ) 2 ), C 2~20 thioester (e.g., moiety -C(S)R c ), C 2~20 thiocarbonate (e.g., moiety -C(S)OR c ), C 2~20 dithiocarbonate (e.g., moiety -C(S)SR c ), C 1~20 thiocarbamate (e.g., moiety -C(S)N(R c ) 2 ), a sugar moiety, a peptide, a polymer chain, or a moiety selected from the group consisting of a bond to another ascaryoside molecule or a linkage via a carbon-containing linker moiety, and is an optionally substituted moiety, and R c is independently at each occurrence -H, an optionally substituted C 1~12 aliphatic, an optionally substituted C 1~12 heteroaliphatic, an optionally substituted aryl, an optionally substituted heteroaryl, a polymer chain, or a bond to another ascaryoside molecule or a linkage via a carbon-containing linker moiety, and R a and Rb The method according to any one of Embodiments 1 to 35, which may combine to form an optionally substituted ring containing one or more heteroatoms and optionally one or more unsaturated sites as desired.

[0044] Embodiment 37: Z is (i) -CH(CH 3 )-R 1 (R 1 is an optionally substituted C 1~40 aliphatic group), (ii) -CH(CH 3 )-(CH 2 ) n- CO 2 R 2 (n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), (iii) -CH(CH 3 )-(CH 2 ) n- CH=CH-CO 2 R 2 (n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), (iv) CH(CH 3 )-(CH 2 ) n- CH(OH)-CH-CO 2 R 2 (n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20A bond to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascarylose molecule, or a bond through a carbon-containing linker moiety; (v)-CH(CH 3 )-(CH 2 ) n -C(O)-CH-CO 2 R 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 group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage through a carbon-containing linking moiety to another ascarylose molecule), (vi)-(CH 2 ) n- CO 2 R 2 (n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond or a linkage through a carbon-containing linker moiety to another ascarylose molecule), (viii)-(CH 2 ) n- CH=CH-CO 2 R 2 (n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond or a linkage through a carbon-containing linker moiety to another ascarylose molecule), (viii)-(CH 2 ) n- CH(OH)-CH-CO 2 R 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 group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascaryoside molecule or a bond through a carbon-containing linker moiety), and (ix)-(CH 2 ) n- C(O)-CH-CO 2 R 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 group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascaryoside molecule or a bond through a carbon-containing linker moiety) selected from the group consisting of, the method according to embodiment 36.

[0045] Embodiment 38: Z is (x)-CH(CH 3 )-(CH 2 ) n -CON(R 3 ) 2 (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascaryoside molecule or a linkage through a carbon-containing linker moiety), (xi)-CH(CH 3 )-(CH 2 ) n- CH=CH-CON(R 3 ) 2 , (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C1~20 An aliphatic group, a C optionally substituted 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (xii)-CH(CH 3 )-(CH 2 ) n- CH(OH)-CH-CON(R 3 ) 2 , (wherein n is an integer from 1 to 40, and each R 3 is, independently, -H, a C optionally substituted 1~20 aliphatic group, a C optionally substituted 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (xiii)-CH(CH 3 )-(CH 2 ) n- C(O)-CH-CON(R 3 ) 2、 (wherein n is an integer from 1 to 40, and each R 3 is, independently, -H, a C optionally substituted 1~20 aliphatic group, a C optionally substituted 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (xiii)-(CH 2 ) n- CON(R 3 ) 2、 (wherein n is an integer from 1 to 40, and each R 3 is, independently, -H, a C optionally substituted 1~20 aliphatic group, a C optionally substituted 1~20a bond to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascarylose molecule or a bond via a carbon-containing linker moiety), (xiv)-(CH 2 ) n- CH=CH-CON(R 3 ) 2 (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (xv)-(CH 2 ) n- CH(OH)-CH-CON(R 3 ) 2 (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), and (xvi)-(CH 2 ) n- C(O)-CH-CON(R 3 ) 2 (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), a method according to embodiment 36, selected from the group consisting of

[0046] Embodiment 39: R a and R b is -H in each case, the method according to any one of Embodiments 36 to 38.

[0047] Embodiment 40: Z is -CH(CH 3 )-(CH 2 ) n- CO 2 R 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 group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide, the method according to any one of Embodiments 36 to 39.

[0048] Embodiment 41: The method according to any one of Embodiments 1 to 35, wherein the one or more ascalosides comprise ascr#18.

[0049] Embodiment 42: The method according to any one of Embodiments 1 to 41, wherein the plant or plant part is selected from plants or plant parts of crop plants (for example, corn, alfalfa, sunflower, Brassica, soybean, cotton, safflower, peanut, sorghum, wheat, millet, or tobacco).

[0050] Embodiment 43: The method according to any one of Embodiments 1 to 42, wherein the activity is against a plant disease (for example, Asian soybean rust (ASR), gray mold, leaf spot, Frogeye leaf spot, summer blight, damping-off complex, leaf rot, black scab, root rot, belly rot, southern blight, powdery mildew, anthracnose leaf spot, downy mildew, red rot, Late Blight, Fusarium head blight (FHB), sudden death syndrome (SDS), damping-off caused by Fusarium spp., corn stalk rot, brown rot, black rot, yellow rot, wheat rust, rust, apple scab, wilt, fire blight, and brown rot) caused by fungi, viruses or viroids, protozoa, bacteria, etc.

[0051] Embodiment 44: A composition comprising one or more ascalosides and one or more fungicides.

[0052] Embodiment 45: The composition according to Embodiment 44, wherein the one or more fungicides include biological fungicides.

[0053] Embodiment 46: The composition according to Embodiment 44, wherein the one or more fungicides include chemical fungicides.

[0054] Embodiment 47: The composition according to Embodiment 46, wherein the chemical fungicide is selected from the group consisting of azoles, strobilurins, carboxamides, nitrogenous 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.

[0055] Embodiment 48: A composition comprising one or more ascalosides and one or more fungicides including a triazole fungicide.

[0056] Embodiment 49: The composition according to Embodiment 48, wherein the triazole fungicide is prothioconazole or tebuconazole.

[0057] Embodiment 50: A composition comprising at least one ascaloside and one or more fungicides including at least one Q o I fungicide.

[0058] Embodiment 51: The composition according to Embodiment 50, wherein the Q o I fungicide includes strobilurin.

[0059] Embodiment 52: The composition according to Embodiment 51, wherein the strobilurin is selected from the group consisting of azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, fenamidstrobin, dimoxystrobin, fluoxastrobin, metominostrobin, mandestrobin, pyrametostrobin, pyrazooxystrobin, kresoxim-methyl, fenamidone, and famoxadone.

[0060] Embodiment 53: The composition according to Embodiment 52, wherein the strobilurin is azoxystrobin, picoxystrobin, or trifloxystrobin.

[0061] Embodiment 54: The composition according to Embodiment 52, wherein the strobilurin is azoxystrobin.

[0062] Embodiment 55: A composition comprising at least one ascarylose and one or more fungicides including an SDHI fungicide.

[0063] Embodiment 56: The composition according to Embodiment 55, wherein the SDHI fungicide comprises a benzamide fungicide that inhibits succinate dehydrogenase (SDH) complex II.

[0064] Embodiment 57: The composition according to Embodiment 56, wherein the benzamide fungicide is benodanil, flurenoxadiazam, flutolanil, mebenil, mepronil, fluopyram, benzohydroxamic acid, flumetover, flupicolide, flupimomoide, thioxamide, trchlamide, zarilamide, or zoxamide.

[0065] Embodiment 58: The composition according to Embodiment 55, wherein the SDHI fungicide comprises a carboxamide fungicide that inhibits succinate dehydrogenase (SDHI) complex II.

[0066] Embodiment 59: The composition according to Embodiment 58, wherein the carboxamide fungicide is an oxathiine fungicide.

[0067] Embodiment 60: The composition according to Embodiment 59, wherein the oxathiine fungicide is carboxin or oxycarboxin.

[0068] Embodiment 61: The composition according to Embodiment 58, wherein the carboxamide fungicide is a furancarboxamide fungicide.

[0069] Embodiment 62: The composition according to Embodiment 61, wherein the furancarboxamide fungicide is fenfuram, flutolanil, or metalaxyl-M.

[0070] Embodiment 63: The composition according to Embodiment 58, wherein the carboxamide fungicide is a pyrazinecarboxamide fungicide.

[0071] Embodiment 64: The composition according to Embodiment 63, wherein the pyrazinecarboxamide fungicide is pyraclostrobin.

[0072] Embodiment 65: The composition according to Embodiment 58, wherein the carboxamide fungicide is a pyrazolecarboxamide fungicide.

[0073] Embodiment 66: The composition according to Embodiment 65, wherein the pyrazolecarboxamide fungicide is selected from the group consisting of benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, fluopyram, flutianil, ipfencarbazone, isoflucypram, isopyrazam, penthiopyrad, pydiflumetofen, pyrapropyzamide, sedaxane, ethaboxam, and difenoconazole.

[0074] Embodiment 67: The composition according to Embodiment 58, wherein the carboxamide fungicide is a pyridinecarboxamide fungicide.

[0075] Embodiment 68: The composition according to any one of Embodiments 44 to 67, wherein the at least one ascaloside and the fungicide are present in an effective amount, and the effective amount provides a synergistic activity in the control of fungal diseases.

[0076] Embodiment 69: The one or more ascalosides have structure (I), wherein Z

Chemical formula

[0077] Embodiment 70: Z is (i) -CH(CH 3 )-R 1 (wherein R 1 is an optionally substituted C 1~40 aliphatic group, (ii) -CH(CH 3 )-(CH 2 ) n -CO 2 R 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 group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (iii) -CH(CH 3 )-(CH 2 ) n- CH=CH-CO 2 R 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 group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (iv) -CH(CH 3 )-(CH 2 ) n- CH(OH)-CH-CO2 R 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 group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (v)-CH(CH 3 )-(CH 2 ) n- C(O)-CH-CO 2 R 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 group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (vi)-(CH 2 ) n- CO 2 R 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 group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (vii)-(CH 2 ) n- CH=CH-CO 2 R 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 group, an optionally substituted C 1~20a bond to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascarylose molecule or a bond through a carbon-containing linker moiety), (viii)-(CH 2 ) n- CH(OH)-CH-CO 2 R 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 group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond through a carbon-containing linker moiety), and (ix)-(CH 2 ) n- C(O)-CH-CO 2 R 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 group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond through a carbon-containing linker moiety), and is selected from the group consisting of, the composition according to embodiment 69.

[0078] Embodiment 71: Z is (x)-CH(CH 3 )-(CH 2 ) n -CON(R 3 ) 2 , (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20a bond to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascarylose molecule or a bond via a carbon-containing linker moiety), (xi)-CH(CH 3 )-(CH 2 ) n- CH=CH-CON(R 3 ) 2 , (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (xii)-CH(CH 3 )-(CH 2 ) n- CH(OH)-CH-CON(R 3 ) 2 , (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), (xiii)-CH(CH 3 )-(CH 2 ) n- C(O)-CH-CON(R 3 ) 2 , (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20a bond to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascarylose molecule or a bond through a carbon-containing linker moiety), (xiv)-(CH 2 ) n- CON(R 3 ) 2 , (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a bond to a polymer chain, an amino acid, a peptide, a nucleotide, or another ascarylose molecule or a bond through a carbon-containing linker moiety), (xv)-(CH 2 ) n- CH=CH-CON(R 3 ) 2 , (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a bond to a polymer chain, an amino acid, a peptide, a nucleotide, or another ascarylose molecule or a bond through a carbon-containing linker moiety), (xvi)-(CH 2 ) n- CH(OH)-CH-CON(R 3 ) 2 , (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a bond to a polymer chain, an amino acid, a peptide, a nucleotide, or another ascarylose molecule or a bond through a carbon-containing linker moiety), and (xvii)-(CH 2 ) n- C(O)-CH-CON(R 3 )2 (wherein n is an integer from 1 to 40, and each R 3 is independently selected from the group consisting of -H, optionally substituted C 1~20 aliphatic group, optionally substituted C 1~20 heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or a bond to another ascarylose molecule or a bond via a carbon-containing linker moiety), the composition according to claim 69.

[0079] Embodiment 72: R a and R b are each -H, the composition according to any one of embodiments 69 to 71.

[0080] Embodiment 73: Z is -CH(CH 3 )-(CH 2 ) n- CO 2 R 2 where n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide, the composition according to any one of embodiments 69 to 72.

[0081] Embodiment 74: The composition according to any one of embodiments 44 to 68, wherein the one or more ascarylose contains ascr#18.

[0082] Embodiment 75: The composition according to any one of embodiments 44 to 74 in solid form.

[0083] Embodiment 76: The composition according to embodiment 75, wherein the solid form contains powder or granules.

[0084] Embodiment 77: The composition according to any one of embodiments 44 to 74 in liquid form.

[0085] Embodiment 78: The composition according to embodiment 77, wherein the liquid form is a sprayable formulation.

[0086] Embodiment 79: The composition according to embodiment 77 or 78, wherein the composition is storage stable for a period exceeding 6 months or exceeding 12 months.

[0087] Embodiment 80: The composition according to any one of embodiments 44 to 79, further comprising one or more additional components selected from the group consisting of surfactants composed of emulsifiers, dispersants, foam formers, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, ultraviolet absorbers, weather stabilizers, plasticizers, release agents, fragrances, heat preservation additives (for example, silica), crosslinking agents, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, extenders / adhesives, tackifiers, plant penetrants, toxicity moderators, spreading agents, and wetting agents.

[0088] Embodiment 81: The composition according to any one of embodiments 44 to 80, wherein the fungicide and the ascarylose are present in a weight ratio of fungicide:ascarylose exceeding 1000:1, exceeding 1500:1, exceeding 2000:1, exceeding 3000:1, exceeding 5000:1, or exceeding 10,000:1.

[0089] Embodiment 82: The composition according to any one of embodiments 44 to 81, which is labeled for application to crops at a rate lower than the labeled rate of the fungicide alone.

[0090] Embodiment 83: The composition according to any one of embodiments 44 to 82, which is labeled for application to crops at a rate delivering less than 4 oz, less than 3 oz, or less than 2.5 oz of fungicide per acre.

[0091] These and other features, aspects, and advantages of the present disclosure will become apparent from the following detailed description when read in conjunction with the accompanying drawings described briefly below. The invention includes any combination of two, three, four or more of the above-described embodiments, as well as any combination of two, three, four or more features or elements described in the present disclosure, whether or not such features or elements are explicitly combined in a particular embodiment herein. The present disclosure is to be read as a whole such that any separable features or elements of the disclosed invention may be combined in any of its various aspects and embodiments, unless the context clearly indicates otherwise. Other aspects and advantages of the present disclosure will become apparent from the following.

[0092] The teachings described herein will be more fully understood from the following description of various exemplary embodiments when read in conjunction with the accompanying drawings. It is to be understood that each of the drawings described below is for purposes of illustration only and is not intended to limit the scope of the teachings in any way. The foregoing and other objects, aspects, features, and advantages of the present disclosure will become more apparent and better understood by referring to the following description in conjunction with the accompanying drawings.

Brief Description of the Drawings

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[0111] **Definitions** For easier understanding of the present disclosure, certain terms are first defined below. Further definitions of the following terms and other terms are set forth throughout this specification.

[0112] Unless otherwise clearly defined from the context, the term "a" can be understood to mean "at least one" in this application. When used in this application, the term "or" can be understood to mean "and / or". In this application, the terms "comprising" and "including" can be understood to encompass the components or steps listed item by item, whether shown by themselves only or together with one or more additional components or steps. When used in this application, the term "comprise", as well as variations of this term such as "comprising" and "comprises", are not intended to exclude other additives, components, integers or steps.

[0113] As used herein, the terms "about" and "approximately" are used as equivalents. Unless otherwise specified, the terms "about" and "approximately" can be understood to allow for a standard deviation, as understood by one of ordinary skill in the art. When ranges are provided herein, endpoints are included. Regardless of whether there is an "about" or "approximately", any numbers used in this application are meant to cover any normal variations understood by one of ordinary skill in the relevant technical field. In some embodiments, the term "approximately" or "about" refers to a value within 25%, 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, or less of the stated standard reference value in either direction (greater or less), unless otherwise stated or clear from the context (except when such a number exceeds 100% of the possible values).

[0114] The definitions of specific functional groups and chemical terms are described in more detail below. For the purposes of the present invention, chemical elements are based on The Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75 thEd., identified according to the inside cover, and specific functional groups are generally defined as described therein. In addition, general principles of organic chemistry, as well as specific functional moieties and reactivities, are described in Organic Chemistry, Thomas Sorrell, University Science Books, Sausalito, 1999, Smith and March March’s Advanced Organic Chemistry, 5 th 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, 3 rd Edition, Cambridge University Press, Cambridge, 1987, and the entire contents of each are hereby incorporated by reference into this specification.

[0115] The specific compounds provided herein can contain one or more asymmetric centers and can therefore exist in various stereoisomeric forms, such as enantiomers and / or diastereomers. Accordingly, the compounds of the invention and their compositions can be in the form of individual enantiomers, diastereomers or geometric isomers, or in the form of mixtures of stereoisomers. In certain embodiments, the compounds described herein are enantiopure compounds. In certain other embodiments, mixtures of enantiomers or diastereomers are provided.

[0116] Furthermore, the specific compounds described herein may have one or more double bonds that can exist as either the Z or E isomer, unless otherwise indicated. The compounds can be provided as individual isomers substantially free of other isomers and, alternatively, as mixtures of various isomers, such as racemic mixtures of enantiomers.

[0117] As used herein, the term "isomer" includes any and all geometric and stereoisomers. For example, "isomer" includes cis and trans isomers, E and Z isomers, R and S isomers, diastereomers, (d)-isomers, (l)-isomers, racemic mixtures thereof, as well as other mixtures thereof, as long as they are within the scope of the present disclosure. For example, in some embodiments, the compounds may be provided substantially free of one or more corresponding stereoisomers and may be referred to as "stereochemically enriched."

[0118] When a particular enantiomer is preferred, in some embodiments, it may be provided substantially free of the opposite enantiomer and may be referred to as "optically enriched." As used herein, "optically enriched" means that the compounds of the invention are composed of a significantly higher proportion of one enantiomer. In certain embodiments, the compound is composed of at least about 90% by weight of one 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 one enantiomer. In some embodiments, the enantiomeric excess of the compound provided is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8% or 99.9%. In some embodiments, the enantiomers may be separated from the racemic mixture by any well-known method such as chiral high performance liquid chromatography (HPLC) as well as the formation and crystallization of chiral salts, or may be prepared by asymmetric synthesis. See, for example, Jacques, et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981), Wilen, S.H., et al., Tetrahedron 33:2725 (1977), Eliel, E.L. Stereochemistry of Carbon Compounds (McGraw-Hill, NY, 1962), Wilen, S.H. Tables of Resolving Agents and Optical Resolutions p.268 (E.L. Eliel, Ed., Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0119] As used herein, the terms "halo" and "halogen" refer to an atom selected from fluorine (fluoro, -F), chlorine (chloro, -Cl), bromine (bromo, -Br), and iodine (iodo, -I).

[0120] As used herein, the term "aliphatic" or "aliphatic group" refers to a hydrocarbon moiety that can be linear (i.e., unbranched), branched, or cyclic (including fused, bridged, and spiro-fused polycyclic), can be completely saturated, or can contain one or more units of unsaturation, but is not aromatic. Unless otherwise specified, aliphatic groups contain from 1 to 30 carbon atoms. In certain embodiments, aliphatic groups contain from 1 to 12 carbon atoms. In certain embodiments, aliphatic groups contain from 1 to 8 carbon atoms. In certain embodiments, aliphatic groups contain from 1 to 6 carbon atoms. In some embodiments, aliphatic groups contain from 1 to 5 carbon atoms, in some embodiments, aliphatic groups contain from 1 to 4 carbon atoms, in still other embodiments, aliphatic groups contain from 1 to 3 carbon atoms, and in still other embodiments, aliphatic groups contain from 1 to 2 carbon atoms. Suitable aliphatic groups include, but are not limited to, linear or branched alkyl, alkenyl, and alkynyl, and hybrids thereof such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl.

[0121] As used herein, the term "heteroaliphatic" or "heteroaliphatic group" refers to an aliphatic group in which one or more carbon atoms or hydrogen atoms have been replaced by heteroatoms (e.g., oxygen, nitrogen, sulfur, phosphorus, boron, etc.).

[0122] As used herein, the term "unsaturated" means that the moiety has one or more double or triple bonds.

[0123] As used herein, the term "alkyl" refers to a saturated, straight-chain or branched-chain hydrocarbon radical derived from an aliphatic moiety containing 1 to 6 carbon atoms by removal of one hydrogen atom. Unless otherwise specified, an alkyl group contains 1 to 12 carbon atoms. In certain embodiments, an alkyl group contains 1 to 8 carbon atoms. In certain embodiments, an alkyl group contains 1 to 6 carbon atoms. In some embodiments, an alkyl group contains 1 to 5 carbon atoms, in some embodiments, an alkyl group contains 1 to 4 carbon atoms, in still other embodiments, an alkyl group contains 1 to 3 carbon atoms, and in still other embodiments, an alkyl group contains 1 to 2 carbon atoms. Examples of alkyl radicals include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, sec-pentyl, iso-pentyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, n-decyl, n-undecyl, dodecyl, and the like.

[0124] As used herein, the term "alkenyl" refers to a monovalent group derived from a straight-chain or branched-chain aliphatic moiety having at least one carbon-carbon double bond by removal of one hydrogen atom. Unless otherwise specified, an alkenyl group contains 2 to 12 carbon atoms. In certain embodiments, an alkenyl group contains 2 to 8 carbon atoms. In certain embodiments, an alkenyl group contains 2 to 6 carbon atoms. In some embodiments, an alkenyl group contains 2 to 5 carbon atoms, in some embodiments, an alkenyl group contains 2 to 4 carbon atoms, in still other embodiments, an alkenyl group contains 2 to 3 carbon atoms, and in still other embodiments, an alkenyl group contains 2 carbon atoms. Examples of alkenyl groups include, for example, ethenyl, propenyl, butenyl, 1-methyl-2-buten-1-yl, and the like.

[0125] The term "aryl", when used alone or as part of a larger moiety, such as "aralkyl", "aralkoxy", or "aryloxyalkyl", refers to monocyclic and polycyclic ring systems having a total of 5 to 20 ring members, at least one ring in the system being aromatic, and each ring in the system containing 3 to 12 ring members. The term "aryl" may be used interchangeably with the term "aryl ring". In certain embodiments, "aryl" refers to aromatic ring systems including, but not limited to, phenyl, biphenyl, naphthyl, anthracyl, etc., which may have one or more substituents. Also, as used herein 「 the scope of the term "aryl" includes groups in which the aromatic ring is fused to one or more additional rings such as benzofuranyl, indanyl, phthalimidyl, naphthimidyl, phenanthridinyl, or tetrahydronaphthyl.

[0126] As described herein, the compounds provided herein may contain "optionally substituted" moieties. In general, the term "substituted", whether or not preceded by the term "optionally", means that one or more hydrogens of the designated moiety are replaced by a suitable substituent. Unless otherwise specified, an "optionally substituted" group may have suitable substituents at each substitutable position of the group, and when two or more positions in any given structure may be substituted with two or more substituents selected from the recited groups, the substituents may be the same or different at each position. The combinations of substituents envisioned are preferably those that result in the formation of stable or chemically possible compounds. As used herein, the term "stable" refers to compounds that do not substantially change when subjected to conditions that allow for their manufacture, detection, and in certain embodiments, their recovery, purification, and use for one or more of the purposes disclosed herein.

[0127] Suitable monovalent substituents on a substitutable carbon atom of an "optionally substituted" group are, independently, halogen, -(CH 2 ) 0~4 R°, -(CH 2 )0~4 OR°, -O-(CH 2 ) 0~4 C(O)OR°, -(CH 2 ) 0~4 CH(OR°) 2 、-(CH 2 ) 0~4 SR°, -(CH 2 ) 0~4 Ph (which may be substituted by R°), -(CH 2 ) 0~4 O(CH 2 ) 0~1 Ph (which may be substituted by R°), -CH=CHPh (which may be substituted by R°), -NO 2 、-CN、-N 3 、-(CH 2 ) 0~4 N(R°) 2 、-(CH 2 ) 0~4 N(R°)C(O)R°, -N(R°)C(S)R°, -(CH 2 ) 0~4 N(R°)C(O)NR° 2 、-N(R°)C(S)NR° 2 、-(CH 2 ) 0~4 N(R°)C(O)OR°, -N(R°)N(R°)C(O)R°, -N(R°)N(R°)C(O)NR° 2 、-N(R°)N(R°)C(O)OR°, -(CH 2 ) 0~4 C(O)R°, -C(S)R°, -(CH 2 ) 0~4 C(O)OR°, -(CH 2 ) 0~4 C(O)N(R°) 2 、-(CH 2 ) 0~4 C(O)SR°, -(CH 2 ) 0~4 C(O)OSiR° 3 、-(CH 2 ) 0~4 OC(O)R°, -OC(O)(CH 2 ) 0~4 SR-, SC(S)SR°, -(CH 2 ) 0~4 SC(O)R°, -(CH 2 )0~4 C(O)NR° 2 、 -C(S)NR° 2 、 -C(S)SR°、 -SC(S)SR°、 -(CH 2 ) 0~4 OC(O)NR° 2 、 -C(O)N(OR°)R°、 -C(O)C(O)R°、 -C(O)CH 2 C(O)R°、 -C(NOR°)R°、 -(CH 2 ) 0~4 SSR°、 -(CH 2 ) 0~4 S(O) 2 R°、 -(CH 2 ) 0~4 S(O) 2 OR°、 -(CH 2 ) 0~4 OS(O) 2 R°、 -S(O) 2 NR° 2 、 -(CH 2 ) 0~4 S(O)R°、 -N(R°)S(O) 2 NR° 2 、 -N(R°)S(O) 2 R°、 -N(OR°)R°、 -C(NH)NR° 2 、 -P(O) 2 R°、 -P(O)R° 2 、 -OP(O)R° 2 、 -OP(O)(OR°) 2 、 SiR° 3 、 -(C 1~4 straight-chain or branched alkylene)O-N(R°) 2 、 or -(C 1~4 straight-chain or branched-chain alkylene)C(O)O-N(R°) 2 and each R° may be substituted as defined below and is independently hydrogen, C 1~8 aliphatic, -CH 2 Ph, -O(CH 2 ) 0~1 Ph, or independently selected from nitrogen, oxygen, or sulfur 0 ~A 5- to 6-membered saturated, partially unsaturated, or aryl ring having 4 heteroatoms, or, regardless of the above definition, two independent occurrences of R° together with any intervening atom(s) form a 3- to 12-membered saturated, partially unsaturated, or aryl monocyclic or polycyclic ring having 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, and may be substituted as defined below.

[0128] Suitable monovalent substituents on R° (or the ring formed by taking two independent occurrences of R° together with their intervening atoms) are independently halogen, -(CH 2 ) 0~2 R ● , -(haloR ● ), -(CH 2 ) 0~2 OH, -(CH 2 ) 0~2 OR ● , -(CH 2 ) 0~2 CH(OR ● ) 2 , -O(haloR ● ), -CN, -N 3 , -(CH 2 ) 0~2 C(O)R ● , -(CH 2 ) 0~2 C(O)OH, -(CH 2 ) 0~2 C(O)OR ● , -(CH 2 ) 0~4 C(O)N(R°) 2 , -(CH 2 ) 0~2 SR ● , -(CH 2 ) 0~2 SH, -(CH 2 ) 0~2 NH 2 , -(CH 2 ) 0~2 NHR ● , -(CH 2 ) 0~2 NR ● 2 , -NO 2 , -SiR● 3 ,-OSiR ● 3 ,-C(O)SR ● 、 -(C 1~4 linear or branched alkylene)C(O)OR ● , or -SSR ● wherein each R ● is unsubstituted or, when preceded by "halo", substituted only with one or more halogens and is independently selected from C 1~4 aliphatic, -CH 2 Ph, -O(CH 2 ) 0~1 Ph, or is independently selected from 5- to 6-membered saturated, partially unsaturated, or aryl rings having 0 to 4 heteroatoms selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents on the saturated carbon atoms of R° include =O and =S.

[0129] Suitable divalent substituents on the saturated carbon atoms of a "optionally substituted" group include =O, =S, =NNR * 2 , =NNHC(O)R * , =NNHC(O)OR * , =NNHS(O) 2 R * , =NR * , =NOR * , -O(C(R * 2 )) 2-3 O-, or -S(C(R * 2 )) 2-3 S-, where each independent occurrence of R * is hydrogen, C 1~6 aliphatic which may be substituted as defined below, or is selected from unsubstituted 5- to 6-membered saturated, partially unsaturated, or aryl rings having 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents bonding to a substitutable carbon proximal to an "optionally substituted" group include -O(CR * 2 ) 2~3 O-, where each R *Each independent occurrence may be hydrogen, C which may be substituted as defined below 1~6 selected from an aliphatic group, or an unsubstituted 5- to 6-membered saturated, partially unsaturated, or aryl ring having from 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0130] R * Suitable substituents on the aliphatic group of R include halogen, -R ● , -(haloR ● ), -OH, -OR ● , -O(haloR ● ), -CN, -C(O)OH, -C(O)OR ● , -NH 2 , -NHR ● , -NR ● 2 , or -NO 2 ● 1~4 where each R is unsubstituted or, when "halo" precedes, substituted only with one or more halogens and independently is a C 2 aliphatic group, -CH 2 Ph, -O(CH 0~1 ) † Ph, or a 5- to 6-membered saturated, partially unsaturated, or aryl ring having from 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0131] Suitable substituents on the nitrogen of a "optionally substituted" group include -R † , -NR † 2 , -C(O)R † , -C(O)OR † , -C(O)C(O)R † , -C(O)CH 2 C(O)R † , -S(O) 2 R † , -S(O) 2 NR † 2 , -C(S)NR † 2 , -C(NH)NR † 2 , or -N(R † )S(O)2 R † includes, each R † is independently hydrogen, C 1~6 aliphatic which may be substituted as defined below, unsubstituted -OPh, or an unsubstituted 5- to 6-membered saturated, partially unsaturated, or aryl ring having from 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or, regardless of the above definition, two independent occurrences of R † together with the intervening atom(s) therebetween form an unsubstituted 3- to 12-membered saturated, partially unsaturated, or aryl monocyclic or bicyclic ring having from 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0132] R † Suitable substituents on the aliphatic group of R ● are independently halogen, -R ● , -(haloR ● ), -OH, -OR ● , -O(haloR ● ), -CN, -C(O)OH, -C(O)OR 2 , -NH ● , -NHR ● 2 , or -NO 2 , where R ● is unsubstituted or, when preceded by "halo", is substituted by only one or more halogens and is independently C 1~4 aliphatic, -CH 2 Ph, -O(CH 2 ) 0~1 Ph, or a 5- to 6-membered saturated, partially unsaturated, or aryl ring having from 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0133] As used herein, the term "substantially" refers to a qualitative condition indicating the entire degree or almost the entire degree or degree of a characteristic or property of an object.

[0134] Ascalosides are named with a few-letter prefix followed by the pound sign (#), and there is a convention of using numbers (e.g., ascr#18). This convention is used in the scientific literature, and those skilled in the art will understand that each such name is associated with the specific chemical structure of a known composition and will immediately understand the structure of the molecule denoted using this nomenclature. Unless otherwise indicated, all compound identifiers of this form used herein conform to the definitions described in the C. elegans Small Molecule Identifier Database (SMID-DB) maintained at http: / / www.smid-db.org.

[0135] The term "pathogen" refers to any bacterium, fungus, oomycete, virus, nematode (e.g., cyst or root knot nematode), or insect that has a pathogenic effect on plants.

[0136] Provided are compositions and methods for the use of ascaryosides. The present disclosure relates to the treatment of plants with one or more ascaryosides and one or more additional active agents (e.g., fungicides or other antimicrobial agents). In certain embodiments, the present disclosure provides a combination of one or more naturally occurring ascaryosides (having a biological origin and having a mode of action that classifies them as biological products (e.g., biopesticides)) and one or more synthetic chemical fungicides. The co-application of biological products and chemical fungicides often results in a decrease in the activity of the biological product or causes other issues related to the physical or chemical incompatibility of the biological and chemical formulations, or the requirements of different application timings or methods. In certain embodiments, the application of the provided biological / synthetic combination is surprisingly stable and exhibits unexpected additive or synergistic effects considering the very different modes of action and application rates. Specific 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, the treatment can be carried out via separate application of one or more ascaryosides and one or more additional active agents, or via a composition comprising both one or more ascaryosides and one or more additional active agents. In some embodiments, one or more ascaryosides and one or more additional active agents exhibit synergistic effects.

[0137] Ascaryoside Ascaryosides are derivatives of the sugar ascarylose, which is a dideoxy sugar lacking hydroxyl groups at its 3- and 6-positions. Ascaryosides have the general structure shown in Formula I:

Chemical formula

[0138] In certain embodiments, Z is (i) -CH(CH 3 )-R 1 (R 1 is an optionally substituted C 1~40 aliphatic group), (ii) -CH(CH 3 )-(CH 2 ) n- CO 2 R 2(n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), (iii) -CH(CH 3 )-(CH 2 ) n- CH=CH-CO 2 R 2 (n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), (iv) -CH(CH 3 )-(CH 2 ) n- CH(OH)-CH-CO 2 R 2 (n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), (v) -CH(CH 3 )-(CH 2 ) n- C(O)-CH-CO 2 R 2 (n is an integer from 1 to 40, and R 2 is, -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C1~20 a bond to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascarylose molecule, or a linkage via a carbon-containing linker moiety), (vi) -(CH 2 ) n- CO 2 R 2 (where n is an integer from 1 to 40 and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), (vii) -(CH 2 ) n- CH=CH-CO 2 R 2 (where n is an integer from 1 to 40 and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), (viii) -(CH 2 ) n- CH(OH)-CH-CO 2 R 2 (where n is an integer from 1 to 40 and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), or (ix) -(CH2 ) n- C(O)-CH-CO 2 R 2 (n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascaryoside molecule or a linkage via a carbon-containing linker moiety).

[0139] In certain embodiments, Z is (x) -CH(CH 3 )-(CH 2 ) n- CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascaryoside molecule or a linkage via a carbon-containing linker moiety), (xi) -CH(CH 3 )-(CH 2 ) n- CH=CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascaryoside molecule or a linkage via a carbon-containing linker moiety), (xii) -CH(CH 3 )-(CH 2 ) n-CH(OH)-CH-CON(R 3 ) 2 (wherein n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety); (xiii) -CH(CH 3 )-(CH 2 ) n- C(O)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), (xiv) -(CH 2 ) n- CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), (xv) -(CH 2 ) n- CH=CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20An aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), (xvi) -(CH 2 ) n- CH(OH)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety), or (xvii) -(CH 2 ) n- C(O)-CH-CON(R 3 ) 2 (n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C 1~20 aliphatic group, an optionally substituted C 1~20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety).

[0140] In certain embodiments, R a is -H.

[0141] In certain embodiments, R b is -H.

[0142] In certain embodiments, a and R b are the same. In certain embodiments, R a and R bBoth are -H.

[0143] In certain embodiments, R a and R b are different. In certain embodiments, R a is -H and R b is other than -H. In certain embodiments, R a is other than -H and R b is -H. In certain embodiments, R a is -H and R b is p-hydroxybenzoate. In certain embodiments, R a is -H and R b is indole-3-carboxylate. In certain embodiments R a is -H and R b is (E)-2-methyl-2-butenoate. In certain embodiments, R a is -H and R b is picolinate. In certain embodiments, R a is -H and R b is nicotinate. In certain embodiments, R a is -H and R b is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, R a is -H and R b is 4-((4-hydroxyphenylethyl)amino)-4-oxobutanoate.

[0144] In certain embodiments, R a and R b are both -H and Z is selected from the formulas defined in (i)-(xvii) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (i) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (ii) above. In certain embodiments, R a and Rb are both -H, and Z conforms to the above formula (iii). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (iv). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (v). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (vi). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (vii). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (viii). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (ix). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (x). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (xi). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (xii). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (xiii). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (xiv). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (xv). In certain embodiments, R a and R b are both -H, and Z conforms to the above formula (xvi). In certain embodiments, R a and R bBoth are -H, and Z conforms to the above formula (xvii).

[0145] 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 cationic group centered on nitrogen or phosphorus). In certain embodiments, R 2 is an optionally substituted C 1~20 aliphatic group. In certain embodiments, R 2 is an optionally substituted C 1~12 aliphatic group. In certain embodiments, R 2 is an optionally substituted C 1~8 aliphatic group. In certain embodiments, R 2 is an optionally substituted C 1~6 aliphatic group. In certain embodiments, R 2 is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In certain embodiments, R 2 is an optionally substituted aromatic group. In certain embodiments, R 2 is a glycoside. In certain embodiments, R 2 contains an amino acid. In certain embodiments, R 2 contains a peptide. In certain embodiments, R 2 contains a nucleotide.

[0146] In certain embodiments, at least one R 3 is -H. In certain embodiments, both R 3 groups are -H. In certain embodiments, at least one R 3 is an optionally substituted C 1~20 aliphatic group. In certain embodiments, both R 3 groups may be the same or different, and are optionally substituted C 1~20 aliphatic groups. In certain embodiments, at least one R 3 is an optionally substituted C1~12 It is an aliphatic group. In certain embodiments, at least one R 3 is an optionally substituted C 1~8 aliphatic group. In certain embodiments, at least one R 3 is an optionally substituted C 1~6 aliphatic group. In certain embodiments, at least one R 3 is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In certain embodiments, at least one R 3 is -CH 2 CH 2 OH. In certain embodiments, at least one R 3 is -CH 2 CH 2 OR 2 wherein R 2 is as defined in the genera and subgenera of this specification. In certain embodiments, at least one R 3 is an optionally substituted aromatic group. In certain embodiments, at least one R 3 contains a glycoside. In certain embodiments, at least one R 3 contains an amino acid. In certain embodiments, at least one R 3 contains a peptide. In certain embodiments, at least one R 3 contains a nucleotide.

[0147] In certain embodiments, the ascarioside is

Chemical formula

[0148] In certain embodiments, the ascarioside is

Chemical formula

[0149] In certain embodiments, the ascaloside is

Chemical formula

[0150] In certain embodiments, the ascaloside is

Chemical formula

[0151] In certain embodiments, the ascaloside is

Chemical formula

[0152] In certain embodiments, the ascaloside is

Chemical formula

[0153] In certain embodiments, the ascaloside is

Chemical formula

[0154] In certain embodiments, the ascaloside is

Chemical formula

[0155] In certain embodiments, the ascaloside is

Chemical formula

[0156] In certain embodiments, the ascaloside is

Chemical formula

[0157] In certain embodiments, the ascaloside is

Chemical formula

[0158] In certain embodiments, the ascaloside is [Chemical formula] selected from the group consisting of, wherein y and R 3 are each as defined in the genera and subgenera above and in this specification.

[0159] In one embodiment, the ascaloside useful in the context of the present disclosure has the general structure (I), wherein Z is -CH(CH 3 )-(CH 2 ) n- CO 2 R 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 group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide, and can be used to inhibit the growth of human pathogenic bacteria in or on plants.

[0160] In one embodiment, the ascaloside useful in the context of the present disclosure has the general structure (I), wherein Z is -CH(CH 3 )-(CH 2 ) n- CH=CH-CO 2 R 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 group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0161] Specific ascalosides useful in the context of the present disclosure include, but are not limited to, ascr#7 and ascr#18. [Chemical formula]

[0162] 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.

[0163] In certain embodiments, the ascarosides used in the provided methods and compositions are 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 ascarosides used in the provided methods are selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22. In certain embodiments, the ascarosides used in the provided methods are 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 ascarosides used in the provided methods are selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

[0164] In certain embodiments, the ascaloside used in the provided methods and compositions is selected from the group consisting of bhas#9, bhas#10, bhas#16, bhas#18, bhas#22, bhas#24, bhas#26, bhas#28, bhas#30, bhas#32, bhas#34, bhas#36, bhas#38, bhas#40, and bhas#42.

[0165] In certain embodiments, the ascaloside used in the provided methods and compositions is selected from the group consisting of bhos#10, bhos#16, bhos#18, bhos#22, bhos#24, bhos#26, bhos#28, bhos#30, bhos#32, bhos#34, bhos#36, bhos#38, bhos#40, and bhos#42.

[0166] In certain embodiments, the ascaloside used in the provided methods and compositions is selected from the group consisting of ascr#18, oscr#16, oscr#17, oscr#15, bhas#18, bhos#16, glas#18, dhas#18, ibha#18, ibho#16, icas#18, icos#15, icos#16, and any combination of two or more thereof.

[0167] In some embodiments, the ascaloside used in the provided methods and compositions is an ascaloside salt disclosed in International Application No. PCT / US2023 / 21731, filed May 10, 2023, or an ascaloside modified to provide extended release of the active ingredient disclosed in International Application No. PCT / US2023 / 20472, filed April 28, 2023, both of which are hereby incorporated by reference in their entirety.

[0168] Ascalarosides can be obtained from natural sources (e.g., nematodes) or prepared synthetically. Ascalarosides can be prepared synthetically, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascarylose. Exemplary methods for preparing ascalarosides include providing 1-O-substituted rhamnose as a starting material, forming a monosulfonate ester at the 3-OH group of the starting material, and treating the monosulfonate ester with a hydride source to form 1-O-substituted ascarylose. In certain embodiments, the formation of the monosulfonate ester is carried out on a substrate that does not contain a hydroxyl protecting group at the 2- or 4-position of the rhamnose starting material. In certain embodiments, such methods include contacting the starting 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 regarding the synthesis of 1-O-substituted ascarylose can be found in PCT Application Publication No. WO / 2022 / 024067, which is incorporated herein by reference.

[0169] Additional active agents One or more additional active agents in the various methods and compositions provided herein include all compounds understood to exhibit beneficial activity against one or more pathogens. Such active agents are generally antibacterial agents and include, but are not limited to, antibacterial agents (also referred to as bactericides), antifungal agents (also referred to as fungicides), insecticidal agents (also referred to as insecticides), and anthelmintic agents (also referred to as nematicides).

[0170] The antibacterial agents useful in the methods and formulations of the present disclosure are not particularly limited. Suitable active agents may be prophylactic or curative, may have single-site or multi-site activity, may in fact be narrow-spectrum or broad-spectrum, and may be organic or inorganic. They may be chemical or biological. In some embodiments, the active agent is a natural one having active ingredients including, but not limited to, sulfur, lime-sulfur, copper (e.g., in the form of copper sulfate), oils (e.g., horticultural oils, neem oil, rosemary oil, and jojoba oil), bicarbonates (e.g., sodium bicarbonate, potassium bicarbonate, and ammonium bicarbonate), and combinations thereof.

[0171] Certain broad chemical classes of suitable fungicidal compounds useful in certain embodiments as disclosed herein include, but are not limited to, substituted benzenes, thiocarbamates, dithiocarbamates, thiophthalimide copper compounds, nitriles / benzonitriles / chloronitriles, benzimidazoles, dicarboximides, carboxamides / anilides, strobilurins, phenylpyrroles, aromatic hydrocarbons, polyoxins, pyridineamines, phenylamides, cyanoimidazoles, phosphonates, and combinations thereof. The fungicides useful in the various formulations and methods described herein can also be defined, for example, by modes of action such as: mitotic disruptors (e.g., thiophanates such as thiophanate-methyl); cell membrane disruptors (e.g., triazoles such as cyproconazole, difenoconazole, flutriafol, mefenentrifluconazole, metconazole, propiconazole, tebuconazole, and tetraconazole, and triazolinethiones such as prothioconazole); respiratory inhibitors (e.g., succinate dehydrogenase inhibitors / carboxamides, such as pyridinecarboxamides (e.g., boscalid), pyridinyl-ethylbenzamides (e.g., fluopyram), and pyrazole-4-carboxamides (e.g., benzovindiflupyr, bixafen, fluxapyroxad, penthiopyrad, pydiflumetofen), and quinone outside inhibitors / strobilurins, such as methoxyacrylates (e.g., azoxystrobin and picoxystrobin), dihydro-dioxazines (e.g., fluoxastrobin), methoxy-carbamates (e.g., pyraclostrobin), and oxyimino-acetates (e.g., trifloxystrobin)); uncouplers of oxidative phosphorylation (e.g., 2,6-dinitroanilines such as fluazinam); fungicides of unknown activity (e.g., phosphonates such as phosphoric acid and salts); and fungicides having multi-site contact activity (e.g., inorganic fungicides such as copper salts and chloronitriles / phalonitriles such as chlorothalonil).

[0172] Suitable specific additional activators include acibenzolar, acibenzolar-S-methyl, Agrobacterium radiobacter, aldicarb, aliphatic petroleum distillates, allyl isothiocyanate, aluminum tris, ametoctradin, 2-aminobutane, Ampelomyces quisqualis, anilazine, Aureobasidium pullulans (e.g., strains DSM14940 and 14941), azadirachtin, azoxystrobin, Bacillus amyloliquefaciens (e.g., strain D747 or F727), Bacillus firmus (e.g., strain I-1582), Bacillus mycoides (e.g., isolate J), Bacillus pumilus (e.g., strain QST2808), Bacillus subtilis (e.g., strain IAB / BS03, strain QST713, strain BG03 strain, or strain MBI600), basic cupric carbonate, benomyl, benzovindiflupyr, bifenazate, bixafen, BLAD, borax, boric acid, boscalid, Burkholderia cepacia, Candida oleophila, capric acid and caprylic acid, captan, captan, carbendazim, carbofuran, carbon disulfide, carboxin, chitin, chlorfenapyr, chlorine dioxide, chloroneb, chloropicrin, chlorothalonil, cinnamaldehyde, cyproconazole, clove oil, Coniothyriumminitans (e.g., CON / M / 91-08), copper, copper ammonium complex (e.g., copper ammonium carbonate, tannic acid complex of cupric picrate ammonium), copper diamine diacetate complex, copper hydroxide, copper octoate, copper oxide, copper oxychloride, copper sulfate, cresol, cyazofamid, cyclohexane polymer, cycloheximide, cymoxanil, cyproconazole, cyprodinil, dazomet, decab, diclone, dichloran, dichloropropene, dicofol, difenoconazole, difenzooxazole, diafenthion, dimethomorph, demeton, dimethyl disulfide, dinocap, dodemorph acetate, dodine, epoxyconazole, ethaboxam, ethoprop, ethoxyquin, ethylene dibromide, ethaboxam, etridiazole, famoxadone, fenamidone, fenaminosulf, fenamiphos, fenarimol, fenazaquin, fenbuconazole, fenhexamid, fenpyrazamine, fensulfothion, ferbam, fluazinam, fluazinam, fluopicolide, fluopyram, fluoxastrobin, flusilazole, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl-Al, gamma aminobutyric acid, gibberellic acid, Gliocladium catenalatum (e.g., strain J1446), Gliocladium viren, harpin, hexachlorobenzene, horticultural mineral oil, calcium hydroxide, hymexazol, imazalil, iodomethane, ipconazole, iprodione, isfetamid, jojoba oil, kasugamycin, kresoxim-methyl, L-glutamic acid, laminarin, lime sulfur mixture, mandestrobin, mandipropamid, maneb, mancozeb, mefenoxam, mefentrifluconazole, metalaxyl, metam sodium, metconazole, methyl bromide, methylcyclopropene, methyl isothiocyanate, metrafenone, methyl bromide, methylcyclopropene, methalaxyl, microbutanyl, MyrotheciumVerrucaria (e.g., strain AARC-0255), neem oil, oxydixyl, oxamyl, oxythioquinox, oxathiapiprolin, oxycarboxin, oxytetracycline, oxythioquinox, Paecilomyces lilacinus (e.g., strain 251), Pantoea agglomerans (e.g., strain E325), parinol, pentachloronitrobenzene (PCNB), penthiopyrad, peroxide, peroxyacetic acid, hydroperoxide, petroleum, phenylmercury acetate, phosphite, 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 chlororaphis (e.g., strain AFS009), Pseudomonas fluorescens, Pseudomonas syringae, pidiflumetofen, pyraclostrobin, pyrimethanil, pyrifenone, quaternary ammonium, quinoxyfen, Reynoutria sachalinensis, rosemary oil, saponin, sedaxane, sodium hypochlorite, spiroxamine, Streptomyces griseoviridis (e.g., strain 61), streptomycin, sulfur, Swinglea glutinosa, tebuconazole, tetrathiolcarbonate, thiabendazole, thiamethoxam, thiophanate, thiophanate-methyl, thiram, thyme oil, triadimefon, triadimenol, Trichoderma asperellum (e.g., strain T34), Trichoderma gamsii, Trichoderma harzianum, trifloxystrobin, triflumazole, trifolin, triphenyltin hydroxide, triticonazole, urea, Urocladium oudemansii (e.g., U3 strain), vinclozolin, waniracin, xylenol, dinneb, dithiram, zoxamide, and combinations thereof, including but not limited to these.

[0173] In some embodiments, one or more ascalosides are combined with one or more commercially available antibacterial agents, such as one or more fungicides. In some embodiments, such commercially available antibacterial agents are bactericidal mixtures. Commercially available antibacterial agents are known in the art and include ABOUND® (Syngenta) containing azoxystrobin, ABSOLUTE® (Bayer Crop Science) containing tebuconazole and trifloxystrobin, ACADEMY® (Syngenta) containing difenoconazole and fluoxastrobin, ACTIGARD® (Syngenta) containing acibenzolar-S-methyl, ADAMENT® (Bayer Crop Science) containing tebuconazole and trifloxystrobin, ALIETTE® (Bayer Crop Science) containing aluminum tris(O-ethyl phosphonate), ALTO® (Syngenta) containing cyproconazole, ALUMNI® (Syngenta) containing thiabendazole, AMISTAR® (Syngenta) containing azoxystrobin and difenoconazole, APROACH® (DuPont™) containing picoxystrobin and cyproconazole, APROVIA® (Syngenta) containing benzovindiflupyr (alone or together with propiconazole or difenoconazole), ARCHIVE (Syngenta) containing fluoxastrobin and azoxystrobin, CABRIO® containing pyraclostrobin, CANNONBALL® (Syngenta) containing fluoxastrobin, CARAMBA® (BASF) containing metconazole, CHAIRMAN® (Syngenta) containing fluoxastrobin and propiconazole, CHAMPION® (Nufarm) containing copper hydroxide and metallic copper equivalents, DELARO® (Bayer CropScience); ELATUS® (Syngenta) containing azoxystrobin and benzovindiflupyr; F500® (BASF) containing strobilurin, FLINT® (Bayer Crop Science) containing trifloxystrobin, FONTELIS® (Corteva) containing penthiopyrad, GRADUATE® (Syngenta) containing fluopyram and pyrimethanil (alone or together with azoxystrobin), INITUM® (BASF), INSPIRE® (Syngenta) containing difenoconazole (alone or together with cyprodinil or propiconazole), LUNA® (Bayer Crop Science) containing fluopyram and pyrimethanil, MENTOR® (Syngenta) containing propiconazole, MERTECT® (Syngenta) containing thiabendazole, MINUET® (Bayer Crop Science) containing Bacillus subtilis strain QST 713, MIRAVIS® (Syngenta) containing pydiflumetofen (alone or in combination with difenoconazole or propiconazole or fluopyram or azoxystrobin and propiconazole), OMETGA® (Syngenta) containing fluazinam, ORONDIS® (Syngenta) containing oxathiapiprolin (alone or in combination with mefenoxam or chlorothalonil or mandipropamid), PREVICUR® (Bayer Crop Science) containing propamocarb hydrochloride, PRISTINE® containing pyraclostrobin and boscalid, PROLINE® (Bayer Crop Science) containing prothioconazole, PROPULSE® (Bayer Crop Science) containing fluopyram and prothioconazole, PROSARO® (Bayer Crop Science) containing prothioconazole and tebuconazole, PROVOST® (Bayer CropQUADRIS® (Syngenta), containing azoxystrobin (alone or in combination with chlorothalonil, mefenoxam, or difenoconazole), QUILT® (Syngenta), containing azoxystrobin and propiconazole, REGALIA® (Marrone BioInnovations), containing Reynoutria sachalinensis, REVUS® (Syngenta), containing mandipropamid (alone or in combination with difenoconazole), RIDOMIL® (Syngenta), containing mefenoxam (alone or in combination with chlorothalonil, copper OH, or mancozeb), SCALA® (Bayer Crop Science), containing pyrimethanil and 1,2 - propanediol, SCHOLAR® (Syngenta), containing fluoxastrobin; SERENADE® (Bayer Crop Science), containing Bacillus subtilis strain QST713, STRATEGO® (Bayer Crop Science), containing propiconazole and trifloxystrobin, STADIUM® (Syngenta), containing azoxystrobin, fluoxastrobin, and difenoconazole; SWITCH® (Syngenta), containing cyprodinil and fluoxastrobin; TANOS® (DuPont (trademark)), containing famoxadone and cymoxanil; TILT® (Syngenta), containing propiconazole (alone or in combination with chlorothalonil); TOP® (Syngenta), containing difenoconazole; TRIVAPRO® (Syngenta), containing propiconazole, azoxystrobin, and benzovindiflupyr; UNIFORM® (Syngenta), containing azoxystrobin and mefenoxam, VANGARD® (Syngenta), containing cyprodinil, VELUM® (Bayer CropSCIENCE), CEDAXAN, MEFENOXAM, and FLUDIOXONIL with thiabendazole or azoxystrobin, VIBRANCE® (Syngenta), VYDATE® (DuPont (trademark)) with oxamyl, and XEMIUM® (BASF) with carboxamide are included, but not limited to these.

[0174] Certain non-limiting active combinations of ascaryosides and certain additional types of active agents used in various embodiments of the present disclosure are described in more detail below.

[0175] Ascaryoside + Triazole fungicide In some embodiments, the present disclosure provides compositions and methods relating to ascaryosides and triazoles (e.g., prothioconazole, tebuconazole, or a fungicide having the same mode of action as prothioconazole or tebuconazole). In some embodiments, the ascaryoside can be used with any triazole fungicide or any fungicide that inhibits the CYP51A1 enzyme. The CYP51A1 enzyme is necessary for the biosynthesis of ergosterol, an important component of the fungal cell membrane. The use of at least one ascaryoside and a fungicide promotes the activity of the fungicide and requires less amount of the fungicide.

[0176] Triazole fungicides include, but are not limited to, microbutanil, epoxiconazole, ipconazole, metconazole, uniconazole-P, uniconazole, triticonazole, tricyclazole, triazbutyl, triadimenol, triadimefon, tetraconazole, tebuconazole, simconazole, quinconazole, prothioconazole, propiconazole, penconazole, imibenconazole, hexaconazole, fluconazole, fluconazole-cis, flutriafol, flusilazole, flucinconazole, flutrimazole, fenbuconazole, etaconazole, diniconazole-M, diniconazole, difenoconazole, diclobutrazole, cyproconazole, bromoconazole, bitertanol, azaconazole, and amisulbrom. In certain embodiments, the triazole fungicide is prothioconazole or tebuconazole. Also included are fungicide mixtures that are particularly fungicides used in combination with prothioconazole, tebuconazole, or other triazoles. Such fungicides used with prothioconazole include, but are not limited to, azoxystrobin, boscalid, tebuconazole, trifloxystrobin, fluopyram, azoxystrobin, and benzovindiflupyr. Such fungicides used with tebuconazole include, but are not limited to, azoxystrobin, boscalid, prothioconazole, trifloxystrobin, fluopyram, azoxystrobin, and benzovindiflupyr.

[0177] 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 substance produced mainly for its fungicidal properties. Prothioconazole is a systemic broad-spectrum fungicide of the triazolinethione chemical class. It is a member of the class of compounds triazole and possesses a unique toxin family among the fungicides of this class. Its effective fungicidal properties may be attributed to the ability to inhibit CYP51A1. This enzyme is necessary for the biosynthesis of ergosterol, an important component of the fungal cell membrane. Prothioconazole is a fungicide manufactured for the control of diseases caused by ascomycetes, basidiomycetes, and imperfect fungi. Prothioconazole is generally applied either alone or as a tank mix with other agents such as fungicides, insecticides, herbicides, or other crop agents. Any source of prothioconazole can be used, but it 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.

[0178] Prothioconazole is typically formulated as a 4 lb / gal suspension concentrate (equivalent to a flowable concentrate; FlC) formulation (Proline® 480 SC fungicide, 41% active ingredient). This product can be applied as a foliar spray or soil application (soil application in the case of peanuts) after heading, at a rate of 0.088 - 0.178 lb ai / A / application (0.100 - 0.200 kg ai / ha / application) using ground or aerial equipment. The proposed maximum seasonal rate is in the range of 0.285 - 0.713 lb ai / A (0.320 - 0.800 kg ai / ha), and the proposed re-treatment interval is 5 - 21 days. Using at least one ascarylose and prothioconazole according to the present disclosure increases the fungicidal activity, reduces the disease severity, and makes it more efficient for control. Thus, lower concentrations or rates of prothioconazole are required.

[0179] Tebuconazole (IUPAC: 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-ylmethyl)pentan-3-ol) is a penetrant fungicide that provides both curative and preventive control of diseases. Tebuconazole is used in many different common fungicide products to control fungi, bacteria, and viruses that affect plants. Tebuconazole is a fungicide known as a DMI (demethylation-inhibiting fungicide) that affects the fungal cell wall by inhibiting spore germination and fungal growth. It also prevents the production of ergosterol, an essential molecule for fungal formation. As a result, fungal formation is slowed and ultimately stopped. Because of this unique mode of action, tebuconazole is bacteriostatic or growth-inhibiting rather than bactericidal or fungicidal. Tebuconazole is a flexible fungicide that can be used for both curative and preventive fungal control. It functions penetratively, is absorbed by the target plant to protect it from disease, prevents further spread, or can completely eliminate the disease depending on the severity level. Some of the common fungi and disease problems known to be treated by tebuconazole are rust, southern blight, leaf spot, and anthracnose. Tebuconazole is also used on turf and ornamental plants to control a variety of fungal diseases including, but not limited to, leaf blight, gray leaf spot, and powdery mildew.

[0180] Tebuconazole can be applied at a rate of 4 - 10 fl.oz. per acre. The spray volume can range from about 5 - 300 gallons of finished spray per acre depending on the equipment at the time of application, the plant species, and the growth stage of the plant. However, if too much of the triazole active ingredient is absorbed by the plant, it can cause phytotoxicity and poison the plant. Some plants are sensitive to the triazole active ingredient. Therefore, the use of tebuconazole with the ascaloside provided according to the present disclosure can reduce or prevent phytotoxicity because less tebuconazole is required to achieve equivalent results.

[0181] In certain embodiments, the present disclosure provides a mixture of a triazole fungicide and an ascaloside, wherein the weight ratio of the triazole fungicide to the ascaloside exceeds 1000:1. In certain embodiments, the present disclosure provides a mixture of a triazole fungicide and an ascaloside, wherein the weight ratio of the triazole fungicide to the ascaloside 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.

[0182] In certain embodiments, the present disclosure provides a mixture of a triazole fungicide and an ascaloside, wherein the mixed product is labeled for application to a crop at a rate lower than the labeled rate of the triazole fungicide alone. In certain embodiments, the mixture is characterized in that the lowest labeled application rate delivers less than 4 oz, less than 3 oz, less than 2.5 oz, less than 2 oz, or less than 1 oz of triazole fungicide per acre. In certain embodiments, such mixtures are effective in reducing fungal diseases of the crops to which they are applied, as compared to triazole fungicides applied alone at full labeled rates (e.g., 4 - 10 oz per acre).

[0183] In certain embodiments, the present disclosure provides a mixture of tebuconazole and an ascaloside, wherein the weight ratio of tebuconazole to the ascaloside exceeds 1000:1. In certain embodiments, the present disclosure provides a mixture of tebuconazole and an ascaloside, wherein the weight ratio of tebuconazole to the ascaloside 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.

[0184] In certain embodiments, the present disclosure provides a mixture of tebuconazole and ascarylose, wherein the mixed product is labeled for application to crops at a rate lower than the label rate of tebuconazole alone. In certain embodiments, the mixture is characterized in that the lowest label application rate delivers less than 4 oz of tebuconazole per acre, less than 3 oz, less than 2.5 oz, less than 2 oz, or less than 1 oz of tebuconazole. In certain embodiments, such mixtures are effective in reducing fungal diseases of the crops to which they are applied, compared to tebuconazole applied alone at full label rate (e.g., 4 - 10 oz per acre).

[0185] In certain embodiments, the present disclosure provides a mixture of prothioconazole and ascarylose, wherein the weight ratio of prothioconazole to ascarylose exceeds 1000:1. In certain embodiments, the present disclosure provides a mixture of prothioconazole and ascarylose, wherein the weight ratio of prothioconazole to ascarylose 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.

[0186] In certain embodiments, the present disclosure provides a mixture of prothioconazole and ascarylose, wherein the mixed product is labeled for application to crops at a rate lower than the label rate of prothioconazole alone. In certain embodiments, the mixture is characterized in that the lowest label application rate delivers less than 4 oz of prothioconazole per acre, less than 3 oz, less than 2.5 oz, less than 2 oz, or less than 1 oz of prothioconazole. In certain embodiments, such mixtures are more effective in reducing fungal diseases of the crops to which they are applied, compared to applying prothioconazole alone at full label rate (e.g., 4 - 10 oz per acre).

[0187] In certain embodiments, the present disclosure provides a mixture of propiconazole and ascarylose having a weight ratio of propiconazole to ascarylose that exceeds 1000:1. In certain embodiments, the present disclosure provides a mixture of propiconazole and ascarylose, wherein the weight ratio of propiconazole to ascarylose 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.

[0188] In certain embodiments, the present disclosure provides a mixture of propiconazole and ascarylose, characterized in that the mixed product is labeled for application to crops at a rate lower than the labeled rate of propiconazole alone. In certain embodiments, the mixture is characterized in that the lowest labeled application rate delivers less than 4 oz of propiconazole per acre, less than 3 oz, less than 2.5 oz, less than 2 oz, or less than 1 oz of propiconazole per acre. In certain embodiments, such mixtures are effective in reducing fungal diseases of the crops to which they are applied compared to propiconazole applied alone at the full labeled rate (e.g., 4 - 10 oz per acre).

[0189] Ascarylose + strobilurin fungicide In some embodiments, the present disclosure provides compositions and methods relating to ascarylose and strobilurins (e.g., azoxystrobin, kresoxim - methyl, picoxystrobin, pyraclostrobin, trifloxystrobin, famoxadone, or fenamidone). In some embodiments, ascarylose is combined with any strobilurin fungicide or any fungicide that inhibits mitochondrial respiration, more specifically, a cytochrome complex (e.g., a quinone outside inhibitor or Q oIt can be used together with any fungicide that binds to the quinol binding site of (I). In certain embodiments, the ascarylside can be used together with any strobilurin fungicide (e.g., a member of the class of natural products collectively known as strobilurins, or any material called a strobilurin fungicide that includes synthetic analogs, derivatives or mimics of strobilurin natural products, or a synthetic molecule having a structure or mode of action similar to strobilurin that includes fenamidone and famoxadone). The use of at least one ascarylside and a fungicide promotes the activity of the fungicide and less of the fungicide is required. The fungicide, when used with the ascarylside, can result in better plant growth and yield and better control or prevention of plant diseases. Additionally, the activity of the ascarylside may be promoted by applying it together with the fungicide so that less of the ascarylside may be required.

[0190] According to the present disclosure, the ascarylside can be used in combination with a Q o I fungicide, particularly a strobilurin. The Q o I fungicides include, but are not limited to, strobylurin, azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, fenamistrobin, dimoxystrobin, fluoxastrobin, metominostrobin, mandestrobin, pyra-metostrobin, pyrazooxystrobin, kresoxim-methyl, fenamidone, and famoxadone.

[0191] As described above, fungicides having the same mode of action as strobilurin or strobilurin can be used in the practice of the present invention. In particular, mixtures of fungicides used in combination with strobilurin are also included. Such fungicides used with strobilurin include, but are not limited to, boscalid, tebuconazole, propiconazole, microbutanil, epoxiconazole, ipconazole, metconazole, uniconazole-P, uniconazole, triticonazole, tricyclazole, triazbutyl, triadimenol, triadimefon, tetraconazole, tebuconazole, simconazole, quinconazole, prothioconazole, propiconazole, penconazole, imibenconazole, hexaconazole, fluconazole, fluconazole-cis, flutriafol, flusilazole, fluquinconazole, flutrimazole, fenbuconazole, etaconazole, diniconazole-M, diniconazole, difenoconazole, diclobutrazole, cyproconazole, bromoconazole, bitertanol, azaconazole, amisulbrom, fluopyram, benzovindiflupyr, and the like.

[0192] Azoxystrobin (IUPAC: methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-methoxyprop-2-enoate) is a synthetic chemical substance mainly manufactured for its fungicidal properties. Azoxystrobin is a xylem-mobile systemic penetrant fungicide with translaminar, protectant, and curative properties. It is a member of the strobilurin class of compounds. Azoxystrobin is effective against members of the Ascomycota, Deuteromycota, and Basidiomycota, as well as a number of fungal plant pathogens including the Oomycota. Additionally, its properties mean that it can move systemically within 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, net blotch, blight, etc. World-wide, azoxystrobin is registered for use on all important crops. For example, in the European Union and the United States, it is registered for use on wheat, barley, oats, rye, soybeans, cotton, rice, strawberries, peas, beans, onions, and many other vegetables. Azoxystrobin can be applied alone or as a tank mix with other agents such as fungicides, insecticides, herbicides, or other crop agents. Any source of azoxystrobin can be used, but it is sold under various trade names such as Amistar, Abound, Heritage, Olympus, Ortiva, Priori Xtra, Scotts DiseaseEx, Haedes, Quadris, etc. Suppliers and additional brand names used in the United States are listed in The National Pesticide Information Retrieval System.

[0193] 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 proposed maximum seasonal rate is in the range of 1.5 lb ai / A and the proposed re-treatment interval is 14 - 21 days. Using at least one ascarylside of the present invention and azoxystrobin increases the activity of the fungicide, reduces the severity of the disease, and makes it more efficient for its control. Therefore, a lower concentration or lower ratio of azoxystrobin is required.

[0194] Picoxystrobin (IUPAC: (E)-methyl 3-methoxy-2-(2-(((6-(trifluoromethyl)pyridin-2-yl)oxy)methyl)phenyl)acrylate) is a penetrant fungicide that provides both curative and preventive control of diseased plants. Picoxystrobin is a synthetic chemical mainly manufactured for its fungicidal properties. Picoxystrobin is a Quinone-outside inhibitor penetrant fungicide with translaminar, protectant, and curative properties. It is a member of the strobilurin class of compounds. Picoxystrobin is effective against a number of fungal plant pathogens including members of the Ascomycota, Deuteromycota, and Basidiomycota, as well as the Oomycota. Additionally, its properties mean that it can move penetratively within plant tissue to protect parts of the crop not in contact with the spray. Important diseases it controls include leaf spot, rust, powdery mildew, downy mildew, net blotch, blight, etc. Picoxystrobin is currently registered in many countries such as Argentina, Austria, Belgium, Brazil, Canada, Colombia, the Czech Republic, Denmark, Estonia, Finland, France, Germany, Hungary, Ireland, Kenya, Latvia, Lithuania, the Netherlands, New Zealand, Norway, Poland, Romania, Slovakia, South Africa, Sweden, the United States, and the United Kingdom.

[0195] Picoxystrobin is sold as a single-component fungicide and also in several mixtures with other fungicides including cyproconazole (Furlong, Stinger, and Aproach Prima), chlorothalonil (Credo and Plinker), and cyprodinil (Acanto Prima). Picoxystrobin can be applied alone or as a tank mix with other agents such as fungicides, insecticides, herbicides, or other crop agents. Any source of picoxystrobin can be used, and it is sold under various trade names such as Aproach, Acapela, Cerefit, Prima, etc. Suppliers and additional brand names used in the United States are listed in The National Pesticide Information Retrieval System.

[0196] Picoxystrobin is typically supplied as a solution concentrate (SC) formulated for application at a rate of 0.05 - 0.2 lb AI per acre. The spray volume can range from about 5 to 300 gallons of finished spray per acre, depending on the equipment at the time of application, the plant species, and the growth stage of the plant. As outlined below, using picoxystrobin with at least one ascarylose of the present invention in various ways increases the fungicidal activity, reduces the disease severity, and makes it more efficient for its control. Thus, a lower concentration or rate of azoxystrobin is required.

[0197] In certain embodiments, the present disclosure provides a mixture of a strobilurin fungicide and an ascarylose, wherein the weight ratio of the strobilurin fungicide to the ascarylose exceeds 1000:1. In certain embodiments, the present disclosure provides a mixture of a strobilurin fungicide and an ascarylose, wherein the weight ratio of the strobilurin fungicide to the ascarylose 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.

[0198] In certain embodiments, the present disclosure provides a mixture of a strobilurin fungicide and an ascarylose, wherein the mixed product is labeled for application to a crop at a rate lower than the labeled rate of the strobilurin fungicide alone. In certain embodiments, the mixture is characterized in that the lowest labeled application rate delivers less than 4 oz of strobilurin fungicide per acre, less than 3 oz, less than 2.5 oz, less than 2 oz, or less than 1 oz of strobilurin fungicide per acre. In certain embodiments, such mixtures are effective in reducing fungal diseases of the crops to which they are applied compared to strobilurin fungicides applied alone at full labeled rates (e.g., 4 - 10 oz per acre).

[0199] In certain embodiments, the present disclosure provides a mixture of azoxystrobin and an ascarylose, wherein the weight ratio of azoxystrobin to ascarylose exceeds 1000:1. In certain embodiments, the present disclosure provides a mixture of azoxystrobin and an ascarylose, wherein the weight ratio of azoxystrobin to ascarylose 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.

[0200] In certain embodiments, the present disclosure provides a mixture of azoxystrobin and an ascarylose, wherein the mixed product is labeled for application to a crop at a rate lower than the labeled rate of azoxystrobin alone. In certain embodiments, the mixture is characterized in that the lowest labeled application rate delivers less than 4 oz of azoxystrobin per acre, less than 3 oz per acre, less than 2.5 oz per acre, less than 2 oz per acre, or less than 1 oz of azoxystrobin per acre. In certain embodiments, such mixtures are effective in reducing fungal diseases of the crops to which they are applied compared to azoxystrobin applied alone at full labeled rates (e.g., 4 - 10 oz per acre).

[0201] Ascarylose + SDHI fungicide In some embodiments, the present disclosure provides compositions and methods related to ascarosides and succinate dehydrogenase inhibitor (SDHI) fungicides. Succinate dehydrogenase (SDH) complex II is thought to be an essential component of the mitochondrial respiratory chain in fungi. The SDH enzyme directly transfers electrons from succinate to the ubiquinone pool of the respiratory chain, facilitating energy transfer within the mitochondria. Succinate dehydrogenase inhibitors (SDHIs) are a class of fungicides that act on the mitochondrial SDH complex II, blocking cellular energy transfer and thereby inhibiting fungal development. Many SDHIs inhibit fungal respiration by blocking the ubiquinone binding (Qp) site. SDHIs that bind strongly to the Qp site physically block access to the ubiquinone substrate, preventing further cycles of succinate oxidation as a result.

[0202] Examples of 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, fluxapyroxad, flutolanil, mebenil, mepronil, salicylanilide, fluopyram, benzohydroxamic acid, flutemetobenz, fluopicolide, fluopyrimid, thioxymid, triclopyricarb, zarilamid, and zoxamide. SDHI fungicides also include carboxamide fungicides that inhibit succinate dehydrogenase (SDH) complex II. Examples of carboxamide fungicides that inhibit SDH include, but are not limited to, oxathiine fungicides, furancarboxamide fungicides, pyrazinecarboxamide fungicides, pyrazolecarboxamide fungicides, and pyridinecarboxamide fungicides. Examples of oxathiine fungicides include, but are not limited to, carboxin and oxycarboxin. Examples of furancarboxamide fungicides include, but are not limited to, fenfuram, flucarbanyl, or metflumoxam. An example of a pyrazinecarboxamide fungicide is pyraziflumid. Examples of pyrazolecarboxamide fungicides include, but are not limited to, benzovindiflupyr, bixafen, flubeneteram, fluindapyr, fluxapyroxad, flametopyr, impeflupoxam, isoflucypram, isopyrazam, penthiopyrad, pydiflumetofen, pyrapropion, sedaxane, ethaboxam, and difenoconazole. Examples of pyridinecarboxamide fungicides include, but are not limited to, boscalid or cyclobutrifluram. Examples of SDHI fungicides also include thiopheneamide fungicides that inhibit SDH complex II, such as isofetamid.

[0203] In certain embodiments, the present disclosure provides a mixture of an SDHI fungicide and an ascarylose, wherein the weight ratio of the SDHI fungicide to the ascarylose exceeds 1000:1. In certain embodiments, the present disclosure provides a mixture of an SDHI fungicide and an ascarylose, wherein the weight ratio of the SDHI fungicide to the ascarylose 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.

[0204] In certain embodiments, the present disclosure provides a mixture of tebuconazole and ascarylose, wherein the mixture product is labeled for application to a crop at a rate lower than the labeled rate of the SDHI fungicide alone. In certain embodiments, the mixture is characterized in that the minimum labeled application rate delivers less than 4 oz, less than 3 oz, less than 2.5 oz, less than 2 oz, or less than 1 oz of the SDHI fungicide per acre. In certain embodiments, such mixtures are effective in reducing fungal diseases of the crops to which they are applied, as compared to the SDHI fungicides applied alone at full labeled rates (e.g., 4 - 10 oz per acre).

[0205] Multi-way mixture In certain embodiments, the present disclosure provides mixtures and / or products intended for co-application to a crop containing one or more ascaryloses and at least two additional active agents. In certain embodiments, such products include a mixture of an ascarylose(s) 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., triazole and strobilurin as in Examples 2 and 8 below, or triazole and SDHI as in Example 6).

[0206] In certain embodiments, the present disclosure provides mixtures and / or products intended for simultaneous application to crops containing one or more ascalosides and two or more different triazole fungicides (e.g., triazole fungicides fully described above, etc.). In certain embodiments, the present disclosure provides mixtures and / or products intended for simultaneous application to crops containing one or more ascalosides and two or more different strobilurin fungicides (e.g., strobilurin fungicides fully described above, etc.). In certain embodiments, the present disclosure provides mixtures and / or products intended for simultaneous application to crops containing one or more ascalosides and two or more different SDHI fungicides (e.g., SDHI fungicides more fully described above, etc.). In certain embodiments, the present disclosure provides mixtures and / or products intended for simultaneous application to crops containing one or more ascalosides, at least one triazole fungicide, and at least one strobilurin fungicide. In certain embodiments, the present disclosure provides mixtures and / or products intended for simultaneous application to crops containing one or more ascalosides, at least one triazole fungicide, and at least one SDHI fungicide. In certain embodiments, the present disclosure provides mixtures and / or products intended for simultaneous application to crops containing one or more ascalosides, at least one strobilurin fungicide, and at least one SDHI fungicide.

[0207] In certain embodiments, the present disclosure provides mixtures and / or products intended for simultaneous application to a crop containing one or more ascalonsides, wherein at least two different chemical fungicides are characterized by a weight ratio of chemical fungicide to ascalonside exceeding 1000:1. In certain embodiments, the present disclosure provides mixtures and / or products intended for simultaneous application to a crop containing one or more ascalonsides and at least two different chemical fungicides, wherein the weight ratio of chemical fungicide to ascalonside 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.

[0208] In certain embodiments, the present disclosure provides mixtures and / or products intended for simultaneous application to a crop containing one or more ascalonsides, wherein at least two different chemical fungicides are characterized in that the combined product is labeled for application to the crop at a rate lower than the labeled rate of the chemical fungicide formulated without ascalonside(s).

[0209] Use(s) and composition(s) As described above, the disclosed treatments using ascaloside and additional active agents (e.g., including, but not limited to, triazoles, strobilurins, or SDHI fungicides as described in detail above) can be used to significantly reduce disease, promote plant growth and / or yield, and reduce dependence on conventional pesticides. The term "treating" or "treatment" or derivatives thereof includes substantially inhibiting, delaying, or reversing the progression of a condition, substantially improving the symptoms of a condition, or substantially preventing the appearance of a symptom or condition caused by one or more pathogens (e.g., fungal pathogens). The terms "controlling" and "protecting a plant from a pathogen" refer to inhibiting or reducing the growth, germination, reproduction, and / or proliferation of the pathogen of interest, and / or killing, removing, destroying, or otherwise reducing the occurrence and / or activity of the pathogen of interest. Thus, plants treated according to the present disclosure can exhibit a statistically significant reduction in disease severity or disease incidence in the presence of plant pathogens. The term "preventing" and variations thereof mean controlling a disease state prior to the growth or infestation of fungi or bacteria. In this case, the composition is applied before exposure to the pathogen. The term "inhibiting" and all variations of this term are intended to encompass limiting or prohibiting the growth of fungi or pests.

[0210] In some embodiments, treatment with ascaloside and an additional active agent provides an additive effect and / or more than an additive effect and / or a synergistic effect. As will be appreciated by those skilled in the art, a synergistic effect occurs when the combined effect of two or more active agents is greater than the sum of the effects that the active agents would have individually. Thus, in the context of the present disclosure, a synergistic effect is demonstrated when the combined effect of ascaloside and an additional active agent exhibits an effect greater than the individual effect of ascaloside + the individual effect of the additional active agent (e.g., with respect to greater anti-parasitic activity, broader anti-parasitic activity, increased yield, etc.). Treatment with ascaloside and an additional agent can, in some embodiments, result in better than expected results compared to treatment with only the individual active agents (e.g., ascaloside and the additional active agent) alone. Thus, a plant or plant part treated with an effective amount of the components described herein can exhibit a statistically significant reduction in disease severity or reduction in disease incidence in the presence of a pathogen. The reduction in disease severity or reduction in disease incidence can be a reduction of about 30% to about 40%, about 50%, about 60%, about 70%, about 80%, about 90%, or about 100% compared to an untreated control plant. In other instances, a plant treated with an active agent (e.g., a fungicide) provided herein can exhibit 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% reduction in disease severity or reduction in disease incidence compared to an untreated control plant in the presence of a plant pathogen.

[0211] In some embodiments, treatment with ascaloside and an additional active agent as provided herein provides a broader anti-parasitic activity (e.g., controlling several diseases that occur simultaneously in a given crop).

[0212] In some embodiments, treatment with an ascaloside and an additional active agent as provided herein can reduce the amount of additional active agent required to achieve results comparable to those seen without the ascaloside. For example, to achieve beneficial results and control a pathogen (e.g., a fungal pathogen), less additional active ingredient (e.g., a fungicide or fungicide mixture) or less ascaloside may be required, or less application during the growth period may be required. In some embodiments, the amount of active agent (e.g., a fungicide) required for the prevention or treatment of a plant disease may 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, the application rate of the active agent (e.g., a fungicide) for the above-mentioned pathogen 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. Similarly, the amount of the ascaloside composition may also be reduced. The ascaloside(s) may be reduced by about 5%, about 10%, about 20%, about 30%, about 40%, about 50%, about 60%, about 70%, about 90% or more.

[0213] In some embodiments, treatment with the ascalosides and additional active agents provided herein can provide additional benefits, such as an increase in plant health, growth, and / or yield. The increase in yield can include any statistically significant increase, including but not limited to, an increase of at least 1%, at least 3%, at least 5%, at least 10%, at least 20%, at least 30%, at least 50%, at least 70%, at least 100% or more in yield compared to plants not exposed to these two components.

[0214] One or more ascalosides and one or more additional active agents (e.g., including but not limited to triazoles, strobilurins, and SDHIs as described in detail above) are generally applied in effective amounts. An effective amount is an amount sufficient to control, treat, prevent, or inhibit plant pathogens and / or to reduce the severity of plant diseases or the incidence of plant diseases. By controlling plant diseases, the effective amount improves the desired agronomic traits and promotes and increases the health, growth, and yield of plants. One or more ascalosides and one or more active agents can be applied to plants in various ways. In some embodiments, one or more ascalosides and one or more additional active agents are applied simultaneously either within separate formulations / agricultural compositions (e.g., such that both one or more ascalosides and one or more additional active agents are applied to each other within a given period of time), or within the same formulation / agricultural composition.

[0215] In some embodiments, simultaneous application can include applying two separate formulations (one containing one or more ascalosides and one containing one or more additional active agents) at a close point in time, e.g., substantially simultaneously or within about 1 minute, about 5 minutes, about 10 minutes, about 30 minutes, about 1 hour, about 4 hours, about 6 hours, about 12 hours, about 24 hours, or about 2 days of each other. When applying one or more ascalosides and additional active agents separately, the one or more ascalosides can be applied before or after the application of the additional active agent.

[0216] In some embodiments, simultaneous application can include combining one or more ascalosides and one or more additional active agents immediately prior to application to the plant (e.g., immediately prior to application). One suitable method for administering one or more ascalosides and one or more additional active agents is to mix the components on-site, e.g., one or more ascalosides can be added to a fully formulated tank mixture containing one or more additional active agents.

[0217] In other embodiments, the components to be applied simultaneously can be combined at a point in time even further prior to application. In such embodiments, an agricultural formulation is prepared, the formulation comprising a combination of one or more ascalosides and one or more additional active agents with one or more inert components. Advantageously, in some embodiments, combinations of one or more ascalosides and one or more additional active agents are provided herein, which are compatible with each other and the resulting formulation can exhibit stability over a long period of time (e.g., for one week or more, one month or more, two months or more, three months or more, four months or more, five months or more, or six months or more) under standard conditions (e.g., at room temperature, housed in a closed system with one or more relative humidity zones). Demonstration of stability in this context can vary. For example, in some embodiments, no significant separation is observed visually. In some embodiments, no significant change in the amount of the active ingredient and / or ascaloside is observed via conventional methods (e.g., spectroscopy). In some embodiments, no significant chemical degradation of the active ingredient and / or ascaloside is observed using conventional methods (e.g., spectroscopy).

[0218] Such formulations containing both one or more ascalosides and one or more additional active agents may vary in composition and form. In some embodiments, such formulations are in solid form, and in some embodiments, such formulations are in liquid form. As referenced, in addition to one or more ascalosides and one or more additional active agents, one or more inert components, such as one or more agriculturally acceptable carriers (also referred to as agriculturally acceptable or suitable adjuvants), are generally included within the formulation. In the formulations and methods of the present disclosure, it is preferred to use non-toxic carriers. The term "agriculturally acceptable carrier" refers to any carrier suitable for administration to plants or soil, such as solutions (e.g., directly sprayable or dilutable solutions), emulsions (e.g., emulsion concentrates and diluted emulsions), wettable powders, suspensions, soluble powders, powders, dusts, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, encapsulation in polymeric materials, coatable pastes, natural and synthetic materials impregnated with active compounds, and those used to form microencapsulation in polymeric substances, etc., including conventional excipients in formulation technology. In some embodiments, the agriculturally acceptable carrier can include surfactants, emulsifiers, oils, salts, and the like.

[0219] These compositions can be prepared in a known manner by mixing, for example, one or more ascalosides and one or more additional active agents with one or more agriculturally acceptable carriers such as liquid solvents or solid carriers, optionally including surfactants, dispersants, foam formers, colorants, processing aids, lubricants, fillers, strengthening agents, flame retardants, light stabilizers, UV absorbers, weather stabilizers, plasticizers, release agents, fragrances, heat retention additives (e.g., silica), cross-linking agents, antioxidants, defoamers, buffers, pH adjusters, compatibilizers, drift control additives, bulking agents / stickers, tackifiers, plant penetrants, toxicity moderators, spreaders, wetting agents, etc., although not limited thereto. In some embodiments, such formulations may contain one or more additional active agents and / or one or more plant or plant product treatment compounds. Further, some compositions remain in that they are not easily washed off the leaves of plants during rain and can thus protect against pests during and after rainy days. The additional components described herein can be added directly to the formulation as described above or, alternatively, can be added separately, for example, at the time of application. In some embodiments, wetting agents, emulsifiers, spreaders, etc. are used in the formulation. The formulation includes concentrated forms in which the active agent is present at a concentration of 0.001 - 98.0% and the remaining contents are agriculturally acceptable carriers / adjuvants.

[0220] Such formulations, especially those having less than 50% of the present compound, 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 the compounds described herein at a lower concentration of 0.001 - 0.1%.

[0221] The formulation further contains an "adjuvant surfactant" which can promote the deposition, wetting, and penetration of the compound onto the target crop and organisms. These "adjuvant surfactants" may be used, if desired, as components of the formulation or as a tank mixture. The amount of the adjuvant surfactant typically varies from 0.01 to 1.0% by volume, preferably from 0.05 to 0.5% by volume, based on the spray volume of water. Suitable adjuvant surfactants include ethoxylated nonylphenol, ethoxylated synthetic or natural alcohols, salts of esters or sulfosuccinic acid, ethoxylated organosilicones, ethoxylated fatty amines, mixtures of surfactants and mineral or vegetable oils, crop oil concentrates (mineral oil (85%) + emulsifier (15%)), nonylphenol ethoxylate, benzylcocoalkyldimethyl quaternary ammonium salts; mixtures of petroleum hydrocarbons, alkyl esters, organic acids, and anionic surfactants, C9-Cu alkyl polyglycosides, alcohol ethoxylate phosphates, 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, tridecyl alcohol (synthetic) ethoxylate (8EO), tallow amine ethoxylate (15EO), PEG(400)-dioleate-99, but are not limited thereto. The formulation may also include an oil-in-water emulsion. When the agriculturally acceptable carrier is water, in some embodiments, the organic solvent may be incorporated as an auxiliary liquid solvent. Suitable liquid solvents include, for example, aromatic compounds (e.g., xylene, toluene, and alkylnaphthalenes), chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons (e.g., chlorobenzene, chloroethylene, and methylene chloride), aliphatic hydrocarbons (e.g., cyclohexane), paraffins (e.g., petroleum fractions, mineral, and vegetable oils), alcohols (e.g., butanol or glycols and their ethers and esters), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone), and strongly polar solvents (e.g., dimethylformamide and dimethyl sulfoxide).Other examples of organic solvents include xylene, propylbenzene fraction, or mixed naphthalene fraction, mineral oil, substituted aromatic organic liquids such as dioctyl phthalate; kerosene, dialkylamides of various fatty acids, especially dimethylamide 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 fraction or mineral oil, aromatic solvents, hydrocarbons such as paraffin oil, terpene solvents, rosin derivatives, aliphatic ketones such as cyclohexanone, compound aliphatic and aromatic alcohols such as 2-ethoxyethanol, soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, esters of the above vegetable oils, etc., but are not limited thereto. A mixture of two or more organic liquids may be used in the preparation of certain emulsifiable concentrates. Examples of organic liquids include xylene and propylbenzene fraction, and in some cases, xylene is most preferred. The surface-active dispersant is typically used in an amount of 0.1 to 20% by weight based on the combined weight of the dispersant with one or more compounds in the liquid formulation.

[0222] Suitable solid agriculturally acceptable carriers include, for example, ammonium salts and ground natural minerals (such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth); ground synthetic minerals (such as highly dispersed silica, alumina and silicates); ground and fractionated natural rock meal (such as calcite, marble, pumice, sepiolite and dolomite), inorganic and organometallic synthetic granules, organometallic granules (such as sawdust, coconut husk, corn cob and tobacco stem). In some embodiments, the dry composition can include powders and the like.

[0223] Suitable emulsifiers and foam formers include, for example, nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates and aryl sulfonates), protein hydrolysates. Suitable dispersants include, for example, lignin-sulfite waste liquor and methylcellulose. Carboxymethylcellulose in the form of powders, granules or grids, as well as natural and synthetic polymers, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and tackifiers such as natural phospholipids, e.g., cephalin and lecithin, and synthetic phospholipids, can be used in the disclosed compositions. Examples of nonionic emulsifiers useful in the preparation of emulsifying concentrates include polyalkylene glycol ethers, and condensation products of alkylphenols and arylphenols, 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 aliphatic amine salts. Anionic emulsifiers include oil-soluble salts of alkylaryl sulfonic acids (e.g., calcium), or oil-soluble salts of sulfated polyglycol ethers and appropriate salts of phosphorylated polyglycol ethers. Other additives can include, for example, mineral oils and vegetable oils.

[0224] "Surfactants" (which can typically account for about 0.5% to about 10% of the wettable powder, for example) include nonionic surfactants such as sulfonated lignin, condensed naphthalene sulfonates, naphthalene sulfonates, alkylbenzene sulfonates, alkyl sulfonates, or ethylene oxide adducts of alkylphenols or mixtures thereof.

[0225] Inorganic pigments, such as colorants like iron oxide, titanium oxide, Prussian blue, organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes, and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc can also be included in the composition.

[0226] Methods for preparing solid and liquid compositions for pesticide use are generally known and can be used in accordance with the present disclosure (such methods include incorporating one or more ascarosides and one or more additional active agents into such compositions). In some embodiments, the composition may be utilized as a liquid concentrate, ready-to-use (RTU) liquid spray, dust, or solid, depending on the needs of the user. The compositions according to the present disclosure can, in some embodiments, be in the form of granular materials (including dust, pellets, soluble powders, free-flowing powders, water-dispersible granules, etc.). In some embodiments, the compositions according to the present disclosure can be in liquid form (e.g., a solution, suspension, or emulsion). In some embodiments, the composition is in the form of granular material treated with a liquid containing one or more ascarosides and one or more additional active agents. In some embodiments, a composition containing one or more ascarosides and one or more additional active agents is formed into a fiber or filament, and in some such embodiments, a woven or non-woven fabric (e.g., a film) can be manufactured therefrom. In some embodiments, the compositions provided herein are pelletized. In some embodiments, the compositions provided herein are in the form of a film, e.g., a plastic mulch. Any of the solid compositions provided herein can be optionally coated via methods generally known in the art to delay the release of one or more ascarosides and one or more additional active agents. The formulation selected depends on the use of the product.

[0227] The dust containing the compounds of the present disclosure can be prepared by intimately mixing one or more of the compounds in powder form with a suitable dusty agricultural carrier such as kaolin clay, ground volcanic rock, etc. The dust may suitably contain from about 1% to about 10% by weight of the compound, based on the total weight of the dust.

[0228] The wettable powder can be aggregated or compressed to form water-dispersible granules. These granules can include a mixture of the compound, an inert carrier suitable for granule application, and a surfactant. The concentration of the compound is typically from about 0.1% to about 90% by weight. "Inert carriers suitable for granule use" are typically pyrophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, purified silicate, etc. In such an operation, the finely divided carrier and surfactant are typically mixed with and ground with the compound(s).

[0229] An "aqueous suspension" can be prepared when the compound is typically dispersed in an aqueous vehicle at a concentration in the range of about 5% to about 50% by weight. The suspension can be prepared by finely grinding the compound and vigorously mixing it with a vehicle of water, surfactant, and dispersant. Inert components such as inorganic salts and synthetic or natural rubbers can also be used, if desired, to increase the density and / or viscosity of the aqueous vehicle.

[0230] The amounts of one or more ascarosides and one or more active agents contained within such formulations can vary. In certain specific embodiments, the amounts of one or more ascarosides and one or more active agents are synergistically effective amounts. Typically, the formulation contains one or more ascarosides at a lower weight percentage than one or more active agents.

[0231] In certain embodiments, the provided combination is characterized in that the synergistic amount of one or more ascalosides represents a very low percentage of the formulation. In certain embodiments, the provided combination is characterized in that the ascaloside is present in an amount of less than 1% by weight compared to other active ingredient(s). In certain embodiments, the provided combination is characterized in that the ascaloside is present in an amount of less than 0.1% by weight compared to other active ingredient(s). In certain embodiments, the provided combination is characterized in that the ascaloside is present in an amount of less than 0.05% by weight compared to other active ingredient(s). In certain embodiments, the provided combination is characterized in that the ascaloside is present in an amount of less than 0.01% by weight compared to other active ingredient(s). In certain embodiments, the provided combination is characterized in that the ascaloside is present in an amount of less than 0.001% by weight compared to other active ingredient(s).

[0232] In certain embodiments, the co - administration of one or more of the ascalonicides and one or more additional active agents described herein can be used to treat living plants or plant parts, the soil surrounding the plants, the soil in which seeds / seedlings are planted, or harvested plants or plant parts. As used herein, co - administration includes co - administration or sequential administration and can refer to administration in the same composition or separate compositions, etc. In some embodiments, the one or more ascalonicides and one or more additional active agents are applied to one or more of the plant parts, i.e., a part of the plant, such as one or more of the roots, stems, leaves, seeds, and / or flowers. Such methods can be carried out at any one or more stages of the plant life cycle, for example, on seeds, seedlings, growing plants just prior to harvest. In certain embodiments, co - administration includes spraying one or more ascalonicides and one or more additional active agents onto the leaves of the plant. In certain embodiments, co - administration includes applying a powder or solid to the leaves of the plant. In certain embodiments, co - administration includes treating the seeds of the plant with one or more ascalonicides and one or more additional active agents (e.g., prior to planting). In certain embodiments, co - administration includes treating the trunk, branches or stems of the plant with one or more ascalonicides and one or more additional active agents. In certain embodiments, co - administration includes applying one or more ascalonicides and one or more additional active agents to the soil in which the plant is growing or the soil in which the plant will grow.

[0233] The disclosed treatment methods can, in some embodiments, protect growing plants by the method described in U.S. Patent No. 10,136,595, which is hereby incorporated by reference in its entirety. For example, such methods can promote pathogen resistance and / or induce one or more plant defense responses in plants to which one or more ascalosides and one or more additional active agents are applied (or in the vicinity thereof), thereby inhibiting pathogen growth and / or parasitism. Pathogens against which the methods of the present disclosure can promote resistance include, but are not limited to, oomycetes, bacteria, nematodes, viruses, and insects, such as Pseudomonas syringae, Phytophthora infestans, Blumeria graminis, Heterodera schachtii, Meloidogyne incognita, Meloidogyne hapla, and turnip crinkle virus.

[0234] The disclosed treatment methods can further provide enhanced control of a range of plant pathogens, such as fungal pathogens. Such enhanced control may, in some embodiments, depend on the selection of one or more additional active agents. For example, by combining a given active agent with one or more ascalosides, the known activity of the active agent against a particular pathogen in a particular crop can be enhanced.

[0235] As one non-limiting example, the combination of ascalosides and triazole fungicides has shown enhanced efficacy against fungal pathogens such as Fusarium species. Figure 1 shows data from a field trial in which wheat was sprayed with Proline™ alone (a commercial formulation of the triazole fungicide prothioconazole), PHYTALIX® alone (a product based on ascaloside active ingredient(s)), and a combination of PROLINE™ and PHYTALIX®. The combination product showed evidence of a synergistic effect where both the level of disease control and wheat yield increased with the mixture in amounts greater than the simple additive effect of the two products.

[0236] The exact method of treating a plant or soil with one or more ascarosides and one or more active agents is not particularly limited. Treatment of plants and / or soil according to the present disclosure can be carried out, for example, by dipping, spraying, evaporation, atomization, spreading, coating, side application, or in-furrow application. For example, in certain embodiments, a plant or soil can be sprayed with one or more suitable liquid compositions, a solid plastic multi-composition can be applied to the soil around a plant, and / or a granular composition can be provided for in-furrow application or side application. In some embodiments, the methods provided herein include treating seeds prior to planting.

[0237] The types of plants that can be treated according to the methods of the present disclosure are not particularly limited and can be, for example, fruit and vegetable plants, trees, and shrubs. Non-limiting examples of plants that can be treated according to the disclosed methods include plants selected from the group consisting of tobacco, Arabidopsis, tomato, barley, potato, sweet potato, yam, cotton, soybean, strawberry, sugarcane, sugar beet, corn, rice, wheat, rye, oats, sorghum, millet, bean, pea, apple, banana, European 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 hemp, but are not limited thereto.

[0238] In some embodiments, the compositions and methods provided herein can be used to protect any plant from fungal or bacterial diseases and to promote the health, growth, and yield of plants, including but not limited to monocots and dicots.Examples of plant species of interest include Zea mays, Brassica species (e.g., B. napus, B. rapa, B. juncea), particularly Brassica species useful as sources of seed oil, Medicago sativa, Oryza sativa, Secale cereale, Sorghum bicolor, Sorghum vulgare, millet (e.g., Pennisetum glaucum, proso millet (Panicum miliaceum), Setaria italica, Eleusine coracana), Helianthus annuus, Carthamus tinctorius, Triticum aestivum, Glycine max, Nicotiana tabacum, Solanum tuberosum, Arachis hypogaea, Gossypium barbadense, Gossypium hirsutum, Ipomoea batatus, Manihot esculenta, Coffea spp., Cocos nucifera, Ananas comosus, Citrus spp., Theobroma cacao, Camellia sinensis, Musa spp., Persea americana, Ficus casica, Psidium guajava, Mangifera indica, Olea europaea, Carica papaya, Anacardium occidentale, Macadamia integrifolia, Prunus amygdalus, Beta vulgaris, Saccharum spp., oats, barley, vegetables, ornamental plants, and coniferous plants, but are not limited thereto.

[0239] Vegetables include members of the genus i such as tomato (Lycopersicon esculentum), lettuce (e.g., Lactuca sativa), green bean (Phaseolus vulgaris), lima bean (Phaseolus limensis), butter bean, kidney bean (Phaseolus vulgaris), cowpea (Vigna unguiculata), pigeon pea (Cajanus cajan), yam bean, kudzu, leguminous plants, pea (Pisum spp.), and cucumber (Cucumis sativus), cantaloupe (Cucumis cantalupensis), and muskmelon (Cucumis melo). Ornamental plants include Rhododendron spp., Hydrangea macrophylla, Hibiscus rosa-sinensis, Rosa spp., Tulipa spp., Narcissus spp., Petunia hybrida, Dianthus caryophyllus, Euphorbia pulcherrima, and chrysanthemum.

[0240] Examples of coniferous trees that can be used in the practice of the present invention include, for example, pines such as Pinus taeda, Pinus elliotii, Pinus ponderosa, Pinus contorta, and Pinus radiata, Pseudotsuga menziesii, Tsuga canadensis, Picea glauca, Sequoia sempervirens; firs such as Abies amabilis and Abies balsamea, and cedars such as Thuja plicata and Chamaecyparis nootkatensis. In certain embodiments, the plants of the present invention are crop plants (e.g., corn, alfalfa, sunflower, Brassica, soybean, cotton, safflower, peanut, sorghum, wheat, millet, tobacco, etc.). In other embodiments, corn or soybean plants are used.

[0241] Diseases and parasites that can be effectively reduced by treatment with one or more ascalosides and one or more fungicides according to the present disclosure can affect any part of the plant (e.g., seeds, roots, stems, leaves, and spikes).

[0242] Fungal and bacterial pathogens that can be controlled with the disclosed combinations include Botrytis cinerea, Cersospora spp, Cercospora sojina, Cercospora beticola, Cercospora canescens, Alternaria solani, Alternaria brassicae, Blumeria graminis f. sp. Tritici, Erysiphe necator, Podosphaera xanthii, Podosphaera leucotricha, 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, Peronospora lamii, Plasmopara obduscens, Pythium cryptoirregulare, Pythium aphanidermatum, Pythium irregulare, Pythium sylvaticum, Pythium myriotylum, Pythium ultimum, Phytophthora capsici, Phytophthora nicotianae, Phytophthora infestans, Phytophthora tropicalis, Phytophthora sojae, Fusarium graminearum, Fusarium solani, Fusarium oxysporum, Fusarium graminicola, Gibberella zeae, Colletotrichum graminicola, Phakopsorasp., Phakopsora meibomiae, Phakopsora pachyrizi, Puccinia triticina, Puccinia recondita, Puccinia striiformis, Puccinia graminis, Puccinia spp., Venturia inaequalis, Verticillium spp, Erwinia amylovora, Monilinia fructicola, Monilinia lax, Monilinia fructigena, Uncinula necator, Gymnosporangium sabinae, Hemileia vastatrix, Phakopsora pachyrhizi, Phakopsora meibomiae, Uromyces appendiculatus, Albugo candida, Bremia lactucae, Peronospora pisi, P. brassicae, Pseudoperonospora humuli, Pseudoperonospora cubensis, Pythium ultimum; leafspot, 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, Sclerotinia sclerotiorum, Fusarium culmorum, Phytophthora cactorum, Pythium ultimum, Rhizoctonia solani, Rhizopus oryzae, Sclerotium rolfsii, SeptoriaThose selected from nodorum, Botrytis cinerea, Xanthomonas oryzae, Pseudomonas lachrymans, Erwinia amylovora, Venturia inaequalis, Tilletia caries, Ustilago nuda, Ustilago avenae, Pellicularia sasakii, Pyricularia oryzae, Leptosphaeria nodorum, Pseudocercosporrela herpotrichoides, Pyrenophora teres, Pyrenophora graminea and the like are included, but not limited thereto. In some embodiments, ascarioside and one or more fungicides are used to control forma leaf spot, forma cancer, powdery mildew, yellow rust, brown rust, brown spot, Septoria leaf and blight of cereals including barley, rye, wheat, oats and the like.

[0243] Specific diseases include anthracnose (Colletotrichum spp. / Microdochium panattonianum of lettuce, affecting various crops), gray mold (e.g., gray mold / Botrytis cinerea, affecting various crops), downy mildew (affecting crops), white blister / white rust (Albugo candida, typical in Brassica), Fusarium wilt and rot (Fusarium species including F. solani and F. oxysporum), powdery mildew (affecting crops), rust (several species, e.g., Puccinia sorghi of sweet corn, Uromyces appendiculatus of beans, puccinia allii of spring onions and affecting crops, e.g., Asian soybean rust), Rhizoctonia root rot (Rhizoctonia solani, generally lettuce bottom rot / cruciferous wire stem, affecting crops), sclerotinia (S. sclerotiorum and S. minor, affecting most vegetable crops), sclerotium rots (Sclerotium rolfsii and S. cepivorum, affecting crops), target spot (alternaria solani, affecting tomatoes), damping-off (Pythium, Rhizoctonia, Phytophthora, Fusarium, or Aphanomyces, affecting crops), cavity spot (Pythium sulcatum, affecting carrots), clubroot (plasmodiophora brassicae, typically in Brassica), tuber diseases (affecting potatoes and sweet potatoes), Phoma species (affecting many vegetable crops), leaf blight in carrots (alternaria dauci), black root rot (various species in various crops, affecting crops), and red root complex (affecting beans), common bean Aphanomyces root rot (Aphanomyces euteiches pv.Phaseoli (affecting beans), aschocyta collar rot (affecting peas), Gummy stem blight (Didymella bryoniae, affecting cucumbers), brown spot disease (Alternaria cucumerina and A. alternata (Cucurbitaceae)); root rot ((Leptosphaeria maculans, affecting Brassica)); Ring spot (Mycosphaerella brassicicola, affecting Brassica); late blight (Septoria apiicola, affecting celery); Cercospora leaf spot (Cercospora beticola, affecting beets); Leaf blight (Septoria petroelini, affecting parsley); Septoria spot (Septoria lactucae, affecting lettuce); Leaf blight (Stemphylium vesicarium, affecting spring onions); and Leaf blight (Alternaria dauci, affecting carrots) are included, but not limited to these.

[0244] In certain embodiments, plant diseases that can be treated, reduced, or prevented by the compositions and / or methods described herein include plant diseases caused by fungi, viruses or viroids, protozoa, bacteria, etc., such as Asian soybean rust (ASR), gray mold, spot disease, Frogeye leaf spot, late blight, damping-off complex, leaf rot, black spot, root rot, belly rot, southern blight, powdery mildew, anthracnose leaf spot, downy mildew, red rot, fusarium head blight (FHB), sudden death syndrome (SDS), damping-off caused by Fusarium spp., stem rot of corn, brown rust, black rust, yellow rust, wheat rust, rust, apple scab, wilt, fire blight, and brown rot, but not limited to these.

Examples

[0245] Example 1: A composition containing an ascaroside is applied at 25 mg / acre to a winter wheat crop inoculated with Fusarium head blight alone and in combination with a conventional fungicide (PROLINE®). Application of the ascaroside in combination with the fungicide provided additional protection against Fusarium head blight.

[0246] Example 2: A composition containing an ascaroside is applied at 250 mg / ac to soybean crops both alone and in combination with certain conventional fungicides (chlorothalonil and APROACH POWER® containing pyoxystrobin and cyproconazole). Application of the ascaroside alone was found to provide low to moderate protection against Asian soybean rust, 20-40%. The combination of the ascaroside with the conventional fungicide provided additional protection from Asian soybean rust and also resulted in improved yields compared to application of the fungicide alone.

[0247] Example 3: A composition containing a commercial ascaroside formulation, PHYTALIX®, and a triazole fungicide (tebuconazole) was applied via foliar spray to wheat plants grown under greenhouse and / or growth chamber conditions. The composition was applied at a rate equivalent to the label rate of tebuconazole and ascaroside of 25 mg / ac. Three control groups were treated with 1) a mock composition without fungicide or ascaroside, 2) a composition containing only tebuconazole (at the label rate), or 3) a composition containing only the ascaroside composition (at 25 mg / ac equivalent). 48 hours after treatment, the plants were inoculated with the fungal pathogen Bipolaris sorokiniana. All plants were scored for disease symptoms several days after inoculation. As shown in Figure 2, the combination treatment reduced disease symptoms much more effectively than either the ascaroside alone or tebuconazole alone.

[0248] Example 4: A composition containing PHYTALIX® and PROSARO™ (a commercial fungicide containing a mixture of the two triazole fungicides tebuconazole and prothioconazole), a commercially available ascaloside formulation, was applied via foliar spraying to wheat plants grown in a randomized small plot format under field conditions. The composition was applied at a rate corresponding to the label rate of PROSARO™ and 25 mg / ac of ascaloside. Three control groups were treated with 1) a mock composition containing no fungicide or ascaloside, 2) a composition containing only PROSARO™ (at the label rate), or 3) a composition containing only the ascaloside composition (at 25 mg / ac equivalent). As shown in Figure 3, the combination treatment is more effective than either product alone in reducing the incidence of Fusarium head blight (FHB).

[0249] Example 5: A composition containing PHYTALIX® and prothioconazole, a commercially available ascaloside formulation, was applied via foliar spraying to wheat plants grown in a randomized small plot format under field conditions. The composition was applied at a rate corresponding to the label rate of prothioconazole and 25 mg / ac of ascaloside. Three control groups were treated with 1) a mock composition containing no fungicide or ascaloside, 2) a composition containing only prothioconazole (at the label rate), or 3) a composition containing only the ascaloside composition (at 25 mg / ac equivalent). As shown in Figure 4, the combination treatment is more effective than either product alone in reducing the severity of Septoria tritici blotch symptoms.

[0250] Example 6: A composition containing the commercially available ascaloside formulation PHYTALIX® and a mixture with propiconazole and pydiflumetofen, a class 7 fungicide, was applied via foliar spraying to wheat plants grown in a randomized small plot format under field conditions. The composition was applied at the label rate of propiconazole and pydiflumetofen, and at a rate corresponding to 25 mg / ac of ascaloside. Three control groups were treated with 1) a mock composition containing no fungicide or ascaloside, 2) a composition containing only propiconazole and pydiflumetofen (at the label rate), or 3) a composition containing only the ascaloside composition (at 25 mg / ac equivalent). As shown in Figure 5, the combined treatment is more effective than either product alone in reducing the severity of fusarium head blight symptoms and results in a higher yield than either treatment alone.

[0251] Example 7: A composition containing the commercially available ascaloside formulation PHYTALIX® and prothioconazole was applied via foliar spraying to wheat plants grown in a randomized small plot format under field conditions. The composition was applied at the label rate of prothioconazole and at 25 mg / ac of ascaloside. Three control groups were treated with 1) a mock composition containing no fungicide or ascaloside, 2) a composition containing only prothioconazole (at the label rate), or 3) a composition containing only the ascaloside composition (at 25 mg / ac equivalent). As shown in Figure 6, the combined treatment is more effective than either product alone in reducing the severity of fusarium head blight symptoms.

[0252] Example 8: A composition containing ascaloside (ascr#18) was applied at a rate of 250 mg / ac via foliar spraying to soybean crops cultivated under field conditions at two sites in Brazil in regions prone to Asian soybean rust (ASR) infection. The ascaloside composition was applied alone or in combination with certain conventional fungicides (chlorothalonil and APROACH POWER® containing picoxystrobin and cyproconazole), leaving separate control plots untreated or treating them with the conventional fungicide alone. Application of ascaloside alone was found to provide moderate (e.g., 20 - 40%) protection against Asian soybean rust compared to untreated controls (Figure 9). The combination of ascaloside and the conventional fungicide provided additional protection against Asian soybean rust compared to application of the fungicide alone or ascaloside alone (Figures 9 and 10). The combination of ascaloside and the conventional fungicide resulted in an increase in yield compared to treatment with the conventional fungicide alone (Figures 7 and 8).

[0253] Example 9: A composition containing the commercially available ascaloside formulation PHYTALIX® and a commercially available fungicide containing a mixture of the strobilurin fungicide picoxystrobin and chlorothalonil was applied via foliar spraying to soybean plants grown under field conditions. This composition was applied at the label rate of the commercially available fungicide and at a rate equivalent to 205 mg / ac of ascaloside. Three control groups were treated with 1) a mock composition containing no fungicide or ascaloside, 2) a composition containing only the commercially available fungicide (at the label rate), and 3) a composition containing only the ascaloside composition (at 205 mg / ac equivalent). As shown in Figure 11, the combination treatment more effectively reduced disease symptoms than either ascaloside alone or the commercially available fungicide alone.

[0254] Example 10: A composition comprising a mixture of the ascaloside formulation PHYTALIX® and a commercial formulation of the strobilurin fungicide azoxystrobin was grown under field conditions and applied via foliar spray to soybean plants inoculated with Asian soybean rust. The composition was applied at the label rate of the commercial fungicide and at a rate equivalent to 50 mg / ac of ascaloside. Four control groups were treated with 1) no fungicide or ascaloside, 2) azoxystrobin fungicide alone (at the label rate), and 3) ascaloside composition alone (at 50 mg / ac equivalent), and 4) only Trivapro, the top-class commercial fungicide containing a three-way mixture of propiconazole, azoxystrobin, and benzovindiflupyr. As shown in FIGS. 12 and 13, the combined treatment with ascaloside reduced disease symptoms more than ascaloside alone or commercial fungicide alone, increased yield more effectively, and was superior to the top-class three-way mixture.

[0255] Example 11: A composition containing a mixture of PHYTALIX® (an ascaloside formulation) and azoxystrobin (a strobilurin fungicide) was applied via foliar spray to wheat plants grown in a growth chamber and inoculated with Bipolaris sorokiniana, a fungal pathogen that causes spot blotch. A commercially available azoxystrobin composition was diluted to provide an application rate equivalent to 1 / 20 of the standard label application rate, and a mixture containing the ascaloside composition (PHYTALIX®) at a concentration equivalent to an application of 25 mg of ascaloside per acre showed excellent disease control (Figure 14, right column). Three control groups were included for comparison: 1) no fungicide or ascaloside treatment (mock), 2) azoxystrobin fungicide alone at 1 / 20 label rate (azoxystrobin), and 3) ascaloside composition alone at 25 mg / ac equivalent (PHYTALIX®). These data (Figure 14) show a synergistic effect between the ascaloside composition and azoxystrobin, a strobilurin, and confirm that inclusion of ascaloside in such mixtures allows for a reduction in the amount of fungicide. Notably, the mixture showed the highest level of pathogen suppression, indicating that resistance is less likely to occur.

[0256] Example 12: A composition containing a mixture of the ascaloside formulation PHYTALIX® and a commercial formulation of the SDHI fungicide fluxapyroxad was applied via foliar spray to wheat plants grown in a growth chamber and inoculated with Bipolaris sorokiniana, a fungal pathogen that causes spot blotch. The mixture containing the diluted commercial fluxapyroxad composition provided an application rate equivalent to 1 / 20 of the standard label application rate, and a concentration equivalent to an application of 25 mg of ascaloside per acre of the ascaloside composition (PHYTALIX®) showed excellent disease control (Figure 15. Fluxapyroxad right column). Three control groups were included for comparison: 1) no fungicide or ascaloside treatment (mock), 2) SDHI fungicide only at 1 / 20 of the label rate (fluxapyroxad), and 3) ascaloside composition only at 25 mg / ac equivalent (PHYTALIX®). These data demonstrate a synergistic effect between the ascaloside composition and fluxapyroxad, an SDHI, and confirm that including ascaloside in such mixtures allows for a reduction in the amount of fungicide. Notably, the mixture showed the highest level of pathogen suppression and a low likelihood of resistance development.

[0257] Example 13: The stability of the combination of PHYTALIX® with various other commercially available fungicide products was studied. Two sets of samples were prepared by replicating in a tank mixture formulation (e.g., PHYTALIX® and the commercial product were diluted in water at their labeled rates and the PHYTALIX® concentrate, which is the formulation mixture, was added directly to the formulated commercial product). The samples were stored at room temperature and at 40 °C (for accelerated degradation) and the PHYTALIX® content was monitored periodically using HPLC / MS quantification. The results for 6 months are summarized below. The data surprisingly demonstrate that the combination of PHYTALIX® with the commercially available fungicides in both the concentrated formulation and the tank mixture concentrate is stable (e.g., with respect to the ascaloside content) for at least 6 months or at least 12 months of shelf life, despite the incredibly low ascaloside content present in each formulation. This finding is particularly surprising in light of the fact that formulating mixtures of chemical and biological components can generally be quite difficult due to issues of non-compatibility of such components with each other.

Table 1

Table 2

[0258] Example 14: Field trials were conducted to evaluate the efficacy of ascaloside seed treatment alone and in combination with multi-way commercially available fungicide seed treatments for controlling bacterial leaf streak in wheat. Prior to planting, wheat seeds were treated with the commercially available ascaloside formulation PHYTALIX® at a rate of 2.5 ppm alone or in combination with Apron Maxx® (mefenoxam, fludioxonil) at the labeled rate. Plots grown from mock-treated seeds and from seeds treated only with Apron Maxx® were included as controls. The incidence of bacterial leaf streak in the treatment groups was scored 2 months after planting, and the results were plotted in Figure 16. As shown in Figure 16, plots grown from seeds treated with the combination of PHYTALIX® and Apron Maxx® had the lowest incidence of bacterial leaf streak, demonstrating additive and / or synergistic activity exceeding that of either product alone for the control of this pathogen in wheat.

[0259] Example 15: Field trials were conducted to evaluate the efficacy of ascaloside seed treatment alone and in combination with multi-way commercially available fungicide seed treatments for extending the photosynthetic period of corn. Prior to planting, corn seeds were treated with the commercially available ascaloside formulation PHYTALIX® at a rate of 5 ppm alone or in combination with Apron Maxx® (mefenoxam, fludioxonil) at the labeled rate. Plots grown from mock-treated seeds and from seeds treated only with Apron Maxx® were included as controls. The stay-green effect (scale 1 - 9) was measured 156 days after planting, and the results are shown in Figure 17. As shown in Figure 17, the combination of PHYTALIX® and Apron Maxx® showed the highest stay-green score, demonstrating additive and / or synergistic activity exceeding that of either product alone.

[0260] Example 16: Field trials were conducted to evaluate the effectiveness of ascoroside seed treatment alone and in combination with multi-way commercial fungicide seed treatments to increase the germination and emergence of soybean seeds. Prior to planting, soybean seeds were treated with the commercial ascoroside formulation PHYTALIX® applied alone at a rate of 5 ppm or in combination with Apron Maxx™ (mefenoxam, fludioxonil) at the labeled rate. Plots grown from mock-treated seeds and from seeds treated only with Apron Maxx™ were included as controls. The stand count for each plot was measured at 50% germination and extrapolated to the number of seedlings per acre. The results are plotted in FIG. 18. As shown in FIG. 18, the combination of PHYTALIX® and Apron Maxx™ showed the highest stand count demonstrating additive and / or synergistic activity exceeding either product alone.

[0261] The compounds, compositions, and methods of the present application are intended to encompass variations and adaptations developed using information from the embodiments described in this disclosure. Adaptations or modifications of the methods and processes described herein may be made by those of ordinary skill in the relevant art. The use of headings in this disclosure is understood to be provided for the convenience of the reader.

[0262] The presence and / or placement of headings is not intended to limit the scope of the subject matter described herein. Unless otherwise specified, embodiments located in one section of this application apply to other embodiments throughout the application, both alone and in combination. Throughout the description, when a composition, compound, or product is described as having, including, or comprising a particular component, or when a process and method are described as having, including, or comprising a particular step, it is further contemplated that there are articles, devices, and systems of this application that consist essentially of, or consist of, the recited components, and that there are processes and methods according to this application that consist essentially of, or consist of, the recited treatment steps. It should be understood that the order of steps or sequence of a particular order for performing a particular operation is not important as long as the described method is operable. Further, two or more steps or operations may be performed simultaneously.

[0263] All publications and patent applications mentioned herein are indicative of the level of those skilled in the art to which the invention pertains. All publications and patent applications are hereby incorporated by reference into this specification to the same extent as if each individual publication or patent application was specifically and individually indicated to be incorporated by reference. The foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, but it will be apparent that certain changes and modifications may be practiced within the scope of the appended claims.

Claims

1. A method for enhancing the activity of a fungicide, comprising simultaneously administering the fungicide and one or more ascalosides to a plant, a part of a plant, or soil surrounding the plant or part of a plant.

2. The method according to claim 1, wherein the fungicide is a biological fungicide.

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

4. A method for enhancing the activity of a fungicide, comprising simultaneously administering the fungicide and one or more ascalosides to a plant or part of a plant, or to the soil surrounding the plant or part of a plant, a. The fungicide includes a triazole fungicide. b. The fungicide is Q ｏ I. Contains fungicides, or c. The method wherein the fungicide comprises an SDHI fungicide.

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

6. The method according to claim 4, wherein the triazole fungicide is selected from the group consisting of mycrobutanil, epoxyconazole, ipconazole, metconazole, uniconazole-P, uniconazole, triticonazole, tricyclazole, triazbutyl, triadimenol, triadimephone, tetraconazole, tebuconazole, simeconazole, quinconazole, prothioconazole, propiconazole, penconazole, imibenconazole, hexaconazole, fluconazole, fluconazole-cis, flutriafor, flusilazole, fluquinconazole, flutrimazole, fenbuconazole, etaconazole, diniconazole-M, diniconazole, difenoconazole, diclobutrazol, cyproconazole, bromconazole, vitertanol, azaconazole, and amisulbrom.

7. The aforementioned Q ｏ The method according to claim 4, wherein the fungicide is a strobilurin selected from the group consisting of azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, phenamistrobin, dimoxystrobin, fluoxastrobin, methaminostrobin, mandestrobin, pyrametostrobin, pyrazoxystrobin, kresoxime-methyl, phenamidone, or famoxadone.

8. The method according to claim 4, wherein the SDHI fungicide is a benzamide fungicide that inhibits succinate dehydrogenase (SDH) complex II, and the benzamide fungicide is selected from the group consisting of benodanil, flurenoxadiazam, flutolanil, mebenil, mepronil, fluopyram, benzohydroxamidic acid, flumetobel, flupicolide, flupimoide, thioxymide, trchlamide, zarilamide, and zoxamide.

9. The SDHI fungicide is a carboxamide fungicide that inhibits succinate dehydrogenase (SDH) complex II, and the carboxamide fungicide is Oxathiine fungicide, francarboxamide fungicide, Pyrazinecarboxamide fungicide, Pyrazole carboxamide fungicide, and The composition according to claim 4, selected from the group consisting of pyridinecarboxamide fungicides.

10. The method according to claim 9, wherein the carboxamide fungicide is selected from the group consisting of carboxyne, oxycarboxyne, fenflam, flucarbanil, metofloxam, pyraziflumid, benzovindiflupir, bixafen, fluveneteram, fluindapir, fluxapyroxad, flametopyr, impilfluxam, isoflucipram, isopyrazam, penflufen, penthiopyrad, pidflumetofen, pyrapropoin, sedaxane, etaboxam, tifluzamide, boscalid, and cyclobutrifluram.

11. The method according to claim 4, wherein the SDHI fungicide comprises a thiophenamide fungicide, and the thiophenamide fungicide is isofetamide.

12. The method according to claim 1, wherein the increased total yield of the plant is greater than the yield of the plant treated with the fungicide alone plus the yield of the plant treated with one or more ascalosides alone.

13. The method according to claim 1, wherein it provides increased disease protection, the increased disease protection being greater than the disease protection provided by treatment with one or more ascalosides alone, in addition to the disease protection provided by treatment with the fungicide alone.

14. The method according to claim 1, wherein the simultaneous administration includes applying the fungicide and the one or more ascalosides in the form of separate formulations.

15. The method according to claim 1, wherein the simultaneous administration includes applying the fungicide and one or more ascalosides in the form of a single formulation.

16. The plant or part of the plant (i) Tobacco, Arabidopsis thaliana, tomato, barley, potato, sweet potato, yam, cotton, soybean, strawberry, sugar beet, corn, rice, wheat, rye, oat, sorghum, millet, legume, 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; (ii) Corn (Zea mays), Brassica (e.g., B. napus, B. rapa, B. juncea), Brassica, especially useful as a source of seed oil, alfalfa (Medicago sativa), rice (Oryza sativa), rye (Secale cereale), sorghum (Sorghum bicolor, Sorghum vulgare), millet (e.g., pearl millet (Pennisetum glaucum), proso millet (Panicum miliaceum), foxtail millet (Setaria italica), finger millet (Eleusine coracana)), sunflower (Helianthus) Annuus, safflower (Carthamus tinctorius), wheat (Triticum aestivum), soybeans (Glycine max), tobacco (Nicotiana tabacum), potatoes (Solanum tuberosum), peanuts (Arachis hypogaea), cotton (Gossypium barbadense, Gossypium hirsutum), sweet potatoes (Ipomoea batatus), cassava (Manihot esculenta), coffee (Coffee spp.), coconut (Cocos nucifera), pineapple (Ananas) comosus, citrus fruits (Citrus spp.), cocoa (Theobroma cacao), tea (Camellia sinensis), banana (Musa spp.), avocado (Persea americana), fig (Ficus casica), guava (Psidium guajava), mango (Mangifera indica), olive (Olea europaea), papaya (Carica papaya), cashew (Anacardium occidentale), macadamia (Macadamia integrifolia), almond (Prunus) The plants or plant parts of sugar beets (beta vulgaris), sugarcane (Saccharum spp.), oats, barley, vegetables, ornamental plants, and coniferous plants; (iii) A vegetable plant or part of a plant, wherein the vegetable is a tomato (Lycopersicon esculentum), lettuce (e.g., Lactuca sativa), kidney bean (Phaseolus vulgaris), lima bean (Phaseolus limensis), butter bean, kidney bean (Phaseolus vulgaris), cowpea (Vigna unguiculata), pigeon bean (Cajanus cajan), yam bean, kudzu, legume, pea (i Ornamental plants are selected from members of the genus i, such as cucumber (C. sativus), cantaloupe (C. cantalupensis), and muskmelon (C. melo), including azalea (Rhododendron spp.), hydrangea (Macrophylla hydrangea), hibiscus (Hibiscus rosasanensis), rose (Rosa spp.), tulip (Tulipa spp.), daffodil (Narcissus spp.), petunia (Petunia hybrida), carnation (Dianthus caryophyllus), and poinsettia (Euphorbia). Plants or plant parts, including pulcherrima, and chrysanthemums; (iv) Coniferous plants or parts of plants, wherein the coniferous plant is Pinus taeda, Pinus elliotii, Pinus ponderosa, Pinus contorta, and Pinus radiata, Pseudotsuga menziesii, Tsuga canadensis, Sitka spruce, Sequoia sempervirens; European fir (Abies amabilis) and balsam fir (Abies balsamea), and Western red cheddar (Thuja) A plant or plant part selected from *Plicata*, and Alaska Yellow Cheddar (*Chamaecyparis nottkatensis*); or (v) A plant or plant part of a crop plant, wherein the crop plant is selected from corn, alfalfa, sunflower, brassica, soybean, cotton, safflower, peanut, sorghum, wheat, millet, or tobacco. The method according to claim 1, selected from the following.

17. The method effectively reduces diseases, the diseases being anthracnose (Colletotrichum spp. / Microdochium panattonianum in lettuce, affecting a variety of crops), gray mold (e.g., gray mold / Botrytis cinerea, affecting crops), downy mildew (affecting crops), white blister (Albugo candida, typical in the Brassica genus), Fusarium wilt and rot (Fusarium species including F. solani and F. oxysporum), powdery mildew (affecting crops), rust (several species, e.g., Puccinia sorgh in sweet corn, Uromyces in beans) Appendiculatus, Puccinia allii of spring onions, and affecting crops, e.g., Asian soybean rust), Rhizoctonia root rot (Rhizoctonia solani, commonly known as lettuce blossom end rot / wire stem of brassicas, affecting crops), Sclerotinia rot (S. sclerotiorum and S. minor, affecting most vegetable crops), Sclerotium rots (Sclerotium rolfsii and S. cepivorum, affecting crops), target spot (Alternaria solani, affecting tomatoes), damping-off (Pythium, Rhizoctonia, Late blight, Fusarium, or Aphanomyces, affecting crops), cavity spot (Pythium sulcatum, affects carrots), root gall (Plasmodiophora brassicae, typically in Brassica), tuber diseases (affects potatoes and sweet potatoes), fuzzy fungus species (affects many vegetable crops), leaf blight in carrots (Alternaria daucii), black root rot (affects various species and crops in various crops), and red root complex (affects beans), kidney bean aphanomyces root rot (Aphanomyces euteiches pv. Phaseoli, affects beans), Aschocyta collarrot (affects peas), Gummy stem bright (Didymella bryoniae, affecting cucumbers), brown spot disease (Alternaria cucumerina and A. alternata (Cucurbitaceae)); root rot (Leptosphaeria maculans, affecting brassica); ring spot (Mycosphaerella brassicola, affecting brassica); late bright (Septoria apiicola, affecting celery); Cercospora leaf spot (Cercospora beticola, affecting beets); Leaf bright (Septoria The method according to claim 1, selected from petroelini (affects parsley); Septoria spot (affects lettuce); Leaf bright (affects spring onions); and Leaf bright (affects carrots).

18. The method according to claim 17, wherein the disease is Asian soybean rust.

19. The one or more ascalosides described above have structure (I) 【Chemistry 17】 It has, in the formula, Z is replaced by C as desired. ２～４０ It is an aliphatic group, R ａ and R ｂ each independently is -H, or C １～２０ aliphatic, C １～２０ acyl, C １～２０ heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bonding functional group, sulfur bonding functional group, silicon bonding functional group, C ２～２０ carbonate (e.g., moiety -C(O)OR ｃ ), C ２～２０ carbamate (e.g., moiety -C(O)N(R ｃ ) ２ ), C ２～２０ thioester (e.g., moiety -C(S)R ｃ ), C ２～２０ thiocarbonate (e.g., moiety -C(S)OR ｃ ), C ２～２０ dithiocarbonate (e.g., moiety -C(S)SR ｃ ), C<00000​​​​​​​​​​​​​​​

20. Z is i. -CH(CH ３ )-R １ (R １ C is replaced as desired. １～４０ (It is an aliphatic group.) ii. -CH(CH ３ )-(CH ２ ) ｎ－ CO ２ R ２ (n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) iii. -CH(CH ３ )-(CH ２ ) ｎ－ CH = CH - CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) iv. -CH(CH ３ )-(CH ２ ) ｎ－ CH(OH)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) v. -CH(CH ３ )-(CH ２ ) ｎ－ C(O)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) vi. - (CH ２ ) ｎ－ CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) vii. - (CH ２ ) ｎ－ CH = CH - CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) viiii. - (CH ２ ) ｎ－ CH(OH)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules via carbon-containing linker moieties), and ix. -(CH ２ ) ｎ－ C(O)-CH-CO ２ R ２ (n is an integer from 1 to 40, and R ２ is -H, a metal cation, an optionally substituted C １～２０ aliphatic group, an optionally substituted C １～２０ heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety). x. -CH(CH ３ )- (CH ２ ) ｎ－ CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ is independently -H, an optionally substituted C １～２０ aliphatic group, an optionally substituted C １～２０ heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety). xi. -CH(CH ３ )-(CH ２ ) ｎ－ CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xii. -CH(CH ３ )-(CH ２ ) ｎ－ CH(OH)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xiii. -CH(CH ３ )-(CH ２ ) ｎ－ C(O)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xiv. - (CH ２ ) ｎ－ CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xv. - (CH ２ ) ｎ－ CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xvi. - (CH ２ ) ｎ－ CH(OH)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules via carbon-containing linker moieties), and xvii. - (CH ２ ) ｎ－ C(O)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ The method according to claim 19, selected from the group consisting of a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another askaloside molecule via a carbon-containing linker moiety.

21. The method according to claim 19, wherein both Ra and Rb are -H.

22. The one or more ascalosides 【Chemistry 101】 The method according to claim 19, wherein a selection is made from the group consisting of the following, and in the formula, x is an integer from 1 to 22.

23. The method according to claim 20, wherein Z is -CH(CH3)-(CH2)n-CO2R2, where n is an integer from 1 to 40, and R2 is -H, a metal cation, optionally a substituted C1-20 aliphatic group, optionally a substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

24. The method according to claim 1, wherein one or more ascalosides include ascr#18.

25. The one or more ascalosides 【Chemical Engineering 102】 The method according to claim 19, wherein a selection is made from the group consisting of the following, and in the formula, y is an integer from 1 to 20.

26. The method according to claim 20, wherein Z is -CH(CH3)-(CH2)n -CH=CH-CO2 R2, where n is an integer from 1 to 40, and R2 is -H, a metal cation, optionally a substituted C1-20 aliphatic group, optionally a substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

27. ​​The method according to claim 1, wherein one or more ascalosides include ascr#7.

28. The method according to claim 20, wherein Z is -(CH₂)n-CO₂R₂, where n is an integer from 1 to 40, and R₂ is -H, a metal cation, optionally a substituted C1-20 aliphatic group, optionally a substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

29. The method according to claim 1, wherein one or more ascalosides are selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

30. A composition comprising one or more ascalosides and one or more fungicides.

31. The composition according to claim 30, wherein the one or more fungicides include a biological fungicide.

32. The composition according to claim 30, wherein the one or more fungicides include a chemifungicide selected from the group consisting of azoles, strobilurin, carboxamides, nitrogenous heterocyclyl compounds, carbamates and dithiocarbamates, guanidines, antibiotics, organometallic compounds, sulfur-containing heterocyclyl compounds, organophosphorus compounds, organochlorine compounds, nitrophenyl derivatives, inorganic active compounds, and combinations thereof.

33. A composition comprising one or more ascalosides and one or more fungicides, a. The one or more fungicides include a triazole fungicide. b. The one or more fungicides mentioned above, Q ｏ I. Contains fungicides, or c. The composition comprising one or more fungicides, wherein the one or more fungicides include an SDHI fungicide.

34. The composition according to claim 33, wherein the triazole fungicide is prothioconazole or tebuconazole.

35. The composition according to claim 33, wherein the triazole fungicide is selected from the group consisting of mycrobutanil, epoxyconazole, ipconazole, metconazole, uniconazole-P, uniconazole, triticonazole, tricyclazole, triazbutyl, triadimenol, triadimephone, tetraconazole, tebuconazole, simeconazole, quinconazole, prothioconazole, propiconazole, penconazole, imibenconazole, hexaconazole, fluconazole, fluconazole-cis, flutriafor, flusilazole, fluquinconazole, flutrimazole, fenbuconazole, etaconazole, diniconazole-M, diniconazole, difenoconazole, diclobutrazol, cyproconazole, bromconazole, vitertanol, azaconazole, and amisulbrom.

36. The aforementioned Q ｏ The composition according to claim 33, wherein the fungicide is a strobilurin selected from the group consisting of azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, phenamistrobin, dimoxystrobin, fluoxastrobin, methaminostrobin, mandestrobin, pyrametostrobin, pyrazoxystrobin, kresoxim-methyl, phenamidone, and famoxadone.

37. The composition according to claim 33, wherein the SDHI fungicide is a benzamide fungicide that inhibits succinate dehydrogenase (SDH) complex II, and the benzamide fungicide is selected from the group consisting of benodanil, flurenoxadiazam, flutolanil, mebenil, mepronil, fluopyram, benzohydroxamidic acid, flumetobel, flupicolide, flupimoide, thioxymide, trchlamide, zarilamide, and zoxamide.

38. The SDHI fungicide is a carboxamide fungicide that inhibits succinate dehydrogenase (SDH) complex II, and the carboxamide fungicide is Oxathiine fungicide, francarboxamide fungicide, Pyrazinecarboxamide fungicide, Pyrazole carboxamide fungicide, and The composition according to claim 33, selected from the group consisting of pyridinecarboxamide fungicides.

39. The composition according to claim 38, wherein the carboxamide fungicide is selected from the group consisting of carboxyne, oxycarboxyne, fenflam, flucarbanil, metofloxam, pyraziflumid, benzovindiflupir, bixafen, fluveneteram, fluindapir, fluxapyroxad, flametopyr, impilfluxam, isoflucipram, isopyrazam, penflufen, penthiopyrad, pidflumetofen, pyrapropoin, sedaxane, etaboxam, tifluzamide, boscalid, and cyclobutrifluram.

40. The composition according to claim 33, wherein the SDHI fungicide comprises a thiophenamide fungicide, and the thiophenamide fungicide is isofetamide.

41. The composition according to claim 30, wherein at least one ascaloside and the fungicide are present in an effective amount, and the effective amount provides synergistic activity in controlling fungal diseases.

42. The composition according to claim 41, wherein the disease is Asian soybean rust.

43. The composition effectively reduces diseases, the diseases being anthracnose (Colletotrichum spp. / Microdochium panattonianum in lettuce, affecting a variety of crops), gray mold (e.g., gray mold / Botrytis cinerea, affecting crops), downy mildew (affecting crops), white blister (Albugo candida, typical in the Brassica genus), Fusarium wilt and rot (Fusarium species including F. solani and F. oxysporum), powdery mildew (affecting crops), rust (several species, e.g., Puccinia sorgh in sweet corn, Uromyces in beans) Appendiculatus, Puccinia allii of spring onions, and affecting crops, e.g., Asian soybean rust), Rhizoctonia root rot (Rhizoctonia solani, commonly known as lettuce blossom end rot / wire stem of brassicas, affecting crops), Sclerotinia rot (S. sclerotiorum and S. minor, affecting most vegetable crops), Sclerotium rots (Sclerotium rolfsii and S. cepivorum, affecting crops), target spot (Alternaria solani, affecting tomatoes), damping-off (Pythium, Rhizoctonia, Late blight, Fusarium, or Aphanomyces, affecting crops), cavity spot (Pythium sulcatum, affects carrots), root gall (Plasmodiophora brassicae, typically in Brassica), tuber diseases (affects potatoes and sweet potatoes), fuzzy fungus species (affects many vegetable crops), leaf blight in carrots (Alternaria daucii), black root rot (affects various species and crops in various crops), and red root complex (affects beans), kidney bean aphanomyces root rot (Aphanomyces euteiches pv. Phaseoli, affects beans), Aschocyta collarrot (affects peas), Gummy stem bright (Didymella bryoniae, affecting cucumbers), brown spot disease (Alternaria cucumerina and A. alternata (Cucurbitaceae)); root rot (Leptosphaeria maculans, affecting brassica); ring spot (Mycosphaerella brassicola, affecting brassica); late bright (Septoria apiicola, affecting celery); Cercospora leaf spot (Cercospora beticola, affecting beets); Leaf bright (Septoria The composition according to claim 30, selected from petroelini (affects parsley); Septoria spot (affects lettuce); Leaf bright (affects spring onions); and Leaf bright (affects carrots).

44. The composition according to claim 43, wherein the disease is Asian soybean rust.

45. The one or more ascalosides described above have structure (I) [Chemistry 18] It has, in the formula, Z is replaced by C as desired. ３～４０ It is an aliphatic group, R ａ and R ｂ Each of these independently corresponds to -H or C １～２０ aliphatic, C １～２０ Ashiru, C １～２０ Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bond functional group, sulfur bond functional group, silicon bond functional group, C ２～２０ Carbonates (e.g., partial-C(O)OR) ｃ ), C ２～２０ Carbamates (e.g., partial-C(O)N(R) ｃ ) ２ ), C ２～２０ Thioesters (e.g., partial-C(S)R) ｃ ), C ２～２０ Thiocarbonates (e.g., partial-C(S)OR) ｃ ), C ２～２０ Dithiocarbonates (e.g., partial-C(S)SR) ｃ ), C １～２０ Thiocarbamates (e.g., partial-C(S)N(R) ｃ ) ２ ), optionally substituted, selected from the group consisting of a sugar moiety, a peptide, a polymer chain, or linkage to another ascaloside molecule or via a carbon-containing linker moiety, R ｃ However, in each occurrence, independently, -H and C as desired are substituted. １～１２ Aliphatic, optionally substituted C １～１２ Selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain, or linkage to another ascaloside molecule via a carbon-containing linker moiety, R ａ and R ｂ The composition according to any one of claims 30 to 44, wherein these elements may combine to form a optionally substituted ring containing optionally one or more heteroatoms and optionally one or more unsaturated moieties.

46. Z is i. -CH(CH ３ )-R １ (R １ C is replaced as desired. １～４０ (It is an aliphatic group.) ii. -CH(CH ３ )-(CH ２ ) ｎ－ CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) iii. -CH(CH ３ )-(CH ２ ) ｎ－ CH = CH - CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) iv. -CH(CH ３ )-(CH ２ ) ｎ－ CH(OH)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) v. -CH(CH ３ )-(CH ２ ) ｎ－ C(O)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) vi. - (CH ２ ) ｎ－ CO ２ R ２ (n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) vii. - (CH ２ ) ｎ－ CH = CH - CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) viiii. - (CH ２ ) ｎ－ CH(OH)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) ix. - (CH ２ ) ｎ－ C(O)-CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is -H, a metal cation, or optionally substituted C １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) x. -CH(CH ３ )-(CH ２ ) ｎ－ CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xi. -CH(CH ３ )-(CH ２ ) ｎ－ CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xii. -CH(CH ３ )-(CH ２ ) ｎ－ CH(OH)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xiii. -CH(CH ３ )-(CH ２ ) ｎ－ C(O)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xiv. - (CH ２ ) ｎ－ CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xv. - (CH ２ ) ｎ－ CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This may be a heteroaliphatic group, a optionally substituted aromatic group, a optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety.) xvi. - (CH ２ ) ｎ－ CH(OH)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ (This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules via carbon-containing linker moieties), and xvii. - (CH ２ ) ｎ－ C(O)-CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １～２０ Aliphatic group, optionally substituted C １～２０ The composition according to claim 45, selected from the group consisting of a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or linkage to another ascaloside molecule via a carbon-containing linker moiety.

47. The composition according to claim 45, wherein both Ra and Rb are -H.

48. The one or more ascalosides 【Chemistry 103】 The composition according to claim 45, selected from the group consisting of, where x is an integer from 1 to 22.

49. The composition according to claim 46, wherein Z is -CH(CH3)-(CH2)n-CO2R2, where n is an integer from 1 to 40, and R2 is -H, a metal cation, optionally a substituted C1-20 aliphatic group, optionally a substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

50. The composition according to claim 30, wherein one or more ascalosides include ascr#18.

51. The one or more ascalosides 【Chemical 104】 The composition according to claim 45, selected from the group consisting of, where y is an integer from 1 to 20.

52. The composition according to claim 46, wherein Z is -CH(CH3)-(CH2)n -CH=CH-CO2 R2, where n is an integer from 1 to 40, and R2 is -H, a metal cation, optionally a substituted C1-20 aliphatic group, optionally a substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

53. The composition according to claim 30, wherein one or more ascalosides comprise ascr#7.

54. The composition according to claim 46, wherein Z is -(CH₂)n-CO₂R₂, where n is an integer from 1 to 40, and R₂ is -H, a metal cation, optionally a substituted C1-20 aliphatic group, optionally a substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

55. The composition according to claim 30, wherein one or more ascalosides are selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

56. The composition according to claim 30, in solid form.

57. The composition according to claim 30, in liquid form.

58. The composition according to claim 56 or 57, wherein the composition is storage stable for a period exceeding six months.

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

60. The composition according to claim 30, wherein the fungicide and the ascaloside are present in a weight ratio of fungicide:ascaloside greater than 1000:

1.

61. The composition according to claim 30, which is labeled for application to crops at a lower rate than that of the fungicide alone.

62. The composition according to claim 30, labeled for application to crops at a rate that delivers less than 4 oz of fungicide per acre.

63. A method for treating, reducing, or preventing Asian soybean rust in a soybean crop, comprising applying ascaloside to the soybean crop.

64. A method comprising contacting a plant or plant part susceptible to Asian soybean rust with an effective amount of a composition comprising at least one ascaloside.

65. The method according to claim 63 or 64, wherein the ascaloside is ascr#18.

66. A method for preventing and controlling soybean rust, the method comprising contacting a plant or plant part with an effective amount of a composition comprising at least one ascaloside.

67. The method according to claim 66, wherein the ascaloside is ascr#18.

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