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EP-4735460-A2 - ASCAROSIDES AND HERBICIDAL COMBINATIONS AND METHODS FOR USE

EP4735460A2EP 4735460 A2EP4735460 A2EP 4735460A2EP-4735460-A2

Abstract

Combinations of agents for preventing, treating, or controlling unwanted plants and methods of their use are provided. The combinations comprise at least one ascaroside (or a derivative or analog of an ascaroside) with at least one herbicide. The ascaroside can be combined with at least one herbicide to lessen the phytotoxic effects of the herbicide on the treated crop while simultaneously killing unwanted plants in the applied area. The ascarosides and herbicides may be provided in the same composition or may be applied together (i.e., substantially simultaneously) or sequentially.

Inventors

  • WILMOTH, Gabriel
  • HIDALGO, EDISON
  • MANOHAR, Murli

Assignees

  • Ascribe Bioscience Inc.

Dates

Publication Date
20260506
Application Date
20240628

Claims (20)

  1. CLAIMS What is claimed is: 1. A method for reducing phytotoxic side effects on plants associated with application of an herbicide, said method comprising contacting a plant or a plant part with an effective amount of a combination of agents, said agents comprising at least one ascaroside and at least one herbicide.
  2. 2. The method of claim 1, wherein said effective amount reduces phytotoxic side effects on crop plants as compared to phytotoxic side effects on plants associated with application of the herbicide alone.
  3. 3. The method of claim 1 or 2, wherein said effective amount reduces the phytotoxicity rating on crop plants as compared to the phytotoxicity rating on plants associated with application of the herbicide alone.
  4. 4. The method of any one of claims 1-3, wherein the herbicide is a PPO Herbicide, an Auxin Herbicide, an ALS/AHAS Herbicide, an ACCase Inhibitor Herbicide, a Carotenoid Biosynthesis Inhibitor Herbicide, a Cellulose Inhibitor Herbicide, an EPSP Inhibitor Herbicide, a Glutamine Synthesis Inhibitor Herbicide, a Lipid Synthesis Inhibitor Herbicide, a Microtubule Assembly Inhibitor Herbicide or a Photosystem Inhibitor Herbicide.
  5. 5. The method of any one of claims 1-4, wherein the herbicide is selected from the groups of: carbamates; thiocarbamates; haloacetanilides; substituted phenoxy-, naphthoxy- and phenoxyphenoxy carboxylic acid derivatives; heteroaryloxyphenoxyalkane carboxylic acid derivatives; quinolyloxy-, quinoxalyloxy-, pyridyloxy-, benzoxazolyloxy- and benzothiazolyloxyphenoxyalkane carboxylic acid esters; cyclohexanedione derivatives; imidazolinones; pyrimidinyloxypyridincarboxylic acid derivatives; pyrimidyloxybenzoic acid derivatives; sulfonylureas; triazolopyrimidinesulfonamide derivatives; S-(N-aryl-N- alkylcarbamoylmethyl)dithiophosphoric esters; hormone-type herbicides; pyridinecarboxylic acids; triazinones; triazolinones; pyridinecarboxamides; hydroxybenzonitriles; isoxazoles; phenoxyphenoxy- and heteroaryloxyphenoxy carboxylic acid esters and salts, sulfonylureas, imidazolinones; and isoxazoles.
  6. 6. The method of any one of claims 1-5, wherein said at least one herbicide is glyphosate. 64 409753-014WO (210650) BUSINESS.31627387.1
  7. 7. The method of any one of claims 1-5, wherein said at least one herbicide is glufosinate.
  8. 8. The method of any one of claims 1-7, wherein said at least one ascaroside comprises an ascaroside having the structure (I): OZ where: Z is an optionally substituted C3-40 aliphatic group, and each of R a and R b is independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20 aliphatic, C1-20 acyl, C1-20 heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C 2-20 carbonate (e.g. -a moiety -C(O)OR c ), a C 2-20 carbamate (e.g. -a moiety -C(O)N(R c ) 2 ), a C 2-20 thioester (e.g. a moiety -C(S)R c ), a C 2-20 thiocarbonate (e.g. a moiety -C(S)OR c ), a C2-20 dithiocarbonate (e.g. a moiety -C(S)SR c ), a C 1-20 thiocarbamate (e.g. a moiety -C(S)N(R c ) 2 ), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where R c is independently at each occurrence selected from -H, optionally substituted C1-12 aliphatic, optionally substituted C1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where R a and R b may be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.
  9. 9. The method of claim 8, wherein Z is selected from the group consisting of: i. –CH(CH3)–R 1 , where R 1 is an optionally substituted C1-40 aliphatic group ii. –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; iii. –CH(CH3)–(CH2)n–CH=CH-CO2R 2 , where n is an integer from 1 to 40, and R 2 is - H, a metal cation, an optionally substituted C 1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; 65 409753-014WO (210650) BUSINESS.31627387.1 iv. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; v. –CH(CH3)–(CH2)n–C(O)–CH2-CO2R 2 , where n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; 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 C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; 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 C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; viii. –(CH 2 ) n –CH(OH)–CH 2 -CO 2 R 2 , where n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and ix. –(CH 2 ) n –C(O)–CH 2 -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.
  10. 10. The method of claim 8, wherein Z is selected from the group consisting of: (x) –CH(CH 3 )–(CH 2 ) n –CON(R 3 ) 2 , where n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xi) –CH(CH 3 )–(CH 2 ) n –CH=CH-CON(R 3 ) 2 , where 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 C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; 66 409753-014WO (210650) BUSINESS.31627387.1 (xii) –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C1-20 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 linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiii) –CH(CH 3 )–(CH 2 ) n –C(O)–CH 2 -CON(R 3 ) 2 , where n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiv) –(CH 2 ) n –CON(R 3 ) 2 , where n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xv) –(CH2)n–CH=CH-CON(R 3 )2, where 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 C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvi) –(CH2)n–CH(OH)–CH2-CON(R 3 )2, where 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 linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; 67 409753-014WO (210650) BUSINESS.31627387.1 (xvii) –(CH2)n–C(O)–CH2-CON(R 3 )2, where n is an integer from 1 to 40, and each R 3 is independently -H, an optionally substituted C1-20 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 linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; or (xviii) an optionally unsaturated, optionally substituted C 2-40 sidechain terminating in a chain end comprising a nitrogen-, oxygen- or sulfur-containing functional group.
  11. 11. The method of any one of claims 1-10, wherein said at least one ascaroside comprises an ascaroside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24.
  12. 12. The method of any one of claims 1-11, wherein said at least one ascaroside comprises ascr#18.
  13. 13. The method of any one of claims 1-12, wherein said at least one ascaroside and said at least one herbicide are applied simultaneously.
  14. 14. The method of claim 13, wherein said at least one ascaroside and said at least one herbicide are combined together in a tank mix.
  15. 15. The method of any one of claims 1-12, wherein said at least one ascaroside and said at least one herbicide are applied sequentially.
  16. 16. The method of any one of claims 1-15, wherein said combination is used as a seed coating.
  17. 17. A composition comprising at least one ascaroside and at least one herbicide.
  18. 18. The composition of claim 17, wherein said at least one ascaroside and said at least one herbicide are present in effective amounts.
  19. 19. The composition of claim 18, wherein said effective amount reduces phytotoxic side effects on crop plants as compared to phytotoxic side effects on plants associated with application of the herbicide alone.
  20. 20. The composition of claim 17 or 18, wherein said effective amount reduces the phytotoxicity rating on crop plants as compared to the phytotoxicity rating on plants associated with application of the herbicide alone.

Description

ASCAROSIDES AND HERBICIDAL COMBINATIONS AND METHODS FOR USE CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application claims the benefit of priority to U.S. Provisional Appl. No. 63/511,172, filed June 29, 2023, the entirety of which is hereby incorporated by reference. FIELD OF THE INVENTION [0002] The invention is drawn to compositions and methods relating to use of an ascaroside and one or more herbicides. BACKGROUND OF THE INVENTION [0003] Herbicides are well known tao control undesired plants. Selective herbicides control specific plants and plant varieties, while non-selective herbicides kill most (if not all) plants that are contacted with the herbicide. A large percentage of herbicides are used for agricultural purposes to selectively remove unwanted plants from crop producing fields. [0004] Selective herbicides are used frequently in crop producing fields. The selective herbicides are used to remove unwanted plants from growing in the same field that the crop producing plants (“crops”) are being grown. While herbicides can be quite selective at reducing the unwanted plants in the field, herbicides can have phytotoxic side effects on the crop plants. SUMMARY OF THE INVENTION [0005] Combinations of agents for preventing, treating, or controlling unwanted plants and methods of their use are provided. The combinations comprise at least one ascaroside (or a derivative or analog of an ascaroside) with at least one herbicide. The ascaroside can be combined with at least one herbicide to lessen the phytotoxic effects of the herbicide on the treated crop while simultaneously killing unwanted plants in the applied area. The ascarosides and herbicides may be provided in the same composition or may be applied together (i.e., substantially simultaneously) or 1 409753-014WO (210650) BUSINESS.31627387.1 sequentially. The agents are applied in an effective amount, i.e., an amount sufficient to control or inhibit unwanted plant growth and also reduce phytotoxic side effects of the herbicides on crop plants. DETAILED DESCRIPTION OF THE INVENTION [0006] The disclosure provides compositions and methods relating to use of one or more ascarosides and one or more herbicides. In some embodiments, the disclosure provides compositions and methods relating to combinations of one or more ascarosides and one or more herbicides wherein the ascaroside(s) serve the purpose of a safener to lessen phytotoxic effects of the herbicide(s) on the treated crop. As used herein, the term “ascaroside” includes the ascaroside, a derivative, an analog of the ascaroside, or combinations thereof, as will be described in further detail herein. The ascaroside can be used with any herbicide. [0007] The ascaroside(s) and the herbicide(s) may be used in the same composition, or the ascaroside(s) and the herbicide(s) may be applied separately (e.g., in separate formulations), either simultaneously or sequentially. If applied sequentially, the applications are close enough in time such that they are able to work in combination to produce the beneficial results. [0008] As noted, methods and compositions of the invention comprise ascarosides. Ascarosides are secondary metabolites produced by nematodes. Many structurally diverse ascarosides have been identified in nature and are believed to function as an evolutionarily conserved chemical language used by nematodes to control many aspects of their development. [0009] Ascarosides are derivatives of the sugar ascarylose—a di-deoxy sugar lacking hydroxyl groups at its 3- and 6-positions. Ascarosides have the general structure shown in Formula I: OZ I), wherein: Z is an optionally substituted C2-40 aliphatic group, and 2 409753-014WO (210650) BUSINESS.31627387.1 each of Ra and Rb is independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20 aliphatic, C1-20 acyl, C1-20 heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group, a sulfur-linked functional group, a silicon-linked functional group, a C2-20 carbonate (e.g. -a moiety -C(O)ORc), a C2-20 carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20 thioester (e.g. a moiety -C(S)Rc), a C2-20 thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20 dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20 thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, where each Rc is independently at each occurrence selected from -H, optionally substituted C1-12 aliphatic, optionally substituted C1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Ra and Rb may be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturat