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CN-122003241-A - Ascaroside particle compositions and methods of use

CN122003241ACN 122003241 ACN122003241 ACN 122003241ACN-122003241-A

Abstract

A ascaroside particle composition is provided that can be used to form a ascaroside solution. In one embodiment, the ascaroside particle composition comprises one or more ascarosides and a particle carrier composition. The ascaroside particle composition may be dissolved in water and used to treat plants and crops.

Inventors

  • FARMER JAY

Assignees

  • 归因生物科技有限公司

Dates

Publication Date
20260508
Application Date
20240815
Priority Date
20230816

Claims (20)

  1. 1. A ascaroside composition comprising one or more ascarosides and a soluble solid carrier composition, wherein the ascaroside composition comprises about 20 wt% or less of the one or more ascarosides.
  2. 2. The composition of claim 1, wherein the ascaroside composition comprises from about 1% to about 20% by weight of the one or more ascarosides.
  3. 3. The composition of claim 1 or 2, wherein the one or more ascarosides comprises a ascaroside having structure (I): Wherein: Z is an optionally substituted C 3-40 aliphatic group, and Each of R a and R b is independently-H or an optionally substituted moiety selected from the group consisting of C 1-20 aliphatic, C 1-20 acyl, C 1-20 heteroaliphatic, aryl, heteroaryl, hydroxy protecting group, phosphorus-attached functional group, sulfur-attached functional group, silicon-attached functional group, C 2-20 carbonates (e.g., part-C (O) OR c ）、C 2-20 carbamates (e.g., part-C (O) N (R c ) 2 ）、C 2-20 thioesters (e.g., part-C (S) R c ）、C 2-20 thiocarbonates (e.g., part-C (S) OR c ）、C 2-20 dithiocarbonates (e.g., part-C (S) SR c ）、C 1-20 thiocarbamates (e.g., part-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, wherein R c is independently selected at each occurrence from the group consisting of-H, an optionally substituted C 1-12 aliphatic, an optionally substituted C 1-12 heteroaliphatic, a, an optionally substituted aryl group, an optionally substituted heteroaryl group, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and wherein R a and R b are capable of together forming an optionally substituted ring, optionally containing one or more heteroatoms and optionally containing one or more sites of unsaturation.
  4. 4. A composition according to claim 3, wherein Z is selected from the group consisting of: -CH (CH 3 )–R 1 , wherein R 1 is an optionally substituted C 1-40 aliphatic group -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; -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; -CH (CH 3 )–(CH 2 ) n –CH(OH)–CH 2 -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; -CH (CH 3 )–(CH 2 ) n –C(O)–CH 2 -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; - (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; - (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; - (CH 2 ) n –CH(OH)–CH 2 -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 - (CH 2 ) n –C(O)–CH 2 -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.
  5. 5. A composition according to claim 3, wherein Z is selected from the group consisting of: -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, an optionally substituted C 1-20 heteroaliphatic, an optionally substituted aromatic, an optionally substituted heteroaryl, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; -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, an optionally substituted C 1-20 heteroaliphatic, an optionally substituted aromatic, an optionally substituted heteroaryl, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; -CH (CH 3 )–(CH 2 ) n –CH(OH)–CH 2 -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, an optionally substituted C 1-20 heteroaliphatic, an optionally substituted aromatic, an optionally substituted heteroaryl, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; -CH (CH 3 )–(CH 2 ) n –C(O)–CH 2 -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, an optionally substituted C 1-20 heteroaliphatic, an optionally substituted aromatic, an optionally substituted heteroaryl, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; - (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, an optionally substituted C 1-20 heteroaliphatic, an optionally substituted aromatic, an optionally substituted heteroaryl, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaroside molecule via a bond or 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, an optionally substituted C 1-20 heteroaliphatic, an optionally substituted aromatic, an optionally substituted heteroaryl, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; - (CH 2 ) n –CH(OH)–CH 2 -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, an optionally substituted C 1-20 heteroaliphatic, an optionally substituted aromatic, an optionally substituted heteroaryl, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; - (CH 2 ) n –C(O)–CH 2 -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, an optionally substituted C 1-20 heteroaliphatic, an optionally substituted aromatic, an optionally substituted heteroaryl, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety, or Optionally unsaturated optionally substituted C 2-40 side chain terminating at the chain end comprising a nitrogen, oxygen or sulfur containing functional group.
  6. 6. The composition of any one of claims 1 to 5, wherein the one or more ascarosides comprise ascarosides selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24.
  7. 7. The composition of any one of claims 1 to 6, wherein the one or more ascarosides comprises ascr#18.
  8. 8. The composition of any one of claims 1 to 7, wherein at least one ascaroside is a ascaroside salt.
  9. 9. The composition of any one of claims 1 to 8, wherein the soluble solid carrier composition comprises a water-soluble filler.
  10. 10. The composition of claims 1-9, wherein the soluble solid carrier composition comprises one or more pH adjusting agents.
  11. 11. The composition of claim 10, wherein the pH adjuster increases the pH of the aqueous solution when dissolved in water.
  12. 12. The composition of claim 11, wherein the pH adjustor is selected from the group consisting of ammonium carbonate, ammonium hydrogen phosphate, ammonium sulfite, ammonium phosphate, barium hydroxide, barium carbonate, calcium hydrogen carbonate, calcium hydroxide, calcium phosphate, potassium carbonate, potassium hydrogen phosphate, potassium sulfite, potassium phosphate, aluminum potassium sulfate, potassium hydrogen carbonate (potassium bicarbonate), potassium nitrite, potassium hydroxide, lithium carbonate, lithium hydrogen carbonate, magnesium hydroxide, magnesium carbonate, magnesium hydrogen phosphate, sodium borate (borax), sodium carbonate (soda ash), disodium hydrogen phosphate, trisodium phosphate, sodium bicarbonate (sodium bicarbonate), sodium hydroxide, ammonium hydrogen carbonate, zinc hydroxide, and zinc carbonate.
  13. 13. The composition of any one of claims 1 to 11, wherein the ascaroside composition comprises one or more ascarosides and one or more carbonates (e.g., sodium bicarbonate or potassium bicarbonate).
  14. 14. The composition of any one of claims 1 to 13, wherein the ascaroside composition consists essentially of one or more ascarosides and one or more carbonates (e.g., sodium bicarbonate or potassium bicarbonate).
  15. 15. The composition of any one of claims 1 to 14, wherein the composition is characterized in that the one or more ascarosides exhibit a solubility in water of at least 1,3, 6, 9, 12, 15, 20, or 25 g/gallon.
  16. 16. The composition of any one of claims 1 to 14, wherein the composition is characterized in that the one or more ascarosides exhibit a solubility in water of at least 0.1, 1, 10, 50 or 100 mM.
  17. 17. The composition of any one of claims 1 to 14, wherein the composition is characterized in that the one or more ascarosides exhibit a solubility in water of at least 50%, 75%, 100%, 1,000%, 5,000%, or 10,000% greater than a reference.
  18. 18. The composition of claim 17, wherein the reference is a corresponding composition containing only the one or more ascarosides.
  19. 19. A method of treating a crop or plant with one or more ascarosides, the method comprising: obtaining a ascaroside composition according to any one of claims 1 to 18, Mixing the ascaroside composition with water to form a ascaroside solution, and Applying the ascaroside solution to the crop or plant.
  20. 20. The method of claim 19, wherein the ascaroside composition is mixed with about 2L to about 10L of water.

Description

Ascaroside particle compositions and methods of use Cross Reference to Related Applications The present application claims the benefit of priority from U.S. provisional application No. 63/519,978 filed 8/16/2023, the entire contents of which are hereby incorporated by reference. Technical Field The present invention relates to solid ascaroside compositions and methods relating to the use of solid ascaroside compositions. Background Ascaroside natural products are secondary metabolites produced by nematodes. A large number of structurally diverse ascarosides have been identified in nature and these molecules are thought to act as evolutionarily conserved chemical languages by which nematodes control many aspects of their development. Ascarosides are also perceived by other organisms and have been shown to have a range of effects on many organisms including bacteria, fungi, plants and mammals (including humans). Ascarosides have potential as human pharmaceuticals, agrochemicals, and products for other diverse and valuable applications. It has been demonstrated that ascaroside treatment, when applied to plants, exhibits efficacy in increasing the resistance of plants to certain pathogens and/or in inducing and eliciting plant defense responses that may inhibit pathogen growth and/or infestation. Ascarosides can thus prevent the proliferation of pathogens and/or protect crops from damaging effects caused by various pathogens by activating and/or eliciting the plant's innate defenses. A unique feature of ascarosides is their high potency. Plants respond to very low concentrations of ascarosides and therefore the effective application amount required to elicit plant defenses may be very low. This in turn presents challenges to grower convenience and supply chain logistics. The present invention provides a solution to these challenges and related problems. Disclosure of Invention The present inventors have found that the concentration of ascaroside in foliar sprays required to elicit or induce a plant defensive response can be as low as 10 nanomoles per liter. This may correspond to a low single ppb level concentration of ascaroside in the foliar spray applied. In addition, the inventors have found that application of too high a concentration of ascaroside to the foliage of a crop may lead to a loss of its beneficial effects. Thus, a practical and accurate method of applying these products at low concentrations is highly desirable. The use of pure ascaroside to achieve a suitably low dosage requires that very small amounts (in some cases only a few milligrams) of ascaroside be dissolved into a tank containing hundreds of liters of water. This type of measurement and mixing is impractical for growers because they typically lack the equipment required to accurately measure and process such small quantities. Furthermore, ensuring that a small amount of solid ascaroside is completely homogeneously dissolved into a large amount of water can be difficult—ascaroside in pure form is solid and may be in the form of a fine powder. Such powdered ascarosides may not dissolve immediately upon addition to water and also have a tendency to float on the water surface and/or adhere to the edges of the container. These factors may lead to incomplete dissolution and/or inconsistent application rates. One solution to this problem is to use a pre-formulated ascaroside liquid concentrate that can be conveniently measured and mixed into an agricultural spray can. Many agrochemicals are provided as liquid concentrates and are typically formulated such that a grower uses between about 1 ⁄ and about 16 fluid ounces of concentrate per acre of crop treated (most typically about 1 to about 4 ounces per acre). Prior to field application, an appropriate volume of concentrate for the planting area to be treated is diluted into an appropriate volume of water (typically in a large spray tank) to produce a spray solution that is applied to the crop at a rate that ensures good leaf coverage (typically about 10-20 gallons per acre for row crops). The inventors have determined that certain ascaroside foliar spray treatments are surprisingly effective when applied to field crops by foliar spray at very low application rates (5 mg to 100mg per acre), and have developed prototype liquid concentrate formulations of ascaroside that can be conveniently applied by growers using familiar methods to achieve these application rates. Such formulations are convenient to use and perform well, but unfortunately are quite inefficient from a logistical point of view. For example, prototype ascaroside concentrates have been produced to enable ascarosides to be conveniently administered at a rate of between about 25-100 mg/acre. The prototype was designed such that a2 fluid ounce per acre application would deliver 25mg ascaroside per acre. Although the formulation is technically a concentrate, the solution is still very dilute compared to typical agrochemicals and cont