Methods for treating seeds and plants to reduce foodborne illnesses

Abstract

The present application relates to a method for inhibiting the growth of human pathogenic bacteria in or on a plant by treating the seeds of the plant with an aqueous solution comprising one or more ascarosides. The present application also provides a method for inhibiting the growth of human pathogenic bacteria in or on a plant by spraying the plant with an aqueous solution comprising one or more ascarosides.

Description

[Technical field]

[0001] Claiming priority This application claims priority to U.S. Provisional Patent Application No. 63 / 291,334, entitled "Methods of Seed and Plant Treatment to Reduce Foodborne Illness," filed on December 17, 2021, and U.S. Provisional Patent Application No. 63 / 306,827, entitled "Methods of Seed and Plant Treatment to Reduce Foodborne Illness," filed on February 4, 2022, the contents of both of which are incorporated herein by reference.

[0002] Federally Sponsored Research or Development This invention was made with Government support under STTR Grant 1R41AI152915-01 awarded by the National Institutes of Health (NIH). The Government has certain rights in this invention. [Background technology]

[0003] This application relates generally to methods for reducing foodborne illnesses. More specifically, the present invention provides methods for treating seeds or plants to prevent pathogen contamination of edible products derived from such seeds or plants.

[0004] Edible sprouts are an increasingly popular food crop due to their year-round production and availability, short growing season, and nutritional benefits, including high levels of vitamins and minerals. However, sprouts are also a high-risk food with respect to frequency of pathogen contamination, and the increase in sprout consumption has been accompanied by a corresponding increase in sprout-associated foodborne illness outbreaks. According to the US Centers for Disease Control (CDC) National Outbreak Reporting System, from 1996 to 2017, the United States experienced 58 sprout-associated foodborne illness outbreaks (31 of which were multistate), including at least 1,953 illnesses, 212 hospitalizations, and 5 deaths.

[0005] Seeds are the primary source of sprout contamination. Seed production, handling, processing and / or distribution involve multiple stages of exposure to potential pathogens during which pathogens can enter the seed through cracks, crevices or intercellular spaces in the seed, where they can persist for weeks to years. This renders common practices to minimize pathogen contamination, such as application of antimicrobial compounds to irrigation water, ineffective. Sprout production requires warm, moist conditions that serve to further amplify the growth of any contaminating bacterial pathogens. Thus, even low bacterial levels in the seed can result in high microbial loads by the end of the sprout production process. In most cases, there are no visible symptoms that the sprouts are contaminated with pathogens. Furthermore, biofilms of non-pathogenic and pathogenic bacteria can form on the exterior or interior of the sprouts, providing a protected environment in which pathogens can colonize and multiply. Thus, pathogen contamination of sprouts is not easily addressed. Moreover, antimicrobial treatments are unattractive to growers and the sprout industry because they can adversely affect germination rates and yields of sprouts. These problems may also affect plants grown from contaminated seeds.

[0006] The FDA has made many investments to reduce food safety issues related to edible sprouts. In 2019, the FDA issued a draft guidance with specific recommendations to help reduce food safety issues, "Reducing Microbial Food Safety Hazards in the Production of Seed for Sprouting." It states that seeds for germination are "food" and should be treated as such whenever possible. Unfortunately, seed growers do not always know if the seeds they produce will be used in the production of sprouts. Thus, seeds may be exposed to manure or other sources of contamination (rodents, birds) during production, which, while having little or no impact on the mature field crops grown from these seeds, poses a serious threat to sanitary sprout production.

[0007] According to the FDA, no single treatment has been shown to eliminate human pathogens on seeds or sprouts, and those that can significantly reduce sprout contamination have a detrimental effect on germination and growth. Therefore, all preventative measures should be taken to prevent high levels of bacterial contamination, including all steps involved in seed to sprout production. The FDA recommends that seeds used for edible germination should be treated with one or more treatments to reduce levels of Salmonella and E. coli O157 by at least 5 logs. Achieving this level of reduction is a very challenging task. Extensive washing and chlorination have proven ineffective in disinfecting sprout seeds, because microorganisms can reside in protected depressions on the seed surface or under the seed coat. Researchers have tried various approaches to improve the microbial safety of sprouts, such as treatment with electrolyzed water, organic acids, calcium hypochlorite, or sodium hypochlorite (bleach), but none of these treatments are sufficiently effective to remove human pathogens from sprouts. Furthermore, calcium hypochlorite and sodium hypochlorite are toxic via ingestion and skin contact, and these solutions can release toxic gases, potentially endangering workers. To make matters worse, these chemicals are strong oxidizing and halogenating agents that can reduce the nutritional value of the sprouts and can contaminate the sprouts with residual chlorinated organic molecules formed during processing. It would be beneficial to provide a safer and more effective method for ensuring the safety of sprouts as a food source. Summary of the Invention [Means for solving the problem]

[0008] Compositions and methods are provided for inhibiting pathogen growth in seeds, plants or plant parts. The compositions comprise at least one ascaroside. In some embodiments, the compositions comprise two or more ascarosides and an additional component to enhance pathogen inhibition. In one embodiment, the additional component comprises salicylic acid. The methods of the invention include soaking, spraying, coating, or contacting plant seeds and / or sprouts to prevent or inhibit pathogen growth within the growing plant.

[0009] In one embodiment, the one or more ascarosides have the formula A: [ka] In accordance with the formula: (i) -CH(CH 3 )-R 1 where R 1 is an optionally substituted C 1-40 is an aliphatic group; (ii) -CH(CH 3 )-(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; (iii) -CH(CH 3 )-(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; (iv) -CH(CH 3 )-(CH 2 ) n-CH(OH)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; (v)-(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; (vi)-(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; or (vii)-(CH 2 ) n -CH(OH)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0010] In certain embodiments, for ascarosides of formula A, Z is -CH(CH 3 )-(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide. A specific example of this type of ascaroside is ascr#18 shown below. [ka]

[0011] In certain embodiments, the one or more ascarosides have the formula (A), where Z is -CH(CH 3 )-(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide. A specific example of this type of ascaroside is ascr#7 shown below. [ka]

[0012] In one embodiment, the step of treating the plant seeds with an aqueous solution comprising one or more ascarosides comprises soaking the seeds in the aqueous solution. In one embodiment, the seeds are soaked in the aqueous solution for about 1 minute to about 6 hours. The concentration of the one or more ascarosides in the aqueous solution may be from about 0.001 mM to about 10.0 mM. In one embodiment, the seeds are soaked in the aqueous solution for a time sufficient to bring the seeds out of quiescence.

[0013] In a further aspect, a method for enhancing plant growth is provided. In certain embodiments, the method comprises treating the seeds of the plant with an aqueous solution comprising one or more ascarosides, and the plants grown from the treated seeds exhibit accelerated growth compared to plants grown from untreated seeds. The one or more ascarosides can have a structure as described in other embodiments provided above.

[0014] In a further aspect, a method for producing edible sprouts is provided. In a particular embodiment, the method comprises providing seeds from a plant that can be used to produce edible sprouts, treating the seeds by soaking them in an aqueous solution containing one or more ascarosides, placing the seeds in a suitable container for forming sprouts from the treated seeds, and harvesting the sprouts after they reach a desired size. Again, the one or more ascarosides can have a structure as described in other embodiments hereinbefore.

[0015] The present invention includes, but is not limited to, the following embodiments.

[0016] Embodiment 1: A method of inhibiting the growth of a human enteric pathogen in a plant, the method comprising treating seeds of the plant with a composition comprising one or more ascarosides.

[0017] Embodiment 2: The one or more ascarosides has structure (I): [ka] wherein Z is an optionally substituted C 3-40 is an aliphatic group, R a and R b Each of is independently -H or -C 1-20 aliphatic, C 1-20 Achill, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxy protecting group, phosphorus-bridged functional group, sulfur-bridged functional group, silicon-bridged functional group, C 2-20 Carbonates (e.g., -C(O)OR c part), C 2-20 Carbamates (e.g., -C(O)N(R c ) 2 part), C 2-20 Thioesters (e.g., -C(S)R c part), C 2-20 Thiocarbonates (e.g., -C(S)OR c part), C 2-20Dithiocarbonates (e.g., -C(S)SR c part), C 1-20 Thiocarbamates (e.g., -C(S)N(R c ) 2 a linker moiety, a sugar moiety, a peptide, a polymer chain, or to another ascaroside molecule via a bond or a carbon-containing linker moiety; R c represents independently at each occurrence -H, optionally substituted C 1-12 Aliphatic, optionally substituted C 1-12 is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; R a and R b may be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, optionally containing one or more sites of unsaturation.

[0018] Embodiment 3: Z is -CH(CH 3 )-R 1 where R 1 is an optionally substituted C 1-40 Aliphatic group; -CH(CH 3 )-(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; 3 )-(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; 3 )-(CH 2 ) n -CH(OH)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; 3 )-(CH 2 ) n -C(O)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; -(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; -(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; -(CH2) n -CH(OH)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; and -(CH 2 ) n -C(O)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 3. The method of embodiment 2, wherein the aryl group is selected from the group consisting of: an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0019] Embodiment 4: R a and R b The method of embodiment 2 or 3, wherein each of

[0020] Embodiment 5: Z is -CH(CH 3 ) n -(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 The method according to any one of embodiments 2 to 4, wherein the aryl group is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0021] Embodiment 6: The method of embodiment 1, wherein at least one of the one or more ascarosides is ascr#18.

[0022] Embodiment 7: Z is -CH(CH 3 )-(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20The method according to any one of embodiments 2 to 4, wherein the aryl group is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0023] Embodiment 8: The method of embodiment 1, wherein at least one of the one or more ascarosides is ascr#7.

[0024] Embodiment 9: The method of any one of embodiments 1 to 8, wherein treating the seeds of the plant comprises soaking the seeds in an aqueous solution comprising one or more ascarosides.

[0025] Embodiment 10: The method of embodiment 9, wherein the seeds are soaked in the aqueous solution for about 1 minute to about 6 hours.

[0026] Embodiment 11: The method of embodiment 9, wherein the concentration of the one or more ascarosides in the aqueous solution is from about 0.001 mM to about 1.0 mM.

[0027] Embodiment 12: The method according to any one of claims 1 to 11, wherein the seed of the plant is a seed of a plant that can be used to produce edible sprouts.

[0028] Embodiment 13: The method of embodiment 12, wherein the seed of the plant is a seed that can be used to produce edible legume sprouts.

[0029] Embodiment 14: The method of embodiment 12, wherein the seed of the plant is a seed that can be used to produce edible cereal sprouts.

[0030] Embodiment 15: The method of embodiment 12, wherein said seed of said plant is a seed that can be used to produce edible oilseed sprouts.

[0031] Embodiment 16: The method of embodiment 12, wherein the seed of the plant is a seed that can be used to produce edible cabbage sprouts.

[0032] Embodiment 17: The method of embodiment 12, wherein the seeds of the plant are seeds that can be used to produce edible parsley sprouts.

[0033] Embodiment 18: The method of embodiment 12, wherein the seed of the plant is a seed that can be used to produce edible onion sprouts.

[0034] Embodiment 19: The method of embodiment 12, wherein the seed of the plant is a seed that can be used to produce edible vegetable or herb sprouts.

[0035] Embodiment 20: The method of embodiment 12, wherein the seed of the plant is a seed that produces a crop.

[0036] Embodiment 21: The method according to any of embodiments 9 to 20, wherein the seeds are soaked in the aqueous solution for a time sufficient to gain about 2% to about 20% by weight of their dry weight.

[0037] Embodiment 22: The method of any of embodiments 9 to 21, wherein the seeds are soaked in the aqueous solution for a time sufficient to bring the seeds out of quiescence.

[0038] Embodiment 23: A method of inhibiting the growth of a human enteric pathogen in or on a plant, comprising spraying the plant with a composition comprising one or more ascarosides.

[0039] Embodiment 24: The one or more ascarosides has structure (I): [ka] wherein Z is an optionally substituted C 3-40 is an aliphatic group, R a and R b Each of is independently -H or -C 1-20 aliphatic, C 1-20 Achill, C 1-20Heteroaliphatic, aryl, heteroaryl, hydroxy protecting group, phosphorus-bridged functional group, sulfur-bridged functional group, silicon-bridged functional group, C 2-20 Carbonates (e.g., -C(O)OR c part), C 2-20 Carbamates (e.g., -C(O)N(R c ) 2 part), C 2-20 Thioesters (e.g., -C(S)R c part), C 2-20 Thiocarbonates (e.g., -C(S)OR c part), C 2-20 Dithiocarbonates (e.g., -C(S)SR c part), C 1-20 Thiocarbamates (e.g., -C(S)N(R c ) 2 a linker moiety, a sugar moiety, a peptide, a polymer chain, or to another ascaroside molecule via a bond or a carbon-containing linker moiety; R c represents independently at each occurrence -H, optionally substituted C 1-12 Aliphatic, optionally substituted C 1-12 is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; R a and R b may be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, optionally containing one or more sites of unsaturation.

[0040] Embodiment 25:R a and R b and R are both -H.

[0041] Embodiment 26: Z is -CH(CH 3 )-R 1 where R 1 is an optionally substituted C 1-40Aliphatic group; -CH(CH 3 )-(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; 3 )-(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; 3 )-(CH 2 ) n -CH(OH)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; 3 )-(CH 2 ) n -C(O)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; -(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; -(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; -(CH 2 ) n -CH(OH)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide; and -(CH 2 ) n -C(O)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 26. The method of embodiment 24 or 25, wherein the aryl group is selected from the group consisting of: an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0042] Embodiment 27: Z is -CH(CH 3 )-(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 26. The method of embodiment 24 or 25, wherein the amino acid is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0043] Embodiment 28: The method of embodiment 23, wherein at least one of the one or more ascarosides is ascr#18.

[0044] Embodiment 29: Z is -CH(CH 3 )-(CH 2 ) n -CH=CH-CO 2 R 3 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 26. The method of embodiment 24 or 25, wherein the amino acid is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0045] Embodiment 30: The method of embodiment 23, wherein at least one of the one or more ascarosides is ascr#7.

[0046] Embodiment 31: The method of any one of embodiments 23 to 30, wherein the concentration of the one or more ascarosides in the composition is from about 1 ppb to about 50 ppm.

[0047] Embodiment 32: The method of any one of embodiments 23 to 31, wherein the plant is an edible sprout plant.

[0048] Embodiment 33: The method of embodiment 32, wherein the edible sprout plant is an edible legume sprout plant.

[0049] Embodiment 34: The method of embodiment 32, wherein the edible sprout plant is an edible cereal sprout plant.

[0050] Embodiment 35: The method of embodiment 32, wherein the edible sprout plant is an edible oilseed sprout plant.

[0051] Embodiment 36: The method of embodiment 32, wherein the edible sprout plant is an edible cabbage sprout plant.

[0052] Embodiment 37: The method of embodiment 32, wherein the edible sprout plant is an edible parsley sprout plant.

[0053] Embodiment 38: The method of embodiment 32, wherein the edible sprout plant is an edible onion sprout plant.

[0054] Embodiment 39: The method of embodiment 32, wherein the edible sprout plant is an edible vegetable or herb sprout plant.

[0055] Embodiment 40: The method of any one of embodiments 23 to 31, wherein the plant is a crop plant.

[0056] Embodiment 41: A method of producing edible sprouts comprising treating seeds from a plant that can be used to produce edible sprouts by soaking the seeds in an aqueous solution comprising one or more ascarosides, placing the treated seeds in a suitable container in which sprouts can be formed from the treated seeds, and harvesting the sprouts after they reach a desired size.

[0057] These and other features, aspects and advantages of the present disclosure will become apparent upon reading the following detailed description in conjunction with the accompanying drawings, which are briefly described below. The present invention includes any combination of two, three, four or more of the above-described embodiments, as well as any combination of two, three, four or more of the features or elements described in the present disclosure, regardless of whether such features or elements are explicitly combined in a particular embodiment herein. The present disclosure is intended to be read in its entirety such that it should be considered as intended that any separable features or elements of the disclosed invention can be combined in any of its various aspects and embodiments, unless the context clearly indicates otherwise. Other aspects and advantages of the present disclosure will become apparent from the following.

[0058] definition In order that this disclosure may be more readily understood, certain terms are first defined below. Further definitions of these terms, as well as other terms, are set forth throughout the specification.

[0059] In this application, unless otherwise clear from the context, the term "a" may be understood to mean "at least one." As used in this application, the term "or" may be understood to mean "and / or." As used in this application, the terms "comprising" and "including" may be understood to encompass the itemized recited components or steps, whether presented by themselves alone or together with one or more additional components or steps. As used in this application, the term "comprise," as well as variations of this term, such as "comprising" and "comprises," are not intended to exclude other additives, components, integers, or steps.

[0060] As used herein, the terms "about" and "approximately" are used as equivalents. Unless otherwise stated, the terms "about" and "approximately" can be understood to allow for standard variations that would be understood by one of ordinary skill in the art. When a range is provided herein, the endpoints are included. Any numbers used in this application with or without about / approximately are meant to encompass any typical variations that would be understood by a person of ordinary skill in the relevant art. In some embodiments, the term "about" or "approximately" refers to a range of values ​​that is included within 25%, 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1% or less in either direction (above or below) of the stated reference value, unless otherwise stated or otherwise evident from the context (except where such numbers may exceed 100% of the possible values).

[0061] Definitions of certain functional groups and chemical terms are described in more detail below. For purposes of this invention, chemical elements are defined as defined in the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75 th Ed., and specific functional groups are generally defined as described therein. Further, 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, the entire contents of each of which are incorporated herein by reference.

[0062] Certain compounds provided herein may contain one or more asymmetric centers and therefore may exist in various stereoisomeric forms, such as enantiomers and / or diastereomers.Thus, the compounds of the present invention and their compositions may be in the form of individual enantiomers, diastereomers or geometric isomers, or may be in the form of a mixture of stereoisomers.In certain embodiments, the compounds of the present invention are enantiopure compounds.In certain other embodiments, mixtures of enantiomers or diastereomers are provided.

[0063] Additionally, certain compounds described herein may have one or more double bonds that can exist as Z or E isomers, unless otherwise indicated. The compounds of the present invention can be provided as individual isomers substantially free of other isomers, or as mixtures of various isomers, e.g., racemic mixtures of enantiomers.

[0064] As used herein, the term "isomer" includes all geometric and stereoisomers. For example, "isomer" includes cis and trans isomers, E and Z isomers, R and S enantiomers, diastereomers, (D) isomers, (L) isomers, racemic mixtures thereof, and other mixtures thereof, as being within the scope of the present invention. For example, in some embodiments, a compound may be provided that is substantially free of one or more corresponding stereoisomers, and may be referred to as "stereochemically enriched."

[0065] In some embodiments, when a particular enantiomer is preferred, the enantiomer may be provided substantially free of the opposite enantiomer and may be referred to as "optically enriched". As used herein, "optically enriched" means that the compound of the present invention is made up of a significantly higher proportion of one enantiomer. In certain embodiments, the compound is made up of at least about 90% by weight of one enantiomer. In some embodiments, the compound is made up of at least about 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8% or 99.9% by weight of one enantiomer. In some embodiments, the enantiomeric excess of the provided compound is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8% or 99.9%. In some embodiments, enantiomers can be separated from racemic mixtures by any known method, such as chiral high performance liquid chromatography (HPLC) and the formation and crystallization of chiral salts, or can be prepared by asymmetric synthesis.See, for example, Jacques, et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981); Wilen, SH, et al., Tetrahedron 33:2725 (1977); Eliel, ELStereochemistry of Carbon Compounds (McGraw-Hill, NY, 1962); Wilen, SHTables of Resolving Agents and Optical Resolutions p.268 (EL Eliel, Ed., Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0066] The terms "halo" and "halogen," as used herein, refer to an atom selected from fluorine (fluoro, -F), chlorine (chloro, -Cl), bromine (bromo, -Br), and iodine (iodo, -I).

[0067] The terms "aliphatic" or "aliphatic group," as used herein, refer to a hydrocarbon moiety that may be straight-chained (i.e., unbranched), branched, or cyclic (including fused, bridged, and spiro-fused polycyclic), and may be fully saturated or contain one or more units of unsaturation, but is not aromatic. Unless otherwise specified, an aliphatic group contains 1-30 carbon atoms. In certain embodiments, an aliphatic group contains 1-12 carbon atoms. In certain embodiments, an aliphatic group contains 1-8 carbon atoms. In certain embodiments, an aliphatic group contains 1-6 carbon atoms. In some embodiments, an aliphatic group contains 1-5 carbon atoms, in some embodiments, an aliphatic group contains 1-4 carbon atoms, in still other embodiments, an aliphatic group contains 1-3 carbon atoms, and in still other embodiments, an aliphatic group contains 1-2 carbon atoms. Suitable aliphatic groups include, but are not limited to, linear or branched alkyl, alkenyl, and alkynyl, as well as hybrids thereof, such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl.

[0068] The terms "heteroaliphatic" or "heteroaliphatic group," as used herein, refer to an aliphatic group in which one or more carbon or hydrogen atoms are replaced by a heteroatom (e.g., oxygen, nitrogen, sulfur, phosphorus, boron, etc.).

[0069] The term "unsaturated," as used herein, means that a moiety has one or more double or triple bonds.

[0070] The term "alkyl," as used herein, refers to a saturated, straight or branched chain hydrocarbon group obtained by removing one hydrogen atom from an aliphatic moiety containing 1-6 carbon atoms. Unless otherwise specified, an alkyl group contains 1-12 carbon atoms. In certain embodiments, an alkyl group contains 1-8 carbon atoms. In certain embodiments, an alkyl group contains 1-6 carbon atoms. In some embodiments, an alkyl group contains 1-5 carbon atoms, in some embodiments, an alkyl group contains 1-4 carbon atoms, in still other embodiments, an alkyl group contains 1-3 carbon atoms, and in still other embodiments, an alkyl group contains 1-2 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, sec-pentyl, isopentyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, n-undecyl, dodecyl, and the like.

[0071] The term "alkenyl" as used herein means a monovalent group obtained by removing one hydrogen atom from a straight or branched chain aliphatic moiety having at least one carbon-carbon double bond. Unless otherwise specified, an alkenyl group contains 2-12 carbon atoms. In certain embodiments, an alkenyl group contains 2-8 carbon atoms. In certain embodiments, an alkenyl group contains 2-6 carbon atoms. In some embodiments, an alkenyl group contains 2-5 carbon atoms, in some embodiments, an alkenyl group contains 2-4 carbon atoms, in still other embodiments, an alkenyl group contains 2-3 carbon atoms, and in still other embodiments, an alkenyl group contains 2 carbon atoms. Alkenyl groups include, for example, ethenyl, propenyl, butenyl, 1-methyl-2-buten-1-yl, and the like.

[0072] The term "aryl" used alone or as part of a larger moiety, such as in "aralkyl", "aralkoxy" or "aryloxyalkyl", refers to monocyclic and polycyclic ring systems having a total of 5 to 20 ring members, in which at least one ring of the system is aromatic, and in which each ring of the system contains 3 to 12 ring members. The term "aryl" may be used interchangeably with the term "aryl ring". In certain embodiments of the invention, "aryl" refers to aromatic ring systems, including but not limited to phenyl, biphenyl, naphthyl, anthracyl, and the like, which may bear one or more substituents. Also included within the scope of the term "aryl" as used herein are groups in which the aromatic ring is fused to one or more additional rings, such as benzofuranyl, indanyl, phthalimidyl, naphthoimidyl, phenanthridinyl, or tetrahydronaphthyl.

[0073] As described herein, the compounds of the present invention may contain "optionally substituted" moieties. In general, the term "substituted", whether preceded by the term "optionally" or not, means that one or more hydrogens of the specified moiety may be replaced with a suitable substituent. Unless otherwise specified, an "optionally substituted" group may have a suitable substituent at each substitutable position of the group, and when more than one position in any given structure may be substituted with more than one substituent selected from a specified group, the substituents may be the same or different at each and every position. The combinations of substituents envisioned are preferably those that result in the formation of stable or chemically feasible compounds. As used herein, the term "stable" refers to a compound that is substantially unchanged when subjected to conditions that allow for production, detection, and, in certain embodiments, recovery, purification, and use for one or more of the purposes disclosed herein.

[0074] Suitable monovalent substituents on a substitutable carbon atom of an "optionally substituted" group are independently halogen; -(CH 2 ) 0-4 R o ;-(CH 2) 0-4 OR o ;-O-(CH 2 ) 0-4 C(O)OR o ;-(CH 2 ) 0-4 CH(OR o ) 2 ;-(CH 2 ) 0-4 S.R. o ;-(CH 2 ) 0-4 Ph, which is R o may be substituted with; R o may be substituted with -(CH 2 ) 0-4 O(CH 2 ) 0-1 Ph;-CH=CHPh, which is R o may be substituted with; -NO 2 ;-CN;-N 3 ;-(CH 2 ) 0-4 N(R o ) 2 ;-(CH 2 ) 0-4 N(R o )C(O)R o ;-N(R o )C(S)R o ;-(CH 2 ) 0-4 N(R o )C(O)NR o 2 ;-N(R o )C(S)NR o 2 ;-(CH 2 ) 0-4 N(R o )C(O)OR o ;-N(R o )N(R°)C(O)R o ;-N(R°)N(R°)C(O)NR o 2 ;-N(R o )N(R o )C(O)OR o ;-(CH 2 ) 0-4 C(O)R°;-C(S)R°;-(CH 2 ) 0-4C(O)OR o ;-(CH 2 ) 0-4 C(O)N(R o ) 2 ;-(CH 2 ) 0-4 C(O)SR o ;-(CH 2 ) 0-4 C(O)OSiR o 3 ;-(CH 2 ) 0-4 OC(O)R o ;-OC(O)(CH 2 ) 0-4 SR-SC(S)SR o ;-(CH 2 ) 0-4 SC(O)R o ;-(CH 2 ) 0-4 C(O)NR o 2 ;-C(S)NR o 2 ;-C(S)SR o ;-SC(S)SR o 、-(CH 2 ) 0-4 OC(O)NR o 2 ;-C(O)N(OR o )R o ;-C(O)C(O)R o ;-C(O)CH 2 C(O)R o ;-C(NOR o )R o ;-(CH 2 ) 0-4 SSR o ;-(CH 2 ) 0-4 S(O) 2 R o ;-(CH 2 ) 0-4 S(O) 2 OR o ;-(CH 2 ) 0-4 OS(O) 2 R o ;-S(O) 2 NR o 2 ;-(CH2 ) 0-4 S(O)R o ;-N(R o )S(O) 2 NR o 2 ;-N(R o )S(O) 2 R o ;-N(OR o )R o ;-C(NH)NR o 2 ;-P(O) 2 R o ;-P(O)R o 2 ;-OP(O)R o 2 ;-OP(O)(OR o ) 2 ;SiR o 3 ;-(C 1-4 Linear or branched alkylene)ON(R o ) 2 ; or -(C 1-4 Linear or branched alkylene)C(O)ON(R o ) 2 And each R o are optionally substituted as defined below and independently represent hydrogen, C 1-8 Aliphatic, -CH 2 Ph, -O(CH 2 ) 0-1 Ph, or a 5-6 membered saturated ring, partially unsaturated ring, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; or, notwithstanding the above definition, two independently occurring R o together with their intervening atom(s) form a 3-12 membered saturated, partially unsaturated, or aryl monocyclic or polycyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, which may be optionally substituted as defined below.

[0075] R o (or two independently occurring R oPreferred monovalent substituents on the ring (formed by any of the atoms intervening therein) are independently halogen, -(CH 2 ) 0-2 R ● , -(Halo R ● ), -(CH 2 ) 0-2 OH, -(CH 2 ) 0-2 OR ● , -(CH 2 ) 0-2 CH(OR ● ) 2 ;-O(Halo R ● ), -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 o ) 2 ;-(CH 2 ) 0-2 S.R. ● , -(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 ● And each R ● is unsubstituted or, if preceded by "halo", is substituted only by one or more halogens, C 1-4 Aliphatic, -CH2 Ph, -O(CH 2 ) 0-1 R is independently selected from Ph, or a 5-6 membered saturated ring, a partially unsaturated ring, or an aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. o Suitable divalent substituents on a saturated carbon atom of include ═O and ═S.

[0076] Suitable divalent substituents on a saturated carbon atom of an "optionally substituted" group include the following: =O, =S, =NNR * 2 , =NNHC(O)R * , =NNHC(O)OR * , =NNHS(O) 2 R * , =NR * , =NOR * , -O(C(R * 2 )) 2-3 O- or -S(C(R * 2 )) 2-3 S- is listed, and each R * is hydrogen, optionally substituted as defined below, 1-6 An aliphatic or unsubstituted 5-6 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. A preferred divalent substituent attached to a vicinal substitutable carbon of an "optionally substituted" group is -O(CR * 2 ) 2-3 O-, and each independently occurring R * is hydrogen, optionally substituted as defined below 1-6 It is selected from an aliphatic or unsubstituted 5-6 membered saturated ring, partially unsaturated ring, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0077] R * Suitable substituents on the aliphatic group include halogen, -R ● , -(Halo R● ), -OH, -OR ● , -O(HaloR * ), -CN, -C(O)OH, -C(O)OR ● , -NH 2 , -NHR ● , -NR ● 2 OR -NO 2 Each R ● is unsubstituted or, if preceded by "halo", is substituted only by one or more halogens, independently C 1-4 Aliphatic, -CH 2 Ph, -O(CH 2 ) 0-1 Ph, or a 5-6 membered saturated ring, partially unsaturated ring, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0078] Suitable substituents on a substitutable nitrogen of an "optionally substituted" group include -R†, -NR† 2 , -C(O)R†, -C(O)OR†, -C(O)C(O)R†, -C(O)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†, wherein each R† is independently selected from hydrogen, C 1-6 aliphatic, unsubstituted -OPh, or an unsubstituted 5-6 membered saturated ring, partially unsaturated ring, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; or, notwithstanding the above definitions, two independent occurrences of R† taken together with their intervening atom(s) form an unsubstituted 3-12 membered saturated ring, partially unsaturated ring, or aryl monocyclic or bicyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0079] Suitable substituents on the aliphatic groups of R† are independently halogen, -R ● , -(Halo R ● ), -OH, -OR ● , -O(HaloR ● ), -CN, -C(O)OH, -C(O)OR ● , -NH 2 , -NHR ● , -NR ● 2 OR -NO 2 And each R ● is unsubstituted or, if preceded by "halo", is substituted only by one or more halogens, independently C 1-4 Aliphatic, -CH 2 Ph, -O(CH 2 ) 0-1 Ph, or a 5-6 membered saturated ring, partially unsaturated ring, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0080] As used herein, the term "substantially" refers to the qualitative state of being entirely or nearly entirely to the extent or degree of a feature or characteristic of interest.

[0081] The term "sprouts," as used herein, are plant material produced from a seed after germination of the seed but prior to the formation of leaves on the plant material. "Edible sprouts" are sprouts that are considered non-toxic to humans.

[0082] A nomenclature for ascarosides is sometimes used that includes several prefix letters followed by a pound sign (#) and a number (e.g., ascr#18). This convention is used in the scientific literature, and one of skill in the art will understand that each such name is associated with a specific chemical structure of a known composition and will readily understand the structure of a molecule depicted using this nomenclature. Unless otherwise specified, all compound identifiers of this form used herein follow the definitions set forth in the C. elegans Small Molecule Identifier Database (SMID-DB), maintained at http: / / www.smid-db.org.

[0083] In the drawings, features are not necessarily drawn to scale, emphasis instead generally being placed upon illustrating principles of the disclosed compositions and methods, and not intended to be limiting. For clarity, not every component may be labeled in the drawings. In the following description, various embodiments are described with reference to the following drawings: [Brief description of the drawings]

[0084] [Figure 1] 1 shows a bar graph comparing the effect of treatments on Salmonella numbers in sprouts produced from alfalfa seeds treated with an ascaroside solution.

[0085] [Diagram 2] 1 shows a bar graph comparing the effect of treating seeds with an ascaroside solution compared to a control sample on the upregulation of plant defense genes.

[0086] [Figure 3A] 1 shows a bar graph comparing the effect of spraying rice seeds with an ascaroside solution on rice emergence.

[0087] [Figure 3B] 1 shows a bar graph comparing the effect of spraying rice seeds with an ascaroside solution on rice height.

[0088] [Figure 4A] FIG. 1 shows the effect of ascr#18 treatment of tomato plant (cv. Sweet hybrid 100) seeds on the lesion size caused by an oomycete pathogen.

[0089] [Figure 4B] FIG. 1 shows the effect of ascr#18 treatment of tomato plant (cv. M82) seeds on the lesion size caused by an oomycete pathogen. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0090] Compositions and methods are provided for inhibiting pathogen growth in seeds, plants, or plant parts. The compositions include at least one ascaroside. Additional components include agriculturally acceptable carriers and components for enhancing pathogen inhibition or components for enhancing sprout formation or growth. The methods include soaking, spraying, coating, contacting seeds and / or plant sprouts with an ascaroside, or providing an ascaroside in the plant growth medium to prevent or inhibit pathogen growth within the growing plant.

[0091] The compositions and methods of the present invention control pathogens, particularly food-borne human pathogens. Pathogens include human pathogens such as viruses, bacteria, fungi, parasites and / or oomycetes. Exemplary food pathogens include disease-causing pathogens such as Salmonella, Clostridium perfringens, Campylobacter, Staphylococcus aureus (Staph), Escherichia coli, Listeria, and the like.

[0092] In certain embodiments, the seeds treated with ascarosides are the seeds of plants capable of producing edible sprouts and / or leafy vegetables. Seeds capable of producing marketable edible sprouts include, but are not limited to, seeds of edible legume crops, seeds of edible cereal grains, seeds of edible oilseed crops, seeds of edible cabbage crops, seeds of edible wild grasses, seeds of edible parsley crops, seeds of edible onion crops, seeds of edible vegetables, and seeds of edible herbs. Leafy vegetables include, but are not limited to, kale, microgreens, collard greens, spinach, cabbage, beet leaves, mustard greens, watercress, lettuce, Swiss chard, yellow radish, endive, bok choy, turnip leaves, broccoli, coriander, etc. In certain embodiments, the seeds of plants treated with one or more ascarosides are the seeds of crops.

[0093] In one aspect, the invention provides a method of inhibiting the growth of human pathogens in or on a plant, comprising treating seeds of the plant with one or more ascarosides, hi certain embodiments, plants grown from such seeds are characterized as being more resistant to the growth of human pathogens on or within their tissues, as compared to plants grown from untreated seeds under identical conditions.

[0094] In another aspect, the invention provides a method of inhibiting the growth of human pathogens in or on a plant, comprising germinating seeds of the plant in a growth medium enriched with one or more ascarosides, hi certain embodiments, plants grown in such a medium are characterized as being more resistant to the growth of human pathogens on or within their tissues, as compared to plants grown under identical conditions using a non-enriched medium.

[0095] In another aspect, the invention provides a method of inhibiting the growth of human pathogens in or on plants, comprising treating plant seeds with one or more ascarosides and germinating those seeds in a growth medium enriched with one or more ascarosides. In certain embodiments, plants grown in such conditions are characterized as being more resistant to the growth of human pathogens on or within their tissues, as compared to plants grown from untreated seeds using unenriched medium.

[0096] Ascarosides are secondary metabolites produced by nematodes. Numerous structurally diverse ascaroside structures have been identified in nature, and these molecules are believed to function as an evolutionarily conserved chemical language that nematodes use to control many aspects of their development. Ascarosides are also perceived by other organisms and have been shown to have a variety of effects on many organisms, including bacteria, fungi, plants, and mammals, including humans. In the present disclosure, application of ascarosides to plant seeds has been shown to activate and prime plant defenses to provide protection against colonization and / or proliferation by non-plant pathogens, including human pathogens. Such protection includes preventing the proliferation of pathogens within cultivated plant tissues. The method of the present invention of stimulating the plant's innate defense system is a unique tool to combat pathogens that invade seeds or internal plant tissues and are difficult to eradicate using current methods. When stimulated by the composition of the present invention, the defense response of the seed-treated plant provides protection against pathogens for several weeks after germination. This is longer than the period required for commercial sprout production, which is typically completed in three to seven days.

[0097] Ascarosides are derivatives of the sugar ascarylose, a dideoxy sugar lacking hydroxyl groups at positions 3 and 6. Ascarosides have the formula I: [ka] wherein Z is an optionally substituted C 2-40 is an aliphatic group, Ra and R b Each of is independently -H or -C 1-20 aliphatic, C 1-20 Achill, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxy protecting group, phosphorus-bridged functional group, sulfur-bridged functional group, silicon-bridged functional group, C 2-20 Carbonates (e.g., -C(O)OR c part), C 2-20 Carbamates (e.g., -C(O)N(R c ) 2 part), C 2-20 Thioesters (e.g., -C(S)R c part), C 2-20 Thiocarbonates (e.g., -C(S)OR c part), C 2-20 Dithiocarbonates (e.g., -C(S)SR c part), C 1-20 Thiocarbamates (e.g., -C(S)N(R c ) 2 a linker moiety, a sugar moiety, a peptide, a polymer chain, or to another ascaroside molecule via a bond or a carbon-containing linker moiety; R c represents independently at each occurrence -H, optionally substituted C 1-12 Aliphatic, optionally substituted C 1-12 is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; R a and R b may be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, optionally containing one or more sites of unsaturation.

[0098] In certain embodiments, Z is (i) -CH(CH 3 )-R 1 where R 1 is an optionally substituted C 1-40is an aliphatic group; (ii) -CH(CH 3 )-(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (iii) -CH(CH 3 )-(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (iv) -CH(CH 3 )-(CH 2 ) n -CH(OH)-CH-CO 2 R 32 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (v) -CH(CH 3 )-(CH 2 )n -C(O)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (vi)-(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (vii)-(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (viii)-(CH 2 ) n -CH(OH)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; or (ix)-(CH 2 ) n -C(O)-CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 A linkage via a bond or a carbon-containing linker moiety 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 ascaroside molecule. In certain embodiments, Z is (x)-CH(CH 3 )-(CH 2 ) n -CON(R 3 ) 2 In the formula, n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (xi) -CH(CH 3 )-(CH 2 ) n -CH=CH-CON(R 3 ) 2 In the formula, n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (xii) -CH(CH 3 )-(CH 2 ) n -CH(OH)-CH-CON(R 3 ) 2 In the formula, n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (xiii) -CH(CH 3 )-(CH 2 )-C(O)-CH-CON(R 3 ) 2 In the formula, n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (xiv)-(CH 2 ) n -CON(R 3 ) 2 In the formula, n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (xv)-(CH 2 ) n -CH=CH-CON(R 3 ) 2 In the formula, n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; (xvi)-(CH 2 ) n -CH(OH)-CH-CON(R 3 ) 2 In the formula, n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety 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 ascaroside molecule; or (xvii)-(CH 2 ) n -C(O)-CH-CON(R 3 ) 2 In the formula, n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 A linkage 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 ascaroside molecule via a bond or a carbon-containing linker moiety. In certain embodiments, R a is -H.

[0099] In certain embodiments, R a is -H. In certain embodiments, R b is -H. In certain embodiments, R a and R b are identical. In certain embodiments, R a and R b are both -H.

[0100] In certain embodiments, R a and R b are different. In certain embodiments, R a is -H, 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, R b is a paraoxybenzoate ester. In certain embodiments, R a is -H, R b is an indole-3-carboxylic acid ester. In certain embodiments, R a is -H, R b is (E)-2-methyl-2-butenoic acid ester. In certain embodiments, R a is -H, R b is a picolinic acid ester. In certain embodiments, R a is -H, R b is a nicotinate ester. In certain embodiments, R a is -H, R b is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoic acid ester. In certain embodiments, R a is -H, R b is 4-((4-hydroxyphenethyl)amino)-4-oxobutanoic acid ester.

[0101] In certain embodiments, Ra and R b are both -H and Z is selected from the formulas defined in (i) to (ix) above. In certain embodiments, Ra and Rb are both -H and Z is according to formula (i) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (ii) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (iii) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (iv) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (v) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (vi) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (vii) above. a and R b are both -H and Z conforms to formula (viii) above. a and R b are both -H and Z conforms to formula (ix) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (x) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xi) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xii) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xiii) above. a and R b are both -H and Z is according to formula (xiv) above.a and R b are both -H and Z conforms to formula (xv) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xvi) above. In certain embodiments, R a and R b are both -H and Z is according to formula (xvii) above.

[0102] In certain embodiments, R 2 is -H. In certain embodiments, R 2 is a metal cation. In certain embodiments, R 2 is an organic cation (e.g., a nitrogen- or phosphorus-centered cationic group). In certain embodiments, R 2 is an optionally substituted C 1-20 In certain embodiments, R 2 is an optionally substituted C 1-12 In certain embodiments, R 2 is an optionally substituted C 1-8 In certain embodiments, R 2 is an optionally substituted C 1-6 In certain embodiments, R 2 is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. 2 is an optionally substituted aromatic group. In certain embodiments, R 2 is a glycoside. In certain embodiments, R 2 In certain embodiments, R 2 In certain embodiments, R 2 comprises a nucleotide.

[0103] In certain embodiments, at least one R 3 is -H. In certain embodiments, both R 3 The group is -H. In certain embodiments, at least one R 3is an optionally substituted C 1-20 In certain embodiments, both R 3 The groups may be the same or different, optionally substituted C 1-20 In certain embodiments, at least one R 3 is an optionally substituted C 1-12 In certain embodiments, at least one R 3 is an optionally substituted C 1-8 In certain embodiments, at least one R 3 is an optionally substituted C 1-6 In certain embodiments, at least one R 3 is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. 3 -CH 2 CH 2 In certain embodiments, at least one R 3 -CH 2 CH 2 OR 2 where R 2 are genus and subgenus as defined herein. In certain embodiments, at least one R 3 is an optionally substituted aromatic group. In certain embodiments, at least one R 3 In certain embodiments, at least one R 3 In certain embodiments, at least one R 3 In certain embodiments, at least one R 3 In certain embodiments, at least one R 3 comprises a nucleotide.

[0104] In certain embodiments, the ascaroside is [ka] wherein x is an integer from 1 to 22; a , R b and R 2 Each of the above is defined as a genus and subgenera herein.

[0105] In certain embodiments, the ascaroside is [ka] wherein x, R a and R b Each of the above is defined as a genus and subgenera herein.

[0106] In certain embodiments, the ascaroside is [ka] wherein y is an integer from 1 to 20; a , R b and R 2 Each of the above is defined as a genus and subgenera herein.

[0107] In certain embodiments, the ascaroside is [ka] wherein y, R a and R b Each of the above is defined as a genus and subgenera herein.

[0108] In certain embodiments, the ascaroside is [ka] wherein x is an integer from 1 to 22; 2 are defined above and are of genus and subgenera herein.

[0109] In certain embodiments, the ascaroside is [ka] where x is as defined above and in the genera and subgenera herein.

[0110] In certain embodiments, the ascaroside is [ka] wherein y is an integer from 1 to 20; 2 are defined above and are of genus and subgenera herein.

[0111] In certain embodiments, the ascaroside is [ka] where y is as defined above and in the genera and subgenera herein.

[0112] In certain embodiments, the ascaroside is [ka] wherein x is an integer from 1 to 22; a , R b and R 3 Each of the above is defined as a genus and subgenera herein.

[0113] In certain embodiments, the ascaroside is [ka] wherein x and R 3 Each of the above is defined as a genus and subgenera herein.

[0114] In certain embodiments, the ascaroside is [ka] wherein y is an integer from 1 to 20; a , R b and R 3 Each of the above is defined as a genus and subgenera herein.

[0115] In certain embodiments, the ascaroside is [ka] wherein y and R 3 Each of the above is defined as a genus and subgenera herein.

[0116] In one embodiment, ascarosides useful in the context of the present disclosure have the general structure (I), where Z is -CH(CH 3 )-(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 They are aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides and can be used to inhibit the growth of human pathogens in or on the surface of plants.

[0117] In one embodiment, ascarosides useful in the context of the present disclosure have the general structure (I), where Z is -CH(CH 3 )-(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0118] In one embodiment, ascarosides useful for the present invention have the general structure (I), where Z is -CH(CH3 )-(CH 2 ) n -CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 They are aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides and can be used to inhibit the growth of human pathogens in or on the surface of plants.

[0119] In one embodiment, ascarosides useful for the present invention have the general structure (I), where Z is -CH(CH 3 )-(CH 2 ) n -CH=CH-CO 2 R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0120] Particular ascarosides useful in the present invention include, but are not limited to, ascr#7 and ascr#18. [ka]

[0121] In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of ascr#9, ascr#12, ascr#14, ascr#1, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, ascr#24, ascr#26, ascr#28, ascr#30, ascr#32, ascr#34, and ascr#36. In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of ascr#9, ascr#14, ascr#10, and ascr#18.

[0122] In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of ascr#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22. In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of bhas#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

[0123] In certain embodiments, the ascaroside used in the methods provided is selected from the group consisting of bhas#9, bhas#10, bhas#16, bhas#18, bhas#22, bhas#24, bhas#26, bhas#28, bhas#30, bhas#32, bhas#34, bhas#36, bhas#38, bhas#40, and bhas#42.

[0124] In certain embodiments, the ascaroside used in the methods provided 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.

[0125] In certain embodiments, the ascaroside used in the methods provided is selected from the group consisting of ascr#18, oscr#16, oscr#17, oscr#15, bhas#18, bhos#16, glas#18, dhas#18, ibha#18, ibho#16, icas#18, icos#15, icos#16, and any combination of two or more thereof.

[0126] Ascarosides can be obtained from natural sources (e.g., nematodes) or can be synthetically prepared. Ascarosides can be synthetically prepared, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascarylose. An exemplary method for preparing ascarosides includes providing 1-O-substituted rhamnose as a raw material, forming a mono-sulfonate ester at the 3-OH group of the raw material, and treating the mono-sulfonate ester with a hydride source to form 1-O-substituted ascarylose. In certain embodiments, the formation of the mono-sulfonate ester is carried out at the 2- or 4-position of the rhamnose raw material without the use of a hydroxyl group protecting group on the substrate. In certain embodiments, such methods include contacting the raw material with a sulfonating agent (i.e., a sulfonyl halide, sulfonic anhydride, or similar reagent) in the presence of a Lewis acid. Specific details regarding the synthesis of 1-O-substituted ascarylose can be found in PCT Application No. PCT / IB2021 / 056981, filed March 2, 2022 (published as WO2022 / 024067), which is incorporated herein by reference.

[0127] For ascaroside synthesis, it may be desirable and efficient in some embodiments to utilize a rhamnose raw material having a substituent on the 1-OH position that is identical to the desired substituent of the ascaroside of interest, or a rhamnose raw material that is a convenient synthetic precursor to the desired substituent. When 1-O-substituted rhamnose is used as a precursor, the method of making the ascaroside can begin with a direct reaction of the 1-O-substituted rhamnose, or can include a first step of converting rhamnose to 1-O-substituted rhamnose. Methods for converting OH to OZ are generally known in the art, provided that the 1-O-substituted rhamnose is dependent on the Z substituent.

[0128] Prior to use, the ascarosides used in the compositions of the present invention may be dissolved in water to form an aqueous solution of the ascaroside. However, some types of ascarosides have limited solubility in water. Therefore, it may be necessary to first dissolve the ascaroside in a co-solvent that is water-miscible and acceptable for use in plant materials intended for human consumption. A variety of water-miscible solvents are known and can be used for this purpose. A preferred co-solvent is ethanol. Another preferred co-solvent is propylene glycol. The water-miscible solvent may be a food grade solvent. In one embodiment, a stock solution of the ascaroside dissolved in ethanol or propylene glycol can be prepared. This stock solution is added to a suitable amount of water to prepare an aqueous solution of the ascaroside. As used herein, "aqueous solution" includes solutions that primarily contain water as the solvent and optionally contain one or more co-solvents in amounts up to about 45%, up to about 40%, up to about 35%, up to about 30%, up to about 25%, up to about 20%, up to about 15%, up to about 10%, up to about 5%, up to about 1%, or up to about 0.1% by volume.

[0129] In one embodiment, the seeds of the plant may be treated with an ascaroside solution (e.g., an aqueous solution of one or more ascarosides) by soaking the seeds in the ascaroside solution. The seeds are soaked in the ascaroside solution for a time sufficient to allow the ascarosides to enter the seeds. Typically, the seeds are soaked for about 1 minute to about 12 hours (e.g., about 5 minutes to about 6 hours, or about 30 minutes to about 3 hours, or about 6 hours to about 12 hours), although such times are not intended to be limiting and longer or shorter ranges of times can be used in some embodiments. In certain embodiments, the seeds are soaked in a solution containing one or more ascarosides for about 1 minute, about 5 minutes, about 10 minutes, about 20 minutes, about 30 minutes, about 45 minutes, about 1 hour, about 2 hours, about 3 hours, about 4 hours, about 5 hours, about 6 hours, about 7 hours, about 8 hours, about 9 hours, about 10 hours, about 11 hours, or about 12 hours.

[0130] The change in weight of the seeds can be used to determine whether the seeds have been soaked in the ascaroside solution for a sufficient time to allow the ascarosides to enter the seeds. Prior to soaking the seeds in the ascaroside solution, the seeds are weighed to determine the "dry weight" of the seeds. The seeds are then soaked in the ascaroside solution for a predetermined time (e.g., the times described above). The seeds are removed from the ascaroside solution and dried to remove all or a portion of the moisture on the seed surface. The dried seeds are weighed to determine the amount of water absorbed by the seeds during soaking in the ascaroside solution. A substantial positive change in the weight of the seeds indicates ascaroside solution absorbed by the seeds. A weight change of more than 2%, more than 3%, more than 4%, more than 5%, more than 6%, more than 8%, more than 10%, more than 12%, more than 15%, or more than 20% indicates that a sufficient amount of the ascaroside solution has been absorbed.

[0131] The ascaroside solution has an ascaroside concentration in the range of 0.001 mM to about 1.0 mM (e.g., about 0.01 mM to about 0.5 mM, about 0.1 mM to about 0.5 mM, or about 0.5 to about 1 mM). When the ascaroside solution contains more than one ascaroside, the term "ascaroside concentration" refers to the total concentration of all ascarosides in the solution. Exemplary ascaroside concentrations in the ascaroside solution used to treat the seeds include 0.001 mM, 0.005 mM, 0.01 mM, 0.05 mM, 0.1 mM, 0.5 mM, and 1.0 mM.

[0132] In one embodiment, the seeds of the plant may be treated with an ascaroside seed coating formulation (e.g., a liquid or powder composition containing one or more ascarosides). Seed coating may be accomplished by any known means, such as spraying the composition onto the seeds or stirring the seeds with the composition. In contrast to soaking, these methods typically use a minimal amount of liquid. After application, the seeds are typically dried to provide a germinating treated or coated seed that is stable during storage and transport. In certain embodiments, such seed treatments are applied at a rate that provides treated seeds with an ascaroside content of about 0.01 ppm to about 100 ppm by weight. In certain embodiments, such seeds include about 0.1 to about 10 ppm ascarosides. In certain embodiments, such seeds include about 0.2 to about 5 ppm ascarosides. In certain embodiments, such seeds include about 1 to about 10 ppm ascarosides. In certain embodiments, such seeds contain from about 2 to about 5 ppm ascarosides. In certain embodiments, such seeds contain from about 0.1 to about 1 ppm ascarosides. In certain embodiments, such seeds contain from about 0.5 to about 2.5 ppm ascarosides. In certain embodiments, the method includes treating the seeds, drying the treated seeds, storing the seeds, and optionally transporting the seeds to a production facility prior to producing sprouts from the treated seeds.

[0133] In a typical step in sprout cultivation, the seeds are soaked in water to increase their moisture content and bring them out of quiescence. It may therefore be convenient to treat the seeds with an ascaroside composition during this soaking step of sprout production. The seeds are then placed in a container that allows them to be periodically rinsed with water without removing them from the container. Depending on the type of seed, the seeds are typically rinsed two to four times per day. This provides the seeds with enough moisture to germinate and grow. In certain embodiments, one or more of these rinses may include an ascaroside. Depending on the type of plant associated with the seed, the sprouts are cultivated after they have grown to about 5 to 8 centimeters. As previously mentioned, this process of producing sprouts for consumption can lead to bacterial growth.

[0134] There are many different types of sprouts that are cultivated and consumed. Examples of general classes of edible sprouts include, but are not limited to, bean sprouts, grain sprouts, oilseed sprouts, cabbage sprouts, parsley sprouts, onion sprouts, vegetable sprouts and herb sprouts. Examples of legume sprouts include, but are not limited to, mung bean sprouts, soybean sprouts, alfalfa sprouts, clover sprouts, fenugreek seed sprouts, lentil sprouts, pea sprouts and chickpea sprouts. Examples of grain sprouts include, but are not limited to, oat sprouts, corn sprouts, rice sprouts, barley sprouts and rye sprouts. Examples of oilseed sprouts include, but are not limited to, sesame sprouts, sunflower sprouts, almond sprouts, hazelnut sprouts, hemp sprouts, linseed sprouts and peanut sprouts. Examples of cabbage sprouts include, but are not limited to, broccoli sprouts, cabbage sprouts, watercress sprouts, mustard sprouts, mizuna sprouts, radish sprouts, radish sprouts, yellow sprouts, tatsoi sprouts and turnip sprouts. Examples of parsley sprouts include, but are not limited to, carrot sprouts, celery sprouts, fennel sprouts and parsley sprouts. Examples of onion sprouts include, but are not limited to, onion sprouts, chive sprouts and shallot sprouts. Examples of vegetable and herb sprouts include, but are not limited to, spinach sprouts, lettuce sprouts, milk thistle sprouts, and lemongrass sprouts.

[0135] In one embodiment of the present invention, it has been found that soaking seeds from plants that can be used to form edible sprouts in an ascaroside solution can inhibit the formation of pathogens in and on the surface of the sprouts during growth and cultivation of the sprouts. Without wishing to be bound by any particular theory, it is believed that the protective effect of ascaroside treatment is due to the upregulation of plant defense genes in the presence of the ascaroside.

[0136] Biofilm formation is one of the main defense strategies used by bacteria against hostile environmental conditions. Biofilm formation by bacteria on the exterior or interior of sprouts can provide a protected environment in which pathogens can colonize and multiply. Without wishing to be bound by any particular theory, it is believed that ascarosides can affect the ability of bacteria to form biofilms. By inhibiting biofilm formation, ascarosides can remove one of the main defense mechanisms of bacteria.

[0137] Treatment of seeds or plants with an ascaroside solution can control a variety of human pathogens. Examples of bacteria that can be controlled include, but are not limited to, Salmonella enterica, Salmonella serovar Muenchen, Salmonella Saintpaul, Escherichia coli O157:H7, Escherichia coli O157:NM, Escherichia coli O121, Escherichia coli O104:H4, and Listeria monocytogenes.

[0138] Based on the weight change of the seeds after soaking in the ascaroside solution, it is theorized that there is about 0.01 to about 100 ppm of ascaroside absorption by the seeds after soaking in the ascaroside solution. The amount of ascaroside absorption in the seeds is a function of the concentration of ascaroside in the ascaroside solution and the duration of soaking. Thus, the amount of ascaroside present in the treated seeds can be varied by adjusting these parameters. Typically, the seeds are soaked in the ascaroside solution at ambient temperature and pressure. In some embodiments, the seeds may be soaked in the ascaroside solution at a temperature and / or pressure higher than ambient temperature and / or pressure. Treatment of the seeds at a temperature and / or pressure higher than ambient temperature and / or pressure may kill some or all human pathogens that may be present in and / or on the seed surface.

[0139] The method of treating seeds with an ascaroside solution is particularly useful for treating seeds that will be used in sprout production, but can also be used to treat crop seeds. Crops with seeds that can be treated with an ascaroside solution include, but are not limited to, corn, wheat, rice, soybean, tomato, lettuce, potato, barley, and beans. The method of treating the seeds of the crop is similar to the method of treating the seeds of sprout seeds. The seeds of the crop are soaked in the ascaroside solution for a sufficient time to allow the ascarosides to enter the seeds. The soaking time and the composition and concentration of the ascaroside solution are similar or identical to those described above. After treatment with the ascaroside solution, the seeds may be planted in the ground in a manner typical for the particular crop. Crops grown from seeds treated with an ascaroside solution can exhibit better resistance to human pathogens, as well as bacteria and fungi that can affect the health or growth of the plant.

[0140] In an alternative method of sprout production, seeds from plants used to produce edible sprouts are treated by soaking the seeds in an ascaroside solution for a time sufficient to bring the seeds out of quiescence (i.e., the seeds begin to germinate). In this method, the initial soaking in the ascaroside solution accomplishes both the infiltration of the ascarosides into the seeds and the first step in the sprout formation process. After soaking for a time sufficient to ensure that the seeds are in a germinated state, the seeds are placed in a suitable container for sprout formation. The seeds are then periodically rinsed until the sprouts reach a suitable length. In an alternative method of sprout production, the ascarosides are included in the water used to periodically rinse the sprouts. The ascarosides may be present during each rinse, during only one rinse, or during several rinses (i.e., alternating one or more treatments with ascarosides with one or more treatments without ascarosides).

[0141] Treatment of seeds with an ascaroside solution has been unexpectedly found to increase the germination rate of the seeds and accelerate the growth and maturation of the plants. In another embodiment, the seeds of plants used for sprout or crop production are treated with an ascaroside solution to increase the germination rate and accelerate the growth of the resulting plants. As with other embodiments, the seeds of the crop are soaked in an ascaroside solution for a time sufficient to allow one or more ascarosides to enter the seeds. After treatment with the ascaroside solution, the seeds are used for sprout or crop production as needed. The increase in the germination rate of the seeds and the accelerated growth and maturation of the resulting plants can vary. In some embodiments, a significant increase in the germination rate is observed. In some embodiments, a significant increase in the percentage of germinated seeds (vs. non-germinated seeds) within a given sample that germinates is observed. In some embodiments, a significant increase in the rate of growth and / or maturation of the plants is observed.

[0142] In another embodiment, when the ascaroside solution is sprayed onto a plant, it has been found to be effective in inhibiting human pathogen growth and / or bacteria and fungi that may affect the health or growth of the plant. The ascaroside solution used to treat the plant may have a substantially lower concentration than the concentration of the ascaroside solution used to treat the seed once the plant has begun to grow. For a typical crop or sprout, the ascaroside solution used to spray treat these plants ranges from about 1 ppb to about 50 ppm. For example, the concentration of ascaroside used to spray treat the plant may be 1 ppb, 10 ppb, 50 ppb, 100 ppb, 250 ppb, 500 ppb, 1 ppm, 2 ppm, 3 ppm, 5 ppm, 10 ppm, 15 ppm, 20 ppm, 25 ppm, 30 ppm, 40 ppm, or 50 ppm.

[0143] Surprisingly, seed treatment with an ascaroside solution provides protection against bacterial and fungal contamination for at least 6 weeks. This is particularly useful for crops that require more than one month to obtain the crop. This property of the ascaroside solution can be a very effective preventive measure for the crop. Application of the ascaroside solution to a large amount of seeds is much easier to carry out than spraying the entire crop field. In some embodiments, seed treatment with an ascaroside solution can provide enhanced protection against bacterial and fungal contamination for at least 1 week, at least 2 weeks, at least 3 weeks, at least 4 weeks, at least 5 weeks, or at least 6 weeks.

[0144] Among leafy greens, baby leaf vegetables are gaining in popularity. Although definitions vary, these crops are best defined as vegetables harvested after the emergence of the true leaves but before the 8-leaf stage. In the United States, a variety of leafy salad crops are grown for baby leaf salad mix, including lettuce, spinach, mustard leaves, Chinese cabbage (also known as bok choy), kale, yellow bell pepper, and beet leaves. Baby leaf leaves are typically harvested by hand cutting or plucking the outermost most mature leaves. Damage caused to the leaves during harvesting provides a favorable entry point for pathogens to contaminate the plant's internal tissues, at which point these pathogens may remain protected even from post-harvest disinfectant washes. Seeds of plants used to produce leafy greens can be treated with an ascaroside solution to protect against pathogen contamination after the plant is harvested. The protection afforded by the treatment of the plant's seeds may minimize opportunistic pathogen contamination during the harvesting of the plant's leaves. Such protection may also be conferred to the plant by spraying the ascaroside solution onto the leaves after the plant has grown (which can optionally be done in addition to treating the seeds with the ascaroside solution, or can be performed on plants grown from untreated seeds).

[0145] Microgreens are edible young plants that are harvested 7-14 days after planting when they begin to produce their first true leaves, and therefore share characteristics of both sprouts and leafy greens, such as the potential to carry food-borne pathogens. Like leafy greens, microgreens are also harvested by hand, cutting just above the soil line, and are similarly susceptible to pathogen contamination. In one embodiment, the seeds of the plants used to produce microgreens can be treated with an ascaroside solution to protect the plants from pathogen contamination after harvest. Such protection can minimize opportunistic pathogen contamination during the harvesting of the microgreens. Such protection can also be imparted to the plants used to produce microgreens by spraying the ascaroside solution on the leaves after the plants have grown. Again, such foliar application can be optionally performed in addition to treating the seeds with the ascaroside solution, or can be performed on plants grown from untreated seeds.

[0146] The seed treatment and leaf treatment provided herein have been shown to reduce or prevent pathogen contamination throughout the early life cycle of the plant.Furthermore, the plant itself has been shown to be protected from pathogen contamination when harvesting and insect damage occurs.As mentioned above, seed and plant treatment with ascarosides appears to upregulate plant defense genes, allowing the plant to defend itself against pathogen contamination.This type of long-term protection helps ensure that the edible product of the plant is protected, whether in sprout or leaf form.

[0147] In addition, the seed treatments and foliar treatments provided herein have been shown to reduce or prevent pathogen contamination without the need for additional types of treatments. While the seed treatments and foliar treatments provided herein may be the only pathogen reduction treatments performed, in other embodiments, these treatments can be used in conjunction with one or more known methods for reducing or eliminating pathogens, including, but not limited to, treatments with acidic electrolyzed water, ozonated water, chlorine dioxide, trisodium phosphate, calcium hypochlorite (bleaching powder), and sodium hypochlorite (bleach). EXAMPLES

[0148] The following examples illustrate certain embodiments of the invention and are not intended to be limiting.

[0149] Treatment of alfalfa seeds with ascr#18 to prevent Salmonella enterica contamination This study evaluates the effectiveness of seed treatment with ascr#18 in preventing the growth of Salmonella enterica by comparing the levels of contamination produced by artificial inoculation of ascaroside-treated and untreated germinable seeds with a strain of Salmonella enterica known to be the cause of sprout-associated food poisoning in humans.

[0150] Salmonella enterica serovar Stanley, which was previously isolated from an alfalfa sprout-associated outbreak of human gastrointestinal infection. Seeds were inoculated, evaluated, and propagated as described in Appl. Environ. Microbiol. 2017;83(7):e03170-16 doi:10.1128 / AEM.03170-16 and J. Food Prot. (2020) 83(7):1218-1226 (doi:10.4315 / JFP-20-021), the entire contents of each of which are incorporated herein by reference. Alfalfa seeds (Medicago sativa) are first disinfected to inactivate background microbiota, and then soaked in solutions containing various concentrations of ascr#18 (e.g., 0.1-1000 uM) or in a mock solution lacking ascr#18. The seeds were then mixed with sterilized sandy soil and incubated for 10 min at 4 °C for 1 h as described in J. Food Prot. (2020) 83(7):1218-1226. 4 CFU of freeze-dried nalidixic acid-resistant (NA) Salmonella cells were inoculated. Inoculated alfalfa seeds and uninoculated control seeds (1 g each) were then soaked in solutions containing 0.0 mM (mock solution), 0.001 mM or 1.0 mM ascr#18 and incubated at room temperature for 20 min. The ascr#18 stock solution was prepared by dissolving acr#18 in ethanol and diluting the concentrated stock solution in distilled water at appropriate ratios to provide concentrations for the seed soaking experiments. To account for any effects caused by ethanol, the two mock treatments contained an amount of ethanol equal to that of the two ascr#18 treatments. Seeds treated with sterile distilled water were included as an additional control. Analysis of the soaked seeds showed that the alfalfa seeds gained about 8-10% of their dry weight during the 20 min treatment, which means that about 0.03 and 30 ppm of ascr#18 were absorbed in the seeds treated with the 0.001 mM and 1.0 mM solutions, respectively.

[0151] Alfalfa seeds inoculated with Salmonella from the different treatments were placed on plates and allowed to grow for 7 days. Samples were taken every other day for microbial analysis. Five seedlings per sample were harvested and crushed, and 10-fold serial dilutions from treated samples were plated on Bismuth Sulfite Agar (BSA) or NA-modified Tryptic Soy Agar (NA-TSA) media to quantify Salmonella populations. Enrichment analysis was performed if the number of Salmonella cells was below the detection limit. Two independent trials were performed and analyzed using Fisher's least significant difference test (95% confidence interval) to determine differences in Salmonella populations (log CFU / g of sprout tissue) recovered from sprouts. Inoculated and uninoculated control seeds were germinated, grown, sampled, and analyzed for the presence of Salmonella as described in J. Food Prot. (2020) 83(7):1218-1226.

[0152] The results are presented in Figure 1. Two mock solutions were used as controls. Mock solution 1 is an aqueous solution of ethanol equivalent to the ethanol concentration present in a 0.001 mM ascr#18 solution. Mock solution 2 is an aqueous solution of ethanol equivalent to the ethanol concentration present in a 1.0 mM ascr#18 solution. Salmonella counts on sprouts from alfalfa seeds treated with a 1.0 mM solution (associated with an ascr#18 uptake of 30 ppm) were 5.91-7.21 log CFU / g lower when placed on NA-TSA than the counts on sprouts from the corresponding solvent control (mock solution 2) or seeds treated with water only. Similar to the NA-TSA plates, Salmonella counts on BSA plates from seed treatments with a 1.0 mM ascr#18 solution were found to be 5.61-7.27 log CFU / g lower than the controls (results not shown). In both media, the Salmonella counts in samples treated with 1.0 mM ascr#18 solution were below the detection limit even after enrichment, meaning that Salmonella cells were not detectable. Treatment of seeds with 0.001 mM ascr#18 solution was less effective than 1.0 mM ascr#18 solution, but still showed some reduction in Salmonella levels, ranging from 0.11 to 2.34 log CFU / g on NA-TSA and 0.03 to 2.01 log CFU / g on BSA, when compared to the corresponding solvent control (mock solution 1). In an independent experiment, treatment with ascr#18 solution resulted in similar levels of contamination suppression on alfalfa sprouts inoculated with another outbreak-associated strain, Salmonella enterica serovar Cubana (results not shown).

[0153] Seed treatment with ascr#18 was found to be effective in preventing Salmonella contamination in cultivated sprouts compared to untreated controls.

[0154] The ascarosides used in seed treatment also have a short half-life in the plant after application, and their persistent action was found to be the result of activation of defense priming and not due to the constant presence of the active ingredient. These results are encouraging, as the ascr#18 content of the sprouts produced is 1000-fold lower than the seed treatment levels. As the minimum effective application rate required for commercial sprout production is likely to be lower than the rate used in these trials, it is expected that residual ascr#18 levels in a commercial setting will be even lower.

[0155] Unlike other products that activate defense responses in plants, treatment with ascarosides does not negatively affect plant vegetative growth. On the contrary, ascarosides have been shown to enhance germination and accelerate the growth and maturation of some crop plants.

[0156] Ascr#18 activates defense gene expression in alfalfa To evaluate whether the protective effect of ascr#18-based seed treatment is due to upregulation of plant defense genes, alfalfa seeds were treated with ascr#18 as described above and grown for 7 days. Sprout tissues were analyzed by qRT-PCR for the expression of plant defense marker genes, such as cyclin-dependent protein kinase inhibitor (gene A), RPM1 (gene B), NAC domain-containing protein 72 (gene C), salicylic acid carboxyl methyltransferase 3 (gene D), RPV1-like (gene E), PR-1-like (gene F), and zinc finger transcription factor (gene G). The test results are presented in Figure 2. Ascr#18 treatment enhanced the expression of all seven genes, three of which had statistically significant levels of enhancement. These results indicate long-term activation of defense responses in alfalfa by ascr#18-based treatment. Expression of these genes was also upregulated in 7-day-old alfalfa plants sprayed with 1 μM ascr#18 24 h before harvesting for RNA analysis (results not shown).

[0157] Determination of Ascr#18 residues on sprouts derived from treated seeds A preliminary study was conducted to evaluate the ascr#18 residue levels present in 7-day-old sprouts grown from seeds treated with 1.0 mM ascr#18 solution as described above. Harvested sprouts were freeze-dried, crushed, extracted with 80:20 methanol:water, and then analyzed by liquid chromatography coupled with mass spectrometry (LC-MS). Only traces of ascr#18 (approximately 30 ppb) could be detected in these sprouts. This is consistent with previous studies that showed that ascarosides have a short half-life in plants after application, and that their persistent action is the result of the activation of defense priming and not due to the constant presence of the active ingredient. These results are encouraging, as the ascr#18 content of the sprouts produced is 1000 times lower than the seed treatment level. Because the minimum effective application rates required for commercial sprout production are likely to be lower than the rates used in these trials, it is expected that residual ascr#18 levels in a commercial setting will be even lower than those found in this experiment.

[0158] Ascaroside ascr#18 promotes germination and increases seedling growth Unlike other products that activate defense responses in plants, treatment with ascr#18 does not negatively affect plant yield. On the contrary, ascr#18 has been shown to enhance germination and accelerate growth and maturation of some crops. Rice seeds were treated by soaking in mock or 1 μM ascr#18 solution. Emergence was measured 4, 5, 6, and 7 days after planting (Figure 3A). Plant height was measured 10 days after planting (Figure 3B). (Data are mean ± SEM (n≧21). ***P≦0.0004; two-tailed t-test). As shown in Figure 3, treatment of rice seeds with ppb levels of ascr#18 resulted in enhanced germination and plant growth. Similar results were obtained from tomato and Arabidopsis (results not shown). Preliminary analyses suggest that ascr#18 treatment does not negatively affect germination, growth, or yield of alfalfa (results not shown).

[0159] The protective effect of ascr#18 lasts for at least 6 weeks after emergence on plants from treated seeds To determine whether the defense response elicited by seed treatment based on ascr#18 is sustained, the effect on resistance to the oomycete pathogen Phytophthora infestans was measured in 6-week-old tomato plants grown from seeds treated with ascr#18 before planting. The test results are presented in Figure 4. Figure 4A shows the effect of ascr#18 treatment on tomato plant (cv. Sweet hybrid 100) seeds on the lesion size caused by the oomycete pathogen. Seeds were treated with 0 μM, 0.01 μM, 0.1 μM and 1 μM ascr#18. Figure 4B shows the effect on lesion size on plants produced from tomato plant (cv. M82) seeds treated with 0, 0.1 and 0.01 μM ascr#18. Six-week-old plants from both tests were inoculated with P. infestans. Lesion size was measured at 5 dpi. **p<0.005; ***p<0.0005; ****p<0.00005; two-tailed t-test. The enhanced protection, as indicated by the reduction in sporocyst lesion size, was similar to that achieved in 6-week-old plants sprayed / dipped in ascr#18 24 h prior to infection. In a similar study, treatment of soybean seeds with ascr#18 solution provided protection against Pseudomonas syringae, Phytophthora sojae, and Soybean Mosaic Virus in soybean plants for at least 3-4 weeks (results not shown).

[0160] The compositions, systems, devices, methods, and processes of the present application are contemplated to encompass variations and adaptations developed using information from the embodiments described in this disclosure. Adaptations or modifications of the methods and processes described herein may be made by one of ordinary skill in the relevant art.

[0161] It will be understood that the use of headings in this disclosure is provided for the convenience of the reader. The presence and / or placement of headings is not intended to limit the scope of the subject matter described herein. Unless otherwise specified, embodiments located in one section of this application apply to other embodiments, both alone and in combination, throughout this application.

[0162] Throughout this specification, when compositions, compounds, or products are described as having, including, or comprising certain components, or processes and methods are described as having, including, or comprising certain steps, it is contemplated that there are additionally articles, devices, and systems of the present application that consist essentially of or consist of the recited components, and processes and methods according to the present application that consist essentially of or consist of the recited processing steps.

[0163] It should be understood that the order of steps or order for performing certain actions is immaterial so long as the method described remains operable. Moreover, two or more steps or actions may be performed simultaneously.

[0164] All publications and patent applications mentioned in this specification are indicative of the level of those skilled in the art to which this invention pertains. All publications and patent applications are herein incorporated by reference to the same extent as if each individual publication or patent application was specifically and individually indicated to be incorporated by reference.

[0165] Although the foregoing invention has been described in some detail by way of illustration and example, for purposes of clarity of understanding, it will be apparent that certain changes and modifications may be practiced which are within the scope of the appended claims.

Claims

1. 1. A method for inhibiting the growth of a human enteric pathogen in or on a plant, the method comprising treating seeds of said plant with a composition comprising one or more ascarosides.

2. The one or more ascarosides have the structure (I): 【Chemistry 1】 wherein Z is an optionally substituted C2-40 aliphatic group; R ａ and R ｂ Each of is independently —H or —C １－２０ aliphatic, C １－２０ Acyl, C １－２０ Heteroaliphatic, aryl, heteroaryl, hydroxy protecting group, phosphorus-bridged functional group, sulfur-bridged functional group, silicon-bridged functional group, C ２－２０ Carbonate esters (e.g., —C(O)OR ｃ part), C ２－２０ Carbamates (e.g., —C(O)N(R ｃ ) ２ part), C ２－２０ Thioesters (e.g., —C(S)R ｃ part), C ２－２０ Thiocarbonates (e.g., —C(S)OR ｃ part), C ２－２０ Dithiocarbonates (e.g., —C(S)SR ｃ part), C １－２０ Thiocarbamate esters (e.g., —C(S)N(R ｃ ) ２ a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; ｃ is independently, at each occurrence, —H, optionally substituted C １－１２ Aliphatic, optionally substituted C １－１２ is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; R ａ and R ｂ may together form an optionally substituted ring, optionally containing one or more heteroatoms, optionally containing one or more sites of unsaturation.

3. Z is, i. -CH(CH ３ )-R １ wherein R １ is an optionally substituted C １－４０ is an 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 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iii. -CH(CH ３ )-(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 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iv. -CH(CH ３ )-(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 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; v. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-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 an 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 C １－２０ an 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 C １－２０ an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; 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 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and ix. f-(CH ２ ) ｎ -C(O)-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 3. The method of claim 2, wherein the hydroxyl group is selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

4. R ａ and R ｂ The method of claim 2, wherein each is —H.

5. 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 The method according to any one of claims 2 to 4, wherein the hydroxyl group is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

6. 2. The method of claim 1, wherein at least one of the one or more ascarosides is ascr#18.

7. Z is -CH(CH ３ )-(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 The method according to any one of claims 2 to 4, wherein the hydroxyl group is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

8. 2. The method of claim 1, wherein at least one of the one or more ascarosides is ascr#7.

9. 9. The method of any one of claims 1 to 4, 6 or 8, wherein treating the seeds of the plant comprises soaking the seeds in an aqueous solution comprising one or more ascarosides.

10. 10. The method of claim 9, wherein the seeds are soaked in the aqueous solution for about 1 minute to about 6 hours.

11. 10. The method of claim 9, wherein the concentration of the one or more ascarosides in the aqueous solution is from about 0.001 mM to about 1.0 mM.

12. 9. The method of any one of claims 1 to 4, 6 or 8, wherein the seeds of the plants are seeds of plants that can be used to produce edible sprouts.

13. 13. The method of claim 12, wherein the seed of the plant is a seed capable of producing an edible pulse sprout.

14. 13. The method of claim 12, wherein the seed of the plant is a seed capable of producing an edible grain sprout.

15. 13. The method of claim 12, wherein said seed of said plant is a seed capable of producing edible oilseed sprouts.

16. 13. The method of claim 12, wherein the seeds of the plants are seeds capable of producing edible cabbage sprouts.

17. 13. The method of claim 12, wherein the seeds of the plant are seeds capable of producing edible parsley sprouts.

18. 13. The method of claim 12, wherein the seed of the plant is a seed capable of producing edible onion sprouts.

19. 13. The method of claim 12, wherein the seed of the plant is a seed capable of producing an edible vegetable or herb sprout.

20. 13. The method of claim 12, wherein the seed of the plant is a seed capable of producing a crop.

21. 10. The method of claim 9, wherein the seeds are soaked in the aqueous solution for a time sufficient to obtain about 2% to about 20% by weight of their dry weight.

22. 10. The method of claim 9, wherein the seeds are soaked in the aqueous solution for a time sufficient to bring the seeds out of quiescence.

23. 1. A method for inhibiting the growth of a human enteric pathogen in or on a plant, the method comprising spraying the plant with a composition comprising one or more ascarosides.

24. The one or more ascarosides have the structure (I): 【Chemistry 2】 wherein Z is an optionally substituted C2-40 aliphatic group, R ａ and R ｂ Each of is independently —H or —C １－２０ aliphatic, C １－２０ Acyl, C １－２０ Heteroaliphatic, aryl, heteroaryl, hydroxy protecting group, phosphorus-bridged functional group, sulfur-bridged functional group, silicon-bridged functional group, C ２－２０ Carbonate esters (e.g., —C(O)OR ｃ part), C ２－２０ Carbamates (e.g., —C(O)N(R ｃ ) ２ part), C ２－２０ Thioesters (e.g., —C(S)R ｃ part), C ２－２０ Thiocarbonates (e.g., —C(S)OR ｃ part), C ２－２０ Dithiocarbonates (e.g., —C(S)SR ｃ part), C １－２０ Thiocarbamate esters (e.g., —C(S)N(R ｃ ) ２ a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; ｃ is independently, at each occurrence, —H, optionally substituted C １－１２ Aliphatic, optionally substituted C １－１２ is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; R ａ and R ｂ may together form an optionally substituted ring, optionally containing one or more heteroatoms, optionally containing one or more sites of unsaturation.

25. R ａ and R ｂ The method of claim 24, wherein both are —H.

26. Z is, i. -CH(CH ３ )-R １ wherein R １ is an optionally substituted C １－４０ is an 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 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iii. -CH(CH ３ )-(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 an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iv. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH-CO ２ R ３２ where n is an integer from 1 to 40, and R ２ is —H, a metal cation, an optionally substituted C １－２０ an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; v. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-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 an 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 C １－２０ an 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 C １－２０ an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; 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 an 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-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 26. The method of claim 24 or 25, wherein the hydroxyl group is selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

27. 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 26. The method of claim 24 or 25, wherein the amino acid is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

28. 24. The method of claim 23, wherein at least one of the one or more ascarosides is ascr#18.

29. Z is -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CO ２ R ３ where n is an integer from 1 to 40, and R ２ is —H, a metal cation, an optionally substituted C １－２０ 26. The method of claim 24 or 25, wherein the amino acid is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

30. 24. The method of claim 23, wherein at least one of the one or more ascarosides is ascr#7.

31. 24. The method of claim 23, wherein the concentration of the one or more ascarosides in the composition is from about 1 ppb to about 50 ppm.

32. 24. The method of claim 23, wherein the plant is an edible sprout plant.

33. 33. The method of claim 32, wherein the edible sprout plant is an edible legume sprout plant.

34. 33. The method of claim 32, wherein the food sprout plant is a food grain sprout plant.

35. 33. The method of claim 32, wherein the edible sprout plant is an edible oilseed sprout plant.

36. 33. The method of claim 32, wherein the edible sprout plant is an edible cabbage sprout plant.

37. 33. The method of claim 32, wherein the edible sprout plant is an edible parsley sprout plant.

38. 33. The method of claim 32, wherein the edible sprout plant is an edible onion sprout plant.

39. 33. The method of claim 32, wherein the edible sprout plant is an edible vegetable or herb sprout plant.

40. 24. The method of claim 23, wherein the plant is a crop plant.

41. 1. A method for producing edible sprouts, comprising: treating seeds from a plant that can be used to produce edible sprouts by soaking the seeds in an aqueous solution containing one or more ascarosides; placing the treated seeds in a suitable container that will allow sprouts to form from the treated seeds; and harvesting the sprouts after they reach a desired size.

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