Compositions and methods to mitigate phytotoxic effects of agrichemicals

Abstract

This application relates to the use of one or more ascarosides to mitigate the phytotoxic effects of agrichemicals. Various combinations can provide enhanced performance of agrichemicals, with certain combinations surprisingly exhibiting significant reductions in the phytotoxicity of agrichemicals. Various combinations can surprisingly be co-formulated to provide shelf-stable compositions.

Description

[0001] COMPOSITIONS AND METHODS TO MITIGATE PHYTOTOXIC EFFECTS OF AGRICHEMICALS CROSS-REFERENCE TO RELATED APPLICATIONS [1] This application claims the benefit of priority to U.S. Provisional Appl. No.63 / 506,575, filed June 6, 2023, the entirety of which is hereby incorporated by reference. FIELD OF THE INVENTION [2] This application generally relates to agrichemical compounds, compositions and methods of reducing the phytotoxic effects of agrichemicals such as fungicides and insecticides. BACKGROUND OF THE INVENTION [3] Ascaroside natural products are secondary metabolites produced by nematodes. A large number of structurally diverse ascarosides have been identified in nature and the molecules are believed to function as an evolutionarily conserved chemical language used by nematodes to control many aspects of their development. Ascarosides are also perceived by other organisms and have been demonstrated to have a range of effects on numerous organisms including bacteria, fungi, plants, and mammals including humans. Ascarosides hold potential as human medicines, agrichemicals and products for other diverse and valuable applications. [4] Ascaroside treatments have been demonstrated to show efficacy in increasing plant resistance to certain pathogens and / or in inducing and priming plant defense responses (which can inhibit pathogen growth and / or infestation) when applied to the plant. By activating and / or priming plants’ innate defenses, ascarosides can thereby prevent proliferation of pathogens and / or protect crops from the damaging effects caused by diverse pathogens. [5] Plant injury (phytotoxicity) may occur when chemicals are employed to protect plants from pests, fertilize plants, regulate plant growth, etc. This phytotoxicity is highly undesirable because it may retard growth, lower yields and perversely, may leave crops more susceptible to infection or insect damage. It would be desirable if there were simple, cost-effective methods to prevent the phytotoxic effects of agrichemicals. The present invention addresses this and related problems. SUMMARY OF THE INVENTION [6] While ascarosides are known to prime and / or activate plant defenses and thereby provide a useful means to protect plants from pathogens such as fungi and bacteria, there have been no reports that ascaroside treatments can effect non-pathogen stresses to plants. Surprisingly, the present disclosure encompasses the recognition that application of ascarosides to plants can mitigate the phytotoxic effects of other agrichemicals. This disclosure provides compositions and methods to reduce or prevent damage to plants by phytotoxic agents by applying of one or more ascarosides to the plant. 1 409753-013WO (210098) BUSINESS.31545462.1 [7] Phytotoxic effects from agrichemicals may include, but are not limited to: poor germination, especially if a soil drench was used; death of seedlings; death or damage to rapidly growing succulent tissues; stunted or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; and dead areas between the veins of the leaves. [8] In some embodiments, methods are provided herein which include co-application of one or more ascarosides with one or more agrichemicals wherein the one or more agrichemicals have some degree of phytotoxic effects on crops. Provided methods can comprise applying the components within a single formulation (e.g., a liquid formulation) or the one or more ascarosides can be applied separately either before or after application of the one or more agrichemicals. [9] In one aspect, formulations are provided that contain a mixture of one or more ascarosides and one or more agrichemicals. In certain embodiments, such formulations can be advantageously stable for an extended period of time.

[0010] These and other features, aspects, and advantages of the disclosure will be apparent from a reading of the following detailed description together with the accompanying drawings, which are briefly described below. The invention includes any combination of two, three, four, or more of the above-noted embodiments as well as combinations of any two, three, four, or more features or elements set forth in this disclosure, regardless of whether such features or elements are expressly combined in a specific embodiment description herein. This disclosure is intended to be read holistically such that any separable features or elements of the disclosed invention, in any of its various aspects and embodiments, should be viewed as intended to be combinable unless the context clearly dictates otherwise. Other aspects and advantages of the present disclosure will become apparent from the following. BRIEF DESCRIPTION OF THE DRAWINGS

[0011] The present teachings described herein will be more fully understood from the following description of various illustrative embodiments, when read together with the accompanying drawings. It should be understood that each drawing described below is for illustration purposes only and is not intended to limit the scope of the present teachings in any way. The foregoing and other objects, aspects, features, and advantages of the disclosure will become more apparent and may be better understood by referring to the following description taken in conjunction with the accompanying drawings, in which:

[0012] FIG.1 is a chart showing phytotoxicity ratings (0-100%) at 88 days post-emergence measured at a soybean field trial using Blavity™ (a commercial fungicide containing a blend of prothioconazole and Fluxapyroxad). Blavity was applied at label rate two times (45 and 60 days after emergence). Pre- application of ascarosides (Phytalix®) at 15 days before the first Blavity treatment reduced phytotoxic effects of the Blavity applications by more than 20%. 2 409753-013WO (210098) BUSINESS.31545462.1

[0013] FIG.2 is a chart showing phytotoxicity ratings (0-100%) at 95 days post-emergence measured at a soybean field trial using Blavity™ (a commercial fungicide containing a blend of prothioconazole and Fluxapyroxad). Blavity was applied at label rate two times (45 and 60 days after emergence). Pre- application of ascarosides (Phytalix®) at 15 days before the first Blavity treatment reduced phytotoxic effects of the Blavity applications by more than 50%. DEFINITIONS

[0014] In order for the present disclosure to be more readily understood, certain terms are first defined below. Additional definitions for the following terms and other terms are set forth throughout the specification.

[0015] In this application, unless otherwise clear from 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.” In this application, the terms “comprising” and “including” may be understood to encompass itemized components or steps whether presented by themselves or together with one or more additional components or steps. As used in this application, the term “comprise” and variations of the term, such as “comprising” and “comprises,” are not intended to exclude other additives, components, integers or steps.

[0016] As used herein, the terms “about” and “approximately” are used as equivalents. Unless otherwise stated, the terms “about” and “approximately” may be understood to permit standard variation as would be understood by those of ordinary skill in the art. Where ranges are provided herein, the endpoints are included. Any numerals used in this application with or without about / approximately are meant to cover any normal fluctuations appreciated by one of ordinary skill in the relevant art. In some embodiments, the term “approximately” or “about” refers to a range of values that fall 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 (greater than or less than) of the stated reference value unless otherwise stated or otherwise evident from the context (except where such number would exceed 100 % of a possible value).

[0017] Definitions of specific functional groups and chemical terms are described in more detail below. For purposes of this invention, the chemical elements are identified in accordance with the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75thEd., inside cover, and specific functional groups are generally defined as described therein. Additionally, general principles of organic chemistry, as well as specific functional moieties and reactivity, are described in Organic Chemistry, Thomas Sorrell, University Science Books, Sausalito, 1999; Smith and March March’s Advanced Organic Chemistry, 5thEdition, John Wiley & Sons, Inc., New York, 2001; Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989; Carruthers, Some Modern Methods of Organic Synthesis, 3rdEdition, Cambridge University Press, Cambridge, 1987; the entire contents of each of which are incorporated herein by reference. 3 409753-013WO (210098) BUSINESS.31545462.1

[0018] Certain compounds provided herein can comprise one or more asymmetric centers, and thus can exist in various stereoisomeric forms, e.g., enantiomers and / or diastereomers. Thus, inventive compounds and compositions thereof may be in the form of an individual enantiomer, diastereomer or geometric isomer, or may be in the form of a mixture of stereoisomers. In certain embodiments, compounds described herein are enantiopure compounds. In certain other embodiments, mixtures of enantiomers or diastereomers are provided.

[0019] Furthermore, certain compounds as described herein may have one or more double bonds that can exist as either a Z or E isomer, unless otherwise indicated. The compounds can be provided as individual isomers substantially free of other isomers and alternatively, as mixtures of various isomers, e.g., racemic mixtures of enantiomers.

[0020] As used herein, the term “isomers” includes any and all geometric isomers and stereoisomers. For example, “isomers” include 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 falling within the scope of the disclosure. For instance, a compound may, in some embodiments, be provided substantially free of one or more corresponding stereoisomers, and may also be referred to as “stereochemically enriched.”

[0021] Where a particular enantiomer is preferred, it may, in some embodiments be provided substantially free of the opposite enantiomer, and may also be referred to as “optically enriched.” “Optically enriched,” as used herein, means that the compound is made up of a significantly greater proportion of one enantiomer. In certain embodiments the compound is made up of at least about 90% by weight of an 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 an enantiomer. In some embodiments the enantiomeric excess of provided compounds is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9%. In some embodiments, enantiomers may be isolated from racemic mixtures by any method known to those skilled in the art, including chiral high pressure liquid chromatography (HPLC) and the formation and crystallization of chiral salts or prepared by asymmetric syntheses. See, for example, Jacques, et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981); Wilen, S.H., et al., Tetrahedron 33:2725 (1977); Eliel, E.L. Stereochemistry of Carbon Compounds (McGraw–Hill, NY, 1962); Wilen, S.H. Tables of Resolving Agents and Optical Resolutions p.268 (E.L. Eliel, Ed., Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0022] 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).

[0023] The term “aliphatic” or “aliphatic group”, as used herein, denotes a hydrocarbon moiety that may be straight–chain (i.e., unbranched), branched, or cyclic (including fused, bridging, and spiro– fused polycyclic) and may be completely saturated or may contain one or more units of unsaturation, but which is not aromatic. Unless otherwise specified, aliphatic groups contain 1–30 carbon atoms. In certain embodiments, aliphatic groups contain 1–12 carbon atoms. In certain embodiments, 4 409753-013WO (210098) BUSINESS.31545462.1 aliphatic groups contain 1–8 carbon atoms. In certain embodiments, aliphatic groups contain 1–6 carbon atoms. In some embodiments, aliphatic groups contain 1–5 carbon atoms, in some embodiments, aliphatic groups contain 1–4 carbon atoms, in yet other embodiments aliphatic groups contain 1–3 carbon atoms, and in yet other embodiments aliphatic groups contain 1–2 carbon atoms. Suitable aliphatic groups include, but are not limited to, linear or branched, alkyl, alkenyl, and alkynyl groups, and hybrids thereof such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl or (cycloalkyl)alkenyl.

[0024] The term “heteroaliphatic” or “heteroaliphatic group”, as used herein, denotes an aliphatic group where one or more carbon or hydrogen atoms are replaced by a heteroatom (e.g. oxygen, nitrogen, sulfur, phosphorous, boron, etc.). In some embodiments, a heteroaliphatic group is a heterocyclyl group.

[0025] The term "unsaturated", as used herein, means that a moiety has one or more double or triple bonds.

[0026] The term “alkyl,” as used herein, refers to saturated, straight– or branched–chain hydrocarbon radicals derived from an aliphatic moiety containing between one and six carbon atoms by removal of a single hydrogen atom. Unless otherwise specified, alkyl groups contain 1–12 carbon atoms. In certain embodiments, alkyl groups contain 1–8 carbon atoms. In certain embodiments, alkyl groups contain 1–6 carbon atoms. In some embodiments, alkyl groups contain 1–5 carbon atoms, in some embodiments, alkyl groups contain 1–4 carbon atoms, in yet other embodiments alkyl groups contain 1–3 carbon atoms, and in yet other embodiments alkyl groups contain 1–2 carbon atoms. Examples of alkyl radicals include, but are not limited to, methyl, ethyl, n–propyl, isopropyl, n–butyl, iso–butyl, sec–butyl, sec–pentyl, iso–pentyl, tert–butyl, n–pentyl, neopentyl, n–hexyl, sec–hexyl, n–heptyl, n– octyl, n–decyl, n–undecyl, dodecyl, and the like.

[0027] The term “alkenyl,” as used herein, denotes a monovalent group derived from a straight– or branched–chain aliphatic moiety having at least one carbon–carbon double bond by the removal of a single hydrogen atom. Unless otherwise specified, alkenyl groups contain 2–12 carbon atoms. In certain embodiments, alkenyl groups contain 2–8 carbon atoms. In certain embodiments, alkenyl groups contain 2–6 carbon atoms. In some embodiments, alkenyl groups contain 2–5 carbon atoms, in some embodiments, alkenyl groups contain 2–4 carbon atoms, in yet other embodiments alkenyl groups contain 2–3 carbon atoms, and in yet other embodiments alkenyl groups contain 2 carbon atoms. Alkenyl groups include, for example, ethenyl, propenyl, butenyl, 1–methyl–2–buten–1–yl, and the like.

[0028] The term “aryl” used alone or as part of a larger moiety as in “aralkyl”, “aralkoxy”, or “aryloxyalkyl”, refers to monocyclic and polycyclic ring systems having a total of five to 20 ring members, wherein at least one ring in the system is aromatic and wherein each ring in the system contains three to twelve ring members. The term “aryl” may be used interchangeably with the term “aryl ring”. In certain embodiments, “aryl” refers to an aromatic ring system which includes, but is 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 it is used herein, is a group in which 5 409753-013WO (210098) BUSINESS.31545462.1 an aromatic ring is fused to one or more additional rings, such as benzofuranyl, indanyl, phthalimidyl, naphthimidyl, phenantriidinyl, or tetrahydronaphthyl, and the like.

[0029] The terms “heteroaryl” and “heteroar–,” used alone or as part of a larger moiety, e.g., “heteroaralkyl,” or “heteroaralkoxy,” refer to groups having 5 to 10 ring atoms, preferably 5, 6, or 9 ring atoms; having 6, 10, or 14 π electrons shared in a cyclic array; and having, in addition to carbon atoms, from one to five heteroatoms. The term “heteroatom” refers to nitrogen, oxygen, or sulfur, and includes any oxidized form of nitrogen or sulfur, and any quaternized form of a basic nitrogen. Heteroaryl groups include, without limitation, thienyl, furanyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolizinyl, purinyl, naphthyridinyl, and pteridinyl. The terms “heteroaryl” and “heteroar–”, as used herein, also include groups in which a heteroaromatic ring is fused to one or more aryl, cycloaliphatic, or heterocyclyl rings, where the radical or point of attachment is on the heteroaromatic ring. Nonlimiting examples include indolyl, isoindolyl, benzothienyl, benzofuranyl, dibenzofuranyl, indazolyl, benzimidazolyl, benzthiazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 4H–quinolizinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, and pyrido[2,3–b]–1,4–oxazin–3(4H)–one. A heteroaryl group may be monocyclic, bicyclic, bridged bicyclic, or spirocyclic. The term “heteroaryl” may be used interchangeably with the terms “heteroaryl ring,” “heteroaryl group,” or “heteroaromatic,” any of which terms include rings that are optionally substituted. The term “heteroaralkyl” refers to an alkyl group substituted by a heteroaryl, wherein the alkyl and heteroaryl portions independently are optionally substituted. The term “heteroarylenyl” refers to bivalent heteroaryl groups (e.g., pyridylenyl).

[0030] As used herein, the terms “heterocycle,” “heterocyclyl,” “heterocyclic radical,” and “heterocyclic ring” are used interchangeably and refer to a stable 5– to 7–membered monocyclic or 7– 10–membered bicyclic heterocyclic moiety that is either saturated or partially unsaturated, and having, in addition to carbon atoms, one or more, preferably one to four, heteroatoms, as defined above. When used in reference to a ring atom of a heterocycle, the term "nitrogen" includes a substituted nitrogen. As an example, in a saturated or partially unsaturated ring having 0–3 heteroatoms selected from oxygen, sulfur or nitrogen, the nitrogen may be N (as in 3,4–dihydro–2H– pyrrolyl), NH (as in pyrrolidinyl), or +NR (as in N–substituted pyrrolidinyl).

[0031] A heterocyclic ring can be attached to its pendant group at any heteroatom or carbon atom that results in a stable structure and any of the ring atoms can be optionally substituted. Examples of such saturated or partially unsaturated heterocyclic radicals include, without limitation, tetrahydrofuranyl, tetrahydrothiophenyl pyrrolidinyl, piperidinyl, pyrrolinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl, oxazolidinyl, piperazinyl, dioxanyl, dioxolanyl, diazepinyl, oxazepinyl, thiazepinyl, morpholinyl, and quinuclidinyl. The terms “heterocycle,” “heterocyclyl,” “heterocyclyl ring,” “heterocyclic group,” “heterocyclic moiety,” and “heterocyclic radical,” are used interchangeably herein, and also include groups in which a heterocyclyl ring is 6 409753-013WO (210098) BUSINESS.31545462.1 fused to one or more aryl, heteroaryl, or cycloaliphatic rings, such as indolinyl, 3H–indolyl, chromanyl, phenanthridinyl, or tetrahydroquinolinyl. In some embodiments, a heterocyclic ring may be a 5-12 membered bicyclic, bridged bicyclic, or spirocyclic ring. A heterocyclic ring may include one or more oxo (=O) or thioxo (=S) substituent. The term “heterocyclylalkyl” refers to an alkyl group substituted by a heterocyclyl, wherein the alkyl and heterocyclyl portions independently are optionally substituted.

[0032] As used herein, the term “partially unsaturated” refers to a ring moiety that includes at least one double or triple bond. The term “partially unsaturated” is intended to encompass rings having multiple sites of unsaturation, but is not intended to include aryl or heteroaryl moieties, as herein defined.

[0033] As described herein, compounds as provided herein 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 designated moiety are replaced with a suitable substituent. Unless otherwise indicated, 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 substituent may be either the same or different at every position. Combinations of substituents envisioned are preferably those that result in the formation of stable or chemically feasible compounds. The term “stable,” as used herein, refers to compounds that are not substantially altered when subjected to conditions to allow for their production, detection, and, in certain embodiments, their recovery, purification, and use for one or more of the purposes disclosed herein.

[0034] Suitable monovalent substituents on a substitutable carbon atom of an “optionally substituted” group are independently halogen; –(CH2)0–4R ^; –(CH2)0–4OR ^; -O-(CH2)0-4C(O)OR°; –(CH2)0– 4CH(OR ^)2; –(CH2)0–4SR ^; –(CH2)0–4Ph, which may be substituted with R°; –(CH2)0–4O(CH2)0–1Ph which may be substituted with R°; –CH=CHPh, which may be substituted with R°; –NO2; –CN; –N3; –(CH2)0–4N(R ^)2; –(CH2)0–4N(R ^)C(O)R ^; –N(R ^)C(S)R ^; –(CH2)0-4N(R ^)C(O)NR ^2; – N(R ^)C(S)NR ^2; –(CH2)0–4N(R ^)C(O)OR ^; -N(R ^)N(R ^)C(O)R ^; –N(R ^)N(R ^)C(O)NR ^2; – N(R ^)N(R ^)C(O)OR ^; –(CH2)0–4C(O)R ^; -C(S)R ^; –(CH2)0–4C(O)OR ^; –(CH2)0–4C(O)N(R ^)2; – (CH2)0–4C(O)SR ^; –(CH2)0–4C(O)OSiR ^3; –(CH2)0–4OC(O)R ^; –OC(O)(CH2)0–4SR–, SC(S)SR°; – (CH2)0–4SC(O)R ^; –(CH2)0–4C(O)NR ^2; -C(S)NR ^2; –C(S)SR°; –SC(S)SR°, –(CH2)0–4OC(O)NR ^2; – C(O)N(OR ^)R ^; –C(O)C(O)R ^; -C(O)CH2C(O)R ^; –C(NOR ^)R ^; –(CH2)0–4SSR ^; –(CH2)0–4S(O)2R ^; –(CH2)0–4S(O)2OR ^; -(CH2)0–4OS(O)2R ^; –S(O)2NR ^2; –(CH2)0–4S(O)R ^; –N(R ^)S(O)2NR ^2; – N(R ^)S(O)2R ^; -N(OR ^)R ^; –C(NH)NR ^2; –P(O)2R ^; –P(O)R ^2; –OP(O)R ^2; –OP(O)(OR ^)2; SiR ^3; – (C1–4straight or branched alkylene)O–N(R ^)2; or –(C1–4straight or branched alkylene)C(O)O–N(R ^)2, wherein each R ^ may be substituted as defined below and is independently hydrogen, C1-8aliphatic, – CH2Ph, –O(CH2)0–1Ph, or a 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or, notwithstanding the 7 409753-013WO (210098) BUSINESS.31545462.1 definition above, two independent occurrences of R ^, taken together with their intervening atom(s), form a 3–12–membered saturated, partially unsaturated, or aryl mono– or polycyclic ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, which may be substituted as defined below.

[0035] Suitable monovalent substituents on R ^ (or the ring formed by taking two independent occurrences of R ^ together with their intervening atoms), are independently halogen, –(CH2)0–2R^, – (haloR^), –(CH2)0–2OH, –(CH2)0–2OR^, –(CH2)0–2CH(OR^)2; -O(haloR^), –CN, –N3, –(CH2)0– 2C(O)R^, –(CH2)0–2C(O)OH, –(CH2)0–2C(O)OR^, -(CH2)0-4C(O)N(R ^)2; –(CH2)0–2SR^, –(CH2)0–2SH, –(CH2)0–2NH2, –(CH2)0–2NHR^, -(CH2)0-2NR^2, –NO2, –SiR^3, –OSiR^3, –C(O)SR^,–(C1–4straight or branched alkylene)C(O)OR^, or –SSR^wherein each R^is unsubstituted or where preceded by “halo” is substituted only with one or more halogens, and is independently selected from C1–4 aliphatic, -CH2Ph, –O(CH2)0–1Ph, or a 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents on a saturated carbon atom of R ^ include =O and =S.

[0036] 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)2R*, =NR*, =NOR*, –O(C(R*2))2–3O–, or –S(C(R*2))2–3S–, wherein each independent occurrence of R*is selected from hydrogen, C1–6 aliphatic which may be substituted as defined below, or an unsubstituted 5–6– membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents that are bound to vicinal substitutable carbons of an “optionally substituted” group include: –O(CR*2)2–3O–, wherein each independent occurrence of R*is selected from hydrogen, C1–6aliphatic which may be substituted as defined below, or an unsubstituted 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0037] Suitable substituents on the aliphatic group of R*include halogen, –R^, -(haloR^), –OH, – OR^, –O(haloR^), –CN, –C(O)OH, –C(O)OR^, –NH2, –NHR^, –NR^2, or –NO2, wherein each R^is unsubstituted or where preceded by “halo” is substituted only with one or more halogens, and is independently C1–4aliphatic, –CH2Ph, –O(CH2)0–1Ph, or a 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0038] 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)CH2C(O)R†, –S(O)2R†, -S(O)2NR†2, – C(S)NR†2, –C(NH)NR†2, or –N(R†)S(O)2R†; wherein each R†is independently hydrogen, C1–6aliphatic which may be substituted as defined below, unsubstituted –OPh, or an unsubstituted 5–6– membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or, notwithstanding the definition above, two independent occurrences of R†, taken together with their intervening atom(s) form an unsubstituted 3–12– 8 409753-013WO (210098) BUSINESS.31545462.1 membered saturated, partially unsaturated, or aryl mono– or bicyclic ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0039] Suitable substituents on the aliphatic group of R†are independently halogen, –R^, –(haloR^), –OH, –OR^, –O(haloR^), –CN, –C(O)OH, –C(O)OR^, –NH2, –NHR^, –NR^2, or -NO2, wherein each R^is unsubstituted or where preceded by “halo” is substituted only with one or more halogens, and is independently C1–4 aliphatic, –CH2Ph, –O(CH2)0–1Ph, or a 5-6-membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0040] As used herein, the term “substantially” refers to the qualitative condition of exhibiting total or near-total extent or degree of a characteristic or property of interest.

[0041] The convention of naming ascarosides by a several-letter prefix followed by a pound sign (#) and a number is sometimes used (for example ascr#18). This convention is used in the scientific literature and the skilled artisan will understand that each such name is associated with a specific chemical structure of known composition and will readily apprehend the structure of the molecule referred to using this naming convention. Unless otherwise indicated, all compound identifiers of this format used herein conform to the definitions described in the C. elegans Small Molecule Identifier Database (SMID-DB) maintained at www.smid-db.org / .

[0042] The term “pathogen” refers to any bacterium, fungus, oomecyte, virus, nematode (e.g., cyst or root knot nematode) or insect with pathogenic effects on a plant. DETAILED DESCRIPTION OF THE INVENTION

[0043] Compositions and methods for mitigating the phytotoxic effects of agrichemicals on plants are provided. The disclosure is directed to the treatment of plants with one or more ascarosides to prevent or lessen the phytotoxic effects of agrichemicals such as fungicides, antimicrobials, insecticides, nutrient compositions, herbicides, and other components of agrichemical formulations such as solvents, additives, adjuvants, and the like known to have phytotoxicity.

[0044] In one aspect, the present disclosure provides methods of treating a plant with an ascaroside to reduce the phytotoxic effects of an agrichemical.

[0045] In another aspect, the present disclosure provides compositions comprising an ascaroside, useful for treating plants to reduce the phytotoxic effects of agrichemicals.

[0046] Before more fully describing these methods and compositions, the ascarosides will be more fully described. Ascarosides

[0047] Ascarosides are derivatives of the sugar ascarylose—a di-deoxy sugar lacking hydroxyl groups at its 3- and 6-positions. Ascarosides have the general structure shown in Formula I: 9 409753-013WO (210098) BUSINESS.31545462.1 OZ (Formula I), wherein: Z is an optionally substituted C2-40 aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20 aliphatic, C1-20 acyl, C1-20 heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group, a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g., -a moiety -C(O)ORc), a C2-20carbamate (e.g., -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g., a moiety -C(S)Rc), a C2-20thiocarbonate (e.g., a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g., a moiety -C(S)SRc), a C1-20thiocarbamate (e.g., a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, where each Rcis independently at each occurrence selected from -H, optionally substituted C1-12 aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

[0048] In certain embodiments, Z is: (i) –CH(CH3)–R1, where R1is an optionally substituted C1-40 aliphatic group; (ii) –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (iii) –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (iv) –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1- 20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted 10 409753-013WO (210098) BUSINESS.31545462.1 heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (v) –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (vi) –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; (vii) –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (viii) –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; or (ix) –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule.

[0049] In certain embodiments, Z is: (x) –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xi) –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally 11 409753-013WO (210098) BUSINESS.31545462.1 substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xii) –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiii) –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiv) –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xv) –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvi) –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvii) –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; or (xviii) an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising a nitrogen-, oxygen- or sulfur-containing functional group. 12 409753-013WO (210098) BUSINESS.31545462.1

[0050] As defined above and described herein, in some embodiments, Z comprises a nitrogen-, oxygen-, or sulfur-containing functional group. It will be appreciated that “an oxygen-containing functional group” refers to moieties that comprise one or more oxygen atoms (e.g., carbonyl-containing groups such as esters, aldehydes, carboxylic acids, and ketones; ethers, hydroxyls, and heterocyclic rings comprising one or more oxygen atoms and / or one of the foregoing functional groups); “a nitrogen- containing functional group” refers to moieties that comprise one or more nitrogen atoms (e.g., amines, amides, carbamates, imines, ureas, oximes, amidines, guanidines, nitriles, azo groups, azides, and heterocyclic rings comprising one or more nitrogen atoms and / or one of the foregoing functional groups); and “a sulfur-containing functional group” refers to moieties that comprise one or more sulfur atoms (e.g., thioether, sulfone, sulfonic acid, sulfoxide, thiol, thiocyanate, or disulfide).

[0051] In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising an oxygen-containing functional group. In certain embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising a carboxylic acid. In certain embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising an aldehyde. In certain embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising an ester. In some embodiments, Z an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising -CO2R2. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising -CO2H. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising -CO2CH3. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising -CON(R3)2. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising -N(R3)2. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising an ester comprising a linker moiety covalently attached to one or more additional ascaroside molecules.

[0052] As described above, the ascarylose sugar moiety in the provided compounds can be substituted or unsubstituted (i.e., there can be functional groups other than -OH at 2- and 4- positions of the sugar or, stated differently, variables Raand / or Rbcan be other than -H in any of the formulae herein).

[0053] As defined above and described herein, each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group, a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g., -a moiety -C(O)ORc), a C2-20 carbamate (e.g., -a moiety -C(O)N(Rc)2), a C2-20 thioester (e.g. a moiety -C(S)Rc), a C2-20 thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20 dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20 thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon- containing linker moiety to an ascaroside molecule. 13 409753-013WO (210098) BUSINESS.31545462.1

[0054] In certain embodiments, Rais -H. In certain embodiments, Rbis -H. In certain embodiments, Raand Rbare the same. In certain embodiments Raand Rbare both -H. In certain embodiments, Raand Rbare different. In certain embodiments, Rais -H, and Rbis other than -H. In certain embodiments, Rais other than -H and Rbis -H. In certain embodiments, Rais -H and Rbis p-hydroxybenzoate. In certain embodiments, Rais -H and Rbis indole-3-carboxylate. In certain embodiments, Rais -H and Rbis (E)- 2-methyl-2-butenoate. In certain embodiments, Rais -H and Rbis picolinate. In certain embodiments, Rais -H and Rbis nicotinate. In certain embodiments, Rais -H and Rbis (R)-2-hydroxy-2-(4- hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, Rais -H and Rbis 4-((4- hydroxyphenethyl)amino)-4-oxobutanoate. In certain embodiments, Racomprises a glycoside, amino acid, a peptide, or nucleotide. In certain embodiments, Rbcomprises a glycoside, amino acid, a peptide, or nucleotide. In certain embodiments, Racomprises a linkage to a second ascaroside molecule. In certain embodiments, Rbcomprises a linkage to an ascaroside molecule. In certain embodiments, Racomprises a sugar. In certain embodiments, Rbcomprises a sugar.

[0055] In some embodiments, Rais an optionally substituted C1-20aliphatic. In some embodiments, Rais an optionally substituted C1-6aliphatic. In some embodiments, Rais C1-20aliphatic. In some embodiments, Rais C1-6aliphatic. In some embodiments, Rais methyl, ethyl, n-propyl, iso-propyl, n- butyl, isobutyl, sec-butyl, or t-butyl. In some embodiments, Rais C1-20 acyl. In some embodiments, Rais -C(O)Rc. In some embodiments, Rais -C(O)H. In some embodiments, Rais -C(O)CH3. In some embodiments, Rais an optionally substituted C1-20 heteroaliphatic. In some embodiments, Rais an optionally substituted C1-6heteroaliphatic. In some embodiments, Rais C1-20heteroaliphatic. In some embodiments, Rais C1-6heteroaliphatic. In some embodiments, Rais an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais optionally substituted aryl. In some embodiments, Rais optionally substituted phenyl. In some embodiments, Rais phenyl. In some embodiments, Rais an optionally substituted heteroaryl group. In some embodiments, Rais an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais an optionally substituted C2-20 carbonate. In some embodiments, Rais -C(O)ORc. In some embodiments, Rais an optionally substituted C2-20 carbamate. In some embodiments, Rais -C(O)N(Rc)2. In some embodiments, Rais an optionally substituted C2-20thioester. In some embodiments, Rais -C(S)Rc. In some embodiments, Rais an optionally substituted C2-20 thiocarbonate. In some embodiments, Rais -C(S)ORc. In some embodiments, Rais an optionally substituted C2-20 dithiocarbonate. In some embodiments, Rais -C(S)SRc. In some embodiments, Rais an optionally substituted C1-20 thiocarbamate. In some embodiments, Rais -C(S)N(Rc)2. 14 409753-013WO (210098) BUSINESS.31545462.1

[0056] In some embodiments, Rais an optionally substituted hydroxyl protecting group. Suitable hydroxyl protecting groups are well known in the art and include those described in detail in Protecting Groups in Organic Synthesis, T. W. Greene and P. G. M. Wuts, 3rdedition, John Wiley & Sons, 1999. Examples of suitable oxygen protecting groups include, but are not limited to, acetyl, benzoyl benzyl, β-methoxyethoxymethyl ether (MEM), dimethoxytrityl (DMT), methoxymethyl ether (MOM), methoxytrityl (MMT), p-methoxybenzyl ether (PMB), methylthiomethyl ether, pivaloyl, tetrahydropyranyl (THP), tetrahydrofuran (THF), trityl, silyl ethers (e.g., trimethylsilyl (TMS), tert- butyldimethylsilyl (TBDMS), tri-iso-propylsilyloxymethyl (TOM), and triisopropylsilyl (TIPS) ethers), methyl ethers, and ethoxyethyl ethers. In some embodiments, Rais -ORc.

[0057] In some embodiments, Rais an optionally substituted phosphorous-linked functional group. It will be appreciated that “phosphorous-linked functional group” as used herein refers to moieties that comprise one or more phosphorous atoms (e.g., phosphine, phosphodiester, phosphonic acid, phosphate). In some embodiments, Rais an optionally substituted sulfur-linked functional group. It will be appreciated that “sulfur-linked functional group” as used herein refers to moieties that comprise one or more sulfur atoms (e.g., thioether, sulfone, sulfonic acid, sulfoxide, thiol, thiocyanate, or disulfide). In some embodiments, Rais an optionally substituted silicon-linked functional group. It will be appreciated that “silicon-linked functional group” as used herein refers to moieties that comprise one or more silicon atoms (e.g., silanol, suloxides, siloxanes, silyl ethers, silyl chlorides, silyl hydrides, silenes, or siloles).

[0058] In some embodiments, Rais an optionally substituted sugar moiety. In some embodiments, Rais an optionally substituted peptide. In some embodiments, Rais an optionally substituted polymer chain. In some embodiments, Rais a linkage via a bond or a carbon-containing linker moiety to an ascaroside molecule. In some embodiments, Rais an optionally substituted C1-6 aliphatic or heteroaliphatic comprising an ascaroside.

[0059] In some embodiments, Rbis an optionally substituted C1-20aliphatic. In some embodiments, Rbis an optionally substituted C1-6aliphatic. In some embodiments, Rbis C1-20aliphatic. In some embodiments, Rbis C1-6aliphatic. In some embodiments, Rbis methyl, ethyl, n-propyl, iso-propyl, n- butyl, isobutyl, sec-butyl, or t-butyl. In some embodiments, Rbis C1-20 acyl. In some embodiments, Rbis -C(O)Rc. In some embodiments, Rbis -C(O)H. In some embodiments, Rbis -C(O)CH3. In some embodiments, Rbis an optionally substituted C1-20 heteroaliphatic. In some embodiments, Rbis an optionally substituted C1-6heteroaliphatic. In some embodiments, Rbis C1-20heteroaliphatic. In some embodiments, Rbis C1-6heteroaliphatic. In some embodiments, Rbis an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis optionally substituted aryl. In some embodiments, Rbis optionally substituted phenyl. In some embodiments, Rbis phenyl. In some embodiments, Rbis an optionally substituted heteroaryl group. In some 15 409753-013WO (210098) BUSINESS.31545462.1 embodiments, Rbis an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis an optionally substituted C2-20carbonate. In some embodiments, Rbis -C(O)ORc. In some embodiments, Rbis an optionally substituted C2-20carbamate. In some embodiments, Rbis -C(O)N(Rc)2. In some embodiments, Rbis an optionally substituted C2-20thioester. In some embodiments, Rbis -C(S)Rc. In some embodiments, Rbis an optionally substituted C2-20 thiocarbonate. In some embodiments, Rbis -C(S)ORc. In some embodiments, Rbis an optionally substituted C2-20 dithiocarbonate. In some embodiments, Rbis -C(S)SRc. In some embodiments, Rais an optionally substituted C1-20thiocarbamate. In some embodiments, Rbis -C(S)N(Rc)2.

[0060] In some embodiments, Rbis an optionally substituted hydroxyl protecting group.

[0061] In some embodiments, Rbis an optionally substituted phosphorous-linked functional group. In some embodiments, Rbis an optionally substituted sulfur-linked functional group. In some embodiments, Rbis an optionally substituted silicon-linked functional group.

[0062] In some embodiments, Rbis an optionally substituted sugar moiety. In some embodiments, Rais an optionally substituted peptide. In some embodiments, Rbis an optionally substituted polymer chain. In some embodiments, Rbis a linkage via a bond or a carbon-containing linker moiety to an ascaroside molecule. In some embodiments, Rbis an optionally substituted C1-6 aliphatic or heteroaliphatic comprising an ascaroside.

[0063] In some embodiments, Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation. In some embodiments, Raand Rbmay be taken together to form an optionally substituted 3- to 12- membered monocyclic or bicyclic saturated or partially unsaturated carbocyclyl or heterocyclyl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Raand Rbmay be taken together to form an optionally substituted 5- to 12- membered monocyclic or bicyclic aryl or heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0064] As defined above and described herein, each Rcis independently at each occurrence selected from -H, optionally substituted C1-12 aliphatic, optionally substituted C1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule.

[0065] In some embodiments, Rcis independently at each occurrence selected from -H, optionally substituted C1-12 aliphatic, optionally substituted C1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl.

[0066] In some embodiments, an occurrence of Rcis -H. In some embodiments, Rcis an optionally substituted C1-12aliphatic group. In some embodiments, Rcis an optionally substituted C1-6aliphatic group. In some embodiments, Rcis an optionally substituted C1-12 heteroaliphatic group. In some embodiments, Rcis an optionally substituted C1-6 heteroaliphatic group. In some embodiments, Rcis 16 409753-013WO (210098) BUSINESS.31545462.1 an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rcis an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rcis an optionally substituted aryl group. In some embodiments, Rcis optionally substituted phenyl. In some embodiments, Rcis phenyl. In some embodiments, Rcis an optionally substituted heteroaryl group. In some embodiments, Rcis an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rcis an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0067] As defined above and described herein, R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. In some embodiments, R2is -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, or an optionally substituted heteroaryl group.

[0068] In some embodiments, R2is -H. In some embodiments, R2is a metal cation. In some embodiments, R2is an optionally substituted C1-20 aliphatic group. In some embodiments, R2is an optionally substituted C1-6aliphatic group. In some embodiments, R2is an optionally substituted C1-20heteroaliphatic group. In some embodiments, R2is an optionally substituted C1-6heteroaliphatic group. In some embodiments, R2is an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R2is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R2is an optionally substituted aromatic group. In some embodiments, R2is optionally substituted phenyl. In some embodiments, R2is phenyl. In some embodiments, R2is an optionally substituted heteroaryl group. In some embodiments, R2is an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R2is an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0069] In some embodiments, R2is a glycoside. It will be appreciated that a glycoside refers to a moiety comprising a sugar bound to another functional group via a glycosidic bond.

[0070] In some embodiments, R2is nucleotide. In some embodiments, R2is adenosine monophosphate, cytidine monophosphate, guanosine monophosphate, or uridine monophosphate. In some embodiments, R2is deoxyadenosine monophosphate, deoxycytidine monophosphate, deoxyguanosine monophosphate, or deoxythymidine monophosphate. 17 409753-013WO (210098) BUSINESS.31545462.1

[0071] In some embodiments, R2is a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. In some embodiments, R2is an optionally substituted C1-6 aliphatic or heteroaliphatic comprising an ascaroside.

[0072] As defined above and described herein, each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, or a linkage via a bond or a containing linker moiety to another ascaroside molecule. In some embodiments, each R3is independently selected from -H and C1-8aliphatic. In some embodiments, one R3is -H and the other R3is other than -H. In some embodiments, neither R3is -H. In some embodiments, each R3is -H. In some embodiments, an occurrence of R3is an optionally substituted C1-20 aliphatic group. In some embodiments, an occurrence of R3is an optionally substituted C1-6 aliphatic group. In some embodiments, an occurrence of R3is an optionally substituted C1-20 group. In some embodiments, an occurrence of R3is an optionally substituted C1-6 group. In some embodiments, R3is an optionally substituted 3- and 8- saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently nitrogen, oxygen, or sulfur. In some embodiments, R3is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, occurrence of R3is an optionally substituted aryl group. In some embodiments, R3is optionally substituted phenyl. In some embodiments, R3is phenyl. In some embodiments, R3is an optionally substituted heteroaryl group. In some embodiments, R3is an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R3is an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0073] In certain embodiments, Raand Rbare the same. In certain embodiments Raand Rbare both - H.

[0074] In certain embodiments, Raand Rbare different. In certain embodiments, Rais -H, and Rbis other than -H. In certain embodiments, Rais other than -H and Rbis -H. In certain embodiments, Rais -H and Rbis p-hydroxybenzoate. In certain embodiments, Rais -H and Rbis indole-3-carboxylate. In certain embodiments, Rais -H and Rbis (E)-2-methyl-2-butenoate. In certain embodiments, Rais -H and Rbis picolinate. In certain embodiments, Rais -H and Rbis nicotinate. In certain embodiments, Rais -H and Rbis (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, Rais -H and Rbis 4-((4-hydroxyphenethyl)amino)-4-oxobutanoate.

[0075] In certain embodiments Raand Rbare both -H, and Z is selected from the formulae defined in (i) to (xviii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (i) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (ii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (iii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (iv) above. In certain embodiments Raand Rbare both 18 409753-013WO (210098) BUSINESS.31545462.1 -H, and Z conforms to formula (v) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (vi) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (vii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (viii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (ix) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (x) above. In certain embodiments Raand Rbare both - H, and Z conforms to formula (xi) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xiii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xiv) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xv) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xvi) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xvii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xviii) above.

[0076] In certain embodiments, R2is -H. In certain embodiments, R2is a metal cation. In certain embodiments, R2is an organic cation (e.g., a nitrogen- or phosphorous-centered cationic group). In certain embodiments, R2is an optionally substituted C1-20aliphatic group. In certain embodiments, R2is an optionally substituted C1-12aliphatic group. In certain embodiments, R2is an optionally substituted C1-8aliphatic group. In certain embodiments, R2is an optionally substituted C1-6aliphatic group. In certain embodiments, R2is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t- butyl. In certain embodiments, R2is an optionally substituted aromatic group. In certain embodiments, R2is a glycoside. In certain embodiments, R2comprises an amino acid. In certain embodiments, R2comprises a peptide. In certain embodiments, R2comprises a nucleotide.

[0077] In certain embodiments, at least one R3is -H. In certain embodiments, both R3groups are -H. In certain embodiments, at least one R3is an optionally substituted C1-20 aliphatic group. In certain embodiments, both R3groups are an optionally substituted C1-20 aliphatic group which may be the same or different. In certain embodiments, at least one R3is an optionally substituted C1-12 aliphatic group. In certain embodiments, at least one R3is an optionally substituted C1-8 aliphatic group. In certain embodiments, at least one R3is an optionally substituted C1-6aliphatic group. In certain embodiments, at least one R3is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In certain embodiments, at least one R3is -CH2CH2OH. In certain embodiments, at least one R3is - CH2CH2OR2, where R2is as defined in the genera and subgenera herein. In certain embodiments, at least one R3is an optionally substituted aromatic group. In certain embodiments, at least one R3comprises a glycoside. In certain embodiments, at least one R3comprises an amino acid. In certain embodiments, at least one R3at least one R3comprises a peptide. In certain embodiments, at least one R3comprises a nucleotide.

[0078] In certain embodiments, an ascaroside is selected from the group consisting of: CO R CO R CO R CO , 409753-013WO (210098) BUSINESS.31545462.1 where x is an integer from 1 to 22, and each of Ra, Rb, and R2is as defined above and in the genera and subgenera herein.

[0079] In certain embodiments, an ascaroside is selected from the group consisting of: COH COH C COH O O OH O O O O RO O , where

[0080] an group COR O COR COR O COR O O , and

[0081] In certain embodiments, an ascaroside is selected from the group consisting of: COH O COH CO COH O H O O ,

[0082] In certain embodiments, an ascaroside is selected from the group consisting of: COR COR CO COR O O R O O , subgenera herein.

[0083] In certain embodiments, an ascaroside is selected from the group consisting of: CO2H CO2H CO2H CO2H O O O x ,

[0084] In certain embodiments, an ascaroside is selected from the group consisting of: COR COR COR ,

[0085] In certain embodiments, an ascaroside is selected from the group consisting of: 20 409753-013WO (210098) BUSINESS.31545462.1 CO H O CO H CO CO H O H O O HO O , , where genera and subgenera herein.

[0087] In certain embodiments, an ascaroside is selected from the group consisting of: where

[0088] In certain embodiments, an ascaroside is selected from the group consisting of: , and subgenera herein.

[0089] In certain embodiments, an ascaroside is selected from the group consisting of: where each of y and R3is as defined above and in the genera and subgenera herein.

[0090] In an embodiment, ascarosides useful in the context of the present disclosure have the general structure (I), where Z is –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide, and can be used for inhibiting human pathogenic bacterial growth in or on a plant. 21 409753-013WO (210098) BUSINESS.31545462.1

[0091] In an embodiment, ascarosides useful in the context of the present disclosure have the general structure (I) where Z is –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0092] Specific ascarosides that are useful in the context of the present disclosure include, but are not limited to, ascr#7 and ascr#18. O group ascr#20, ascr#22, ascr#24, ascr#26, ascr#28, ascr#30, ascr#32, ascr#34, and ascr#36. In certain embodiments, an 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, an ascaroside used in the provided methods is selected from the group consisting of: ascr#9, ascr#14, ascr#10, and ascr#18.

[0094] In certain embodiments, an ascaroside used in the provided methods and compositions is selected from the group consisting of: ascr#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, an 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, an 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, an ascaroside used in the provided methods is selected from the group consisting of: oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

[0095] In certain embodiments, an ascaroside used in the provided methods and compositions is selected from the group consisting of: bhas#9, bhas#10, bhas#16, bhas#18, bhas#22, bhas#24, bhas#26, bhas#28, bhas#30, bhas#32, bhas#34, bhas#36, bhas#38, bhas#40, and bhas#42.

[0096] In certain embodiments, an ascaroside used in the provided methods and compositions is selected from the group consisting of: bhos#10, bhos#16, bhos#18, bhos#22, bhos#24, bhos#26, bhos#28, bhos#30, bhos#32, bhos#34, bhos#36, bhos#38, bhos#40, and bhos#42.

[0097] In certain embodiments, an ascaroside used in the provided methods and compositions is selected from the group consisting of: ascr#18, oscr#16, oscr#17, oscr#15, bhas#18, bhos#16, glas#18, dhas#18, ibha#18, ibho#16, icas#18, icos#15, icos#16, and any combination of two or more of these.

[0098] In some embodiments, an ascaroside used in the provided methods and compositions is an ascaroside salt as disclosed in international publication number WO2023 / 220174, filed May 10, 2023 or an ascaroside modified to provide for extended release of the active ingredient as disclosed in 22 409753-013WO (210098) BUSINESS.31545462.1 international publication number WO2023 / 212362, filed April 28, 2023, both of which are incorporated by reference herein in their entireties.

[0099] Ascarosides can be obtained from natural sources (e.g., nematodes) or they may be prepared synthetically. Ascarosides can be prepared synthetically, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascarylose. An exemplary method of preparing ascarosides includes: providing as a feedstock a 1-O-substituted rhamnose; forming a mono-sulfonate ester at the 3-OH group of the feedstock; and treating the mono-sulfonate ester with a hydride source to form a 1-O-substituted ascarylose. In certain embodiments, forming the mono-sulfonate ester is conducted on a substrate without hydroxyl protecting groups at the 2- or 4-position of the rhamnose feedstock. In certain embodiments, such methods comprise contacting the feedstock 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 Publication No. WO / 2022 / 024067, which is incorporated herein by reference. Methods

[0100] In one aspect, the present disclosure provides methods to mitigate the phytotoxic effects of agrichemicals applied to crop plants. All provided methods comprise treating the crop plants with one or more ascarosides though the details of how and when the ascaroside treatment is performed may vary.

[0101] Ascarosides can be applied to the plant by various means, and the mode of application is not particularly limited since it is known plants can respond systemically to ascarosides. Non-limiting examples of suitable modes of ascaroside application include seed treatment, foliar spray or dusting, application by root dip or drench, application to soil, application of time-release formulations, injection into stems or trunks, or application of compositions for absorption through bark (e.g. on stems, trunks, branches or vines).

[0102] In certain embodiments, provided methods comprise co-application of one or more ascarosides and one or more agrichemicals to a crop. Co-application can, in some embodiments, involve application of two separate formulations (one comprising the one or more ascarosides and one comprising the one or more agrichemicals) at close time points, (e.g., substantially simultaneously or within about 1 minute, within about 5 minutes, within about 10 minutes, within about 30 minutes, within about an hour, within about 2 hours, within about 6 hours, within about 12 hours, within about 24 hours, or within about 2 days of one another). When the one or more ascarosides and the agrichemical(s) are applied separately, the one or more ascarosides can be applied before or after application of the agrichemical(s) and may be applied by the same or different means.

[0103] Co-application, can, in some embodiments, involve combining the one or more ascarosides and the one or more agrichemicals shortly before application (e.g., immediately prior to application) to the plants. One suitable method for administering the one or more ascarosides and the one or more agrichemicals is to mix the components in the field; for example, the one or more ascarosides can be added to a tank mix comprising the one or more agrichemicals. 23 409753-013WO (210098) BUSINESS.31545462.1

[0104] In some embodiments, the present disclosure provides a method of mitigating the phytotoxic effects of an agrichemical, comprising administering an ascaroside to a plant, plant part, or soil surrounding the plant or plant part, wherein the plant, plant part, or soil surrounding the plant or plant part is receiving or has received an agrichemical.

[0105] In some embodiments, the present disclosure provides a method of mitigating the phytotoxic effects of an agrichemical, comprising administering an agrichemical to a plant, plant part, or soil surrounding the plant or plant part, wherein the plant, plant part, or soil surrounding the plant or plant part is receiving or has received an ascaroside.

[0106] In other embodiments, the components to be co-applied can be combined at a timepoint further in advance of application. In such embodiments, an agricultural formulation is prepared, the formulation comprising one or more ascarosides and the one or more agrichemicals, optionally in combination with one or more inert ingredients. Advantageously, in some embodiments, combinations of the one or more ascarosides and the one or more agrichemicals provided herein are compatible with one another and the resulting formulations can demonstrate stability over long periods of time (e.g., one week or more, one month or more, two months or more, three months or more, four months or more, five months or more, or six months or more), e.g., under standard conditions (e.g., room temperature and contained in a closed system in one or more of the relative humidity zones). Demonstration of stability in this context can vary. For example, in some embodiments, no noticeable separation is observed by the naked eye. In some embodiments, no significant change to the amount of agrichemical(s) and / or ascaroside(s) is observed via conventional methods (e.g., spectroscopy). In some embodiments, no significant chemical degradation of agrichemical(s) and / or ascaroside(s) is observed using conventional methods (e.g., spectroscopy).

[0107] In certain embodiments, provided methods comprise application of one or more ascarosides and one or more agrichemicals to a crop at different times. This can comprise applying the ascaroside(s) prophylactically before applying the agrichemical(s) (e.g. the ascarosides are applied about 3 days, about 5 days, about 1 week, about 2-3 weeks, about 4-6 weeks, or about 6-10 weeks before application of the agrichemicals). In certain embodiments, the ascaroside(s) can be applied after the agrichemicals (e.g., the ascarosides are applied about 3 days, about 5 days, or about 1 week, after application of the agrichemicals).

[0108] In certain embodiments, provided methods comprise application of one or more ascarosides and one or more agrichemicals to a crop via different methods. For example, the ascaroside(s) may be applied to a crop as a seed treatment (e.g. before planting) while the one or more agrichemicals may be applied by a different means such as foliar spray, dusting, or soil application. In another example, the ascaroside may be applied to the soil (i.e. as a drench or in-furrow application), while the one or more agrichemicals may be applied by a different means such as seed treatment, foliar spray, or dusting. In the case of woody perennial crops such as fruits, nuts and ornamentals, the ascaroside may be applied systemically (i.e. via injection or by applying an absorbable composition onto a trunk, branch or vine), 24 409753-013WO (210098) BUSINESS.31545462.1 while the one or more agrichemicals may be applied by a different means such foliar spray, soil application, or dusting.

[0109] In certain embodiments, provided methods comprise applying ascaroside(s) to the crop more than one time during a growing season (e.g. from 2 to about 6 times). The timing and / or mode of each ascaroside application in such methods may vary. For example, one or more applications may be a co- application with an agrichemical, or may be a prophylactic application applied before the agrichemical(s), or may be an application coming after one or more agrichemical applications. In some embodiments, provided methods include a combination of such timing variations. In some embodiments, provided methods may include application of ascarosides by different means during the growing season (e.g., as a seed treatment followed by a foliar spray, or a systemic application followed by a spray).

[0110] In certain embodiments, provided methods are characterized in that application of the ascarosides results in lessened phytotoxic damage to the crop relative to use of the agrichemicals alone without ascaroside application. In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10%. In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90%. In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms are substantially absent. In certain embodiments, the one or more phytotoxicity symptoms are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these. Agrichemicals

[0111] The agrichemicals in various methods and compositions as provided herein encompass all compounds used on crops that may exhibit phytotoxic effects on plants under at least some conditions. Such agrichemicals include, but are not limited to, antibacterial agents (also referred to as bactericides), antifungal agents (also referred to as fungicides), insecticidal agents (also referred to as insecticides), and anthelmintic agents (also referred to as nematicides). Agrichemicals may also include herbicides, with the understanding that the phytotoxic effects mitigated by the provided compositions and methods are the non-target effects that negatively impact the treated crop (i.e. an herbicide tolerant crop plant) rather than the phytotoxic effects intended on target plants (i.e. weeds). Agrichemicals in the provided methods and formulations may include nutrients or micronutrient compositions. Agrichemicals in the provided methods and formulations may include other materials present in agrichemical formulations such as solvents, adjuvants, wetting agents, surfactants, preservatives, compatibilizers, stabilizers, dyes, antifreeze agents, anti-caking agents, and the like, many of which are known to have some degree of 25 409753-013WO (210098) BUSINESS.31545462.1 phytotoxicity. In some cases, phytotoxicity results from application of combinations of agrichemicals even though each agrichemical alone may not cause phytotoxic effects.

[0112] Antimicrobial agents that may be included among the agrichemicals in the disclosed methods and formulations are not particularly limited. Suitable agrichemicals may be preventative or curative, may have single-site or multi-site activity, may be narrow-spectrum or broad-spectrum in effect, and may be organic or inorganic. They may be chemical or biological. In some embodiments, the agrichemicals are natural, with active ingredients including, but not limited to, sulfur, lime-sulfur, copper (e.g., in the form of copper sulfate), oils (e.g., horticultural oil, neem oil, rosemary oil, and jojoba oil), bicarbonates (e.g., sodium bicarbonate, potassium bicarbonate, and ammonium bicarbonate), and combinations thereof.

[0113] Certain broad chemical classes of fungicidal compounds included among the agrichemicals in certain embodiments as disclosed herein include, but are not limited to, substituted benzenes, thiocarbamates, dithiocarbamates, thio phthalimide copper compounds, nitriles / benzonitriles / chloronitriles, benzimidazoles, dicarboximides, carboxamides / anilides, strobilurins, phenylpyrroles, aromatic hydrocarbons, polyoxins, pyridinamines, phenylamides, cyanoimidazoles, phosphonates, and combinations thereof. Fungicides useful in various formulations and methods as described herein can also be defined by mode of action, e.g., as follows: mitosis disrupters (e.g., thiophanates such as thiophanate-methyl); cell membrane disrupters (e.g., triazoles, such as cyproconazole, difenoconazole, flutriafol, mefentrifluconazole, metconazole, propiconazole, tebuconazole, and tetraconazole; and triazolinthiones, such as prothioconazole); respiration inhibitors (e.g., succinate dehydrogenase inhibitors / carboxamides, such as pyridine carboxamides (e.g., boscalid), pyridinyl-ethylbenzamides (e.g., fluopyram), and pyrazole-4-carboxamides (e.g., benzovindiflupyr, bixafen, fluxapyroxad, penthiopyrad, pydiflumetofen) and quinone outside inhibitors / strobilurins, such as methoxy acrylates (e.g., azoxystrobin and picoxystrobin), dihydro-dioxazines (e.g., fluoxastrobin), methoxy-carbamates (e.g., pyraclostrobin), and oximino-acetates (e.g., trifluoxystrobin)); oxidative phosphorylation uncouplers (e.g., 2,6-dinitroanilines, such as fluazinam); fungicides of unknown activity (e.g., phosphonates, such as phosphorous acid and salts); and fungicides with multi-site contact activity (e.g., inorganic fungicides, such as copper salts and chloronitriles / phthalonitriles, such as Chlorothalonil).

[0114] Suitable specific agents included among the agrichemicals include, but are not limited to, acibenzolar, acibenzoloar-S-methyl, Agrobacterium radiobacter, aldicarb, aliphatic petroleum distillate, allyl isothiocyanate, aluminum tris, ametoctradin, 2-aminobutane, Ampelomyces quisqualis, anilazine, Aureobasidium pullulans (e.g., strains DSM 14940 and 14941), azadirachtin, azoxystrobin, Bacillus amyloliquefaciens (e.g., strain D747 or F727), Bacillus firmus (e.g., Strain I-1582), Bacillus mycoides (e.g., isolate J), Bacillus pumilus (e.g., strain QST 2808), Bacillus subtilis (e.g., strain IAB / BS03, strain QST 713, strain BG03, or strain MBI 600), basic cupric carbonate, benomyl, benzovindiflupyr, bifenazate, bixafen, BLAD, borax, boric acid, boscalid, Burkholderia cepacia, Candida oleophila, capric and caprylic acid, captafol, captan, carbendazim, carbofuran, carbon 26 409753-013WO (210098) BUSINESS.31545462.1 disulfide, carboxin, chitin, chlorfenapyr, chlorine dioxide, chloroneb, chloropicrin, chlorothalonil, cinnamaldehyde, ciproconazole, clove oil, Coniothyrium minitans (e.g., Strain CON / M / 91-08), copper, copper ammonium complex (e.g., copper ammonium carbonate, tannate complex of picro cupric ammonium formate), copper diammonia diacetate complex, copper hydroxide, copper octanoate, copper oxide, copper oxychloride, copper sulfate, cresol, cyazofamid, cyclohexane polymer, cycloheximide, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, dichlone, dichloran, dichloropropene, dicofol, difenoconazole, difenoxazole, difolatan, dimethomorph, demeton, dimethyl disulfide, dinocap, dodemorph acetate, dodine, epoxiconazole, ethaboxam, ethoprop, ethoxyquin, ethylene dibromide, ethaboxam, etridiazole, famoxadone, fenamidone, fenaminosulf, fenamiphos, fenarimol, fenazaquin, fenbuconazole, fenhexamid, fenpyrazamine, fensulfothion, ferbam, fluazinam, fludioxonil, fluensulfone, fluopicolide, fluopyram, fluoxastrobin, fluquinconazole, flusilazole, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl-Al, gamma aminobutyric acid, gibberellic acid, Gliocladium catenalatum (e.g., Strain J1446), Gliocladium virens, harpin, hexachlorobenzene, horticultural mineral oil, hydrated lime, hymexazole, imazalil, iodomethane, ipconazole, iprodione, isofetamid, jojoba oil, kasugamyacin, kresoxim-methyl, L- glutamic acid, laminarin, lime sulfur, mandestrobin, mandipropamid, maneb, mancozeb, mefenoxam, mefentrifluconazole, metalaxyl, metam sodium, metconazole, methyl bromide, methylcyclopropene, methyl isothiocyanate, metrafenone, methyl bromide, methylcyclopropene, metiram, myclobutanil, Myrothecium verrucaria (e.g., strain AARC-0255), neem oil, oxadixyl, oxamyl, oxthioquinox, oxathiapiprolin, oxycarboxin, oxytetracycline, oxythioquinox, Paecilomyces lilacinus (e.g., Strain 251), Pantoea agglomerans (e.g., strain E325), parinol, pentachloronitrobenzene (PCNB), penthiopyrad, peroxide, peroxyacetic acid, peroxyhydrate, petroleum oil, phenylmercury acetate, phosphites, phosphorous acid, picoxystrobin, polyalkylene modified heptamethyltrisiloxane, polyoxin D, polyoxin D zinc salt, potassium bicarbonate, potassium phosphite, potassium silicate, prohexadione calcium, propamocarb, propiconazole, prothioconazole, Pseudomonas aureofaciens, Pseudomonas chlororaphis (e.g., Strain AFS009), Pseudomonas fluorescens, Pseudomonas syringae, pydiflumetofen, pyraclostrobin, pyrimethanil, pyriofenone, quaternary ammonium, quinoxyfen, Reynoutria sachalinensis, rosemary oil, saponins, sedaxane, sodium hypochlorite, spiroxamine, Streptomyces griseoviridis (e.g., strain 61), streptomycin, sulfur, Swinglea glutinosa, tebuconazole, tetrathiocarbonate, thiabendazole, thiamethoxam, thiophanate, thiophanate-methyl, thiram, thyme oil, triadimefon, triadimenol, Trichoderma asperellum (e.g., strain T34), Trichoderma gamsii, Trichoderma harzianum, trifloxystrobin, triflumazole, triforine, triphenyltin hydroxide, triticonazole, urea, Urocladium oudemansii (e.g., U3 strain), vinclozolin, wanilazine, xylenol, zineb, ziram, zoxamid, and combinations thereof.

[0115] In some embodiments, the agrichemicals include or more commercially available antimicrobial agents, e.g., one or more fungicides. In some embodiments, such commercially available antimicrobial agents are fungicidal mixtures. Commercially available antimicrobial agents are known in the art and include, but are not limited to, ABOUND® (Syngenta) comprising Azoxystrobin; ABSOLUTE® 27 409753-013WO (210098) BUSINESS.31545462.1 (Bayer Crop Science), comprising tebuconazole and trifloxystrobin; ACADEMY® (Syngenta) comprising difenoconazole and fludioxonil; ACTIGARD® (Syngenta) comprising acibenzolar-S- methyl; ADAMENT® (Bayer Crop Science), comprising tebuconazole and trifloxystrobin; ALIETTE® (Bayer Crop Science), comprising aluminum tris(O-ethyl phosphonate); ALTO® (Syngenta) comprising cyproconazole; ALUMNI® (Syngenta) comprising thiabendazole; AMISTAR® (Syngenta) comprising azoxystrobin and difenoconazole; APROACH® (DuPont™) comprising picoxystrobin and cyproconazole; APROVIA® (Syngenta) comprising benzovindiflupyr (alone or with propiconazole or difenoconazole); ARCHIVE (Syngenta) comprising fludioxonil and azoxystrobin; CABRIO®, comprising pyraclostrobin; CANNONBALL® (Syngenta) comprising fludioxonil; CARAMBA® (BASF), comprising metconazole; CHAIRMAN® (Syngenta) comprising fludioxonil and propiconazole; CHAMPION® (Nufarm), comprising copper hydroxide and metallic copper equivalent; DELARO® (Bayer Crop Science), comprising trifloxystrobin and prothioconazole; ELATUS® (Syngenta) comprising Azoxystrobin and benzovindiflupyr; F500® (BASF), comprising a strobilurin; FLINT® (Bayer Crop Science), comprising trifloxystrobin; FONTELIS® (Corteva) comprising penthiopyrad; GRADUATE® (Syngenta) comprising fludioxonil (alone or with azoxystrobin); INITUM® (BASF), INSPIRE® (Syngenta) comprising difenoconazole (alone or with cyprodinil or propiconazole); LUNA® (Bayer Crop Science), comprising fluopyram and pyrimethanil; MENTOR® (Syngenta) comprising Propiconazole; MERTECT® (Syngenta) comprising thiabendazole; MINUET® (Bayer Crop Science) comprising Bacillus subtilis strain QST 713; MIRAVIS® (Syngenta) comprising pydiflumetofen (alone or in combination with difenoconazole or propiconazole or fludioxonil or azoxystrobin and propiconazole), OMETGA® (Syngenta) comprising fluazinam; ORONDIS® (Syngenta) comprising oxathiapiprolin (alone or in combination with mefenoxam or chlorothalonil or mandipropamid); PREVICUR® (Bayer Crop Science) comprising propamocarb hydrochloride; PRISTINE®, comprising pyraclostrobin and boscalid; PROLINE® (Bayer Crop Science) comprising prothioconazole; PROPULSE® (Bayer Crop Science) comprising fluopyram and prothioconazole; PROSARO® (Bayer Crop Science) comprising prothioconazole and tebuconazole; PROVOST® (Bayer Crop Science) comprising prothioconazole and tebuconazole; QUADRIS® (Syngenta) comprising azoxystrobin (alone or in combination with Chlorothalonil, mefenoxam, or difenoconazole); QUILT® (Syngenta) comprising Azoxystrobin and Propiconazole; REGALIA® (Marrone BioInnovations), comprising Reynoutria sachalinensis; REVUS® (Syngenta) comprising mandipropamid (alone or in combination with difenoconazole); RIDOMIL® (Syngenta) comprising mefenoxam (alone or in combination with chlorothalonil, copper OH, or mancozeb) SCALA® (Bayer Crop Science) comprising pyrimethanil and 1,2-propanediol; SCHOLAR® (Snygenta) comprising fludioxonil; SERENADE® (Bayer Crop Science) comprising Bacillus subtilis strain QST 713; STRATEGO® (Bayer Crop Science) comprising Propiconazole and Trifloxystrobin; STADIUM® (Syngenta) comprising azoxystrobin, fludioxonil, and difenoconazole; SWITCH® (Syngenta) comprising cyprodinil and fludioxonil; TANOS® (DuPont™) comprising famoxadone and cymoxanil; TILT® (Syngenta) comprising Propiconazole (alone or in combination with Chlorothalonil); TOP® 28 409753-013WO (210098) BUSINESS.31545462.1 (Syngenta) comprising difenoconazole; TRIVAPRO® (Syngenta) comprising Propiconazole, Azoxystrobin, and benzovindiflupyr; UNIFORM® (Syngenta) comprising Azoxystrobin and mefenoxam; VANGARD® (Syngenta) comprising cyprodinil; VELUM® (Bayer Crop Science) comprising fluopyram; VIBRANCE® (Syngenta) comprising sedaxane, mefenoxam, and fludioxonil with thiabendazole or azoxystrobin; VYDATE® (DuPont™) comprising oxamyl; and XEMIUM® (BASF) comprising a carboxamide.

[0116] In certain embodiments, agrichemicals include materials present in formulations but not classified as “active ingredients”, these inert ingredients include materials such as solvents, surfactants, wetting agents, stabilizers, compatibilizers, dyes, preservatives, and the like. One or more inert ingredients, e.g., one or more agronomically acceptable carriers (also referred to as agriculturally acceptable or suitable adjuvants) are generally included within agrichemical formulations. The term “agronomically acceptable carrier” includes any carrier suitable for administration to a plant or soil, e.g., customary excipients in formulation techniques, such as used to form solutions (e.g., directly sprayable or dilutable solutions), emulsions, (e.g., emulsion concentrates and diluted emulsions), wettable powders, suspensions, soluble powders, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, encapsulation into polymeric materials, coatable pastes, natural and synthetic materials impregnated with active compound and microencapsulations in polymeric substances. In some embodiments, agronomically acceptable carriers can include surfactants, emulsifiers, oils, salts, and the like.

[0117] Agrichemical compositions can include one or more agronomically acceptable carriers, such as liquid solvents or solid carriers. Other agrichemicals include, but are not limited to, surfactants, including emulsifiers, dispersants, foam-formers, colorants, processing aids, lubricants, fillers, reinforcements, flame retardants, light stabilizers, ultraviolet radiation absorbers, weather stabilizers, plasticizers, release agents, perfumes, heat-retaining additives (e.g., silica), cross-linking agents, antioxidants, anti-foaming agents, buffers, pH modifiers, compatibility agents, drift control additives, extenders / stickers, tackifiers, plant penetrants, spreaders, wetting agents, and the like. In some embodiments, agrichemicals include wetting agents, emulsifiers, spreaders, and the like. Agrichemical formulations include concentrated versions, in which the agrichemical is present in a concentration of from 2% to 98.0%, with the remaining content being agronomically acceptable carriers / adjuvants.

[0118] Such formulations, especially those with less than 50 percent of the agrichemical, can sometimes be used directly, but these formulations can also be diluted with other agronomically acceptable carriers to form more dilute treating formulations.

[0119] Agrichemicals may include “adjuvant surfactants” to enhance deposition, wetting, and penetration of the compounds onto the target crop and organism. Adjuvant surfactants include, but are not limited to ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts of the esters or sulfosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines, blends of surfactants with mineral or vegetable oils, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum 29 409753-013WO (210098) BUSINESS.31545462.1 hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9- Cu alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C12- C16) ethoxylate; di -sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99.

[0120] Agrichemicals may also include oil-in-water emulsions. In some embodiments, agrichemicals include organic solvents (i.e. an organic solvent that may be incorporated as an auxiliary liquid solvent in an agrichemical formulation). Suitable liquid solvents include, for example, aromatics (e.g., xylene, toluene and alkylnaphthalenes); chlorinated aromatics or chlorinated aliphatic hydrocarbons (e.g., chlorobenzenes, chloroethylenes and methylene chloride); aliphatic hydrocarbons (e.g., cyclohexane); paraffins (e.g., petroleum fractions, mineral and vegetable oils); alcohols (e.g., butanol or glycol and their ethers and esters); ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone) and strongly polar solvents (e.g., dimethylformamide and dimethyl sulfoxide). Other examples of organic solvents include, but are not limited to, xylene, propyl benzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, particularly the dimethyl amides of fatty glycols and glycol derivatives such as the n-butyl ether, ethyl ether or methyl ether of diethylene glycol, the methyl ether of triethylene glycol, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; terpenic solvents, rosin derivatives, aliphatic ketones such as cyclohexanone, complex aliphaticand aromatic alcohols such as 2-ethoxyethanol, vegetable oils such as soy bean oil, rape seed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cotton seed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; and the like. Mixtures of two or more organic liquids may also be employed in the preparation of certain emulsifiable concentrates. Organic liquids include xylene, and propyl benzene fractions, with xylene being most preferred in some cases. Surface-active dispersing agents are typically employed in liquid formulations and in an amount of from 0.1 to 20 percent by weight based on the combined weight of the dispersing agent with one or more of the compounds.

[0121] In some embodiments, agrichemicals comprise solid carriers include, for example, ammonium salts and ground natural minerals (e.g., kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth); ground synthetic minerals (e.g., highly disperse silica, alumina and silicates); crushed and fractionated natural rocks (e.g., calcite, marble, pumice, sepiolite and dolomite); synthetic granules of inorganic and organic meals; granules of organic material (e.g., sawdust, coconut shells, maize cobs and tobacco stalks). In some embodiments, dry compositions can comprise powders and the like.

[0122] In some embodiments, agrichemicals comprise emulsifiers and foam-formers, for example, nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulphates and arylsulfonates) protein hydrolysates. 30 409753-013WO (210098) BUSINESS.31545462.1

[0123] In some embodiments, agrichemicals comprise dispersants, for example, lignin-sulfite waste liquors and methylcellulose. In some embodiments, agrichemicals comprise tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or lattices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. In some embodiments, agrichemicals comprise nonionic emulsifiers, these can include the polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with the polyol or polyoxyalkylene. In some embodiments, agrichemicals comprise cationic emulsifiers including quaternary ammonium compounds and fatty amine salts. In some embodiments, agrichemicals comprise anionic emulsifiers including the oil soluble salts (e.g., calcium) of alkylaryl sulphonic acids, oil-soluble salts or sulfated polyglycolethers and appropriate salts of phosphated- polyglycol ether.

[0124] In some embodiments, agrichemicals comprise surfactants such as sulfonated lignins, condensed naphthalene-sulfonates, the naphthalenesulfonates, alkyl-benenesulfonates, alkysulfonates or nonionic surfactants such as ethylene oxide adducts of alkylphenols or mixtures thereof.

[0125] In some embodiments, agrichemicals comprise colorants such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may also be included in the agrichemicals.

[0126] In certain embodiments, agrichemicals are defined as any substance or formulation intended for application to a plant characterized in that its application to the plant causes some degree of phytotoxic damage to the plant. In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these. Ascaroside-fungicide blends

[0127] In certain embodiments, the present disclosure provides compositions comprising mixtures of ascarosides and other agrichemicals. Such compositions have utility by enabling simple co-application of the ascaroside(s) with the agrichemical(s) to a crop thereby mitigating the phytotoxic effects of one or more of the agrichemical components in the mixture. Certain non-limiting combinations of ascarosides and specific types of agrichemicals that find use in various embodiments of the present disclosure are described in more detail below.

[0128] In certain embodiments, such compositions characterized in that the phytotoxic effects of the combined composition are less than the phytotoxic effects of a composition lacking ascaroside(s). Ascaroside + Triazole Fungicides 31 409753-013WO (210098) BUSINESS.31545462.1

[0129] Triazole fungicides are known to have phytotoxic effects on numerous crops. In some embodiments, the disclosure provides compositions and methods relating to combinations of one or more ascarosides and one or more triazole fungicides (e.g., prothioconazole, tebuconazole, or a fungicide having the same mode of action as prothioconazole or tebuconazole). In some embodiments, the ascaroside can be used with any triazole fungicide or any fungicide that inhibits the CYP51A1 enzyme. The CYP51A1 enzyme is required to biosynthesize ergosterol, a key component in the cell membrane of fungi. The use of the fungicide with at least one ascaroside enhances the activity of the fungicide such that lesser amounts of the fungicide are needed.

[0130] Triazole fungicides include but are not limited to, Myclobutanil, Epoxiconazole, Ipconazole, Metconazole, Uniconazole-P, Uniconazole, Triticonazole, Tricyclazole, Triazbutil, Triadimenol, Triadimefon, Tetraconazole, Tebuconazole, Simeconazole, Quinconazole, Prothioconazole, Propiconazole, Penconazole, Imibenconazole, Hexaconazole, Furconazole, Furconazole-cis, Flutriafol, Flusilazole, Fluquinconazole, Fluotrimazole, Fenbuconazole, Etaconazole, Diniconazole- M, Diniconazole, Difenoconazole, Diclobutrazol, Cyproconazole, Bromuconazole, Bitertanol, Azaconazole, and Amisulbrom. In particular embodiments, the triazole fungicide is prothioconazole or tebuconazole. Mixtures of fungicides are also encompassed, particularly fungicides that are used in combination with prothioconazole, tebuconazole, or other triazoles. Such fungicides used with prothioconazole include, but are not limited to, azoxystrobin, boscalid, tebuconazole, trifloxystrobin, fluopyram, azoxystrobin and benzovindiflupyr, and the like. Such fungicides used with tebuconazole include, but are not limited to, azoxystrobin, boscalid, prothioconazole, trifloxystrobin, fluopyram, azoxystrobin and benzovindiflupyr, and the like.

[0131] Prothioconazole (IUPAC: (RS)-2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2- hydroxypropyl]-2,4-dihydro-1,2,4-triazole-3-thione) is a synthetic chemical produced primarily for its fungicidal properties. Prothioconazole is a systemic, broad-spectrum fungicide in the triazolinthioine chemical class. It is a member of the class of compounds triazoles and possesses a unique toxophore in this class of fungicides. Its effective fungicidal properties can be attributed to its ability to inhibit CYP51A1. This enzyme is required to biosynthesize ergosterol, a key component in the cell membrane of fungi. Prothioconazole is a fungicide produced for the control of diseases caused by ascomycetes, basidiomycetes, and deuteromycetes. Prothioconazole is generally applied alone or as a tank mix with other agents, such as fungicides, insecticides, herbicides, or other crop agents. While any source of prothioconazole can be used, it is sold under various tradenames including Co-Op Pivot, Nufarm Propiconazole, Princeton, Fitness, Pivot 418EC, Quilt, Topnotch, Trivapro, Proline, Cotegra, Prosaro 250EC, Prosaro XTR, Delaro 325SC, Propulse, and Timor 240EC.

[0132] Prothioconazole is typically formulated as a 4 lb / gal suspension concentrate (equivalent to a flowable concentrate; FlC) formulation (Proline® 480 SC Fungicide, 41% active ingredient). The product may be applied as broadcast post emergence foliar or soil sprays (application to soil for peanuts) using ground or aerial equipment at 0.088-0.178 lb ai / A / application (0.100-0.200 kg ai / ha / application). The proposed maximum seasonal rates range 0.285-0.713 lb ai / A (0.320-0.800 kg 32 409753-013WO (210098) BUSINESS.31545462.1 ai / ha), and the proposed retreatment intervals are 5-21 days. Using prothioconazole with at least one ascaroside according to the present disclosure reduces the phytotoxicity of the fungicide.

[0133] Tebuconazole (IUPAC: 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-ylmethyl)pentan- 3-ol) is a systemic fungicide and delivers both curative and preventative control of diseased plants. Tebuconazole is used in a number of different popular fungicide products to control fungi, bacteria, and viruses affecting plants. Tebuconazole is a fungicide that is known as a DMI (demethylation inhibiting fungicide) works by affecting the cell walls of fungi by suppressing spore germination and fungus growth. It also interferes with the production of ergosterol, a molecule essential to the formation of fungus. As a result, the formation of fungus is slowed and eventually stopped. Because of this unique mode of action Tebuconazole is fungistatic or growth-inhibiting rather than fungicidal or fungus killing. Tebuconazole is a flexible fungicide that can be used for both curative and preventative fungus control. It works systemically, absorbing into the target plant to protect it against diseases, prevent further spread or can eliminate the disease entirely depending on the severity level. Some of the common fungal and disease problems tebuconazole is known to treat are rust fungus, sheath blight, leaf spot, and anthracnose. Tebuconazole may also be used on turf and ornamental plants to control various fungal diseases including but not limited to brown patch, gray leaf spot, and powdery mildew.

[0134] Tebuconazole may be applied at rates of 4–10 fl. oz. per acre. Spray volume may range from about 5 up to 300 gallons of finished spray per acre depending upon equipment, plant species and plant growth stage at time of application. However, tebuconazole can cause phytotoxicity. Some plants are sensitive to the triazole active ingredient. The use of tebuconazole in combination with ascaroside(s) as provided according to the present disclosure can reduce or prevent this phytotoxicity.

[0135] In certain embodiments, the disclosure provides blends of a triazole fungicide and an ascaroside where a weight ratio of a triazole fungicide to ascaroside is greater than 1000:1. In certain embodiments, the disclosure provides blends of a triazole fungicide and an ascaroside where a weight ratio of a triazole fungicide to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0136] In certain embodiments, the disclosure provides blends of a triazole fungicide and an ascaroside characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of the triazole fungicide alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; 33 409753-013WO (210098) BUSINESS.31545462.1 death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these.

[0137] In certain embodiments, the disclosure provides blends of tebuconazole and an ascaroside where a weight ratio of tebuconazole to ascaroside is greater than 1000:1. In certain embodiments, the disclosure provides blends of tebuconazole and an ascaroside where a weight ratio of tebuconazole to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0138] In certain embodiments, the disclosure provides blends of tebuconazole and an ascaroside characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of the tebuconazole formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable tebuconazole composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable tebuconazole composition lacking ascaroside(s). In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these.

[0139] In certain embodiments, the disclosure provides blends of prothioconazole and an ascaroside where a weight ratio of prothioconazole to ascaroside is greater than 1000:1. In certain embodiments, the disclosure provides blends of prothioconazole and an ascaroside where a weight ratio of prothioconazole to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0140] In certain embodiments, the disclosure provides blends of prothioconazole and an ascaroside characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of the prothioconazole formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable prothioconazole composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more 34 409753-013WO (210098) BUSINESS.31545462.1 phytotoxicity symptoms are substantially absent relative to use of a comparable prothioconazole composition lacking ascaroside(s). In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these.

[0141] In certain embodiments, the disclosure provides blends of propiconazole and an ascaroside where a weight ratio of propiconazole to ascaroside is greater than 1000:1. In certain embodiments, the disclosure provides blends of propiconazole and an ascaroside where a weight ratio of propiconazole to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0142] In certain embodiments, the disclosure provides blends of propiconazole and an ascaroside characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of the propiconazole formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable propiconazole composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable propiconazole composition lacking ascaroside(s). In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these. Ascaroside + Strobilurin Fungicides

[0143] While the strobilurin fungicides are very valuable for disease control, several are known to cause phytotoxicity in certain circumstances; these are described in product labels. For example, apple cultivars with a genetic background which includes MacIntosh are extremely sensitive to azoxystrobin. Another example: while trifloxystrobin can cause injury to Concord grapes, kresoxim methyl is phytotoxic to certain sweet cherry varieties. Producers should be aware of phytotoxicity concerns both for the treated crop and because of the possibility of injury via spray drift.

[0144] Another aspect of the phytotoxicity risk is the possibility that tank-mixes of strobilurin fungicides with materials that solubilize the cuticle-oils, surfactants, or certain liquid formulations of insecticides-could increase their phytotoxicity potential. Although some of the active ingredient can be found within the host tissue, much of the dose of strobilurin fungicides remains on or within the plant cuticle. Application of a spray material that causes abnormally high levels of these fungicides to 35 409753-013WO (210098) BUSINESS.31545462.1 penetrate into the host tissue can cause phytotoxicity on certain crops or varieties where none is normally expected. The provided blends containing strobilurin(s) and one or more ascarosides can reduce these phytotoxic effects and provide a very convenient means to achieve this improved safety.

[0145] In some embodiments, the disclosure provides compositions and methods relating to blends containing an ascaroside and a strobilurin (e.g., azoxystrobin, kresoxim-methyl, picoxystrobin, pyraclostrobin, trifloxystrobin, famoxadone, or fenamidone). In some embodiments, the ascaroside can be used with any strobilurin fungicide or any fungicide that inhibits mitochondrial respiration, or more particularly, any fungicide that binds to a quinol binding site of a cytochrome complex (e.g., a quinone outside inhibitor or QoI). In certain embodiments, the ascaroside can be used with any strobilurin fungicide (e.g., with a member of the class of natural products known collectively as strobilurins, or with any material referred to as a strobilurin fungicide including synthetic analogs, derivatives or mimics of strobilurin natural products or with compositions comprising synthetic molecules having a similar structure or mode of action to strobilurins including fenamidone and famoxadone). Used with an ascaroside, the fungicide has less phytotoxic effects on the crop, giving growers added flexibility in the rate and / or frequency of application and thereby enabling more effective control of pathogens.

[0146] According to the present disclosure, ascarosides can be used in combination with QoI fungicides, particularly strobilurins, to reduce phytotoxic effects of QoI fungicides or their formulations. QoI fungicides include but are not limited to strobilurins, Azoxystrobin, Picoxystrobin, Trifloxystrobin, Orysastrobin, Pyraclostrobin, Fenamistrobin, Dimoxystrobin, Fluoxastrobin, Metaminostrobin, Mandestrobin, Pyrametostrobin, Pyrazoxystrobin, Kresoxim-methyl, Fenamidone, and Famoxadone.

[0147] As discussed, strobilurins or a fungicide having the same mode of action as strobilurins can be used in the practice of the invention. Mixtures of fungicides are also encompassed, particularly fungicides that are used in combination with strobilurins. Such fungicides used with strobilurins include, but are not limited to, boscalid, tebuconazole, propiconazole, Myclobutanil, Epoxiconazole, Ipconazole, Metconazole, Uniconazole-P, Uniconazole, Triticonazole, Tricyclazole, Triazbutil, Triadimenol, Triadimefon, Tetraconazole, Tebuconazole, Simeconazole, Quinconazole, Prothioconazole, Propiconazole, Penconazole, Imibenconazole, Hexaconazole, Furconazole, Furconazole-cis, Flutriafol, Flusilazole, Fluquinconazole, Fluotrimazole, Fenbuconazole, Etaconazole, Diniconazole-M, Diniconazole, Difenoconazole, Diclobutrazol, Cyproconazole, Bromuconazole, Bitertanol, Azaconazole, Amisulbrom fluopyram, benzovindiflupyr, and the like.

[0148] Azoxystrobin (IUPAC: methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3- methoxyprop-2-enoate) is a synthetic chemical produced primarily for its fungicidal properties. Azoxystrobin is a xylem-mobile systemic fungicide with translaminar, protectant and curative properties. It is a member of the class of compounds strobilurins. Azoxystrobin is effective against numerous fungal plant pathogens including members of the phyla Ascomycota, Deuteromycota, and Basidiomycota, as well as the oomycetes. In addition, its properties mean that it can move 36 409753-013WO (210098) BUSINESS.31545462.1 systemically through plant tissue to protect parts of the crop that were not in contact with the spray. Important diseases which it controls include leaf spot, rusts, powdery mildew, downy mildew, net blotch and blight. Worldwide, azoxystrobin is registered for use on all important crops. For example, in the European Union and United States, it is registered for use in wheat, barley, oats, rye, soya, cotton, rice, strawberry, peas, beans, onions and many other vegetables. Azoxystrobin may be applied alone or as a tank mix with other agents, such as fungicides, insecticides, herbicides, or other crop agents. While any source of azoxystrobin can be used, it is sold under various tradenames including Amistar, Abound, Heritage, Olympus, Ortiva, Priori Xtra, Scotts DiseaseEx, Haedes and Quadris. Suppliers and additional brand names used in the United States are listed in the National Pesticide Information Retrieval System.

[0149] Azoxystrobin is typically formulated as a 2 lb / gal suspension concentrate formulation. Application is made using ground or aerial equipment at 0.1-0.25 lb ai / A / application (0.100-0.200 kg ai / ha / application). The proposed maximum seasonal rates range 1.5 lb ai / A, and the proposed retreatment intervals are 14-21 days. Using azoxystrobin with at least one ascaroside of the invention lowers the phytotoxicity of the fungicide formulation and makes it more practical for growers to reducing the severity of the disease without causing phytotoxin-related damage or stress to the plant.

[0150] Picoxystrobin (IUPAC: (E)-Methyl 3-methoxy-2-(2-(((6-(trifluoromethyl)pyridin-2- yl)oxy)methyl)phenyl)acrylate) is a systemic fungicide and delivers both curative and preventative control of diseased plants. Picoxystrobin is a synthetic chemical produced primarily for its fungicidal properties. Picoxystrobin is a xylem-mobile systemic fungicide with translaminar, protectant and curative properties. It is a member of the class of compounds strobilurins. Picoxystrobin is effective against numerous fungal plant pathogens including members of the phyla Ascomycota, Deuteromycota, and Basidiomycota, as well as the oomycetes. In addition, its properties mean that it can move systemically through plant tissue to protect parts of the crop that were not in contact with the spray. Important diseases which it controls include leaf spot, rusts, powdery mildew, downy mildew, net blotch and blight. Picoxystrobin is currently registered in many countries, including: Argentina, Austria, Belgium, Brazil, Canada, Colombia, Czech Republic, Denmark, Estonia, Finland, France, Germany, Hungary, Ireland, Kenya, Latvia, Lithuania, the Netherlands, New Zealand, Norway, Poland, Romania, Slovakia, South Africa, Sweden, USA and the UK.

[0151] Picoxystrobin is marketed as a single ingredient fungicide and also in several mixtures with other fungicides, including: cyproconazole (Furlong, Stinger and Aproach Prima); chlorothalonil (Credo and Plinker); and cyprodinil (Acanto Prima). Picoxystrobin may be applied alone or as a tank mix with other agents, such as fungicides, insecticides, herbicides, or other crop agents. While any source of picoxystrobin can be used, it is sold under various tradenames including Aproach, Acapela, Cerefit, and Prima. Suppliers and additional brand names used in the United States are listed in the National Pesticide Information Retrieval System.

[0152] Picoxystrobin is typically supplied as a solution concentrate (SC) formulated for application at rates of 0.05 to 0.2 lbs AI per acre. Spray volume may range from about 5 up to 300 gallons of 37 409753-013WO (210098) BUSINESS.31545462.1 finished spray per acre depending upon equipment, plant species and plant growth stage at time of application. Using picoxystrobin with at least one ascaroside of the invention in various manners as outlined herein lowers the phytotoxicity of the fungicide formulation and makes it more practical for growers to reduce the severity of the disease without causing phytotoxin-related damage or stress to the plant.

[0153] In certain embodiments, the disclosure provides blends of a strobilurin fungicide and an ascaroside where a weight ratio of the strobilurin fungicide to ascaroside is greater than 1000:1. In certain embodiments, the disclosure provides blends of a strobilurin fungicide and an ascaroside where a weight ratio of the strobilurin fungicide to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0154] In certain embodiments, the disclosure provides blends of a strobilurin fungicide and an ascaroside characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of the of the strobilurin fungicide formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these.

[0155] In certain embodiments, the disclosure provides blends of azoxystrobin and an ascaroside where a weight ratio of azoxystrobin to ascaroside is greater than 1000:1. In certain embodiments, the disclosure provides blends of azoxystrobin and an ascaroside where a weight ratio of the azoxystrobin to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0156] In certain embodiments, the disclosure provides blends of azoxystrobin and an ascaroside characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of the of azoxystrobin formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable azoxystrobin composition lacking 38 409753-013WO (210098) BUSINESS.31545462.1 ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable azoxystrobin composition lacking ascaroside(s). In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these.

[0157] In certain embodiments, the disclosure provides blends of azoxystrobin and an ascaroside where a weight ratio of azoxystrobin to ascaroside is greater than 1000:1. In certain embodiments, the disclosure provides blends of azoxystrobin and an ascaroside where a weight ratio of the azoxystrobin to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0158] In certain embodiments, the disclosure provides blends of picoxystrobin and an ascaroside characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of the of picoxystrobin formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable picoxystrobin composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable picoxystrobin composition lacking ascaroside(s). In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these. Ascaroside + SDHI Fungicides

[0159] In some embodiments, the disclosure provides compositions and methods relating to an ascaroside and a succinate dehydrogenase inhibitor (SDHI) fungicide. Succinate dehydrogenase (SDH) complex II is considered to be an essential component of the mitochondrial respiratory chain in fungi. SDH enzymes transfer succinate-derived electrons directly to the ubiquinone pool of the respiratory chain, promoting energy transfer in the mitochondria. Succinate dehydrogenase inhibitors (SDHIs) are a class of fungicides that act on mitochondrial SDH complex II, blocking cellular energy transfer, thereby inhibiting the development of fungi. Many SDHIs inhibit fungal respiration by blocking the ubiquinone binding (Qp) site. SDHIs that bind strongly to the Qp site, physically block access to the ubiquinone substrate which consequently prevents further cycling of succinate oxidation. 39 409753-013WO (210098) BUSINESS.31545462.1

[0160] SDHI fungicides include, but are not limited to, benzamide fungicides that inhibit succinate dehydrogenase (SDH) complex II. Examples of benzamide SDHI fungicides include, but are not limited to, benodanil, flufenoxadiazam, flutolanil, mebenil, mepronil, salicylanilide, fluopyram, benzohydroxamic acid, flumetover, fluopicolide, fluopimomide, tioxymid, trichlamide, zarilamid, and zoxamide. SDHI fungicides also include carboxamide fungicides that inhibit succinate dehydrogenase (SDH) complex II. Carboxamide fungicides that inhibit SDH include, but are not limited to: oxathiin fungicides, furan carboxamide fungicides, pyrazine carboxamide fungicides, pyrazole carboxamide fungicides, and pyridine carboxamide fungicides. Examples of oxathiin fungicides include, but are not limited to, carboxin and oxycarboxin. Examples of furan carboxamide fungicides include, but are not limited to, fenfuram, furcarbanil, or methfuroxam. An example of a pyrazine carboxamide fungicide is pyraziflumid. Examples of pyrazole carboxamide fungicides include, but are not limited to, benzovindiflupyr, bixafen, flubeneteram, fluindapyr, fluxapyroxad, furametpyr, inpyrfluxam, isoflucypram, isopyrazam, penflufen, penthiopyrad, pydiflumetofen, pyrapropoyne, sedaxane, ethaboxam, and thifluzamide. Examples of pyridine carboxamide fungicides include, but are not limited to, boscalid or cyclobutrifluram. SDHI fungicides also include thiopheneamide fungicides that inhibit SDH complex II, for example, isofetamid.

[0161] In certain embodiments, the disclosure provides blends of an SDHI fungicide and an ascaroside where a weight ratio of an SDHI fungicide to ascaroside is greater than 1000:1. In certain embodiments, the disclosure provides blends of an SDHI fungicide and an ascaroside where a weight ratio of an SDHI fungicide to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0162] In certain embodiments, the disclosure provides blends of an SDHI fungicide and an ascaroside characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of the of the SDHI fungicide formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these. Multi-way fungicide blends 40 409753-013WO (210098) BUSINESS.31545462.1

[0163] In an effort to overcome increasing resistance of pathogens to fungicides, growers increasingly rely on fungicide products containing blends of multiple fungicidal ingredients, often with distinct modes of action. Such products typically contain a full dose of each component fungicide (e.g. when applied at label rate, such blends provide an amount of each active similar to the amount applied if that active were used at label rate as a solo product). This obviously results in an overall increase in the amount of fungicide applied per acre and a correspondingly increased risk of phytotoxic effects on crops. Unfortunately, such multi-way products are harsher on plants, either due to additive or synergistic phytotoxic effects of the active ingredients, or as a result of the more complicated formulations necessary to compatibilize multiple agrichemicals, or due to the larger volume of adjuvants and inert formulation components applied to the crop with these multi-way products. With these higher levels of phytotoxicity, the benefits obtained in controlling fungicide- resistant pathogens can be undermined and can lead to poor perception of the products in the marketplace.

[0164] In certain embodiments, the disclosure addresses these problems by providing ascaroside blends with multi-way fungicide products, and / or ascaroside products intended for co-application to crops with fungicides containing at least two active agents. In certain embodiments, such products comprise ascaroside(s) and a blend of two or more chemical fungicides. In certain embodiments, the two or more chemical fungicides are from the same chemical class (e.g., two different triazoles or two different strobilurins). More commonly, the two or more chemical fungicides are from the different chemical classes (e.g., a triazole and a strobilurin as; a triazole and an SDHI, or a triazole, a strobilurin and an SDHI).

[0165] In certain embodiments, the disclosure provides blends and / or products intended for co- application to crops containing one or more ascarosides and two or more different triazole fungicides (e.g., such as the triazole fungicides described more fully above). In certain embodiments, the disclosure provides blends and / or products intended for co-application to crops containing one or more ascarosides and two or more different strobilurin fungicides (e.g., such as the strobilurin fungicides described more fully above). In certain embodiments, the disclosure provides blends and / or products intended for co-application to crops containing one or more ascarosides and two or more different SDHI fungicides (e.g. such as the SDHI fungicides described more fully above). In certain embodiments, the disclosure provides blends and / or products intended for co-application to crops containing one or more ascarosides, at least one triazole fungicide, and at least one strobilurin fungicide. In certain embodiments, the disclosure provides blends and / or products intended for co- application to crops containing one or more ascarosides, at least one triazole fungicide, and at least one SDHI fungicide. In certain embodiments, the disclosure provides blends and / or products intended for co-application to crops containing one or more ascarosides, at least one strobilurin fungicide, and at least one SDHI fungicide. In certain embodiments, the disclosure provides blends and / or products intended for co-application to crops containing one or more ascarosides, at least one triazole fungicide, at least one strobilurin fungicide, and at least one SDHI fungicide. 41 409753-013WO (210098) BUSINESS.31545462.1

[0166] In certain embodiments, the disclosure provides blends and / or products intended for co- application to crops containing one or more ascarosides and at least two different chemical fungicides are characterized in that the weight ratio of chemical fungicides to ascarosides(s) is greater than 1000:1. In certain embodiments, the disclosure provides blends and / or products intended for co- application to crops containing one or more ascarosides and at least two different chemical fungicides wherein the weight ratio of chemical fungicides to ascarosides(s) is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, greater than 10,000:1, greater than 20,000:1, or greater than 30,000:1.

[0167] In certain embodiments, the disclosure provides blends of an ascaroside and two or more fungicides characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of a formulation of the two or more fungicides alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these. Ascaroside + insecticides

[0168] In some embodiments, the disclosure provides compositions and methods relating to use of an ascaroside and one or more insecticides. In some embodiments, the disclosure provides compositions and methods relating to an ascaroside and one or more insecticides selected from the group consisting of carbamates, organochlorines, nicotinoids, phosphoramidothioates, organophosphates, pyrethroids and combinations thereof.

[0169] Organophosphates present in the provided blends may include: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacriphos, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, 42 409753-013WO (210098) BUSINESS.31545462.1 propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, and vamidothion.

[0170] Carbamates present in the provided blends may include: alanycarb, aldicarb, 2-sec- butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, and UC-51717.

[0171] Pyrethroids present in the provided blends may include: acrinathin, allethrin, alphametrin, 5- benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl) cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, and Zeta-cypermethrin.

[0172] Arthropod growth regulators present in the provided blends may include: a) chitin synthesis inhibitors such as benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, and chlorfentazine; b) ecdysone antagonists such as halofenozide, methoxyfenozide, and tebufenozide; c) juvenoids such as: pyriproxyfen, Siethoprene (including S- methoprene), and fenoxycarb; and d) lipid biosynthesis inhibitors such as spirodiclofen

[0173] In certain embodiments, the disclosure provides blends of one or more insecticides and an ascaroside where a weight ratio of insecticide(s) to ascaroside is greater than 100:1, greater than 500:1 or greater than 1000:1. In certain embodiments, the disclosure provides blends of an SDHI fungicide and an ascaroside where a weight ratio of an insecticide to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, greater than 10,000:1, greater than 15,000:1, greater than 20,000:1, greater than 30,000:1, or greater than 50,000:1,

[0174] In certain embodiments, the disclosure provides blends of one or more insecticides and an ascaroside characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of the one or more insecticides alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable composition lacking ascaroside(s). In certain 43 409753-013WO (210098) BUSINESS.31545462.1 embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these.

[0175] In an effort to overcome increasing resistance of insect pests to insecticides, growers increasingly rely on products containing blends of multiple insecticidal ingredients, often with distinct modes of action. Such products typically contain a full dose of each component insecticide (e.g. when applied at label rate, such blends provide an amount of each active similar to the amount applied if that active were used at label rate as a solo product). This obviously results in an overall increase in the amount of insecticide applied per acre and a correspondingly increased risk of phytotoxic effects on crops. Unfortunately, such multi-way products are harsher on plants, either due to additive or synergistic phytotoxic effects of the active ingredients, or as a result of the more complicated formulations necessary to compatibilize multiple insecticides, or due to the larger volume of adjuvants and inert formulation components applied to the crop with these multi-way products. With these higher levels of phytotoxicity, the benefits obtained in controlling insecticide-resistant pests can be undermined and can lead to poor perception of the products in the marketplace.

[0176] In certain embodiments, the disclosure addresses these problems by providing ascaroside blends with multi-way insecticide products, and / or ascaroside products intended for co-application to crops with insecticides containing at least two active agents. In certain embodiments, such products comprise ascaroside(s) and a blend of two or more insecticides. In certain embodiments, the two or more insecticides are from the same chemical class (e.g., two different carbamates or two different organochlorines). More commonly, the two or more insecticides are from the different chemical classes (e.g., two-way blends of a carbamate, and an organochlorine, a nicotinoid and a phosphoramidothioate, a carbamate and an organophosphate, a nicitinoid and a pyrethroid, etc. or three way blends containing any combination of these). Ascaroside + Herbicides

[0177] In some embodiments, the disclosure provides compositions and methods relating to use of an ascaroside and one or more herbicides. In some embodiments, the disclosure provides compositions and methods relating to an ascaroside and one or more herbicides wherein the ascarocide(s) serve the purpose of a safener to lessen the phytotoxic effects of the herbicide on the treated crop.

[0178] Herbicides whose phytotoxic side effects on crop plants can be reduced using ascarosides are, for example, herbicides from the group of the carbamates, thiocarbamates, haloacetanilides, substituted phenoxy-, naphthoxy- and phenoxyphenoxy carboxylic acid derivatives and heteroaryloxyphenoxyalkane carboxylic acid derivatives, such as quinolyloxy-, quinoxalyloxy-, pyridyloxy-, benzoxazolyloxy- and benzothiazolyloxyphenoxyalkane carboxylic acid esters, cyclohexanedione derivatives, imidazolinones, pyrimidinyloxypyridincarboxylic acid derivatives, pyrimidyloxybenzoic acid derivatives, sulfonylureas, triazolopyrimidinesulfonamide derivatives and 44 409753-013WO (210098) BUSINESS.31545462.1 S-(N-aryl-N-alkylcarbamoylmethyl)dithiophosphoric esters, hormone-type herbicides, pyridinecarboxylic acids, triazinones, triazolinones, pyridinecarboxamides, hydroxybenzonitriles, isoxazoles. Preference is given to phenoxyphenoxy- and heteroaryloxyphenoxy carboxylic acid esters and salts, sulfonylureas, imidazolinones; isoxazoles and herbicides which, together with ALS inhibitors (acetolactate synthetase inhibitors), are employed for widening the activity spectrum, for example bentazone, cyanazin, atrazin, bromoxynil, dicamba and other leaf-acting herbicides.

[0179] The herbicides of group B are known, for example, from the above-mentioned publications and from “The Pesticide Manual”, The British Crop Protection Council and the Royal Soc. of Chemistry, 12th Edition, 2000, “Agricultural Chemicals Book II—Herbicides—”, by W. T. Thompson, Thompson Publications, Fresno Calif., USA 1990 and “Farm Chemicals Handbook '90”, Meister Publishing Company, Willoughby Ohio, USA, 1990 each of which are incorporated by reference. Other compounds for use in this invention, such as the herbicidal benzoylisoxazole and / or dione compounds, which are not commercially available, may be prepared by the methods described in patent publications, or by the application or adaptation of known methods used or described in the chemical literature for similar compounds.

[0180] In some cases the common names are mentioned in the herbicide list. In such case the common name identifies the active ingredient in its commercially available form or forms including derivatives such as salts and esters, even if a specific salt or ester is not mentioned specifically, preferably its usual commercial form.

[0181] The application of the herbicides can be in pre- or post-emergence application. The preferred application method depends on the usual or optimal application time of the particular herbicide or herbicide combination.

[0182] In certain embodiments, the disclosure provides blends of one or more herbicides and an ascaroside where a weight ratio of herbicide(s) to ascaroside is greater than 100:1, greater than 500:1 or greater than 1000:1. In certain embodiments, the disclosure provides blends of a herbicide and an ascaroside where a weight ratio of a herbicide to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, greater than 10,000:1, greater than 15,000:1, greater than 20,000:1, greater than 30,000:1, or greater than 50,000:1,

[0183] In certain embodiments, the disclosure provides blends of one or more herbicides and an ascaroside characterized in that the blended product has a lower level of phytotoxic effects on the crops to which it is applied compared to application of the one or more herbicides alone. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable composition lacking ascaroside(s). 45 409753-013WO (210098) BUSINESS.31545462.1

[0184] In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these. Ascaroside blends with adjuvants

[0185] As described above, in certain embodiments, ascarosides can be employed to reduce or prevent phytotoxic effects resulting from chemicals used with agrichemicals that are not active ingredients. Such materials include the adjuvants, solvents, and additives that are present in formulated agrichemical products, as well as materials intended for mixing or co-application with agrichemical active ingredients (e.g. surfactants, wetting agents, anti-foaming agents and the like that can be tank mixed with agrichemical prior to application to a crop). In some instances, such materials are known to have phytotoxic effects on plants and the application of ascarosides can reduce or prevent such phytotoxicity.

[0186] In other embodiments, the disclosure provides a useful means to introduce ascarosides for prevention of phytotoxic effects of active agrichemical formulations with which they may be combined. Therefore, the disclosure provides novel multifunctional additives containing one or more traditional additives along with one or more ascarosides present as “safeners” that reduce cytotoxicity of the agrichemical products with which they are combined prior to application. Examples of such compositions include blends of surfactants and ascarosides, blends of wetting agents with ascarosides, blends of anti-foaming agents and ascarosides, blends of surfactants and ascarosides, blends of crop oils and ascarosides. Each of the listed ascaroside-additive blends can be intended for tank mix with other agrichemicals.

[0187] In certain embodiments, such ascaroside-additive blends are characterized in that use of the blended product during application of agrichemicals results in a lower level of phytotoxic effects on the crops to which it is applied compared to application of the agrichemicals with the same additive(s) lacking ascarosides. In certain embodiments, the blend is characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided methods are characterized in that one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable composition lacking ascaroside(s). In certain embodiments, provided blends are characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable additive composition lacking ascaroside(s). In certain embodiments, such phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these. 46 409753-013WO (210098) BUSINESS.31545462.1 Compositions

[0188] As noted above, the disclosed treatment with combinations of an ascaroside and an agrichemical such as an antimicrobial agent (e.g., including, but not limited to, a triazole, strobilurin, or SDHI fungicide as described in detail above) an insecticide (e.g. including, but not limited to carbamates, organochlorines, nicotinoids, phosphoramidothioates, organophosphates, pyrethroids as described above) or an additive such an adjuvant, solvent, surfactant, anti-foaming agent, or wetting agent, or other components of an agrichemical composition, can be used to reduce the phytotoxic effects of those agrichemical agents.

[0189] In some embodiments, treatment with an ascaroside and an agrichemical as provided herein can enable application of a higher rate or more frequent application of the agrichemical since the balance between the beneficial effect desired and the phytotoxic effect on the crop can be shifted favorably by the ascaroside.

[0190] The one or more ascarosides and one or more agrichemicals are generally applied in effective amounts. An effective amount is an amount sufficient to control, treat, prevent, or inhibit the plant pathogen, and / or reduce plant disease severity or reduce plant disease development, or in the case of the ascaroside an amount to reduce or prevent phytotoxic effects of the one or more agrichemicals. By controlling plant disease, the effective amount improves an agronomic trait of interest, as well as promotes and increases plant health, growth, and yield. The one or more ascarosides and one or more agrichemicals can be applied to plants in a variety of ways. In some embodiments, the one or more ascarosides and the one or more agrichemicals are co-applied, either within separate formulations / agricultural composition (e.g., such that both the one or more ascarosides and the one or more agrichemicals are applied within a given time period of each other), or within the same formulation / agricultural composition.

[0191] Co-application can, in some embodiments, involve application of two separate formulations (one comprising the one or more ascarosides and one comprising the one or more agrichemicals) at close time points, e.g., substantially simultaneously or within about 1 minute, within about 5 minutes, within about 10 minutes, within about 30 minutes, within about an hour, within about 4 hours, within about 6 hours, within about 12 hours, within about 24 hours, or within about 2 days of one another). When the one or more ascarosides and the one or more agrichemicals are applied separately, the one or more ascarosides can be applied before or after application of the additional agrichemicals.

[0192] Co-application, can, in some embodiments, involve combining the one or more ascarosides and the one or more agrichemicals shortly before application (e.g., immediately prior to application) to the plants. One suitable method for administering the one or more ascarosides and the one or more agrichemicals is to mix the components in the field; for example, the one or more ascarosides can be added to a tank mix comprising the one or more one or more agrichemicals.

[0193] In other embodiments, the components to be co-applied can be combined at a timepoint further in advance of application. In such embodiments, an agricultural formulation is prepared, the formulation comprising one or more ascarosides and the one or more agrichemicals in combination 47 409753-013WO (210098) BUSINESS.31545462.1 with one or more inert ingredients. Advantageously, in some embodiments, combinations of the one or more ascarosides and the one or more agrichemicals are provided herein which are compatible with one another and the resulting formulations can demonstrate stability over long periods of time (e.g., one week or more, one month or more, two months or more, three months or more, four months or more, five months or more, or six months or more), e.g., under standard conditions (e.g., room temperature and contained in a closed system in one or more of the relative humidity zones). Demonstration of stability in this context can vary. For example, in some embodiments, no noticeable separation is observed by the naked eye. In some embodiments, no significant change to the amount of active ingredient and / or ascaroside is observed via conventional methods (e.g., spectroscopy). In some embodiments, no significant chemical degradation of active ingredient and / or ascaroside is observed using conventional methods (e.g., spectroscopy).

[0194] Such formulations comprising both the one or more ascarosides and the one or more agrichemicals can vary in composition and form. In some embodiments, such formulations are in solid form and in some embodiments, such formulations are in liquid form. As referenced, in addition to the one or more ascarosides and the one or more agrichemicals, one or more inert ingredients, e.g., one or more agronomically acceptable carriers (also referred to as agriculturally acceptable or suitable adjuvants) are generally included within the formulation. It is preferred that non-toxic carriers be used in the formulations and methods of the present disclosure. The term “agronomically acceptable carrier” includes any carrier suitable for administration to a plant or soil, e.g., customary excipients in formulation techniques, such as used to form solutions (e.g., directly sprayable or dilutable solutions), emulsions, (e.g., emulsion concentrates and diluted emulsions), wettable powders, suspensions, soluble powders, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, encapsulation into polymeric materials, coatable pastes, natural and synthetic materials impregnated with active compound and microencapsulations in polymeric substances. In some embodiments, agronomically acceptable carriers can include surfactants, emulsifiers, oils, salts, and the like.

[0195] These compositions can be produced in a known manner, for example, by mixing the one or more ascarosides and the one or more agrichemicals with one or more agronomically acceptable carriers, such as liquid solvents or solid carriers, optionally with the use of additional components including, but not limited to, surfactants, including emulsifiers, dispersants, foam-formers, colorants, processing aids, lubricants, fillers, reinforcements, flame retardants, light stabilizers, ultraviolet radiation absorbers, weather stabilizers, plasticizers, release agents, perfumes, heat-retaining additives (e.g., silica), cross-linking agents, antioxidants, anti-foaming agents, buffers, pH modifiers, compatibility agents, drift control additives, extenders / stickers, tackifiers, plant penetrants, safeners, spreaders, wetting agents, and the like. In some embodiments, such formulations can include one or more additional agrichemicals and / or one or more plant or plant product treatment compounds. Further, some compositions will be residual in that they do not easily wash off the leaves of a plant during rain and thus can protect against pests during and after rainy weather. The additional 48 409753-013WO (210098) BUSINESS.31545462.1 components noted herein can be added directly into the formulation as referenced above or alternatively can be added separately, e.g., at the time of application. In some embodiments, wetting agents, emulsifiers, spreaders, and the like are used in the formulations. Formulations include concentrated versions, in which the agrichemical is present in a concentration of from 0.001 to 98.0%, with the remaining content being agronomically acceptable carriers / adjuvants.

[0196] Such formulations, especially those with less than 50 percent of the present compound, can sometimes be used directly, but these formulations can also be diluted with other agronomically acceptable carriers to form more dilute treating formulations. These latter formulations can include the compounds described herein in lesser concentrations of from 0.001 to 0.1 percent.

[0197] The formulations may additionally contain “adjuvant surfactants” to enhance deposition, wetting, and penetration of the compounds onto the target crop and organism. These “adjuvant surfactants” may optionally be employed as a component of the formulation or as a tank mix. The amount of adjuvant surfactant will typically vary from 0.01 to 1.0 percent by volume, based on a spray-volume of water, preferably 0.05 to 0.5 volume percent. Suitable adjuvant surfactants include, but are not limited to ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts of the esters or sulfosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines, blends of surfactants with mineral or vegetable oils, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9- Cu alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C12- C16) ethoxylate; di -sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99. The formulations may also include oil-in-water emulsionsIf the agronomically acceptable carrier is water, in some embodiments, an organic solvent may be incorporated as an auxiliary liquid solvent. Suitable liquid solvents include, for example, aromatics (e.g., xylene, toluene and alkylnaphthalenes); chlorinated aromatics or chlorinated aliphatic hydrocarbons (e.g., chlorobenzenes, chloroethylenes and methylene chloride); aliphatic hydrocarbons (e.g., cyclohexane); paraffins (e.g., petroleum fractions, mineral and vegetable oils); alcohols (e.g., butanol or glycol and their ethers and esters); ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone) and strongly polar solvents (e.g., dimethylformamide and dimethyl sulfoxide). Other examples of organic solvents include, but are not limited to, xylene, propyl benzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, particularly the dimethyl amides of fatty glycols and glycol derivatives such as the n-butyl ether, ethyl ether or methyl ether of diethylene glycol, the methyl ether of triethylene glycol, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; terpenic solvents, rosin derivatives, aliphatic ketones such as cyclohexanone, complex aliphatic and aromatic alcohols such as 2- ethoxyethanol, vegetable oils such as soy bean oil, rape seed oil, olive oil, castor oil, sunflower seed 49 409753-013WO (210098) BUSINESS.31545462.1 oil, coconut oil, com oil, cotton seed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; and the like. Mixtures of two or more organic liquids may also be employed in the preparation of certain emulsifiable concentrates. Organic liquids include xylene, and propyl benzene fractions, with xylene being most preferred in some cases. Surface-active dispersing agents are typically employed in liquid formulations and in an amount of from 0.1 to 20 percent by weight based on the combined weight of the dispersing agent with one or more of the compounds.

[0198] Suitable solid agronomically acceptable carriers include, for example, ammonium salts and ground natural minerals (e.g., kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth); ground synthetic minerals (e.g., highly disperse silica, alumina and silicates); crushed and fractionated natural rocks (e.g., calcite, marble, pumice, sepiolite and dolomite); synthetic granules of inorganic and organic meals; granules of organic material (e.g., sawdust, coconut shells, maize cobs and tobacco stalks). In some embodiments, dry compositions can comprise powders and the like.

[0199] Suitable emulsifiers and foam-formers include, for example, nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulphates and arylsulfonates) protein hydrolysates.

[0200] Suitable dispersants include, for example, lignin-sulfite waste liquors and methylcellulose. Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or lattices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the disclosed compositions. Examples of nonionic emulsifiers useful in preparing the emulsifiable concentrates include the polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with the polyol or polyoxyalkylene. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include the oil soluble salts (e.g., calcium) of alkylaryl sulphonic acids, oil-soluble salts or sulfated polyglycolethers and appropriate salts of phosphated- polyglycol ether. Other additives may include, for example, mineral and vegetable oils.

[0201] “Surfactants” (e.g., which can comprise typically about 0.5% to about 10% of a wettable powder) include sulfonated lignins, condensed naphthalene-sulfonates, the naphthalenesulfonates, alkyl-benenesulfonates, alkysulfonates or nonionic surfactants such as ethylene oxide adducts of alkylphenols or mixtures thereof

[0202] Colorants such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may also be included in the compositions. 50 409753-013WO (210098) BUSINESS.31545462.1

[0203] Methods of preparing solid and liquid compositions for agrichemical use are generally known and can be employed according to the present disclosure (where such methods involve incorporating one or more ascarosides and one or more agrichemicals) within such compositions). In some embodiments, compositions can be utilized as liquid concentrates, Ready-to-Use (RTU) liquid sprays, dusts, or solids, depending upon the needs of the user. Compositions according to the present disclosure can, in some embodiments, be in the form of granular material (including dusts, pellets, soluble powders, flowable powders, water-dispersible granules, and the like). In some embodiments, compositions according to the present disclosure can be in liquid form (e.g., solutions, suspensions, or emulsions). In some embodiments, compositions are in the form of a granular material treated with a liquid comprising the one or more ascarosides and the one or more additional agrichemicals. In some embodiments, a composition comprising one or more ascarosides and one or more agrichemicals is formed into fibers or filaments and in some such embodiments, a woven or non-woven textile (e.g., film) can be produced therefrom. In some embodiments, a composition as provided herein is pelletized. In some embodiments, a composition as provided herein is in the form of a film, e.g., plastic mulch. Any of the solid compositions provided herein can optionally be coated via methods generally known in the art to delay release of the one or more ascarosides and the one or more agrichemicals. The formulation chosen will depend on the use of the product.

[0204] Dusts containing the compounds of the present disclosure may be prepared by intimately mixing one or more of the compounds in powdered form with a suitable dusty agricultural carrier, such as, for example, kaolin clay, ground volcanic rock, and the like. Dusts can suitably contain from about 1 to about 10 weight percent of the compounds, based on the total weight of the dust.

[0205] Wettable powders may be agglomerated or compacted to form water dispersible granules. These granules include mixtures of compound, inert carriers suitable for granular applications and surfactants. The concentration of the compound is typically between about 0.1% to about 90% by weight. The “inert carrier suitable for granular applications” is typically prophyllite, talc, chalk, gypsum, Fuller’s earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clays, diatomaceous earths, purified silicates, or the like. In such operations, the finely divided carrier and surfactants are typically blended with the compound(s) and milled.

[0206] “Aqueous suspensions” may be prepared where the compounds are dispersed in an aqueous vehicle at a concentration typically in the range of between about 5% to about 50% by weight. The suspensions can be prepared by finely grinding the compound and vigorously mixing it into a vehicle of water, surfactants, and dispersants. Inert ingredients such as inorganic salts and synthetic or natural gums may also be employed to increase the density and / or viscosity of the aqueous vehicle as is desired.

[0207] The amount of the one or more ascarosides and the one or more agrichemicals included within such formulations can vary. In certain specific embodiments, the amount of the one or more ascarosides and the one or more agrichemicals is a synergistically effective amount. Typically, the 51 409753-013WO (210098) BUSINESS.31545462.1 formulation will comprise a lower weight percentage of the one or more ascarosides than the one or more agrichemicals.

[0208] In certain embodiments, provided combinations are characterized in that the amount of the one or more ascarosides represents a very low percentage of the formulation. In certain embodiments, provided combinations are characterized in that ascarosides are present in an amount of less than 1 wt.% relative to the other active ingredient(s). In certain embodiments, provided combinations are characterized in that ascarosides are present in an amount of less than 0.1 wt% relative to the other active ingredient(s). In certain embodiments, provided combinations are characterized in that ascarosides are present in an amount of less than 0.05 wt.% relative to the other active ingredient(s). In certain embodiments, provided combinations are characterized in that ascarosides are present in an amount of less than 0.01 wt.% relative to the other active ingredient(s). In certain embodiments, provided combinations are characterized in that ascarosides are present less than 0.001 wt.% relative to the other active ingredient(s).

[0209] In certain embodiments, co-administration of one or more ascarosides and one or more agrichemicals as described herein can find use in treating living plants or plant parts, soil surrounding plants, soil in which seeds / seedlings are to be planted, or plants or plant parts after harvest. In some embodiments, the one or more ascarosides and one or more agrichemicals are applied to a plant part, i.e., a portion of a plant, e.g., one or more of a root, stem, leaf, seed, and / or flower. Such methods can be conducted at any one or more stages in the life cycle of a plant, e.g., from seed to seedling to growing plant to just prior to harvest. In certain embodiments, co-administration comprises spraying the foliage of a plant with one or more ascarosides and one or more agrichemicals. In certain embodiments, co-administration comprises applying a powder or solid to the foliage of a plant. In certain embodiments, co-administration comprises treating the seeds of a plant (e.g. prior to planting) with one or more ascarosides and one or more agrichemicals. In certain embodiments, co- administration comprises treating a trunk, branch or stem of a plant with one or more ascarosides and one or more agrichemicals. In certain embodiments, co-administration comprises applying one or more ascarosides and one or more agrichemicals to the soil in which a plant is growing or in which a plant will be grown.

[0210] The disclosed treatment methods can, in some embodiments, protect growing plants in the manner described in U.S. Patent No.10,136,595, which is incorporated by reference herein in its entirety. For example, such methods can enhance pathogen resistance and / or induce one or more plant defense responses (thereby inhibiting pathogen growth and / or infestation) in a plant to (or near) which the one or more ascarosides and one or more agrichemicals are applied. Pathogens against which the disclosed methods can enhance resistance include, but are not limited to, oomycetes, bacteria, nematodes, viruses, and insects, e.g., including but not limited to, Pseudomonas syringae, Phytophthora infestans, Blumeria graminis, Heterodera schachtii, Meloidogyne incognita, Meloidogyne hapla, and turnip crinkle virus. 52 409753-013WO (210098) BUSINESS.31545462.1

[0211] The disclosed treatment methods can further provide enhanced control of a range of plant pathogens (e.g., fungal pathogens). Such enhanced control may, in some embodiments, depend upon the selection of the one or more additional agrichemicals. For example, by combining a given agrichemical with one or more ascarosides, the known activity of the agrichemical against certain pathogens in certain crops can be enhanced.

[0212] The exact method by which a plant or soil is treated with the one or more ascarosides and the one or more agrichemicals is not particularly limited. Treatment of plants and / or soil according to the present disclosure can be carried out, e.g., by immersion, spraying, evaporation, fogging, scattering, painting on, side dressing, or in-furrow application. For example, in certain embodiments, plants or soil can be sprayed with one or more suitable liquid compositions, solid plastic mulch compositions can be applied on soil around plants, and / or granular compositions can be provided for in-furrow application or side-dressing. In some embodiments, the methods provided herein comprise treatment of seeds prior to planting.

[0213] The types of plants that can be treated according to the presently disclosed methods is not particularly limited and can be, for example, fruit and vegetable plants, trees, and shrubs. Non- limiting examples of plants that can be treated according to the disclosed methods include, but are not limited to, plants selected from the group consisting of tobacco, Arabidopsis, tomato, barley, potato, sweet potato, yam, cotton, soybean, strawberry, sugar beet, corn, rice, wheat, rye, oat, sorghum, millet, bean, pea, apple, banana, pear, cherry, peach, plum, apricot, almond, grape, kiwi, mango, melon, papaya, walnut, hazelnut, pistachio, raspberry, blackberry, loganberry, blueberry, cranberry, orange, lemon, grapefruit, tangerine, lettuce, carrots, onions, broccoli, cabbage, avocado, cocoa, cassava, cotton, and flax.

[0214] In some embodiments, the compositions and methods provided herein can be used to protect any plant from a fungal or bacterial disease and to promote plant health, growth, and yield, including, but not limited to, monocots and dicots. Examples of plant species of interest include, but are not limited to, corn (Zea mays), Brassica sp. (e.g., B. napus, B. rapa, B. juncea), particularly those Brassica species useful as sources of seed oil, alfalfa (Medicago sativa), rice (Oryza sativa), rye (Secale cereale), sorghum (Sorghum bicolor, Sorghum vulgare), millet (e.g., pearl millet (Pennisetum glaucum), proso millet (Panicum miliaceum), foxtail millet (Setaria italica), finger millet (Eleusine coracana)), sunflower (Helianthus annuus), safflower (Carthamus tinctorius), wheat (Triticum aestivum), soybean (Glycine max), tobacco (Nicotiana tabacum), potato (Solanum tuberosum), peanuts (Arachis hypogaea), cotton (Gossypium barbadense, Gossypium hirsutum), sweet potato (Ipomoea batatus), cassava (Manihot esculenta), coffee (Coffea spp.), coconut (Cocos nucifera), pineapple (Ananas comosus), citrus trees (Citrus spp.), cocoa (Theobroma cacao), tea (Camellia sinensis), banana (Musa spp.), avocado (Persea americana), fig (Ficus casica), guava (Psidium guajava), mango (Mangifera indica), olive (Olea europaea), papaya (Carica papaya), cashew (Anacardium occidentale), macadamia (Macadamia integrifolia), almond (Prunus amygdalus), sugar beets (Beta vulgaris), sugarcane (Saccharum spp.), oats, barley, vegetables, ornamentals, and conifers. 53 409753-013WO (210098) BUSINESS.31545462.1

[0215] Vegetables include tomatoes (Lycopersicon esculentum), lettuce (e.g., Lactuca sativa), green beans (Phaseolus vulgaris), lima beans (Phaseolus limensis), butter beans, kidney beans (Phaseolus vulgaris), cowpeas (Vigna unguiculata), pigeon peas (Cajanus cajan), yam beans, jicama, legumes, peas (I spp.), and members of the genus i such as cucumber (C. sativus), cantaloupe (C. cantalupensis), and musk melon (C. melo). Ornamentals include azalea (Rhododendron spp.), hydrangea (Macrophylla hydrangea), hibiscus (Hibiscus rosasanensis), roses (Rosa spp.), tulips (Tulipa spp.), daffodils (Narcissus spp.), petunias (Petunia hybrida), carnation (Dianthus caryophyllus), poinsettia (Euphorbia pulcherrima), and chrysanthemum.

[0216] Conifers that may be employed in practicing the present invention include, for example, pines such as loblolly pine (Pinus taeda), slash pine (Pinus elliotii), ponderosa pine (Pinus ponderosa), lodgepole pine (Pinus contorta), and Monterey pine (Pinus radiata); Douglas-fir (Pseudotsuga menziesii); Western hemlock (Tsuga canadensis); Sitka spruce (Picea glauca); redwood (Sequoia sempervirens); true firs such as silver fir (Abies amabilis) and balsam fir (Abies balsamea); and cedars such as Western red cedar (Thuja plicata) and Alaska yellow-cedar (Chamaecyparis nootkatensis). In specific embodiments, plants of the present invention are crop plants (for example, corn, alfalfa, sunflower, Brassica, soybean, cotton, safflower, peanut, sorghum, wheat, millet, tobacco, etc.). In other embodiments, a corn or soybean plants is employed.

[0217] Diseases and infestations that can be effectively reduced by treatment with one or more ascarosides and one or more fungicides according to the present disclosure can affect any part of the plant (e.g., seed, root, stem, leaves, and spikes).

[0218] Fungal and bacterial pathogens that may be controlled with the disclosed combinations include but are not limited to those selected from the group consisting of Botrytis cinerea, Cersospora spp, Cercospora sojina, Cercospora beticola, Cercospora canescens, Alternaria solani, Alternaria brassicae, Blumeria graminis f. sp. Tritici, Erysiphe necator, Podosphaera xanthii, Podosphaera leucotricha, Golovinomyces cichoracearum, Erysiphe lagerstroemiae, Erysiphe cichoracearum, Erysiphe graminis, Sphaerotheca pannosa, Sphaerotheca fuliginea, Colletotrichum cereale, Apiognomonia errabunda, Apiognomonia veneta, Colletotrichum gloeosporiodes, Discula fraxinea, Plasmopara viticola, Pseudoperonospora cubensis, Peronospora belbahrii, Bremia lactucae, Peronospora lamii, Plasmopara obduscens, Pythium cryptoirregulare, Pythium aphanidermatum, Pythium irregulare, Pythium sylvaticum, Pythium myriotylum, Pythium ultimum, Phytophthora capsici, Phytophthora nicotianae, Phytophthora infestans, Phytophthora tropicalis, Phytophthora sojae, Fusarium graminearum, Fusarium solani, Fusarium oxysporum, Fusarium graminicola, Gibberella zeae, Colletotrichum graminicola, Phakopsora sp., Phakopsora meibomiae, Phakopsora pachyrizi, Puccinia triticina, Puccinia recondita, Puccinia striiformis, Puccinia graminis, Puccinia spp.,Venturia inaequalis, Verticillium spp, Erwinia amylovora, Monilinia fructicola, Monilinia lax, Monilinia fructigena, Uncinula necator, Gymnosporangium sabinae, Hemileia vastatrix, Phakopsora pachyrhizi, Phakopsora meibomiae, Uromyces appendiculatus, Albugo candida, Bremia lactucae, Peronospora pisi, P. brassicae, Pseudoperonospora humuli, Pseudoperonospora cubensis, Pythium 54 409753-013WO (210098) BUSINESS.31545462.1 ultimum; leafspot, Cladiosporium cucumerinum, Cochliobolus sativus, Cochliobolus miyabeanus, Colletotrichum lindemuthanium, Cycloconium oleaginum, Diaporthe citri, Elsinoe fawcettii, Gloeosporium laeticolor, Glomerella cingulata, Septoria apii, Septoria lycopercisi, Fusarium oxysporum, Rhizoctonia solan, Aspergillus flavus, Fusarium culmorum, Botrytis cinerea, Sclerotinia sclerotiorum, Fusarium culmorum, Phytophthora cactorum, Pythium ultimum, Rhizoctonia solani, Rhizopus oryzae, Sclerotium rolfsii, Septoria nodorum, Botrytis cinerea, Xanthomonas oryzae, Pseudomonas lachrymans, Erwinia amylovora, Venturia inaequalis, Tilletia caries, Ustilago nuda, Ustilago avenae, Pellicularia sasakii, Pyricularia oryzae, Leptosphaeria nodorum, Pseudocercosporrela herpotrichoides, Pyrenophora teres, Pyrenophora graminea, and the like. In some embodiments, the ascarosides and one or more fungicides can be used to control Phoma leaf spot; Phoma stem canker; Powdery mildew; Yellow rust; Brown rust; Tan spot; Septoria leaf and glume blotch on cereals, including barley, rye, wheat, oats, and the like.

[0219] Particular diseases include, but are not limited to, anthracnose (Colletotrichum spp. / Microdochium panattonianum in lettuce, affecting a wide range of crops), botrytis rots (e.g., grey mold / Botrytis cinerea, affecting a range of crops), downy mildews (affecting a range of crops), white blister / white rust (Albugo candida, typically in Brassicas), fusarium wilts and rots (Fusarium species including F. solani and F. oxysporum), powdery mildews (affecting a range of crops), rusts (several species, e.g., Puccinia sorghi in sweet corn; Uromyces appendiculatus in beans, puccinia allii in spring onions, and affecting a range of crops and including e.g., Asian Soybean Rust), rhizoctonia rots (Rhizoctonia solani, commonly referred to as bottom rot in lettuce / wire stem in brassicas, affecting a range of crops), sclerotinia rots (S. sclerotiorum and S. minor, affecting most vegetable crops), sclerotium rots (Sclerotium rolfsii and S. cepivorum, affecting a range of crops), target spot (alternaria solani, affecting tomatoes); damping off (Pythium, rhizoctonia, phytophthora, fusarium, or aphanomyces, affecting a range of crops), cavity spot (Pythium sulcatum, affecting carrots) clubroot (plasmodiophora brassicae, typically in brassicas); tuber diseases (affecting potatoes and sweet potatoes); Pythium species (affecting many vegetable crops); leaf blight alternaria dauci) in carrots; black root rot (different species on different crops, affecting a range of crops), and red root complex (affecting beans); Aphanomyces root rot (Aphanomyces euteiches pv. Phaseoli, affecting beans); aschocyta collar rot (affecting peas); Gummy stem blight (Didymella bryoniae, affecting cucurbits); Alternaria leaf spot (Alternaria cucumerina and A. alternata (cucurbits)); Black leg (Leptosphaeria maculans, affecting brassicas); Ring spot (Mycosphaerella brassicicola, affecting brassicas); late blight (Septoria apiicola, affecting celery); Cercospora leaf spot (Cercospora beticola affecting beets); Leaf blight (Septoria petroelini, affecting parsley); Septoria spot (Septoria lactucae, affecting lettuce); Leaf blight (Stemphylium vesicarium, affecting spring onions); and leaf blight (Alternaria dauci, affecting carrots).

[0220] In certain embodiments, plant diseases which can be treated or reduced or prevented by the compositions and / or methods described herein include, but are not limited to, plant diseases caused by fungi, viruses or viroids, protozoa, bacteria, and the like, e.g., Asian Soybean Rust (ASR), gray mold, 55 409753-013WO (210098) BUSINESS.31545462.1 leaf spot, Frogeye Leaf Spot, Early Blight, Damping off complex, Brown Patch, black scurf, root rot, belly rot, sheath blight, Powdery Mildew, Anthracnose leaf spot, Downy Mildew, Pythium Blight, Late Blight, Fusarium Head Blight (FHB), sudden death syndrome (SDS), Fusarium Wilt, Corn Stalk Rot, Brown Rust, Black Rust, Yellow Rust, Wheat Rust, Rust, Apple Scab, Verticillium Wilt, Fire Blight, and Brown Rot. Examples

[0221] Example 1: A replicated small plot field trial evaluated the phytotoxic effects of application of Blavity™ (a commercial fungicide blend containing prothioconazole (280 g / L) and Fluxapyroxad (200 g / L)). The field trial was structured to mimic typical grower application of Blavity to soybeans for control of Asian Soybean Rust. Blavity was applied twice at 45 days and 60 days after emergence. In some treatment groups, the first application of Blavity was preceded by application of an ascaroside (an ascr#18 formulation marketed under the tradename Phytalix®) applied at a rate of 50 mg / acre 15 days before the first Blavity treatment. Phytotoxic effects were scored in all groups 28 days after the second Blavity application and it was found that treatment groups that included a pre- application of ascarosides showed markedly reduced phytotoxic effects relative to treatment groups without ascaroside treatment (Fig.1). In this study, the ratio of ascaroside applied relative to the fungicide ingredients in Blavity is approximately 5700:1.

[0222] Example 2: A second replicated small plot field trial evaluated the phytotoxic effects of application of Blavity™. The field trial was structured to mimic typical grower application of Blavity to soybeans for control of Asian Soybean Rust. Blavity was applied twice at 45 days and 60 days after emergence. In some treatment groups, the first application of Blavity was preceded by application of an ascaroside (an ascr#18 formulation marketed under the tradename Phytalix®) applied at a rate of 50 mg / acre 15 days before the first Blavity treatment Phytotoxic effects were scored in all groups 35 days after the second Blavity application it was found that treatment groups that included a pre- application of ascarosides showed markedly reduced phytotoxic effects relative to treatment groups without ascaroside treatment (Fig.2). In this study, the ratio of ascaroside applied relative to the fungicide ingredients in Blavity is approximately 5700:1.

[0223] Example 3: Example 3 is performed similarly to Example 1, except the ascaroside tank mixed and co-applied with the first Blavity treatment.

[0224] Example 4: Stability of combinations of PHYTALIX® (an ascr#18 formulation) with various other agrichemicals was studied. Two sets of samples were produced to replicate tank mix formulations (e.g., PHYTALIX® and commercial product, diluted into water at their label rates and formulated blends where PHYTALIX® concentrate is added directly to the formulated commercial product. Samples were stored at room temperature and at 40°C (for accelerated aging) and PHYTALIX® content was monitored periodically using HPLC / MS quantification. Results for 6 months are summarized below. The data surprisingly demonstrates that PHYTALIX® combinations with a wide range of agrichemicals in both concentrated formulations and at tank mix concentration are stable (e.g., with respect to ascaroside content) with a shelf life of at least 6 months or at least 12 56 409753-013WO (210098) BUSINESS.31545462.1 months, despite the incredibly low ascaroside content present in each formulation. This finding is particularly surprising in light of the fact that generally, formulating mixtures of chemical and biological components can be rather challenging due to issues with incompatibility of such components with one another. Table 1: Stability of Ascaroside-Containing Combination Formulations over 6 months (X means formulation is stable) Agrichemical Stability in tank Stability in (in combination with PHYTALIX®) mix formulation 409753-013WO (210098) BUSINESS.31545462.1 Table 2: Stability of Ascaroside-Containing Combination Formulations over 12 months Agrochemical Stability in tank Stability in (in combination with PHYTALIX®) mix formulation ication encompass variations and adaptations developed using information from the embodiments described in the present disclosure. Adaptation or modification of the methods and processes described in this 58 409753-013WO (210098) BUSINESS.31545462.1 specification may be performed by those of ordinary skill in the relevant art. It will be appreciated that use of headers in the present disclosure are provided for the convenience of the reader.

[0226] The presence and / or placement of a header is not intended to limit the scope of the subject matter described herein. Unless otherwise specified, embodiments located in one section of the application apply throughout the application to other embodiments, both singly and in combination. Throughout the description, where compositions, compounds, or products are described as having, including, or comprising specific components, or where processes and methods are described as having, including, or comprising specific steps, it is contemplated that, additionally, there are articles, devices, and systems of the present application that consist essentially of, or consist of, the recited components, and that there are processes and methods according to the present application that consist essentially of, or consist of, the recited processing steps. It should be understood that the order of steps or order for performing certain action is immaterial so long as the described method remains operable. Moreover, two or more steps or actions may be conducted simultaneously.

[0227] All publications and patent applications mentioned in the 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. 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 obvious that certain changes and modifications may be practiced within the scope of the appended claims. 59 409753-013WO (210098) BUSINESS.31545462.1

Claims

CLAIMS What is claimed is:

1. A method of mitigating the phytotoxic effects of an agrichemical, comprising co- administering to a plant, plant part, or soil surrounding the plant or plant part, the agrichemical and one or more ascarosides.

2. A method of mitigating the phytotoxic effects of an agrichemical, comprising administering one or more ascarosides to a plant, plant part, or soil surrounding the plant or plant part, wherein the plant, plant part, or soil surrounding the plant or plant part is receiving or has received an agrichemical.

3. A method of mitigating the phytotoxic effects of an agrichemical, comprising administering an agrichemical to a plant, plant part, or soil surrounding the plant or plant part, wherein the plant, plant part, or soil surrounding the plant or plant part is receiving or has received one or more ascarosides.

4. The method of any of claims 1-3, wherein the agrichemical is a fungicide.

5. The method of claim 4, wherein the fungicide is selected from the group consisting of azoles, strobilurins, carboxamides, nitrogenous heterocyclyl compounds, carbamates and dithiocarbamates, guanidines, antibiotics, organometallic compounds, sulfur-containing heterocyclyl compounds, organophosphorus compounds, organochlorine compounds, nitrophenyl derivatives, inorganic active compounds, and combinations thereof.

6. The method of claim 5, wherein the fungicide is a strobilurin selected from the group consisting of Azoxystrobin, Picoxystrobin, Trifloxystrobin, Orysastrobin, Pyraclostrobin, Fenamistrobin, Dimoxystrobin, Fluoxastrobin, Metaminostrobin, Mandestrobin, Pyrametostrobin, Pyrazoxystrobin, Kresoxim-methyl, Fenamidone, or Famoxadone.

7. The method of claim 5, wherein the fungicide is a benzamide fungicide selected from the group consisting of benodanil, flurenoxadiazam, flutolanil, mebenil, mepronil, fluopyram, benzohydroxamid acid, flumetover, flupicolide, flupimomoide, tioxymid, trchlamide, zarilamid, and zoxamide.

8. The method of claim 5, wherein the fungicide is selected from the group consisting of: 60 409753-013WO (210098) BUSINESS.31545462.1an oxathiin fungicide; a furan carboxamide fungicide; a pyrazine carboxamide fungicide; a pyrazole carboxamide fungicide; and a pyridine carboxamide fungicide.

9. The method of claim 8, wherein the fungicide is selected from the group consisting of carboxin, oxycarboxin, fenfuram, furcarbanil, methfuroxam, pyraziflumid, benzovindiflupyr, bixafen, flubeneteram, fluindapyr, fluxapyroxad, furametpyr, inpyrfluxam, isoflucypram, isopyrazam, penflufen, penthiopyrad, pydiflumetofen, pyrapropoyne, sedaxane, ethaboxam, thifluzamide, boscalid, and cyclobutrifluram.

10. The method of any of claims 1-3, wherein the agrichemical is an insecticide.

11. The method of claim 10, wherein the insecticide is selected from the group consisting of: carbamates, organochlorines, nicotinoids, phosphoramidothioates, organophosphates, pyrethroids and combinations thereof.

12. The method of claim 11, wherein the insecticide is selected from the group consisting of: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton- S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacriphos, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, and vamidothion.

13. The method of claim 11, wherein the insecticide is selected from the group consisting of: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m- 61 409753-013WO (210098) BUSINESS.31545462.1cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, and UC-51717.

14. The method of claim 11, wherein the insecticide is selected from the group consisting of: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2- oxothiolan-3-ylidenemethyl) cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda- cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, and Zeta-cypermethrin.

15. The method of claim 10, wherein the insecticide is an arthropod growth regulator.

16. The method of claim 15, wherein the arthropod growth regulator is selected from the group consisting of: a) chitin synthesis inhibitors such as benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, and chlorfentazine; b) ecdysone antagonists such as halofenozide, methoxyfenozide, and tebufenozide; c) juvenoids such as: pyriproxyfen, Siethoprene (including S-methoprene), and fenoxycarb; and d) lipid biosynthesis inhibitors such as spirodiclofen.

17. The method of any of claims 1-3, wherein the agrichemical is a formulation additive.

18. The method of claim 17, wherein the formulation additive is selected from: adjuvants, solvents, surfactants, wetting agents, anti-foaming agents, preservatives, dyes, anticaking agents, compatibilizers, and combinations of any two or more of these.

19. The method of any of claims 1-3, wherein the agrichemical is a fertilizer or plant nutrient formulation.

20. The method of any of claims 1 to 19, characterized in that the co-administration results in a lower level of phytotoxic effects on the crops to which it is applied compared to application of the one or more agrichemicals without the one or more ascarosides. 62 409753-013WO (210098) BUSINESS.31545462.

121. The method of claim 20, characterized in that one or more phytotoxicity symptoms in a treated crop is reduced by at least 10% relative to use of a comparable composition lacking the one or more ascarosides.

22. The method of claim 21, wherein one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable treatment lacking the one or more ascarosides.

23. The method of claim 20, characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable composition lacking the one or more ascarosides.

24. The method of claim 20, where the phytotoxic effects are selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these.

25. The method of any of claims 1-24, providing increased overall yield of the plant, wherein the increased overall yield of the plant is greater than yield of a plant treated with the agrichemical without co-administration of the one or more ascarosides.

26. The method of any of claims 1-25, wherein the co-administering comprises applying the agrichemical and the one or more ascarosides in the form of separate formulations.

27. The method of any of claims 1-25, wherein the co-administering comprises applying the agrichemical and the one or more ascarosides in the form of a single formulation.

28. The method of any of claims 1-27, wherein the one or more ascarosides have the structure (I) OZ where:Z is an optionally substituted C2-40 aliphatic group, and 63 409753-013WO (210098) BUSINESS.31545462.1each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20 aliphatic, C1-20 acyl, C1-20 heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g., a moiety -C(O)ORc), a C2-20carbamate (e.g., a moiety -C(O)N(Rc)2), a C2-20thioester (e.g., a moiety -C(S)Rc), a C2-20thiocarbonate (e.g., a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g., a moiety -C(S)SRc), a C1-20 thiocarbamate (e.g., a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, where Rcis independently at each occurrence selected from -H, optionally substituted C1-12 aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

29. The method of claim 28, wherein Z is selected from the group consisting of: i. –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic group; ii. –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; iii. –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; iv. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; v. –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is - H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a 64 409753-013WO (210098) BUSINESS.31545462.1nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; vi. –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; vii. –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; viii. –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; and ix. –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. x. –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xi. –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xii. –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic 65 409753-013WO (210098) BUSINESS.31545462.1group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xiii. –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xiv. –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently - H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xv. –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xvi. –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xvii. –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; and xviii. an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising a nitrogen-, oxygen- or sulfur-containing functional group.

30. The method of any one of claims 1 to 29, wherein the one or more ascarosides comprises ascr#18. 66 409753-013WO (210098) BUSINESS.31545462.

131. The method of any one of claims 1 to 29, wherein the one or more ascarosides comprises oscr#16.

32. An agrichemical composition comprising an agrichemical and one or more ascarosides, characterized in that application of the composition to a plant results in less phytotoxicity than application of an equivalent composition without the one or more ascarosides.

33. The composition of claim 32, wherein the agrichemical is a fungicide.

34. The composition of claim 33, wherein the fungicide is selected from the group consisting of azoles, strobilurins, carboxamides, nitrogenous heterocyclyl compounds, carbamates and dithiocarbamates, guanidines, antibiotics, organometallic compounds, sulfur-containing heterocyclyl compounds, organophosphorus compounds, organochlorine compounds, nitrophenyl derivatives, inorganic active compounds, and combinations thereof.

35. The composition of claim 33, wherein the fungicide is a strobilurin selected from the group consisting of Azoxystrobin, Picoxystrobin, Trifloxystrobin, Orysastrobin, Pyraclostrobin, Fenamistrobin, Dimoxystrobin, Fluoxastrobin, Metaminostrobin, Mandestrobin, Pyrametostrobin, Pyrazoxystrobin, Kresoxim-methyl, Fenamidone, or Famoxadone.

36. The composition of claim 33, wherein the fungicide is a benzamide fungicide selected from the group consisting of benodanil, flurenoxadiazam, flutolanil, mebenil, mepronil, fluopyram, benzohydroxamid acid, flumetover, flupicolide, flupimomoide, tioxymid, trchlamide, zarilamid, and zoxamide.

37. The composition of claim 33, wherein the fungicide is selected from the group consisting of: an oxathiin fungicide; a furan carboxamide fungicide; a pyrazine carboxamide fungicide; a pyrazole carboxamide fungicide; and a pyridine carboxamide fungicide.

38. The composition of claim 33, wherein the fungicide is selected from the group consisting of carboxin, oxycarboxin, fenfuram, furcarbanil, methfuroxam, pyraziflumid, benzovindiflupyr, bixafen, flubeneteram, fluindapyr, fluxapyroxad, furametpyr, inpyrfluxam, isoflucypram, isopyrazam, penflufen, penthiopyrad, pydiflumetofen, pyrapropoyne, sedaxane, ethaboxam, thifluzamide, boscalid, and cyclobutrifluram. 67 409753-013WO (210098) BUSINESS.31545462.

139. The composition of claim 32, wherein the agrichemical is an insecticide.

40. The composition of claim 39, wherein the insecticide is selected from the group consisting of: carbamates, organochlorines, nicotinoids, phosphoramidothioates, organophosphates, pyrethroids and combinations thereof.

41. The composition of claim 39, wherein the insecticide is selected from the group consisting of: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton- S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacriphos, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, and vamidothion.

42. The composition of claim 39, wherein the insecticide is selected from the group consisting of: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m- cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, and UC-51717.

43. The composition of claim 39, wherein the insecticide is selected from the group consisting of: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2- oxothiolan-3-ylidenemethyl) cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda- cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, and Zeta-cypermethrin. 68 409753-013WO (210098) BUSINESS.31545462.

144. The composition of claim 39, wherein the insecticide is an arthropod growth regulator.

45. The composition of claim 44, wherein the arthropod growth regulator is selected from the group consisting of: a) chitin synthesis inhibitors such as benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, and chlorfentazine; b) ecdysone antagonists such as halofenozide, methoxyfenozide, and tebufenozide; c) juvenoids such as: pyriproxyfen, Siethoprene (including S-methoprene), and fenoxycarb; and d) lipid biosynthesis inhibitors such as spirodiclofen 46. The composition of claim 32, wherein the agrichemical is a formulation additive.

47. The composition of claim 46, wherein the formulation additive is selected from: adjuvants, solvents, surfactants, wetting agents, anti-foaming agents, preservatives, dyes, anticaking agents, compatibilizers, and combinations of any two or more of these.

48. The composition of claim 32, wherein the agrichemical is a fertilizer or plant nutrient formulation.

49. The composition of any of claims 32 to 48, characterized in that one or more phytotoxicity symptoms in a crop treated with the composition is reduced by at least 10% relative to use of a comparable composition lacking the one or more ascarosides.

50. The composition of claim 49, wherein one or more phytotoxicity symptoms is reduced by at least 15%, by at least 20%, by at least 25%, by at least 35%, by at least 50%, by at least 75%, or by at least 90% relative to use of a comparable treatment lacking the one or more ascarosides.

51. The composition of claim 49 or 50, characterized in that one or more phytotoxicity symptoms are substantially absent relative to use of a comparable composition lacking the one or more ascarosides.

52. The composition of any of claims 32 to 51, wherein the less phytotoxicity comprises a reduction in one or more effects selected from the group consisting of: poor germination; death of seedlings; death or damage to rapidly growing succulent tissues; stunting or delayed plant development; misshaped or distorted plants, fruits, or leaves; russeting or bronzing of 69 409753-013WO (210098) BUSINESS.31545462.1leaves or fruit; dead spots or flecks on leaves; dead leaf tips or leaf margins; dead areas between the veins of the leaves; and combinations of any two or more of these.

53. The composition of any of claims 32-52, wherein the one or more ascarosides have the structure (I) OZ where:Z is an optionally substituted C2-40aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20 aliphatic, C1-20 acyl, C1-20 heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20 carbonate (e.g., a moiety -C(O)ORc), a C2-20 carbamate (e.g., a moiety -C(O)N(Rc)2), a C2-20thioester (e.g., a moiety -C(S)Rc), a C2-20thiocarbonate (e.g., a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g., a moiety -C(S)SRc), a C1-20 thiocarbamate (e.g., a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, where Rcis independently at each occurrence selected from -H, optionally substituted C1-12 aliphatic, optionally substituted C1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

54. The composition of claim 53, wherein Z is selected from the group consisting of: i. –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic group; ii. –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; iii. –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally 70 409753-013WO (210098) BUSINESS.31545462.1substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; iv. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; v. –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is - H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; vi. –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; vii. –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; viii. –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; and ix. –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. x. –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an 71 409753-013WO (210098) BUSINESS.31545462.1optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xi. –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xii. –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xiii. –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xiv. –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently - H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xv. –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xvi. –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a 72 409753-013WO (210098) BUSINESS.31545462.1nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xvii. –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; and xviii. an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising a nitrogen-, oxygen- or sulfur-containing functional group.

55. The composition of any of claims 32 to 54, wherein the one or more ascarosides comprises ascr#18.

56. The composition of any of claims 32 to 54, wherein the one or more ascarosides comprises oscr#16.

57. The composition of any of claims 32 to 56, in solid form.

58. The composition of claim 57, wherein the solid form comprises powder or granules.

59. The composition of any of claims 32 to 56, in liquid form.

60. The composition of claim 59, wherein the liquid form is a sprayable formulation.

61. The composition of claim 59 or 60, wherein the composition is shelf-stable for a period of greater than 6 months.

62. The composition of any of claims 32 to 61, further comprising one or more additional components selected from the group consisting of surfactants, including emulsifiers, dispersants, foam-formers, colorants, processing aids, lubricants, fillers, reinforcements, flame retardants, light stabilizers, ultraviolet radiation absorbers, weather stabilizers, plasticizers, release agents, perfumes, heat-retaining additives (e.g., silica), cross-linking agents, antioxidants, anti-foaming agents, buffers, pH modifiers, compatibility agents, drift control additives, extenders / stickers, tackifiers, plant penetrants, safeners, spreaders, and wetting agents. 73 409753-013WO (210098) BUSINESS.31545462.

163. The composition of any of claims 32-62, wherein the fungicide and the ascaroside are present in a weight ratio of greater than 1000:1 fungicide:ascaroside. 74 409753-013WO (210098) BUSINESS.31545462.1

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