Compositions and methods for mitigating the phytotoxic effects of pesticides

Abstract

This application relates to the use of one or more ascalosides to mitigate the phytotoxic effects of pesticides. Various combinations can provide enhanced performance of the pesticide, and certain combinations, surprisingly, show a significant reduction in the phytotoxicity of the pesticide. Various combinations can, surprisingly, be co-formulated to provide storage-stable compositions. In one embodiment, a formulation is provided that contains a mixture of one or more ascalosides and one or more pesticides. In certain embodiments, such a formulation can be advantageously stable over long periods of time.

Description

[Technical Field]

[0001] Cross-reference of related applications This application claims priority to U.S. Provisional Application No. 63 / 506,575, filed on June 6, 2023, which is incorporated herein by reference in its entirety.

[0002] This application generally relates to pesticide compounds, compositions, and methods for reducing the phytotoxic effects of pesticides such as fungicides and insecticides. [Background technology]

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

[0004] Ascaloside treatments, when applied to plants, have been shown to be effective in increasing plant resistance to certain pathogens and / or in inducing and priming plant defense responses (which can inhibit pathogen growth and / or parasitism). By activating and / or priming the plant's innate defenses, ascaloside can prevent pathogen proliferation and / or protect crops from harmful effects caused by a variety of pathogens.

[0005] When chemical substances are used to protect plants from pests, fertilize plants, or regulate plant growth, plant damage (phytotoxicity) can occur. This phytotoxicity is highly undesirable because it can slow growth, reduce yields, or conversely, make crops more susceptible to infection or insect damage. A simple and cost-effective method to prevent the phytotoxic effects of pesticides would be desirable. This invention addresses this problem and related issues. [Overview of the Initiative]

[0006] Ascalosides are known to prime and / or activate plant defenses, thereby providing a useful means of protecting plants from pathogens such as fungi and bacteria, but there are no reports that ascaloside treatments may cause non-pathogenic stress to plants. Surprisingly, this disclosure encompasses the recognition that the application of ascalosides to plants can mitigate the phytotoxic effects of other pesticides. This disclosure provides compositions and methods for reducing or preventing damage to plants by phytotoxic agents by applying one or more ascalosides to plants.

[0007] The toxic effects of pesticides on plants may include, but are not limited to, poor germination, especially when soil trenches are used; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; and dead areas between leaf veins.

[0008] In some embodiments, methods are provided herein that involve the simultaneous application of one or more ascalosides with one or more pesticides, where one or more pesticides have some degree of phytotoxic effect on the crop. The methods provided may include applying the components within a single formulation (e.g., a liquid formulation), or the one or more ascalosides may be applied separately, either before or after the application of one or more pesticides.

[0009] In one embodiment, a formulation is provided that contains a mixture of one or more ascalosides and one or more pesticides. In certain embodiments, such a formulation can be advantageously stable over a long period of time.

[0010] These and other features, aspects, and advantages of this disclosure will become apparent from reading the following detailed description together with the accompanying drawings, which are briefly described below. The present invention includes any combination of any two, three, four, or more features or elements described in this disclosure, as well as any combination of any two, three, four, or more of the embodiments described above, whether such features or elements are expressly combined in the specific embodiments herein. This disclosure is intended to be read as a whole so that any separable feature or element of the disclosed invention is intended to be combined in any of its various aspects and embodiments, unless it is clearly indicated in the context that it is not. Other aspects and advantages of this disclosure will become apparent below.

[0011] The teachings described herein will be better understood by reading them together with the accompanying drawings, as they will be better understood from the following description of various exemplary embodiments. It should be understood that the drawings below are for illustrative purposes only and are not intended to limit the scope of these teachings in any way. The aforementioned and other purposes, aspects, features, and advantages of this disclosure may be better understood by referring to the following description in conjunction with the accompanying drawings. [Brief explanation of the drawing]

[0012] [Figure 1]This chart shows the plant toxicity assessment (0-100%) at 88 days post-emergence in a soybean field trial using Blavity® (a commercially available fungicide containing a blend of prothioconazole and fluxapyroxade). Blavity was applied twice at the labeled ratio (45 and 60 days post-emergence). Prior application of ascaloside (Phytalix®) 15 days before the first Blavity treatment reduced the plant toxicity effect of the Blavity treatment by more than 20%.

[0013] [Figure 2] This chart shows the plant toxicity assessment (0-100%) at 95 days post-emergence in a soybean field trial using Blavity® (a commercially available fungicide containing a blend of prothioconazole and fluxapyroxade). Blavity was applied twice at the labeled ratio (45 and 60 days post-emergence). Prior application of ascaloside (Phytalix®) 15 days before the first Blavity treatment reduced the plant toxicity effect of the Blavity treatment by more than 50%. [Modes for carrying out the invention]

[0014] definition To facilitate understanding of this disclosure, certain terms are defined below. Additional definitions of the terms below and other terms are provided throughout this specification.

[0015] In this application, unless otherwise clearly stated in the context, the term “one (a)” may be understood to mean “at least one.” 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 the itemized component or step, whether indicated by itself or with one or more additional components or steps. In this application, the term “comprise” and its variations, e.g., “comprising” and “comprises,” are not intended to exclude other appendices, components, integers, or steps.

[0016] Where used herein, the terms “about” and “approximately” are used interchangeably. Unless otherwise specified, the terms “about” and “approximately” may be understood to allow for a standard deviation, as understood by those skilled in the art. Where a range is presented herein, both ends are included. Any numbers used in this application, with or without “about” / “approximately,” are intended to cover any normal variation as understood by those skilled in the art. In some embodiments, the terms “approximately” or “about” refer to a range of values ​​that, unless otherwise specified or evident from the context, 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) a given standard reference value (except where such a number exceeds 100% of the possible value).

[0017] Definitions of specific functional groups and chemical terms are described in more detail below. For the purposes of this invention, chemical elements are as defined in the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75. thIdentified according to the Ed., inside cover, specific functional groups are generally defined as described therein. In addition, general principles of organic chemistry, as well as specific functional parts and reactivity, are described in *Organic Chemistry*, Thomas Sorrell, University Science Books, Sausalito, 1999, and *Smith and March March's Advanced Organic Chemistry*, 5 th Edition, John Wiley & Sons, Inc., New York, 2001, Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989, Carruthers, Some Modern Methods of Organic Synthesis, 3 rd This information is contained in Edition, Cambridge University Press, Cambridge, 1987, and the entire contents of each section are incorporated herein by reference.

[0018] Certain compounds provided herein may contain one or more chiral centers and therefore may exist in various stereoisomeric forms, such as enantiomers and / or diastereomers. Accordingly, the compounds of the present invention and their compositions may be in the form of individual enantiomers, diastereomers or geometric isomers, or in the form of mixtures of stereoisomers. In certain embodiments, the compounds described herein are enanthopureous compounds. In certain other embodiments, mixtures of enantiomers or diastereomers are provided.

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

[0020] As used herein, the term “isomer” includes any and all geometric isomers and stereoisomers. For example, “isomer” includes cis and trans isomers, E and Z isomers, R and S isomers, diastereomers, (d)-isomers, (l)-isomers, racemic mixtures thereof, and other mixtures thereof, as is within the scope of this disclosure. For example, in some embodiments, a compound may be provided substantially free of one or more corresponding stereoisomers and may be referred to as “stereochemically concentrated.”

[0021] Where a particular enantiomer is preferred, in some embodiments the compound may be provided substantially without the opposite enantiomer, and may be referred to as “optically concentrated.” As used herein, “optically concentrated” means that the compound of the present invention is composed of a significantly higher proportion of one enantiomer. In some particular embodiments, the compound is composed of at least about 90% by weight of one enantiomer. In some embodiments, the compound is composed of at least about 95% by weight, 97% by weight, 98% by weight, 99% by weight, 99.5% by weight, 99.7% by weight, 99.8% by weight, or 99.9% by weight of one enantiomer. In some embodiments, the enantiomer excess of the compound provided is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9%. In some embodiments, enantiomers may be separated from the racemic mixture by any known method such as chiral high-performance liquid chromatography (HPLC) and the formation and crystallization of chiral salts, or they may be prepared by asymmetric synthesis. See, for example, Jacques, et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981), Wilen, SH, et al., Tetrahedron 33:2725 (1977), Eliel, ELStereochemistry of Carbon Compounds (McGraw-Hill, NY, 1962), and Wilen, SH, Tables of Resolving Agents and Optical Resolutions p.268 (ELEliel, Ed., Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0022] As used herein, the terms "halo" and "halogen" refer to an atom selected from fluorine (fluoro, -F), chlorine (chloro, -Cl), bromine (bromo, -Br), and iodine (iodo, -I).

[0023] As used herein, the terms “aliphatic” or “aliphatic group” refer to a hydrocarbon moiety that may be linear (i.e., unbranched), branched, or cyclic (including condensed, cross-linked, and spiro-condensed polycyclic), and may be fully saturated or contain one or more unsaturated units, but is not aromatic. Unless otherwise specified, an aliphatic group contains 1 to 30 carbon atoms. In certain embodiments, an aliphatic group contains 1 to 12 carbon atoms. In certain embodiments, an aliphatic group contains 1 to 8 carbon atoms. In certain embodiments, an aliphatic group contains 1 to 6 carbon atoms. In some embodiments, an aliphatic group contains 1 to 5 carbon atoms, in some embodiments, an aliphatic group contains 1 to 4 carbon atoms, in yet another embodiment, an aliphatic group contains 1 to 3 carbon atoms, and in yet another embodiment, an aliphatic group contains 1 to 2 carbon atoms. Suitable aliphatic groups include, but are not limited to, linear or branched alkyl, alkenyl, and alkynyl groups, as well as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl groups and their hybrids.

[0024] As used herein, the terms “heteroaliphatic” or “heteroaliphatic group” refer to an aliphatic group in which one or more carbon or hydrogen atoms are replaced by heteroatoms (e.g., oxygen, nitrogen, sulfur, phosphorus, boron, etc.). In some embodiments, the heteroaliphatic group is a heterocyclyl group.

[0025] As used herein, the term “unsaturated” means that a part has one or more double or triple bonds.

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

[0027] As used herein, the term “alkenyl” refers to a monovalent group derived from a linear or branched 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 to 12 carbon atoms. In certain embodiments, alkenyl groups contain 2 to 8 carbon atoms. In certain embodiments, alkenyl groups contain 2 to 6 carbon atoms. In some embodiments, alkenyl groups contain 2 to 5 carbon atoms, in some embodiments, alkenyl groups contain 2 to 4 carbon atoms, in yet another embodiment, alkenyl groups contain 2 to 3 carbon atoms, and in yet another embodiment, alkenyl groups contain 2 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, butenyl, and 1-methyl-2-buten-1-yl.

[0028] The term "aryl," used alone or as part of a larger phrase, such as "aralkyl," "aralkoxy," or "aryloxyalkyl," refers to monocyclic and polycyclic ring systems having a total of 5 to 20 ring members, where at least one ring in the system is aromatic, and each ring in the system contains 3 to 12 ring members. The term "aryl" may be used interchangeably with the term "aryl ring." In certain embodiments, "aryl" refers to aromatic ring systems, including but not limited to phenyl, biphenyl, naphthyl, and anthracyl, which may have one or more substituents. 「 The term "aryl" also includes groups in which an aromatic ring is condensed with one or more additional rings, such as benzofuranyl, indanyl, phthalimidyl, naphthoimidyl, phenantridinyl, or tetrahydronaphthyl.

[0029] The terms "heteroaryl" and "heteroar-" used alone or as part of a larger phrase, such as "heteroaralkyl" or "heteroaralkoxy," refer to a group having 5 to 10 ring atoms, preferably 5, 6, or 9 ring atoms, sharing 6, 10, or 14 π electrons within the cyclic arrangement, and having 1 to 5 heteroatoms in addition to carbon atoms. The term "heteroatom" refers to nitrogen, oxygen, or sulfur, and includes any oxidized form of nitrogen or sulfur, and any quaternized form of basic nitrogen. Heteroaryl groups include, but are not limited to, thienyl, furanyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, indolidinyl, prinyl, naphthilidinyl, and pteridinyl. The terms “heteroaryl” and “hetero-” also, as used herein, include groups in which a heteroaromatic ring is condensed with one or more aryl, alicyclic, or heterocyclyl rings, and the radical or bond site is located on the heteroaromatic ring. Non-limiting examples include indolyl, isoindolyl, benzothienyl, benzofuranyl, dibenzofuranyl, indazolyl, benzimidazolyl, benzthiazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 4H-quinolidinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, and pyrido[2,3-b]-1,4-oxazine-3(4H)-one. Heteroaryl groups may be monocyclic, bicyclic, bridging bicyclic, or spirocyclic. The term "heteroaryl" may be used interchangeably with the terms "heteroaryl ring," "heteroaryl group," or "heteroaromatic," any of which may include a optionally substituted ring. The term "heteroaralkyl" refers to an alkyl group substituted with a heteroaryl group, where the alkyl and heteroaryl moieties are independently and optionally substituted.The term "heteroarylenyl" refers to a divalent heteroaryl group (e.g., pyridylenyl).

[0030] As used herein, the terms “heterocycle,” “heterocyclyl,” “heterocyclic radical,” and “heterocyclic ring” are interchangeable and refer to stable 5-7 membered monocyclic or 7-10 membered bicyclic heterocyclic moieties that are either saturated or partially unsaturated and have one or more, preferably 1-4, heteroatoms in addition to the carbon atoms, as defined above. When used in relation to the ring atoms of a heterocycle, the term “nitrogen” includes substituted nitrogen. For 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 bonded to its pendant group with 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, but are not limited to, tetrahydrofuranyl, tetrahydrothiophenylpyrrolidinyl, piperidinyl, pyrrolinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl, oxazolidinyl, piperazinyl, dioxanyl, dioxolanyl, diazepinyl, oxazepinyl, thiazepinyl, morpholinyl, and quinuclidinyl. The terms “heterocyclic ring,” “heterocyclyl,” “heterocyclyl ring,” “heterocyclic group,” “heterocyclic moiety,” and “heterocyclic radical” are used interchangeably herein and also include groups in which a heterocyclyl ring is fused to one or more aryl, heteroaryl, or alicyclic rings, such as indolinyl, 3H-indolyl, chromanyl, phenantridinyl, or tetrahydroquinolinyl. In some embodiments, the heterocycle may be a 5- to 12-membered bicyclic, bridging bicyclic, or spirocyclic ring. The heterocycle may contain one or more oxo (=O) or thioxo (=S) substituents. The term "heterocyclylalkyl" refers to an alkyl group substituted with a heterocyclyl, where the alkyl and heterocyclyl moieties are independently and optionally substituted.

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

[0033] As described herein, the compounds 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 suitable substituents 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 particular group, the substituents may be the same or different at all positions. Combinations of substituents contemplated are preferably those that result in the formation of stable or chemically possible compounds. The term "stable," as used herein, refers to compounds that do not substantially change when placed under conditions that 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) 0-4 R°, -(CH2) 0-4 OR°, -O-(CH2) 0-4 C(O)OR°, -(CH2) 0-4 CH(OR°)2, -(CH2) 0-4 SR°, -(CH2) that may be substituted with R° 0-4 Ph, -(CH2) that may be substituted with R° 0-4 O(CH2) 0-1 Ph, -CH=CHPh that may be substituted with R°, -NO2, -CN, -N3, -(CH2) 0-4 N(R°)2, -(CH2) 0-4 N(R°)C(O)R°, -N(R°)C(S)R°, -(CH2) 0-4 N(R°)C(O)NR°2, -N(R°)C(S)NR°2, -(CH2) 0-4 N(R°)C(O)OR°, -N(R°)N(R°)C(O)R°, -N(R°)N(R°)C(O)NR°2, -N(R°)N(R°)C(O)OR°, -(CH2) 0-4C(O)R°, -C(S)R°, -(CH2) 0-4 C(O)OR°, -(CH2) 0-4 C(O)N(R°)2, -(CH2) 0-4 C(O)SR°, -(CH2) 0-4 C(O)OSiR°3, -(CH2) 0-4 OC(O)R°, -OC(O)(CH2) 0-4 SR-, SC(S)SR°, -(CH2) 0-4 SC(O)R°, -(CH2) 0-4 C(O)NR°2, -C(S)NR°2, -C(S)SR°, -SC(S)SR°, -(CH2) 0-4 OC(O)NR°2, -C(O)N(OR°)R°, -C(O)C(O)R°, -C(O)CH2C(O)R°, -C(NOR°)R°, -(CH2) 0-4 SSR°, -(CH2) 0-4 S(O)2R°, -(CH2) 0-4 S(O)2OR°, -(CH2) 0-4 OS(O)2R°, -S(O)2NR°2, -(CH2) 0-4 S(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, -(C 1-4 Linear or branched alkylenes)ON(R°)2, or -(C 1-4 The linear or branched alkylene is C(O)ON(R°)2, where each R° can be substituted as defined below, independently of hydrogen, C 1-8 Aliphatic, -CH2Ph, -O(CH2) 0-1 Ph is a 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or, notwithstanding the above definition, two independent occurrences of R° may, together with their intervening atom(s), form a 3-12 member saturated, partially unsaturated, or aryl monocyclic or polycyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, as defined below.

[0035] Suitable monovalent substituents on R° (or rings formed by two independent occurrences of R° together with the intervening atom) are, independently, halogens, -(CH2) 0-2 R ● ,-(HaroR ● ), -(CH2) 0-2 OH, -(CH2) 0-2 Ure ● ,-(CH2) 0-2 CH(OR ● )2, -O(HaroR ● ), -CN, -N3, -(CH2) 0-2 C(O)R ● ,-(CH2) 0-2 C(O)OH, -(CH2) 0-2 C(O)OR ● ,-(CH2) 0-4 C(O)N(R°)2, -(CH2) 0-2 SR ● ,-(CH2) 0-2 SH, -(CH2) 0-2 NH2, -(CH2) 0-2 NHR ● ,-(CH2) 0-2 NR ● 2, -NO2, -SiR ● 3. -OSiR ● 3, -C(O)SR ● ,-(C 1-4 Linear or branched alkylene)C(O)OR ● , or -SSR ● And each R ● It is either unsubstituted, or if preceded by "halo", it is substituted by only one or more halogens and independently, C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1 The R° saturated, partially unsaturated, or aryl ring is selected from 5-6 membered saturated, partially unsaturated, or aryl rings having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Preferred divalent substituents on the saturated carbon atom of R° include =O and =S.

[0036] Suitable divalent substituents on a saturated carbon atom of the "optionally substituted" radical include, for example, =O, =S, =NNR * 2, =NNHC(O)R * , =NNHC(O)OR * , =NNHS(O)2R * , =NR * , =NOR * , -O(C(R * 2)) 2-3 O-, or -S(C(R * 2)) 2-3 S-, where each independent occurrence of R * is selected from hydrogen, C 1-6 aliphatic which may be substituted as defined below, or an unsubstituted 5- to 6-membered saturated, partially unsaturated, or aryl ring having from 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents bonded to a replaceable carbon proximal to the "optionally substituted" radical include -O(CR * 2) 2-3 O-, where each independent occurrence of R * is selected from hydrogen, C 1-6 aliphatic which may be substituted as defined below, or an unsubstituted 5- to 6-membered saturated, partially unsaturated, or aryl ring having from 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

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

[0038] Suitable substituents on the nitrogen of the "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 † and each R † is independently hydrogen, C 1-6 aliphatic which may be substituted as defined below, unsubstituted -OPh, or an unsubstituted 5- to 6-membered saturated, partially unsaturated, or aryl ring having 0 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or regardless of the above definition, two independent occurrences of R † together with the intervening atom(s) form an unsubstituted 3- to 12-membered saturated, partially unsaturated, or aryl monocyclic or bicyclic ring having 0 to 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, and each R ● is unsubstituted or, when "halo" precedes, is substituted only by one or more halogens and is independently C 1-4Aliphatic, -CH2Ph, -O(CH2) 0-1 It is a 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from pH, nitrogen, oxygen, or sulfur.

[0040] As used herein, the term “substantially” refers to a qualitative state indicating the whole or nearly whole extent or degree of the feature or quality of the subject.

[0041] There is a convention to name ascalosides with a prefix of several letters followed by a pound sign (#) and a number (e.g., ascr#18). This convention is used in scientific literature, and those skilled in the art will understand that each such name is associated with a specific chemical structure of a known composition and will immediately understand the structure of the molecule indicated using this nomenclature. Unless otherwise indicated, all compound identifiers of this form used herein conform to the definitions listed 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 rhizomatous nematode) or insect that has pathogenic effects on plants.

[0043] Modes for carrying out the invention The present invention provides compositions and methods for mitigating the phytotoxic effects of pesticides on plants. The present disclosure relates to the treatment of plants with one or more ascalosides to prevent or mitigate the phytotoxic effects of pesticides such as fungicides, antimicrobial agents, insecticides, nutritional compositions, herbicides, and other components of pesticide formulations such as solvents, additives, and adjuvants known to be phytotoxic.

[0044] In one embodiment, the disclosure provides a method for treating plants with ascaloside to reduce the phytotoxic effects of pesticides.

[0045] In another aspect, the disclosure provides a composition comprising ascaloside useful for treating plants to reduce the phytotoxic effects of pesticides.

[0046] Before describing these methods and compositions in more detail, we will first explain ascaloside in more detail.

[0047] Ascaloside Ascaloside is a derivative of the sugar ascarilose, a dideoxy sugar lacking hydroxyl groups at positions 3 and 6. Ascaloside is represented by formula I: [ka] It has the general structure shown in the formula, where, Z is replaced by C of any choice. 2-40 It is an aliphatic group, R a and R b Each of these independently corresponds to -H or C 1-20 aliphatic, C 1-20 Ashiru, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bond functional group, sulfur bond functional group, silicon bond functional group, C 2-20 Carbonate (e.g., partial C(O)OR) c ), C 2-20 Carbamates (e.g., partial-C(O)N(R) c )2), C 2-20 Thioesters (e.g., partial-C(S)R) c ), C 2-20 Thiocarbonates (e.g., partial-C(S)OR c ), C 2-20 Dithiocarbonates (e.g., partial-C(S)SR) c ), C 1-20 Thiocarbamates (e.g., partial-C(S)N(R) c )2) A portion that is optionally substituted from the group consisting of a sugar portion, a peptide, a polymer chain, or bond to another ascaloside molecule or linkage via a carbon-containing linker portion, and each R c However, in each occurrence, independently, -H and C are substituted by any choice.1-12 Aliphatic, C substituted by choice 1-12 Selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain, or linkage to another ascaloside molecule or via a carbon-containing linker moiety, R a and R b However, together they can form an optionally substituted ring that optionally contains one or more heteroatoms and optionally contains one or more unsaturated sites.

[0048] In a particular embodiment, Z is (i)-CH(CH3)-R 1 (R 1 This is C, which has been replaced by an optional substitution. 1-40 (It is an aliphatic group.) (ii)-CH(CH3)-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted. 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety.) (iii)-CH(CH3)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety.) (iv)-CH(CH3)-(CH2) n -CH(OH)-CH2-CO2R 2 (n is an integer from 1 to 40, R2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety.) (v)-CH(CH3)-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety.) (vi)-(CH2) n -CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety.) (vii)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 (This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety.) (viii)-(CH2)n -CH(OH)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted. 1-20 Aliphatic group, optionally substituted C 1-20 This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaloside molecule via a carbon-containing linker moiety, or (ix)-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 This includes a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another askaloside molecule via a carbon-containing linker moiety.

[0049] In a particular embodiment, Z is (x)-CH(CH3)-(CH2) n -CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xi)-CH(CH3)-(CH2) n -CH=CH-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20(This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xii)-CH(CH3)-(CH2) n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xiii)-CH(CH3)-(CH2) n -C(O)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xiv)-(CH2) n -CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xv)-(CH2) n -CH=CH-CON(R 3 )2(n is an integer from 1 to 40, and each R3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xvi)-(CH2) n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 (This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another askaloside molecule via a carbon-containing linker moiety), (xvii)-(CH2) n -C(O)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 This may be a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a link to another ascaloside molecule via a carbon-containing linker moiety, or (xviii) Optionally unsaturated and optionally substituted C, terminated at a chain end containing a nitrogen-containing functional group, an oxygen-containing functional group, or a sulfur-containing functional group. 2-40 It is a side chain.

[0050] As defined above and described herein, in some embodiments, Z comprises a nitrogen, oxygen, or sulfur-containing functional group. It will be understood that “oxygen-containing functional group” means a moiety containing one or more oxygen atoms (e.g., carbonyl-containing groups such as esters, aldehydes, carboxylic acids, and ketones; ethers, hydroxyls, and heterocycles containing one or more oxygen atoms and / or one of the aforementioned functional groups); “nitrogen-containing functional group” means a moiety containing one or more nitrogen atoms (e.g., amines, amides, carbamates, imines, ureas, oximes, amidines, guanidines, nitriles, azo groups, azides, and heterocycles containing one or more nitrogen atoms and / or one of the aforementioned functional groups); and “sulfur-containing functional group” means a moiety containing one or more sulfur atoms (e.g., thioethers, sulfones, sulfonic acids, sulfoxides, thiols, thiocyanates, or disulfides).

[0051] In some embodiments, Z is optionally unsaturated and optionally substituted C, which terminates at a chain end containing an oxygen-containing functional group. 2-40 It is a side chain. In certain embodiments, Z is optionally unsaturated and optionally substituted with a chain terminus containing a carboxylic acid. 2-40 It is a side chain. In certain embodiments, Z is optionally unsaturated and optionally substituted with C, which terminates at the chain end containing an aldehyde. 2-40 It is a side chain. In certain embodiments, Z is optionally unsaturated and optionally substituted with C, which terminates at the chain end containing an ester. 2-40 It is a side chain. In some embodiments, Z-CO2R 2 A chain terminator that terminates with a C, which is optionally unsaturated and optionally substituted. 2-40 Side chain. In some embodiments, Z is optionally unsaturated and optionally substituted with C, ending at a chain end containing -CO2H. 2-40 It is a side chain. In some embodiments, Z is optionally unsaturated and optionally substituted with C, which terminates at a chain end containing -CO2CH3. 2-40 It is a side chain. In some embodiments, Z is -CON(R 3) terminates at the end of the chain containing 2, optionally unsaturated and optionally substituted C 2-40 It is a side chain. In some embodiments, Z is -N(R 3 ) terminates at the end of the chain containing 2, optionally unsaturated and optionally substituted C 2-40 It is a side chain. In some embodiments, Z is optionally unsaturated and optionally substituted with C, which terminates at a chain end containing an ester containing a linker moiety covalently bonded to one or more additional askaloside molecules. 2-40 It is a side chain.

[0052] As described above, the ascarilose sugar portion in the provided compound can be substituted or unsubstituted (i.e., functional groups other than -OH may be present at the 2nd and 4th positions of the sugar, or in other words, in any of the formulas herein, the variable R a and / or R b (This can be anything other than -H).

[0053] As defined above and as described herein, R a and R b Each of these is independently -H or C 1-20 aliphatic, C 1-20 Ashiru, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bond functional group, sulfur bond functional group, silicon bond functional group, C 2-20 Carbonate (e.g., partial C(O)OR) c ), C 2-20 Carbamates (e.g., partial-C(O)N(R) c )2), C 2-20 Thioesters (e.g., partial-C(S)R) c ), C 2-20 Thiocarbonates (e.g., partial-C(S)OR c ), C 2-20 Dithiocarbonates (e.g., partial-C(S)SR) c ), C 1-20 Thiocarbamates (e.g., partial-C(S)N(R) c2) A portion that is optionally substituted from the group consisting of a sugar portion, a peptide, a polymer chain, or a linkage to an ascaloside molecule or a carbon-containing linker portion.

[0054] In a particular embodiment, R a is -H. In a particular embodiment, R b is -H. In a particular embodiment, R a and R b They are the same. In a particular embodiment, R a and R b Both are -H. In a particular embodiment, R a and R b They are different. In a particular embodiment, R a is -H, and R b is anything other than -H. In a particular embodiment, R a is anything other than -H, and R b is -H. In a particular embodiment, R a is -H, and R b is a p-hydroxybenzoate. In certain embodiments, R a is -H, and R b is indole-3-carboxylate. In certain embodiments, R a is -H, and R b is (E)-2-methyl-2-butenoate. In certain embodiments, R a , is -H, R b is picolinate. In a particular embodiment, R a is -H, and R b is nicotinate. In a particular embodiment, R a is -H, and R b is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, R a is -H, and R b R is 4-((4-hydroxyphenylethyl)amino)-4-oxobutanoate. In certain embodiments, R aThis includes glycosides, amino acids, peptides, or nucleotides. In certain embodiments, R b This includes glycosides, amino acids, peptides, or nucleotides. In certain embodiments, R a This includes linking to a second ascaloside molecule. In certain embodiments, R b This includes linking to an askaloside molecule. In certain embodiments, R a It contains sugar. In a particular embodiment, R b It contains sugar.

[0055] In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-20 It is aliphatic. In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-6 It is aliphatic. In some embodiments, R a C 1-20 It is aliphatic. In some embodiments, R a C 1-6 It is aliphatic. In some embodiments, R a R is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or t-butyl. In some embodiments, R a C 1-20 In some embodiments, R a is -C(O)R c In some embodiments, R a is -C(O)H. In some embodiments, R a is -C(O)CH3. In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-20 It is heteroaliphatic. In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-6 It is heteroaliphatic. In some embodiments, R a C 1-20 It is heteroaliphatic. In some embodiments, R a C 1-6It is heteroaliphatic. In some embodiments, R a R is an optionally substituted 3-membered and 8-membered saturated or partially unsaturated heterocycline having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R a R is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocycline having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R a is an aryl that has been optionally replaced. In some embodiments, R a R is a phenyl compound that is optionally substituted. In some embodiments, R a R is phenyl. In some embodiments, R a R is an optionally substituted heteroaryl group. In some embodiments, R a R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R a R is an optionally substituted 8-12 member heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R a This is C, which has been replaced by an optional substitution. 2-20 It is a carbonate. In some embodiments, R a is -C(O)OR c In some embodiments, R a This is C, which has been replaced by an optional substitution. 2-20 It is a carbamate. In some embodiments, R a is -C(O)N(R c )2. In some embodiments, R a This is C, which has been replaced by an optional substitution. 2-20 It is a thioester. In some embodiments, R a is -C(S)R c In some embodiments, R a This is C, which has been replaced by an optional substitution. 2-20It is a thiocarbonate. In some embodiments, R a is -C(S)OR c In some embodiments, R a This is C, which has been replaced by an optional substitution. 2-20 It is a dithiocarbonate. In some embodiments, R a is -C(S)SR c In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-20 It is a thiocarbamate. In some embodiments, R a is -C(S)N(R c )2.

[0056] In some embodiments, R a This is an optionally substituted hydroxyl protecting group. Suitable hydroxyl protecting groups are well known in the art, as seen in Protecting Groups in Organic Synthesis, TW Greene and PGMWuts, 3 rd This includes those described in detail in edition, 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), triisopropylsilyloxymethyl (TOM), and triisopropylsilyl (TIPS) ethers), methyl ethers, and ethoxyethyl ethers. In some embodiments, R a is -OR c That is the case.

[0057] In some embodiments, R aR is an optionally substituted phosphorus-bonded functional group. As used herein, “phosphorus-bonded functional group” will be understood to refer to a moiety containing one or more phosphorus atoms (e.g., phosphine, phosphodiester, phosphonic acid, phosphoric acid). In some embodiments, R a R is an optionally substituted sulfur-bonded functional group. As used herein, “sulfur-bonded functional group” will be understood to refer to a moiety containing one or more sulfur atoms (e.g., thioethers, sulfones, sulfonic acids, sulfoxides, thiols, thiocyanates, or disulfides). In some embodiments, R a This is a silicon-bonded functional group that has been optionally substituted. As used herein, “silicon-bonded functional group” will be understood to refer to a moiety containing one or more silicon atoms (e.g., silanol, thuroxide, siloxane, silyl ether, silyl chloride, silyl hydrogenate, silene, or silole).

[0058] In some embodiments, R a R is an optionally substituted sugar moiety. In some embodiments, R a is a peptide that has been optionally substituted. In some embodiments, R a R is a polymer chain that has been optionally substituted. In some embodiments, R a This is a bond to the askaloside molecule or a linkage via a carbon-containing linker moiety. In some embodiments, R a This includes ascaloside, and optionally substituted C 1-6 It is aliphatic or heteroaliphatic.

[0059] In some embodiments, R b This is C, which has been replaced by an optional substitution. 1-20 It is aliphatic. In some embodiments, R b This is C, which has been replaced by an optional substitution. 1-6 It is aliphatic. In some embodiments, R b C 1-20 It is aliphatic. In some embodiments, R b C 1-6It is aliphatic. In some embodiments, R b R is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or t-butyl. In some embodiments, R b C 1-20 In some embodiments, R b is -C(O)R c In some embodiments, R b is -C(O)H. In some embodiments, R b is -C(O)CH3. In some embodiments, R b This is C, which has been replaced by an optional substitution. 1-20 It is heteroaliphatic. In some embodiments, R b This is C, which has been replaced by an optional substitution. 1-6 It is heteroaliphatic. In some embodiments, R b C 1-20 It is heteroaliphatic. In some embodiments, R b C 1-6 It is heteroaliphatic. In some embodiments, R b R is an optionally substituted 3-membered and 8-membered saturated or partially unsaturated heterocycline having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R b R is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocycline having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R b is an aryl that has been optionally replaced. In some embodiments, R b R is a phenyl compound that is optionally substituted. In some embodiments, R b R is phenyl. In some embodiments, R b R is an optionally substituted heteroaryl group. In some embodiments, R b R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rb R is an optionally substituted 8-12 member heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R b This is C, which has been replaced by an optional substitution. 2-20 It is a carbonate. In some embodiments, R b is -C(O)OR c In some embodiments, R b This is C, which has been replaced by an optional substitution. 2-20 It is a carbamate. In some embodiments, R b is -C(O)N(R c )2. In some embodiments, R b This is C, which has been replaced by an optional substitution. 2-20 It is a thioester. In some embodiments, R b is -C(S)R c In some embodiments, R b This is C, which has been replaced by an optional substitution. 2-20 It is a thiocarbonate. In some embodiments, R b is -C(S)OR c In some embodiments, R b This is C, which has been replaced by an optional substitution. 2-20 It is a dithiocarbonate. In some embodiments, R b is -C(S)SR c In some embodiments, R a This is C, which has been replaced by an optional substitution. 1-20 It is a thiocarbamate. In some embodiments, R b is -C(S)N(R c )2.

[0060] In some embodiments, R b This is an optionally substituted hydroxyl protecting group.

[0061] In some embodiments, R b R is an optionally substituted phosphorus-bonded functional group. In some embodiments, R bR is an optionally substituted sulfur-bonded functional group. In some embodiments, R b This is a silicon-bonded functional group that has been optionally substituted.

[0062] In some embodiments, R b R is an optionally substituted sugar moiety. In some embodiments, R a is a peptide that has been optionally substituted. In some embodiments, R b R is a polymer chain that has been optionally substituted. In some embodiments, R b This is a bond to the askaloside molecule or a linkage via a carbon-containing linker moiety. In some embodiments, R b This includes ascaloside, and optionally substituted C 1-6 It is aliphatic or heteroaliphatic.

[0063] In some embodiments, R a and R b Together, they can form an optionally substituted ring that optionally contains one or more heteroatoms and optionally contains one or more unsaturated sites. In some embodiments, R a and R b Together, they can form optionally substituted 3-12 membered monocyclic or bicyclic saturated or partially unsaturated carbocyclyl or heterocyclyl rings having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R a and R b These can combine to form optionally substituted 5-12 membered monocyclic or bicyclic aryl or heteroaryl rings having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0064] As defined above and described herein, each R c In each occurrence, independently, -H is replaced by C of any choice. 1-12 Aliphatic, C substituted by choice 1-12The linkage can be selected from heteroaliphatic molecules, optionally substituted aryl molecules, optionally substituted heteroaryl molecules, polymer chains, or linkage to another ascaloside molecule via a carbon-containing linker moiety.

[0065] In some embodiments, R c In each occurrence, independently, -H is replaced by C of any choice. 1-12 Aliphatic, C substituted by choice 1-12 The selection is made from heteroaliphatic compounds, optionally substituted aryl compounds, and optionally substituted heteroaryl compounds.

[0066] In some embodiments, R c The appearance of is -H. In some embodiments, R c This is C, which has been replaced by an optional substitution. 1-12 It is an aliphatic group. In some embodiments, R c This is C, which has been replaced by an optional substitution. 1-6 It is an aliphatic group. In some embodiments, R c This is C, which has been replaced by an optional substitution. 1-12 It is a heteroaliphatic group. In some embodiments, R c This is C, which has been replaced by an optional substitution. 1-6 It is a heteroaliphatic group. In some embodiments, R c R is an optionally substituted 3-membered and 8-membered saturated or partially unsaturated heterocycline having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R c R is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocycline having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R c R is an optionally substituted aryl group. In some embodiments, R c R is a phenyl compound that is optionally substituted. In some embodiments, R c R is phenyl. In some embodiments, R c R is an optionally substituted heteroaryl group. In some embodiments, Rc R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R c It is an optionally substituted 8-12 membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0067] As defined above and as described herein, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 Aliphatic group, optionally substituted C 1-20 The linkage is to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another askaloside molecule, or to a linkage via a carbon-containing linker moiety. In some embodiments, R 2 -H, C which is replaced by an optional substitution. 1-20 Aliphatic group, optionally substituted C 1-20 These are heteroaliphatic groups, optionally substituted aromatic groups, or optionally substituted heteroaryl groups.

[0068] In some embodiments, R 2 is -H. In some embodiments, R 2 R is a metal cation. In some embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-20 It is an aliphatic group. In some embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-6 It is an aliphatic group. In some embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-20 It is a heteroaliphatic group. In some embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-6 It is a heteroaliphatic group. In some embodiments, R 2R is an optionally substituted 3-membered and 8-membered saturated or partially unsaturated heterocycline having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 2 R is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocycline having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 2 R is an optionally substituted aromatic group. In some embodiments, R 2 R is a phenyl compound that is optionally substituted. In some embodiments, R 2 R is phenyl. In some embodiments, R 2 R is an optionally substituted heteroaryl group. In some embodiments, R 2 R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 2 It is an optionally substituted 8-12 membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0069] In some embodiments, R 2 It is a glycoside. A glycoside is understood to refer to a portion containing sugar that is linked to another functional group via a glycosidic bond.

[0070] In some embodiments, R 2 R is a nucleotide. In some embodiments, R 2 is adenosine monophosphate, cytidine monophosphate, guanosine monophosphate, or uridine monophosphate. In some embodiments, R 2 These are deoxyadenosine monophosphate, deoxycytidine monophosphate, deoxyguanosine monophosphate, or deoxythymidine monophosphate.

[0071] In some embodiments, R 2This is bonding to another askaloside molecule or linking via a carbon-containing linker moiety. In some embodiments, R 2 This includes ascaloside, and optionally substituted C 1-6 It is aliphatic or heteroaliphatic.

[0072] As defined above and described herein, each R 3 These are independently replaced by -H and C of any choice. 1-20 Aliphatic group, optionally substituted C 1-20 The linkage is to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another askaloside molecule, or to a linkage via a carbon-containing linker moiety. In some embodiments, each R 3 These are independently -H and C 1-8 Selected from aliphatic species. In some embodiments, one R 3 is -H, and the other R 3 is anything other than -H. In some embodiments, R 3 None of these are -H. In some embodiments, each R 3 is -H. In some embodiments, R 3 The appearance of C is a substitution of C by choice. 1-20 It is an aliphatic group. In some embodiments, R 3 The appearance of C is a substitution of C by choice. 1-6 It is an aliphatic group. In some embodiments, R 3 The appearance of C is a substitution of C by choice. 1-20 It is a heteroaliphatic group. In some embodiments, R 3 The appearance of C is a substitution of C by choice. 1-6 It is a heteroaliphatic group. In some embodiments, R 3 R is an optionally substituted 3-membered and 8-membered saturated or partially unsaturated heterocycline having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 3is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 3 appearance is an optionally substituted aryl group. In some embodiments, R 3 is an optionally substituted phenyl. In some embodiments, R 3 is phenyl. In some embodiments, R 3 is an optionally substituted heteroaryl group. In some embodiments, R 3 is an optionally substituted 5- to 6-membered heteroaryl having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 3 is an optionally substituted 8- to 12-membered heteroaryl having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0073] In certain embodiments, R a and R b are the same. In certain embodiments, R a and R b are both -H.

[0074] In certain embodiments, R a and R b are different. In certain embodiments, R a is -H and R b is other than -H. In certain embodiments, R a is other than -H and R b is -H. In certain embodiments, R a is -H and R b is p-hydroxybenzoate. In certain embodiments, R a is -H and R b is indole-3-carboxylate. In certain embodiments, R a is -H and R bis (E)-2-methyl-2-butenoate. In certain embodiments, R a is -H, and R b is picolinate. In certain embodiments, R a is -H, and R b is nicotinate. In certain embodiments, R a is -H, and R b is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, R a is -H, and R b is 4-((4-hydroxyphenylethyl)amino)-4-oxobutanoate.

[0075] In certain embodiments, R a and R b are both -H, and Z is selected from the formulas defined in (i) to (xviii) above. In certain embodiments, R a and R b are both -H, and Z conforms to formula (i) above. In certain embodiments, R a and R b are both -H, and Z conforms to formula (ii) above. In certain embodiments, R a and R b are both -H, and Z conforms to formula (iii) above. In certain embodiments, R a and R b are both -H, and Z conforms to formula (iv) above. In certain embodiments, R a and R b are both -H, and Z conforms to formula (v) above. In certain embodiments, R a and R b are both -H, and Z conforms to formula (vi) above. In certain embodiments, R a and R b are both -H, and Z conforms to formula (vii) above. In certain embodiments, R a and Rb Both are -H, and Z conforms to equation (viii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (ix) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (x) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xi) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xiii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xiv) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xv) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xvi) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xvii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (xviii) above.

[0076] In a particular embodiment, R 2 is -H. In a particular embodiment, R 2 is a metal cation. In a particular embodiment, R 2 is an organic cation (for example, a nitrogen or phosphorus-centered cationic group). In certain embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-20It is an aliphatic group. In certain embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-12 It is an aliphatic group. In certain embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-8 It is an aliphatic group. In certain embodiments, R 2 This is C, which has been replaced by an optional substitution. 1-6 It is an aliphatic group. In certain embodiments, R 2 R is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In certain embodiments, R 2 R is an optionally substituted aromatic group. In certain embodiments, R 2 is a glycoside. In a particular embodiment, R 2 It contains amino acids. In certain embodiments, R 2 It contains peptides. In certain embodiments, R 2 It contains nucleotides.

[0077] In a particular embodiment, at least one R 3 is -H. In certain embodiments, both R 3 The base is -H. In certain embodiments, at least one R 3 This is C, which has been replaced by an optional substitution. 1-20 It is an aliphatic group. In certain embodiments, both R 3 The base is a C that can be the same or different, and can be substituted by any choice. 1-20 It is an aliphatic group. In certain embodiments, at least one R 3 This is C, which has been replaced by an optional substitution. 1-12 It is an aliphatic group. In certain embodiments, at least one R 3 This is C, which has been replaced by an optional substitution. 1-8 It is an aliphatic group. In certain embodiments, at least one R 3 This is C, which has been replaced by an optional substitution. 1-6 It is an aliphatic group. In certain embodiments, at least one R 3R is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In certain embodiments, at least one R 3 is -CH2CH2OH. In certain embodiments, at least one R 3 is -CH2CH2OR 2 That is. R 2 These are as defined in the genera and subgenera herein. In certain embodiments, at least one R 3 is an optionally substituted aromatic group. In certain embodiments, at least one R 3 It contains a glycoside. In a particular embodiment, at least one R 3 It contains amino acids. In certain embodiments, at least one R 3 at least one R 3 It contains peptides. In certain embodiments, at least one R 3 It contains nucleotides.

[0078] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x is an integer from 1 to 22, R a , R b , and R 2 Each of these is as defined above and in the genera and subgenera herein.

[0079] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x, R a , and R b Each of these is as defined above and in the genera and subgenera herein.

[0080] In a particular embodiment, ascaroside is [ka] selected from the group consisting of, wherein y is an integer from 1 to 20, R a , R b , and each of R 2 is as defined in the above and the genera and subgenera of this specification.

[0081] In certain embodiments, the ascaloside is

Chemical formula

[0082] In certain embodiments, the ascaloside is

Chemical formula

[0083] In certain embodiments, the ascaloside is

Chemical formula

[0084] In certain embodiments, the ascaloside is

Chemical formula

[0085] In a particular embodiment, ascaroside is [ka] A group consisting of is selected, where y is as defined above and in the genera and subgenera of this specification.

[0086] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x is an integer from 1 to 22, R a , R b , and R 3 Each of these is as defined above and in the genera and subgenera herein.

[0087] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x and R 3 Each of these is as defined above and in the genera and subgenera herein.

[0088] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where y is an integer from 1 to 20, R a , R b , and R 3 Each of these is as defined above and in the genera and subgenera herein.

[0089] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, in the formula, y and R 3Each of these is as defined above and in the genera and subgenera herein.

[0090] In one embodiment, an ascaloside useful in the context of this disclosure has a general structure (I), where Z is -CH(CH3)-(CH2) n -CO2R 2 And n is an integer from 1 to 40, R 2 C is a -H, a metal cation, or optionally substituted C 1-20 These may be aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides, and can be used to inhibit the growth of human pathogenic bacteria within or on plants.

[0091] In one embodiment, an ascaloside useful in the context of this disclosure has a general structure (I), where Z is -CH(CH3)-(CH2) n -CH=CH-CO2R 2 And n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted. 1-20 These are aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.

[0092] Specific ascalosides useful in the context of this disclosure include, but are not limited to, ascr#7 and ascr#18. [ka]

[0093] In certain embodiments, the ascaloside used in the provided method and composition is selected from the group consisting of ascr#9, ascr#12, ascr#14, ascr#1, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, ascr#24, ascr#26, ascr#28, ascr#30, ascr#32, ascr#34, and ascr#36. In certain embodiments, the ascaloside used in the provided method is selected from the group consisting of ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. In certain embodiments, the ascaloside used in the provided method is selected from the group consisting of ascr#9, ascr#14, ascr#10, and ascr#18.

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

[0095] In a particular embodiment, the ascaloside used in the provided method and composition 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, the ascaloside used in the provided method and composition 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, the ascaloside used in the provided method and composition 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, the ascalosides used in the methods and compositions provided are ascaloside salts disclosed in International Publication WO2023 / 220174 filed on 10 May 2023, or ascalosides modified to provide extended release of the active ingredient disclosed in International Publication WO2023 / 212362 filed on 28 April 2023, both of which are incorporated herein by reference in their entirety.

[0099] Ascalosides can be obtained from natural sources (e.g., nematodes) or they can be prepared synthetically. Ascalosides can be prepared synthetically, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascarilose. An exemplary method for preparing ascalosides includes providing 1-O-substituted rhamnose as a starting material, forming a monosulfonate ester on the 3-OH group of the starting material, and treating the monosulfonate ester with a hydride source to form 1-O-substituted ascarilose. In certain embodiments, the formation of the monosulfonate ester is carried out on a substrate that does not contain a hydroxyl protecting group at the 2 or 4 position of the rhamnose starting material. In certain embodiments, such a method includes contacting the starting material with a sulfonating agent (i.e., a sulfonyl halide, sulfonic anhydride, or similar reagent) in the presence of a Lewis acid. Specific details relating to the synthesis of 1-O-substituted ascarilose can be found in PCT application publication WO / 2022 / 024067, which is incorporated herein by reference.

[0100] method In one embodiment, the disclosure provides a method for mitigating the phytotoxic effects of pesticides applied to crop plants. All methods provided involve treating crop plants with one or more ascalosides, although details regarding when and how the ascaloside treatment is carried out may vary.

[0101] Ascaloside can be applied to plants by various means, and since plants are known to respond systemically to ascaloside, the mode of application is not particularly limited. Non-limiting examples of preferred modes of application of ascaloside include seed treatment, foliar spraying or application, root immersion or drenching, soil application, application of time-release formulations, injection into stems or trunks, or application of compositions for absorption through the bark (e.g., stems, trunks, branches, or vines).

[0102] In certain embodiments, the provided method involves the simultaneous application of one or more ascalosides and one or more pesticides to a crop. Simultaneous application, in some embodiments, may include applying two separate formulations (one containing one or more ascalosides and the other containing one or more pesticides) at close intervals (e.g., substantially simultaneously or within about 1 minute, 5 minutes, 10 minutes, 30 minutes, 1 hour, 2 hours, 6 hours, 12 hours, 24 hours, or 2 days) to each other. When one or more ascalosides and pesticides are applied separately, one or more ascalosides may be applied before or after the application of pesticides, and may be applied by the same or different means.

[0103] Simultaneous application, in some embodiments, may include combining one or more ascalosides with one or more pesticides shortly before application to plants (e.g., immediately before application). One preferred method for administering one or more ascalosides and one or more pesticides is to mix the components in situ, for example, by adding one or more ascalosides to a tank mixture containing one or more pesticides.

[0104] In some embodiments, the present disclosure provides a method for mitigating the phytotoxic effects of a pesticide, comprising administering ascaloside to a plant, a plant part, or soil surrounding a plant or plant part, wherein the plant, a plant part, or soil surrounding a plant or plant part has been or is currently exposed to the pesticide.

[0105] In some embodiments, the present disclosure provides a method for mitigating the phytotoxic effects of a pesticide, comprising administering the pesticide to a plant, a plant part, or soil surrounding a plant or plant part, wherein the plant, a plant part, or soil surrounding a plant or plant part has been or is currently exposed to ascaloside.

[0106] In other embodiments, the components to be applied simultaneously may be combined at an even earlier point in time. In such embodiments, an agricultural formulation is prepared, which comprises one or more ascalosides and one or more pesticides, optionally combined with one or more inactive components. Advantageously, in some embodiments, the combinations of one or more ascalosides and one or more pesticides provided herein are compatible with each other, and the resulting formulation can exhibit stability over long periods (e.g., more than one week, more than one month, more than two months, more than three months, more than four months, more than five months, or more than six months) under standard conditions (e.g., room temperature, housed in one or more closed systems of relative humidity zones). Demonstration of stability in this context may vary. For example, in some embodiments, no significant separation is observed with the naked eye. In some embodiments, no significant change in the amount of pesticides and / or ascalosides is observed via conventional methods (e.g., spectroscopy). In some embodiments, no significant chemical degradation of pesticides and / or ascalosides is observed using conventional methods (e.g., spectroscopy).

[0107] In certain embodiments, the provided method includes the application of one or more ascalosides and one or more pesticides to a crop at different times. This may include the preventive application of ascalosides(or ascalosides) before the application of pesticides(or pesticides) (for example, ascalosides may be applied about 3 days, 5 days, 1 week, 2-3 weeks, 4-6 weeks, or 6-10 weeks before the application of pesticides). In certain embodiments, ascalosides(or ascalosides) may be applied after the application of pesticides (for example, ascalosides may be applied about 3 days, 5 days, or 1 week after the application of pesticides).

[0108] In certain embodiments, the provided method involves the application of one or more ascalosides and one or more pesticides to a crop via different methods. For example, ascalosides may be applied to the crop as a seed treatment (e.g., before planting), while one or more pesticides may be applied by different means such as foliar spraying, spraying, or soil application. In another example, ascalosides may be applied to the soil (i.e., as a trench or furrow application), while one or more pesticides may be applied by different means such as seed treatment, foliar spraying, or spraying. For woody perennial crops such as fruits, nuts, and ornamental plants, ascalosides may be applied systemically (i.e., via injection or by applying an absorbable composition to the trunk, branches, or vines), while one or more pesticides may be applied by different means such as foliar spraying, soil application, or spraying.

[0109] In certain embodiments, the provided method involves applying ascaloside(s) to a crop more than once (e.g., 2 to about 6 times) during the growing season. The timing and / or manner of each ascaloside application in such a method may vary. For example, one or more applications may be applied concurrently with pesticides, may be preventative applications applied before pesticide(s), or may be applications performed after one or more pesticide applications. In some embodiments, the provided method includes combinations of such timing variations. In some embodiments, the provided method may include application of ascaloside by different means during the growing season (e.g., foliar spray following seed treatment, or spray following systemic application).

[0110] In certain embodiments, the method provided is characterized in that the application of ascaloside results in a reduction of phytotoxic damage to crops compared to the use of pesticides alone without the application of ascaloside. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10%. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90%. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are substantially absent. In certain embodiments, one or more phytotoxic symptoms are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or distorted plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any two or more combinations thereof.

[0111] pesticides The pesticides in the various methods and compositions provided herein encompass all compounds used on crops that may exhibit phytotoxic effects on plants under at least some conditions. Such pesticides include, but are not limited to, antifungal agents (also called fungicides), antifungal agents (also called fungicides), insecticides (also called insecticides), and anthelmintics (also called nematicides). Understanding that the phytotoxic effects mitigated by the provided compositions and methods are non-target effects that adversely affect treated crops (i.e., herbicide-resistant crop plants) rather than intended phytotoxic effects on target plants (i.e., weeds), the pesticides may also include herbicides. The pesticides in the methods and formulations provided may include nutrients or micronutrient compositions. The pesticides in the provided methods and formulations may also contain other materials present in pesticide formulations, such as solvents, adjuvants, wetting agents, surfactants, preservatives, compatibilizers, stabilizers, dyes, antifreezes, and anticoagulants, many of which are known to have some degree of phytotoxicity. In some cases, phytotoxicity arises from the application of combinations of pesticides, even though each pesticide alone may not cause phytotoxic effects.

[0112] The antimicrobial agents that may be included in the pesticides in the methods and formulations of this disclosure are not particularly limited. Suitable pesticides may be prophylactic or curative, may have monosite or multisite activity, may be narrow-spectrum or broad-spectrum in practice, and may be organic or inorganic. Pesticides may be chemical or biological. In some embodiments, pesticides are natural and have active ingredients including, but not limited to, sulfur, lime-sulfur, copper (e.g., in the form of copper sulfate), oils (e.g., horticultural oils, neem oil, rosemary oil, and jojoba oil), bicarbonates (e.g., sodium bicarbonate, potassium bicarbonate, and ammonium bicarbonate), and combinations thereof.

[0113] A certain broad chemical class of fungicidal compounds contained in pesticides in certain embodiments disclosed herein includes, but is not limited to, substituted benzenes, thiocarbamates, dithiocarbamates, thiophthalimide copper compounds, nitriles / benzonitriles / chloronitriles, benzimidazoles, dicarboximides, carboxamides / anilides, strobilurins, phenylpyrroles, aromatic hydrocarbons, polyoxins, pyridineamines, phenylamides, cyanoimidazoles, phosphonates, and combinations thereof. The fungicides useful in the various formulations and methods described herein can also be defined by their mode of action, for example: mitotic disruptors (e.g., thiophanates such as thiophanate-methyl); cell membrane disruptors (e.g., triazoles such as cyproconazole, difenoconazole, flutriafor, mefentrifluconazole, metconazole, propiconazole, tebuconazole, and tetraconazole, as well as triazolinthions such as prothioconazole); respiratory inhibitors (e.g., succinate dehydrogenase inhibitors / carboxamides, e.g., pyridinecarboxamide (e.g., boscalid), pyridinyl-ethylbenzamide (e.g., fluopyram), and pyrazole-4-carboxamide (e.g., benzovinyl Diflupir, bixafen, fluxapyroxad, penthiopyrad, pidflumetofen), as well as quinone external inhibitors / strobilurins, e.g., methoxyacrylates (e.g., azoxystrobin and picoxystrobin), dihydro-dioxazines (e.g., fluoxastrobin), methoxy-carbamates (e.g., pyraclostrobin), and oxyimino-acetates (e.g., trifluoxystrobin); non-conjugates of oxidative phosphorylation (e.g., 2,6-dinitroanilines such as fluazinam); fungicides of unknown activity (e.g., phosphonates such as phosphates and salts); and fungicides with multi-site contact activity (e.g., inorganic fungicides such as chloronitriles / phthalonitriles such as copper salts and chlorothalonil).

[0114] Suitable specific agents to be included in pesticides include acibenzolar, acibenzolar-S-methyl, Agrobacterium radiobacter, aldicarb, aliphatic petroleum distillates, allyl isothiocyanate, aluminum tris, amethoctrazine, 2-aminobutane, Ampelomyces quisqualis, anilazine, Aureobasidium pullulans (e.g., strains DSM14940 and 14941), azadirachtin, azoxystrobin, Bacillus amyloliquefaciens (e.g., strains D747 or F727), Bacillus firmus (e.g., strain I-1582), Bacillus mycoides (e.g., isolate J), ​​Bacillus pumilus (e.g., strain QST2808), Bacillus subtilis (e.g., strain IAB / BS03, strain QST713, strain BG03, or strain MBI600), basic cupric carbonate, benomyl, benzovindiflupyr, bifenazate, bixafen, BLAD, borax, boric acid, boscalid, Burkholderia cepacia, Candida oleophila, capric and caprylic acids, captahole, captan, carbendazim, carbofuran, carbon disulfide, carboxyne, chitin, chlorfenapyr, chlorine dioxide, chloroneb, chloropicrin, chlorothalonil, cinnamaldehyde, cyproconazole, clove oil, ConiothyriumMinitans (e.g., strain CON / M / 91-08), copper, copper ammonium complexes (e.g., tannic acid complex of copper ammonium carbonate and cupric ammonium picroformate), copper diammonium diacetate complex, copper hydroxide, copper octanoate, copper oxide, copper oxychloride, copper sulfate, cresol, cyazofamide, cyclohexane polymer, cycloheximide, cyflufenaamide, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diclone, dichloran, dichloropropene, dicofor, difenoconazole, difenoxazole, diphoratan, dimethomorph, demeton, dimethyl disulfide, dinocap, dodemorph acetate, dozin, epoxy Siconazole, etaboxam, etoprop, ethoxyquin, ethylene dibromide, etaboxam, etridiazole, famoxadone, phenamidone, phenaminosulf, phenamiphos, phenarimol, phenazaquin, fenbuconazole, fenhexamide, fenpyrazamine, phensulfotion, ferubam, fluazinam, fludioxonil, fluensulfone, fluopicolide, fluopyram, fluoxastrobin, fluquinconazole, flusilazole, fluthianil, flutolanil, flutriaform, fluxapyroxad, forpet, formaldehyde, fosetyl-A, gamma-aminobutyric acid, gibberellic acid, Gliocladium Catenalatum (e.g., strain J1446), Gliocladium virens, Harpin, Hexachlorobenzene, Horticultural mineral oil, Calcium hydroxide, Himexazole, Imazalil, Iodomethane, Ipconazole, Iprodione, Isofetamide, Jojoba oil, Kasugamycin, Kresoxim-methyl, L-Glutamic acid, Laminarin, Lime sulfur mixture, Mandestrobin, Mandipropamide, Maneb, Mancozeb, Mefenoxam, Mefentrifluconazole, Metalaxyl, Metam sodium, Metoconazole, Methyl bromide, Methylcyclopropene, Methylisothiocyanate, Metraphenone, Methyl bromide, Methylcyclopropene, Methylram, Mycrobutanil, MyrotheciumVerrucaria (e.g., strain AARC-0255), neem oil, oxadixyl, oxamyl, oxthioquinox, oxathiapiproline, oxycarboxyne, oxytetracycline, oxythioquinox, Paecilomyces lilacinus (e.g., strain 251), Pantoea agglomerans (e.g., strain E325), parinol, pentachloronitrobenzene (PCNB), penthiopyrad, peroxide, peroxyacetic acid, hydrogen peroxide, petroleum, phenylmercury acetate, phosphite, phosphorous acid, picoxystrobin, polyalkylene-modified heptamethyltrisiloxane, polyoxin D, polyoxin D zinc salt, potassium bicarbonate, potassium phosphite, potassium silicate, prohexadione calcium, propamocarb, propiconazole, prothioconazole, Pseudomonas aureofaciens, Pseudomonas Chloraphis (e.g., strain AFS009), Pseudomonas fluorescens, Pseudomonas syringae, Pidiflumetofen, Pyraclostrobin, Pyrimethanil, Pyriophenone, Quaternary ammonium, Quinoxyfen, Reynoutria sachalinensis, Rosemary oil, Saponin, Sedaxane, Sodium hypochlorite, Spiroxamine, Streptomyces griseoviridis (e.g., strain 61), Streptomycin, Sulfur, Swinglea glutinosa, Tebuconazole, Tetrathiocarbonate, Thiabendazole, Thiamethoxam, Thiophanate, Thiophanate-methyl, Thyrum, Thyme oil, Triadimephone, Triadimenol, Trichoderma asperellum (e.g., strain T34), Trichoderma gamsii, Trichoderma Examples include, but are not limited to, harzianum, trifloxystrobin, triflumazole, triforin, triphenyltin hydroxide, triticonazole, urea, Urocladium oudemansii (e.g., strain U3), vinclozoline, vanillazine, xylenol, zineb, ziram, zoxamide, and combinations thereof.

[0115] In some embodiments, the pesticide comprises or more commercially available antimicrobial agents, e.g., one or more fungicides. In some embodiments, such commercially available antimicrobial agents are fungicide mixtures. Commercially available antimicrobial agents are known in the art and include ABOUND® (Syngenta) containing azoxystrobin, ABSOLUTE® (Bayer Crop Science) containing tebuconazole and trifloxystrobin, ACADEMY® (Syngenta) containing difenoconazole and fludioxonil, ACTIGARD® (Syngenta) containing acibenzoral-S-methyl, ADAMENT® (Bayer Crop Science) containing tebuconazole and trifloxystrobin, and ALIETTE® (Bayer Crop) containing aluminum tris(O-ethylphosphonate). ALTO (Syngenta) containing cyproconazole, ALUMNI (Syngenta) containing thiabendazole, AMISTAR (Syngenta) containing azoxystrobin and difenoconazole, APROACH (DuPont) containing picoxystrobin and cypronazole, APROVIA (Syngenta) containing benzovindiflupir (alone or with propiconazole or difenoconazole), ARCHIVE (Syngenta) containing fludioxonil and azoxystrobin, CABRIO (Syngenta) containing pyraclostrobin, CANNONBALL (Syngenta) containing fludioxonil, and CARAMBA (Syngenta) containing metconazole. (BASF), CHAIRMAN® (Syngenta) containing fludioxonil and propiconazole, CHAMPION® (Nufarm) containing copper hydroxide and metallic copper equivalent, DELARO® (Bayer Crop) containing trifloxystrobin and prothioconazoleELATUS(Syngenta) containing azoxystrobin and benzovinyl; F500(Syngenta) containing strobilurin (BASF); FLINT(Syngenta) containing trifloxystrobin (Bayer Crop Science); FONTELIS(Syngenta) containing penthiopyrad (Corteva); GRADUATE(Syngenta) containing fludioxonil (alone or with azoxystrobin); INITUM(Syngenta) (BASF); INSPIRE(Syngenta) containing difenoconazole (alone or with cyprodinil or propiconazole); LUNA(Syngenta) containing fluopyram and pyrimethanil (Bayer Crop Science); MENTOR(Syngenta) containing propiconazole; MERTECT(Syngenta) containing thiabendazole; MINUET(Syngenta) containing Bacillus subtilis strain QST 713 (Bayer Crop Science) MIRAVIS® (Syngenta) containing pidflumetofen (alone or in combination with difenoconazole, propiconazole, fludioxonil, or azoxystrobin and propiconazole), OMETGA® (Syngenta) containing fluazinam, ORONDIS® (Syngenta) containing oxatiapiproline (alone or in combination with mefenoxam, chlorothalonil, or mandipropamide), PREVICUR® (Bayer Crop Science) containing propamocarb hydrochloride, PRISTINE® containing pyraclostrobin and boscalid, PROLINE® (Bayer Crop Science) containing prothioconazole, PROPULSE® (Bayer Crop Science) containing fluopyram and prothioconazole, PROSARO® (Bayer Crop Science) containing prothioconazole and tebuconazole PROVOST (registered trademark) (Bayer Crop Science), containing prothioconazole and tebuconazole.QUADRIS® (Syngenta) containing azoxystrobin (alone or in combination with chlorothalonil, mefenoxam, or difenoconazole), QUILT® (Syngenta) containing azoxystrobin and propiconazole, REGALIA® (Marrone BioInnovations) containing Reynoutria sachalinensis, REVUS® (Syngenta) containing mandipropamide (alone or in combination with difenoconazole), RIDOMIL® (Syngenta) containing mefenoxam (alone or in combination with chlorothalonil, copper OH, or mancozeb), SCALA® (Bayer Crop Science) containing pyrimethanil and 1,2-propanediol, SCHOLAR® (Syngenta) containing fludioxonil; SERENADE® (Bayer Crop) containing Bacillus subtilis strain QST713 STRATEGO (registered trademark) (Bayer Crop Science), containing propiconazole and trifloxystrobin; STADIUM (registered trademark) (Syngenta), containing azoxystrobin, fludioxonil, and difenoconazole; SWITCH (registered trademark) (Syngenta), containing cyprodinil and fludioxonil; TANOS (registered trademark) (DuPont (trademark)), containing famoxadone and cymoxanil; TILT (registered trademark) (Syngenta), containing propiconazole (alone or in combination with chlorothalonil); TOP (registered trademark) (Syngenta), containing difenoconazole; TRIVAPRO (registered trademark) (Syngenta), containing propiconazole, azoxystrobin, and benzovindiflupyr; UNIFORM (registered trademark) (Syngenta), containing azoxystrobin and mefenoxam; VANGARD (registered trademark) (Syngenta), containing cyprodinil; VELUM (registered trademark) (Bayer Crop Science), containing fluopyramThis includes, but is not limited to, VIBRANCE® (Syngenta) containing sedaxane, mefenoxam, and fludioxonil having thiabendazole or azoxystrobin, VYDATE® (DuPont®) containing oxamyl, and XEMIUM® (BASF) containing carboxamide.

[0116] In certain embodiments, a pesticide contains materials present in the formulation but not classified as “active ingredients,” and these inactive ingredients include materials such as solvents, surfactants, wetting agents, stabilizers, compatibilizers, dyes, and preservatives. One or more inactive ingredients, for example, one or more agrochemically acceptable carriers (also referred to as agrochemically acceptable or suitable adjuvants), are generally included in a pesticide formulation. The term “agrochemically acceptable carrier” includes any carrier suitable for administration to plants or soil, such as solutions (e.g., directly sprayable or dilutable solutions), emulsions (e.g., emulsion concentrates and diluted emulsions), wetting powders, suspensions, soluble powders, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, encapsulation in polymer materials, coatable pastes, natural and synthetic materials impregnated with active compounds, and conventional excipients in formulation technology, such as those used to form microencapsulations in polymer materials. In some embodiments, the agriculturally acceptable carrier may include surfactants, emulsifiers, oils, salts, and the like.

[0117] The pesticide composition may contain one or more agronomically acceptable carriers, such as liquid solvents or solid carriers. Other pesticides include, but are not limited to, surfactants including emulsifiers, dispersants, foaming agents, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, UV absorbers, weather stabilizers, plasticizers, release agents, fragrances, heat retention additives (e.g., silica), crosslinking agents, antioxidants, defoamers, buffers, pH adjusters, compatibility agents, drift control additives, bulking agents / thickeners, tackifiers, plant penetration agents, spreading agents, and wetting agents. In some embodiments, the pesticide includes wetting agents, emulsifiers, spreading agents, etc. The pesticide formulation includes concentrated forms in which the pesticide is present at a concentration of 2% to 98.0%, with the remaining components being agronomically acceptable carriers / adjuvants.

[0118] Such formulations, especially those containing less than 50 percent pesticide, can sometimes be used directly, but they can also be diluted with other agronomically acceptable carriers to form more diluted treatment formulations.

[0119] Pesticides contain "adjuvant surfactants" that can promote the deposition, wetting, and penetration of compounds into target crops and organisms. Examples of adjuvant surfactants include ethoxylated nonylphenol, ethoxylated synthetic or natural alcohols, esters, or sulfosuccinate salts, ethoxylated organosilicones, ethoxylated fatty amines, blends of surfactants with mineral or vegetable oils, crop oil concentrates (mineral oil (85%) + emulsifier (15%)), nonylphenol ethoxylate, benzyl cocoalkyldimethylquaternary ammonium salts; petroleum hydrocarbons, alkyl esters, organic acids, and anionic surfactant blends. Examples include, but are not limited to, C9-Cu alkyl polyglycosides, phosphate alcohol ethoxylates, natural primary alcohols (C12-C16) ethoxylates, di-sec-butylphenol EO-PO block copolymers, polysiloxane-methyl cap, nonylphenol ethoxylate + urea ammonium nitrate, emulsified methylated seed oils, tridecyl alcohol (synthetic) ethoxylate (8EO), tallow amine ethoxylate (15EO), and PEG(400)-dioleate-99.

[0120] The pesticide may also comprise an oil-in-water emulsion. In some embodiments, the pesticide comprises an organic solvent (i.e., an organic solvent that may be incorporated as an auxiliary liquid solvent in the pesticide formulation). Suitable liquid solvents include, for example, aromatic compounds (e.g., xylene, toluene, and alkylnaphthalenes), chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons (e.g., chlorobenzene, chloroethylene, and methylene chloride), aliphatic hydrocarbons (e.g., cyclohexane), paraffins (e.g., petroleum fractions, mineral, and vegetable oils), alcohols (e.g., butanol or glycols and their ethers and esters), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone), and strongly polar solvents (e.g., dimethylformamide and dimethyl sulfoxide). Other examples of organic solvents include, but are not limited to, xylene, propylbenzene fraction, or mixed naphthalene fraction, mineral oil, substituted aromatic organic liquids such as dioctyl phthalate; kerosene, dialkylamides of various fatty acids, in particular dimethylamides of fatty glycols and glycol derivatives such as n-butyl ether, ethyl ether or methyl ether of diethylene glycol, methyl ether of triethylene glycol, petroleum fraction or mineral oil, aromatic solvents, hydrocarbons such as paraffin oil, terpene solvents, rosin derivatives, aliphatic ketones such as cyclohexanone, complex aliphatic and aromatic alcohols such as 2-ethoxyethanol, esters of the above-mentioned vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, and tung oil. A mixture of two or more organic liquids may be used in the preparation of certain emulsifying concentrates. Examples of organic liquids include xylene and propylbenzene fractions, with xylene being most preferred in some cases. The surface-active dispersant is typically used in liquid formulations in amounts of 0.1 to 20 weight percent based on the combined weight of the dispersant with one or more of the compounds.

[0121] In some embodiments, the pesticide comprises a solid carrier, which may include, for example, ammonium salts and pulverized natural minerals (e.g., kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth), pulverized synthetic minerals (e.g., highly dispersed silica, alumina, and silicates), pulverized and fractionated natural rocks (e.g., calcite, marble, pumice, sepiolite, and dolomite), synthetic granules of inorganic and organic meals, and granules of organic materials (e.g., sawdust, coconut husk, corn cob, and tobacco stalk). In some embodiments, the dry composition may include powders, etc.

[0122] In some embodiments, the pesticide comprises emulsifiers and foaming agents, such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers, such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, and aryl sulfonates) and protein hydrolysates.

[0123] In some embodiments, the pesticide comprises a dispersant, such as lignin-sulfite wastewater and methylcellulose. In some embodiments, the pesticide comprises a tackifier such as carboxymethylcellulose, and natural and synthetic polymers in the form of powders, granules, or lattice materials such as gum arabic, polyvinyl alcohol, and polyvinyl acetate, as well as natural and synthetic phospholipids such as cephalin and lecithin. In some embodiments, the pesticide comprises a nonionic emulsifier, which may include polyalkylene glycol ethers, and condensation products of alkylphenols and arylphenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as ethoxylated alkylphenols, and carboxylic acid esters solubilized with polyols or polyoxyalkylenes. In some embodiments, the pesticide comprises a cationic emulsifier comprising quaternary ammonium compounds and aliphatic amine salts. In some embodiments, the pesticide comprises an anionic emulsifier, which includes an oil-soluble salt of alkylarylsulfonic acid (e.g., calcium), an oil-soluble salt of sulfated polyglycol ether, or a phosphorylated polyglycol ether and a suitable salt.

[0124] In some embodiments, the pesticide includes a surfactant such as a nonionic surfactant, such as a sulfonated lignin, condensed naphthalene sulfonate, naphthalene sulfonate, alkylbene sulfonate, alkyl sulfonate, or an ethylene oxide adduct of alkylphenol or a mixture thereof.

[0125] In some embodiments, the pesticide may include inorganic pigments, such as colorants like iron oxide, titanium dioxide, and Prussian blue; organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes; and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc.

[0126] In certain embodiments, a pesticide is defined as any substance or formulation intended for application to plants, 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; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0127] Ascaloside - Antifungal Blend In certain embodiments, the Disclosure provides compositions comprising a mixture of ascaloside and other pesticides. Such compositions are useful by enabling the simple simultaneous application of ascaloside(s) and pesticide(s) to crops, thereby mitigating the phytotoxic effects of one or more of the pesticide components in the mixture. Certain non-limiting combinations of ascaloside and certain types of pesticides used in various embodiments of the Disclosure are described in more detail below.

[0128] In certain embodiments, such compositions are characterized in that the phytotoxic effects of the combined composition are less than those of the composition lacking ascalosides.

[0129] Ascaloside + triazole antifungal agent Triazole fungicides are known to have phytotoxic effects on many crops. In some embodiments, this disclosure provides compositions and methods relating to one or more ascalosides and one or more triazole fungicides (e.g., prothioconazole, tebuconazole, or fungicides having the same mode of action as prothioconazole or tebuconazole). In some embodiments, ascalosides can be used with any triazole fungicide or any fungicide that inhibits the CYP51A1 enzyme. The CYP51A1 enzyme is required for the biosynthesis of ergosterol, an important component of fungal cell membranes. The use of at least one ascaloside and a fungicide enhances the activity of the fungicide, requiring a smaller amount of fungicide.

[0130] Triazole fungicides include, but are not limited to, mycrobutanil, epoxyconazole, ipconazole, metconazole, uniconazole-P, uniconazole, triticonazole, tricyclazole, triazbutyl, triadimenol, triadimephone, tetraconazole, tebuconazole, simeconazole, quinconazole, prothioconazole, propiconazole, penconazole, imibenconazole, hexaconazole, fluconazole, fluconazole-cis, flutriafor, flusilazole, fluquinconazole, flutrimazole, fenbuconazole, etaconazole, diniconazole-M, diniconazole, difenoconazole, diclobutrazol, cyproconazole, bromconazole, vitertanol, azaconazole, and amisulbrom. In certain embodiments, the triazole fungicide is prothioconazole or tebuconazole. The scope also includes mixtures of fungicides, particularly prothioconazole, tebuconazole, or fungicides used in combination with other triazoles. Such fungicides used with prothioconazole include, but are not limited to, azoxystrobin, boscalid, tebuconazole, trifloxystrobin, fluopyram, azoxystrobin, and benzovindiflupyr. Such fungicides used with tebuconazole include, but are not limited to, azoxystrobin, boscalid, prothioconazole, trifloxystrobin, fluopyram, azoxystrobin, and benzovindiflupyr.

[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 manufactured primarily for its fungicidal properties. Prothioconazole is a systematic broad-spectrum mycicide belonging to the triazoline thioine chemical class. It is a member of the triazole compound class and possesses a unique toxin family among mycicides of this class. Its effective fungicidal properties may be attributed to its ability to inhibit CYP51A1, an enzyme required for the biosynthesis of ergosterol, a key component of fungal cell membranes. Prothioconazole is a mycicide manufactured for the control of diseases caused by ascomycetes, basidiomycetes, and imperfect fungi. Prothioconazole is generally applied alone or as a tank mixture with other agents such as mycicides, insecticides, herbicides, or other crop agents. Any source of prothioconazole can be used, but it is sold under various brand names including Co-Op Pivot, Nufarm Propiconazole, Princeton, Fitness, Pivot 418EC, Quilt, Topnotch, Trivapro, Proline, Cotegra, Prosaro 250EC, Prosaro XTR, Delaro 325SC, Propulse, and Timor 240EC.

[0132] Prothioconazole is typically formulated as a 4 lb / gal suspension concentrate (equivalent to a fluid concentrate; FLC) formulation (Proline® 480 SC fungicide, 41% active ingredient). This product can be applied as a foliar spray or soil spray (soil spray in the case of peanuts) after germination using ground or aerial equipment at a rate of 0.088–0.178 lb ai / A / application (0.100–0.200 kg ai / ha / application). The proposed maximum seasonality ranges from 0.285–0.713 lb ai / A (0.320–0.800 kg ai / ha), and the proposed retreatment interval is 5–21 days. The use of prothioconazole with at least one ascaloside according to this disclosure reduces the plant toxicity of the fungicide.

[0133] Tebuconazole (IUPAC: 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazole-1-ylmethyl)pentan-3-ol) is a systemic mycicide that provides both curative and preventive control of diseased plants. Tebuconazole is used in many different common mycicide products to control fungi, bacteria, and viruses that affect plants. Tebuconazole is a mycicide known as a DMI (demethylation inhibitory mycicide) that affects the cell wall of fungi by inhibiting spore germination and fungal growth. It also interferes with the production of ergosterol, a molecule essential for fungal formation. As a result, fungal formation is slowed down and eventually stopped. Due to this unique mode of action, tebuconazole is more bacteriostatic or growth inhibitory than fungicidal or fungicidal. Tebuconazole is a versatile mycicide that can be used for both curative and preventive fungal control. It works systemically, being absorbed by the target plant to protect it from disease, prevent further spread, or completely eliminate the disease depending on the severity level. Some of the common fungal and disease problems that tebuconazole is known to treat include rust, large white mold, leaf spot, and anthracnose. Tebuconazole is also used on turfgrass and ornamental plants to control a variety of fungal diseases, including, but not limited to, leaf blight, gray spot, and powdery mildew.

[0134] Tebuconazole may be applied at a rate of 4–10 fl. oz. per acre. The spray volume may range from approximately 5–300 gallons per acre to a completed spray, depending on the equipment used, plant species, and plant growth stage. However, tebuconazole can cause phytotoxicity. Some plants are sensitive to the triazole active ingredient. The use of tebuconazole in combination with ascaloside(s) provided pursuant to this disclosure can reduce or prevent this phytotoxicity.

[0135] In certain embodiments, the Disclosure provides a blend of a triazole fungicide and ascaloside, wherein the weight ratio of the triazole fungicide to ascaloside is greater than 1000:1. In certain embodiments, the Disclosure provides a blend of a triazole fungicide and ascaloside, wherein the weight ratio of the triazole fungicide to ascaloside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0136] In certain embodiments, the disclosure provides a blend of a triazole fungicide and askaloside, characterized in that the blend product has a lower level of phytotoxicity effect on the crop to which the blend product is applied compared to the application of the triazole fungicide alone. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking askaloside. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent composition lacking askaloside. In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent composition lacking askaloside. In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0137] In certain embodiments, the Disclosure provides a blend of tebuconazole and ascaloside, wherein the weight ratio of tebuconazole to ascaloside is greater than 1000:1. In certain embodiments, the Disclosure provides a blend of tebuconazole and ascaloside, wherein the weight ratio of tebuconazole to ascaloside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0138] In certain embodiments, the disclosure provides a blend of tebuconazole and askaloside, characterized in that the blend product has a lower level of phytotoxicity effect on the crop to which the blend product is applied compared to the application of a tebuconazole formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking askaloside. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent tebuconazole composition lacking askaloside. In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent tebuconazole composition lacking askaloside. In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0139] In certain embodiments, the Disclosure provides a blend of prothioconazole and ascaloside, wherein the weight ratio of prothioconazole to ascaloside is greater than 1000:1. In certain embodiments, the Disclosure provides a blend of prothioconazole and ascaloside, wherein the weight ratio of prothioconazole to ascaloside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0140] In certain embodiments, the disclosure provides a blend of prothioconazole and askaloside, characterized in that the blend product has a lower level of phytotoxicity effect on the crop to which the blend product is applied compared to the application of a prothioconazole formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking askaloside. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent prothioconazole composition lacking askaloside. In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent prothioconazole composition lacking askaloside. In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0141] In certain embodiments, the Disclosure provides a blend of propiconazole and ascaloside, wherein the weight ratio of propiconazole to ascaloside is greater than 1000:1. In certain embodiments, the Disclosure provides a blend of propiconazole and ascaloside, wherein the weight ratio of propiconazole to ascaloside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0142] In certain embodiments, the disclosure provides a blend of propiconazole and askaloside, characterized in that the blend product has a lower level of phytotoxicity effect on the crop to which the blend product is applied compared to the application of a propiconazole formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking askaloside(s). In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent propiconazole composition lacking askaloside(s). In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent propiconazole composition lacking askaloside(s). In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0143] Ascaloside + Strobilurin fungicide While strobilurin fungicides are highly beneficial for disease control, some are known to cause phytotoxicity under certain circumstances. These are indicated on the product label. For example, apple varieties with a genetic background including MacIntosh are highly susceptible to azoxystrobin. Another example: trifloxystrobin can damage Concord grapes, while kresoxim-methyl is phytotoxic to certain sweet cherry varieties. Growers should be aware of phytotoxicity concerns both to the treated crop and the potential for damage due to spray drift.

[0144] Another aspect of the risk of plant toxicity is that tank mixing of strobilurin fungicides with epidermal oils, surfactants, or materials that solubilize certain liquid formulations of insecticides can increase the potential for their plant toxicity. While some of the active ingredients may be found within the host tissue, a large portion of the dose of strobilurin fungicide remains on or within the plant cuticle. The application of spray materials that allow unusually high levels of these fungicides to penetrate the host tissue can cause plant toxicity in certain crops or varieties where nothing is normally expected. Blends provided containing strobilurin(s) and one or more ascalosides can reduce the effects of these plant toxicity and provide a very convenient means of achieving this improved safety.

[0145] In some embodiments, the disclosure provides compositions and methods relating to blends containing ascaloside and strobilurin (e.g., azoxystrobin, kresoxime-methyl, picoxystrobin, pyraclostrobin, trifloxystrobin, famoxadone, or phenamidone). In some embodiments, ascaloside can be used with any strobilurin fungicide or any fungicide that inhibits mitochondrial respiration, more specifically, any fungicide that binds to the quinol binding site of a cytochrome complex (e.g., an external quinone inhibitor or QoI). In certain embodiments, ascaloside can be used with any strobilurin fungicide (e.g., any material called a strobilurin fungicide, including members of the class of natural products collectively known as strobilurins, or synthetic analogs, derivatives, or mimics of strobilurin natural products, or compositions including synthetic molecules having a similar structure or mode of action to strobilurins, including phenamidone and famoxadone). When used with ascaloside, the fungicide has less phytotoxicity to crops, giving growers greater flexibility in the rate and / or frequency of application, thereby enabling more effective control of pathogens.

[0146] According to this disclosure, ascaloside can be used in combination with QoI fungicides, particularly strobilurin, to achieve Q o I. It can reduce the plant toxicity of fungicides or their formulations. Q o I. Fungicides include, but are not limited to, strobilurin, azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, phenamistrobin, dimoxystrobin, fluoxastrobin, methaminostrobin, mandestrobin, pyrametostrobin, pyrazoxystrobin, kresoxime-methyl, phenamidone, and famoxadone.

[0147] As described above, strobilurin or fungicides having the same mode of action as strobilurin can be used in the implementation of the present invention. In particular, mixtures of fungicides used in combination with strobilurin are also included. Such antifungal agents used with strobilurin include boscalid, tebuconazole, propiconazole, mycrobutanil, epoxyconazole, ipconazole, metconazole, uniconazole-P, uniconazole, triticonazole, tricyclazole, triazbutyl, triadimenol, triadimephone, tetraconazole, tebuconazole, simeconazole, quinconazole, prothioconazole, propiconazole, penconazole, imibenconazole, hexaconazole, fluconazole, fluconazole-cis, flutriafor, flusilazole, fluquinconazole, flutrimazole, fenbuconazole, etaconazole, diniconazole-M, diniconazole, difenoconazole, diclobutrazol, cyproconazole, bromconazole, vitertanol, azaconazole, and amisulbrom Examples include fluopyram and benzovindiflupirin, but are not limited to these.

[0148] Azoxystrobin (IUPAC: methyl(E)-2-[2-[6-(2-cyanophenoxy)pyrimidine-4-yl]oxyphenyl]-3-methoxypropa-2-enoate) is a synthetic chemical primarily manufactured for its fungicidal properties. Azoxystrobin is a xylem-mobil systemic mycicide with penetrating, protective, and curative properties. It is a member of the strobilurin class of compounds. Azoxystrobin is effective against numerous fungal plant pathogens, including members of the Ascomycota, Imperfect Fungi, and Basidiomycota, as well as the Oomycota. Additionally, its properties mean it can move inostomally within plant tissue to protect parts of the crop that are not in contact with the spray. Important diseases it controls include leaf spot, rust, powdery mildew, downy mildew, nettle spot, and wilt. Globally, azoxystrobin is registered for use on all important crops. For example, in the European Union and the United States, its use is registered for wheat, barley, oats, rye, soybeans, cotton, rice, strawberries, peas, beans, onions, and many other vegetables. Azoxystrobin can be applied alone or as a tank mixture with other agents such as fungicides, insecticides, herbicides, or other crop agents. Any source of azoxystrobin can be used, but it is sold under various trade names 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 suspension concentrate formulation of 2 lb / gal. Application is carried out using ground or aerial equipment at a rate of 0.1–0.25 lb ai / A / application (0.100–0.200 kg ai / ha / application). The proposed maximum seasonality is in the range of 1.5 lb ai / A, and the proposed retreatment interval is 14–21 days. The use of azoxystrobin with at least one ascaloside of the present invention reduces the phytotoxicity of the fungicide formulation, making it more practical for growers to reduce disease severity without causing phytotoxicity-related damage or stress to plants.

[0150] Picoxystrobin (IUPAC: (E)-methyl 3-methoxy-2-(2-(((6-(trifluoromethyl)pyridine-2-yl)oxy)methyl)phenyl)acrylate) is a systemic mycicide that provides both curative and preventive control of diseased plants. Picoxystrobin is a synthetic chemical manufactured primarily for its fungicidal properties. Picoxystrobin is a xylem-mobil systemic mycicide with penetrating, protective, and curative properties. It is a member of the class of compounds strobilurin. Picoxystrobin is effective against numerous fungal plant pathogens, including members of the Ascomycota, Imperfect Fungi, and Basidiomycota, as well as Oomycota. Additionally, its properties mean that it can move inospherically within plant tissue to protect parts of the crop that are not in contact with the spray. Key diseases it controls include leaf spot, rust, powdery mildew, downy mildew, nettle spot, and wilt. 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, Netherlands, New Zealand, Norway, Poland, Romania, Slovakia, South Africa, Sweden, the United States, and the United Kingdom.

[0151] Picoxystrobin is sold as a single-component fungicide and in several mixtures with other fungicides, including cyproconazole (Furlong, Stinger, and Approach Prima), chlorothalonil (Credo and Plinker), and cyprodinil (Acanto Prima). Picoxystrobin can be applied alone or as a tank mixture with other agents such as fungicides, insecticides, herbicides, or other crop agents. Any source of picoxystrobin can be used, but it is sold under various brand names, including Approach, 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 a rate of 0.05–0.2 lb AI per acre. Spray volumes can range from approximately 5–300 gallons per acre of finished spray, depending on the equipment used, plant species, and plant growth stage. Using picoxystrobin with at least one ascaloside of the present invention in various ways, as outlined herein, reduces the phytotoxicity of the fungicide formulation, making it more practical for growers to reduce disease severity without causing phytotoxicity-related damage or stress to plants.

[0153] In certain embodiments, the Disclosure provides a blend of a strobilurin fungicide and ascaloside, wherein the weight ratio of the strobilurin fungicide to the ascaloside is greater than 1000:1. In certain embodiments, the Disclosure provides a blend of a strobilurin fungicide and ascaloside, wherein the weight ratio of the strobilurin fungicide to the ascaloside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0154] In certain embodiments, the disclosure provides a blend of a strobilurin fungicide and askaloside, characterized in that the blend product has a lower level of phytotoxicity effect on the crop to which the blend product is applied compared to the application of a strobilurin fungicide formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking askaloside. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent composition lacking askaloside. In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent composition lacking askaloside. In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0155] In certain embodiments, the Disclosure provides a blend of azoxystrobin and ascaloside, wherein the weight ratio of azoxystrobin to ascaloside is greater than 1000:1. In certain embodiments, the Disclosure provides a blend of azoxystrobin and ascaloside, wherein the weight ratio of azoxystrobin to ascaloside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0156] In certain embodiments, the disclosure provides a blend of azoxystrobin and askaloside, characterized in that the blend product has a lower level of phytotoxicity effect on the crop to which the blend product is applied compared to the application of an azoxystrobin formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking askaloside(s). In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent azoxystrobin composition lacking askaloside(s). In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent azoxystrobin composition lacking askaloside(s). In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0157] In certain embodiments, the Disclosure provides a blend of azoxystrobin and ascaloside, wherein the weight ratio of azoxystrobin to ascaloside is greater than 1000:1. In certain embodiments, the Disclosure provides a blend of azoxystrobin and ascaloside, wherein the weight ratio of azoxystrobin to ascaloside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, or greater than 10,000:1.

[0158] In certain embodiments, the disclosure provides a blend of picoxystrobin and ascaloside, characterized in that the blend product has a lower level of phytotoxicity effect on the crop to which the blend product is applied compared to the application of a picoxystrobin formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking ascaloside(s). In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent picoxystrobin composition lacking ascaloside(s). In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent picoxystrobin composition lacking ascaloside(s). In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0159] Ascaloside + SDHI fungicide In some embodiments, this disclosure provides compositions and methods relating to ascaloside and succinate dehydrogenase inhibitor (SDHI) mycicides. Succinate dehydrogenase (SDH) complex II is considered an essential component of the mitochondrial respiratory chain in fungi. The SDH enzyme directly transfers electrons derived from succinate to the ubiquinone pool of the respiratory chain, thereby facilitating energy transfer within mitochondria. Succinate dehydrogenase inhibitors (SDHIs) are a class of mycicides that act on mitochondrial SDH complex II to block cellular energy transfer and thereby inhibit fungal development. Many SDHIs inhibit fungal respiration by blocking the ubiquinone-binding (Qp) site. SDHIs that strongly bind to the Qp site physically block access to the ubiquinone substrate, thereby preventing further circulation of succinate oxidation.

[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, flumetobel, fluopicolide, fluopimomide, thioximide, triclamide, zarilamide, 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, oxathiine fungicides, furacarboxamide fungicides, pyrazinecarboxamide fungicides, pyrazolecarboxamide fungicides, and pyridinecarboxamide fungicides. Examples of oxathiine fungicides include, but are not limited to, carboxyne and oxycarboxyne. Examples of furacarboxamide fungicides include, but are not limited to, fenflam, flucarbanil, or metofloxam. An example of a pyrazinecarboxamide fungicide is pyraziflumid. Examples of pyrazole carboxamide fungicides include, but are not limited to, benzovindiflupir, bixafen, fluveneteram, fluindapir, fluxapyroxad, flumetopyr, impilfluxam, isoflucipram, isopyrazam, penflufen, penthiopyrad, pidflumetofen, pyrapropoine, sedaxane, etaboxam, and tifluzamide. Examples of pyridine carboxamide fungicides include, but are not limited to, boscalid or cyclobutrifluram. Examples of SDHI fungicides include thiophenamide fungicides that inhibit SDH complex II, such as isofetamide.

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

[0162] In certain embodiments, the disclosure provides a blend of an SDHI fungicide and askaloside, characterized in that the blend product has a lower level of phytotoxicity effect on the crop to which the blend product is applied compared to the application of the SDHI fungicide formulation alone. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking askaloside. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent composition lacking askaloside. In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent composition lacking askaloside. In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0163] Multi-way fungicide blend In efforts to overcome the increasing resistance of pathogens to fungicides, growers are increasingly relying on fungicide products that often contain blends of multiple fungicidal components with different modes of action. Such products typically contain the total dose of each fungicide component (for example, if applied in the proportions indicated on the label, such a blend provides an amount of each active substance similar to the amount applied if that active substance were used as a single product in the proportions indicated on the label). This obviously leads to an overall increase in the amount of fungicide applied per acre, and consequently an increased risk of phytotoxic effects on crops. Unfortunately, such multi-way products are harsher on plants, either due to the additional or synergistic phytotoxic effects of the active ingredients, or as a result of the more complex formulations required to compatibilize multiple pesticides, or due to the larger volumes of adjuvants and inactive formulation components applied to crops in these multi-way products. These high levels of phytotoxicity may undermine the benefits gained from controlling fungicide-resistant pathogens and may reduce product awareness in the market.

[0164] In certain embodiments, the disclosure addresses these issues by providing ascaloside blends with multiway fungicide products and / or ascaloside products intended for simultaneous application to crops with fungicides containing at least two activators. In certain embodiments, such products comprise a blend of ascaloside(s) and two or more chemifungicides. In certain embodiments, the two or more chemifungicides are from the same chemical class (e.g., two different triazoles or two different strobilurins). More generally, the two or more chemifungicides are from different chemical classes (e.g., triazole and strobilurin, triazole and SDHI, or triazole, strobilurin, and SDHI).

[0165] In certain embodiments, the Disclosure provides blends and / or products intended for simultaneous application to crops containing one or more ascalosides and two or more different triazole fungicides (e.g., the fully described triazole fungicides above). In certain embodiments, the Disclosure provides blends and / or products intended for simultaneous application to crops containing one or more ascalosides and two or more different strobilurin fungicides (e.g., the fully described strobilurin fungicides above). In certain embodiments, the Disclosure provides blends and / or products intended for simultaneous application to crops containing one or more ascalosides and two or more different SDHI fungicides (e.g., the more fully described SDHI fungicides above). In certain embodiments, the Disclosure provides blends and / or products intended for simultaneous application to crops containing one or more ascalosides, at least one triazole fungicide, and at least one strobilurin fungicide. In certain embodiments, the Disclosure provides blends and / or products intended for simultaneous application to crops, containing one or more ascalosides, at least one triazole fungicide, and at least one SDHI fungicide. In certain embodiments, the Disclosure provides blends and / or products intended for simultaneous application to crops, containing one or more ascalosides, at least one strobilurin fungicide, and at least one SDHI fungicide. In certain embodiments, the Disclosure provides blends and / or products intended for simultaneous application to crops, containing one or more ascalosides, at least one triazole fungicide, at least one strobilurin fungicide, and at least one SDHI fungicide.

[0166] In certain embodiments, the Disclosure provides blends and / or products intended for simultaneous application to crops containing one or more ascalosides, characterized in that at least two different chemifungicides have a weight ratio of chemifungicide to ascaloside(s) greater than 1000:1. In certain embodiments, the Disclosure provides blends and / or products intended for simultaneous application to crops, containing one or more ascalosides and at least two different chemifungicides, wherein the weight ratio of chemifungicide to ascaloside(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 a blend of ascaloside and two or more fungicides, characterized in that the blend product has a lower level of phytotoxicity effect on the crop to which the blend product is applied compared to the application of two or more fungicide formulations individually. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking ascaloside. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent composition lacking ascaloside. In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent composition lacking ascaloside. In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

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

[0169] The organic phosphates present in the blends provided include acephate, azamethiphos, azinophosethyl, azinophosmethyl, bromophos, bromophosethyl, kazusaphos, chlorethoxyphos, chlorpyrifos, chlorfenbinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methylsulfone, diariphos, diazinon, dichlorvos, diclotophos, dimethoate, disulfoton, ethione, etoprophos, etrimphos, femfur, phenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazophos, honofos, formothion, fothiazate, heptenophos, isazofos, isothioate, and isoxathio. This may include malathion, methacryphos, methamidophos, methidathion, methylparathion, mevinphos, monoclotophos, nared, omethoate, oxydemetonmethyl, paraoxone, parathion, parathionmethyl, fenthoate, phosalon, phosphoran, phosphocarb, phosmet, phosphamidone, pholate, foxim, pirimiphos, pirimiphosmethyl, profenophos, propaphos, proetamphos, prothiophos, pyraclophos, pyridapention, quinalphos, sulprophos, temephos, terbuphos, tebupyrimphos, tetrachlorvinphos, thymetone, triazophos, trichlorfon, and bamidothion.

[0170] Carbamates present in the offered blend may include alanicarb, aldicarb, 2-sec-butylphenylmethylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, chloetocarb, ethiofencarb, phenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pyrimicarb, propoxul, thiodicarb, thiophanox, triazamate, and UC-51717.

[0171] The pyrethroids present in the blend provided include acrinatin, allethrin, alphamethrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, α-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), biorethmetrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, and cy This may include cytrine, cyphenothrine, deltamethrine, empenthrine, esfenvalerate, etofenprox, fenfluthrine, fenpropathrine, fenvalerate, flucitrinate, flumethrine, fluvalinate (D isomer), imiprothrine, cyhalothrine, lambda-cyhalothrine, permethrine, phenothrine, prallethrine, pyrethrine (natural product), resmethrine, tetramethrine, transfluthrine, theta-cypermethrine, silafluofen, t-fluvalinate, tefluthrine, tralomethrine, and zeta-cypermethrine.

[0172] Arthropod growth regulators present in the blends provided may include: a) benzoylureas: chitin synthesis inhibitors such as chlorfluazurone, diflubenzuron, fluazurone, flucycloxurone, flufenoxurone, hexaflumurone, lufenuron, novaron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, and chlorfentadine; b) ecdysone antagonists such as halofenozide, methoxyfenozide, and tebufenozide; c) juvenile hormone-like substances such as pyriproxyfen, siethoprene (including S-methoprene), and phenoxycarb; and d) lipid biosynthesis inhibitors such as spirodiclofen.

[0173] In certain embodiments, the Disclosure provides a blend of one or more insecticides and ascalosides, wherein the weight ratio of insecticide(s) to ascaloside is greater than 100:1, greater than 500:1, or greater than 1000:1. In certain embodiments, the Disclosure provides a blend of SDHI fungicides and ascalosides, wherein the weight ratio of insecticides to ascalosides 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 a blend of one or more insecticides and ascalosides, characterized in that the blended product has a lower level of phytotoxicity effect on the crop to which the blended product is applied compared to the application of one or more insecticides individually. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking ascalosides. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent composition lacking ascalosides. In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent composition lacking ascalosides. In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0175] In efforts to overcome the increasing resistance of pests to insecticides, growers are increasingly relying on products containing blends of multiple insecticidal components with different modes of action. Such products typically contain the total dose of each insecticide component (for example, if applied in the proportions indicated on the label, such a blend provides an amount of each active substance similar to the amount applied if its active substance were used as a single product in the proportions indicated on the label). This obviously leads to an overall increase in the amount of insecticide applied per acre, and consequently an increased risk of phytotoxic effects on crops. Unfortunately, such multi-way products are harsher on plants, either due to the additive or synergistic phytotoxic effects of the active ingredients, or as a result of the more complex formulations required to compatibilize the multiple insecticides, or due to the larger volumes of adjuvants and inactive formulation components applied to crops in these multi-way products. These high levels of phytotoxicity may undermine the benefits gained from controlling insecticide-resistant pests and may reduce product awareness in the market.

[0176] In certain embodiments, the Disclosure addresses these issues by providing ascaloside blends with multi-way insecticide products and / or ascaloside products intended for simultaneous application to crops with insecticides containing at least two activators. In certain embodiments, such products comprise a blend of ascaloside(s) and 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 generally, the two or more insecticides are from different chemical classes (e.g., two-way blends including carbamates and organochlorines, nicotinoids and phosphoramide thioates, carbamates and organophosphates, nicotinoids and pyrethroids, or any combination thereof).

[0177] Ascaloside + herbicide In some embodiments, the Disclosure provides compositions and methods relating to the use of ascaloside and one or more herbicides. In some embodiments, the Disclosure provides compositions and methods relating to ascaloside and one or more herbicides, wherein the ascaloside(s) serve as safety agents to reduce the phytotoxic effects of the herbicide on the treated crop.

[0178] Herbicides that can reduce phytotoxic side effects on crop plants using ascaloside include, for example, carbamates, thiocarbamates, haloacetanilide, quinolyloxy, quinoxalyloxy, pyridyloxy, benzoxazolyloxy, and benzothiazolyloxyphenoxyalkane carboxylic acid esters, substituted phenoxy, naphthoxy, and phenoxyphenoxycarboxylic acid derivatives, cyclohexanedione derivatives, imidazolinone, pyrimidinyloxypyridinecarboxylic acid derivatives, pyrimidyloxybenzoic acid derivatives, sulfonylurea, triazolopyrimidinesulfonamide derivatives, and S-(N-aryl-N-alkylcarbamoylmethyl)dithiophosphate esters, hormone-type herbicides, pyridinecarboxylic acid, triazinonone, triazolinone, pyridinecarboxamide, hydroxybenzonitrile, and isoxazole. Phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts, sulfonylurea, imidazolinone, isoxazole, and herbicides used to expand the activity spectrum together with ALS inhibitors (acetolactate synthase inhibitors) are preferred, such as bentazone, cyanazine, atrazine, bromoxynil, dicamba, and other foliar herbicides.

[0179] Herbicides of Group B are known, for example, from the publications mentioned above, as well as from “The Pesticide Manual”, The British Crop Protection Council and the Royal Soc. of Chemistry, 12th Edition, 2000, “Agricultural Chemicals Book II - Herbicides-”, by WT Thompson, Thompson Publications, Fresno Calif., USA 1990, and “Farm Chemicals Handbook '90”, Meister Publishing Company, Willoughby Ohio, USA, 1990, each of which is incorporated by reference. Other compounds for use in the present invention, such as the non-commercial herbicide benzoyl isoxazole and / or dione compounds, may be prepared by the methods described in the 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, a generic name is listed in the herbicide list. In such cases, the generic name identifies the active ingredient in commercial forms or multiple forms, including derivatives such as salts and esters, even if a specific salt or ester is not specifically mentioned, preferably in its usual commercial form.

[0181] Herbicide application can be before or after emergence. The preferred application method depends on the usual or optimal application time for the specific herbicide or combination of herbicides.

[0182] In certain embodiments, the Disclosure provides a blend of one or more herbicides and ascalosides, wherein the weight ratio of herbicides to ascalosides is greater than 100:1, greater than 500:1, or greater than 1000:1. In certain embodiments, the Disclosure provides a blend of herbicides and ascalosides, wherein the weight ratio of herbicides to ascalosides 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 a blend of one or more herbicides and ascalosides, characterized in that the blended product has a lower level of phytotoxicity effect on the crop to which the blended product is applied compared to the application of one or more herbicides individually. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking ascalosides. In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent composition lacking ascalosides. In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent composition lacking ascalosides.

[0184] In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0185] Ascaloside blend with adjuvant As described above, in certain embodiments, ascaloside can be used to reduce or prevent the phytotoxic effects caused by chemicals used in conjunction with pesticides that are not the active ingredient. Such materials include adjuvants, solvents, and additives present in the formulated pesticide product, as well as materials intended to be mixed with or applied concurrently with the active ingredient of the pesticide (e.g., surfactants, wetting agents, defoamers, etc., which can be tank-mixed with the pesticide before application to crops). In some examples, such materials are known to have phytotoxic effects on plants, and the application of ascaloside can reduce or prevent such phytotoxicity.

[0186] In other embodiments, the disclosure provides useful means for introducing ascaloside to prevent the phytotoxic effects of active pesticide formulations that may be combined with ascaloside. Accordingly, the disclosure provides novel multifunctional additives containing one or more conventional additives along with one or more ascalosides that exist as “safety agents” to reduce the cytotoxicity of pesticide products to be combined with before application. Examples of such compositions include blends of surfactants and ascalosides, blends of wetting agents with ascalosides, blends of defoamers and ascalosides, blends of surfactants and ascalosides, and blends of crop oils and ascalosides. Each of the listed ascaloside additive blends may be intended for tank mixing with other pesticides.

[0187] In certain embodiments, such ascaloside additive blends are characterized in that the use of the blended product during pesticide application results in a lower level of phytotoxicity to the crop to which the blend is applied, compared to the application of the pesticide with the same additive(s) lacking ascaloside. In certain embodiments, the blend is characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking ascaloside(s). In certain embodiments, the method provided is characterized in that one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent composition lacking ascaloside(s). In certain embodiments, the blend provided is characterized in that one or more phytotoxic symptoms are substantially absent compared to the use of an equivalent additive composition lacking ascaloside(s). In certain embodiments, such plant toxicity effects are selected from the group consisting of poor germination; seedling death; death or damage to rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

[0188] composition As described above, the disclosed treatments using ascaloside in combination with antimicrobial agents (including, but not limited to, triazoles, strobilurin, or SDHI fungicides, as detailed above), insecticides (including, but not limited to, carbamates, organochlorines, nicotinoids, phosphoramidothioates, organophosphates, and pyrethroids), or additives such as adjuvants, solvents, surfactants, defoamers, or wetting agents, or other components of the pesticide composition, can be used to reduce the phytotoxic effects of those pesticides.

[0189] In some embodiments, the treatment with ascaloside and pesticides provided herein can favorably shift the balance between the desired beneficial effect and the phytotoxic effects on the crop by ascaloside, thereby enabling the application of higher proportions or more frequent applications of the pesticide.

[0190] One or more ascalosides and one or more pesticides are generally applied in an effective dose. An effective dose is an amount sufficient to control, treat, prevent, or inhibit a plant pathogen and / or reduce the severity of a plant disease or reduce the incidence of a plant disease, or, in the case of ascalosides, an amount that reduces or prevents the phytotoxic effects of one or more pesticides. By controlling plant diseases, an effective dose improves the desired agrochemical trait and promotes and increases plant health, growth, and yield. One or more ascalosides and one or more pesticides can be applied to plants in a variety of ways. In some embodiments, one or more ascalosides and one or more pesticides are applied simultaneously either in separate formulations / agricultural compositions (e.g., so that both one or more ascalosides and one or more pesticides are applied to each other within a given period of time) or in the same formulation / agricultural composition.

[0191] Simultaneous application, in some embodiments, may include applying two separate formulations (one containing one or more ascalosides and the other containing one or more pesticides) at close intervals, for example, substantially simultaneously or within about 1 minute, 5 minutes, 10 minutes, 30 minutes, 1 hour, 4 hours, 6 hours, 12 hours, 24 hours, or 2 days) from each other. When one or more ascalosides and one or more pesticides are applied separately, the one or more ascalosides may be applied before or after the application of additional pesticides.

[0192] Simultaneous application, in some embodiments, may include combining one or more ascalosides with one or more pesticides shortly before application to plants (e.g., immediately before application). One preferred method for administering one or more ascalosides and one or more pesticides is to mix the components in situ, for example, by adding one or more ascalosides to a tank mixture containing one or more pesticides.

[0193] In other embodiments, the components to be applied simultaneously may be combined at an even earlier point in time. In such embodiments, an agricultural formulation is prepared, the formulation comprising one or more ascalosides and one or more pesticides in combination with one or more inert components. Advantageously, in some embodiments, the combinations of one or more ascalosides and one or more pesticides provided herein are compatible with each other, and the resulting formulation can exhibit stability over long periods (e.g., more than one week, more than one month, more than two months, more than three months, more than four months, more than five months, or more than six months) under standard conditions (e.g., room temperature, housed in one or more closed systems of relative humidity zones). Demonstration of stability in this context may vary. For example, in some embodiments, no significant separation is observed with the naked eye. In some embodiments, no significant change in the amount of the active ingredient and / or ascaloside is observed via conventional methods (e.g., spectroscopy). In some embodiments, no significant chemical degradation of the active ingredient and / or ascaloside is observed using conventional methods (e.g., spectroscopy).

[0194] Such formulations containing both one or more ascalosides and one or more pesticides may vary in composition and form. In some embodiments, such formulations are in solid form, and in some embodiments, such formulations are in liquid form. As referenced, in addition to one or more ascalosides and one or more pesticides, one or more inactive components, such as one or more agriculturally acceptable carriers (also referred to as agriculturally acceptable or suitable adjuvants), are generally included in the formulation. In the formulations and methods of this disclosure, it is preferable to use non-toxic carriers. The term "agriculturally acceptable carrier" includes any carrier suitable for administration to plants or soil, including conventional excipients in formulation technology, such as solutions (e.g., directly sprayable or dilutable solutions), emulsions (e.g., emulsion concentrates and diluted emulsions), wettable powders, suspensions, soluble powders, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, encapsulation in polymer materials, coatable pastes, natural and synthetic materials impregnated with active compounds, and those used to form microencapsulations in polymer materials. In some embodiments, agriculturally acceptable carriers may include surfactants, emulsifiers, oils, salts, and the like.

[0195] These compositions can be manufactured by known methods, for example, by mixing one or more ascalosides and one or more pesticides with one or more agronomically acceptable carriers such as liquid solvents or solid carriers, and optionally using additional components including, but not limited to, surfactants including emulsifiers, dispersants, foaming agents, colorants, processing aids, lubricants, fillers, strengtheners, flame retardants, light stabilizers, UV absorbers, weather stabilizers, plasticizers, release agents, fragrances, heat retention additives (e.g., silica), crosslinking agents, antioxidants, defoamers, buffers, pH adjusters, compatibility agents, drift control additives, fillers / tackeners, tackifiers, plant penetration agents, toxicity mitigators, spreading agents, wetting agents, etc. In some embodiments, such formulations may include one or more additional pesticides and / or one or more plant or plant product treatment compounds. Furthermore, some compositions are residual in that they are not easily washed away from plant leaves during rain and can therefore provide protection from pests during and after rainy weather. The additional components described herein can be added directly to the formulation as described above, or alternatively, they can be added separately, for example, at the time of application. In some embodiments, wetting agents, emulsifiers, spreading agents, etc., are used in the formulation. The formulation includes concentrated forms in which the pesticide is present at a concentration of 0.001 to 98.0%, with the remaining components being an agrochemically acceptable carrier / adjuvant.

[0196] Such formulations, particularly those containing less than 50 percent of the compound, may sometimes be used directly, but they may also be diluted with other agronomically acceptable carriers to form more diluted treatment formulations. These latter formulations may contain the compound described herein at concentrations as low as 0.001–0.1 percent.

[0197] The formulation may further contain “adjuvant surfactants” to promote the deposition, wetting, and penetration of the compound into target crops and organisms. These “adjuvant surfactants” may optionally be used as components of the formulation or as tank mixtures. The amount of adjuvant surfactant typically varies from 0.01 to 1.0 volume percent, preferably 0.05 to 0.5 volume percent, based on the spray volume of water. Suitable adjuvant surfactants include ethoxylated nonylphenol, ethoxylated synthetic or natural alcohols, esters or sulfosuccinate salts, ethoxylated organosilicones, ethoxylated fatty amines, blends of surfactants with mineral or vegetable oils, crop oil concentrates (mineral oil (85%) + emulsifier (15%)), nonylphenol ethoxylate, benzyl cocoalkyldimethylquaternary ammonium salts; petroleum hydrocarbons, alkyl esters, organic acids, and blends of anionic surfactants. Examples include, but are not limited to, C9-Cu alkyl polyglycosides, phosphoric acid alcohol ethoxylates, natural primary alcohols (C12-C16) ethoxylates, di-sec-butylphenol EO-PO block copolymers, polysiloxane-methyl cap, nonylphenol ethoxylate + urea ammonium nitrate, emulsified methylated seed oils, tridecyl alcohol (synthetic) ethoxylate (8EO), tallow amine ethoxylate (15EO), and PEG(400)-dioleate-99. Formulations may also include oil-in-water emulsions. In some embodiments, organic solvents may be incorporated as auxiliary liquid solvents when the agronomically acceptable carrier is water. Suitable liquid solvents include, for example, aromatic compounds (e.g., xylene, toluene, and alkylnaphthalenes), chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons (e.g., chlorobenzene, chloroethylene, and methylene chloride), aliphatic hydrocarbons (e.g., cyclohexane), paraffins (e.g., petroleum fractions, mineral, and vegetable oils), alcohols (e.g., butanol or glycols and their ethers and esters), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone), and strongly polar solvents (e.g., dimethylformamide and dimethyl sulfoxide).Other examples of organic solvents include, but are not limited to, xylene, propylbenzene fraction, or mixed naphthalene fraction, mineral oil, substituted aromatic organic liquids such as dioctyl phthalate; kerosene, dialkylamides of various fatty acids, in particular dimethylamides of fatty glycols and glycol derivatives such as n-butyl ether, ethyl ether or methyl ether of diethylene glycol, methyl ether of triethylene glycol, petroleum fraction or mineral oil, aromatic solvents, hydrocarbons such as paraffin oil, terpene solvents, rosin derivatives, aliphatic ketones such as cyclohexanone, complex aliphatic and aromatic alcohols such as 2-ethoxyethanol, esters of the aforementioned vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, and tung oil. A mixture of two or more organic liquids may be used in the preparation of certain emulsifying concentrates. Examples of organic liquids include xylene and propylbenzene fractions, with xylene being most preferred in some cases. The surface-active dispersant is typically used in liquid formulations in amounts of 0.1 to 20 weight percent based on the combined weight of the dispersant with one or more of the compounds.

[0198] Suitable agro-acceptable solid carriers include, for example, ammonium salts and pulverized natural minerals (e.g., kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth), pulverized synthetic minerals (e.g., highly dispersed silica, alumina, and silicates), pulverized and fractionated natural rocks (e.g., calcite, marble, pumice, sepiolite, and dolomite), synthetic granules of inorganic and organic meals, and granules of organic materials (e.g., sawdust, coconut husks, corn cobs, and tobacco stalks). In some embodiments, the dry composition may include powders, etc.

[0199] Suitable emulsifiers and foaming agents include, for example, nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers, for example, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, and aryl sulfonates) and protein hydrolysates.

[0200] Suitable dispersants include, for example, lignin-sulfite wastewater and methylcellulose. Carboxymethylcellulose in the form of powder, granules or lattice, as well as natural and synthetic polymers, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and tackifiers such as natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids, can be used in the disclosed compositions. Examples of nonionic emulsifiers useful for preparing emulsifiable concentrates include polyalkylene glycol ethers and condensation products of alkylphenols and arylphenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as ethoxylated alkylphenols, and carboxylic acid esters solubilized with polyols or polyoxyalkylenes. Cationic emulsifiers include quaternary ammonium compounds and aliphatic amine salts. Anionic emulsifiers include oil-soluble salts of alkylarylsulfonic acids (e.g., calcium), oil-soluble salts of sulfated polyglycol ethers, and suitable salts of phosphorylated polyglycol ethers. Other additives may include, for example, mineral oils and vegetable oils.

[0201] "Surfactants" (which can typically make up about 0.5% to about 10% of a wetting powder) include nonionic surfactants such as sulfonated lignin, condensed naphthalene sulfonates, naphthalene sulfonates, alkylbene sulfonates, alkyl sulfonates, or ethylene oxide adducts of alkylphenols or mixtures thereof.

[0202] Inorganic pigments, such as colorants like iron oxide, titanium dioxide, and Prussian blue; organic dyes, such as alizarin dyes, azo dyes, and metal phthalocyanine dyes; and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc may also be included in the composition.

[0203] Methods for preparing solid and liquid compositions for pesticide use are generally known and can be used in accordance with this disclosure (such methods include incorporating one or more ascalosides and one or more pesticides into such compositions). In some embodiments, the compositions can be available as liquid concentrates, ready-to-use (RTU) liquid sprays, dust, or solids, depending on the user's needs. In some embodiments, the compositions according to this disclosure can be in the form of granular materials (including dust, pellets, soluble powders, fluid powders, water-dispersible granules, etc.). In some embodiments, the compositions according to this disclosure can be in liquid form (e.g., solutions, suspensions, or emulsions). In some embodiments, the compositions are in the form of granular materials treated with a liquid containing one or more ascalosides and one or more additional pesticides. In some embodiments, the compositions containing one or more ascalosides and one or more pesticides can be formed into fibers or filaments, and in some such embodiments, textiles or nonwovens (e.g., films) can be produced therefrom. In some embodiments, the compositions provided herein are pelletized. In some embodiments, the compositions provided herein are in the form of films, e.g., plastic mulch. Any of the solid compositions provided herein can be optionally coated via methods generally known in the art to delay the release of one or more ascalosides and one or more pesticides. The selected formulation depends on the intended use of the product.

[0204] Dust containing the compounds of this disclosure can be prepared by closely mixing one or more of the compounds in powder form with a suitable dust-rich agricultural carrier, such as kaolin clay or terrestrial volcanic rock. The dust may suitably contain about 1 to about 10 weight percent of the compound, based on the total weight of the dust.

[0205] The wet powder may be agglomerated or compressed to form water-dispersible granules. These granules contain a mixture of the compound, an inert carrier suitable for granular applications, and a surfactant. The concentration of the compound is typically about 0.1% to about 90% by weight. "Inert carriers suitable for granular applications" are typically pyrophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, and refined silicates. In such operations, the finely divided carrier and surfactant are typically blended with the compound and ground.

[0206] An aqueous suspension can be prepared when the compound is dispersed in an aqueous vehicle at a concentration typically ranging from about 5% to about 50% by weight. The suspension can be prepared by finely grinding the compound and vigorously mixing it with water, a surfactant, and a dispersant vehicle. Inert components such as inorganic salts and synthetic or natural gums may also be used to increase the density and / or viscosity of the aqueous vehicle, as desired.

[0207] The amounts of one or more ascalosides and one or more pesticides contained in such formulations can vary. In certain specific embodiments, the amounts of one or more ascalosides and one or more pesticides are synergistically effective. Typically, the formulation contains one or more ascalosides in a lower weight percentage than the one or more pesticides.

[0208] In certain embodiments, the provided combination is characterized in that the amount of one or more ascalosides represents a very low percentage of the formulation. In certain embodiments, the provided combination is characterized in that the ascaloside is present in an amount of less than 1% by weight relative to the other active ingredients(s). In certain embodiments, the provided combination is characterized in that the ascaloside is present in an amount of less than 0.1% by weight relative to the other active ingredients(s). In certain embodiments, the provided combination is characterized in that the ascaloside is present in an amount of less than 0.05% by weight relative to the other active ingredients(s). In certain embodiments, the provided combination is characterized in that the ascaloside is present in an amount of less than 0.01% by weight relative to the other active ingredients(s). In certain embodiments, the provided combination is characterized in that the ascaloside is present in an amount of less than 0.001% by weight relative to the other active ingredients(s).

[0209] In certain embodiments, the co-administration of one or more ascalosides and one or more pesticides described herein can be used to treat living plants or plant parts, soil surrounding plants, soil in which seeds / seedlings are planted, or plants or plant parts after harvest. In some embodiments, one or more ascalosides and one or more pesticides are applied to plant parts, i.e., one or more parts of a plant, such as roots, stems, leaves, seeds, and / or flowers. Such methods can be carried out at any one or more stages of the plant life cycle, e.g., from seeds, seedlings, growing plants to just before harvest. In certain embodiments, the co-administration includes spraying one or more ascalosides and one or more pesticides onto the leaves of a plant. In certain embodiments, the co-administration includes applying a powder or solid to the leaves of a plant. In certain embodiments, the co-administration includes treating plant seeds with one or more ascalosides and one or more pesticides (e.g., before planting). In certain embodiments, co-administration includes treating the stems, branches, or stalks of a plant with one or more ascalosides and one or more pesticides. In certain embodiments, co-administration includes applying one or more ascalosides and one or more pesticides to the soil in which the plant is growing, or to the soil in which the plant will grow.

[0210] The disclosed treatment methods can protect growing plants in some embodiments, as described in U.S. Patent No. 10,136,595, which is incorporated herein by reference in its entirety. For example, such methods can promote pathogen resistance and / or induce one or more plant defense responses (thereby inhibiting pathogen growth and / or parasitism) in plants to which one or more ascalosides and one or more pesticides are applied (or near them). Pathogens to which resistance can be promoted by the methods disclosed include, but are not limited to, Oomycetes, bacteria, nematodes, viruses, and insects, for example, Pseudomonas syringae, Phytophthora infestans, Blumeria graminis, Heterodera schachtii, Meloidogyne incognita, Meloidogyne hapla, and turnip crinkle virus.

[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 on the selection of one or more additional pesticides. For example, by combining a given pesticide with one or more ascalosides, the known activity of the pesticide against a particular pathogen in a particular crop can be enhanced.

[0212] The exact method of treating plants or soil with one or more ascalosides and one or more pesticides is not particularly limited. Treatment of plants and / or soil according to this disclosure can be carried out, for example, by immersion, spraying, evaporation, atomization, application, coating, lateral application, or 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 to the soil around plants, and / or granular compositions can be provided for furrow application or lateral application. In some embodiments, the methods provided herein include treating seeds before planting.

[0213] The types of plants that can be treated according to the methods of this disclosure are not particularly limited and may include, 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 thaliana, tomato, barley, potato, sweet potato, yam, cotton, soybean, strawberry, sugarcane, sugar beet, corn, rice, wheat, rye, oat, sorghum, millet, legume, pea, apple, banana, pear, cherry, peach, plum, apricot, almond, grape, kiwi, mango, melon, papaya, walnut, hazelnut, pistachio, raspberry, blackberry, loganberry, blueberry, cranberry, orange, lemon, grapefruit, tangerine, lettuce, carrot, onion, broccoli, cabbage, avocado, cocoa, cassava, cotton, and flax.

[0214] In some embodiments, the compositions and methods provided herein can be used to protect any plant from fungal or bacterial diseases and to promote the health, growth, and yield of plants, including but not limited to monocots and dicots.Examples of plant species of interest include maize (Zea mays), Brassica species (e.g., B. napus, B. rapa, B. juncea), especially Brassica species useful as a source of seed oil, alfalfa (Medicago sativa), rice (Oryza sativa), rye (Secale cereale), sorghum (Sorghum bicolor, Sorghum vulgare), millet (e.g., pearl millet (Pennisetum glaucum), proso millet (Panicum miliaceum), foxtail millet (Setaria italica), finger millet (Eleusine coracana)), sunflower (Helianthus annuus), safflower (Carthamus tinctorius), wheat (Triticum aestivum), soybean (Glycine max), tobacco (Nicotiana tabacum), and 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 fruits (Citrus spp.), cocoa (Theobroma cacao), tea (Camellia sinensis), banana (Musa spp.), avocado (Persea americana), fig (Ficus casica), guava (Psidium guajava), mango (Mangifera indica), olive (Olea europaea), papaya (Carica papaya), cashew (Anacardium occidentale), macadamia (Macadamia) This includes, but is not limited to, plants such as integrifolia, almonds (Prunus amygdalus), sugar beets (beta vulgaris), sugarcane (Saccharum spp.), oats, barley, vegetables, ornamental plants, and conifers.

[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), pearl beans (Cajanus cajan), yams, kudzu, legumes, peas (I spp.), as well as members of genus i such as cucumbers (C. sativus), cantaloupes (C. cantalupensis), and muskmelons (C. melo). Ornamental plants include azaleas (Rhododendron spp.), hydrangeas (Macrophylla hydrangea), hibiscus (Hibiscus rosasanensis), roses (Rosa spp.), tulips (Tulipa spp.), daffodils (Narcissus spp.), petunias (Petunia hybrida), carnations (Dianthus caryophyllus), poinsettias (Euphorbia pulcherrima), and chrysanthemums.

[0216] Examples of coniferous trees that can be used in carrying out the present invention include pines such as Pinus taeda, Pinus elliotii, Pinus ponderosa, Pinus contorta, and Pinus radiata; fir trees such as Pseudotsuga menziesii, Tsuga canadensis, Picea glauca, Sequoia sempervirens, Abies amabilis and Abies balsamea; and cedar trees such as Thuja plicata and Chamaecyparis nootkatensis. In specific embodiments, the plant of the present invention is a crop plant (e.g., corn, alfalfa, sunflower, brassica, soybean, cotton, safflower, peanut, sorghum, wheat, millet, tobacco, etc.). In other embodiments, corn or soybean plants are used.

[0217] The diseases and infestations that can be effectively reduced by treatment with one or more ascalosides and one or more fungicides as disclosed herein may affect any part of a plant (e.g., seeds, roots, stems, leaves, and spikes).

[0218] Fungal and bacterial pathogens that can be controlled by the disclosed combinations include Botrytis cinerea, Cersospora spp, Cercospora sojina, Cercospora beticola, Cercospora canescens, Alternaria solani, Alternaria brassicae, Blumeria graminis f.sp.Tritici, Erysiphe necator, Podosphaera xanthii, Podosphaera leucotricha, Golovinomyces cichoracearum, Erysiphe lagerstroemiae, Erysiphe cichoracearum, Erysiphe graminis, Sphaerotheca pannosa, Sphaerotheca fuliginea, Colletotrichum cereale, Apiognomonia errabunda, Apiognomonia veneta, Colletotrichum gloeosporiodes, Discula fraxinea, Plasmopara viticola, Pseudoperonospora cubensis, Peronospora belbahrii, Bremia lactucae, Peronospora lamii, Plasmopara obduscens, Pythium cryptoirregulare, Pythium aphanidermatum, Pythium irregulare, Pythium sylvaticum, Pythium myriotylum, Pythium ultimum, Phytophthora capsici, Phytophthora nicotianae, Phytophthora infestans, Phytophthora tropicalis, Phytophthora sojae, Fusarium graminearum, Fusarium solani, Fusarium oxysporum, Fusarium graminicola, Gibberella zeae, Colletotrichum graminicola, Phakopsorasp., Phakopsora meibomiae, Phakopsora pachyrizi, Puccinia triticina, Puccinia recondita, Puccinia striiformis, Puccinia graminis, Puccinia spp., Venturia inaequalis, Verticillium spp., Erwinia amylovora, Monilinia fructicola, Monilinia lax, Monilinia fructigena, Uncinula necator, Gymnosporangium sabinae, Hemileia vastatrix, Phakopsora pachyrhizi, Phakopsora meibomiae, Uromyces appendiculatus, Albugo candida, Bremia lactucae, Peronospora pisi, P. brassicae, Pseudoperonospora humuli, Pseudoperonospora cubensis, Pythium ultimum; leafspot, Cladiosporium cucumerinum, Cochliobolus sativus, Cochliobolus miyabeanus, Colletotrichum lindemuthanium, Cycloconium oleaginum, Diaporthe citri, Elsinoe fawcettii, Gloeosporium laeticolor, Glomerella cingulata, Septoria apii, Septoria lycopercisi, Fusarium oxysporum, Rhizoctonia solan, Aspergillus flavus, Fusarium culmorum, Botrytis cinerea, Sclerotinia sclerotiorum, Fusarium culmorum, Phytophthora cactorum, Pythium ultimum, Rhizoctonia solani, Rhizopus oryzae, Sclerotium rolfsii, SeptoriaThis includes, but is not limited to, those selected from the group consisting of 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 others. In some embodiments, ascaloside and one or more fungicides can be used to control forma leaf spot, forma gall, powdery mildew, yellow rust, brown rust, brown spot, septria leaf and rot of cereals, including barley, rye, wheat, and oats.

[0219] Specific diseases include anthracnose (Colletotrichum spp. / Microdochium panattonianum in lettuce, affecting a variety of crops), gray mold (e.g., gray mold / Botrytis cinerea, affecting a variety of crops), downy mildew (affecting crops), white blister / white rust (Albugo candida, typical in Brassica species), Fusarium wilt and rot (Fusarium species including F. solani and F. oxysporum), powdery mildew (affecting crops), rust (several species, e.g., Puccinia sorghi in sweet corn, Uromyces appendiculatus in beans, puccinia allii in spring onions, and affecting a variety of crops, including, e.g., Asian soybean rust), and Rhizoctonia root rot. solani (generally affecting lettuce root rot / wire stem, a cruciferous crop), sclerotinia rot (S. sclerotiorum and S. minor, affecting most vegetable crops), sclerotium rot (Sclerotium rolfsii and S. cepivorum, affecting crops), target spot (alternaria solani, affecting tomatoes), wilt (Pythium, rhizoctonia, phytophthora, fusarium, or aphanomyces, affecting crops), cavity spot (Pythium sulcatum, affecting carrots), root gall (plasmodiophora brassicae, typically in brassicas), tuber disease (affecting potatoes and sweet potatoes), Pythium species (affecting many vegetable crops), leaf blight in carrots (alternaria) Black root rot (affects various species and crops in various crops), and red root complex (affects legumes), Aphanomyces root rot (Aphanomyces euteiches pv.Examples of diseases that affect plants include, but are not limited to, Phaseoli (affecting beans), aschocyta stem rot (affecting peas), black rot (Didymella bryoniae, affecting cucumbers), Alternaria leaf spot (Alternaria cucumerina and A. alternata (Cucurbitaceae)), root rot (Leptosphaeria maculans, affecting brassicas), ring spot (Mycosphaerella brassicicola, affecting brassicas), red blight (Septoria apiicola, affecting celery), Cercospora leaf spot (Cercospora beticola, affecting beets), leaf blight (Septoria petroelini, affecting parsley), Septoria leaf 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 that can be treated, 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, etc., such as Asian soybean rust (ASR), gray mold, leaf spot, frogeye spot, summer blight, damping-off complex, leaf blight, black rot, root rot, belly rot, large white mold, powdery mildew, anthracnose leaf spot, downy mildew, red blight, Fusarium head blight (FHB), sudden death syndrome (SDS), damping-off caused by Fusarium fungi, corn stalk rot, brown rust, black rust, yellow rust, wheat rust, rust, apple scab, wilt, burn, and brown rot. [Examples]

[0221] Example 1: A replicated small-scale plot field study evaluated the phytotoxic effects of applying Blavity® (a commercially available fungicide blend containing prothioconazole (280 g / L) and flaxapyroxad (200 g / L)). The field study was configured to mimic a typical grower's application of Blavity to soybeans for the control of Asian soybean rust. Blavity was applied twice, 45 and 60 days after emergence. In some treatment groups, ascaloside (a commercially available formulation under the trade name Phytalix®, ascr#18) was applied at a rate of 50 mg / acre 15 days prior to the first Blavity application. The phytotoxic effects were scored in all groups 28 days after the second Blavity application, and it was found that the treatment groups including the prior application of ascaloside showed significantly reduced phytotoxic effects compared to the treatment groups without ascaloside treatment (Figure 1). In this study, the ratio of ascaloside applied to the antifungal component in Blavity is approximately 5700:1.

[0222] Example 2: A second replicated small-scale plot field trial evaluated the phytotoxic effects of Blavity® application. The field trial was configured to mimic typical grower application of Blavity to soybeans for the control of Asian soybean rust. Blavity was applied twice, 45 and 60 days after emergence. In some treatment groups, ascaloside (ascr#18 formulation, marketed under the trade name Phytalix®) was applied at a rate of 50 mg / acre 15 days prior to the first Blavity application. The phytotoxic effects were scored in all groups 35 days after the second Blavity application, and it was found that treatment groups including prior application of ascaloside showed significantly reduced phytotoxic effects compared to treatment groups without ascaloside treatment (Figure 2). In this study, the ratio of ascaloside applied to the fungicidal component in Blavity was approximately 5700:1.

[0223] Example 3: Example 3 is carried out in the same manner as Example 1, except that the ascaloside tank is mixed and applied simultaneously with the first Blavity treatment.

[0224] Example 4: The stability of combinations of PHYTALIX® (ascr#18 formulation) with various other pesticides was studied. Two sets of samples were prepared, replicated by diluting tank mixture formulations (e.g., PHYTALIX® and commercial products in water at the ratios indicated on their labels) and adding the PHYTALIX® concentrate, which is a formulation blend, directly to the commercial formulation. Samples were stored at room temperature and 40°C (for accelerated degradation), and the PHYTALIX® content was periodically monitored using HPLC / MS quantification. The results for 6 months are summarized below. The data surprisingly demonstrate that combinations of PHYTALIX® with various pesticides in both concentrated formulations and tank mixture concentrates are stable for at least 6 months or at least 12 months of shelf life (e.g., with respect to ascaloside content), despite the incredibly low ascaloside content present in each formulation. This finding is particularly surprising in light of the fact that formulation mixtures of chemical and biological components can generally be quite difficult due to the issue of incompatibility with each other. [Table 1] [Table 2]

[0225] The compounds, compositions, and methods of this application are intended to encompass modifications and adaptations developed using information from the embodiments described herein. Adaptations or modifications of the methods and processes described herein may be carried out by those skilled in the art. The use of headings in this disclosure is provided for the convenience of the reader.

[0226] The presence and / or placement of headings are not intended to limit the scope of the subject matter described herein. Unless otherwise specified, embodiments located in one section of this application apply throughout this application, both individually and in combination, to other embodiments. Throughout the description, where compositions, compounds, or products are described as having, containing, or comprising certain components, or where processes and methods are described as having, containing, or comprising certain steps, it is intended that there are articles, devices, and systems of this application that are essentially composed of or comprise the listed components, and processes and methods of this application that are essentially composed of or comprise the listed processing steps. It should be understood that the order of steps or sequences for performing a particular operation is not important, as long as the described method is operable. Furthermore, two or more steps or operations may be performed simultaneously.

[0227] All publications and patent applications described herein are indicators of the level of skill of those skilled in the art in which the invention relates. All publications and patent applications are incorporated herein by reference to the same extent as each individual publication or patent application is specifically and individually indicated to be incorporated by reference. Although the invention described herein is described in some detail as an illustration and example for the purpose of clarifying understanding, it will be apparent that certain changes and modifications may be practiced within the scope of the appended claims.

Claims

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

2. A method for mitigating the phytotoxic effects of a pesticide, comprising administering one or more ascalosides to a plant, a part of a plant, or soil surrounding the plant or part of a plant, wherein the plant, a part of a plant, or soil surrounding the plant or part of a plant is or has been exposed to the pesticide.

3. A method for mitigating the phytotoxic effects of a pesticide, comprising administering the pesticide to a plant, a part of a plant, or soil surrounding the plant or part of a plant, wherein the plant, a part of a plant, or soil surrounding the plant or part of a plant has been or is currently exposed to one or more ascalosides.

4. The method according to any one of claims 1 to 3, wherein the pesticide is a fungicide.

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

6. The method according to claim 5, wherein the antifungal agent is a strobilurin selected from the group consisting of azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, phenamistrobin, dimoxystrobin, fluoxastrobin, methaminostrobin, mandestrobin, pyrametostrobin, pyrazoxystrobin, kresoxime-methyl, phenamidone, or famoxadone.

7. The method according to claim 5, wherein the fungicide is a benzamide fungicide selected from the group consisting of benodanil, flurenoxadiazam, flutolanil, mebenil, mepronil, fluopyram, benzohydroxamidic acid, flumetobel, flupicolide, flupimoide, thioximide, trchlamide, zarilamide, and zoxamide.

8. The aforementioned fungicide, Oxathiine fungicide, francarboxamide fungicide, Pyrazinecarboxamide fungicide, Pyrazole carboxamide fungicide, and The method according to claim 5, selected from the group consisting of pyridinecarboxamide fungicides.

9. The method according to claim 8, wherein the fungicide is selected from the group consisting of carboxyne, oxycarboxyne, fenflam, flucarbanil, metofloxam, pyraziflumid, benzovindiflupir, bixafen, fluveneteram, fluindapir, fluxapyroxad, flametopyr, impilfluxam, isoflucipram, isopyrazam, penflufen, penthiopyrad, pidflumetofen, pyrapropoin, sedaxane, etaboxam, tifluzamide, boscalid, and cyclobutrifluram.

10. The method according to any one of claims 1 to 3, wherein the pesticide is an insecticide.

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

12. The insecticides mentioned above include acephate, azamethiphos, adinphosethyl, adinphosmethyl, bromophos, bromophosethyl, kazusaphos, chlorethoxyphos, chlorpyrifos, chlorfenbinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methylsulfone, diariphos, diazinon, dichlorvos, diclotophos, dimethoate, disulfoton, ethione, etoprophos, etrimphos, famfur, phenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazophos, honofos, formothion, fothiazate, heptenophos, isazofos, isothioate, isoxathion, malathion, methacryphos, and meta The method according to claim 11, selected from the group consisting of midophos, methidathion, methylparathion, mevinphos, monoclotophos, naled, omethoate, oxydemetonmethyl, paraoxone, parathion, parathionmethyl, fenthoate, phosalon, phospholan, phosphocarb, phosmet, phosphamidone, phorate, foxim, pirimiphos, pirimiphosmethyl, profenophos, propaphos, proetamphos, prothiophos, pyraclophos, pyridapention, quinalphos, sulprophos, temephos, terbuphos, tebupyrimphos, tetrachlorvinphos, thymetone, triazophos, trichlorfon, and bamidothion.

13. The method according to claim 11, wherein the insecticide is selected from the group consisting of aranicarb, aldicarb, 2-sec-butylphenylmethylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, chloetocarb, ethiofencarb, phenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pyrimicarb, propoxul, thiodicarb, thiophanox, triazamate, and UC-51717.

14. The insecticides include acrinatin, allethrin, alphamethrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, α-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), biorethmetrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, citrin, cyphenothrin, deltamethrin The method according to claim 11, selected from the group consisting of phosphorus, empenthrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucitrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrin (natural product), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, and zeta-cypermethrin.

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

16. The method according to claim 15, wherein the arthropod growth regulator is selected from the group consisting of a) benzoylurea: chitin synthesis inhibitors such as chlorfluazurone, diflubenzuron, fluazurone, flucycloxurone, flufenoxurone, hexaflumurone, lufenuron, novaron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, and chlorfentadine; b) ecdysone antagonists such as halofenozide, methoxyfenozide, and tebufenozide; c) juvenile hormone-like substances such as pyriproxyfen, siethoprene (containing S-methoprene), and phenoxycarb; and d) lipid biosynthesis inhibitors such as spirodiclofen.

17. The method according to any one of claims 1 to 3, wherein the pesticide is a pharmaceutical additive.

18. The method according to claim 17, wherein the formulation additive is selected from adjuvants, solvents, surfactants, wetting agents, defoaming agents, preservatives, dyes, anticoagulants, compatibilizers, and any two or more combinations thereof.

19. The method according to any one of claims 1 to 3, wherein the pesticide is a fertilizer or a plant nutrient preparation.

20. The method according to any one of claims 1 to 19, characterized in that the co-administration results in a lower level of phytotoxicity to the crop to which it is applied compared to the application of one or more pesticides that do not contain one or more ascalosides.

21. The method according to claim 20, characterized in that one or more phytotoxic symptoms in the treated crop are reduced by at least 10% compared to the use of an equivalent composition lacking one or more ascalosides.

22. The method according to claim 21, wherein one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent treatment lacking the one or more ascalosides.

23. The method according to claim 20, characterized in that one or more plant toxicity symptoms are substantially absent with the use of an equivalent composition lacking the one or more ascalosides.

24. The method according to claim 20, wherein the effects of the plant toxicity are selected from the group consisting of poor germination; seedling death; death or damage of rapidly growing succulent tissue; inhibition or delay of plant development; irregular or distorted plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or dots on leaves; dead leaf tips or margins; dead regions between leaf veins; and any two or more combinations thereof.

25. The method according to any one of claims 1 to 24, wherein the increased total yield of the plant is greater than the yield of a plant treated with a pesticide without co-administration of one or more ascalosides.

26. The method according to any one of claims 1 to 25, wherein the co-administration comprises applying the pesticide and the one or more ascalosides in the form of separate formulations.

27. The method according to any one of claims 1 to 25, wherein the co-administration comprises applying the pesticide and one or more ascalosides in the form of a single formulation.

28. The one or more ascalosides described above have structure (I), 【Chemistry 15】 During the ceremony, Z is replaced by C of arbitrary choice. ２－４０ It is an aliphatic group, R ａ and R ｂ each independently is -H, or C １－２０ aliphatic, C １－２０ acyl, C １－２０ heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bonding functional group, sulfur bonding functional group, silicon bonding functional group, C ２－２０ carbonate (e.g., moiety -C(O)OR ｃ ), C ２－２０ carbamate (e.g., moiety -C(O)N(R ｃ )), C ２ ), C ２－２０ thioester (e.g., moiety -C(S)R ｃ ), C ２－２０ thiocarbonate (e.g., moiety -C(S)OR ｃ ), C ２－２０ dithiocarbonate (e.g., moiety -C(S)SR ｃ ), C １－２０ thiocarbamate (e.g., moiety -C(S)N(R ｃ )), C ２ ), a sugar moiety, a peptide, a polymer chain, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety, and is an optionally substituted moiety selected from the group consisting of, R ｃ is independently at each occurrence -H, optionally substituted C １－１２ aliphatic, optionally substituted C １－１２ heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety, and R ａ and R ｂ together may form an optionally substituted ring optionally containing one or more heteroatoms and optionally containing one or more unsaturated sites, the method according to any one of claims 1 to 27.

29. Z is i. -CH(CH ３ )-R １ (R １ C is replaced by an optional substitution. １－４０ (It is an aliphatic group.) ii. -CH(CH ３ )-(CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. iii. -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. iv. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. v. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. vi. - (CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. vii. - (CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. viiii. - (CH ２ ) ｎ -CH(OH)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules via carbon-containing linker moieties), and ix. -(CH ２ ) ｎ -C(O)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, and R ２ is -H, a metal cation, an optionally substituted C １－２０ aliphatic group, an optionally substituted C １－２０ heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety). x. -CH(CH ３ )- (CH ２ ) ｎ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ is independently -H, an optionally substituted C １－２０ aliphatic group, an optionally substituted C １－２０ heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety). xi. -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xii. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH ２ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xiii. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH ２ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xiv. - (CH ２ ) ｎ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xv. - (CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xvi. - (CH ２ ) ｎ -CH(OH)-CH ２ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xvii. - (CH ２ ) ｎ -C(O)-CH ２ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules or via carbon-containing linker moieties), as well as xviiii. Optionally unsaturated and optionally substituted C, terminated at a chain end containing a nitrogen-containing functional group, an oxygen-containing functional group, or a sulfur-containing functional group. ２－４０ The method according to claim 28, selected from the group consisting of side chains.

30. The method according to any one of claims 1 to 29, wherein one or more ascalosides include ascr#18.

31. The method according to any one of claims 1 to 29, wherein one or more ascalosides include oscr#16.

32. A pesticide composition comprising a pesticide and one or more ascalosides, characterized in that application of the composition to plants results in lower plant toxicity than application of an equivalent composition without the one or more ascalosides.

33. The composition according to claim 32, wherein the pesticide is a fungicide.

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

35. The composition according to claim 33, wherein the fungicide is a strobilurin selected from the group consisting of azoxystrobin, picoxystrobin, trifloxystrobin, orysastrobin, pyraclostrobin, phenamistrobin, dimoxystrobin, fluoxastrobin, methaminostrobin, mandestrobin, pyrametostrobin, pyrazoxystrobin, kresoxime-methyl, phenamidone, or famoxadone.

36. The composition according to claim 33, wherein the fungicide is a benzamide fungicide selected from the group consisting of benodanil, flurenoxadiazam, flutolanil, mebenil, mepronil, fluopyram, benzohydroxamidic acid, flumetobel, flupicolide, flupimoide, thioxymide, trchlamide, zarilamide, and zoxamide.

37. The aforementioned fungicide, Oxathiine fungicide, francarboxamide fungicide, Pyrazinecarboxamide fungicide, Pyrazole carboxamide fungicide, and The composition according to claim 33, selected from the group consisting of pyridinecarboxamide fungicides.

38. The composition according to claim 33, wherein the fungicide is selected from the group consisting of carboxyne, oxycarboxyne, fenflam, flucarbanil, metofloxam, pyraziflumid, benzovindiflupir, bixafen, fluveneteram, fluindapir, fluxapyroxad, flametopyr, impilfluxam, isoflucipram, isopyrazam, penflufen, penthiopyrad, pidflumetofen, pyrapropoin, sedaxane, etaboxam, tifluzamide, boscalid, and cyclobutrifluram.

39. The composition according to claim 32, wherein the pesticide is an insecticide.

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

41. The insecticides mentioned above include acephate, azamethiphos, adinphosethyl, adinphosmethyl, bromophos, bromophosethyl, kazusaphos, chlorethoxyphos, chlorpyrifos, chlorfenbinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methylsulfone, diariphos, diazinon, dichlorvos, diclotophos, dimethoate, disulfon, ethione, etoprophos, etrimphos, famfur, phenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazophos, honofos, formothion, fothiazate, heptenophos, isazofos, isothioate, isoxathion, malathion, methacryphos, methammi The composition according to claim 39, selected from the group consisting of dophos, methidathion, methylparathion, mevinphos, monoclotophos, naled, omethoate, oxydemetonmethyl, paraoxone, parathion, parathionmethyl, fenthoate, phosalon, phosphoran, phosphocarb, phosmet, phosphamidone, phorate, foxim, pirimiphos, pirimiphosmethyl, profenophos, propaphos, proetamphos, prothiophos, pyraclophos, pyridapention, quinalphos, sulprophos, temephos, terbuphos, tebupyrimphos, tetrachlorvinphos, thymetone, triazophos, trichlorfon, and bamidothion.

42. The composition according to claim 39, wherein the insecticide is selected from the group consisting of aranicarb, aldicarb, 2-sec-butylphenylmethylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, chloetocarb, ethiofencarb, phenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pyrimicarb, propoxul, thiodicarb, thiophanox, triazamate, and UC-51717.

43. The insecticides include acrinatin, allethrin, alphamethrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, α-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), biorethmetrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, citrin, cyphenothrin, deltamethrin The composition according to claim 39, selected from the group consisting of phosphorus, empenthrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucitrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrin (natural product), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, and zeta-cypermethrin.

44. The composition according to claim 39, wherein the insecticide is an arthropod growth regulator.

45. The composition according to claim 44, wherein the arthropod growth regulator is selected from the group consisting of a) benzoylurea: chitin synthesis inhibitors such as chlorfluazurone, diflubenzuron, fluazurone, flucycloxurone, flufenoxurone, hexaflumurone, lufenuron, novaron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, and chlorfentadine; b) ecdysone antagonists such as halofenozide, methoxyfenozide, and tebufenozide; c) juvenile hormone-like substances such as pyriproxyfen, siethoprene (containing S-methoprene), and phenoxycarb; and d) lipid biosynthesis inhibitors such as spirodiclofen.

46. The composition according to claim 32, wherein the pesticide is a pharmaceutical additive.

47. The composition according to claim 46, wherein the formulation additive is selected from adjuvants, solvents, surfactants, wetting agents, defoaming agents, preservatives, dyes, anticoagulants, compatibilizers, and any two or more combinations thereof.

48. The composition according to claim 32, wherein the pesticide is a fertilizer or a plant nutrient preparation.

49. The composition according to any one of claims 32 to 48, characterized in that one or more phytotoxic symptoms in crops treated with the composition are reduced by at least 10% compared to the use of an equivalent composition lacking one or more ascalosides.

50. The composition according to claim 49, wherein one or more phytotoxic symptoms are reduced by at least 15%, at least 20%, at least 25%, at least 35%, at least 50%, at least 75%, or at least 90% compared to the use of an equivalent treatment lacking the one or more ascalosides.

51. The composition according to claim 49 or 50, characterized in that one or more phytotoxic symptoms are substantially absent with the use of an equivalent composition lacking the one or more ascalosides.

52. The composition according to any one of claims 32 to 51, wherein lower plant toxicity includes reduction of one or more effects selected from the group consisting of poor germination; seedling death; death or damage of rapidly growing succulent tissue; inhibition or delay of plant development; irregular or deformed plants, fruits, or leaves; browning or copper discoloration of leaves or fruits; dead spots or blemishes on leaves; dead leaf tips or margins; dead areas between leaf veins; and any combination of two or more of these.

53. The one or more ascalosides described above have structure (I), 【Chemistry 16】 During the ceremony, Z is replaced by C of arbitrary choice. ２－４０ It is an aliphatic group, R ａ and R ｂ Each of these independently corresponds to -H or C １－２０ aliphatic, C １－２０ Ashiru, C １－２０ Heteroaliphatic, aryl, heteroaryl, hydroxyl protecting group, phosphorus bond functional group, sulfur bond functional group, silicon bond functional group, C ２－２０ Carbonates (e.g., partial-C(O)OR) ｃ ), C ２－２０ Carbamates (e.g., partial-C(O)N(R) ｃ ) ２ ), C ２－２０ Thioesters (e.g., partial-C(S)R) ｃ ), C ２－２０ Thiocarbonates (e.g., partial-C(S)OR) ｃ ), C ２－２０ Dithiocarbonates (e.g., partial-C(S)SR) ｃ ), C １－２０ Thiocarbamates (e.g., partial-C(S)N(R) ｃ ) ２ ), a portion optionally substituted from the group consisting of a sugar portion, a peptide, a polymer chain, or bonding to another ascaloside molecule or linkage via a carbon-containing linker portion, R ｃ However, in each occurrence, independently, -H and C are substituted by any choice. １－１２ Aliphatic C, optionally substituted １－１２ Selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, polymer chain, or linkage to another ascaloside molecule or via a carbon-containing linker moiety, R ａ and R ｂ The composition according to any one of claims 32 to 52, wherein together they can form an optionally substituted ring containing optionally one or more heteroatoms and optionally one or more unsaturated moieties.

54. Z is i. -CH(CH ３ )-R １ (R １ C is replaced by an optional substitution. １－４０ (It is an aliphatic group.) ii. -CH(CH ３ )-(CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. iii. -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. iv. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. v. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. vi. - (CH ２ ) ｎ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. vii. - (CH ２ ) ｎ -CH=CH-CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This includes attachment to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. viiii. - (CH ２ ) ｎ -CH(OH)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ (This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules via carbon-containing linker moieties), and ix. - (CH ２ ) ｎ -C(O)-CH ２ -CO ２ R ２ (n is an integer from 1 to 40, R ２ C is a -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This involves bonding to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, glycosides, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via a carbon-containing linker moiety. x. -CH(CH ３ )-(CH ２ ) ｎ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xi. -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xii. -CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH ２ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xiii. -CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH ２ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xiv. - (CH ２ ) ｎ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xv. - (CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xvi. - (CH ２ ) ｎ -CH(OH)-CH ２ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes linkage to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linkage via carbon-containing linker moieties. xvii. - (CH ２ ) ｎ -C(O)-CH ２ -CON(R ３ ) ２ (n is an integer from 1 to 40, and each R ３ These are independently replaced by -H and C of any choice. １－２０ Aliphatic group, optionally substituted C １－２０ This includes heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or linkage to other ascaloside molecules or via carbon-containing linker moieties), as well as xviiii. Optionally unsaturated and optionally substituted C, terminated at a chain end containing a nitrogen-containing functional group, an oxygen-containing functional group, or a sulfur-containing functional group. ２－４０ The composition according to claim 53, selected from the group consisting of side chains.

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

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

57. A composition in solid form according to any one of claims 32 to 56.

58. The composition according to claim 57, wherein the solid form includes powder or granules.

59. A composition in liquid form according to any one of claims 32 to 56.

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

61. The composition according to claim 59 or 60, wherein the composition is storage stable for a period exceeding six months.

62. The composition according to any one of claims 32 to 61, further comprising one or more additional components selected from the group consisting of surfactants including emulsifiers, dispersants, foaming agents, colorants, processing aids, lubricants, fillers, reinforcing agents, flame retardants, light stabilizers, ultraviolet absorbers, weather stabilizers, plasticizers, release agents, fragrances, heat retention additives (e.g., silica), crosslinking agents, antioxidants, defoaming agents, buffers, pH adjusters, compatibility agents, drift control additives, bulking agents / tackeners, tackifiers, plant penetration agents, toxicity mitigators, spreading agents, and wetting agents.

63. The composition according to any one of claims 32 to 62, wherein the fungicide and the ascaloside are present in a weight ratio of fungicide:ascaloside greater than 1000:1.

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