Combination of ascaloside and herbicide, and method of use.
Combining ascalosides with herbicides addresses the issue of phytotoxicity in selective herbicides, enabling effective weed control with minimal harm to crops by using ascalosides to mitigate herbicide side effects.
Patent Information
- Application Number
- JP2025576388
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-06-29
- Filing Date
- 2024-06-28
- Publication Date
- 2026-07-09
AI Technical Summary
Selective herbicides used in crop-producing areas often have phytotoxic side effects on crop plants, necessitating a solution that can effectively control undesirable plants while minimizing harm to crops.
Combinations of ascalosides with herbicides, either in the same composition or applied simultaneously/sequentially, to reduce phytotoxic effects on crops while killing undesirable plants.
The use of ascalosides with herbicides effectively controls undesirable plants while significantly reducing phytotoxic side effects on treated crops.
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Abstract
Description
[Technical Field]
[0001] Cross-reference of related applications This application claims priority to U.S. Provisional Application No. 63 / 511,172, filed on 29 June 2023, which is incorporated herein by reference in its entirety.
[0002] The present invention provides compositions and methods relating to the use of ascaloside and one or more herbicides. [Background technology]
[0003] Herbicides are well known for controlling undesirable plants. Selective herbicides control specific plants and plant varieties, while non-selective herbicides kill most (if not all) plants that come into contact with them. The majority of herbicides are used for agricultural purposes to selectively remove undesirable plants from crop-producing areas.
[0004] Selective herbicides are frequently used in crop-producing areas. Selective herbicides are used to prevent undesirable plants from growing in the same area where crop-producing plants ("crops") are being cultivated. While herbicides can be highly selective in reducing undesirable plants in a field, they may have phytotoxic side effects on crop plants. [Overview of the Initiative] [Means for solving the problem]
[0005] Combinations of chemicals for preventing, treating, or controlling undesirable plants, and methods of using them are provided. These combinations include at least one ascaloside (or derivatives or analogues of ascaloside) together with at least one herbicide. Ascaloside can be combined with at least one herbicide to reduce the phytotoxic effects of the herbicide on the treated crop while simultaneously killing undesirable plants within the application area. The ascaloside and herbicide may be provided in the same composition, or may be applied together (i.e., substantially simultaneously) or sequentially. The chemicals are applied in an effective amount, i.e., an amount sufficient to control or inhibit the growth of undesirable plants and to reduce the phytotoxic side effects of the herbicide on the crop plants. [Modes for carrying out the invention]
[0006] This disclosure provides compositions and methods relating to the use of one or more ascalosides and one or more herbicides. In some embodiments, this disclosure provides compositions and methods relating to combinations of one or more ascalosides and one or more herbicides, wherein the ascaloside(s) serve as safety agents to reduce the phytotoxic effects of the herbicide(s) on the treated crop. As used herein, the term “ascaloside” includes ascalosides, derivatives, ascaloside analogs, or combinations thereof, as will be further described herein. Ascalosides can be used with any herbicide.
[0007] Ascalosides(or more) and herbicides(or more) may be used in the same composition, or ascalosides(or more) and herbicides(or more) may be applied separately (e.g., in separate formulations), either simultaneously or sequentially. If applied sequentially, the applications should be close enough in time to allow them to work together to produce beneficial results.
[0008] As described, the methods and compositions of the present invention include ascaryosides. Ascaryosides are secondary metabolites produced by nematodes. Many structurally diverse ascaryosides have been identified in nature and are thought to function as an evolutionarily conserved chemical language that nematodes use to control many aspects of their development.
[0009] Ascaryosides are derivatives of the sugar ascarylose, which is a dideoxy sugar lacking hydroxyl groups at its 3- and 6-positions. Ascaryosides have the general structure shown by Formula I:
Chemical formula
[0010] 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 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(CH3)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -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, R 2C is substituted with -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 substituted with -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 substituted with -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 substituted with -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 substituted with -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.
[0011] 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 1-20a bond 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 ascarylose molecule or a linkage 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 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 (xiii)-CH(CH3)-(CH2) n -C(O)-CH2-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 (xiv)-(CH2) 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 (xv)-(CH2) n -CH=CH-CON(R 3 )2 (n is an integer from 1 to 40, and each R3 is, independently, -H, C optionally substituted 1-20 with an aliphatic group, C optionally substituted 1-20 with a heteroaliphatic group, an aromatic group optionally substituted, a heteroaryl group optionally substituted, 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), (xvi)-(CH2) n -CH(OH)-CH2-CON(R 3 )2 (n is an integer from 1 to 40, and each R 3 is, independently, -H, C optionally substituted 1-20 with an aliphatic group, C optionally substituted 1-20 with a heteroaliphatic group, an aromatic group optionally substituted, a heteroaryl group optionally substituted, 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), (xvii)-(CH2) n -C(O)-CH2-CON(R 3 )2 (n is an integer from 1 to 40, and each R 3 is, independently, -H, C optionally substituted 1-20 with an aliphatic group, C optionally substituted 1-20 with a heteroaliphatic group, an aromatic group optionally substituted, a heteroaryl group optionally substituted, 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), or (xviii) a side chain terminating with a chain end containing a nitrogen-containing functional group, an oxygen-containing functional group, or a sulfur-containing functional group, optionally unsaturated, optionally substituted C 2-40 side chain.
[0012] As defined above and described herein, in some embodiments, Z includes a nitrogen-containing functional group, an oxygen-containing functional group, or a 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).
[0013] 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.
[0014] 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).
[0015] 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) c)2) 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.
[0016] 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 R 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.
[0017] 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.
[0018] 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.
[0019] 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).
[0020] 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.
[0021] 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.
[0022] In some embodiments, R b R is an optionally substituted hydroxyl protecting group. In some embodiments, R b is -OR c That is the case.
[0023] In some embodiments, R bR is an optionally substituted phosphorus-bonded functional group. In some embodiments, R b R 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.
[0024] 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. 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.
[0025] 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.
[0026] In a particular embodiment, R a and R b This is 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, and 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 R is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, R a is -H, and R b It is 4-((4-hydroxyphenylethyl)amino)-4-oxobutanoate.
[0027] 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 1-12 The 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.
[0028] 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.
[0029] 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 2 R is phenyl. In some embodiments, R c R is an optionally substituted heteroaryl group. In some embodiments, R c R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R cIt is an optionally substituted 8-12 membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.
[0030] In a particular embodiment, R a and R b Both are -H, and Z is selected from the formulas defined in (i) to (ix) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (i) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (ii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (iii) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (iv) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (v) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (vi) above. In a particular embodiment, R a and R b Both are -H, and Z conforms to equation (vii) above. In a particular embodiment, R a and R b 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, Ra 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.
[0031] As defined above and as described herein, R 2 C is substituted with -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, or optionally substituted aryl groups, or optionally substituted heteroaryl groups.
[0032] 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 2This is C, which has been replaced by an optional substitution. 1-20 It 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 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 2 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 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 certain 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.
[0033] In a particular embodiment, 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.
[0034] In a particular embodiment, R 2 It contains amino acids. In certain embodiments, R 2 It contains peptides. 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.
[0035] In some embodiments, R 2 This 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.
[0036] 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 Bonding to heteroaliphatic groups, optionally substituted aromatic groups, optionally substituted heteroaryl groups, polymer chains, amino acids, peptides, nucleotides, or other ascaloside molecules, or linking via carbon-containing linker moieties, both R 3 The groups together can optionally contain, optionally substitute, and optionally form an unsaturated ring containing one or more additional heteroatoms.
[0037] Several embodiments, each R3 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 them are -H. 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 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 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 3 R 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 the case.
[0038] In some embodiments, R 3 The appearance of C is a substitution of C by choice. 1-20It 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 3 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 3 The appearance of is an optionally substituted aromatic group. In some embodiments, R 3 R is a phenyl compound that is optionally substituted. In some embodiments, R 3 R is phenyl. In some embodiments, R 3 R is an optionally substituted heteroaryl group. In some embodiments, R 3 R is an optionally substituted 5-6 member heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R 3 is an optionally substituted 8-12 member heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In certain embodiments, at least one R 3 R 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.
[0039] 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.
[0040] 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.
[0041] 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 2 Each of these is as defined above and in the genera and subgenera herein.
[0042] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where y, R a , and R b Each of these is as defined above and in the genera and subgenera herein.
[0043] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x and R 2Each of these is as defined above and in the genera and subgenera herein.
[0044] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x is as defined in the genera and subgenera above and herein.
[0045] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where y is an integer from 1 to 20, R 2 These are defined above and in the genera and subgenera of this specification.
[0046] 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.
[0047] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x, R a , R b , and R 3 Each of these is as defined above and in the genera and subgenera herein.
[0048] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where x and R 3Each of these is as defined above and in the genera and subgenera herein.
[0049] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, where y, R a , R b , and R 3 Each of these is as defined above and in the genera and subgenera herein.
[0050] In a particular embodiment, ascaroside is [ka] Selected from the group consisting of, in the formula, y and R 3 Each of these is as defined above and in the genera and subgenera herein.
[0051] 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 substituted with -H, a metal cation, or optionally substituted C 1-20 These are aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.
[0052] 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 C 1-20 These are aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides.
[0053] Specific ascalosides useful in the context of this disclosure include, but are not limited to, ascr#7 and ascr#18. [ka]
[0054] 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.
[0055] 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.
[0056] 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.
[0057] 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.
[0058] 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.
[0059] 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 International Publication No. WO2022 / 024067, which is incorporated herein by reference.
[0060] As shown, according to this disclosure, ascaloside can be used in combination with herbicides as a safety agent to reduce the phytotoxic effects of herbicides on treated crops. Herbicides act by affecting various biological processes related to plants. Exemplary classes of herbicides that can be used in combination with ascaloside include, but are not limited to, PPO herbicides, auxin herbicides, ALS / AHAS herbicides, ACCase inhibitor herbicides, carotenoid biosynthesis inhibitor herbicides, cellulose inhibitor herbicides, EPSP inhibitor herbicides, glutamine synthesis inhibitor herbicides, lipid synthesis inhibitor herbicides, microtubule association inhibitor herbicides, and photosystem inhibitor herbicides.
[0061] PPO herbicides inhibit the protoporphyrinogen oxidase enzyme (PPO). PPO controls the conversion of protoporphyrinogen IX to protoporphyrin IX. The consequence of inhibiting PPO is the accumulation of singlet oxygen in the presence of light. This leads to photo-induced degradation of cellular components, which results in cell leakage, inhibition of photosynthesis, and ultimately bleaching of chloroplast pigments. Exemplary PPO herbicides include, but are not limited to, acronifen, acifluorfen, bifenox, butafenacil, flumioxazine, fomesafen, oxyfluorfen, oxadiazone, saflufenacil, and sulfenthrazone.
[0062] Auxin herbicides are compounds that mimic auxin, a plant hormone that regulates many aspects of growth. Auxin herbicides bind to hormone receptors in plant cells, causing disruption of several growth processes in susceptible plants. Exemplary auxin herbicides include, but are not limited to, aminopyralide, aminocyclopyral, 4-(4-chloro-o-tolyloxy)butyrate (MCPB), clopyralide, dicamba, diflufenzopyr, 2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyrate (2,4-DB), fluroxypyr, mecoprop, 2-methyl-4-chlorophenoxyacetic acid (MCPA), picrolam, quinchlorac, 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), and triclopyr.
[0063] ALS / AHAS herbicides act as inhibitors of acetolactate synthase (ALS), also known as acetohydroxy acid synthase (AHAS), which is a key enzyme in the biosynthesis pathways of branched-chain amino acids isoleucine, leucine, and valine. Examples of ALS / AHAS herbicides include, but are not limited to, bensulfuron, chlorimuron, chloransulam, chlorsulfuron, diclosulam, flazasulfaram, florasulam, flucarbazone, flumetulam, foramsulfuron, halosulfuron, imazametabenz, imazamox, imazapick, imazapyr, imazakine, imazetapir, mesosulfuron, metosulfuron, nicosulfuron, penoxulam, primisulfuron, propoxycarbazone, prosulfuron, pyrithiobac, piroxulam, limsulfuron, sulfomethuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenulon, trifloxysulfuron, and triflusulfuron.
[0064] ACCase inhibitor herbicides inhibit acetyl-CoA carboxylase (ACCase), an enzyme that catalyzes the first step in fatty acid synthesis in plants and is crucial for membrane synthesis. Exemplary ACCase inhibitor herbicides include, but are not limited to, but but also but also but also but also but also but also fluazifop, haloxyfop, diclofop, phenoxaprop, fluazifop, haloxyfop, pinoxadene, quizalofop, cethoxydim, and tralcoxidim.
[0065] Carotenoid biosynthesis inhibitor herbicides directly or indirectly inhibit the production of carotenoids that protect chlorophyll from excessive light and photo-oxidation. Examples of carotenoid biosynthesis inhibitor herbicides include, but are not limited to, amitorol, cromazon, fluridone, isoxaflutol, mesotrione, norflurazone, pyrasulfolol, tenbotrione, and topramezone.
[0066] Cellulose inhibitor herbicides selectively inhibit cellulose synthesis. Examples of cellulose inhibitor herbicides include, but are not limited to, diclobenil, flupoxam, indadiflame, isoxaben, and quinchlorac.
[0067] EPSP herbicides are herbicides that inhibit 5-enorpyruvir shikimate-3-phosphate (EPSP) synthase, a key enzyme in the shikimic acid pathway involved in the synthesis of aromatic amino acids. EPSP inhibition leads to the depletion of tryptophan, tyrosine, and phenylalanine, aromatic amino acids necessary for protein synthesis. Glyphosate is the most widely used EPSP herbicide.
[0068] Glutamine synthesis inhibitor herbicides inhibit the activity of glutamine synthetase, an enzyme that converts glutamic acid and ammonia into glutamine. This inhibition leads to a large accumulation of ammonia in plants, which destroys cells and directly inhibits photosystem I and photosystem II reactions. Glufosinate is the most widely used glutamine synthesis inhibitor herbicide.
[0069] Lipid synthesis inhibitory herbicides interfere with the biosynthesis of fatty acids and lipids in plants. Examples of lipid synthesis inhibitory herbicides include, but are not limited to, acetochlor, alachlor, benslide, benthiocarb, chloroacetamide, cycloate, dimethenamide, S-ethyl-N,N-dipropylthiocarbamate (EPTC), etofmesate, flufenacet, metrachlor, napropamide, propachlor, and trialate.
[0070] Microtubule-association inhibitor herbicides are mitotic toxins that inhibit cell division in plants. Examples of microtubule-association inhibitors include, but are not limited to, benefin, benfluralin, dimethyltetrachloroterephthalate (DCPA), dithiopyr, ethalfluralin, oryzarin, pendimethalin, prodiamine, propizamide (pronamide), thiazopyr, and trifluralin.
[0071] Photochemical inhibitor herbicides are compounds that interfere with photosynthesis and cellular respiration processes to kill plants. Examples of photochemical inhibitor herbicides include, but are not limited to, atrazine, diquat, diuron, linulone, metrivudine, paraquat, and simazine.
[0072] Herbicides can also be classified by chemical class. Herbicides that can reduce phytotoxic side effects on crop plants using ascalosides include, for example, carbamates, thiocarbamates, haloacetanilide, quinolyloxy, quinoxalyloxy, pyridyloxy, benzoxazolyloxy, and benzothiazolyloxyphenoxyalkane carboxylic acid esters, as well as substituted phenoxy, naphthoxy, and phenoxyphenoxycarboxylic acid derivatives and heteroaryloxyphenoxyalkane carboxylic 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), such as bentazone, cyanazine, atrazine, bromoxynil, dicamba, and other foliar herbicides. Other compounds for use in the present invention, such as the herbicide benzoyl isoxazole and / or dione compounds, which are not commercially available, may be prepared by the methods described in the patent publication or by the application or adaptation of known methods used or described in the chemical literature for similar compounds.
[0073] It is recognized that additional herbicides and other plant growth regulators may be included in the methods and compositions of the present invention. Other additional activators that can be used with the combinations described herein include fungicides, insecticides, acaricides, arthropod agents, fungicides, ectoparasite eradicators, etc., which are known in the art, are compatible with the combinations of the present invention, and do not antagonize the activity of ascaloside(s) or herbicides(s).
[0074] 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 salts and derivatives such as esters, even if a specific salt or ester is not specifically mentioned (its usual commercial form is preferred).
[0075] The application of one or more herbicides and one or more ascalosides may be before or after germination. The preferred application method depends on the usual or optimal application time for the specific herbicide or combination of herbicides.
[0076] The antipathogenic activity of ascalosides provides additional benefits to methods and compositions. Advantageously, one or more ascalosides can not only provide a reduction in the phytotoxic effects on plants commonly associated with herbicide application, but can also provide long-lasting fungicidal effects. For example, while fungicidal and antimicrobial agents are generally applied at later stages of crop growth when such pathogens are present, this disclosure provides methods and compositions that employ the application of ascalosides at a very early stage (i.e., when herbicides are traditionally applied to crops) and can confer resistance to pathogens in crop plants thus treated. In some embodiments, ascalosides are applied at an early stage of the plant life cycle, but surprisingly, they exhibit long-lasting effects of reducing or preventing damage caused by fungi, bacteria, viruses, and molds for periods exceeding, for example, 3 days, 5 days, 1 week, 2 weeks, 1 month, 2 months, or 3 months after application.
[0077] Simultaneous application of ascaloside and herbicides early in the season offers significant economic benefits to growers and enhances the sustainability of crop production. Simultaneous application of ascaloside with herbicides can prevent the need for separate fungicide treatments later in the season. Ascaloside treatment can function as a preventative measure, enhancing crop resistance to a wide range of pathogens, thus saving fuel and labor and potentially avoiding the need to apply more toxic pathogen control products. An additional or alternative benefit of combining ascaloside with herbicide treatment is the control of early-season plant pathogens such as fungi, bacteria, viruses, and nematodes. While not bound by specific theories, simultaneous application of herbicides and ascaloside saves fuel and labor, and ascaloside treatment can function as a preventative measure, enhancing crop resistance to a wide range of pathogens, thus potentially avoiding the need to apply more toxic pathogen control products and preventing the need for separate early-season fungicides.
[0078] In certain embodiments, the disclosure provides a blend of one or more herbicides and one or more ascalosides, characterized in that the blended product reduces the phytotoxic effects 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.
[0079] In some embodiments, the blend is characterized by a reduction of one or more phytotoxic symptoms in the treated crop by 10-90%, 10-70%, 10-50%, 10-30%, 30-90%, 50-90%, 70-90%, 30-70%, or 30-50% compared to the use of an equivalent composition lacking ascalosides.
[0080] In some embodiments, plant toxicity symptoms are measured by a plant toxicity assessment, for example, as described in Example 2 herein. In some embodiments, the blend is characterized in that the plant toxicity assessment (e.g., as described in Example 2 herein) in the treated crop is 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 the plant toxicity assessment (e.g., as described in Example 2 herein) is 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 some embodiments, the blend is characterized by a reduction in the phytotoxicity assessment of the treated crop (e.g., as described in Example 2 of this specification) by 10-90%, 10-70%, 10-50%, 10-30%, 30-90%, 50-90%, 70-90%, 30-70%, or 30-50% compared to the use of an equivalent composition lacking ascalosides.
[0081] In certain embodiments, the phytotoxic effects that can be reduced by the use of ascaloside 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 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.
[0082] The compounds described herein may be provided as a single formulation or agricultural composition, or as separate formulations or agricultural compositions. In addition, the components may be applied separately. When one or more ascalosides and one or more herbicides are applied separately, one or more ascalosides may be applied before or after the application of one or more herbicides. Generally, when applied separately, the components may be applied substantially simultaneously or within a few minutes or hours, including within a short timeframe, for example, within about 5 minutes, 10 minutes, 30 minutes, 1 hour, 2 hours, 3 hours, 4 hours, 6 hours, 7 hours, 8 hours, 24 hours, or 2 days.
[0083] Simultaneous application, in some embodiments, may include combining one or more ascalosides with one or more herbicides before application to plants (e.g., immediately before application). One or more ascalosides and one or more herbicides may be mixed in the field; for example, one or more ascalosides can be added to a fully formulated tank mixture containing one or more herbicides.
[0084] 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 comprising one or more ascalosides and one or more herbicides in combination with one or more inactive components. Advantageously, in such combinations, one or more ascalosides and one or more herbicides are compatible with each other, and the resulting formulation can exhibit stability over a long period (e.g., about one week or more, about one month or more, about two months or more, about three months or more, about four months or more, about five months or more, or about six months or more).
[0085] One or more ascalosides and one or more herbicides can be formulated together in combination formulations. As described above, formulations or methods may include other active ingredients and / or plant or plant product treatment compounds. Furthermore, some of the compositions may be residual in that they are not easily washed away from the leaves during rain, and thus can protect plants during and after rainfall.
[0086] In certain embodiments, the Disclosure provides a blend of one or more herbicides and one or more 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.
[0087] The formulation or composition may be formulated in the conventional manner in the art and may be a liquid or a dry composition. Dry compositions include powders, etc. The composition may be available as a liquid concentrate, a ready-to-use (RTU) liquid spray, a dust, or a solid, depending on the user's needs. The selected formulation depends on the use of the product. During use, the composition may be applied directly to plants.
[0088] Generally, formulations comprise at least one ascaloside described herein, or at least one ascaloside and one or more herbicides, and one or more agriculturally acceptable adjuvants (also referred to herein as “agriculturally suitable adjuvants”). Agriculturally suitable adjuvants are used to enhance the efficacy of the compounds described herein and include, but are not limited to, surfactants, emulsifiers, oils, salts, etc. Adjuvants may be added to formulations or, alternatively, added separately when applied to crops. In some embodiments, wetting agents, emulsifiers, spreading agents, etc., may be used in formulations. Formulations include concentrated forms in which the active ingredient (compound described herein) is present at a concentration of 0.001 to 98.0 percent, with the remaining contents being a physiologically acceptable carrier. Such formulations, in particular formulations having less than 50 percent of the compound, may sometimes be used directly, but these formulations may also be diluted with other physiologically acceptable carriers to form more diluted treatment formulations. These latter formulations may contain the compounds described herein at lower concentrations of 0.001 to 0.1 percent.
[0089] 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, phosphate alcohol ethoxylates, natural primary alcohols (C12-Ci6) 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. The formulation may also include oil-in-water emulsions.
[0090] Surfactants typically make up about 0.5% to 10% of wettable powders. Surfactants include nonionic surfactants or mixtures thereof, such as sulfonated lignin, condensed naphthalene sulfonates, naphthalene sulfonates, alkyl benenesulfonates, alkyl sulfonates, or ethylene oxide adducts of alkylphenols.
[0091] Typical organic solvents that may be used in preparing emulsifying concentrates of ascalosides (plural) and / or herbicides (plural) of the present disclosure include: xylene, aromatic fractions such as propylbenzene fraction; or mixed naphthalene fractions, mineral oils, 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 fractions or mineral oils, 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, 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, tung oil, etc.; esters of the above-mentioned vegetable oils. A mixture of two or more organic liquids may also be used in the preparation of emulsifying concentrates. Examples of organic liquids include xylene and propylbenzene fractions, with xylene being most preferred in some cases. Surface dispersants are typically used in liquid formulations in amounts of 0.1 to 20 percent by weight, based on the combined weight of the dispersant with one or more of the compounds.
[0092] The “emulsifiers” for emulsifiable concentrates are typically mixed ionic and / or nonionic surfactants or their equivalents, such as those described herein. Examples of nonionic emulsifiers useful for preparing emulsifiable concentrates include polyalkylene glycol ethers, as well as ethoxylated alkylphenols and carboxylic acid esters solubilized with alkylphenols and arylphenols, aliphatic alcohols, aliphatic amines or fatty acids and condensation products of ethylene oxide, propylene oxide, e.g., 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.
[0093] Dust containing ascalosides and / or herbicides may 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 compounds, based on the total weight of the dust.
[0094] 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" typically include prophyllite, 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.
[0095] An aqueous suspension can be prepared when one or more ascalosides and / or one or more herbicides are dispersed in an aqueous vehicle at concentrations typically ranging from about 5% to about 50% by weight. The suspension is prepared by finely grinding the compounds and vigorously mixing them 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.
[0096] As described herein, the compositions and methods of the present invention are useful for reducing the phytotoxic effects of herbicides on treated crops. The method involves applying an effective amount of a combination of ascaloside composition and herbicide composition to seeds, plants, plant leaves, or the soil in which the plants grow.
[0097] 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. In this application, unless otherwise clearly stated in the context, the term “one (a)” may be understood to mean “at least one.”
[0098] As used in this application, the term “or” may be understood to mean “and / or.” In this application, the terms “comprising” and “including” may be understood to encompass the itemized component or step, whether indicated by itself or with one or more additional components or steps. As used 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.
[0099] Approximately, roughly: Where used herein, the terms “approximately” and “roughly” are used interchangeably. Unless otherwise specified, the terms “approximately” and “roughly” can 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 number used in this application, with or without “approximately,” is intended to cover any normal variation as understood by those skilled in the art. In some embodiments, the terms “roughly” or “approximately” 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).
[0100] The definitions of specific functional groups and chemical terms are described in more detail below. For the purposes of this invention, chemical elements are identified according to the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75th Ed., inside cover, and 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; Smith and March March's Advanced Organic Chemistry, 5th Edition, John Wiley & Sons, Inc., New York, 2001; Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989; and Carruthers, Some Modern Methods of Organic Synthesis, 3rd Edition, Cambridge University Press, Cambridge, 1987, the entire contents of each of these are incorporated herein by reference.
[0101] 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.
[0102] 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.
[0103] 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.”
[0104] 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).
[0105] 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 (iod, -I).
[0106] 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.
[0107] 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.
[0108] As used herein, the term “unsaturated” means that a part has one or more double or triple bonds.
[0109] 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.
[0110] 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.
[0111] The term “aryl,” used alone or as part of a larger term, 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 anthrasyl, which may have one or more substituents. The scope of the term “aryl” as used herein also includes groups into which the aromatic ring is condensed with one or more additional rings, such as benzofuranyl, indanyl, phthalimidyl, naphthoimidyl, phenantridinyl, or tetrahydronaphthyl.
[0112] 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 pelectrons within a 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).
[0113] 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).
[0114] 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.
[0115] 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.
[0116] As described herein, the compounds provided herein may contain “optionally substituted” moieties. Generally, the term “substituted” means that one or more hydrogens of a designated moiety are replaced with preferred substituents, whether or not the term “optionally” precedes it. Unless otherwise indicated, an “optionally substituted” group may have preferred substituents at each substituted position of the group, and if more than one position in any given structure can be replaced with more than one substituent selected from a particular group, the substituents may be the same at all positions or different at all positions. The assumed substituent combinations preferably result in the formation of a stable or chemically feasible compound. The term “stable,” as used herein, means a compound that remains substantially unchanged when placed under conditions that enable their production, detection, and, in certain embodiments, their recovery, purification, and use in one or more of the purposes disclosed herein.
[0117] Suitable monovalent substituents on the replaceable carbon atoms of the "optionally substituted" group are, independently, halogens, -(CH2) 0-4 R°, -(CH2) 0-4 OR°, -O-(CH2) 0-4 C(O)OR°, -(CH2) 0-4 CH(OR°)2, -(CH2) 0-4 -(CH2) can be substituted with SR° and R°. 0-4 (CH2) can be substituted with pH and R°. 0-4 O(CH2) 0-1 -CH=CHPh, -NO2, -CN, -N3, -(CH2) can be substituted with Ph and R°. 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.
[0118] The intervening atoms along with the preferred monovalent substituents of R° 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 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.
[0119] Suitable divalent substituents on the saturated carbon atom of the "optionally substituted" group are, =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- was mentioned, R * Each independent occurrence of C can be substituted with hydrogen, as defined below. 1-6 Selected from an aliphatic, or unsubstituted 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. A suitable divalent substituent to bond to the substituted carbon proximal to the "optionally substituted" group is -O(CR * 2) 2-3 O- is mentioned, R * Each independent occurrence of C can be substituted with hydrogen, as defined below. 1-6 Selected from aliphatic, or unsubstituted 5-6 member saturated, partially unsaturated, or aryl rings having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.
[0120] R * Suitable substituents on the aliphatic group include halogens, -R ● ,-(HaroR ● ), -OH, -OR ● ,-O(HaroR ● ), -CN, -C(O)OH, -C(O)OR ● -NH2, -NHR ● , -NR ● 2, or -NO2 is included, 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 It is a 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from pH, nitrogen, oxygen, or sulfur.
[0121] A suitable substituent on the substituted nitrogen of the "optionally substituted" group is -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 † These are listed, and each R † C can be substituted independently of hydrogen, as defined below. 1-6 Aliphatic, unsubstituted-OPh, or unsubstituted 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, R † The two independent occurrences, together with their intervening atom(s), form an unsubstituted 3-12 member saturated, partially unsaturated, or aryl monocyclic or bicyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.
[0122] R † Suitable substituents on the aliphatic group are, independently, halogens, -R ● ,-(HaroR ● ), -OH, -OR ● ,-O(HaroR ● ), -CN, -C(O)OH, -C(O)OR ● -NH2, -NHR ● , -NR ● 2, or -NO2, and each R ● If it is unsubstituted, or if preceded by "halo", it is substituted by only one or more halogens, independently, C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1It is a 5-6 member saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from pH, nitrogen, oxygen, or sulfur.
[0123] 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.
[0124] 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 smid-db.org on the World Wide Web.
[0125] Embodiments of the present invention include the following: 1. A method for reducing phytotoxic side effects to plants during the application of a herbicide, the method comprising contacting a plant or plant part with an effective amount of a combination of agents, wherein the agents comprise at least one ascaloside and at least one herbicide, and the effective amount of ascaloside reduces phytotoxic side effects to crop plants during the application of the herbicide. 2. The method according to Embodiment 1, wherein the herbicide is a PPO herbicide, an auxin herbicide, an ALS / AHAS herbicide, an ACCase inhibitor herbicide, a carotenoid biosynthesis inhibitor herbicide, a cellulose inhibitor herbicide, an EPSP inhibitor herbicide, a glutamine synthesis inhibitor herbicide, a lipid synthesis inhibitor herbicide, a microtubule association inhibitor herbicide, or a photosystem inhibitor herbicide. 3. The herbicide is a carbamate; thiocarbamate; haloacetanilide; substituted phenoxy-, naphthoxy-, and phenoxyphenoxycarboxylic acid derivatives; heteroaryloxyphenoxyalkanecarboxylic acid derivatives; quinolyloxy-, quinoxalyloxy-, pyridyloxy-, benzoxazolyloxy-, and benzothiazolyloxyphenoxyalkanecarboxylic acid esters; cyclohexanedione derivatives; imidazolinone; pyrimidinyloxypyridinecarboxylic acid derivatives; pyrimidinyloxy The method according to Embodiment 1, selected from the group consisting of fuciates derivatives; sulfonylurea; triazolopyrimidine sulfonamide derivatives; S-(N-aryl-N-alkylcarbamoylmethyl)dithiophosphate esters; hormone-type herbicides; pyridinecarboxylic acid; triazinones; triazolinones; pyridinecarboxamides; hydroxybenzonitriles; isoxazoles; phenoxyphenoxy and heteroaryloxyphenoxycarboxylic acid esters and salts, sulfonylurea, imidazolinone; and isoxazoles. 4. The method according to Embodiment 1, wherein the at least one herbicide is a PPO herbicide. 5. The method according to Embodiment 4, wherein the PPO herbicide is acronifen, acifluorfen, bifenox, butafenacil, flumioxazine, fomesafen, oxyfluorfen, oxadiazone, saflufenacil, or sulfenthrazone. 6. The method according to Embodiment 1, wherein the at least one herbicide is an auxin herbicide. 7. The method according to Embodiment 6, wherein the auxin herbicide is aminopyralide, aminocyclopyral, 4-(4-chloro-o-tolyloxy)butyric acid (MCPB), clopyralide, dicamba, diflufenzopyr, 2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), fluroxypyr, mecoprop, 2-methyl-4-chlorophenoxyacetic acid (MCPA), picrolam, quinchlorac, 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), or triclopyr. 8. The method according to Embodiment 1, wherein the at least one herbicide is an ALS / AHAS herbicide. 9. The method according to Embodiment 8, wherein the ALS / AHAS herbicide is bensulfuron, chlorimuron, chloransulam, chlorsulfuron, diclosulam, florasulam, flucarbazone, flumetulam, foramsulfuron, halosulfuron, imazametabenz, imazamox, imazapick, imazapyr, imazakine, imazetapir, mesosulfuron, metosulfuron, nicosulfuron, penoxulam, primisulfuron, propoxycarbazone, prosulfuron, pyrithiobac, piroxulam, limsulfuron, sulfomethuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenulon, trifloxysulfuron, or triflusulfuron. 10. The method according to Embodiment 1, wherein the at least one herbicide is an ACCase inhibitor herbicide. 11. The method according to Embodiment 10, wherein the ACCase inhibitor herbicide is butroxidime, cretodime, cyhalofop, diclofop, phenoxaprop, fluazifop, haloxyfop, pinoxadene, quizalofop, cethoxydime, or tralcoxidime. 12. The method according to Embodiment 1, wherein the at least one herbicide is a carotenoid biosynthesis inhibitor herbicide. 13. The method according to Embodiment 12, wherein the carotenoid biosynthesis inhibitor herbicide is amitrol, chromazon, fluridone, isoxaflutol, mesotrione, norflurazone, pyrasulfolol, tenbotrione, or topramezone. 14. The method according to Embodiment 1, wherein the at least one herbicide is a cellulose inhibitor herbicide. 15. The method according to Embodiment 14, wherein the cellulose inhibitor herbicide is diclobenil, flupoxam, indadiflame, isoxaben, and quinchlorac. 16. The method according to Embodiment 1, wherein the at least one herbicide is glyphosate. 17. The method according to Embodiment 1, wherein the at least one herbicide is glufosinate. 18. The method according to Embodiment 1, wherein the at least one herbicide is a lipid synthesis inhibitor herbicide. 19. The method according to Embodiment 18, wherein the lipid synthesis inhibitory herbicide is acetochlor, alachlor, benslide, benthiocarb, chloroacetamide, cycloate, dimethenamide, S-ethyl-N,N-dipropylthiocarbamate (EPTC), etofmesate, flufenacet, metrachlor, napropamide, propachlor, or triarate. 20. The method according to Embodiment 1, wherein the at least one herbicide is a microtubule association inhibitor herbicide. 21. The method according to Embodiment 20, wherein the microtubule association inhibitor herbicide is benefin, benfluralin, dimethyltetrachloroterephthalate (DCPA), dithiopyr, ethalfluralin, oryzarin, pendimethalin, prodiamine, propizamide (pronamide), thiazopyr, or trifluralin. 22. The method according to Embodiment 1, wherein the at least one herbicide is a photochemical inhibitor herbicide. 23. The method according to Embodiment 22, wherein the photochemical inhibitor herbicide is atrazine, diquat, diuron, linuron, metrivudine, paraquat, or simazine. 24. The at least one askaloside comprises an askaloside having structure (I), [ka] During the ceremony, Z is replaced by C of any choice. 3-40 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 2-20Carbamates (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, 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 The method according to any one of Embodiments 1 to 23, wherein together they can form an optionally substituted ring that optionally contains one or more heteroatoms and optionally contains one or more unsaturated sites. 25.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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), iii.-CH(CH3)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), iv.-CH(CH3)-(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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), v.-CH(CH3)-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), vi.-(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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), vii.-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), 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 C 1-20 (Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides), and ix.-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 The method according to Embodiment 24, selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 26.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 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), (xvi)-(CH2) n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3These 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 (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 The method according to Embodiment 24, selected from the group consisting of a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or linkage to another askaloside molecule via a carbon-containing linker moiety. 27.R a and R b The method according to any one of embodiments 24 to 26, wherein each is -H. 28. Z is -CH(CH3)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 However, C is substituted with -H, a metal cation, or optionally. 1-20 The method according to any one of Embodiments 24 to 27, wherein the group is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 29. The method according to any one of Embodiments 1 to 28, wherein the at least one ascaloside comprises an ascaloside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. 30. The method according to any one of Embodiments 1 to 29, wherein the at least one ascaloside comprises ascr#18. 31. The method according to any one of Embodiments 1 to 30, wherein the at least one ascaloside and the at least one herbicide are applied simultaneously. 32. The method according to Embodiment 31, wherein the at least one ascaloside and the at least one herbicide are combined together in a tank mixture. 33. The method according to any one of Embodiments 1 to 30, wherein the at least one ascaloside and the at least one herbicide are applied in succession. 34. The method according to any one of Embodiments 1 to 33, wherein the combination is used as a seed coating. 35. A composition comprising at least one ascaloside and at least one herbicide. 36. The composition according to Embodiment 35, wherein at least one ascaloside and at least one herbicide are present in an effective amount. 37. The composition according to Embodiment 35, wherein the herbicide is a PPO herbicide, an auxin herbicide, an ALS / AHAS herbicide, an ACCase inhibitor herbicide, a carotenoid biosynthesis inhibitor herbicide, a cellulose inhibitor herbicide, an EPSP inhibitor herbicide, a glutamine synthesis inhibitor herbicide, a lipid synthesis inhibitor herbicide, a microtubule association inhibitor herbicide, or a photosystem inhibitor herbicide. 38. The herbicide is a carbamate; thiocarbamate; haloacetanilide; substituted phenoxy-, naphthoxy-, and phenoxyphenoxycarboxylic acid derivatives; heteroaryloxyphenoxyalkanecarboxylic acid derivatives; quinolyloxy-, quinoxalyloxy-, pyridyloxy-, benzoxazolyloxy-, and benzothiazolyloxyphenoxyalkanecarboxylic acid esters; cyclohexanedione derivatives; imidazolinone; pyrimidinyloxypyridinecarboxylic acid derivatives; pyrimidinyloxybenzo A composition according to Embodiment 35, selected from the group consisting of fragrant acid derivatives; sulfonylurea; triazolopyrimidine sulfonamide derivatives; S-(N-aryl-N-alkylcarbamoylmethyl)dithiophosphate esters; hormone-type herbicides; pyridinecarboxylic acid; triazinones; triazolinones; pyridinecarboxamides; hydroxybenzonitriles; isoxazoles; phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts, sulfonylurea, imidazolinone; and isoxazoles. 39. The composition according to Embodiment 35, wherein the at least one herbicide is a PPO herbicide. 40. The composition according to Embodiment 39, wherein the PPO herbicide is acronifen, acifluorphen, bifenox, butafenacil, flumioxazine, homeafen, oxyfluorphen, oxadiazone, saflufenacil, or sulfenthrazone. 41. The composition according to Embodiment 35, wherein the at least one herbicide is an auxin herbicide. 42. The composition according to Embodiment 41, wherein the auxin herbicide is aminopyralide, aminocyclopyral, 4-(4-chloro-o-tolyloxy)butyric acid (MCPB), clopyralide, dicamba, diflufenzopyr, 2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), fluroxypyr, mecoprop, 2-methyl-4-chlorophenoxyacetic acid (MCPA), picrolam, quinchlorac, 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), or triclopyr. 43. The composition according to Embodiment 35, wherein the at least one herbicide is an ALS / AHAS herbicide. 44. The composition according to Embodiment 43, wherein the ALS / AHAS herbicide is bensulfuron, chlorimuron, chloransulam, chlorsulfuron, diclosulam, florasulam, flucarbazone, flumetulam, foramsulfuron, halosulfuron, imazametabenz, imazamox, imazapick, imazapyr, imazakine, imazetapir, mesosulfuron, metosulfuron, nicosulfuron, penoxulam, primisulfuron, propoxycarbazone, prosulfuron, pyrithiobac, piroxulam, limsulfuron, sulfomethuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenulon, trifloxysulfuron, or triflusulfuron. 45. The composition according to Embodiment 35, wherein the at least one herbicide is an ACCase inhibitor herbicide. 46. The composition according to Embodiment 45, wherein the ACCase inhibitor herbicide is butroxidime, cretodime, cyhalofop, diclofop, phenoxaprop, fluazifop, haloxyfop, pinoxadene, quizalofop, cethoxydime, or tralcoxidime. 47. The composition according to Embodiment 35, wherein the at least one herbicide is a carotenoid biosynthesis inhibitor herbicide. 48. The composition according to Embodiment 47, wherein the carotenoid biosynthesis inhibitor herbicide is amitrol, chromazon, fluridone, isoxaflutol, mesotrione, norflurazone, pyrasulfolol, tenbotrione, or topramezone. 49. The composition according to Embodiment 35, wherein the at least one herbicide is a cellulose inhibitor herbicide. 50. The composition according to Embodiment 49, wherein the cellulose inhibitor herbicide is diclobenil, flupoxam, indadiflame, isoxaben, and quinchlorac. 51. The composition according to Embodiment 35, wherein the at least one herbicide is glyphosate. 52. The composition according to Embodiment 35, wherein the at least one herbicide is glufosinate. 53. The composition according to Embodiment 35, wherein at least one of the herbicides is a lipid synthesis inhibitor herbicide. 54. The composition according to Embodiment 53, wherein the lipid synthesis inhibitory herbicide is acetochlor, alachlor, benslide, benthiocarb, chloroacetamide, cycloate, dimethenamide, S-ethyl-N,N-dipropylthiocarbamate (EPTC), etofmesate, flufenacet, metrachlor, napropamide, propachlor, or triarate. 55. The composition according to Embodiment 35, wherein the at least one herbicide is a microtubule association inhibitor herbicide. 56. The composition according to Embodiment 55, wherein the microtubule association inhibitor herbicide is benefin, benfluralin, dimethyltetrachloroterephthalate (DCPA), dithiopyr, ethalfluralin, oryzarin, pendimethalin, prodiamine, propizamide (pronamide), thiazopyr, or trifluralin. 57. The composition according to Embodiment 35, wherein the at least one herbicide is a photochemical inhibitor herbicide. 58. The composition according to Embodiment 57, wherein the photochemical inhibitor herbicide is atrazine, diquat, diuron, linuron, metrivudine, paraquat, or simazine. 59. The at least one askaloside comprises an askaloside having structure (I), [ka] During the ceremony, Z is replaced by C of any choice. 3-40 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 2-20Carbonate (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, 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 The composition according to any one of embodiments 35 to 58, wherein together they can form an optionally substituted ring that optionally contains one or more heteroatoms and optionally contains one or more unsaturated sites. 60.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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), iii.-CH(CH3)-(CH2) n-CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), iv.-CH(CH3)-(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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), v.-CH(CH3)-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), vi.-(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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), vii.-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), 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 C 1-20(Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides), and ix.-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 The composition according to Embodiment 59, selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 61.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 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), (xvi)-(CH2) n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3These 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 (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 The composition according to Embodiment 47, which is 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 linkage to another askaloside molecule via a carbon-containing linker moiety. 62.R a and R b The composition according to embodiment 60 or 61, wherein each of the elements is -H. 63.Z is -CH(CH3)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 However, C is substituted with -H, a metal cation, or optionally. 1-20 A composition according to any one of Embodiments 59 to 62, comprising an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 64. The composition according to any one of embodiments 35 to 63, wherein the at least one ascaloside comprises an ascaloside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. 65. The composition according to any one of embodiments 35 to 63, wherein the at least one ascaloside comprises ascr#18. 66. The composition according to any one of embodiments 35 to 65, wherein the composition is part of the tank mixture. 67. The composition according to any one of embodiments 35 to 65, wherein the composition is in solid form. 68. The composition according to Embodiment 67, wherein the solid form comprises powder or granules. 69. The composition according to any one of embodiments 35 to 65, wherein the composition is in liquid form. 70. The composition according to Embodiment 69, wherein the liquid form is a sprayable formulation. 71. The composition according to any one of Embodiments 35 to 70, wherein the composition is stable for a period of more than six months. 72. The composition according to any one of embodiments 35 to 71, wherein the composition further comprises 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, fillers / tackeners, tackifiers, plant penetration agents, toxicity mitigators, spreading agents, and wetting agents.
[0126] Embodiments of the present invention include the following: 1. A method for reducing phytotoxic side effects to plants associated with the application of herbicides, wherein the method comprises contacting a plant or plant part with an effective amount of a combination of agents, the agents comprising at least one ascaloside and at least one herbicide, and the effective amount reduces phytotoxic side effects to crop plants compared to phytotoxic side effects to plants associated with the application of the herbicide alone. 2. The method according to Embodiment 1, wherein the herbicide is a PPO herbicide, an auxin herbicide, an ALS / AHAS herbicide, an ACCase inhibitor herbicide, a carotenoid biosynthesis inhibitor herbicide, a cellulose inhibitor herbicide, an EPSP inhibitor herbicide, a glutamine synthesis inhibitor herbicide, a lipid synthesis inhibitor herbicide, a microtubule association inhibitor herbicide, or a photosystem inhibitor herbicide. 3. The herbicide is a carbamate; thiocarbamate; haloacetanilide; substituted phenoxy-, naphthoxy-, and phenoxyphenoxycarboxylic acid derivatives; heteroaryloxyphenoxyalkanecarboxylic acid derivatives; quinolyloxy-, quinoxalyloxy-, pyridyloxy-, benzoxazolyloxy-, and benzothiazolyloxyphenoxyalkanecarboxylic acid esters; cyclohexanedione derivatives; imidazolinone; pyrimidinyloxypyridinecarboxylic acid derivatives; pyrimidinyloxy The method according to Embodiment 1, selected from the group consisting of fuciates derivatives; sulfonylurea; triazolopyrimidine sulfonamide derivatives; S-(N-aryl-N-alkylcarbamoylmethyl)dithiophosphate esters; hormone-type herbicides; pyridinecarboxylic acid; triazinones; triazolinones; pyridinecarboxamides; hydroxybenzonitriles; isoxazoles; phenoxyphenoxy and heteroaryloxyphenoxycarboxylic acid esters and salts, sulfonylurea, imidazolinone; and isoxazoles. 4. The method according to Embodiment 1, wherein the at least one herbicide is a PPO herbicide. 5. The method according to Embodiment 4, wherein the PPO herbicide is acronifen, acifluorfen, bifenox, butafenacil, flumioxazine, fomesafen, oxyfluorfen, oxadiazone, saflufenacil, or sulfenthrazone. 6. The method according to Embodiment 1, wherein the at least one herbicide is an auxin herbicide. 7. The method according to Embodiment 6, wherein the auxin herbicide is aminopyralide, aminocyclopyral, 4-(4-chloro-o-tolyloxy)butyric acid (MCPB), clopyralide, dicamba, diflufenzopyr, 2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), fluroxypyr, mecoprop, 2-methyl-4-chlorophenoxyacetic acid (MCPA), picrolam, quinchlorac, 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), or triclopyr. 8. The method according to Embodiment 1, wherein the at least one herbicide is an ALS / AHAS herbicide. 9. The method according to Embodiment 8, wherein the ALS / AHAS herbicide is bensulfuron, chlorimuron, chloransulam, chlorsulfuron, diclosulam, florasulam, flucarbazone, flumetulam, foramsulfuron, halosulfuron, imazametabenz, imazamox, imazapick, imazapyr, imazakine, imazetapir, mesosulfuron, metosulfuron, nicosulfuron, penoxulam, primisulfuron, propoxycarbazone, prosulfuron, pyrithiobac, piroxulam, limsulfuron, sulfomethuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenulon, trifloxysulfuron, or triflusulfuron. 10. The method according to Embodiment 1, wherein the at least one herbicide is an ACCase inhibitor herbicide. 11. The method according to Embodiment 10, wherein the ACCase inhibitor herbicide is butroxidime, cretodime, cyhalofop, diclofop, phenoxaprop, fluazifop, haloxyfop, pinoxadene, quizalofop, cethoxydime, or tralcoxidime. 12. The method according to Embodiment 1, wherein the at least one herbicide is a carotenoid biosynthesis inhibitor herbicide. 13. The method according to Embodiment 12, wherein the carotenoid biosynthesis inhibitor herbicide is amitrol, chromazon, fluridone, isoxaflutol, mesotrione, norflurazone, pyrasulfolol, tenbotrione, or topramezone. 14. The method according to Embodiment 1, wherein the at least one herbicide is a cellulose inhibitor herbicide. 15. The method according to Embodiment 14, wherein the cellulose inhibitor herbicide is diclobenil, flupoxam, indadiflame, isoxaben, and quinchlorac. 16. The method according to Embodiment 1, wherein the at least one herbicide is glyphosate. 17. The method according to Embodiment 1, wherein the at least one herbicide is glufosinate. 18. The method according to Embodiment 1, wherein the at least one herbicide is a lipid synthesis inhibitor herbicide. 19. The method according to Embodiment 18, wherein the lipid synthesis inhibitory herbicide is acetochlor, alachlor, benslide, benthiocarb, chloroacetamide, cycloate, dimethenamide, S-ethyl-N,N-dipropylthiocarbamate (EPTC), etofmesate, flufenacet, metrachlor, napropamide, propachlor, or triarate. 20. The method according to Embodiment 1, wherein the at least one herbicide is a microtubule association inhibitor herbicide. 21. The method according to Embodiment 20, wherein the microtubule association inhibitor herbicide is benefin, benfluralin, dimethyltetrachloroterephthalate (DCPA), dithiopyr, ethalfluralin, oryzarin, pendimethalin, prodiamine, propizamide (pronamide), thiazopyr, or trifluralin. 22. The method according to Embodiment 1, wherein the at least one herbicide is a photochemical inhibitor herbicide. 23. The method according to Embodiment 22, wherein the photochemical inhibitor herbicide is atrazine, diquat, diuron, linuron, metrivudine, paraquat, or simazine. 24. The at least one askaloside comprises an askaloside having structure (I), [ka] During the ceremony, Z is replaced by C of any choice. 3-40 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 2-20Carbamates (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, 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 The method according to any one of Embodiments 1 to 23, wherein together they can form an optionally substituted ring that optionally contains one or more heteroatoms and optionally contains one or more unsaturated sites. 25.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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), iii.-CH(CH3)-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), iv.-CH(CH3)-(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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), v.-CH(CH3)-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), vi.-(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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), vii.-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), 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 C 1-20 (Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides), and ix.-(CH2) n -C(O)-CH2-CO2R 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 aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide), a method according to embodiment 24 selected from the group consisting of [[ID=⑨]] 26. Z is (x)-CH(CH3)-(CH2) 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(CH3)-(CH2) n -CH=CH-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), (xii)-CH(CH3)-(CH2) n -CH(OH)-CH2-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(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 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), (xvi)-(CH2) n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3These 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 The method according to Embodiment 24, selected from the group consisting of side chains. 27.R a and R b The method according to any one of embodiments 24 to 26, wherein each is -H. 28. Z is -CH(CH3)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 However, C is substituted with -H, a metal cation, or optionally. 1-20 The method according to any one of Embodiments 24 to 27, wherein the group is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 29. The method according to any one of Embodiments 1 to 28, wherein the at least one ascaloside comprises an ascaloside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. 30. The method according to any one of Embodiments 1 to 29, wherein the at least one ascaloside comprises ascr#18. 31. The method according to any one of Embodiments 1 to 30, wherein the at least one ascaloside and the at least one herbicide are applied simultaneously. 32. The method according to Embodiment 31, wherein the at least one ascaloside and the at least one herbicide are combined together in a tank mixture. 33. The method according to any one of Embodiments 1 to 30, wherein the at least one ascaloside and the at least one herbicide are applied in succession. 34. The method according to any one of Embodiments 1 to 33, wherein the combination is used as a seed coating. 35. A composition comprising at least one ascaloside and at least one herbicide. 36. The composition according to Embodiment 35, wherein at least one ascaloside and at least one herbicide are present in an effective amount. 37. The composition according to Embodiment 35, wherein the herbicide is a PPO herbicide, an auxin herbicide, an ALS / AHAS herbicide, an ACCase inhibitor herbicide, a carotenoid biosynthesis inhibitor herbicide, a cellulose inhibitor herbicide, an EPSP inhibitor herbicide, a glutamine synthesis inhibitor herbicide, a lipid synthesis inhibitor herbicide, a microtubule association inhibitor herbicide, or a photosystem inhibitor herbicide. 38. The herbicide is a carbamate; thiocarbamate; haloacetanilide; substituted phenoxy-, naphthoxy-, and phenoxyphenoxycarboxylic acid derivatives; heteroaryloxyphenoxyalkanecarboxylic acid derivatives; quinolyloxy-, quinoxalyloxy-, pyridyloxy-, benzoxazolyloxy-, and benzothiazolyloxyphenoxyalkanecarboxylic acid esters; cyclohexanedione derivatives; imidazolinone; pyrimidinyloxypyridinecarboxylic acid derivatives; pyrimidinyloxybenzo A composition according to Embodiment 35, selected from the group consisting of fragrant acid derivatives; sulfonylurea; triazolopyrimidine sulfonamide derivatives; S-(N-aryl-N-alkylcarbamoylmethyl)dithiophosphate esters; hormone-type herbicides; pyridinecarboxylic acid; triazinones; triazolinones; pyridinecarboxamides; hydroxybenzonitriles; isoxazoles; phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts, sulfonylurea, imidazolinone; and isoxazoles. 39. The composition according to Embodiment 35, wherein the at least one herbicide is a PPO herbicide. 40. The composition according to Embodiment 39, wherein the PPO herbicide is acronifen, acifluorphen, bifenox, butafenacil, flumioxazine, homeafen, oxyfluorphen, oxadiazone, saflufenacil, or sulfenthrazone. 41. The composition according to Embodiment 35, wherein the at least one herbicide is an auxin herbicide. 42. The composition according to Embodiment 41, wherein the auxin herbicide is aminopyralide, aminocyclopyral, 4-(4-chloro-o-tolyloxy)butyric acid (MCPB), clopyralide, dicamba, diflufenzopyr, 2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), fluroxypyr, mecoprop, 2-methyl-4-chlorophenoxyacetic acid (MCPA), picrolam, quinchlorac, 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), or triclopyr. 43. The composition according to Embodiment 35, wherein the at least one herbicide is an ALS / AHAS herbicide. 44. The composition according to Embodiment 43, wherein the ALS / AHAS herbicide is bensulfuron, chlorimuron, chloransulam, chlorsulfuron, diclosulam, florasulam, flucarbazone, flumetulam, foramsulfuron, halosulfuron, imazametabenz, imazamox, imazapick, imazapyr, imazakine, imazetapir, mesosulfuron, metosulfuron, nicosulfuron, penoxulam, primisulfuron, propoxycarbazone, prosulfuron, pyrithiobac, piroxulam, limsulfuron, sulfomethuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenulon, trifloxysulfuron, or triflusulfuron. 45. The composition according to Embodiment 35, wherein the at least one herbicide is an ACCase inhibitor herbicide. 46. The composition according to Embodiment 45, wherein the ACCase inhibitor herbicide is butroxidime, cretodime, cyhalofop, diclofop, phenoxaprop, fluazifop, haloxyfop, pinoxadene, quizalofop, cethoxydime, or tralcoxidime. 47. The composition according to Embodiment 35, wherein the at least one herbicide is a carotenoid biosynthesis inhibitor herbicide. 48. The composition according to Embodiment 47, wherein the carotenoid biosynthesis inhibitor herbicide is amitrol, chromazon, fluridone, isoxaflutol, mesotrione, norflurazone, pyrasulfolol, tenbotrione, or topramezone. 49. The composition according to Embodiment 35, wherein the at least one herbicide is a cellulose inhibitor herbicide. 50. The composition according to Embodiment 49, wherein the cellulose inhibitor herbicide is diclobenil, flupoxam, indadiflame, isoxaben, and quinchlorac. 51. The composition according to Embodiment 35, wherein the at least one herbicide is glyphosate. 52. The composition according to Embodiment 35, wherein the at least one herbicide is glufosinate. 53. The composition according to Embodiment 35, wherein at least one of the herbicides is a lipid synthesis inhibitor herbicide. 54. The composition according to Embodiment 53, wherein the lipid synthesis inhibitory herbicide is acetochlor, alachlor, benslide, benthiocarb, chloroacetamide, cycloate, dimethenamide, S-ethyl-N,N-dipropylthiocarbamate (EPTC), etofmesate, flufenacet, metrachlor, napropamide, propachlor, or triarate. 55. The composition according to Embodiment 35, wherein the at least one herbicide is a microtubule association inhibitor herbicide. 56. The composition according to Embodiment 55, wherein the microtubule association inhibitor herbicide is benefin, benfluralin, dimethyltetrachloroterephthalate (DCPA), dithiopyr, ethalfluralin, oryzarin, pendimethalin, prodiamine, propizamide (pronamide), thiazopyr, or trifluralin. 57. The composition according to Embodiment 35, wherein the at least one herbicide is a photochemical inhibitor herbicide. 58. The composition according to Embodiment 57, wherein the photochemical inhibitor herbicide is atrazine, diquat, diuron, linuron, metrivudine, paraquat, or simazine. 59. The at least one askaloside comprises an askaloside having structure (I), [ka] During the ceremony, Z is replaced by C of any choice. 3-40 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 2-20Carbonate (e.g., - moiety - C(O)OR c ), C 2-20 Carbamate (e.g., - moiety - C(O)N(R 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 )2), a sugar moiety, a peptide, a polymer chain, or a bond or linkage via a carbon - containing linker moiety to another ascarylose molecule, an optionally substituted moiety selected from the group consisting of: R c is, independently at each occurrence, - H, an optionally substituted C 1-12 aliphatic, an optionally substituted C 1-12 heteroaliphatic, an optionally substituted aryl, an optionally substituted heteroaryl, a polymer chain, or a bond or linkage via a carbon - containing linker moiety to another ascarylose molecule, R a and R b may together form an optionally substituted ring optionally containing one or more heteroatoms and optionally containing one or more sites of unsaturation, a composition according to any one of embodiments 35 - 58. 60. Z is i. - CH(CH3)-R 1 (R 1 is an optionally substituted C 1-40 aliphatic group), ii. - CH(CH3)-(CH2) n -CO2R[[ID=-CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), iv.-CH(CH3)-(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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), v.-CH(CH3)-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), vi.-(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 C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), vii.-(CH2) n -CH=CH-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 (Aliphatic group, optionally substituted aromatic group, glycoside, amino acid, peptide, or nucleotide), 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 C 1-20(Aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides), and ix.-(CH2) n -C(O)-CH2-CO2R 2 (n is an integer from 1 to 40, R 2 C is substituted with -H, a metal cation, or optionally substituted C 1-20 The composition according to Embodiment 59, selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 61.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 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), (xvi)-(CH2) n -CH(OH)-CH2-CON(R 3 )2(n is an integer from 1 to 40, and each R 3These 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 The side chain is the composition described in Embodiment 47. 62.R a and R b The composition according to embodiment 60 or 61, wherein each of the elements is -H. 63.Z is -CH(CH3)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 However, C is substituted with -H, a metal cation, or optionally. 1-20 A composition according to any one of Embodiments 59 to 62, comprising an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide. 64. The composition according to any one of embodiments 35 to 63, wherein the at least one ascaloside comprises an ascaloside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. 65. The composition according to any one of embodiments 35 to 63, wherein the at least one ascaloside comprises ascr#18. 66. The composition according to any one of embodiments 35 to 65, wherein the composition is part of the tank mixture. 67. The composition according to any one of embodiments 35 to 65, wherein the composition is in solid form. 68. The composition according to claim 67, wherein the solid form comprises powder or granules. 69. The composition according to any one of embodiments 35 to 65, wherein the composition is in liquid form. 70. The composition according to claim 69, wherein the liquid form is a sprayable formulation. 71. The composition according to any one of Embodiments 35 to 70, wherein the composition is stable for a period of more than six months. 72. The composition according to any one of embodiments 35 to 71, wherein the composition further comprises 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, fillers / tackeners, tackifiers, plant penetration agents, toxicity mitigators, spreading agents, and wetting agents. [Examples]
[0127] Example 1: Ascaloside tank mixing test with glyphosate in soybeans. A study was conducted to evaluate the post-emergence application of Phytalix in combination with Roundup PowerMax3® (a commercially available glyphosate formulation). The study was organized in a randomized, fully block design with four replications per treatment and a plot size of 10 feet × 30 feet. The study was replicated at three separate locations, and the tank mixture, prepared using 20 ounces / acre (0.91 lb AI / acre) of Roundup PowerMax3, ammonium sulfate (3.4 lb / acre), and 50 mg / acre of Phytalix® (a formulation containing ascaloside), was applied to the plots when soybean plants were in the V3–V4 growth stage and the target grasses and broadleaf weeds were approximately 3–6 inches tall.
[0128] Example 2: Tank mixing test of glufosinate and ascaloside in soybeans. A study was conducted to evaluate the post-emergence application of Phytalix in combination with Liberty® (a commercially available glufosinate formulation). The study was conducted in a randomized, fully block design with four replications per treatment and a plot size of 10 feet × 30 feet. The study was replicated at three separate locations. Tank mixture formulations were prepared by combining Liberty 32 fl oz / acre (0.58 lb ai / acre) with ammonium sulfate (3 lb / acre) and 50 mg / acre of ascaloside ascr#18. This mixture was applied to the plots when soybean plants were in the V3–V4 growth stage and the targeted grasses and broadleaf weeds were approximately 3–6 inches tall.
[0129] Both plots in Example 1 and 2 were evaluated as follows: Weed control in each plot was evaluated as a percentage of the control 7 and 14 days after application. Plant toxicity evaluations for each plot were also measured 7 and 14 days after application. After 14 days of evaluation, a full-scale herbicide application was carried out to keep test weeds free throughout the season to evaluate the harvest. When the soybean crop reached approximately R6-R7 growth stages, disease evaluations were collected. Disease evaluations included disease incidence % and severity. The plots were harvested separately, and the yield was measured and reported as bushels / acre. Weeds in the tested locations included Amaranthus retroflexus, Eleusine indica, Abutilon theophrasti, Broadleaf Signal Grass (Brachiaria platyphyla), Portulaca olera, Cardamine sp., Palmer Amaranth (Amaranthus palmerii), Common Barnyard Grass (Echinochloa crus-galli), Setaria faberi, and Tall Waterhemp (Amaranthus tuberculatus). Weed control and yield levels in all locations were not affected by the inclusion of ascaloside along with herbicide application in this study. No significant plant diseases or phytotoxicities were observed in any of the treatment groups in this study.
[0130] 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 can be carried out by those skilled in the art.
[0131] The use of headings in this disclosure will be understood to be provided for the convenience of the reader. The presence and / or placement of headings is not intended to limit the scope of the subject matter described herein. Unless otherwise specified, embodiments located in one section of this application are applicable throughout this application, both individually and in combination, to other embodiments.
[0132] Throughout this description, where a composition, compound, or product is described as having, containing, or comprising a particular component, or where a process and method is described as having, containing, or comprising a particular step, it is intended that there exist articles, devices, and systems of this application which are essentially composed of or comprise the listed components, and that there exist processes and methods of this application which are essentially composed of or comprise the listed processing steps.
[0133] Please understand that the order of steps or sequences for performing a particular action is not important, as long as the described method is functional. Furthermore, two or more steps or actions can be performed simultaneously.
[0134] All publications and patent applications described herein are indicators of the level of skill of those skilled in the art in the field relating to the present invention. 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 as being incorporated by reference.
[0135] While the aforementioned invention 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 attached claims.
Claims
1. A method for reducing phytotoxic side effects on plants associated with the application of herbicides, wherein the method comprises contacting a plant or plant part with an effective amount of a combination of agents, the agents comprising at least one ascaloside and at least one herbicide.
2. The method according to claim 1, wherein the effective amount reduces phytotoxic side effects on crop plants compared to phytotoxic side effects on plants associated with the application of the herbicide alone.
3. The method according to claim 1 or 2, wherein the effective amount reduces the plant toxicity assessment to crop plants compared to the plant toxicity assessment to plants associated with the application of the herbicide alone.
4. The method according to any one of claims 1 to 3, wherein the herbicide is a PPO herbicide, an auxin herbicide, an ALS / AHAS herbicide, an ACCase inhibitor herbicide, a carotenoid biosynthesis inhibitor herbicide, a cellulose inhibitor herbicide, an EPSP inhibitor herbicide, a glutamine synthesis inhibitor herbicide, a lipid synthesis inhibitor herbicide, a microtubule association inhibitor herbicide, or a photosystem inhibitor herbicide.
5. The herbicides include carbamates; thiocarbamates; haloacetanilides; substituted phenoxy, naphthoxy, and phenoxyphenoxycarboxylic acid derivatives; heteroaryloxyphenoxyalkane carboxylic acid derivatives; quinolyloxy, quinoxalyloxy, pyridyloxy, benzoxazolyloxy, and benzothiazolyloxyphenoxyalkane carboxylic acid esters; cyclohexanedione derivatives; imidazolinones; pyrimidinyloxypyridine carboxylic acid derivatives; and pyrimidyloxybenzoic acid derivatives. The method according to any one of claims 1 to 4, selected from the group consisting of: a compound; sulfonylurea; triazolopyrimidine sulfonamide derivatives; S-(N-aryl-N-alkylcarbamoylmethyl)dithiophosphate esters; hormone-type herbicides; pyridinecarboxylic acid; triazinones; triazolinones; pyridinecarboxamides; hydroxybenzonitrile; isoxazole; phenoxyphenoxy and heteroaryloxyphenoxycarboxylic acid esters and salts, sulfonylurea, imidazolinone; and isoxazole.
6. The method according to any one of claims 1 to 5, wherein the at least one herbicide is glyphosate.
7. The method according to any one of claims 1 to 5, wherein the at least one herbicide is glufosinate.
8. The at least one askaloside includes an askaloside having structure (I), 【Chemistry 19】 During the ceremony, Z is replaced by C of arbitrary choice. 3-40 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 ) 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 ) 2 ), a sugar moiety, a peptide, a polymer chain, or an optionally substituted moiety selected from the group consisting of a bond to another ascarylose molecule or a linkage via a carbon-containing linker moiety, where 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 7.
9. 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides), 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 The method according to claim 8, selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.
10. Z is (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 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). (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 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), or (xviiii) A optionally unsaturated and optionally substituted C chain ending containing a nitrogen-containing functional group, an oxygen-containing functional group, or a sulfur-containing functional group. 2-40 The method according to claim 8, selected from the group consisting of side chains.
11. The method according to any one of claims 1 to 10, wherein the at least one ascaloside comprises an ascaloside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24.
12. The method according to any one of claims 1 to 11, wherein the at least one ascaloside comprises ascr#18.
13. The method according to any one of claims 1 to 12, wherein the at least one ascaloside and the at least one herbicide are applied simultaneously.
14. The method according to claim 13, wherein the at least one ascaloside and the at least one herbicide are combined together in a tank mixture.
15. The method according to any one of claims 1 to 12, wherein the at least one ascaloside and the at least one herbicide are applied in succession.
16. The method according to any one of claims 1 to 15, wherein the combination is used as a seed coating.
17. A composition comprising at least one ascaloside and at least one herbicide.
18. The composition according to claim 17, wherein the at least one ascaloside and the at least one herbicide are present in an effective amount.
19. The composition according to claim 18, wherein the effective amount reduces phytotoxic side effects on crop plants compared to phytotoxic side effects on plants associated with the application of the herbicide alone.
20. The composition according to claim 17 or 18, wherein the effective amount reduces the plant toxicity assessment to crop plants compared to the plant toxicity assessment to plants associated with the application of the herbicide alone.
21. The composition according to any one of claims 17 to 20, wherein the herbicide is a PPO herbicide, an auxin herbicide, an ALS / AHAS herbicide, an ACCase inhibitor herbicide, a carotenoid biosynthesis inhibitor herbicide, a cellulose inhibitor herbicide, an EPSP inhibitor herbicide, a glutamine synthesis inhibitor herbicide, a lipid synthesis inhibitor herbicide, a microtubule association inhibitor herbicide, or a photosystem inhibitor herbicide.
22. The herbicides include carbamates; thiocarbamates; haloacetanilides; substituted phenoxy, naphthoxy, and phenoxyphenoxycarboxylic acid derivatives; heteroaryloxyphenoxyalkanecarboxylic acid derivatives; quinolyloxy, quinoxalyloxy, pyridyloxy, benzoxazolyloxy, and benzothiazolyloxyphenoxyalkanecarboxylic acid esters; cyclohexanedione derivatives; imidazolinones; pyrimidinyloxypyridinecarboxylic acid derivatives; pyrimidyloxybenzoic acid derivatives; A composition according to any one of claims 17 to 20, selected from the group consisting of sulfonylurea; triazolopyrimidine sulfonamide derivatives; S-(N-aryl-N-alkylcarbamoylmethyl)dithiophosphate esters; hormone-type herbicides; pyridinecarboxylic acid; triazinones; triazolinones; pyridinecarboxamides; hydroxybenzonitriles; isoxazoles; phenoxyphenoxy and heteroaryloxyphenoxycarboxylic acid esters and salts, sulfonylurea, imidazolinone; and isoxazole.
23. The composition according to any one of claims 17 to 20, wherein the at least one herbicide is glyphosate.
24. The composition according to any one of claims 17 to 20, wherein the at least one herbicide is glufosinate.
25. The at least one askaloside includes an askaloside having structure (I), 【Chemistry 20】 During the ceremony, Z is replaced by C of arbitrary choice. 3-40 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 that is optionally substituted from the group consisting of a sugar portion, a peptide, a polymer chain, or bonding to another ascaloside molecule or linking 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 17 to 24, wherein together they can form an optionally substituted ring containing optionally one or more heteroatoms and optionally one or more unsaturated moieties.
26. 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 aromatic group, glycoside, amino acid, peptide, or nucleotide) 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 groups, optionally substituted aromatic groups, glycosides, amino acids, peptides, or nucleotides), 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 The composition according to claim 25, selected from the group consisting of an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.
27. Z is (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 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), or (xviiii) A optionally unsaturated and optionally substituted C chain ending containing a nitrogen-containing functional group, an oxygen-containing functional group, or a sulfur-containing functional group. 2-40 The composition according to claim 25, wherein the side chain is...
28. The composition according to any one of claims 17 to 27, wherein the at least one ascaloside comprises an ascaloside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24.
29. The composition according to any one of claims 17 to 27, wherein the at least one ascaloside comprises ascr#18.
30. The composition according to any one of claims 17 to 29, wherein the composition is part of the tank mixture.
31. The composition according to any one of claims 17 to 29, wherein the composition is in solid form.
32. The composition according to claim 31, wherein the solid form includes powder or granules.
33. The composition according to any one of claims 17 to 29, wherein the composition is in liquid form.
34. The composition according to claim 33, wherein the liquid form is a sprayable formulation.
35. The composition according to any one of claims 17 to 34, wherein the composition is stable for a period of more than six months.
36. The composition according to any one of claims 17 to 35, wherein the composition further comprises 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.
