Stable herbicidal compositions

Abstract

Described herein are stable herbicidal compositions comprising: at least one cyclohexenedione oxime herbicide or an agriculturally acceptable salt thereof; and a stabilizer system comprising a dialkyl metal sulfosuccinate and a sorbitan fatty acid ester. Also disclosed are methods of making the stable herbicidal compositions and methods of controlling weeds by applying the stable herbicidal compositions to the weeds, crops, locus, or habitat area.

Description

TECHNICAL FIELD

[0001] The present disclosure relates to stable herbicidal compositions. The present disclosure more particularly relates to stable herbicidal compositions comprising a cyclohexenedione oxime herbicide and a stabilizer system. The present disclosure also relates to methods of making stable herbicidal compositions and methods of controlling weeds. BACKGROUND

[0002] Cyclohexanedione oxime herbicides (CHD) have been developed to be effective at relatively low doses and to be readily degradable to reduce the environmental impact of the herbicides. CHD herbicides have herbicidal activity on a variety of post-emergence grassy weeds. With respect to persistence in the environment, CHD herbicides are readily degraded by biological and abiotic processes. For example, these herbicides decompose at pH less than 5 and greater than 10 and are photochemically and thermally unstable. In addition, these compounds are readily degraded by microbial and plant metabolism. Examples of CHD herbicides include clethodim, sethoxydim, cycloxydim, alloxydim, tralkoxydim, tepraloxydim, clefoxydim, clefoxyfim, butroxydim, and profoxydim.

[0003] Clethodim is an important commercial herbicide in the CHD class. Clethodim is a selective post-emergence CHD herbicide used to control annual and perennial grasses in a variety of broadleaf crops such as soybean, cotton, flax, peanuts, sunflower, sugarbeet, potato, alfalfa, and most vegetables.

[0004] Herbicidal compositions comprising clethodim as an active ingredient are difficult to formulate because clethodim is chemically unstable. For example, the presence of adjuvant materials, surfactants, and even water can result in significant chemical degradation of clethodim in the herbicidal composition.

[0005] It has been found that long-term stability of herbicidal formulations comprising CHD, particularly clethodim, is challenging and there remains a need to develop stable compositions comprising CHD wherein the rate of degradation of the compound is controlled and its concentration is maintained over a longer period of time. Therefore, there is a great need to develop a physically and chemically stable composition with excellent stability during the preparation, storage, and application of the herbicidal composition. SUMMARY

[0006] In one aspect, the present disclosure provides a stable herbicidal composition comprising:

[0007] at least one cyclohexenedione oxime herbicide or an agriculturally acceptable salt thereof; and

[0008] a stabilizer system comprising a dialkyl metal sulfosuccinate and a non-ionic surfactant.

[0009] In one aspect, the non-ionic surfactant comprises a sorbitan fatty acid ester.

[0010] In one aspect, the cyclohexenedione oxime herbicide comprises clethodim.

[0011] In another aspect, the present disclosure provides a stabilizer system comprising a dialkyl metal sulfosuccinate and a non-ionic surfactant in a ratio of 1:10 to 10:1, more preferably in a ratio of 1:5 to 5:1.

[0012] In yet another aspect, the present disclosure provides a method of making a stabilized herbicidal composition comprising: at least one cyclohexenedione oxime herbicide or an agriculturally acceptable salt thereof, and a stabilizer system comprising a dialkyl metal sulfosuccinate and a non-ionic surfactant in a ratio of 1:5 to 5:1, wherein the method comprises mixing the cyclohexenedione oxime herbicide with the stabilizer system to produce the stabilized herbicidal composition.

[0013] In one aspect, the non-ionic surfactant comprises a sorbitan fatty acid ester. In one aspect, the cyclohexenedione oxime comprises clethodim.

[0014] In yet another aspect, the present disclosure provides a method of making a stabilized herbicidal composition, the method comprising:

[0015] providing a stabilizer system comprising a dialkyl metal sulfosuccinate, a non-ionic surfactant, and a solvent, and optionally one or more auxiliary ingredients; and

[0016] adding a cyclohexenedione oxime or an agriculturally acceptable salt thereof to the stabilizer system to obtain a stabilized composition.

[0017] In another aspect, the present disclosure provides a method of controlling weeds, the method comprising applying an effective amount of a herbicidal composition to a weed, a crop, a locus, or an area of habitat, the herbicidal composition comprising:

[0018] at least one cyclohexenedione oxime herbicide or an agriculturally acceptable salt thereof; and

[0019] a stabilizer system comprising a dialkyl metal sulfosuccinate and a non-ionic surfactant in a ratio of 1:10 to 10:1.

[0020] In another aspect, the present disclosure provides use of the stable herbicidal composition disclosed herein to control a wide range of weeds.

[0021] In another aspect, the present disclosure provides a kit. The kit comprises a plurality of components, each of which can comprise at least one or more of the ingredients of the stable herbicidal composition of the present disclosure. DETAILED DESCRIPTION

[0022] The present disclosure provides a stable herbicidal composition comprising a cyclohexenedione oxime herbicide.

[0023] It is another object of the present disclosure to provide a stable clethodim herbicidal composition with efficient clethodim recovery.

[0024] It is another object of the present disclosure to provide a method of preparing a stable herbicidal composition comprising a cyclohexenedione oxime compound.

[0025] It is yet another object of the present disclosure to provide a method of using a stable herbicidal composition comprising a cyclohexenedione oxime compound on weeds.

[0026] For purposes of the present disclosure, it is understood that the present application can take various alternative variations and step sequences, unless explicitly indicated otherwise. Further, except in any operation examples, or where otherwise indicated, all numbers expressing amounts of materials / ingredients and conditions used in the specification are to be understood as being modified in all instances by the term "about." This term

[0027] Accordingly, before the present disclosure is disclosed and described in detail, it is to be understood that the present disclosure is not limited to the particular system or process described as an example, which can, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of the present disclosure. Examples, including examples of any terminology discussed herein, used anywhere in this specification are included to further provide a state of the art but are not intended to limit the scope of the present disclosure or any example embodiments.

[0028] Before the present methods, systems and articles are disclosed and described, it is to be understood that the methods, systems and articles are not limited to only the specific embodiments disclosed and described. As such, it is not intended to limit the scope of the claims, but rather, claims may include any number of alternatives, modifications and / or equivalents to the features or positions described and illustrated. Numerous specific embodiments have been set forth herein to provide a thorough and complete disclosure of the methods, systems and articles. It will be apparent, however, to one of ordinary skill in the art that embodiments in accordance with the present disclosure can be practiced without combining all of the features and / or steps set forth in the example embodiments.

[0029] The use of the terms “a” and “the”, and similar indicators (particularly in the context of the claims), should be interpreted to cover both the singular and the plural, unless otherwise stated herein or clearly contradicted by the context. The terms first, second, etc., as used herein, do not imply any particular order, but are merely for convenience to indicate, for example, multiple layers. Unless otherwise stated, the terms “comprising,” “having,” “including,” and “containing” should be understood as open-ended terms (i.e., meaning “including but not limited to”).

[0030] As used herein, “about” or “approximately” includes the value and means within an acceptable deviation range of a particular value as determined by one of ordinary skill in the art, taking into account the measurement in question and the error associated with the measurement of the particular quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±10% or ±5% of the value. Unless otherwise stated herein, the listing of numerical ranges is intended only as a shorthand method for individually referring to each individual value falling within the range, and each individual value is included in the specification as if it were listed individually herein. The endpoints of all ranges are included within the range and can be combined independently. It should be understood that, where a parameter range is provided, all integers within the range and their tenths are also provided. For example, “0.1%-80%” includes 0.1%, 0.2%, 0.3%, etc., up to 80%.

[0031] All methods described herein may be performed in a suitable order unless otherwise stated herein or clearly contradicted by the context. The use of any and all examples or exemplary language (e.g., “such as”) is merely intended to better illustrate the invention and, unless otherwise required, does not constitute a limitation on the scope of the invention. No language in this specification should be construed as indicating that any unclaimed element is necessary for the practice of the invention as used herein.

[0032] As used herein, the terms “plant” or “crop” refer to the whole plant, plant organs (such as leaves, stems, shoots, roots, trunks, branches, buds, fruits, etc.), plant cells, or plant seeds. The term also includes plant crops such as fruits.

[0033] The term "plant" may also include its propagation material, which may include all reproductive parts of a plant that can be used for plant propagation, such as seeds, as well as vegetative plant material such as cuttings and tubers. This includes seeds, tubers, spores, bulbs, rhizomes, shoots, basal shoots, stolons, and buds, as well as other parts of the plant, including seedlings and young plants awaiting transplantation after germination or emergence from the soil.

[0034] As used herein, the term "location" refers to a nearby area or region designated for the desired growth of a crop, where the prevention of weed spread is desired. A location includes the vicinity of the desired crop plants, where weeds have already appeared, are most likely to appear, or have not yet appeared.

[0035] As used herein, "effective amount" refers to the amount of an active ingredient, such as a herbicide, that has an adverse effect on weeds. Adverse effects include one or more of the following: deviation from natural growth, killing of weeds, structural damage to weeds, drying, and / or growth delay.

[0036] As used in this article, “agriculturally acceptable salt” means salt that is known and accepted for agricultural or horticultural use.

[0037] As used herein, the term “stable” refers to the chemical and / or physical stabilization of an active compound (e.g., a herbicide).

[0038] As used herein, “alkyl” refers to a straight-chain or branched saturated aliphatic hydrocarbon having a specified number of carbon atoms. Alkyl groups include, for example, groups having 1 to 50 carbon atoms (C1 to C50 alkyl). “Dialkyl” refers to a compound containing two alkyl groups in its molecule.

[0039] "Alkali metals" refers to the metallic elements in Group 1 of the periodic table, namely lithium, sodium, potassium, rubidium, cesium, and francium. "Alkali earth metals" refers to the metals in Group 2 of the periodic table, namely beryllium, magnesium, calcium, strontium, barium, and radium.

[0040] Cyclohexanedione oxime is an effective herbicide. Therefore, the terms "cyclohexanedione oxime herbicide," "cyclohexanedione oxime," and "cyclohexanedione oxime compound" are used interchangeably in this disclosure.

[0041] The terms "polysorbate" or "polyoxyethylene sorbitol ester" are used interchangeably to refer to compounds synthesized by polymeric addition of ethylene oxide to sorbitol fatty acid esters. These "polyoxyethylene sorbitol esters" are also known as polysorbates.

[0042] As used in this article, aromatic fluid solvents refer to C9-C10 aromatic hydrocarbon solvents that are highly aromatic and naphthalene-poor.

[0043] As used herein, "methyl ester solvent" is a mixture of long-chain fatty acid methyl esters, such as a mixture of C16-18 alkyl unsaturated fatty acid methyl esters and C18 alkyl unsaturated fatty acid methyl esters. In one aspect, methyl ester solvent is a mixture of unsaturated (C16-C18)-alkyl carboxylic acid methyl esters and unsaturated (C18)-alkyl carboxylic acid methyl esters, which are vegetable oil derivatives. Examples of methyl ester solvents include soybean oleate methyl ester.

[0044] The term “recovery percentage” or “recovery%” refers to the amount of active cyclohexenedion oxime herbicide (e.g., clethodim) retained in the composition after being stored for a defined period of time under accelerated thermal stability (AHS) conditions (about 54°C) and / or low temperature conditions (e.g., about -10°C).

[0045] The term "emulsion stability" refers to the ability of a system to resist changes in its physicochemical properties over a period of time.

[0046] As previously mentioned, herbicidal compositions containing cyclohexenone oxime herbicides (such as clethodim) as active ingredients are difficult to formulate because these compounds tend to be chemically unstable in herbicidal compositions. For example, the presence of adjuvant materials, surfactants, or even water can lead to significant chemical degradation of clethodim in the herbicidal composition. Given that chemical stability is a commercially desirable factor, various solutions have been proposed in the prior art to stabilize cyclohexenone oximes such as clethodim in formulations.

[0047] PCT Publication No. WO 2007 / 050090 discloses a stable composition comprising clethodim and a mixture of the following substances: C1-C8 alkyl esters of fatty acids, nonionic surfactants, polyoxyethylene (POE) derivatives of tallow or vegetable oils, POE sorbitol esters, ethylene oxide-propylene oxide (EO-PO) block polymers, POE alkylphenols, polyoxyethylene polyaryl ethers, ethoxylated alcohols, POE fatty acid esters, alkyl polyglycosides, alkyl polysaccharides, POE fatty amines, and polymeric surfactants. The composition does not contain two specific anionic surfactants: dialkyl metal sulfosuccinates and metal alkyl aromatic sulfonates. These compositions, containing significant amounts of fatty acid methyl ester adjuvants and POE tallow amine ether sulfates, contribute to long-term chemical stability.

[0048] PCT Publication No. WO 2011 / 011265 discloses a composition comprising a cyclohexenedione oxime herbicide and an effective amount of a stabilizer comprising epoxidized oil fatty acids or epoxidized fatty acid esters. It also discloses one or more of the following as anionic surfactants: mono- and / or diesters of long-chain alcohols having 14 to 22 carbon atoms, phosphate mono- and diesters of alkylene oxide addition products of long-chain alcohols having 14 to 22 carbon atoms, polyoxyethylene alkyl ether sulfates of alcohols having 14 to 22 carbon atoms, alkyl sulfonates having 14 to 22 carbon atoms, and olefin sulfonates having 14 to 22 carbon atoms; and ethoxylated fatty acids, alcohol ethoxylates, tristyrylphenol ethoxylates, and ethoxylated dehydrated sorbitol fatty acid esters, and mixtures thereof.

[0049] PCT Publication No. WO2016 / 196130 discloses a stable composition comprising a cyclohexenedione oxime compound or an agriculturally acceptable salt; and an effective amount of one or more stabilizing surfactants; wherein the composition is substantially free of epoxidized oil fatty acids or epoxidized fatty acid esters. According to WO2016 / 196130, the presence of anionic surfactants such as sulfonic acid derivatives, alcohol ethoxylates, alkylphenol ethers that prevent the degradation of clethodim, and alkylbenzene sulfonic acids or their salts, alone or in combination with nonionic surfactants, leads to higher degradation of clethodim.

[0050] The inventors of this disclosure unexpectedly discovered that a stable composition of cyclohexenedione oxime herbicide can be obtained by using a stabilizer system comprising a dialkyl metal sulfosuccinate in a ratio of 1:10 to 10:1, preferably 1:5 to 5:1, and one or more nonionic surfactants (such as sorbitol fatty acid esters).

[0051] As used herein, the term "ratio" refers to a weight ratio. Within the range of said ratios, the stabilizer system comprising dialkyl metal sulfosuccinate and nonionic surfactant (i.e., sorbitol fatty acid ester) prevents degradation of the cyclohexenedione oxime herbicide in the liquid composition and exhibits high stability during the preparation, storage, and application of the composition.

[0052] The stable herbicidal composition also exhibits an effective recovery rate of cyclohexenedionone oxime herbicide and good emulsion stability.

[0053] Therefore, the present invention provides a stable herbicidal composition comprising:

[0054] (a) at least one cyclohexenedion oxime herbicide or an agriculturally acceptable salt thereof; and

[0055] (b) A stabilizer system comprising a dialkyl metal sulfosuccinate and at least one nonionic surfactant.

[0056] In a preferred embodiment, this disclosure provides a stable weed-control composition comprising:

[0057] (a) at least one cyclohexenedion oxime herbicide or an agriculturally acceptable salt thereof; and

[0058] (b) A stabilizer system comprising a dialkyl metal sulfosuccinate and at least one nonionic surfactant in a ratio of 1:10 to 10:1.

[0059] In one embodiment, the cyclohexenedione oxime herbicide includes clethodim, butyrazosulfuron, clethodim, cloproxydim, thiamethoxam, chlorpyrifos, pyranoblon, styraxazol, agriculturally acceptable salts thereof, or combinations thereof.

[0060] In one embodiment, the cyclohexenedion oxime herbicide in the stable herbicidal composition is clethodim.

[0061] In one embodiment, the cyclohexenedione oxime herbicide in the stable herbicidal composition is cyclohexenedion.

[0062] In one embodiment, based on the total weight of the stable herbicidal composition, the stable herbicidal composition contains about 0.1% by weight (w / w) to about 70% by weight (w / w) or about 1% by weight (w / w) to about 60% by weight (w / w) of cyclohexanedione oxime.

[0063] In one embodiment, the stable herbicidal composition comprises, based on the total weight of the stable herbicidal composition, an amount of cyclohexanedione oxime herbicide ranging from about 5% w / w to about 50% w / w.

[0064] In one embodiment, the stable herbicidal composition comprises, based on the total weight of the stable herbicidal composition, about 10% w / w to about 40%, or about 10% w / w to about 30% w / w, or about 10% w / w to about 20% w / w of a cyclohexanedione oxime herbicide.

[0065] In one embodiment, the stable herbicidal composition comprises a stabilizer system.

[0066] According to one embodiment, this disclosure provides a stabilizer system comprising a dialkyl metal sulfosuccinate and a nonionic surfactant.

[0067] In one embodiment, the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester.

[0068] Therefore, in one embodiment, this disclosure provides a stable herbicidal composition comprising:

[0069] (a) at least one cyclohexenedion oxime herbicide or an agriculturally acceptable salt thereof; and

[0070] (b) A stabilizer system comprising dialkyl metal sulfosuccinate and sorbitol fatty acid ester.

[0071] In one embodiment, the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:100 to 100:1.

[0072] In one embodiment, the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:10 to 10:1.

[0073] In one embodiment, the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:5 to 5:1.

[0074] In one embodiment, the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:2 to 2:1.

[0075] In one embodiment, the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a 1:1 ratio.

[0076] In one embodiment, the stable herbicide composition comprises, based on the total weight of the stable herbicide composition, about 0.01% w / w to about 60% w / w or about 0.1% w / w to about 50% w / w of a stabilizer system.

[0077] In a preferred embodiment, the stable herbicide composition comprises a stabilizer system of about 5% w / w to about 30% w / w, based on the total weight of the stable herbicide composition.

[0078] In one embodiment, the stabilizer system comprises a dialkyl metal sulfosuccinate.

[0079] In one embodiment, the stabilizer system comprises a dialkyl metal sulfosuccinate, which includes C6-C 12 Dialkyl alkali metal sulfonyl succinate, C6-C 12 Dialkyl alkaline earth metal sulfosuccinates or combinations thereof.

[0080] In one embodiment, the dialkyl metal sulfosuccinate includes sodium dioctyl sulfosuccinate, calcium dioctyl sulfosuccinate, lithium dioctyl sulfosuccinate, barium dioctyl sulfosuccinate, potassium dioctyl sulfosuccinate, magnesium dioctyl sulfosuccinate, or combinations thereof.

[0081] In one embodiment, the dialkyl metal sulfosuccinate comprises or consists of sodium dioctyl sulfosuccinate.

[0082] In one embodiment, the dialkyl metal sulfosuccinate comprises or is composed of calcium dioctyl sulfosuccinate.

[0083] In one embodiment, the dialkyl metal sulfosuccinate comprises or is composed of magnesium dioctyl sulfosuccinate.

[0084] In one embodiment, based on the total weight of the stable herbicidal composition, the stable herbicidal composition comprises about 0.01% w / w to about 50% w / w, or about 0.1% w / w to about 40% w / w, or about 0.5% w / w to about 30% w / w of a dialkyl metal sulfosuccinate.

[0085] In a preferred embodiment, the stable herbicidal composition comprises about 1% w / w to about 20% w / w of dialkyl metal sulfosuccinate, based on the total weight of the stable herbicidal composition.

[0086] According to one embodiment, the nonionic surfactant comprises ethoxylated fatty acids, alcohol ethoxylates, tristyrylphenol ethoxylates, sorbitol fatty acid esters, ethoxylated sorbitol fatty acid esters, or combinations thereof. Examples of ethoxylated sorbitol fatty acid esters include polyoxyethylene sorbitol esters, widely known as polysorbate esters. Sorbitol fatty acid esters are monoesters, diesters, or tripesters of fatty acids linked to sorbitol.

[0087] In one embodiment, the nonionic surfactant is anhydrous sorbitol fatty acid ester.

[0088] In one embodiment, the stabilizer system comprises sorbitol fatty acid esters.

[0089] In one embodiment, the sorbitol fatty acid ester comprises a polyoxyethylene sorbitol fatty acid ester, which is synthesized by adding one or more ethylene oxide groups to the sorbitol fatty acid ester via a polymerization reaction.

[0090] In one embodiment, the dehydrated sorbitol fatty acid ester comprises polysorbate 20, polysorbate 60, polysorbate 65, polysorbate 80, or combinations thereof. Polysorbates 20, 60, 65, and 80 respectively use lauric acid, monostearate, tristearate, and oleate as the fatty acid portion of the molecule.

[0091] In one embodiment, the sorbitol fatty acid ester is polysorbate 80, wherein the total number of poly(ethylene glycol) units is 20 and each end is capped with an oleoyl group.

[0092] In one embodiment, based on the total weight of the stable herbicidal composition, the stable herbicidal composition comprises about 0.01% w / w to about 50% w / w, or about 0.1% w / w to about 40% w / w, or about 0.5% w / w to about 30% w / w of dehydrated sorbitol fatty acid esters.

[0093] In one embodiment, the stable herbicidal composition comprises, based on the total weight of the stable herbicidal composition, about 1% w / w to about 20% w / w or about 1% w / w to about 10% w / w of dehydrated sorbitol fatty acid esters.

[0094] In one embodiment, the stable weed-control composition comprises:

[0095] (i) at least one cyclohexenedion oxime herbicide or an agriculturally acceptable salt thereof; and

[0096] (ii) A stabilizer system comprising dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:10 to 10:1.

[0097] In one embodiment, the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:5 to 5:1.

[0098] In one embodiment, the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a 1:1 ratio.

[0099] In one embodiment, the cyclohexenedion oxime herbicide is clethodim and the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:10 to 10:1 or 1:5 to 5:1.

[0100] In one embodiment, the cyclohexenedion oxime herbicide is clethodim or an agriculturally acceptable salt thereof, and the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:5 to 5:1.

[0101] In one embodiment, the cyclohexenedion oxime herbicide is clethodim or an agriculturally acceptable salt thereof; and the stabilizer system comprises a dialkyl metal sulfosuccinate and anhydrous sorbitol fatty acid ester in a 1:1 ratio.

[0102] In one embodiment, the cyclohexenedion oxime herbicide is clethodim or an agriculturally acceptable salt thereof, and the stabilizer system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a ratio of 1:10 to 10:1.

[0103] In one embodiment, the cyclohexenedion oxime herbicide is clethodim or an agriculturally acceptable salt thereof, and the stabilizer system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a ratio of 1:5 to 5:1.

[0104] In one embodiment, the cyclohexenedione oxime herbicide is clethodim or an agriculturally acceptable salt thereof, and the stabilizer system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a 1:1 ratio.

[0105] In one embodiment, the cyclohexenedione oxime herbicide is cyclohexidine or an agriculturally acceptable salt thereof, and the stabilizer system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a ratio of 1:10 to 10:1.

[0106] In one embodiment, the cyclohexenedione oxime herbicide is cyclohexidine or an agriculturally acceptable salt thereof, and the stabilizer system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a ratio of 1:5 to 5:1.

[0107] In one embodiment, the cyclohexenedione oxime herbicide is cyclohexidine or an agriculturally acceptable salt thereof, and the stabilizer system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a 1:1 ratio.

[0108] In another embodiment, the stable herbicidal composition may also contain a solvent.

[0109] In one embodiment, the stable herbicidal composition comprises a solvent, including a nonpolar water-immiscible solvent, a polar aprotic water-miscible organic solvent, or a combination thereof.

[0110] In one embodiment, the solvent in the stable herbicidal composition includes a nonpolar, water-immiscible solvent, such as a substituted or unsubstituted aromatic or aliphatic hydrocarbon, an alkyl ester of a substituted or unsubstituted vegetable oil, or a combination thereof.

[0111] Non-limiting examples of aromatic hydrocarbons include benzene or substituted benzene derivatives, such as toluene, xylene, 1,2,4-trimethylbenzene, naphthalene, mixtures of naphthalene and 1,2,4-trimethylbenzene, or combinations thereof. Specific examples include: Aromatic 150, Aromatic 200, heavy aromatic naphtha solvents containing <10% naphthalene and <1.7% 1,2,4-trimethylbenzene, or combinations thereof.

[0112] In one embodiment, the solvent in the stable herbicidal composition is a C1-C4 alkyl ester of C5-C20 saturated or unsaturated fatty acids, a mixture of such esters, or a C6-C4 alkyl ester. 20 -C6-C20-C5 ...

[0113] In one implementation, C5-C from vegetable oil 20C1-C4 alkyl esters (preferably methyl esters) of saturated or unsaturated fatty acids or mixtures thereof include, but are not limited to, methyl, ethyl and butyl esters of low-erucic acid rapeseed (B. napus) oil, linseed oil, safflower (Carthamus tinctorius L.) oil, soybean oil, sunflower oil or combinations thereof.

[0114] In one embodiment, the solvent in the stable herbicidal composition is C5-C. 20 At least one methyl ester of a fatty acid.

[0115] In one embodiment, the solvent in the stable herbicidal composition is a mixture of C16-18 unsaturated fatty acid methyl ester and C18-unsaturated fatty acid methyl ester.

[0116] In one embodiment, the solvent in the stable herbicidal composition is a water-miscible polar aprotic solvent, including, for example, C1-C10 alkyl lactate, isopropyl lactate, C1-C10 alkyl carbonate, polyethylene glycol, polyethylene glycol C1-C10 alkyl ether, polypropylene glycol, polypropylene glycol C1-C10 alkyl ether, or combinations thereof.

[0117] In one embodiment, the stable herbicidal composition contains about 1% w / w to about 99% w / w or about 10% w / w to about 90% w / w solvent, based on the total weight of the stable herbicidal composition.

[0118] In one embodiment, the stable herbicidal composition contains about 30% w / w to about 80% w / w of solvent, based on the total weight of the stable herbicidal composition.

[0119] In one embodiment, the stable weed-control composition may also contain additional herbicides. The type of herbicide is not limited.

[0120] In one embodiment, the stable weed-control composition may also contain one or more safeners. The type of safener is not limited.

[0121] In one embodiment, the stable herbicidal composition may contain one or more adjuvants, including surfactants (emulsifiers), crop oils, fertilizers, dispersants, compatibilizers, foaming activators, defoaming agents, regulators, spray colorants (dyes), or combinations thereof.

[0122] In one embodiment, the stable herbicidal composition comprises, based on the total weight of the stable herbicidal composition, about 0.1% w / w to about 30% w / w or about 0.5% w / w to about 25% w / w of an adjuvant.

[0123] In one embodiment, the stable herbicidal composition is formulated as a liquid composition. Liquid compositions include, but are not limited to, emulsifiable concentrates (EC), soluble liquids (SL), microemulsions (ME), suspension concentrates (SC), capsule suspensions (CS), combinations of capsule suspensions and suspension concentrates as ZC, or any combination thereof.

[0124] According to one embodiment of this disclosure, the stable herbicidal composition is formulated as an emulsifiable concentrate (EC).

[0125] In one embodiment, the stable herbicidal composition of the present invention is formulated as a solid composition, including but not limited to powder, granule, pellet, tablet, dry suspension, wettable powder, water-dispersible granules (WDG), or combinations thereof.

[0126] The stable compositions disclosed herein may further comprise one or more adjuvants selected from dispersants, wetting agents, fillers, surfactants, anti-caking agents, pH adjusters, preservatives, antimicrobial agents, defoamers, colorants, and other formulation aids.

[0127] Exemplary dispersants include ionic and nonionic dispersants such as polystyrene sulfonates, polyvinyl sulfonates, salts of naphthalene sulfonic acid / formaldehyde condensates, salts of naphthalene sulfonic acid, phenol sulfonic acid and formaldehyde condensates, and lignin sulfonates such as sodium lignin sulfonate and modified sodium lignin sulfonate; polyethylene oxide / polypropylene oxide block copolymers, polyethylene glycol ethers of linear alcohols, reaction products of fatty acids with ethylene oxide and / or propylene oxide, polyvinyl alcohol, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone, copolymers of (meth)acrylic acid and (meth)acrylates, alkyl ethoxylates, alkyl aryl ethoxylates, ethoxylated alkyl aryl phosphates, sulfated esters, or any combination thereof.

[0128] Exemplary wetting agents include salts of soaps, silicone oils, magnesium stearate, and aliphatic monoesters of sulfuric acid, including but not limited to sodium lauryl sulfate; sulfonyl alkyl amides and their salts, including but not limited to sodium N-methyl-N-oleoyl taurate; alkyl aryl sulfonates, including but not limited to alkylbenzene sulfonates, alkyl naphthalene sulfonates and their salts; and lignin sulfonates, including but not limited to sodium diisopropylnaphthalene sulfonate.

[0129] Exemplary fillers include insoluble and soluble fillers, such as silica, amorphous silica, pyrolytic diatomaceous earth, kaolin, clay, and bentonite.

[0130] Exemplary defoamers include silicones, long-chain alcohols, and fatty acid salts.

[0131] Exemplary colorants include, for example, red, blue, and green colorants, and are preferably pigments and water-soluble dyes that are slightly soluble in water. Examples include inorganic colorants such as iron oxide, titanium oxide, and ferric hexacyanate, and organic colorants such as madder pigment, azo dyes, and phthalocyanine dyes.

[0132] In one embodiment, the stable weed-control composition comprises:

[0133] (i) a cyclohexenedione oxime herbicide of about 0.1% w / w to about 70% w / w, and

[0134] (ii) a stabilizer system of approximately 0.01% w / w to approximately 60% w / w,

[0135] The stabilizer system comprises about 0.01% w / w to about 50% w / w of dialkyl metal sulfosuccinate and about 0.01% w / w to about 50% w / w of sorbitol fatty acid ester, each based on the total weight of the stabilized herbicidal composition.

[0136] In one embodiment, the stable weed-control composition comprises:

[0137] (i) Cyclohexenedione oxime herbicides of about 1% w / w to about 50% w / w, and

[0138] (ii) a stabilizer system of approximately 1% w / w to approximately 50% w / w.

[0139] The stabilizer system comprises about 0.5% w / w to about 30% w / w of dialkyl metal sulfosuccinate and about 0.5% w / w to about 30% w / w of dehydrated sorbitol fatty acid ester, each based on the total weight of the stabilized herbicidal composition.

[0140] In one embodiment, the stable weed-control composition comprises:

[0141] (i) Cyclohexenedione oxime herbicides of about 10% w / w to about 40% w / w, and

[0142] (ii) a stabilizer system of about 1% w / w to about 10% w / w

[0143] The stabilizer system comprises about 0.5% w / w to about 30% w / w of dialkyl metal sulfosuccinate and about 0.5% w / w to about 30% w / w of dehydrated sorbitol fatty acid ester, each based on the total weight of the stabilized herbicidal composition.

[0144] In one embodiment, the stable herbicidal composition comprises about 1% w / w to about 50% w / w, or about 10% w / w to about 40% w / w, of a cyclohexenedione oxime herbicide and 1% w / w to about 50% w / w, or about 1% w / w to about 10%, of a stabilizer system, wherein the stabilizer system comprises about 0.5% w / w to about 30% w / w of a dialkyl metal sulfosuccinate and about 0.5% w / w to about 30% w / w of anhydrous sorbitol fatty acid ester, each based on the total weight of the stable herbicidal composition, and wherein the stable herbicidal composition is an emulsifiable concentrate (EC).

[0145] In one embodiment, this disclosure provides a method for preparing a stable herbicidal composition, the method comprising:

[0146] Provides a stabilizer system comprising a dialkyl metal sulfosuccinate, a nonionic surfactant, a solvent, and optionally one or more auxiliary components; and

[0147] Cyclohexenedione oxime or an agriculturally acceptable salt thereof is added to a stabilizer system to provide a stable herbicidal composition, wherein the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:10 to 10:1.

[0148] In one embodiment, the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:5 to 5:1.

[0149] In one embodiment, a method for preparing a stable herbicidal composition includes:

[0150] a) Mixing a solvent, a dialkyl metal sulfosuccinate, anhydrous sorbitol fatty acid ester, and optionally one or more auxiliary ingredients to form a stabilizer system; and

[0151] b) Add cyclohexenedione oxime herbicide to the stabilizer system to obtain a stable herbicidal composition.

[0152] In one embodiment, this disclosure provides a method for preparing a stable herbicidal composition, the method comprising:

[0153] a) Mixing a solvent, a dialkyl metal sulfosuccinate, anhydrous sorbitol fatty acid esters, and optionally one or more auxiliary ingredients to form a stabilizer mixture;

[0154] b) Adding cyclohexenedione oxime herbicide to the stabilizer mixture under low shear conditions; and

[0155] c) Emulsify the mixture under low shear to obtain a stable herbicidal composition as an emulsifiable concentrate (EC).

[0156] As used herein, “low shear” refers to mixing that occurs through non-turbulent (e.g., smooth or laminar) flow. For example, low shear conditions exist when materials are mixed at low speeds and the particles of the material move in an ordered manner throughout the mixer without causing turbulence in the mixture.

[0157] According to one embodiment of this disclosure, a stabilizer system is formed by a mixture of solvent, dialkyl metal sulfosuccinate, and sorbitol fatty acid ester under low shear conditions to promote emulsification.

[0158] According to one embodiment of this disclosure, the addition of cyclohexenedione oxime and optionally another herbicide to the stabilizer system is also carried out under low shear to obtain the final EC composition according to the invention.

[0159] According to one embodiment of this disclosure, the mixing and emulsification steps in the method are carried out at a temperature in the range of about 20°C to about 80°C, or about 20°C to about 70°C.

[0160] According to one embodiment of this disclosure, emulsification takes place over a period of about 30 seconds to about 24 hours or about 5 minutes to about 3 hours.

[0161] According to one embodiment of this disclosure, the average particle size of cyclohexenedion oxime herbicides (e.g., clethodim) is about 0.01 μm to about 100 μm or about 0.01 μm to about 10 μm.

[0162] According to one embodiment of this disclosure, the operating conditions for producing particles of the desired size will depend on a variety of factors, including (where applicable) the temperature at which emulsification is carried out, the rate of addition of components of the stabilizer system, the type of solvent and specific active ingredients, reactants, the emulsification equipment used, the amount of emulsifier used, etc.

[0163] According to one embodiment of this disclosure, a method for controlling weeds includes applying an effective amount of a herbicidal composition to weeds, crops, the site, or a habitat area, said herbicidal composition comprising:

[0164] At least one cyclohexenedion oxime or an agriculturally acceptable salt thereof; and

[0165] A stabilizer system comprising a dialkyl metal sulfosuccinate and a nonionic surfactant in a ratio of 1:10 to 10:1.

[0166] According to one embodiment of this disclosure, the stabilizer system comprises dialkyl metal sulfosuccinate and nonionic surfactant in a ratio of 1:5 to 5:1.

[0167] According to one embodiment of this disclosure, the stabilizer system comprises dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:5 to 5:1.

[0168] According to one embodiment of this disclosure, a method for controlling weeds includes applying an effective amount of a herbicidal composition to weeds, crops, the site, or a habitat area, said herbicidal composition comprising:

[0169] (i) clethodim; and

[0170] (ii) A stabilizer system comprising dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:10 to 10:1 or in a ratio of 1:5 to 5:1.

[0171] According to one embodiment of this disclosure, after storing the stable herbicidal composition of this disclosure for a defined period of 14 days under accelerated thermal stability (AHS) conditions (about 54°C) and / or low temperature conditions (e.g., about -10°C), the recovery percentage of the amount of active cyclohexenedione oxime herbicide retained in the composition is in the range of 95% to 100%, indicating the effective stability of the composition.

[0172] According to one embodiment of this disclosure, after storing the stable herbicidal composition of this disclosure for a defined period of 14 days under accelerated thermal stability (AHS) conditions (about 54°C) and / or low temperature conditions (e.g., about -10°C), the recovery percentage of the amount of active ingredient (i.e. clethodim) retained in the composition is in the range of 96% to 99%, thus demonstrating the effective stability of the composition.

[0173] In compositions that do not contain nonionic surfactants, after storing the stable herbicidal composition of this disclosure for a defined period of 14 days under accelerated thermal stability (AHS) conditions (about 54°C) and / or low temperature conditions (e.g., about -10°C), the amount of active ingredient (i.e. clethodim) retained in the composition is reduced by at least 8%, thus indicating that such compositions are unstable.

[0174] According to one embodiment of this disclosure, the stable herbicidal composition is used to control a wide range of weeds.

[0175] According to one embodiment of this disclosure, the stable herbicidal composition is used to control broad-spectrum annual and perennial weeds in the pre-emergence and post-emergence stages.

[0176] According to one embodiment of this disclosure, the form of a stable herbicidal composition allows the active compound to be effectively absorbed by plants.

[0177] According to one embodiment of this disclosure, a stable herbicidal composition is used as a source of active agricultural chemical ingredients and is typically diluted to provide an end-use formulation, typically a spray formulation. The herbicidal composition can be diluted with water by 1 to 10,000 times, particularly 10 to 1,000 times, the total weight of the stable herbicidal composition to form a spray formulation. The stable herbicidal composition can be diluted prior to use to provide an agricultural chemical active ingredient concentration of about 0.5% by weight (wt.%) to about 1 wt.%. In the diluted composition, the agricultural chemical active ingredient concentration can range from about 0.001 wt.% to about 1 wt.% of the total formulation (in spray formulation form).

[0178] Aerosol formulations comprise all components intended for application to plants or their environment. Aerosol formulations can be prepared by simply diluting a stable herbicidal composition containing an agrochemical active ingredient, or by mixing individual agrochemical active ingredients, or by combining a diluted stable herbicidal composition with other individual agrochemical active ingredients or mixtures of agrochemical active ingredients. Typically, such final-use mixing is carried out in a can from which the formulation is sprayed, or alternatively, in a holding can used to fill the spray can. Such mixing and blending are commonly referred to as can-mixing and can-blending.

[0179] According to one embodiment of this disclosure, a kit comprising a stable agrochemical composition is provided. The kit contains multiple components, including at least one component of the stable herbicidal composition of the present invention.

[0180] According to one embodiment of this disclosure, the kit comprises:

[0181] At least one cyclohexenedion oxime herbicide or an agriculturally acceptable salt thereof; and

[0182] A stabilizer system comprising a dialkyl metal sulfosuccinate and anhydrous sorbitol fatty acid ester in a ratio of 1:10 to 10:1.

[0183] According to one embodiment of this disclosure, the kit comprises: at least one cyclohexenedione oxime herbicide or an agriculturally acceptable salt thereof; and a stabilizer system comprising a dialkyl metal sulfosuccinate and anhydrous sorbitol fatty acid ester in a ratio of 1:5 to 5:1.

[0184] In one embodiment of this disclosure, the kit may contain at least one or all of the components that can be used to prepare a stable herbicidal composition. For example, the kit may contain a cyclohexenedione herbicide, another herbicide, and a stabilizer system comprising a dialkyl metal sulfosuccinate and anhydrous sorbitol fatty acid ester. One or more of the components may have been combined or pre-formulated. In those embodiments where the kit provides more than two components, the components may have been combined and therefore packaged in a single container, such as a vial, bottle, can, sachet, bag, and / or jar.

[0185] In other embodiments, two or more components of the kit may be packaged separately, i.e., not pre-formulated. Therefore, the kit may include one or more separate containers, such as vials, jars, bottles, pouches, bags, and / or jars, each containing a separate component for stabilizing the herbicidal composition.

[0186] In both forms, the components of the kit may be applied separately from or together with other components, or as components of a combined composition according to the invention for preparing a stable herbicidal composition according to the invention.

[0187] It should be understood that this specification and examples are illustrative and not intended to limit the scope of this disclosure, and those skilled in the art will recognize other embodiments within the spirit and scope of the invention. Other embodiments that also fall within the scope of this invention can be practiced. The following examples illustrate the invention but are not intended to limit the scope of the claims.

[0188] Example

[0189] This disclosure will be described with reference to the following embodiments.

[0190] Example 1 : Preparation of clethodim 120 g / L emulsifiable concentrate (EC)

[0191] Table 1

[0192] Ingredient Amount (% w / w) Clethodim 13.09 Methyl ester solvent 48.85 Sodium dioctyl sulfosuccinate 5.00 Polysorbate 80 5.00 Aromatic fluid type solvent 28.06 Total 100

[0193] The materials in Table 1 were used to prepare the herbicidal composition of Example 1. Specifically, 48.85 g of methyl ester solvent and 28.06 g of aromatic fluid solvent were mixed with a separately prepared stabilizer system obtained by mixing 5 g of sodium dioctyl sulfosuccinate and 5 g of polysorbate 80 under low shear to obtain a mixture. Then, 13.09 g of clethodim was added to the mixture under low shear to obtain a clear amber liquid as a stable emulsifiable concentrate.

[0194] Example 2: Preparation of clethodim 120 g / L emulsifiable concentrate (EC)

[0195] Table 2

[0196]

[0197]

[0198] The materials in Table 2 were used to prepare the herbicidal composition of Example 2. Clethodim, methyl ester solvent, sodium dioctyl sulfosuccinate, polysorbate 80, and aromatic fluid solvent were mixed at the concentrations shown in Table 2 above, and the EC composition was prepared according to the method of Example 1.

[0199] Example 3: Preparation of clethodim 120 g / L emulsifiable concentrate (EC)

[0200] Table 3

[0201] Ingredient Amount (% w / w) Clethodim 12 Methyl ester solvent 48.85 Sodium dioctyl sulfosuccinate 3.75 Polysorbate 80 3.75 Aromatic fluid type solvent 31.65 Total 100

[0202] The materials in Table 3 were used to prepare the herbicidal composition of Example 3. Clethodim, methyl ester solvent, sodium dioctyl sulfosuccinate, polysorbate 80, and aromatic fluid solvent were mixed in the given ratios shown in Table 3 above, and the EC composition was prepared according to the method of Example 1.

[0203] Example 4: Preparation of clethodim 120 g / L emulsifiable concentrate (EC) (comparative example)

[0204] Table 4

[0205] Ingredient Amount (% w / w) Clethodim 12 Methyl ester solvent 44.8 Sodium dioctyl sulfosuccinate 3.33 Castor oil ethoxylate (40 EO) 6.66 Aromatic fluid type solvent 33.21 Total 100

[0206] The materials in Table 4 were used to prepare the herbicidal composition of Example 4. Clethodim, methyl ester solvent, sodium dioctyl sulfosuccinate, castor oil ethoxylate (40EO), and aromatic fluid solvent were mixed in the given ratios shown in Table 4, and the EC composition was prepared according to the method of Example 1.

[0207] Stability of formulations containing clethodim (14 day period) and stability of the diluted products

[0208] The EC compositions of Examples 1 to 4 were prepared as described above. The stability of clethodim in the EC compositions and the stability of the diluted emulsions were investigated.

[0209] The EC compositions of Examples 1, 2, and 3 were found to be fairly stable after 0 days of storage under ambient conditions (room temperature and relative humidity) (i.e., immediately after preparation). These EC compositions were also investigated after 14 days of storage under accelerated thermal stability (AHS) conditions (54°C) and low temperature conditions (-10°C). As shown in Table 5, the degradation of clethodim in Examples 1 through 3 was within acceptable limits after storage under both high (AHS) and low temperature conditions. However, the EC composition of Example 4 showed greater clethodim degradation (change %, i.e., a reduction of clethodim in the composition of 8.21%), making the system quite unstable.

[0210] The stability of the emulsions after dilution at a 2% dilution rate was also investigated. The emulsions obtained by diluting the compositions of Examples 1, 2, and 3 remained stable after 1 hour of dilution and after 24 hours of dilution, and were stored at room temperature. After 1 hour, the amount of emulsification in Examples 1 to 3 was minimal. Under both conditions (1 hour and 24 hours), the amount of emulsification in Example 1 remained under control, i.e., less than 1 ml. This suggests high stability of the emulsion at final use. Furthermore, in the composition of Example 4, the amount of emulsification remained under control; however, the composition of Example 4 was unfavorable for use due to a higher percentage of clethodim degradation. (Table 5)

[0211] Table 5

[0212]

[0213] Al: Active ingredient

[0214] Optimization of the stable system

[0215] To investigate the effect of various ratios of dialkyl metal sulfosuccinate and sorbitol fatty acid esters on the stabilization system, various compositions (Examples 5 to 11) were developed using various weight ratios such as 1:1 in Examples 5 to 7, 3:2 in Example 8, 1:5 in Example 9, 5:1 in Example 10, and 2:3 in Example 11. It was found that clethodim remained fairly stable when the dialkyl metal sulfosuccinate and sorbitol fatty acid esters of the stabilizing system were mixed in weight ratios ranging from 1:5 to 5:1. Furthermore, the emulsion remained stable when tested at 1 hour and 24 hours (Table 6). Therefore, the stabilization system comprising dialkyl metal sulfosuccinate and sorbitol fatty acid esters was found to be effective in imparting emulsion stability and preventing clethodim degradation.

[0216] Table 6

[0217]

[0218]

[0219] *Ex - Example.

[0220] The results clearly demonstrate that clethodim compositions comprising a stabilizing system containing dialkyl metal sulfosuccinate and sorbitol fatty acid esters are stable. Therefore, it has been advantageously discovered that stabilized herbicidal compositions comprising a cyclohexenedione oxime herbicide and a stabilizer system comprising dialkyl metal sulfosuccinate and sorbitol fatty acid esters in a weight ratio of 1:5 to 5:1. This stabilizer system successfully stabilizes the cyclohexenedione oxime herbicide, clethodim, in the composition and also imparts stability to the diluted emulsion for final use. Therefore, this disclosure provides at least the following advantages.

[0221] A stable herbicidal composition for effective control of weeds.

[0222] A stable cyclohexenedione oxime herbicide composition exhibiting effective active ingredient recovery and emulsion stability after storage.

[0223] The disclosed herbicidal composition improves the method of controlling weed growth and solves the problem of poor control of herbicide efficacy due to reduced recovery and emulsion stability observed in the cyclohexenedion oxime herbicide composition.

[0224] While the subject matter of the invention has been shown and described with reference to preferred embodiments thereof, those skilled in the art will understand that many substitutions, modifications, and variations can be made to the invention without departing from its spirit and scope. Therefore, the invention is intended to cover all such substitutions, modifications, and variations falling within the spirit and broad scope of the appended claims.

Claims

1. A stable herbicidal composition, said stable herbicidal composition comprising: At least one cyclohexenedione oxime herbicide or an agriculturally acceptable salt thereof; and The stabilizer system comprises dialkyl metal sulfosuccinate and a nonionic surfactant. The nonionic surfactant mentioned above includes sorbitol fatty acid esters, and the composition is an emulsifiable concentrate. The stabilizer system comprises the dialkyl metal sulfosuccinate and the nonionic surfactant in a ratio of 1:5 to 5:

1. The cyclohexenedion oxime herbicide described herein includes clethodim or an agriculturally acceptable salt thereof, and The dialkyl metal sulfosuccinates include sodium dioctyl sulfosuccinate, calcium dioctyl sulfosuccinate, lithium dioctyl sulfosuccinate, barium dioctyl sulfosuccinate, potassium dioctyl sulfosuccinate, magnesium dioctyl sulfosuccinate, or combinations thereof.

2. The stable herbicidal composition according to claim 1, wherein the dehydrated sorbitol fatty acid ester comprises polysorbate 20, polysorbate 60, polysorbate 65, polysorbate 80, or a combination thereof.

3. The stable herbicidal composition according to claim 1, wherein the stable system comprises the dialkyl metal sulfosuccinate and the dehydrated sorbitol fatty acid ester in a ratio of 1:

2.

4. The stable herbicidal composition according to claim 1, wherein the stable system comprises the dialkyl metal sulfosuccinate and the dehydrated sorbitol fatty acid ester in a ratio of 2:

1.

5. The stable herbicidal composition according to claim 1, wherein the stable system comprises the dialkyl metal sulfosuccinate and the dehydrated sorbitol fatty acid ester in a ratio of 1:

1.

6. The stable herbicidal composition according to claim 1, wherein, based on the total weight of the herbicidal composition, the composition comprises 0.1% w / w to 70% w / w of cyclohexenedion oxime and 0.01% w / w to 60% w / w of the stabilizer system. Based on the total weight of the herbicidal composition, the stabilizer system comprises 0.01% w / w to 50% w / w of the dialkyl metal sulfosuccinate and 0.01% w / w to 50% w / w of the nonionic surfactant.

7. A method for preparing the stable herbicidal composition according to claim 1, the method comprising: Provided is the stabilizer system comprising the dialkyl metal sulfosuccinate, the nonionic surfactant, a solvent, and optionally one or more auxiliary components; as well as The cyclohexenone oxime or an agriculturally acceptable salt thereof is added to the stabilizer system to provide the stable herbicidal composition. The stabilizer system comprises the dialkyl metal sulfosuccinate and sorbitol fatty acid ester in a ratio of 1:5 to 5:

1. The nonionic surfactant mentioned above includes sorbitol fatty acid esters, and the composition is an emulsifiable concentrate. The cyclohexenedion oxime herbicide described herein includes clethodim or an agriculturally acceptable salt thereof, and The dialkyl metal sulfosuccinates include sodium dioctyl sulfosuccinate, calcium dioctyl sulfosuccinate, lithium dioctyl sulfosuccinate, barium dioctyl sulfosuccinate, potassium dioctyl sulfosuccinate, magnesium dioctyl sulfosuccinate, or combinations thereof.

8. The method according to claim 7, wherein the method further comprises: The solvent, the dialkyl metal sulfosuccinate, the dehydrated sorbitol fatty acid ester, and optionally one or more of the auxiliary components are mixed to form the stabilizer system; The cyclohexanedione oxime is added to the stabilizer system under low shear conditions to obtain a mixture, wherein the cyclohexanedione includes clethodim; and The mixture obtained above is emulsified under low shear to obtain the stable herbicidal composition as an emulsifiable concentrate (EC).

9. A method for controlling weeds, the method comprising applying an effective amount of the herbicidal composition according to claim 1 to the weeds, crops, location, or habitat area.

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