Stable herbicide compositions

Abstract

STABLE HERBICIDE COMPOSITIONS. Stable herbicide compositions are described herein, including at least one cyclohexenedione oxime herbicide or an agriculturally acceptable salt thereof; and a stabilizing system comprising a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester. A process for preparing the stable herbicide composition and a method for controlling weeds by applying the stable herbicide composition to a weed, crop, locus, or habitat area are also disclosed.

Description

Descriptive report of the invention patent for COMPOSITIONS STABLE HERBICIDES FIELD OF THE INVENTION:

[0001] The present disclosure relates to stable herbicidal compositions. More particularly, the present disclosure relates to stable herbicidal compositions, including a cyclohexanedione oxime herbicide and a stabilizing system. The present disclosure further relates to a process for preparing stable herbicidal compositions and to methods for controlling weeds. BACKGROUND OF THE INVENTION

[0002] Cyclohexanedione (CHD) oxime herbicides, which are effective at relatively low doses and readily decomposed, were developed to reduce the environmental impact of herbicides. CHD herbicides have herbicidal activity against various post-emergent grass weeds. Regarding persistence in the environment, CHD herbicides are susceptible to rapid degradation by biotic and abiotic processes. For example, these herbicides decompose at pH less than 5 and greater than 10, and are photochemically and thermally unstable. Furthermore, these compounds are readily degraded through microbial and plant metabolism. Examples of CHD herbicides include clethodim, sethoxydim, cycloxydim, aloxydim, tralkoxydim, tepraloxydim, clefoxydim, clefoxydim, butroxydim, and profoxydim.

[0003] Clethodim is an important commercial herbicide within the class of CHDs. It is a selective post-emergence CHD herbicide used to control annual and perennial grasses in a wide variety of broadleaf crops, including soybeans, cotton, flax, peanuts, sunflowers, sugar beets, potatoes, alfalfa, and most vegetables.

[0004] Herbicide compositions comprising clethodim as an active ingredient are difficult to formulate because clethodim is chemically unstable. The presence of adjuvant materials, surfactants, and even water, for example, can lead to significant chemical degradation of clethodim in a herbicide composition. Petition 870260060795, dated 06 / 22 / 2026, page 12 / 79 2 / 32

[0005] It has been found that the long-term stability of a herbicide formulation containing a CHD, especially clethodim, is challenging, and there remains a need to develop a stable composition comprising a CHD in which the rate of degradation of the compound is controlled and its concentration is maintained over a longer period of time. Therefore, the development of a physically and chemically stable composition that has excellent stability during the preparation, storage, and application process of the herbicide composition is highly desirable. SUMMARY

[0006] In one aspect, the present disclosure provides a stable herbicidal composition comprising at least one cyclohexanedione oxime herbicide or an agriculturally acceptable salt thereof; and a stabilizing system comprising a dialkyl metal sulfosuccinate and a nonionic surfactant.

[0007] In one aspect, the nonionic surfactant comprises a sorbitan fatty acid ester.

[0008] In one aspect, the cyclohexanedione oxime herbicide comprises clethodim.

[0009] In another aspect, the present disclosure provides a stabilizing system comprising a dialkyl metal sulfosuccinate and a nonionic surfactant in a ratio of 1:10 to 10:1, and more preferably in a ratio of 1:5 to 5:1.

[0010] In yet another aspect, the present disclosure provides a process for preparing a stable herbicidal composition comprising at least one cyclohexanedione oxime herbicide or an agriculturally acceptable salt thereof, and a stabilizing system comprising a dialkyl metal sulfosuccinate, a nonionic surfactant in a ratio of 1:5 to 5:1, wherein said process comprises mixing the cyclohexanedione oxime herbicide with the stabilizing system to produce a stable herbicidal composition. Petition 870260060795, dated 06 / 22 / 2026, page 13 / 79 3 / 32

[0011] In one aspect, the nonionic surfactant comprises a sorbitan fatty acid ester. In one aspect, the cyclohexanedione oxime comprises clethodim.

[0012] In yet another aspect, the present disclosure provides a process for preparing a stable herbicidal composition comprising: To provide a stabilizing system comprising a metal dialkyl sulfosuccinate, a nonionic surfactant and a solvent and, optionally, one or more adjuvant ingredients; and to add a cyclohexanedione oxime or an agriculturally acceptable salt thereof to the stabilizing system to obtain a stabilized composition.

[0013] In another aspect, the present disclosure provides a method of weed control, wherein the method comprises applying an effective amount of a herbicide composition to a weed, a crop, a locus or a habitat area, wherein the herbicide composition comprises: at least one cyclohexanedione oxime herbicide or an agriculturally acceptable salt thereof; and a stabilizing system comprising a dialkyl metal sulfosuccinate and a nonionic surfactant in a ratio of 1:10 to 10:1.

[0014] In another aspect, the present disclosure provides the use of a stable herbicide composition disclosed herein for controlling a wide range of weeds.

[0015] In another aspect, the present disclosure provides a kit. The kit comprises a plurality of components, each of which may include at least one, or more, of the ingredients of the stable herbicide composition of the present disclosure. DETAILED DESCRIPTION

[0016] The present disclosure provides stable herbicidal compositions, including cyclohexanedione oxime herbicides. Petition 870260060795, dated 06 / 22 / 2026, page 14 / 79 4 / 32

[0017] It is an objective of the present disclosure to provide a stable clethodim herbicide composition with efficient clethodim recovery.

[0018] Another objective of the present disclosure is to provide a process for preparing stable herbicidal compositions comprising a cyclohexanedione oxime compound.

[0019] It is yet another objective of the present disclosure to provide a method of using stable herbicidal compositions comprising a cyclohexanedione oxime compound on weeds.

[0020] For the purposes of this disclosure, it should be understood that the invention may assume various variations and alternative sequences of steps, except where expressly specified otherwise. Furthermore, except for any operational examples or indications to the contrary, all numbers expressing, for example, quantities of materials / ingredients used in the descriptive report, should be understood as being modified in all cases by the term approximately.

[0021] Thus, before describing the present invention in detail, it should be understood that this invention is not limited to the systems particularly exemplified or to process parameters which may, of course, vary. It should also be understood that the terminology used herein is for the purpose of describing specific embodiments of the invention only and is not intended to limit the scope of the invention in any way. The use of examples anywhere in this descriptive report, including examples of any terms discussed herein, is for illustrative purposes only, and in no way limits the scope and meaning of the invention or of any exemplified term.

[0022] Before defining the present subject in detail, it may be useful to provide definitions of certain terms used herein. Except where otherwise defined, all technical and scientific terms used herein have the same meaning that is commonly understood by one skilled in the art to which this invention pertains. The following definitions are provided for the sake of clarity. Petition 870260060795, dated 06 / 22 / 2026, p. 15 / 79 5 / 32

[0023] The use of the terms a, an, and the, and similar terms (especially in the context of claims) should be interpreted as encompassing both the singular and the plural, unless otherwise indicated in this document or clearly contradicted by the context. The terms first, second, etc., as used herein, are not intended to denote any specific ordering, but simply for convenience to denote a plurality, for example, of layers. The terms comprising, having, including, and containing should be interpreted as open terms (i.e., meaning including but not limited to), unless otherwise indicated.

[0024] About or approximately, as used herein, includes the stated value and means within an acceptable range of deviation for the specific value, as determined by one skilled in the art, considering the measurement in question and the error associated with measuring the specific quantity (i.e., the limitations of the measuring system). For example, about may mean within one or more standard deviations or within ±10% or ±5% of the stated value. The citation of value ranges is intended merely as a shorthand method of individually referring to each separate value within the range, except where otherwise indicated in the present invention, and each separate value is incorporated into the descriptive report as if it were individually cited in the present invention. The test endpoints of all ranges are included in the range and combinable independently.It is understood that when a range of parameters is provided, all integers within that range, and tenths thereof, are also provided. For example, 0.1 to 80% includes 0.1%, 0.2%, 0.3%, etc., up to 80%.

[0025] All methods described herein may be performed in any suitable order, except where otherwise indicated in the present invention or otherwise clearly contradicted by the context. The use of any and all examples, or illustrative language (e.g., such as) is for the sole purpose of better illustrating the invention and does not represent a limitation on the scope of the invention. Petition 870260060795, dated 06 / 22 / 2026, page 16 / 79 6 / 32 unless otherwise claimed. No language in the descriptive report should be interpreted as indicating any unclaimed element as essential to the practice of the invention, as used herein.

[0026] As used herein, the term plant or agricultural crop refers to whole plants, plant organs (e.g., leaves, stems, branches, roots, trunks, limbs, shoots, fruits, etc.), plant cells, or plant seeds. This term also encompasses plant crops, such as fruits.

[0027] The term plant may additionally include its propagation material, which may include all the plant's generating parts, such as seeds and vegetative material of the plant, such as seedlings and tubers, that can be used for plant reproduction. This includes seeds, tubers, spores, bulbs, rhizomes, basal shoots, stolons and buds, and other plant parts, including seedlings and young plants, which must be transplanted after germination or after emerging from the soil.

[0028] The term locus, as used herein, denotes the adjacency or area designated for the growth of a desired agricultural crop in which weed spread control is desired. The locus includes the adjacency of desired agricultural crop plants where weeds have emerged, are more likely to emerge, or are yet to emerge.

[0029] As used herein, effective amount is an amount of an active ingredient, such as a herbicide, that has an adverse effect on a weed. The adverse effect includes one or more of these: disruption of natural development, death of the weed, structural damage to the weed, desiccation, and / or growth retardation.

[0030] As used herein, an agriculturally acceptable salt means a salt that is known and accepted for agricultural or horticultural use.

[0031] As used herein, the term stable refers to the chemical and / or physical stabilization of an active compound (e.g., herbicide). Petition 870260060795, dated 06 / 22 / 2026, page 17 / 79 7 / 32

[0032] Alkyl, as used herein, means a saturated aliphatic hydrocarbon with a straight or branched chain having a specified number of carbon atoms. Alkyl groups include, for example, groups having from 1 to 50 carbon atoms (C1 to C50 alkyl). Dialkyl means a compound that includes two alkyl groups in the molecule.

[0033] Alkali metal means a metal from Group 1 of the periodic table of elements, namely lithium, sodium, potassium, rubidium, cesium and francium. Alkaline earth metal means a metal from Group 2 of the periodic table of elements, namely beryllium, magnesium, calcium, strontium, barium and radium.

[0034] Cyclohexanedione oximes are effective herbicides. Therefore, the terms cyclohexanedione oxime herbicide, cyclohexanedione oxime, and cyclohexanedione oxime compound are used interchangeably in this disclosure.

[0035] The terms polysorbates or polyoxyethylene sorbitan esters are used interchangeably to refer to compounds that are synthesized by adding ethylene oxide to a sorbitan fatty acid ester via polymerization. These polyoxyethylene sorbitan esters are also referred to as polysorbates.

[0036] As used herein, an aromatic fluid-based solvent refers to a C9-C10 hydrocarbon solvent with a high degree of aromaticity and without naphthalene.

[0037] As used herein, a methyl ester solvent is a mixture of long-chain fatty acid methyl esters, for example, a mixture of C16-18 alkyl unsaturated fatty acid methyl ester and C18 alkyl unsaturated fatty acid methyl ester. In one aspect, the methyl ester solvent is a mixture of unsaturated alkylcarboxylic acid methyl esters and unsaturated alkylcarboxylic acid methyl esters, which are derived from vegetable oil. An example of a methyl ester solvent includes soybean methyl ester. Petition 870260060795, dated 06 / 22 / 2026, p. 18 / 79 8 / 32

[0038] The terms percentage recovery or % recovery refer to the amount of active cyclohexanedione oxime herbicide (e.g., clethodim) remaining in the stable herbicide composition of the present disclosure after storing the composition 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).

[0039] The term emulsion stability refers to the ability of the system to resist changes in its physical-chemical properties over a period of time.

[0040] As mentioned earlier, herbicidal compositions comprising a cyclohexenone oxime herbicide, for example, clethodim, as an active ingredient, are difficult to formulate, since these compounds tend to be chemically unstable in a herbicidal composition. The presence of adjuvant materials, surfactants, and even water, for example, can lead to significant chemical degradation of clethodim in a herbicidal composition. Given that chemical stability is a commercially desirable factor, several solutions have been proposed in the prior art to stabilize a cyclohexenone oxime, such as clethodim, in the formulation.

[0041] PCT Publication No. WO 2007 / 050090 discloses a stable composition comprising clethodim and a mixture of C1-C8 alkyl esters of fatty acids, nonionic surfactants, polyoxyethylene (POE) derivatives of tallow or vegetable oils, sorbitan POE esters, ethylene oxide-propylene oxide (EO-PO) block polymers, POE alkylphenols, polyoxyalkylene polyaryl ethers, ethoxylated alcohols, POE fatty acid esters, alkyl polyglycosides, alkyl polysaccharides, fatty POE amines and polymeric surfactants. The composition excludes two specific anionic surfactants: metal dialkyl sulfosuccinates and metal alkylaromatic sulfonates. These compositions, having significant amounts of a fatty acid methyl ester adjuvant and tallow sulfate Petition 870260060795, dated 06 / 22 / 2026, p. 19 / 79 9 / 32 amino ether of POE plays a role in conferring chemical stability over an extended period of time.

[0042] PCT Publication No. WO 2011 / 011265 discloses a composition comprising a cyclohexanedione oxime herbicide and an effective amount of a stabilizer comprising an epoxidized oil fatty acid or an epoxidized fatty acid ester.It also discloses one or more of the following: long-chain mono- and / or diester phosphoric alcohols having from 14 to 22 carbon atoms, and the salts thereof; mono- and diester phosphoric alcohols of alkylene oxide addition products of long-chain alcohols having from 14 to 22 carbon atoms and the salts thereof; alkyl sulfates having from 14 to 22 carbon atoms; polyoxyethylene alkyl ether sulfates of alcohols having from 14 to 22 carbon atoms; alkanesulfonates having from 14 to 22 carbon atoms; and olefinsulfonates having from 14 to 22 carbon atoms as anionic surfactants; and ethoxylated fatty acids, alcohol ethoxylates, tristyrylphenol ethoxylates and ethoxylated sorbitan fatty acid esters, and mixtures thereof.

[0043] PCT Publication WO 2016 / 196130 discloses a stable composition comprising a cyclohexanedione oxime compound or an agriculturally acceptable salt; and an effective amount of one or more stabilizing surfactants; the composition being substantially free of an epoxidized fatty acid or an epoxidized fatty acid ester. According to WO 2016 / 196130, the presence of anionic surfactants such as sulfonic acid derivatives, alcohol ethoxylates and alkylphenolic ethers prevented the degradation of clethodim, and the presence of alkylbenzenesulfonic acid or its salts, alone or in combination with non-ionic surfactants, resulted in greater degradation of clethodim.

[0044] The inventors of the present disclosure have unexpectedly discovered that a stable composition of a cyclohexanedione oxime herbicide can be obtained through the use of a stabilizing system comprising a metal dialkyl sulfosuccinate and one or more nonionic surfactants, such as esters. Petition 870260060795, dated 06 / 22 / 2026, page 20 / 79 10 / 32 of sorbitan fatty acid, in a ratio in the range of 1:10 to 10:1, preferably 1:5 to 5:1.

[0045] As used here, the term ratio refers to a ratio in weight. Within the aforementioned ratio range, the stabilizing system comprising metal dialkyl sulfosuccinate and non-ionic surfactants, namely sorbitan fatty acid esters, prevents the degradation of the cyclohexanedione oxime herbicide in the liquid composition and has high stability during the preparation, storage, and application process of the composition.

[0046] The said stable herbicide composition also has an efficient % recovery of the cyclohexanedione oxime herbicide and good emulsion stability.

[0047] Thus, the present invention provides a stable herbicidal composition comprising: (a) at least one cyclohexanedione oxime herbicide, or an agriculturally acceptable salt thereof; and (b) a stabilizing system comprising a metal dialkyl sulfosuccinate and a nonionic surfactant.

[0048] In a preferred embodiment, the present disclosure provides a stable herbicidal composition comprising: (a) at least one cyclohexanedione oxime herbicide, or an agriculturally acceptable salt thereof; and (b) a stabilizing system comprising a metal dialkyl sulfosuccinate and at least one nonionic surfactant in a ratio of 1:10 to 10:1.

[0049] In one embodiment, the cyclohexanedione oxime herbicide comprises aloxidim, butroxidim, clethodim, chlorproxidim, cycloxidim, profoxidim, sethoxidim, tepraloxidim, tralkoxyim, an agriculturally acceptable salt thereof, or a combination thereof.

[0050] In one embodiment, the cyclohexanedione oxime herbicide in the stable herbicide composition is clethodim. Petition 870260060795, dated 06 / 22 / 2026, page 21 / 79 11 / 32

[0051] In one embodiment, the cyclohexanedione oxime herbicide in the stable herbicide composition is sethoxydim.

[0052] In one embodiment, the stable herbicide composition comprises from about 0.1% by weight by weight (w / w) to about 70% w / w, or from about 1% w / w to about 60% w / w, of cyclohexanedione oxime, based on the total weight of the stable herbicide composition.

[0053] In one embodiment, the stable herbicide composition comprises the cyclohexanedione oxime herbicide in an amount of about 5% w / w to about 50% w / w, based on the total weight of the stable herbicide composition.

[0054] In one embodiment, the stable herbicide composition comprises about 10% w / w about 40%, or about 10% w / w about 30% w / w, or about 10% w / w about 20% w / w of the cyclohexanedione oxime herbicide, based on the total weight of the stable herbicide composition.

[0055] In one embodiment, the stable herbicide composition comprises a stabilizing system.

[0056] According to one embodiment, the present disclosure provides a stabilizing system comprising a metal dialkyl sulfosuccinate and a nonionic surfactant.

[0057] In one embodiment, the stabilizing system comprises a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester.

[0058] Thus, in one embodiment, the present disclosure provides a stable herbicidal composition comprising: (a) at least one cyclohexanedione oxime herbicide, or an agriculturally acceptable salt thereof; and (b) a stabilizing system comprising a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester.

[0059] In one embodiment, the stabilizing system comprises a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a ratio of 1:100 to 100:1. Petition 870260060795, dated 06 / 22 / 2026, page 22 / 79 12 / 32

[0060] In one embodiment, the stabilizing system comprises a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a ratio of 1:10 to 10:1.

[0061] In one embodiment, the stabilizing system comprises a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a ratio of 1:5 to 5:1.

[0062] In one embodiment, the stabilizing system comprises a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a ratio of 1:2 to 2:1.

[0063] In one embodiment, the stabilizing system comprises a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a 1:1 ratio.

[0064] In one embodiment, the stable herbicide composition comprises of about 0.01% w / w about 60% w / w, or of about 0.1% w / w about 50% w / w, of the stabilizing system based on the total weight of the stable herbicide composition.

[0065] In a preferred embodiment, the stable herbicide composition comprises from about 5% w / w to about 30% w / w of the stabilizing system, based on the total weight of the stable herbicide composition.

[0066] In one embodiment, the stabilizing system comprises a metal dialkyl sulfosuccinate.

[0067] In one embodiment, the stabilizing system comprises a metal dialkyl sulfosuccinate comprising an alkali metal C6C12 dialkyl sulfosuccinate, an alkaline earth metal C6-C12 dialkyl sulfosuccinate, or a combination thereof.

[0068] In one embodiment, the metal dialkyl sulfosuccinate comprises sodium dioctyl sulfosuccinate, calcium dioctyl sulfosuccinate, lithium dioctyl sulfosuccinate, barium dioctyl sulfosuccinate, potassium dioctyl sulfosuccinate, magnesium dioctyl sulfosuccinate, or a combination thereof. Petition 870260060795, dated 06 / 22 / 2026, page 23 / 79 13 / 32

[0069] In one embodiment, the metal dialkyl sulfosuccinate comprises or consists of sodium dioctyl sulfosuccinate.

[0070] In one embodiment, the metal dialkyl sulfosuccinate comprises or consists of calcium dioctyl sulfosuccinate.

[0071] In one embodiment, the metal dialkyl sulfosuccinate comprises or consists of magnesium dioctyl sulfosuccinate.

[0072] In one embodiment, the stable herbicide composition comprises about 0.01% w / w about 50% w / w, or about 0.1% w / w about 40% w / w, or about 0.5% w / w about 30% w / w of metal dialkyl sulfosuccinate, based on the total weight of the stable herbicide composition.

[0073] In a preferred embodiment, the stable herbicide composition comprises from about 1% w / w to about 20% w / w of metal dialkyl sulfosuccinate, based on the total weight of the stable herbicide composition.

[0074] According to one embodiment, the nonionic surfactant comprises an ethoxylated fatty acid, an alcohol ethoxylate, tristyrylphenol ethoxylate, a sorbitan fatty acid ester, an ethoxylated sorbitan fatty acid ester, or a combination thereof. Examples of ethoxylated sorbitan fatty acid esters include polyoxyethylene sorbitan esters widely known as polysorbates. A sorbitan fatty acid ester is a mono-, di-, or triester of fatty acids linked to sorbitan.

[0075] In one embodiment, the nonionic surfactant is a sorbitan fatty acid ester.

[0076] In one embodiment, the stabilizing system comprises a sorbitan fatty acid ester.

[0077] In one embodiment, the sorbitan fatty acid ester comprises a polyoxyethylene sorbitan fatty acid ester that is synthesized by adding one or more ethylene oxide groups to a sorbitan fatty acid ester via a polymerization reaction. Petition 870260060795, dated 06 / 22 / 2026, page 24 / 79 14 / 32

[0078] In one embodiment, the sorbitan fatty acid ester comprises polysorbate 20, polysorbate 60, polysorbate 65, polysorbate 80, or a combination thereof. Polysorbates 20, 60, 65, and 80 utilize lauric acid, monostearate, tristearate, and oleate, respectively, for the fatty acid portion of the molecule.

[0079] In one embodiment, the sorbitan fatty acid ester is polysorbate 80, where the total number of poly(ethylene glycol) units is 20, and a single terminal is terminated by an oleoyl group.

[0080] In one embodiment, the stable herbicide composition comprises about 0.01% w / w about 50% w / w, or about 0.1% w / w about 40% w / w, or about 0.5% w / w about 30% w / w of sorbitan fatty acid ester based on the total weight of the stable herbicide composition.

[0081] In one embodiment, the stable herbicide composition comprises from about 1% w / w to about 20% w / w of sorbitan fatty acid ester, or from about 1% w / w to about 10% w / w based on the total weight of the stable herbicide composition.

[0082] In one embodiment, the stable herbicidal composition comprises: (i) at least one cyclohexanedione oxime herbicide or an agriculturally acceptable salt thereof; and (ii) a stabilizing system comprising a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a ratio of 1:10 to 10:1.

[0083] In one embodiment, the stabilizing system comprises a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a ratio of 1:5 to 5:1.

[0084] In one embodiment, the stabilizing system comprises a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a 1:1 ratio. Petition 870260060795, dated 06 / 22 / 2026, page 25 / 79 15 / 32

[0085] In one embodiment, the cyclohexanedione oxime herbicide is clethodim, and the stabilizing system comprises a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a ratio of 1:10 to 10:1, or in a ratio of 1:5 to 5:1.

[0086] In one embodiment, the cyclohexanedione oxime herbicide is clethodim, or an agriculturally acceptable salt thereof, and the stabilizing system comprises metal dialkyl sulfosuccinate and sorbitan fatty acid ester in a ratio of 1:5 to 5:1.

[0087] In one embodiment, the cyclohexanedione oxime herbicide is clethodim, or an agriculturally acceptable salt thereof; and the stabilizing system comprises metal dialkyl sulfosuccinate and sorbitan fatty acid ester in a 1:1 ratio.

[0088] In one embodiment, the cyclohexanedione oxime herbicide is clethodim or an agriculturally acceptable salt thereof, and the stabilizing system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a ratio of 1:10 to 10:1.

[0089] In one embodiment, the cyclohexanedione oxime herbicide is clethodim or an agriculturally acceptable salt thereof, and the stabilizing system comprises sodium dioctyl sulfosuccinate and polysorbate 80, in a ratio of 1:5 to 5:1.

[0090] In one embodiment, the cyclohexanedione oxime herbicide is clethodim or an agriculturally acceptable salt thereof, and the stabilizing system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a 1:1 ratio.

[0091] In one embodiment, the cyclohexanedione oxime herbicide is sethoxydim or an agriculturally acceptable salt thereof, and the stabilizing system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a ratio of 1:10 to 10:1.

[0092] In one embodiment, the cyclohexanedione oxime herbicide is sethoxydim or an agriculturally acceptable salt thereof, and the stabilizing system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a ratio of 1:5 to 5:1. Petition 870260060795, dated 06 / 22 / 2026, page 26 / 79 16 / 32

[0093] In one embodiment, the cyclohexanedione oxime herbicide is sethoxydim or an agriculturally acceptable salt thereof, and the stabilizing system comprises sodium dioctyl sulfosuccinate and polysorbate 80 in a 1:1 ratio.

[0094] In a further embodiment, the stable herbicidal composition may additionally comprise a solvent.

[0095] In one embodiment, the stable herbicidal composition comprises a solvent comprising a non-polar water-immiscible solvent, a polar aprotic water-miscible organic solvent, or a combination thereof.

[0096] In one embodiment, the solvent in the stable herbicidal composition comprises a non-polar water-immiscible solvent, for example, a substituted or unsubstituted aromatic or aliphatic hydrocarbon, a substituted or unsubstituted alkyl ester of a vegetable oil, or a combination thereof.

[0097] Non-limiting examples of aromatic hydrocarbons include benzene or substituted benzene derivatives such as toluene, xylene, 1,2,4-trimethylbenzene, naphthalene or a mixture of naphthalene and 1,2,4-trimethylbenzene, or a combination thereof. Specific examples include: aromatic 150, aromatic 200, a heavy aromatic naphtha solvent containing <10% naphthalene and <1.7% 1,2,4-trimethylbenzene, or a combination thereof.

[0098] In one embodiment, the solvent in the stable herbicide composition is a C1-C4 alkyl ester of a saturated or unsaturated C5-C20 fatty acid, a mixture of these esters, a C6-C20 fatty acid monoglyceride, a C6-C20 fatty acid diglyceride, and / or a C6-C20 fatty acid triglyceride. In another embodiment, the solvent is a methyl ester of a saturated or unsaturated C5-C20 fatty acid.

[0099] In one embodiment, the C1-C4 alkyl ester (preferably the methyl ester) of a saturated or unsaturated C5-C20 fatty acid, or a mixture of these vegetable oil esters, includes, without limitation, methyl, ethyl and butyl esters. Petition 870260060795, dated 06 / 22 / 2026, page 27 / 79 17 / 32 canola oil (B. napus), linseed oil, safflower oil (Carthamus tinctorius L.), soybean oil, sunflower oil, or a combination thereof.

[0100] In one embodiment, the solvent in the stable herbicide composition is at least one methyl ester of a C5-C20 fatty acid.

[0101] In one embodiment, the solvent in the stable herbicide composition is a mixture of unsaturated C16-18 fatty acid methyl esters and unsaturated C18 fatty acid methyl esters.

[0102] In one embodiment, the solvent in the stable herbicidal composition is a water-miscible polar aprotic solvent including, for example, a C1-C10 alkyl lactate, isopropyl lactate, a C1-C10 alkyl carbonate, polyethylene glycol, C1-C10 alkyl ether of polyethylene glycol, polypropylene glycol, C1-C10 alkyl ethers of polypropylene glycol, or a combination thereof.

[0103] In one embodiment, the stable herbicide composition comprises of about 1% w / w about 99% w / w, or of about 10% w / w about 90% w / w of solvent, based on the total weight of the stable herbicide composition.

[0104] In one embodiment, the stable herbicide composition comprises from about 30% w / w to about 80% w / w of solvent, based on the total weight of the stable herbicide composition.

[0105] In one embodiment, the stable herbicide composition may additionally include an additional herbicide. The type of herbicide is not limited.

[0106] In one embodiment, the stable herbicide composition may additionally include one or more protectants. The type of protectant is limited.

[0107] In one embodiment, the stable herbicidal composition may include one or more adjuvants comprising surfactants (emulsifier), vegetable oil, fertilizers, dispersing agents, compatibility agents, foam activators, foam suppressants, correctives, spray dyes (tints) or a combination thereof. Petition 870260060795, dated 06 / 22 / 2026, page 28 / 79 18 / 32

[0108] In one embodiment, the stable herbicide composition comprises of about 0.1% w / w to about 30% w / w, or of about 0.5% w / w to about 25% w / w of an adjuvant, based on the total weight of the stable herbicide composition.

[0109] In one embodiment, the stable herbicide composition is formulated as a liquid composition. The liquid composition includes, but is not limited to, an emulsifiable concentrate (EC), a soluble liquid (SL), a microemulsion (ME), a suspension concentrate (SC), a capsule suspension (CS), a combination of capsule suspension and suspension concentrate, such as ZC, or any combination thereof.

[0110] According to one embodiment of the present disclosure, the stable herbicide composition is formulated as an emulsifiable concentrate (EC).

[0111] In one embodiment, the stable herbicidal composition of the present invention is formulated as a solid composition including, but not limited to, dust, powder, granules, pellets, tablets, wettable flowable dry powder, water-dispersible granules (WDG) or a combination thereof.

[0112] The stable composition of the present disclosure may further comprise one or more adjuvants selected from dispersants, wetting agents, fillers, surfactants, anti-caking agents, pH regulators, preservatives, biocides, antifoaming agents, colorants and other formulation adjuvants.

[0113] Exemplary dispersants include ionic and non-ionic dispersants such as polystyrene sulfonic acid salts, polyvinylsulfonic acid salts, naphthalenesulfonic acid / formaldehyde condensate salts, naphthalenesulfonic acid, phenolsulfonic acid and formaldehyde condensate salts, and lignosulfonic acid salts such as sodium lignosulfonate and modified sodium lignosulfonate; 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, polyvinyl alcohol copolymers and Petition 870260060795, dated 06 / 22 / 2026, page 29 / 79 19 / 32 polyvinylpyrrolidone, copolymers of (meth)acrylic acid and (meth)acrylic esters, alkyl ethoxylates, alkylaryletoxylates, phosphated alkylaryletoxylates, a sulfated ester or any combination thereof.

[0114] Exemplary wetting agents include soaps, silicone oil, magnesium stearate, aliphatic monoester salts of sulfuric acid including, but not limited to, sodium lauryl sulfate; sulfoalkylamides and salts thereof, including, but not limited to, sodium N-methyl-N-oleyltaurate salt; alkylaryl sulfonates including, but not limited to, alkylbenzene sulfonates; alkylnaphthalene sulfonates and salts thereof; and salts of lignosulfonic acid including, but not limited to, sodium diisopropyl naphthalene sulfonate.

[0115] Examples of fillers include insoluble fillers and soluble fillers such as silica, amorphous silica, pyrogenated diatomaceous earth, clay and bentonite.

[0116] Exemplary antifoaming agents include silicones, long-chain alcohols and fatty acid salts.

[0117] Exemplary dyes include, for example, red, blue, and green dyes, and are preferably pigments, which are moderately soluble in water, and dyes, which are soluble in water. Examples are inorganic coloring agents, such as iron oxide, titanium oxide, and iron hexacyanoferrate, and organic coloring agents, such as alizarin, and azo and phthalocyanine coloring agents.

[0118] In one embodiment, the stable herbicide composition comprises (i) about 0.1% w / w about 70% w / w of cyclohexanedione oxime herbicide and (ii) about 0.01% w / w about 60% w / w of a stabilizing system, said stabilizing system comprising about 0.01% w / w about 50% w / w of metal dialkyl sulfosuccinate and about 0.01% w / w about 50% w / w of sorbitan fatty acid ester, each based on the total weight of the stable herbicide composition.

[0119] In one embodiment, the stable herbicidal composition comprises Petition 870260060795, dated 06 / 22 / 2026, p. 30 / 79 20 / 32 (i) about 1% w / w about 50% w / w of cyclohexanedione oxime herbicide and (ii) about 1% w / w about 50% w / w of a stabilizing system, wherein the stabilizing system comprises about 0.5% w / w about 30% w / w of metal dialkyl sulfosuccinate and about 0.5% w / w about 30% w / w of sorbitan fatty acid ester, each based on the total weight of the stable herbicide composition.

[0120] In one embodiment, the stable herbicide composition comprises (i) about 10% w / w about 40% w / w of cyclohexanedione oxime herbicide and (ii) about 1% w / w about 10% w / w of a stabilizing system, wherein the stabilizing system comprises about 0.5% w / w about 30% w / w of metal dialkyl sulfosuccinate and about 0.5% w / w about 30% w / w of sorbitan fatty acid ester, each based on the total weight of the stable herbicide composition.

[0121] In one embodiment, the stable herbicide composition comprises about 1% w / w about 50% w / w, or about 10% w / w about 40% w / w of cyclohexanedione oxime herbicide and 1% w / w about 50% w / w or about 1% w / w about 10% of a stabilizing system, wherein the stabilizing system comprises about 0.5% w / w about 30% w / w of metal dialkyl sulfosuccinate, and about 0.5% w / w about 30% w / w of sorbitan fatty acid ester, each based on the total weight of the stable herbicide composition, and wherein the stable herbicide composition is an emulsifiable concentrate (EC).

[0122] In one embodiment, the present disclosure provides a process for preparing a stable herbicidal composition, wherein the process comprises: providing a stabilizing system comprising a metal dialkyl sulfosuccinate, a nonionic surfactant, a solvent and, optionally, one or more adjuvant ingredients; and Petition 870260060795, dated 06 / 22 / 2026, page 31 / 79 21 / 32 add a cyclohexanedione oxime or an agriculturally acceptable salt thereof to the stabilizing system to provide the stable herbicidal composition, wherein the stabilizing system comprises metal dialkyl sulfosuccinate and sorbitan fatty acid ester in a ratio of 1:10 to 10:1.

[0123] In one embodiment, the stabilizing system comprises metal dialkyl sulfosuccinate and sorbitan fatty acid ester in a ratio of 1:5 to 5:1.

[0124] In one embodiment, the process for preparing the stable herbicide composition additionally includes: a) Mix the solvent, metal dialkyl sulfosuccinate, sorbitan fatty acid ester and, optionally, one or more adjuvant ingredients to form the stabilizing system, and b) add the cyclohexanedione oxime herbicide to the stabilizing system to obtain the stable herbicide composition.

[0125] In one embodiment, the present disclosure provides a process for preparing a stable herbicidal composition, wherein the process comprises: a) mixing a solvent, a metal dialkyl sulfosuccinate, a sorbitan fatty acid ester and, optionally, one or more adjuvant ingredients to form a stabilizing mixture; b) add a cyclohexanedione oxime herbicide to the stabilizing mixture under low shear conditions; and c) Emulsify the mixture under low shear to obtain a stable herbicide composition as an emulsifiable concentrate (EC).

[0126] As used herein, low shear refers to mixing that occurs through non-turbulent flow (e.g., regular or laminar type). For example, low shear conditions are present when the mixing of materials occurs at a low speed and the material particles move in an orderly fashion throughout the mixer without inducing turbulence in the mixture.

[0127] According to one embodiment of the present disclosure, the formation of the stabilizing system by mixing the solvent, metal dialkyl sulfosuccinate and Petition 870260060795, dated 06 / 22 / 2026, page 32 / 79 22 / 32 sorbitan fatty acid ester is carried out under low shear to facilitate emulsification.

[0128] According to one embodiment of the present disclosure, the addition of cyclohexanedione oxime and, optionally, an additional herbicide to the stabilizing system is also carried out under low shear to obtain the final EC composition according to the present invention.

[0129] According to one embodiment of the present disclosure, the mixing and emulsification steps in the process 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.

[0130] According to one embodiment of the present disclosure, the emulsification is carried out for a period of about 30 seconds to about 24 hours; or from about five minutes to about three hours.

[0131] According to one embodiment of the present disclosure, the average particle size of the cyclohexanedione oxime herbicide (e.g., clethodim) is from about 0.01 µm to about 100 µm, or from about 0.01 µm to about 10 µm.

[0132] According to one embodiment of the present disclosure, the operating conditions for producing particles of a desired size will depend on a variety of factors, including, where applicable, the temperature at which the emulsification is carried out, the rate of addition of the components of the stabilizing system, the type of solvent and specific active ingredients, the reagents, the emulsifying equipment used, the amount of emulsifiers used and the like.

[0133] According to an embodiment of the present disclosure, a method of weed control comprises applying an effective amount of a herbicide composition to a weed, a crop, a locus or a habitat area, where the herbicide composition comprises; Petition 870260060795, dated 06 / 22 / 2026, page 33 / 79 23 / 32 at least one cyclohexanedione oxime or an agriculturally acceptable salt thereof; and a stabilizing system comprising a metal dialkyl sulfosuccinate and a nonionic surfactant in a ratio of 1:10 to 10:1.

[0134] According to one embodiment of the present disclosure, the stabilizing system comprises metal dialkyl sulfosuccinate and nonionic surfactant in a ratio of 1:5 to 5:1.

[0135] According to one embodiment of the present disclosure, the stabilizing system comprises metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a ratio of 1:5 to 5:1.

[0136] According to an embodiment of the present disclosure, a method of weed control comprises applying an effective amount of a herbicide composition to a weed, a crop, a locus or a habitat area, where the herbicide composition comprises: (i) clethodim; and (ii) a stabilizing system comprising metal dialkyl sulfosuccinate and sorbitan fatty acid ester in a ratio of 1:10 to 10:1, or in a ratio of 1:5 to 5:1.

[0137] According to an embodiment of the present disclosure, the % recovery of the amount of cyclohexanedione oxime herbicide remaining in the stable herbicide composition of the present disclosure after storing the composition 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) is in the range of 95% to 100%, indicating efficient stability of the composition.

[0138] According to one embodiment of the present disclosure, the % recovery of the amount of active ingredient, i.e., clethodim, remaining in the stable herbicide composition of the present disclosure after storing the composition for a defined period of 14 days under accelerated thermal stability (AHS) conditions (approximately 54 °C) and / or low temperature conditions (e.g., approximately Petition 870260060795, dated 06 / 22 / 2026, page 34 / 79 24 / 32 -10 °C) is in the range of 96% to 99%, thus indicating the efficient stability of the composition.

[0139] In compositions without the nonionic surfactant, the % reduction in the amount of the active ingredient, i.e., clethodim remaining in the stable herbicide composition of the present disclosure after storage of the composition 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) is at least 8%, thus indicating that such compositions are unstable.

[0140] According to one embodiment of the present disclosure, the stable herbicide composition is used to control a wide range of weeds.

[0141] According to an embodiment of the present disclosure, the stable herbicide composition is used to control a broad spectrum of annual and perennial weeds in the pre-emergence and post-emergence stages.

[0142] According to one embodiment of the present disclosure, the stable form of the herbicide composition allows the active compounds to be effectively absorbed by the plants.

[0143] According to one embodiment of the present disclosure, the stable herbicide composition is used as the source of active agrochemical ingredients and will typically be diluted to form end-use formulations, and typically, a spray formulation. The herbicide composition may be diluted with water, from 1 to 10,000, and particularly, from 10 to 1,000 times the total weight of the stable herbicide composition, to form the spray formulation. The stable herbicide composition may be diluted for use to provide an active agrochemical concentration of about 0.5 percent by weight (% by weight) to about 1% by weight. In said diluted composition, the active agrochemical concentration may be in the range of about 0.001% by weight to about 1% by weight of the total formulation when sprayed.

[0144] Spray formulations include all the components that one wishes to apply to plants or their environment. Spray formulations can Petition 870260060795, dated 06 / 22 / 2026, page 35 / 79 25 / 32 can be made by simple dilution of the stable herbicide composition containing active agrochemical ingredients, by mixing the individual active agrochemical ingredients, or by a combination of dilution of a stable herbicide composition and addition of other individual active agrochemical ingredients or mixtures of active agrochemical ingredients. Typically, such end-use mixing is carried out in the tank from which the formulation is sprayed or, alternatively, in a holding tank to fill the spray tank. Such mixing and blending are typically referred to as tank mixing and tank blends.

[0145] According to one embodiment of the present disclosure, a kit comprising a stable agrochemical composition is provided. The kit comprises a plurality of components, including at least one of the ingredients of the stable herbicide composition of the present invention.

[0146] According to one embodiment of the present disclosure, a kit comprises: at least one cyclohexanedione oxime herbicide or an agriculturally acceptable salt thereof; and a stabilizing system comprising a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a ratio of 1:10 to 10:1.

[0147] According to one embodiment of the present disclosure, the kit comprises at least one cyclohexanedione oxime herbicide or an agriculturally acceptable salt thereof; and a stabilizing system comprising metal dialkyl sulfosuccinate and sorbitan fatty acid ester in a ratio of 1:5 to 5:1.

[0148] In one embodiment of the present disclosure, the kit may include at least one, or all, of the components that can be used to prepare the stable herbicide composition. For example, the kit may include the herbicide cyclohexanedione, another herbicide, and a stabilizing system comprising metal dialkyl sulfosuccinate and sorbitan fatty acid esters. One or more of the components may already be combined or pre-formulated. In those embodiments where more than two Petition 870260060795, dated 06 / 22 / 2026, p. 36 / 79 26 / 32 components are supplied in a kit; the components may already be combined and, as such, are packaged in a single container, such as a jar, bottle, can, bag, sack, and / or tube.

[0149] In other embodiments, two or more components of a kit may be packaged separately, i.e., in a non-pre-formulated manner. Thus, a kit may include one or more separate containers, such as vials, cans, bottles, bags, pouches and / or tubes, with each container containing a separate component for the stable herbicide composition.

[0150] In both forms, a component of the kit can be applied separately or together with the additional components or as a component of a combination of the composition according to the invention to prepare the stable herbicide composition according to the invention.

[0151] It will be understood that the descriptive report and examples are illustrative but not limiting of the present disclosure and that other embodiments within the spirit and scope of the invention will be suggested to those skilled in the art. Other embodiments may be practiced which are also within the scope of the present invention. The following examples illustrate the invention, but in no way are intended to limit the scope of the claims. Examples

[0152] The revelation will now be described with reference to the specific examples that follow. Example 1: Preparation of emulsifiable concentrate (EC) of clethodim 120 g / L Table 1 Ingredient Quantity (% w / w) Clethodim 13.09 Methyl ester solvent 48.85 Sodium dioctyl sulfosuccinate 5.00 Polysorbate 80 5.00 Fluid-based aromatic solvent 28.06 TOTAL 100 Petition 870260060795, dated 06 / 22 / 2026, p. 37 / 79 27 / 32

[0153] The materials in Table 1 were used to prepare the herbicide composition of Example 1. In particular, 48.85 g of methyl ester solvent and 28.06 g of an aromatic fluid-based solvent were mixed with a separately prepared stabilizing system obtained by mixing 5 g of sodium dioctyl sulfosuccinate and 5 g of polysorbate 80 under low shear to obtain a mixture. 13.09 g of clethodim were then added to the mixture under low shear to obtain a clear amber liquid as a stable emulsifiable concentrate. Example 2: Preparation of emulsifiable concentrate (EC) of clethodim 120 g / L Table 2 Ingredient Quantity (% w / w) Clethodim 12 Methyl ester solvent 48.85 Sodium dioctyl sulfosuccinate 2.5 Polysorbate 80 2.5 Fluid-based aromatic solvent 34.15 TOTAL 100

[0154] The materials in Table 2 were used to prepare the herbicide composition of Example 2. Clethodim, methyl ester solvent, sodium dioctyl sulfosuccinate, polysorbate 80, and aromatic fluid-based solvent were mixed in the concentrations as shown in Table 2 above, and an EC composition was prepared according to the process of Example 1. Example 3: Preparation of clethodim 120 g / L emulsifiable concentrate (EC). Table 3 Ingredient Quantity (% w / w) Cletodim 12 Methyl ester solvent 48.85 Sodium dioctyl sulfosuccinate 3.75 Petition 870260060795, dated 06 / 22 / 2026, pp. 38 / 79 28 / 32 Polysorbate 80 3.75 Fluid-based aromatic solvent 31.65 TOTAL 100

[0155] The materials in Table 3 were used to prepare the herbicide composition of Example 3. Clethodim, methyl ester solvent, sodium dioctyl sulfosuccinate, polysorbate 80, and aromatic fluid-based solvent were mixed in a given ratio shown in Table 3 above, and an EC composition was prepared according to the process of Example 1. Example 4: Preparation of clethodim 120 g / L emulsifiable concentrate (EC) (comparative example) Table 4 Ingredient Quantity (% w / w) Clethodim 12 Methyl ester solvent 44.8 Sodium dioctyl sulfosuccinate 3.33 Castor oil ethoxylate (40 EO) 6.66 Fluid-based aromatic solvent 33.21 TOTAL 100

[0156] The materials in Table 4 were used to prepare the herbicide composition of Example 4. Clethodim, methyl ester solvent, sodium dioctyl sulfosuccinate, castor oil ethoxylate (40 EO), and the aromatic fluid-based solvent were mixed in a given ratio shown in Table 4, and the EC composition was prepared according to the process of Example 1. Stability of formulations containing clethodim (14-day period) and product stability after dilution.

[0157] The EC compositions from Example 1 to Example 4 were prepared as described above. The stability of clethodim in the EC compositions, as well as the stability of the emulsion after dilution, were studied. Petition 870260060795, dated 06 / 22 / 2026, pp. 39 / 79 29 / 32

[0158] It was found that the EC compositions of Example 1, Example 2 and Example 3 remained quite stable after 0 days of storage under ambient conditions (ambient temperature and relative humidity), i.e., immediately after preparation. These EC compositions were also studied after storage for 14 days under accelerated thermal stability (AHS) conditions (temperature of 54 °C) and under low temperature conditions (at -10 °C). As shown in Table 5, the degradation of clethodim in Examples 1 to 3 was within an acceptable range after storage under both elevated temperature (AHS) and low temperature conditions. However, the EC composition of Example 4 showed greater clethodim degradation (the % change, i.e., the % reduction of clethodim in the composition, was 8.21%), which made the system quite unstable.

[0159] The stability of the emulsion after dilution was also studied at a dilution rate of 2%. The emulsion obtained by diluting the compositions of Example 1, Example 2, and Example 3 remained stable after 1 hour, as well as after 24 hours of dilution, and under storage at room temperature. After 1 hour, the amount of cream formation was the lowest in Examples 1 to 3. In both conditions (1 hour and 24 hours), the amount of cream formation in Example 1 remained under control, i.e., it remained below 1 mL. This infers the high stability of the emulsion in end use. Furthermore, in the composition of Example 4, the amount of cream formation remained under control; however, the composition of Example 4 is not favorable for use due to the higher percentage of clethodim degradation. (Table 5) Table 5 Initial Example, 0 days 14 days (clethodim recovery) Emulsion stability (after dilution) % of IA % of IA at 10 °C % of IA at 54 °C % change 1 hour 24 hours Example 1 13.75 13.69 13.20 -3.6 0.25 ml of cream 0.8 ml of cream Petition 870260060795, dated 06 / 22 / 2026, page 40 / 79 30 / 32 Example 2 N / A 11.82 11.59 -1.9 0.2 ml of cream 2.8 ml of cream Example 3 N / A 11.94 11.49 -3.8 Traces of cream 3 ml of cream Example 4 ND 11.39 10.46 -8.21 0.6 ml of cream 2.8 ml of cream AI: Active ingredient Optimization of the stabilizing system

[0160] To study the effect of various ratios of metal dialkyl sulfosuccinate and sorbitan fatty acid esters in the stabilization system, several compositions (Example 5 to Example 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 when the metal dialkyl sulfosuccinate and sorbitan fatty acid ester of the stabilization system were mixed at a weight ratio of 1:5 to 5:1, the clethodim remained quite stable. Furthermore, the emulsion remained stable when tested after 1 hour as well as at 24 hours (Table 6). Therefore, the stabilization system comprising metal dialkyl sulfosuccinate and sorbitan fatty acid ester was considered effective in terms of conferring stability to the emulsion, as well as preventing clethodim degradation. Table 6 Ingredients (% w / w) Ex. 5 (1:1) Ex. 6 (1:1) Ex. 7 (1:1) Ex. 8 (3:2) Ex. 9 (1:5) Ex. 10 (5:1) Ex. 11 (2:3) Cletodim 13.85 13.85 13.85 13.85 13.85 13.85 13.85 Aromatic solvent based on fluid 27.30 27.30 27.30 27.30 27.30 27.30 27.30 Agent 241621 48.85 48.85 48.85 48.85 48.85 48.85 48.85 Sodium bis(2-ethyl-1-hexyl)sulfosuccinate 5.00 5.00 5.00 6.00 8.33 1.67 4.00 Polysorbate 80 5.00 - - 4.00 1.67 8.33 6.00 Polysorbate 88 - 5.00 - - - - - Petition 870260060795, dated 06 / 22 / 2026, page 41 / 79 31 / 32 Polysorbate 24 - - 5.00 - - - - Clethodim recovery (%), 14 days, in AHS 96.51 97.00 95.21 96.72 96.93 96.11 96.15 Emulsion stability after 1 hour (ml) 0.8 4.0 0.1 1.2 3.0 2.8 2.4 Observations Good clethodim recovery and emulsion stability Good clethodim recovery and moderate emulsion stability Moderate clethodim recovery and good emulsion stability Good clethodim recovery and moderate emulsion stability Good clethodim recovery and moderate emulsion stability Good clethodim recovery and emulsion stability Good clethodim recovery and emulsion stability * Ex. = Example.

[0161] The results clearly showed that clethodim compositions, including a stabilizing system comprising metal dialkyl sulfosuccinate and sorbitan fatty acid ester, are stable. Therefore, a stabilized herbicidal composition including a cyclohexanedione oxime herbicide and a stabilizing system comprising a metal dialkyl sulfosuccinate and a sorbitan fatty acid ester in a weight ratio of 1:5 to 5:1 was advantageously discovered. The stabilizing system successfully stabilized the cyclohexanedione oxime herbicide, i.e., clethodim, in the composition, and also conferred stability to the resulting emulsion after dilution for end use. The present disclosure therefore provides at least the following advantages.

[0162] A stable herbicide composition for the effective control of weeds.

[0163] A stable cyclohexanedione oxime herbicide composition with efficient % recovery of active and emulsion stability after storage.

[0164] The disclosed herbicide composition improves the method of controlling weed growth and solves the problems associated with unsatisfactory herbicide efficiency control due to reduced recovery and emulsion stability observed in cyclohexanedione oxime herbicide compositions. Petition 870260060795, dated 06 / 22 / 2026, page 42 / 79 32 / 32

[0165] Although the present subject matter has been shown and described with reference to its preferred embodiments, it will be understood by those skilled in the art that many alternatives, modifications and variations may be made without departing from its spirit and scope. Consequently, it is intended to encompass all such alternatives, modifications and variations that fall within the spirit and broad scope of the appended claims.

Claims

1. Stable herbicidal composition, characterized by comprising: a cyclohexanedione oxime herbicide which is clethodim; and a stabilizing system comprising sodium dioctyl sulfosuccinate and polyoxyethylene (20) sorbitan monooleate (Polysobate 80) in a ratio of 1:5 to 5:1, wherein the composition is an emulsifiable concentrate.

2. Stable herbicidal composition according to claim 1, characterized in that the stabilizing system comprises sodium dioctyl sulfosuccinate and polyoxyethylene (20) sorbitan monooleate (Polysobate 80) in a 1:2 ratio.

3. Stable herbicidal composition according to claim 1, characterized in that the stabilizing system comprises sodium dioctyl sulfosuccinate and polyoxyethylene (20) sorbitan monooleate (Polysobate 80) in a 2:1 ratio.

4. Stable herbicidal composition according to claim 1, characterized in that the stabilizing system comprises sodium dioctyl sulfosuccinate and polyoxyethylene (20) sorbitan monooleate (Polysobate 80) in a 1:1 ratio.

5. Stable herbicide composition according to claim 1, the composition being characterized by comprising 0.1% w / w 70% w / w of clethodim, and 0.01% w / w 60% w / w of the stabilizing system, based on the total weight of the herbicide composition, the stabilizing system comprising 0.01% w / w 50% w / w of sodium dioctyl sulfosuccinate, and 0.01% w / w 50% w / w of polyoxyethylene (20) sorbitan monooleate (Polysobate 80), based on the total weight of the herbicide composition.

6. Process for preparing the stable herbicide composition as defined in claim 1, the process being characterized by comprising: Petition 870260060795, dated 06 / 22 / 2026, page 6 / 79 2 / 2 providing the stabilizing system comprising sodium dioctyl sulfosuccinate, polyoxyethylene (20) sorbitan monooleate (Polysobate 80), a solvent and, optionally, one or more adjuvant ingredients; and adding clethodim to the stabilizing system to provide the stable herbicide composition, the stabilizing system comprising sodium dioctyl sulfosuccinate and polyoxyethylene (20) sorbitan monooleate (Polysobate 80) in a ratio of 1:5 to 5:

1.

7. Process for preparing the stable herbicide composition according to claim 6, the process being further characterized by comprising: mixing the solvent, sodium dioctyl sulfosuccinate, polyoxyethylene (20) sorbitan monooleate (Polysobate 80) and, optionally, one or more adjuvant ingredients, to form the stabilizing system; adding clethodim to the stabilizing system under low shear; and emulsifying the mixture under low shear to obtain the stable herbicide composition as an emulsifiable concentrate (EC).

8. A method for controlling weeds, characterized by comprising applying an effective amount of a herbicide composition as defined in claim 1 to a weed, a crop, a locus or a habitat area.

9. Weed control method according to claim 8, characterized in that the stabilizing system comprises sodium dioctyl sulfosuccinate and polyoxyethylene (20) sorbitan monooleate (Polysobate 80) in a ratio of 1:5 to 5:1.