Stable cyclohexanedione oxime compositions

Abstract

The present invention relates to stable liquid compositions comprising a cyclohexanedione oxime herbicide (preferably clethodim), a water-miscible organic solvent (preferably an alkylbenzene), and at least one non-ionic surfactant (preferably a mixture of a low HLB surfactant and a high HLB surfactant, or a mixture of a high HLB surfactant and fluroxypyr-meptyl, and uses thereof.

Description

[0001] This application is a divisional application of patent application No. 201980071751.3, entitled "Stable Cyclohexanedione Oxime Composition", filed on September 10, 2019. Patent application No. 201980071751.3 corresponds to international application PCT / IB2019 / 057625, which entered the Chinese national phase on April 28, 2021.

[0002] This application claims priority to U.S. Provisional Application 62 / 731,106, filed September 14, 2018, the entire contents of which are incorporated herein by reference.

[0003] Various publications have been cited in this application. The entire disclosure of these documents is incorporated herein by reference in its entirety to provide a more complete description of the prior art to which this invention pertains. Technical Field

[0004] This invention relates to herbicidal compositions comprising cyclohexanedione oxime herbicides and their uses. Background Technology

[0005] Cyclohexanedione oximes are known to be effective herbicides against various post-emergence grass weeds. Cyclohexanedione oximes are a class of herbicides that inhibit fatty acid synthesis by inhibiting acetyl-CoA carboxylase (ACCase). Cyclohexanedione oximes include, but are not limited to, clethodim, sethoxydim, cycloxydim, alloxydim, tralkoxydim, tepraloxydim, clefoxydim, clefoxyfim, butroxydim, and profoxydim.

[0006] Cyclohexanedione oximes are highly sensitive and rapidly affected by different additives. Due to this sensitivity, the formulation of cyclohexanedione oximes is challenging.

[0007] Cyclohexanedione oximes, such as (5RS)-2{(E)-1-[(2E)-3-chloroallyloxyimino]propyl}-5-[(2RS)-2-(ethylthio)propyl]-3-hydroxycyclohex-2-en-1-one (clethodim), are chemically unstable compounds that rapidly decompose under various conditions, including sunlight, high temperatures, and proton environments. The main decomposition products of clethodim are sulfoxides, sulfones, and oxazol sulfones. Another decomposition product of clethodim is HOCAL-O-(3-chloro-2-propenyl)hydroxylamine.

[0008] Clethodim decomposes rapidly in the composition and also rapidly on the leaf surface due to the formation of hydrochloric acid through acid-catalyzed reaction and photolysis in the presence of water.

[0009] The presence of other active and inactive components in the composition affects the stability of clethodim.

[0010] In the prior art, clethodim is formulated into different compositions containing stabilizers and / or adjuvants.

[0011] US 5084087 discloses an easily dilutable, adjuvant-containing post-emergence weed control composition comprising a mixture of one or more weed control compounds, a polyoxyethylene nonionic surfactant with a hydrophilic-lipophilic balance (HLB) of 10 to about 14, an anionic surfactant selected from dialkyl metal sulfosuccinates and metal alkylbenzene sulfonates, optionally a low-foaming polyoxyethylene nonionic surfactant with an HLB of less than 10, and a lower alkanol ester of a long-chain fatty acid.

[0012] WO2006050141 discloses a herbicidal composition comprising (a) an effective amount of a herbicidal cyclohexanedione oxime compound or an agriculturally acceptable salt or ester thereof; (b) an ester of one or more fatty acids; and (c) one or more nonionic surfactants selected from polyoxyethylene vegetable oils and polyoxyethylene dehydrated sorbitol fatty acid esters. As an additional optional component, one or both of (d) anionic surfactants and (e) hydrocarbon solvents may be used.

[0013] US2006223710 discloses a herbicidal composition containing clethodim, wherein the amount of water is less than 0.2%.

[0014] WO2007050090 discloses a composition comprising clethodim and a mixture of fatty acids, a nonionic surfactant, POE, and animal fat ether sulfate. The composition excludes two specific anionic surfactants.

[0015] WO2011011265 discloses a composition comprising an active herbicide (particularly a cyclohexanedione oxime herbicide), a stabilizer, and an epoxidized compound.

[0016] WO2016196130 discloses a composition comprising a cyclohexanedione oxime compound or an agriculturally acceptable salt thereof, and an effective amount of one or more stabilizing surfactants to provide stability of the cyclohexanedione oxime. The disclosure teaches that nonionic and anionic surfactants must be combined to stabilize the emulsion, and that in this case, the stability of clethodim is reduced.

[0017] CN 101999354 discloses a composition comprising clethodim, fomesafen, a solvent, an emulsifier, a stabilizer, and a synergist, wherein the stabilizer is organobentonite, white carbon, black or light calcium carbonate, and the emulsifier is a nonionic or anionic surface agent.

[0018] Based on the above disclosure, there is a need to develop a stable composition containing clethodim, wherein the degradation rate of clethodim is reduced and the concentration of clethodim is maintained for a longer period of time.

[0019] In recent years, there has been a growing demand for new agrochemical compositions with high performance and low clethodim degradation.

[0020] There is a need to develop compositions with high physical and chemical stability, which exhibit high stability during the preparation, storage and application of the compositions. Summary of the Invention

[0021] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least one nonionic surfactant.

[0022] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least one nonionic surfactant; wherein the composition is substantially free of ionic surfactants.

[0023] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants; wherein the composition is substantially free of ionic surfactants.

[0024] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants; wherein the composition is substantially free of ionic surfactants.

[0025] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least one nonionic polymeric surfactant.

[0026] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least one nonionic polymeric surfactant.

[0027] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least two nonionic surfactants; and (d) at least one surfactant being polymerized.

[0028] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants, wherein at least one of the nonionic surfactants is polymerized.

[0029] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants, provided that the composition comprises less than 2% by weight of an ionic surfactant, based on the total weight of the composition.

[0030] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants, provided that the composition contains less than 2% by weight of an ionic surfactant, based on the total weight of the composition.

[0031] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least two nonionic surfactants; and (d) a polyalkoxylated alkyl ether, provided that the composition contains less than 2% by weight of an ionic surfactant, based on the total weight of the composition.

[0032] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least two nonionic surfactants; and (d) a polyalkoxylated alkyl ether, provided that the composition contains less than 2% by weight of an ionic surfactant, based on the total weight of the composition.

[0033] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least one nonionic surfactant; and (d) a polyalkoxylated alkyl ether, provided that the composition contains less than 2% by weight of an ionic surfactant based on the total weight of the composition.

[0034] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least one nonionic surfactant; and (d) a polyalkoxylated alkyl ether, provided that the composition contains less than 2% by weight of an ionic surfactant based on the total weight of the composition.

[0035] The present invention provides a method for stabilizing a liquid composition comprising a cyclohexanedione oxime compound and a water-miscible organic solvent, the method comprising formulating the composition in the absence of ionic surfactants and in the presence of at least two nonionic surfactants.

[0036] The present invention provides the use of at least one nonionic surfactant for stabilizing liquid compositions comprising clethodim and a poorly water-miscible organic solvent.

[0037] The present invention provides the use of a combination of at least two nonionic surfactants for stabilizing liquid compositions comprising clethodim and a low water miscibility organic solvent.

[0038] The present invention provides a method for physically stabilizing a liquid composition of a cyclohexanedione oxime compound in a water-miscible organic solvent after dilution in the absence of an ionic surfactant, wherein the method comprises formulating the composition to have a high HLB value by using at least one polymeric surfactant having a high HLB value.

[0039] The present invention provides a method for physically stabilizing a liquid composition of a cyclohexanedione oxime compound in a poorly water-miscible organic solvent after dilution in the absence of ionic surfactants, wherein the method comprises formulating the composition to have a high HLB value by using at least two polymerizable surfactants, wherein at least one surfactant has a high HLB value and at least one surfactant has a low HLB value.

[0040] The present invention provides a method for eliminating unwanted plants, comprising the step of contacting the unwanted plant or an area susceptible to the growth of unwanted plants with any of the compositions described herein.

[0041] The present invention also provides a method for controlling weeds, comprising applying any of the stable liquid compositions described herein to weeds, parts of weeds, areas or soil adjacent to weeds, and / or weed seeds, thereby controlling weeds.

[0042] The present invention also provides a method for controlling weeds in plant crops, comprising applying any of the stable liquid compositions described herein to weeds, parts of weeds, areas or soil adjacent to weeds, and / or weed seeds, thereby controlling weeds.

[0043] The present invention also provides a method for preparing any of the stable liquid compositions described herein, wherein the method comprises the following steps: (i) mixing a water-miscible organic solvent with at least one nonionic surfactant; and (ii) Add clethodim to the solution from step (i) and mix until a solution is obtained. Detailed Implementation

[0044] definition Before elaborating on this topic in detail, it will be helpful to provide definitions for certain terms used herein. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this topic pertains. For clarity, the following definitions are provided.

[0045] Unless otherwise expressly stated, the term "a" ("an" or "a kind") as used herein includes both the singular and the plural. Therefore, in this application, the terms "a" or "at least one" are used interchangeably.

[0046] As used herein, when used in conjunction with numerical values, the term "about" includes a range of ±10% of the indicated value. Furthermore, all ranges herein for the same component or performance include endpoints, can be independently combined, and include all intermediate points and ranges. It should be understood that, where a parameter range is provided, the invention also provides all integers within that range and their decimal places. For example, "0.1-80%" includes 0.1%, 0.2%, 0.3%, etc., up to a maximum of 80%.

[0047] As used herein, "substantially free of" means that the composition contains an amount of ionic surfactant that does not significantly affect the physical and chemical stability of the composition, including the physical and chemical stability of the cyclohexanedione oxime compound in the composition. In some embodiments, the composition contains less than 2% by weight of ionic surfactant, based on the total weight of the composition. In a preferred embodiment, the composition contains less than 0.3% by weight of ionic surfactant, based on the total weight of the composition. In a more preferred embodiment, the composition is free of ionic surfactant.

[0048] As used herein, the term “pesticide” broadly refers to any agent that can be used to control and / or kill pests. This term should be understood to include, but is not limited to, fungicides, insecticides, nematicides, herbicides, acaricides, parasiteicides, or other control agents. For information on chemical categories and applications, as well as specific compounds in each category, see “The Pesticide Manual Thirteenth Edition” (British Crop Protection Council, Hampshire, UK, 2003) and “The e-Pesticide Manual, 3rd Edition” (British Crop Protection Council, Hampshire, UK, 2003-04), the contents of which are incorporated herein by reference in their entirety.

[0049] As used herein, the terms "plant" or "crop" include the whole plant, plant organs (e.g., leaves, stems, twigs, roots, trunks, branches, buds, fruits, etc.), plant cells, or plant seeds. The term covers plant crops, if any. In another embodiment, the term "plant" also includes plant propagation material, which may include all reproductive parts of the plant, such as seeds and nutrient plant material, such as cuttings and tubers that can be used for plant propagation. This includes seeds, tubers, spores, corms, bulbs, rhizomes, basal shoots, stolons, and buds, as well as other parts of the plant, including seedlings and young plants that are transplanted after germination or emergence from the soil.

[0050] As used in this article, the term "site" includes not only areas where weeds may have grown, but also areas where weeds have not yet appeared and areas that are being cultivated.

[0051] As used herein, the term “mixture” or “combination” refers to, but is not limited to, any physical combination, such as blends, solutions, alloys, etc.

[0052] As used herein, the term “effective amount” refers to the amount of a mixture that, when ingested, exposed to, or sensed, is sufficient to achieve a good level of protection.

[0053] As used herein, the phrase “agriculturally acceptable salt” means salt that is known and accepted in the art for agricultural or horticultural use.

[0054] As used herein, the term "adjuvant" is broadly defined as any substance that is not itself a herbicide but enhances or is intended to enhance the effectiveness of a herbicide used with it. Adjuvants can be understood to include spreaders, penetrants, compatibilizers, and anti-drift agents.

[0055] As used herein, the term “additive” is defined as any substance that is not itself a herbicide but is added to a composition, such as adhesives, surfactants, synergists, buffers, acidifiers, defoamers, and thickeners.

[0056] As used in this article, the term "stable" refers to chemical and / or physical stability.

[0057] As used herein, when used in conjunction with chemical stability, the term "stable" means that no significant decomposition of the active ingredient in the composition was observed after storage at temperatures up to 30°C for at least one year or after any standard accelerated storage stability test (e.g., storage at 54°C for two weeks). Significant decomposition is defined as degradation greater than 6%.

[0058] As used herein, when used in conjunction with physical stability or with a composition, the term “stable” means that the composition is compatible with emulsion stability tests according to CIPAC standards (e.g., MT 36.3) and produces a cream concentration of 2% or less after 2 hours.

[0059] As used herein, the term "low water miscibility" refers to the poor solubility of water in an organic solvent. When referring to low water solubility in an organic solvent, it means that the solubility of water in the organic solvent is less than 1% by weight at a temperature of 20°C, based on the total amount of solvent, or 1.0 mg / 100 ml. Solvents with solubility less than 0.7 mg / 100 ml are particularly preferred.

[0060] As used herein, "polyalkoxy or polyalkoxylation" refers to polyepoxides. Polyepoxides are C2-C5 hydroxy hydrocarbons, such as ethylene oxide, propylene oxide, and butane oxide.

[0061] Stability testing was conducted according to the CIPAC method.

[0062] As used herein, the term "ionic surfactant" refers to a surfactant having anionic, cationic, or zwitterionic functional groups (such as sulfonic acid, phosphate, and ammonium groups).

[0063] As used herein, the term "bucket mix" means mixing two or more components (including one or more chemical pesticides) or compositions in a spray can during spray application. In some embodiments, the term "bucket mix" means mixing two or more chemical pesticides or compositions in a spray can during spray application.

[0064] As used herein, the term "safener" refers to an agent that increases plant tolerance to herbicides without significantly affecting the effectiveness of the active ingredient.

[0065] As used herein, the term "thickener" refers to an agent that increases the viscosity of a liquid composition without substantially altering other properties of the composition.

[0066] Cyclohexanedione oxime is known as an effective herbicide. Therefore, in this application, the terms "cyclohexanedione oxime herbicide," "cyclohexanedione oxime," and "cyclohexanedione oxime compound" are used interchangeably.

[0067] Cyclohexanedione oxime liquid composition This invention provides a non-aqueous composition comprising cyclohexanedione oxime, wherein the composition is chemically and physically stable. Ionic surfactants are essential for stabilizing non-aqueous compositions after dilution to obtain emulsions. However, the chemical stability of cyclohexanedione oxime is significantly affected by the ionic environment. A novel chemically and physically stable system for cyclohexanedione oxime compositions has been developed. It has been found that compositions comprising cyclohexanedione oxime are chemically and physically stable when ionic surfactants are excluded and at least two nonionic surfactants are added.

[0068] The stability of the composition was tested using the CIPAC method.

[0069] This test is a standard test in the relevant industry before and after storage stability testing (after 2 weeks at 54°C or equivalently after 8 weeks at 40°C).

[0070] Normal storage conditions are two years at room temperature or, under accelerated storage stability testing: after two weeks at 54°C, or equivalently after eight weeks at 40°C, or after twelve weeks at 35°C.

[0071] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least one nonionic surfactant.

[0072] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least one nonionic polymeric surfactant.

[0073] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least one nonionic surfactant, wherein the composition is substantially free of ionic surfactants.

[0074] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants.

[0075] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants; wherein the composition is substantially free of ionic surfactants.

[0076] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants, wherein the composition is substantially free of ionic surfactants.

[0077] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least one nonionic surfactant; and (d) at least one polymerizable surfactant.

[0078] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least one nonionic surfactant; and (d) at least one nonionic polymeric surfactant.

[0079] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least two nonionic surfactants; and (d) at least one surfactant being polymerized.

[0080] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants, wherein at least one of the nonionic surfactants is polymerized.

[0081] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants, provided that the composition comprises less than 2% by weight of an ionic surfactant based on the total weight of the composition.

[0082] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants; provided that the composition contains less than 2% by weight of an ionic surfactant, based on the total weight of the composition.

[0083] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants.

[0084] The present invention provides a liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants.

[0085] In some embodiments, the composition is substantially free of ionic surfactants.

[0086] In some embodiments, the composition comprises at least two nonionic surfactants. In some embodiments, the composition comprises at least three nonionic surfactants. In some embodiments, the composition comprises two nonionic surfactants. In some embodiments, the composition comprises three nonionic surfactants.

[0087] In some embodiments, at least one nonionic surfactant is polymerized. In some embodiments, the composition comprises a polymerized surfactant. In some embodiments, the composition comprises a nonionic polymerized surfactant.

[0088] In some embodiments, at least one nonionic surfactant has a high hydrophilic-lipophilic balance (HLB) value. In some embodiments, the high HLB nonionic surfactant has an HLB value of 9 or higher. In some embodiments, at least two nonionic surfactants have high hydrophilic-lipophilic balance (HLB) values. In some embodiments, the high HLB nonionic surfactant has an HLB value of 9 or higher. In some embodiments, the high HLB nonionic surfactant has an HLB value of 10 or higher. In some embodiments, the high HLB nonionic surfactant has an HLB value of 11 or higher. In some embodiments, the high HLB nonionic surfactant has an HLB value of 12 or higher. In some embodiments, the high HLB nonionic surfactant has an HLB value of 13 or higher. In some embodiments, the high HLB nonionic surfactant has an HLB value of 14 or higher. In some embodiments, the high HLB nonionic surfactant has an HLB value of 15 or higher. In some embodiments, the high HLB nonionic surfactant has an HLB value of 16 or higher.

[0089] In some embodiments, at least one nonionic surfactant has a low HLB content. In some embodiments, the low HLB nonionic surfactant has an HLB of 12 or less. In some embodiments, the low HLB nonionic surfactant has an HLB of 11 or less. In some embodiments, the low HLB nonionic surfactant has an HLB of 10 or less. In some embodiments, the low HLB nonionic surfactant has an HLB of 9 or less. In some embodiments, the low HLB nonionic surfactant has an HLB of 8 or less. In some embodiments, the low HLB nonionic surfactant has an HLB of 7 or less. In some embodiments, the low HLB nonionic surfactant has an HLB of 6 or less.

[0090] In some embodiments, at least one nonionic surfactant has a high HLB of 9 or higher, and at least one nonionic surfactant has a low HLB of 12 or lower, wherein the high HLB nonionic surfactant has a higher HLB than the low HLB nonionic surfactant.

[0091] This invention provides a liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants; wherein: (i) The composition is substantially free of ionic surfactants. (ii) at least one nonionic surfactant is polymerized, and (iii) At least one nonionic surfactant has a high HLB of 9 or higher.

[0092] In some implementations, at least two nonionic surfactants have a high HLB level of 9 or higher.

[0093] This invention provides a liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants; wherein: (i) The composition is substantially free of ionic surfactants. (ii) at least one nonionic surfactant is polymerized, and (iii) At least one nonionic surfactant has a high HLB of 9 or higher, and at least one nonionic surfactant has a low HLB of 12 or lower, wherein the high HLB nonionic surfactant has a higher HLB than the low HLB nonionic surfactant.

[0094] This invention provides a liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants; wherein: (i) The composition is substantially free of ionic surfactants. (ii) at least one nonionic surfactant is polymerized, and (iii) At least one nonionic surfactant has a high HLB, and at least one nonionic surfactant has a low HLB.

[0095] In some embodiments, the composition comprises at least one low-HLB component. In some embodiments, the low-HLB component is a nonionic surfactant. In some embodiments, the low-HLB component is an additional pesticide. In some embodiments, the additional pesticide is a herbicide. In some embodiments, the low-HLB component is an additive. In some embodiments, the low-HLB component is an adjuvant. In some embodiments, the low-HLB component is a stabilizer.

[0096] In some embodiments, the nonionic surfactant with low HLB is partially or completely replaced by other components in the composition.

[0097] In some implementation schemes, the low HLB values ​​are less than 10, less than 9, less than 8, less than 7, and less than 6.

[0098] In some embodiments, the composition comprises at least one high-HLB component. In some embodiments, the high-HLB component is a nonionic surfactant. In some embodiments, the high-HLB component is an additional pesticide. In some embodiments, the additional pesticide is a herbicide. In some embodiments, the high-HLB component is an additive. In some embodiments, the high-HLB component is an adjuvant. In some embodiments, the high-HLB component is a stabilizer.

[0099] In some embodiments, the nonionic surfactant with high HLB content is partially or completely replaced by other components in the composition.

[0100] In some embodiments, the high HLB is greater than 9, greater than 10, greater than 11, greater than 12, greater than 13, greater than 14, greater than 15, or greater than 16.

[0101] In some implementations, the amount of cyclohexanedione oxime compound effectively controls weeds.

[0102] In some implementations, cyclohexanedione oxime compounds refer to neutral derivatives, their agriculturally acceptable salts, or esters.

[0103] In some implementations, the cyclohexanedione oxime compound is clethodim.

[0104] In some embodiments, the composition comprises 50-400 g / L of a cyclohexanedione oxime compound. In some embodiments, the composition comprises 100-400 g / L of a cyclohexanedione oxime compound. In some embodiments, the composition comprises 100-300 g / L of a cyclohexanedione oxime compound. In some embodiments, the composition comprises 100-200 g / L of a cyclohexanedione oxime compound. In some embodiments, the composition comprises about 140 g / L of a cyclohexanedione oxime compound. In some embodiments, the composition comprises 200-300 g / L of a cyclohexanedione oxime compound. In some embodiments, the composition comprises about 240 g / L of a cyclohexanedione oxime compound. In some embodiments, the composition comprises about 400 g / L of a cyclohexanedione oxime compound.

[0105] In some embodiments, the composition comprises about 1% to about 20% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 1% to about 15% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 5% to about 10% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 5% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 6% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 7% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 8% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 9% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 10% by weight of a nonionic surfactant, based on the total weight of the composition.

[0106] In some embodiments, the composition contains less than 2% by weight of an ionic surfactant, based on the total weight of the composition. In some embodiments, the composition contains less than 1.5% by weight of an ionic surfactant, based on the total weight of the composition. In some embodiments, the composition contains less than 1% by weight of an ionic surfactant, based on the total weight of the composition. In some embodiments, the composition contains less than 0.5% by weight of an ionic surfactant, based on the total weight of the composition. In some embodiments, the stable liquid composition is free of ionic surfactants.

[0107] In some embodiments, the composition is stable. In some embodiments, the composition is chemically stable. In some embodiments, the composition is physically stable. In some embodiments, physical stability is evaluated after mixing the composition with water. In some embodiments, physical stability is evaluated after diluting the composition with water. In some embodiments, the diluted composition is physically stable.

[0108] In some embodiments, less than 6% of the cyclohexanedione oxime compound was observed to decompose after storage at 54°C for 14 days. In other embodiments, less than 5% of the cyclohexanedione oxime compound was observed to decompose after storage at 54°C for 14 days.

[0109] In some embodiments, after 2 hours of storage, the composition contains less than 2% cream. In some embodiments, after 2 hours of storage, the composition contains less than 1.5% cream. In some embodiments, after 2 hours of storage, the composition contains less than 1% cream. In some embodiments, after 2 hours of storage, the composition contains less than 0.5% cream.

[0110] In some embodiments, the nonionic surfactant is selected from alkylphenol ethoxylates (NPE and OPE), hydrogenated castor oil ethoxylates (CO-5, CO-16, CO-25, CO-36, CO-40, HCO-16, HCO-25, HCO-36, HCO-40), animal amine ethoxylates (TAM-2, TAM-8, TAM-15, etc.), natural and synthetic alcohol ethoxylates, and C6-C20 alcohol ethoxylates (e.g., Tomadol®, Rhodasurf®, Neodol® 91-2.5, 91-6, 91-8, 23-3, 23-5, 23-7, 23-9, 25-3, 25-5, 25-7, 25-9, 27-3, 27-5, 27-7, 27- 9, 45-7, 45-13, 1-3, 1-5, 1-7, 68-5, 68-20, 68-25, 68-40), alcohol ethoxylate blends, secondary alcohol ethoxylates (e.g., Tergitol™ 15-S series), oleylamine ethoxylates of PEG (polyethylene glycol), cocoamine ethoxylates, stearylamine ethoxylates, polyalkoxylated alkyl ethers, alkylalkoxylated ethers, sorbitol esters, sorbitol ester ethoxylates, polyalkoxylated vegetable oils, castor oil ethoxylates, EO-PO block copolymers / polymers (e.g., Pluronic® L61, L62, L62LF, L64), EO-PO-EO block copolymers / polymers (e.g., Synperonic® PE / L 61, Synperonic® PE / L64), ABA block copolymers / polymers, random copolymers / polymers, star copolymers / polymers, graft copolymers / polymers, modified acrylic and vinyl polymers / polymers, coconut oil fatty acid ethoxylates, oleic acid ethoxylates, stearic acid ethoxylates, tall oil fatty acid ethoxylates, cocamidoyl alcohol monoethanolamine (MEA), cocamidoyl alcohol diethanolamine (DEA), cocamidoyl alcohol monoisopropanolamine (MIPA), ethoxylated tristyrylphenol (e.g., Soprophor® BSU, Soprophor® TS / 54), ethoxylated tristyrylphenol (e.g., Soprophor® 796 / P), ethoxylated fatty alcohols, ethoxylated alkylphenols, polyoxyethylene sorbitan monooleate, polyalkylene glycol ethers, polyalkoxylated sorbitan fatty acid esters, polyoxyethylene polyaryl ethers, polyalkoxylated vegetable oil derivatives, carboxylic amides, monoalkanolamine condensates, polyoxyethylene fatty acid amides, and any combination thereof.

[0111] In some embodiments, the nonionic surfactant is an ethoxylated compound. In some embodiments, the ethoxylated compound is selected from alkylphenol ethoxylated compounds (NPE and OPE), hydrogenated castor oil ethoxylated compounds (CO-5, CO-16, CO-25, CO-36, CO-40, HCO-16, HCO-25, HCO-36, HCO-40), animal amine ethoxylated compounds (TAM-2, TAM-8, TAM-15, etc.), natural and synthetic alcohol ethoxylated compounds, and C6-C20 alcohol ethoxylated compounds (e.g., Tomadol®, Rhodasurf®, Neodol® 91-2.5, 91-6, 91-8, 23-3, 23-5, 23-7, 23-9, 25-3, 25-5, 25-7, 25-9, 27-3, 27-5, 27-7, 27- 9, 45-7, 45-13, 1-3, 1-5, 1-7, 68-5, 68-20, 68-25, 68-40), alcohol ethoxylate blends, secondary alcohol ethoxylates (e.g., Tergitol™ 15-S series), oleylamine ethoxylates of PEG (polyethylene glycol), coconut amine ethoxylates, stearylamine ethoxylates, sorbitol ester ethoxylates, castor oil ethoxylates, EO-PO block copolymers / polymers (e.g., Pluronic® L61, L62, L62LF, L64), EO-PO-EO block copolymers / polymers (e.g., Synperonic® PE / L 61, Synperonic® PE / L 64), coconut oil fatty acid ethoxylates, oleic acid ethoxylates, stearic acid ethoxylates, tall oil fatty acid ethoxylates, ethoxylated tristyrylphenol (e.g., Soprophor®) BSU, Soprophor® TS / 54), ethylpropoxylated tristyrylphenol (e.g., Soprophor® 796 / P), ethylpropoxylated fatty alcohols, ethylpropoxylated alkylphenols, polyoxyethylene sorbitan monooleate, polyalkoxylated sorbitan fatty acid esters, polyoxyethylene polyaryl ethers, polyalkoxylated vegetable oil derivatives, carboxylic amides, monoalkanolamine condensates, polyoxyethylene fatty acid amides, and any combination thereof.

[0112] In some embodiments, the ethoxylated compound contains at least 20 EOs. In some embodiments, the ethoxylated compound contains at least 40 EOs. In some embodiments, the ethoxylated compound contains at least 50 EOs. In some embodiments, the ethoxylated compound contains 54 EOs.

[0113] In some implementations, the ethoxylated compound is ethoxylated castor oil.

[0114] In some embodiments, the polymerized nonionic surfactant is selected from EO-PO block copolymers / polymers, EO-PO-EO block copolymers / polymers, ABA block copolymers / polymers, random copolymers / polymers, star copolymers / polymers, graft copolymers / polymers, modified acrylic and vinyl polymers / polymers, polyalkoxylated alkyl ethers, and any combination thereof.

[0115] In some embodiments, the composition also comprises a polyalkoxylated alkyl ether.

[0116] In some embodiments, the alkyl group is a C1-C6 hydrocarbon chain. In some embodiments, the alkyl group in the polyalkoxylated alkyl ether is a C1-C6 hydrocarbon chain.

[0117] In some embodiments, the polyalkoxylated alkyl ether is a polyalkoxylated butyl ether.

[0118] In some implementations, alkoxylation refers to polyepoxides.

[0119] Polyepoxides may include, but are not limited to, ethylene oxide, propylene oxide, and butane oxide.

[0120] In some embodiments, the alkyl alkoxylated ether comprises a short alkyl chain, such as methyl, ethyl, propyl, or butyl. In some embodiments, the alkyl alkoxylated ether comprises a long alkyl chain, such as a fatty alcohol, including unsaturated and / or branched fatty alcohols.

[0121] In some embodiments, the alkyl alkoxylated ether is an open-chain / free hydroxyl ether. In some embodiments, the alkyl alkoxylated ether is a capped ether. In some embodiments, alkyl refers to a short chain. A short chain refers to C1-C10. Examples of alkyl are methyl or ethyl. In some embodiments, alkyl refers to a long chain. A long chain refers to C10-C30. In some embodiments, the chain is saturated. In some embodiments, the alkyl is unsaturated. In some embodiments, the alkyl is branched.

[0122] End capping refers to the terminating of the terminal hydroxyl groups of certain alkyl alkoxylated ethers of the present invention by alkyl groups (such as methyl, ethyl, benzyl, etc.).

[0123] Polyalkoxylated alkyl ethers refer to polymers and copolymers. Copolymers refer to block copolymers and / or random copolymers.

[0124] In some implementations, alkoxy refers to, but is not limited to, ethylene oxide, propylene oxide, butane oxide, or combinations thereof.

[0125] Examples of polyalkoxylated alkyl ethers are ethoxypropoxybutyl ethers, such as Ethylan. TMNS 500 LQ (sold by Nouryon), Synergen SOC (sold by Clariant), and Brij™ IC20 (sold by Croda). In some embodiments, the polyalkoxylated butyl ether is Ethylan™ NS 500 LQ (sold by Nouryon).

[0126] Polyalkoxylated alkyl ethers may include, but are not limited to, alkoxylated alcohols (e.g., n-butanol polyethylene glycol ether), random copolymers (e.g., ethylene oxide-propylene oxide block copolymers and ethylene oxide-butane block copolymers), block copolymers (e.g., ethylene oxide-propylene oxide block copolymers and ethylene oxide-butane block copolymers); or alkyl-terminated alkoxylated ethers, or combinations thereof.

[0127] In some implementations, the polyalkoxylated vegetable oil is selected from olive oil, kapok oil, castor oil, papaya oil, camellia oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, flaxseed oil, tung oil, sunflower seed oil, safflower oil, and tall oil.

[0128] In some implementations, the fatty acids in the polyalkoxylated sorbitol fatty acid ester are C10-C20.

[0129] In some embodiments, the polyalkoxylated dehydrated sorbitol fatty acid ester is polysorbate 80 (CAS No. 9005-65-6).

[0130] In some implementations, the polyoxyethylene polyaryl ether is ethoxylated tristyrylphenol ether.

[0131] In some embodiments, the polyoxyethylene aryl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene polyoxypropylene tristyrene phenyl ether.

[0132] In some implementations, ethoxylated tristyrylphenol is Soprophor® BSU (sold by Solvay).

[0133] In some implementations, the polyalkoxylated vegetable oil derivative is ethoxylated castor oil.

[0134] In some implementations, the ethoxylated castor oil is Emulsogen® EL 360 (sold by Clariant).

[0135] In some implementations, alkoxylation refers to polyepoxides.

[0136] Polyepoxides may include, but are not limited to, ethylene oxide, propylene oxide, and butane oxide.

[0137] In some embodiments, the nonionic surfactant has an HLB value of 3-16. In some embodiments, the nonionic surfactant has an HLB value of 6-14. In some embodiments, the nonionic surfactant has an HLB value of 9-12.

[0138] In some embodiments, the high-HLB nonionic surfactant has an HLB value greater than 9. In some embodiments, the high-HLB nonionic surfactant has an HLB value greater than 10. In some embodiments, the high-HLB nonionic surfactant has an HLB value greater than 11. In some embodiments, the high-HLB nonionic surfactant has an HLB value greater than 12.

[0139] In some embodiments, the low-HLB nonionic surfactant has an HLB value of less than 12. In some embodiments, the low-HLB nonionic surfactant has an HLB value of less than 11. In some embodiments, the low-HLB nonionic surfactant has an HLB value of less than 10. In some embodiments, the low-HLB nonionic surfactant has an HLB value of less than 9. In some embodiments, the low-HLB nonionic surfactant has an HLB value of less than 8.

[0140] In some embodiments, the high HLB nonionic surfactant is selected from castor oil ethoxylate, ethoxylated tristyrylphenol, ethoxylated tristyrylphenol, sorbitol ester, sorbitol ester ethoxylate, ethoxylated fatty alcohol, ethoxylated alkylphenol, polyalkoxylated butyl ether, polyoxyethylene sorbitol monooleate, and polyalkylene glycol ether.

[0141] In some embodiments, the low HLB nonionic surfactant is selected from ABA block copolymers / polymers, EO-PO block copolymers / polymers, EO-PO-EO block copolymers / polymers, random copolymers / polymers, and star copolymers / polymers.

[0142] In some implementations, the copolymer is a triblock copolymer.

[0143] In some implementations, a triblock copolymer refers to a copolymer of a polyfatty acid and a polyepoxide.

[0144] In some embodiments, the triblock copolymer of polyfatty acid and polyepoxide is a block copolymer of polyethylene glycol and 12-hydroxystearic acid.

[0145] In some embodiments, the block copolymer of polyethylene glycol and 12-hydroxystearic acid is Atlox™ 4912 (sold by Croda).

[0146] In some embodiments, the ABA block copolymer / polymer is based on 12-polyhydroxystearic acid and polyethylene glycol (PEG). In some embodiments, the ABA block copolymer / polymer is Atlox™ 4912 (sold by Croda).

[0147] In some embodiments, the random copolymer / polymer is Atlox™ 4914 (sold by Croda). In some embodiments, the star copolymer / polymer is Atlox™ 4916 (sold by Croda).

[0148] In some implementations, one of the nonionic surfactants is a monomer.

[0149] In some embodiments, the monomeric nonionic surfactant is an ethoxylated sorbitol ester. In some embodiments, the nonionic surfactant is an ethoxylated castor oil.

[0150] In some embodiments, the castor oil ethoxylate is Emulsogen® EL 360 (sold by Clariant). In some embodiments, the castor oil ethoxylate is Agnique® BL 4524 (sold by BASF). In some embodiments, the castor oil ethoxylate is Alkest® CSO 200 (sold by Oxiteno).

[0151] In some implementations, ethoxylated tristyrylphenol is Soprophor® BSU (sold by Solvay).

[0152] In some implementations, ethoxylated tristyrylphenol is Soprophor® 796 / P (sold by Solvay).

[0153] In some embodiments, the polyalkoxylated butyl ether is Ethylan™ NS 500 LQ (sold by Nouryon).

[0154] In some implementations, polyoxyethylene dehydrated sorbitan monooleate is Tween 80.

[0155] In some implementations, the polyalkylene glycol ether is Atlas™ G 5000 (sold by Croda).

[0156] In some embodiments, the composition comprises two nonionic surfactants. In some embodiments, the composition comprises at least three nonionic surfactants. In some embodiments, the composition comprises three nonionic surfactants.

[0157] In some embodiments, the composition comprises Agnique® BL 4524 and Ethylan™ NS 500 LQ.

[0158] In some embodiments, the composition comprises Atlox™ 4912 and Emulsogen® EL 360.

[0159] In some embodiments, the composition comprises Atlox™ 4912 and Soprophor® BSU.

[0160] In some embodiments, the composition comprises Atlox™ 4912 and Atlas™ G 5000.

[0161] In some embodiments, the composition comprises Ethylan™ NS 500 LQ and Alkest® CSO 200.

[0162] In some embodiments, the composition contains less than 1.5% by weight of water, based on the total weight of the composition. In some embodiments, the composition contains less than 1% by weight of water, based on the total weight of the composition. In some embodiments, the composition contains less than 0.5% by weight of water, based on the total weight of the composition. In some embodiments, the composition is substantially water-free. In some embodiments, the composition is water-free.

[0163] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least two nonionic surfactants; and (d) a polyalkoxylated alkyl ether, wherein the composition is substantially free of ionic surfactants.

[0164] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least two nonionic surfactants; and (d) a polyalkoxylated alkyl ether, wherein the composition is substantially free of ionic surfactants.

[0165] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least one nonionic surfactant; and (d) a polyalkoxylated alkyl ether, wherein the composition is substantially free of ionic surfactants.

[0166] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least one nonionic surfactant; and (d) a polyalkoxylated alkyl ether, wherein the composition is substantially free of ionic surfactants.

[0167] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least two nonionic surfactants; and (d) a polyalkoxylated alkyl ether, provided that the composition contains less than 2% by weight of an ionic surfactant based on the total weight of the composition.

[0168] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least two nonionic surfactants; and (d) a polyalkoxylated alkyl ether, provided that the composition contains less than 2% by weight of an ionic surfactant, based on the total weight of the composition.

[0169] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a low water miscibility organic solvent; (c) at least one nonionic surfactant; and (d) a polyalkoxylated alkyl ether, provided that the composition contains less than 2% by weight of an ionic surfactant based on the total weight of the composition.

[0170] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least one nonionic surfactant; and (d) a polyalkoxylated alkyl ether, provided that the composition contains less than 2% by weight of an ionic surfactant based on the total weight of the composition.

[0171] In some implementations, cyclohexanedione oxime compounds refer to their neutral derivatives, agriculturally acceptable salts, or esters.

[0172] In some implementations, the cyclohexanedione oxime compound is clethodim.

[0173] Preferably, the stable liquid composition does not contain ionic surfactants.

[0174] Preferably, the stable liquid composition is chemically and physically stable.

[0175] In some embodiments, the polyalkoxylated alkyl ether is a polyalkoxylated butyl ether.

[0176] In some implementations, alkoxylation refers to polyepoxides.

[0177] Polyepoxides may include, but are not limited to, ethylene oxide, propylene oxide, and butane oxide.

[0178] In some embodiments, the alkyl alkoxylated ether comprises a short alkyl chain, such as methyl, ethyl, propyl, or butyl. In some embodiments, the alkyl alkoxylated ether comprises a long alkyl chain, such as a fatty alcohol, including unsaturated and / or branched fatty alcohols.

[0179] In some embodiments, the alkyl alkoxylated ether is an open-chain / free hydroxyl ether. In some embodiments, the alkyl alkoxylated ether is a capped ether. In some embodiments, alkyl refers to a short chain. A short chain refers to C1-C10. Examples of alkyl are methyl or ethyl. In some embodiments, alkyl refers to a long chain. A long chain refers to C10-C30. In some embodiments, the chain is saturated. In some embodiments, the alkyl is unsaturated. In some embodiments, the alkyl is branched.

[0180] End capping refers to the terminating of the terminal hydroxyl groups of certain alkyl alkoxylated ethers of the present invention by alkyl groups (such as methyl, ethyl, benzyl, etc.).

[0181] Polyalkoxylated alkyl ethers refer to polymers and copolymers. Copolymers refer to block copolymers and / or random copolymers.

[0182] In some implementations, alkoxy refers to, but is not limited to, ethylene oxide, propylene oxide, butane oxide, or combinations thereof.

[0183] Examples of polyalkoxylated alkyl ethers are ethoxypropoxybutyl ethers, such as Ethylan. TM NS 500 LQ, Synergen SOC and Brij™ IC20.

[0184] Polyalkoxylated alkyl ethers may include, but are not limited to, alkoxylated alcohols (e.g., n-butanol polyethylene glycol ether), random copolymers (e.g., ethylene oxide-propylene oxide block copolymers and ethylene oxide-butane block copolymers), block copolymers (e.g., ethylene oxide-propylene oxide block copolymers and ethylene oxide-butane block copolymers); or alkyl-terminated alkoxylated ethers, or combinations thereof.

[0185] In some implementations, nonionic surfactants refer to, but are not limited to, sugar-based surfactants, triblock copolymers, polyalkoxylated vegetable oils, and polyalkoxylated polyaryl ethers.

[0186] In some implementations, nonionic surfactants refer to, but are not limited to, sugar-based surfactants, triblock copolymers, polyalkoxylated vegetable oils, polyalkoxylated polyaryl ethers, and polyalkoxylated alkyl ethers.

[0187] In some implementations, a triblock copolymer refers to a copolymer of a polyfatty acid and a polyepoxide.

[0188] In some implementations, a triblock copolymer refers to a copolymer of a polyfatty acid and a polyepoxide.

[0189] In some embodiments, the triblock copolymer of polyfatty acid and polyepoxide is a block copolymer of polyethylene glycol and 12-hydroxystearic acid.

[0190] In some embodiments, the block copolymer of polyethylene glycol and 12-hydroxystearic acid is Atlox™ 4912.

[0191] In some implementations, the polyalkoxylated vegetable oil is selected from olive oil, kapok oil, castor oil, papaya oil, camellia oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, flaxseed oil, tung oil, sunflower seed oil, safflower oil, and tall oil.

[0192] In some implementations, the fatty acids in the polyalkoxylated sorbitol fatty acid ester are C10-C20.

[0193] In some embodiments, the polyalkoxylated dehydrated sorbitol fatty acid ester is polysorbate 80 (CAS No. 9005-65-6).

[0194] In some implementations, the polyoxyethylene polyaryl ether is ethoxylated tristyrylphenol ether.

[0195] In some embodiments, the polyoxyethylene aryl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene polyoxypropylene tristyrene phenyl ether.

[0196] In some implementations, ethoxylated tristyrylphenol is Soprophor® BSU.

[0197] In some implementations, the polyalkoxylated vegetable oil derivative is ethoxylated castor oil.

[0198] In some implementations, the ethoxylated castor oil is Emulsogen® EL 360.

[0199] In some implementations, alkoxylation refers to polyepoxides.

[0200] Polyepoxides may include, but are not limited to, ethylene oxide, propylene oxide, and butane oxide.

[0201] In some embodiments, at least two nonionic surfactants comprise at least one nonionic surfactant selected from sugar-based surfactants and triblock copolymers, and at least one nonionic surfactant is selected from polyalkoxylated vegetable oils and polyalkoxylated polyaryl ethers.

[0202] In some implementations, the sugar-based surfactant is a polyalkoxylated sorbitol fatty acid ester.

[0203] In some embodiments, the triblock copolymer is a triblock copolymer of a polyfatty acid and a polyepoxide.

[0204] In some implementations, the polyalkoxylated vegetable oil is polyalkoxylated castor oil.

[0205] In some implementations, the polyalkoxylated polyaryl ether is Soprophor BSU.

[0206] In some embodiments, at least one nonionic surfactant is selected from sugar-based surfactants and triblock copolymers, and at least one nonionic surfactant is selected from polyalkoxylated vegetable oils and polyalkoxylated polyaryl ethers.

[0207] In some embodiments, at least one nonionic surfactant is selected from polyalkoxylated sorbitol fatty acid esters and triblock copolymers of polyfatty acids and polyepoxides.

[0208] In some embodiments, at least one nonionic surfactant is selected from polyalkoxylated vegetable oil derivatives and polyalkoxylated polyaryl ethers.

[0209] In some implementations, a triblock copolymer refers to a copolymer of a polyfatty acid and a polyepoxide.

[0210] In some embodiments, the triblock copolymer of polyfatty acid and polyepoxide is a block copolymer of polyethylene glycol and 12-hydroxystearic acid.

[0211] In some embodiments, the block copolymer of polyethylene glycol and 12-hydroxystearic acid is Atlox™ 4912.

[0212] In some implementations, the polyalkoxylated vegetable oil is selected from olive oil, kapok oil, castor oil, papaya oil, camellia oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, flaxseed oil, tung oil, sunflower seed oil, safflower oil, and tall oil.

[0213] In some implementations, the fatty acids in the polyalkoxylated sorbitol fatty acid ester are C10-C20.

[0214] In some embodiments, the polyalkoxylated dehydrated sorbitol fatty acid ester is polysorbate 80 (CAS No. 9005-65-6).

[0215] In some implementations, the polyoxyethylene polyaryl ether is ethoxylated tristyrylphenol ether.

[0216] In some embodiments, the polyoxyethylene aryl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene polyoxypropylene tristyrene phenyl ether.

[0217] In some implementations, ethoxylated tristyrylphenol is Soprophor BSU.

[0218] In some implementations, the polyalkoxylated vegetable oil derivative is ethoxylated castor oil.

[0219] In some implementations, the ethoxylated castor oil is Emulsogen EL 360.

[0220] In some implementations, alkoxylation refers to polyepoxides.

[0221] Polyepoxides may include, but are not limited to, ethylene oxide, propylene oxide, and butane oxide.

[0222] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) a stable system comprising at least two nonionic surfactants, wherein said composition is substantially free of ionic surfactants.

[0223] In some implementations, cyclohexanedione oxime compounds refer to their neutral derivatives, agriculturally acceptable salts, or esters.

[0224] In some implementations, the cyclohexanedione oxime compound is clethodim.

[0225] Preferably, the stable liquid composition does not contain ionic surfactants.

[0226] Preferably, the stable liquid composition is chemically and physically stable.

[0227] In some embodiments, the stabilizing system comprises at least one nonionic surfactant selected from sugar-based surfactants and triblock copolymers, and (2) at least one nonionic surfactant is selected from polyalkoxylated vegetable oils and polyalkoxylated polyaryl ethers.

[0228] In some implementations, the sugar-based surfactant is a polyalkoxylated sorbitol fatty acid ester.

[0229] In some embodiments, the triblock copolymer is a triblock copolymer of a polyfatty acid and a polyepoxide.

[0230] In some implementations, the polyalkoxylated vegetable oil is polyalkoxylated castor oil.

[0231] In some implementations, the polyalkoxylated polyaryl ether is Soprophor® BSU.

[0232] In some embodiments, the nonionic surfactant is selected from sugar-based surfactants and triblock copolymers, and at least one nonionic surfactant is selected from polyalkoxylated vegetable oils and polyalkoxylated polyaryl ethers.

[0233] In some embodiments, at least one nonionic surfactant is selected from polyalkoxylated sorbitol fatty acid esters and triblock copolymers of polyfatty acids and polyepoxides.

[0234] In some embodiments, at least one nonionic surfactant is selected from polyalkoxylated vegetable oil derivatives and polyalkoxylated polyaryl ethers.

[0235] In some implementations, a triblock copolymer refers to a copolymer of a polyfatty acid and a polyepoxide.

[0236] In some embodiments, the triblock copolymer of polyfatty acid and polyepoxide is a block copolymer of polyethylene glycol and 12-hydroxystearic acid.

[0237] In some embodiments, the block copolymer of polyethylene glycol and 12-hydroxystearic acid is Atlox™ 4912.

[0238] In some implementations, the polyalkoxylated vegetable oil is selected from olive oil, kapok oil, castor oil, papaya oil, camellia oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, flaxseed oil, tung oil, sunflower seed oil, safflower oil, and tall oil.

[0239] In some implementations, the fatty acids in the polyalkoxylated sorbitol fatty acid ester are C10-C20.

[0240] In some embodiments, the polyalkoxylated dehydrated sorbitol fatty acid ester is polysorbate 80 (CAS No. 9005-65-6).

[0241] In some implementations, the polyoxyethylene polyaryl ether is ethoxylated tristyrylphenol ether.

[0242] In some embodiments, the polyoxyethylene aryl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene polyoxypropylene tristyrene phenyl ether.

[0243] In some implementations, ethoxylated tristyrylphenol is Soprophor BSU.

[0244] In some implementations, the polyalkoxylated vegetable oil derivative is ethoxylated castor oil.

[0245] In some implementations, the ethoxylated castor oil is Emulsogen® EL 360.

[0246] In some implementations, alkoxylation refers to polyepoxides.

[0247] Polyepoxides may include, but are not limited to, ethylene oxide, propylene oxide, and butane oxide.

[0248] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least one nonionic surfactant; and (d) a polyalkoxylated alkyl ether; wherein the composition is substantially free of ionic surfactants.

[0249] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least one nonionic surfactant; and (d) a polyalkoxylated alkyl ether; wherein the composition is substantially free of ionic surfactants.

[0250] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants; wherein the composition is substantially free of ionic surfactants.

[0251] The present invention provides a stable liquid composition comprising: (a) a certain amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; and (c) at least two nonionic surfactants; wherein the composition is substantially free of ionic surfactants.

[0252] In some implementations, nonionic surfactants refer to, but are not limited to, sugar-based surfactants, triblock copolymers, polyalkoxylated vegetable oils, and polyalkoxylated polyaryl ethers.

[0253] In some embodiments, at least two nonionic surfactants comprise at least one nonionic surfactant selected from sugar-based surfactants and triblock copolymers, and at least one nonionic surfactant is selected from polyalkoxylated vegetable oils and polyalkoxylated polyaryl ethers.

[0254] In some embodiments, the composition further comprises a third nonionic surfactant.

[0255] In some implementations, the third nonionic surfactant may include, but is not limited to, polyalkoxylated alkyl ethers.

[0256] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least one nonionic surfactant selected from polyalkoxylated sorbitol fatty acid esters and triblock copolymers of polyfatty acids and polyepoxides; and (d) at least one nonionic surfactant selected from polyalkoxylated vegetable oil derivatives and polyalkoxylated polyaryl ethers, wherein the composition is substantially free of ionic surfactants.

[0257] The present invention provides a stable liquid composition comprising: (a) an effective amount of a) a cyclohexanedione oxime compound; (b) a low water-soluble organic solvent; (c) a polyalkoxylated dehydrated sorbitol fatty acid ester; and (d) a polyalkoxylated vegetable oil derivative, wherein the composition is substantially free of ionic surfactants.

[0258] In some embodiments, the composition also comprises a polyalkoxylated alkyl ether.

[0259] The present invention provides a stable liquid composition comprising: (a) an effective amount of a) a cyclohexanedione oxime compound; (b) a low water-soluble organic solvent; (c) a polyalkoxylated sorbitol fatty acid ester; and (d) a polyalkoxylated vegetable oil derivative and a polyalkoxylated alkyl ether; wherein the composition is substantially free of ionic surfactants.

[0260] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a low water-soluble organic solvent; (c) a triblock copolymer of a polyfatty acid and a polyepoxide; and (d) a polyalkoxylated vegetable oil derivative, wherein the composition is substantially free of ionic surfactants.

[0261] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a low water-soluble organic solvent; (c) a triblock copolymer of a polyfatty acid and a polyepoxide; and (d) a polyalkoxylated polyaryl ether, wherein the composition is substantially free of ionic surfactants.

[0262] The present invention provides a stable liquid composition comprising: (a) an effective amount of a) a cyclohexanedione oxime compound; (b) a low water-soluble organic solvent; (c) a polyalkoxylated dehydrated sorbitol fatty acid ester; and (d) an alkoxylated vegetable oil, wherein the composition is substantially free of ionic surfactants.

[0263] In some embodiments, the composition also comprises a polyalkoxylated alkyl ether.

[0264] Two nonionic surfactants complement each other to stabilize soluble cyclohexanedione oxime compounds in low water-soluble organic solvents after dilution with water.

[0265] Two nonionic surfactants complement each other to stabilize cyclohexanedione oxime compounds in the oil-in-water composition.

[0266] In some embodiments, the oil-in-water composition is obtained before application to plants.

[0267] In some embodiments, the oil-in-water composition is a concentrated composition.

[0268] In some implementations, the cyclohexanedione oxime compound is clethodim.

[0269] In some implementations, a triblock copolymer refers to a copolymer of a polyfatty acid and a polyepoxide.

[0270] In some embodiments, the triblock copolymer of polyfatty acid and polyepoxide is a block copolymer of polyethylene glycol and 12-hydroxystearic acid.

[0271] In some embodiments, the block copolymer of polyethylene glycol and 12-hydroxystearic acid is Atlox™ 4912.

[0272] In some implementations, the polyalkoxylated vegetable oil is selected from olive oil, kapok oil, castor oil, papaya oil, camellia oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, flaxseed oil, tung oil, sunflower seed oil, safflower oil, and tall oil.

[0273] In some implementations, the fatty acids in the polyalkoxylated sorbitol fatty acid ester are C10-C20.

[0274] In some embodiments, the polyalkoxylated dehydrated sorbitol fatty acid ester is polysorbate 80 (CAS No. 9005-65-6).

[0275] In some implementations, the polyoxyethylene polyaryl ether is ethoxylated tristyrylphenol ether.

[0276] In some embodiments, the polyoxyethylene aryl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene polyoxypropylene tristyrene phenyl ether.

[0277] In some implementations, ethoxylated tristyrylphenol is Soprophor® BSU.

[0278] In some implementations, the polyalkoxylated vegetable oil derivative is ethoxylated castor oil.

[0279] In some implementations, the ethoxylated castor oil is Emulsogen® EL 360.

[0280] In some implementations, alkoxylation refers to polyepoxides.

[0281] Polyepoxides may include, but are not limited to, ethylene oxide, propylene oxide, and butane oxide.

[0282] In some embodiments, the amount of the two nonionic surfactants in the composition is from 1% to 20% by weight, based on the total weight of the composition. In some embodiments, the amount of the two nonionic surfactants in the composition is from 2% to 10% by weight, based on the total weight of the composition. In some embodiments, the amount of the two nonionic surfactants in the composition is from 3% to 7% by weight, based on the total weight of the composition.

[0283] In some embodiments, the composition comprises about 1% to about 20% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 1% to about 15% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 1% to about 10% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 5% to about 10% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 5% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 6% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 7% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 8% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 9% by weight of a nonionic surfactant, based on the total weight of the composition. In some embodiments, the composition comprises about 10% by weight of a nonionic surfactant, based on the total weight of the composition.

[0284] In some embodiments, the weight ratio of the two nonionic surfactants is 9:1 to 1:9; in some embodiments, the weight ratio of the two nonionic surfactants is 7:3; in some embodiments, the weight ratio of the two nonionic surfactants is 6:4; preferably, the weight ratio of the two nonionic surfactants is 1:1.

[0285] In some embodiments, the weight ratio of the two nonionic surfactants is from 9:1 to 1:9. In some embodiments, the weight ratio of the two nonionic surfactants is 7:3. In some embodiments, the weight ratio of the two nonionic surfactants is 6:4, and preferably, the weight ratio of the two nonionic surfactants is 1:1.

[0286] In some embodiments, the amounts of the two nonionic surfactants are 0.5 to 10% by weight, based on the total weight of the composition.

[0287] In some embodiments, the amount of the third nonionic surfactant is 1 to 5% by weight, based on the total weight of the composition.

[0288] In some embodiments, the amount of the stable system in the composition is from about 1% to about 20% by weight, based on the total weight of the composition.

[0289] In some embodiments, the amount of the stable system in the composition is from about 3% to about 20% by weight, based on the total weight of the composition.

[0290] In some embodiments, the amount of the nonionic surfactant in the composition is from 1% to 20% by weight, based on the total weight of the composition. In some embodiments, the amount of the two nonionic surfactants in the composition is from 2% to 10% by weight, based on the total weight of the composition. In some embodiments, the amount of the two nonionic surfactants in the composition is from 3% to 7% by weight, based on the total weight of the composition.

[0291] In some embodiments, the triblock copolymer of polyfatty acid and polyepoxide, ABA triblock, comprises two polyhydroxy stearates and one polyepoxide.

[0292] In some implementations, the triblock copolymer of polyfatty acid and polyepoxide is Atlox™ 4912.

[0293] In some implementations, the two nonionic surfactants are Atlox™ 4912 and Soprophor®.

[0294] In some implementations, the two nonionic surfactants are Atlox™ 4912 and ethoxylated castor oil.

[0295] In some implementations, the two nonionic surfactants are polyalkoxylated sorbitol fatty acid esters and alkoxylated castor oil.

[0296] In some embodiments, the composition also comprises a polyalkoxylated alkyl ether.

[0297] The stability of oil-in-water emulsions is affected by the interaction between surfactants and water molecules to achieve complete and uniform isolation from water.

[0298] The stability of low water miscibility organic solvents in water is affected by the ability of surfactants to cover and encapsulate individual phases and to interact with different phases.

[0299] It has been found that the stability of poorly water-miscible organic solvents containing clethodim in water depends on the arrangement of the hydrophilic and lipophilic groups of the surfactant on the organic and aqueous carriers and their interaction with the carriers, and less on the level of hydrophilicity or lipophilicity (HLB value) of each surfactant. Compositions containing cyclohexanedione oxime compounds have been found to be stable over a wide range of HLB values.

[0300] It has been found that compositions containing cyclohexanedione oxime compounds can be stabilized with a wide range of HLB values. The level of hydrophilicity or lipophilicity has less effect on the stability of the emulsion than the structure and position of the hydrophilic groups on the oil surface.

[0301] In some implementations, the nonionic surfactant has a low HLB value.

[0302] In some embodiments, the nonionic surfactant has a high HLB value. In some embodiments, the two nonionic surfactants in the composition have high HLB values ​​and low HLB values.

[0303] High HLB values ​​refer to, but are not limited to, 12 to 16.

[0304] Low HLB values ​​refer to, but are not limited to, 3 to 6.

[0305] In some embodiments, the nonionic surfactant has a low HLB value of 3 to 6. In some embodiments, the nonionic surfactant has a high HLB value of 12 to 16.

[0306] In some implementations, the nonionic surfactant has a moderate HLB value of 6 to 12.

[0307] It was also found that the compositions of the present invention, which are substantially free of ionic surfactants and contain a combination of at least two nonionic surfactants, are less affected by residual water, and the compositions may contain up to 1.5% by weight of water, based on the total weight of the composition.

[0308] Reducing humidity sensitivity is important for manufacturing processes, packaging, and self-life.

[0309] In some embodiments, the composition contains less than 1.5% by weight of water, based on the total weight of the stable composition.

[0310] The physical stability of the composition was tested using CIPAC methods (e.g., MT 36.3). This test is a standard test in the relevant industry before and after storage stability testing (after 2 weeks at 54°C or equivalently after 8 weeks at 40°C).

[0311] The chemical stability of the composition was tested by HPLC analysis.

[0312] In some implementations, the stability of clethodim refers to degradation of less than 6%, 5%, 4%, 3%, or 2%.

[0313] Normal storage conditions are two years at room temperature or, under accelerated storage stability testing: after two weeks at 54°C, or equivalently after eight weeks at 40°C, or after twelve weeks at 35°C.

[0314] In some implementations, the nonionic surfactant does not include reactive hydroxyl groups.

[0315] In some implementations, the nonionic surfactant includes a nonreactive hydroxyl group.

[0316] The reactive hydroxyl group is a group whose bond dissociation energy is less than 120 Kcal / mol.

[0317] In some implementations, the surfactant does not include weakly dissociated hydrogen bonds.

[0318] In some implementations, the surfactant does not include acidic functional groups.

[0319] Acidic functional groups may include, but are not limited to, carboxylic acids, sulfonic acids, and hydrogen bonds with bond dissociation energies less than 120 kcal / mol.

[0320] Alcohols are acidic alcohols with bond dissociation energies less than 120 kcal / mol.

[0321] In some implementations, the stable liquid composition is substantially free of ionic surfactants.

[0322] In some embodiments, the stable liquid composition does not contain anionic surfactants.

[0323] In some embodiments, the stable liquid composition is chemically stable. In some embodiments, the stable liquid composition is physically stable.

[0324] In some embodiments, the stable composition comprises at least one nonionic surfactant.

[0325] In some embodiments, the stable composition comprises a mixture of at least two nonionic surfactants.

[0326] The two nonionic surfactants are selected from Group I and Group II.

[0327] Group I includes, but is not limited to, polyalkoxylated sorbitol fatty acid esters and triblock copolymers of polyfatty acids and polyepoxides.

[0328] Group II includes, but is not limited to, polyalkoxylated vegetable oil derivatives and polyalkoxylated polyaryl ethers.

[0329] In a preferred embodiment, the nonionic surfactant includes polyalkoxylated vegetable oil and alkoxylated polysorbate.

[0330] In a preferred embodiment, the nonionic surfactant comprises polyalkoxylated vegetable oil and block copolymers having an ABA structure.

[0331] ABA refers to, but is not limited to, block copolymers of polyethylene glycol and 12-hydroxystearic acid, such as Atlox™ 4912.

[0332] In a preferred embodiment, vegetable oil refers to, but is not limited to, castor oil.

[0333] In some embodiments, the nonionic surfactants include, but are not limited to, ethoxylated and / or propoxylated sorbitan esters, block copolymers having an ABA structure, alkoxylated castor oil, block copolymers of ethylene oxide (EO) and propylene oxide (PO), alkyl polysaccharides, alkoxylated alkylamines, and alkylated amines.

[0334] In some embodiments, the ethoxylated and / or propoxylated dehydrated sorbitol fatty acid ester is polysorbate 80.

[0335] In some embodiments, the nonionic surfactant is a mixture of polysorbate 80 and ethoxylated castor oil.

[0336] In some implementations, at least two nonionic surfactants are commercially available as Agnique BL 4524.

[0337] In some embodiments, the composition comprises an ionic surfactant at a concentration of less than 0.3% by weight of the total stable composition. In some embodiments, the composition comprises an ionic surfactant at a concentration of less than 0.2% by weight of the total stable composition.

[0338] Ionic surfactants refer to, but are not limited to, anionic, cationic, amphoteric, polyelectrolytes, and combinations thereof.

[0339] In some embodiments, the composition comprises at least one chemical stabilizer. In some embodiments, the composition comprises at least two chemical stabilizers. In some embodiments, the composition comprises one chemical stabilizer. In some embodiments, the composition comprises two chemical stabilizers.

[0340] In some embodiments, the composition does not contain chemical stabilizers.

[0341] In some implementations, chemical stabilizers are not required.

[0342] In some implementations, the chemical stabilizer is a light stabilizer.

[0343] In some embodiments, the composition does not contain light stabilizers.

[0344] In some embodiments, the composition further comprises at least one chemical stabilizer and at least one light stabilizer.

[0345] In some embodiments, the composition also includes a chemical stabilizer.

[0346] In some embodiments, chemical stabilizers include, but are not limited to, butylated hydroxytoluene; phenolic antioxidants; alkyl hydroxybenzophenone (p-hydroxybenzoate), alkyl salicylate, thymol, propyl gallate, tert-butylhydroquinone, titanium dioxide, hexamethylenetetramine, cysteine, ascorbic acid, citric acid, tetraterpenoids (carotenoids), tocopherol, alkyl hydroxyanisole, triethanolamine, sodium metabisulfite, epoxol® (epoxidized soybean oil methyl ester), and any combination thereof.

[0347] In some embodiments, the chemical stabilizer is butylated hydroxytoluene. In some embodiments, the chemical stabilizer is a phenolic antioxidant. In some embodiments, the chemical stabilizer is alkyl hydroxybenzophenone (p-hydroxybenzoate). In some embodiments, the chemical stabilizer is alkyl salicylate. In some embodiments, the chemical stabilizer is thymol. In some embodiments, the chemical stabilizer is propyl gallate. In some embodiments, the chemical stabilizer is tert-butylhydroquinone. In some embodiments, the chemical stabilizer is titanium dioxide. In some embodiments, the chemical stabilizer is hexamethylenetetramine. In some embodiments, the chemical stabilizer is cysteine. In some embodiments, the chemical stabilizer is ascorbic acid. In some embodiments, the chemical stabilizer is citric acid. In some embodiments, the chemical stabilizer is a tetraterpene (carotenoid). In some embodiments, the chemical stabilizer is tocopherol. In some embodiments, the chemical stabilizer is alkyl hydroxyanisole. In some embodiments, the alkyl hydroxyanisole is butylated hydroxyanisole. In some embodiments, the chemical stabilizer is triethanolamine. In some embodiments, the chemical stabilizer is sodium metabisulfite. In some embodiments, the chemical stabilizer is epoxidized soybean oil methyl ester. In some embodiments, the epoxidized soybean oil methyl ester is Epoxol®.

[0348] In some embodiments, the composition comprises about 0.01 wt% to about 5 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition comprises about 0.01 wt% to about 2 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition comprises about 0.1 wt% to about 1.5 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition comprises about 0.1 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition comprises about 0.2 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition comprises about 0.2 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition comprises about 0.2 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition comprises about 0.5 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition comprises about 0.8 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition comprises about 1 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition comprises about 1.2 wt% of a chemical stabilizer, based on the total weight of the composition. In some embodiments, the composition contains about 1.4% by weight of a chemical stabilizer, based on the total weight of the composition.

[0349] In some implementations, the light stabilizer includes, but is not limited to, butylated hydroxytoluene; phenolic antioxidants; hydroxybenzophenone; and titanium dioxide.

[0350] In some embodiments, the composition also includes additives and / or adjuvants.

[0351] In some embodiments, the amount of water in the composition is equal to or less than 1.5% by weight, 1% by weight, 0.5% by weight, or 0.2% by weight, based on the total weight of the stabilized composition.

[0352] In some embodiments, the water-miscible organic solvent is a nonpolar solvent. In some embodiments, the water-miscible organic solvent is an aromatic hydrocarbon. In some embodiments, the aromatic hydrocarbon is a naphthalene solvent. In some embodiments, the aromatic hydrocarbon is Solvesso™. In some embodiments, the aromatic hydrocarbon is an alkylbenzene solvent. In some embodiments, the alkylbenzene solvent is Solvesso™. In some embodiments, the water-miscible organic solvent is an aromatic solvent. In some embodiments, the aromatic solvent is a naphthalene solvent. In some embodiments, the aromatic solvent is Solvesso™. In some embodiments, the aromatic solvent is an alkylbenzene solvent. In some embodiments, the alkylbenzene solvent is Solvesso™. In some embodiments, the water-miscible organic solvent is a non-aromatic solvent. In some embodiments, the non-aromatic solvent includes aprotic solvents.

[0353] In some implementations, the aprotic solvent includes, but is not limited to, hexane and cyclohexane.

[0354] In some implementation schemes, the low water-soluble organic solvent is selected from aromatic hydrocarbons, paraffin wax, petroleum, diesel oil, mineral oil, and any combination thereof.

[0355] In some embodiments, the water-miscible organic solvent is an aromatic hydrocarbon. In some embodiments, the water-miscible organic solvent may include a combination of at least two solvents. In some embodiments, the water-miscible organic solvent may include a combination of an aromatic hydrocarbon and one or more other water-miscible organic solvents.

[0356] In some embodiments, the aromatic hydrocarbon is selected from toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, isopropylbenzene, tert-butylbenzene, naphthalene, and monoalkyl-substituted or polyalkyl-substituted naphthalene.

[0357] In some embodiments, the aromatic hydrocarbon is a C12 aromatic hydrocarbon. In some embodiments, the aromatic hydrocarbon is an ultra-low naphthalene solvent (ULN). In some embodiments, the aromatic hydrocarbon is a low naphthalene solvent (LN).

[0358] In some embodiments, the aromatic hydrocarbon is Solvesso™ grade from ExxonMobil Chemical, particularly Solvesso™ 100 (CAS No. 64742-95-6), Solvesso™ 150 (CAS No. 64742-94-5), and Solvesso™ 200 (CAS No. 64742-94-5). In some embodiments, the aromatic hydrocarbon is Caromax® 28 LN.

[0359] In some embodiments, the low water-soluble organic solvent is paraffin. In some embodiments, the paraffin is selected from octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, nonadecane, eicosane, dodecane, tridecane, tetradecane, pentadecane and their branched isomers.

[0360] In some embodiments, the composition comprises about 10% to about 80% by weight of a low-water-soluble organic solvent, based on the total weight of the composition. In some embodiments, the composition comprises about 20% to about 70% by weight of a low-water-soluble organic solvent, based on the total weight of the composition. In some embodiments, the composition comprises about 30% to about 60% by weight of a low-water-soluble organic solvent, based on the total weight of the composition. In some embodiments, the composition comprises about 40% to about 50% by weight of a low-water-soluble organic solvent, based on the total weight of the composition. In some embodiments, the composition comprises about 40% by weight of a low-water-soluble organic solvent, based on the total weight of the composition. In some embodiments, the composition comprises about 45% by weight of a low-water-soluble organic solvent, based on the total weight of the composition. In some embodiments, the composition comprises about 50% by weight of a low-water-soluble organic solvent, based on the total weight of the composition. In some embodiments, the composition comprises about 55% by weight of a low-water-soluble organic solvent, based on the total weight of the composition.

[0361] In some embodiments, the water-miscible organic solvent contains less than or equal to 1.5%, 1%, 0.7%, 0.5%, 0.2%, or 0.1% water.

[0362] In some embodiments, the water-miscible organic solvent is a liquid with a water absorption rate of less than or equal to 1.0%, 1%, 0.7%, 0.5%, 0.2%, or 0.1%.

[0363] In some embodiments, the water-miscible organic solvent is a liquid with a water absorption rate of less than or equal to 1 mg per 100 ml or less than or equal to 0.5 mg per 100 ml.

[0364] In some embodiments, the stabilizing composition contains less than or equal to 1.5% or 1% or 0.7% or 0.5% or 0.2% or 0.1% water.

[0365] In some embodiments, the stable composition contains less than or equal to 1 g / L or 0.5 g / L of water.

[0366] In some embodiments, the stable composition is a liquid with a water absorption rate of less than or equal to 1.0%, 0.7%, 0.5%, 0.2%, or 0.1%.

[0367] In some implementations, the dielectric constant of the solvent is less than 10.

[0368] In some implementations, the nonionic surfactant has a stable OH group as an end group.

[0369] In some embodiments, the stable liquid composition is an emulsifiable concentrate, an oil-in-water emulsion, or an oil-in-water emulsion.

[0370] In some embodiments, the amount of the cyclohexanedione oxime compound is 0.1-80% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the cyclohexanedione oxime compound is 0.1-70% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the cyclohexanedione oxime compound is 1-60% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the cyclohexanedione oxime compound is 5-50% by weight, based on the total weight of the stable composition.

[0371] In some embodiments, the amount of the cyclohexanedione oxime compound is 10-20% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the cyclohexanedione oxime compound is 1-15% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the cyclohexanedione oxime compound is about 14% by weight, based on the total weight of the stable composition.

[0372] In some embodiments, the amount of the cyclohexanedione oxime compound is 20-30% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the cyclohexanedione oxime compound is about 24% by weight, based on the total weight of the stable composition.

[0373] In some embodiments, the amount of the cyclohexanedione oxime compound is 40-50% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the cyclohexanedione oxime compound is about 45% by weight, based on the total weight of the stable composition.

[0374] In some embodiments, the amount of cyclohexanedione oxime herbicide is 0.1-80% by weight, based on the total weight of the stable composition. In some embodiments, the amount of cyclohexanedione oxime herbicide is 0.1-70% by weight, based on the total weight of the stable composition. In some embodiments, the amount of cyclohexanedione oxime herbicide is 0.1-60% by weight, based on the total weight of the stable composition. In some embodiments, the amount of cyclohexanedione oxime herbicide is 0.1-40% by weight, based on the total weight of the stable composition. In some embodiments, the amount of cyclohexanedione oxime herbicide is 0.1-25% by weight, based on the total weight of the stable composition. In some embodiments, the amount of cyclohexanedione oxime herbicide is 0.1-1% by weight, based on the total weight of the stable composition. In one specific embodiment, the amount of cyclohexanedione oxime herbicide is about 0.5% by weight, based on the total weight of the stable composition.

[0375] In some embodiments, the concentration of cyclohexanedione oxime in the stabilizing composition is 1 to 50 g / L. In some embodiments, the concentration of cyclohexanedione oxime in the stabilizing composition is 1 to 25 g / L. In some embodiments, the concentration of cyclohexanedione oxime in the stabilizing composition is 1 to 10 g / L. In some embodiments, the concentration of cyclohexanedione oxime in the stabilizing composition is about 5 g / L.

[0376] In some embodiments, the amount of clethodim is 0.1-80% by weight, based on the total weight of the stable composition. In some embodiments, the amount of clethodim is 0.1-70% by weight, based on the total weight of the stable composition. In some embodiments, the amount of clethodim is 1-60% by weight, based on the total weight of the stable composition. In some embodiments, the amount of clethodim is 5-50% by weight, based on the total weight of the stable composition.

[0377] In some embodiments, the amount of clethodim is 1-15% by weight, based on the total weight of the stable composition. In some embodiments, the amount of clethodim is 10-20% by weight, based on the total weight of the stable composition. In some embodiments, the amount of clethodim is about 14% by weight, based on the total weight of the stable composition.

[0378] In some embodiments, the amount of clethodim is 20-30% by weight, based on the total weight of the stable composition. In some embodiments, the amount of clethodim is about 24% by weight, based on the total weight of the stable composition.

[0379] In some embodiments, the amount of clethodim is 40-50% by weight, based on the total weight of the stable composition. In some embodiments, the amount of clethodim is about 45% by weight, based on the total weight of the stable composition.

[0380] In some embodiments, the concentration of clethodim in the stabilizing composition is 50 to 500 g / L. In some embodiments, the concentration of clethodim in the stabilizing composition is 50 to 300 g / L. In some embodiments, the concentration of clethodim in the stabilizing composition is 100 to 200 g / L. In some embodiments, the concentration of clethodim in the stabilizing composition is 100 to 150 g / L. In some embodiments, the concentration of clethodim in the stabilizing composition is about 140 g / L. In some embodiments, the concentration of clethodim in the stabilizing composition is about 240 g / L. In some embodiments, the concentration of clethodim in the stabilizing composition is about 360 g / L. In some embodiments, the concentration of clethodim in the stabilizing composition is about 400 g / L. In some embodiments, the concentration of clethodim in the stabilizing composition is about 430 g / L.

[0381] In some embodiments, the composition further comprises at least one additional pesticide. In some embodiments, the pesticide is a herbicide.

[0382] In some embodiments, the composition also includes at least one other herbicide.

[0383] In some embodiments, the stable composition containing cyclohexanedione oxime is a binary mixture. In some embodiments, the stable composition containing cyclohexanedione oxime is a ternary mixture.

[0384] Herbicides may include, but are not limited to, fluroxypyr, 2-4D, saflufenacil, picloram, amonium glufosinate, and dicamba.

[0385] In some implementations, fluoxetine is fluoxetine ester.

[0386] In some implementations, fluoxetine is a fluoxetine alkyl ester.

[0387] In some implementations, fluroxypyr-meptyl ester is used.

[0388] In some embodiments, the herbicide is fluroxypyr. In some embodiments, the herbicide is isooctyl clopyralid.

[0389] In some embodiments, the amounts of fluroxypyr and clethodim are 0.1-90% by weight, based on the total weight of the stable composition. In some embodiments, the amounts of fluroxypyr and clethodim are 0.5-30% by weight, based on the total weight of the stable composition. In some embodiments, the amounts of fluroxypyr and clethodim are 1-15% by weight, based on the total weight of the stable composition. In some embodiments, the amounts of fluroxypyr and clethodim are 1-10% by weight, based on the total weight of the stable composition. In some embodiments, the amounts of fluroxypyr and clethodim are 3-8% by weight, based on the total weight of the stable composition. In some embodiments, the amounts of fluroxypyr and clethodim are about 15% by weight, based on the total weight of the stable composition.

[0390] In some embodiments, the concentrations of flurbiquat and clethodim in the stabilizing composition are 50 to 500 g / L. In some embodiments, the concentrations of flurbiquat and clethodim in the stabilizing composition are 50 to 300 g / L. In some embodiments, the concentrations of flurbiquat and clethodim in the stabilizing composition are 100 to 200 g / L. In some embodiments, the concentrations of flurbiquat and clethodim in the stabilizing composition are 100 to 150 g / L. In some embodiments, the concentrations of flurbiquat and clethodim in the stabilizing composition are about 132 g / L.

[0391] In some embodiments, the amounts of clopyralid isooctyl ester and clethodim are 0.1-90% by weight, based on the total weight of the stable composition. In some embodiments, the amounts of clopyralid isooctyl ester and clethodim are 0.5-30% by weight, based on the total weight of the stable composition. In some embodiments, the amounts of clopyralid isooctyl ester and clethodim are 1-15% by weight, based on the total weight of the stable composition. In some embodiments, the amounts of clopyralid isooctyl ester and clethodim are 1-10% by weight, based on the total weight of the stable composition. In some embodiments, the amounts of clopyralid isooctyl ester and clethodim are 3-8% by weight, based on the total weight of the stable composition. In some embodiments, the amounts of clopyralid isooctyl ester and clethodim are about 15% by weight, based on the total weight of the stable composition.

[0392] In some embodiments, the concentrations of clopyralid isooctyl ester and clethodim in the stabilizing composition are 50 to 500 g / L. In some embodiments, the concentrations of clopyralid isooctyl ester and clethodim in the stabilizing composition are 50 to 300 g / L. In some embodiments, the concentrations of clopyralid isooctyl ester and clethodim in the stabilizing composition are 100 to 200 g / L. In some embodiments, the concentrations of clopyralid isooctyl ester and clethodim in the stabilizing composition are 100 to 150 g / L. In some embodiments, the concentrations of clopyralid isooctyl ester and clethodim in the stabilizing composition are about 132 g / L.

[0393] In some embodiments, the composition includes an additional herbicide, the type and amount of which can affect the hydrophilic / lipophilic level of the composition, and the hydrophilic / lipophilic level of the composition needs to be adjusted.

[0394] In some embodiments, the hydrophilicity / lipophilicity level of the composition is adjusted by adding additional nonionic surfactants, using nonionic surfactants with different HLBs, and / or changing the concentration ratio between surfactants in the composition.

[0395] In some embodiments, the hydrophilicity / lipophilicity level of the composition is adjusted by adding additional polymeric nonionic surfactants.

[0396] In some implementations, at least two polymerized nonionic surfactants are used.

[0397] In some embodiments, at least two polymerized nonionic surfactants are used to broaden the range of hydrophilic / lipophilic levels of the composition.

[0398] In some embodiments, the additional herbicide has low HLB content, and the composition comprises at least one high HLB nonionic surfactant. In some embodiments, the additional herbicide has low HLB content, and the composition comprises at least two high HLB nonionic surfactants. In some embodiments, the additional herbicide has low HLB content, and none of the nonionic surfactants in the composition have high HLB content.

[0399] In some embodiments, the high-HLB nonionic surfactant has an HLB value greater than 10. In some embodiments, the high-HLB nonionic surfactant has an HLB value greater than 11. In some embodiments, the high-HLB nonionic surfactant has an HLB value greater than 12. In some embodiments, the high-HLB nonionic surfactant has an HLB value greater than 13.

[0400] In some implementations, the additional herbicide is fluroxypyr, specifically isooctyl clopyralid.

[0401] In some embodiments, the composition is mixed with water prior to application. In some embodiments, the composition is mixed with water prior to application to form an emulsion. In some embodiments, the emulsion is stable.

[0402] In some embodiments, the composition comprises an additional pesticide, and said additional pesticide is amphiphilic. In some embodiments, the amphiphilic pesticide is isooctyl clopyralid. In some embodiments, the composition comprises an additional amphiphilic pesticide, and the composition comprises at least one nonionic surfactant with an HLB greater than 9, 10, 11, 12, or 14. In some embodiments, the composition comprises an additional amphiphilic pesticide, and the composition comprises at least two nonionic surfactants each with an HLB greater than 9, 10, 11, 12, or 14. In some embodiments, the composition comprises an additional amphiphilic pesticide, and the composition comprises at least three nonionic surfactants each with an HLB greater than 9, 10, 11, 12, or 14.

[0403] In some embodiments, the amount of the water-miscible organic solvent is 10-90% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the water-miscible organic solvent is 40-80% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the water-miscible organic solvent is 50-60% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the water-miscible organic solvent is 15-50% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the water-miscible organic solvent is 20-40% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the water-miscible organic solvent is 25-40% by weight, based on the total weight of the stable composition. In some embodiments, the amount of the water-miscible organic solvent is 34% by weight, based on the total weight of the stable composition.

[0404] In some embodiments, the concentration of the water-miscible organic solvent in the stabilizing composition is 300-900 g / L. In some embodiments, the concentration of the water-miscible organic solvent in the stabilizing composition is 400-700 g / L. In some embodiments, the concentration of the water-miscible organic solvent in the stabilizing composition is 500-600 g / L. In some embodiments, the concentration of the water-miscible organic solvent in the stabilizing composition is 575-600 g / L.

[0405] In some embodiments, the composition comprises at least one additional surfactant.

[0406] Surfactants may include, but are not limited to, ethoxylated castor oil, polyethoxylated sorbitol, alkoxylated alkylamines, and alkylated amines.

[0407] In some embodiments, the amount of surfactant present in the stabilizing composition is 0.1-40% by weight, based on the total weight of the stabilizing composition. In some embodiments, the amount of surfactant present in the stabilizing composition is 0.1-35% by weight, based on the total weight of the stabilizing composition. In some embodiments, the amount of surfactant present in the stabilizing composition is 0.1-30% by weight, based on the total weight of the stabilizing composition. In some embodiments, the amount of surfactant present in the stabilizing composition is 1-20% by weight, based on the total weight of the stabilizing composition. In some embodiments, the amount of surfactant present in the stabilizing composition is 5-10% by weight, based on the total weight of the stabilizing composition. In some embodiments, the amount of surfactant present in the stabilizing composition is about 7% by weight, based on the total weight of the composition.

[0408] In some embodiments, the composition also includes adjuvants, such as spreading agents, penetrants, compatibilizers, and anti-drift agents.

[0409] In some implementations, the adjuvant is a nonionic compound.

[0410] The adjuvant is selected from alkyl ethoxylated diols, alkyl block alkoxylated diols, alkyl-terminated ethoxylated diols, alkyl-terminated alkyl block alkoxylated diols, ethoxylated alcohols, phosphate esters, ethoxylated tristyrylphenol phosphate esters, sorbitol esters, Tween esters, and combinations thereof.

[0411] In this regard, when nonionic surfactants are used as physical stabilizers, they can also act as adjuvants.

[0412] In some embodiments, the adjuvant is added to the composition either simultaneously or separately in the form of a barrel mix.

[0413] In some embodiments, the adjuvant is present in an amount of at least 10% by weight, based on the total weight of the stable composition. In some embodiments, the adjuvant is present in an amount of at least 15% by weight, based on the total weight of the stable composition. In some embodiments, the adjuvant is present in an amount of at least 20% by weight, based on the total weight of the stable composition. In some embodiments, the adjuvant is present in an amount of at least 30% by weight, based on the total weight of the stable composition.

[0414] In some embodiments, the composition also includes additional additives such as adhesives, thickeners, compatibilizers, buffers, acidifiers, and defoamers.

[0415] Other components may also be added to the compositions of the present invention to increase the stability, density and viscosity of the compositions. These other components may include, for example, adhesives, neutralizers, binders, chelating agents, biocides, stabilizers, buffers, preservatives, antioxidants or antifreeze agents.

[0416] In some embodiments, the composition also includes a safety agent.

[0417] In some embodiments, the safener is selected from mefenpyr diethyl, cloquintocet mexyl, fenchlorazole ethyl, benoxacor, dichlormid, isoxadifen ethyl, and any combination thereof.

[0418] In some embodiments, the safety agent is added to the composition either simultaneously or separately in the form of a barrel mix.

[0419] In some embodiments, the amount of the safer in the stabilizing composition is 0.1-80% by weight, based on the total weight of the stabilizing composition. In some embodiments, the amount of the safer in the stabilizing composition is 1-50% by weight, based on the total weight of the stabilizing composition. In some embodiments, the amount of the safer in the stabilizing composition is 5-25% by weight, based on the total weight of the stabilizing composition. In some embodiments, the amount of the safer in the stabilizing composition is 10-15% by weight, based on the total weight of the stabilizing composition.

[0420] In some implementations, the ratio between the nonionic surfactant and the alkoxylated alkyl ether is 1:1 to 1.5:1.

[0421] In some embodiments, the composition comprises clethodim, Agnique® BL 4524, Ethylan™ NS 500LQ, triethanolamine, and Caromax® 28 LN.

[0422] In some embodiments, the composition comprises clethodim, Agnique® BL 4524, Ethylan™ NS 500LQ, butylated hydroxyanisole, and Caromax® 28 LN.

[0423] In some embodiments, the composition comprises clethodim, Atlox™ 4912, Soprophor® BSU, butylated hydroxyanisole, epoxidized soybean oil methyl ester, and Caromax® 28 LN.

[0424] In some embodiments, the composition comprises clethodim, Atlox™ 4912, Soprophor® BSU, butylated hydroxyanisole, and Caromax® 28 LN.

[0425] In some embodiments, the composition comprises clethodim, Atlox™ 4912, Atlas™ G 5000, epoxidized soybean oil methyl ester, and Solvesso™.

[0426] In some embodiments, the composition comprises clethodim, Atlox 4912™, Soprophor® BSU, epoxidized soybean oil methyl ester, and Caromax® 28 LN.

[0427] In some embodiments, the composition comprises clethodim, Atlox™ 4912, Soprophor® 796 / P, sodium metabisulfite, and Solvesso™.

[0428] In some embodiments, the composition comprises clethodim, Atlox™ 4912, Soprophor® 796 / P, triethanolamine, and Solvesso™.

[0429] In some embodiments, the composition comprises clethodim, Ethylan™ NS 500 LQ, Alkest® CSO200796 / P, triethanolamine, and Solvesso™.

[0430] In some embodiments, the composition comprises clethodim, Ethylan™ NS 500 LQ, Alkest® CSO200796 / P, triethanolamine, and Caromax® 28 LN.

[0431] In some embodiments, the composition comprises a mixture of clethodim, polysorbate 80 (Tween 80) and ethoxylated castor oil, polyalkoxylated butyl ether, triethanolamine and aromatic hydrocarbons.

[0432] In some embodiments, the composition comprises a mixture of clethodim, polysorbate 80 (Tween 80) and ethoxylated castor oil, polyalkoxylated butyl ether, butylated hydroxyanisole, and aromatic hydrocarbons.

[0433] In some embodiments, the composition comprises clethodim, a block copolymer of polyethylene glycol and 12-hydroxystearic acid, ethoxylated tristyrylphenol, butylated hydroxyanisole, epoxidized soybean oil methyl ester, and aromatic hydrocarbons.

[0434] In some embodiments, the composition comprises clethodim, a block copolymer of polyethylene glycol and 12-hydroxystearic acid, ethoxylated tristyrylphenol, butylated hydroxyanisole, and aromatic hydrocarbons.

[0435] In some embodiments, the composition comprises clethodim, a block copolymer of polyethylene glycol and 12-hydroxystearic acid, polyalkylene glycol ether, epoxidized soybean oil methyl ester, and aromatic hydrocarbons.

[0436] In some embodiments, the composition comprises clethodim, a block copolymer of polyethylene glycol and 12-hydroxystearic acid, ethoxylated tristyrylphenol, epoxidized soybean oil methyl ester, and aromatic hydrocarbons.

[0437] In some embodiments, the composition comprises clethodim, a block copolymer of polyethylene glycol and 12-hydroxystearic acid, ethylpropoxylated tristyrylphenol, sodium metabisulfite, and aromatic hydrocarbons.

[0438] In some embodiments, the composition comprises clethodim, a block copolymer of polyethylene glycol and 12-hydroxystearic acid, ethoxylated tristyrylphenol, triethanolamine, and aromatic hydrocarbons.

[0439] In some embodiments, the composition comprises clethodim, polyalkoxylated butyl ether, castor oil ethoxylate, triethanolamine, and aromatic hydrocarbons.

[0440] In some embodiments, the composition comprises clethodim, polyalkoxylated butyl ether, castor oil ethoxylate, triethanolamine, and aromatic hydrocarbons.

[0441] In some embodiments, the composition comprises a certain amount of clethodim, a certain amount of isooctyl clopyralid, and at least one nonionic surfactant. In some embodiments, the composition comprises at least two nonionic surfactants. In some embodiments, the at least one nonionic surfactant is polymerized. In some embodiments, the at least one nonionic surfactant is a polyalkoxylated butyl ether. In some embodiments, the at least one nonionic surfactant is Ethylan™ NS 500 LQ. In some embodiments, the at least one nonionic surfactant is Agnique® BL 4524. In some embodiments, the water-miscible organic solvent is an aromatic solvent. In some embodiments, the water-miscible organic solvent is an alkylbenzene solvent. In some embodiments, the water-miscible organic solvent is Solvesso™. In some embodiments, the amount of clethodim in the composition is about 100 g / L to about 200 g / L, and the amount of isooctyl clopyralid in the composition is about 200 g / L to about 300 g / L. In some embodiments, the amount of clethodim in the composition is from about 130 g / L to about 250 g / L, and the amount of clopyralid isooctyl ester in the composition is from about 280 g / L to about 300 g / L. In some embodiments, the amount of clethodim in the composition is from about 131.6 g / L to about 148.4 g / L, and the amount of clopyralid isooctyl ester in the composition is from about 273.6 g / L to about 302.4 g / L. In some embodiments, the amount of clethodim in the composition is about 240 g / L, and the amount of clopyralid isooctyl ester in the composition is about 288 g / L. In some embodiments, the amount of clethodim in the composition is 240 g / L, and the amount of clopyralid isooctyl ester in the composition is 288 g / L. In some embodiments, the amount of clethodim in the composition is about 10-20% by weight, based on the total weight of the composition. In some embodiments, the amount of clethodim in the composition is about 13-15% by weight, based on the total weight of the composition. In some embodiments, the amount of clethodim in the composition is about 14% by weight, based on the total weight of the composition. In some embodiments, the amount of isooctyl clopyralid in the composition is about 20-30% by weight, based on the total weight of the composition. In some embodiments, the amount of isooctyl clopyralid in the composition is about 18-29% by weight, based on the total weight of the composition. In some embodiments, the amount of isooctyl clopyralid is about 28.8% by weight, based on the total weight of the composition. In some embodiments, the composition contains about 1-5% by weight of Agnique® BL 4524, based on the total weight of the composition. In some embodiments, the composition contains about 2-4% by weight of Agnique® BL 4524, based on the total weight of the composition.In some embodiments, the composition comprises about 3% by weight of Agnique® BL 4524, based on the total weight of the composition. In some embodiments, the composition comprises about 1-5% by weight of Ethylan™ NS 500 LQ, based on the total weight of the composition. In some embodiments, the composition comprises about 3-4% by weight of Ethylan™ NS 500 LQ, based on the total weight of the composition. In some embodiments, the composition comprises about 3.6% by weight of Ethylan™ NS 500 LQ, based on the total weight of the composition. In some embodiments, the composition comprises about 20-30% by weight of Solvesso™ 150, based on the total weight of the composition. In some embodiments, the composition comprises about 20-30% by weight of Solvesso™ 150, based on the total weight of the composition. In some embodiments, the composition comprises about 25-30% by weight of Solvesso™ 150, based on the total weight of the composition. In some embodiments, the composition comprises about 20-30% by weight of Solvesso™ 150, based on the total weight of the composition. In some embodiments, the composition comprises about 25-30% by weight of Solvesso™ 150, based on the total weight of the composition. In some embodiments, the composition comprises about 28% by weight of Solvesso™ 150, based on the total weight of the composition. In some embodiments, the composition is an emulsifiable concentrate (EC) composition. In some embodiments, the pH of the composition is 4-5. In some embodiments, the pH of the composition is 4.5.

[0442] In some embodiments, the stable liquid composition comprises: a) Clethodim, about 24% clethodim; b) about 70% by weight of Solvesso™, based on the total weight of the stabilized composition; c) about 3.5% by weight of Atlox™ 4912, based on the total weight of the composition; and (d) about 3.5% by weight of alkoxylated castor oil or Soprophor® BSU, based on the total weight of the composition, wherein the composition is substantially free of ionic surfactants.

[0443] In one embodiment, the stable liquid composition comprises: a) 10-20% by weight of clethodim, based on the total weight of the stable composition; b) 25-35% by weight of isooctyl clopyralid, based on the total weight of the stable composition; c) 10-90% by weight of a low water-soluble organic solvent, based on the total weight of the stable composition; d) 1-5% by weight of a nonionic surfactant selected from polysorbate 80 and ethoxylated castor oil, based on the total weight of the stable composition; and e) 1-5% by weight of polyalkoxylated alkyl ethers, wherein the composition is substantially free of ionic surfactants.

[0444] In one embodiment, the stable liquid composition comprises: a) 10-20% by weight of clethodim, based on the total weight of the stable composition; b) 25-35% by weight of isooctyl clopyralid, based on the total weight of the stable composition; c) 10-90% by weight of a low water-soluble organic solvent, based on the total weight of the stable composition; d) 1-5% by weight of a nonionic surfactant selected from polysorbate 80 and ethoxylated castor oil, based on the total weight of the stable composition; and e) 1-5% by weight of polyalkoxylated alkyl ethers, wherein the composition is substantially free of ionic surfactants.

[0445] In some embodiments, the stable liquid composition comprises: (a) Approximately 14% by weight of clethodim, based on the total weight of the stable composition; (b) Approximately 28% by weight of fluazinam, based on the total weight of the stable composition; c) Approximately 27% by weight of Solvesso™, based on the total weight of the stabilized composition; d) Approximately 3% by weight of polysorbate 80 and ethoxylated castor oil, based on the total weight of the stable composition; and e) about 3.5% by weight of polyalkoxylated butyl ether, wherein the composition is substantially free of ionic surfactants.

[0446] In some embodiments, the stable liquid composition comprises: (a) Approximately 14% by weight of clethodim, based on the total weight of the stable composition; (b) Approximately 28% by weight of isooctyl clopyralid, based on the total weight of the stable composition; c) Approximately 27% by weight of Solvesso™, based on the total weight of the stabilized composition. d) Approximately 3% by weight of polysorbate 80 and ethoxylated castor oil, based on the total weight of the stable composition; and e) about 3.5% by weight of polyalkoxylated butyl ether, wherein the composition is substantially free of ionic surfactants.

[0447] In some embodiments, the stable liquid composition comprises: (a) Approximately 24% by weight of clethodim, based on the total weight of the stable composition; (b) about 3.5% by weight of a block copolymer of polyethylene glycol and 12-hydroxystearic acid, based on the total weight of the composition; (c) Approximately 3.5% by weight of ethoxylated tristyrylphenol, based on the total weight of the composition; (d) Approximately 69% by weight of Solvesso™, based on the total weight of the composition.

[0448] In some embodiments, the stable liquid composition comprises: (a) Approximately 24% by weight of clethodim, based on the total weight of the stable composition; (b) about 3.5% by weight of a block copolymer of polyethylene glycol and 12-hydroxystearic acid, based on the total weight of the composition; (c) Approximately 3.5% by weight of ethoxylated castor oil, based on the total weight of the composition; (d) Approximately 69% by weight of Solvesso™, based on the total weight of the composition.

[0449] The present invention also provides a stable liquid composition comprising: (a) A certain amount of clethodim, (b) A certain amount of isooctyl clopyralid, (c) Agnique® BL 4524, (d) Ethylan™ NS 500 LQ, and (e) Solvesso™ 150.

[0450] The present invention also provides a stable liquid composition comprising: (a) 140 g / L of clethodim, (b) 288 g / L of clopyralid isooctyl ester, (c) Agnique® BL 4524, (d) Ethylan™ NS 500 LQ, and (e) Solvesso™ 150.

[0451] The present invention also provides a stable liquid composition comprising: (a) 14% by weight of clethodim, (b) 28.8% by weight of isooctyl clopyralid, (c) 3% by weight of Agnique® BL 4524, (f) 3.6% by weight of Ethylan™ NS 500 LQ, and (d) Approximately 28% by weight of Solvesso™ 150.

[0452] In some embodiments, the composition is stable after 7 days of storage. In some embodiments, the composition is stable after 10 days of storage. In some embodiments, the composition is stable after 14 days of storage at 54°C.

[0453] In some embodiments, the composition is stored at a temperature of 25 to 60°C. In some embodiments, the composition is stored at a temperature of 40 to 55°C. In some embodiments, the composition is stored at a temperature of 50 to 55°C. In some embodiments, the composition is stored at a temperature of 54°C.

[0454] In some embodiments, the composition contains greater than 95% clethodim after storage. In some embodiments, the composition contains less than 5% clethodim degradation. In some embodiments, the composition contains less than 1% clethodim degradation. In some embodiments, the composition contains less than 0.5% clethodim degradation. In some embodiments, the composition contains less than 0.1% clethodim degradation. In some embodiments, the composition contains an undetectable amount of clethodim degradation. In some embodiments, the composition does not contain clethodim degradation.

[0455] Furthermore, the agricultural compositions described herein can be used in combination with one or more other pesticides to control a wider range of unwanted pests. When used in combination with other pesticides, the compositions described herein can be formulated with other pesticides, mixed in tanks with other pesticides, or applied sequentially with other pesticides. Additionally, the compositions described herein can optionally be combined with or blended with other pesticide compositions. Such blends with pesticide compositions can be used to control pests in both crop and non-crop environments.

[0456] In some embodiments, the composition is chemically stable. In some embodiments, the composition is physically stable.

[0457] In some embodiments, the pH of the diluted composition is less than 7, 6, 5, 4, 3.5, or 3.

[0458] In some embodiments, the pH of the diluted composition is about 4.5.

[0459] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least one nonionic surfactant; and (d) a polyalkoxylated alkyl ether, wherein the composition is substantially free of ionic surfactants.

[0460] The present invention provides a stable liquid composition comprising: (a) an effective amount of a cyclohexanedione oxime compound; (b) a water-miscible organic solvent; (c) at least one nonionic surfactant; and (d) a polyalkoxylated alkyl ether, provided that the composition contains less than 2% by weight of an ionic surfactant based on the total weight of the composition.

[0461] The present invention also provides packaging comprising any of the compositions disclosed herein.

[0462] Methods to improve the stability of a composition The present invention provides a method for stabilizing a liquid composition comprising a cyclohexanedione oxime compound and a water-miscible organic solvent, wherein the method comprises formulating the composition in the absence of ionic surfactants and in the presence of at least one nonionic surfactant.

[0463] The present invention provides a method for stabilizing a liquid composition comprising a cyclohexanedione oxime compound and a water-miscible organic solvent, wherein the method comprises formulating the composition in the absence of ionic surfactants and in the presence of at least two nonionic surfactants.

[0464] The present invention provides the use of a combination of at least one nonionic surfactant for stabilizing liquid compositions comprising cyclohexanedione oxime compounds and a poorly water-miscible organic solvent.

[0465] This invention provides the use of a combination of at least two nonionic surfactants for stabilizing liquid compositions comprising cyclohexanedione oxime compounds and a poorly water-miscible organic solvent.

[0466] The present invention provides a method for improving the shelf life, stability, herbicidal efficacy, or any combination thereof of a composition comprising a cyclohexanedione oxime compound, the method comprising formulating the composition to be substantially free of ionic surfactants and using at least one nonionic surfactant to physically stabilize the composition.

[0467] The present invention provides a method for improving the shelf life, stability, herbicidal efficacy, or any combination thereof of a composition comprising a cyclohexanedione oxime compound, the method comprising formulating the composition to be substantially free of ionic surfactants and using at least two nonionic surfactants to physically stabilize the composition.

[0468] Methods for improving the chemical stability of cyclohexanedione oxime compounds include reducing the amount of ionic surfactant to equal to or less than 0.2% by weight, based on the total weight of the composition.

[0469] The present invention provides the use of a combination of at least one nonionic surfactant and a polyalkoxylated alkyl ether in a liquid composition containing clethodim for reducing the degradation of clethodim in the liquid composition and stabilizing the liquid composition.

[0470] The present invention provides a method for improving the chemical and physical stability of cyclohexanedione oxime compositions, comprising excluding ionic surfactants from the composition and adding polyalkoxylated alkyl ethers.

[0471] The present invention provides the use of a combination of at least one nonionic surfactant and a polyalkoxylated alkyl ether in a liquid composition containing clethodim for reducing the degradation of clethodim in the liquid composition and stabilizing the liquid composition.

[0472] The present invention provides a method for improving the stability of a clethodim composition, wherein the method comprises adding a certain amount of polymeric nonionic surfactant to the clethodim composition, the amount of which effectively improves the stability of the clethodim composition.

[0473] As used herein, the term "clethodim composition" includes any clethodim composition known in the art and any composition described herein.

[0474] In some implementations, a polymerized nonionic surfactant is added to the tank mix containing clethodim.

[0475] In some embodiments, a polymerized nonionic surfactant is added to the diluted clethodim composition.

[0476] In some embodiments, the method or use includes adding at least one low-HLB component to the composition. In some embodiments, the method or use includes adding at least one high-HLB component to the composition. In some embodiments, the method or use includes adding at least two high-HLB components to the composition.

[0477] The present invention provides a method for physically stabilizing a liquid composition of a cyclohexanedione oxime compound in a poorly water-miscible organic solvent after dilution in the absence of an ionic surfactant, wherein the method comprises formulating the composition to have a high HLB value by using at least one polymeric surfactant having a high HLB value.

[0478] The present invention provides a method for physically stabilizing a liquid composition of a cyclohexanedione oxime compound in a poorly water-miscible organic solvent after dilution in the absence of ionic surfactants, wherein the method comprises formulating the composition to have a high HLB value by using at least two polymerizable surfactants, wherein at least one surfactant has a high HLB value and at least one surfactant has a low HLB value.

[0479] The present invention also provides the use of at least one polymerized surfactant to physically stabilize a liquid composition containing a cyclohexanedione oxime compound in a poorly water-miscible organic solvent after dilution in the absence of an ionic surfactant.

[0480] The present invention also provides a method for improving the physical stability of a liquid composition containing a cyclohexanedione oxime compound in a poorly water-miscible organic solvent after dilution in the absence of an ionic surfactant, wherein the composition contains a high HLB component and / or a surfactant, wherein the method comprises formulating the composition using at least two polymerized surfactants.

[0481] In some implementations, the cyclohexanedione oxime compound is clethodim.

[0482] In some embodiments, one of the two nonionic surfactants is selected from polyalkoxylated sorbitol fatty acid esters and triblock copolymers of polyfatty acids and polyepoxides. The second nonionic surfactant is selected from polyalkoxylated vegetable oil derivatives and polyalkoxylated polyaryl ethers.

[0483] In some embodiments, the triblock copolymer of polyfatty acid and polyepoxide is a block copolymer of polyethylene glycol and 12-hydroxystearic acid.

[0484] In some embodiments, the block copolymer of polyethylene glycol and 12-hydroxystearic acid is Atlox™ 4912.

[0485] In some implementations, the polyalkoxylated vegetable oil is selected from olive oil, kapok oil, castor oil, papaya oil, camellia oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, flaxseed oil, tung oil, sunflower seed oil, safflower oil, and tall oil.

[0486] In some embodiments, the polyalkoxylated sorbitol fatty acid ester has fatty acids of C10-C20.

[0487] In some embodiments, the polyalkoxylated dehydrated sorbitol fatty acid ester is polysorbate 80 (CAS No. 9005-65-6).

[0488] In some implementations, the polyoxyethylene polyaryl ether is ethoxylated tristyrylphenol ether.

[0489] In some embodiments, the polyoxyethylene aryl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene tristyrene phenyl ether. In some embodiments, the polyoxyethylene tristyrene phenyl ether is a polyoxyethylene polyoxypropylene tristyrene phenyl ether.

[0490] In some implementations, ethoxylated tristyrylphenol is Soprophor® BSU.

[0491] In some embodiments, the triblock copolymer of polyfatty acid and polyepoxide is a block copolymer of polyethylene glycol and 12-hydroxystearic acid.

[0492] In some embodiments, the block copolymer of polyethylene glycol and 12-hydroxystearic acid is Atlox™ 4912.

[0493] In some implementations, the vegetable oil is selected from olive oil, kapok oil, castor oil, papaya oil, camellia oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, flaxseed oil, tung oil, sunflower seed oil, safflower oil, and tall oil.

[0494] In some embodiments, the polyalkoxylated dehydrated sorbitol fatty acid ester is polysorbate 80 (CAS No. 9005-65-6).

[0495] In some implementations, the polyalkoxylated vegetable oil derivative is ethoxylated castor oil.

[0496] In some implementations, the ethoxylated castor oil is Emulsogen® EL 360.

[0497] In some implementations, polyalkoxylation refers to polyepoxides.

[0498] Polyepoxides may include, but are not limited to, ethylene oxide, propylene oxide, and butane oxide.

[0499] In some embodiments, the weight ratio of the two nonionic surfactants is 9:1 to 1:9; in some embodiments, the weight ratio of the two nonionic surfactants is 7:3; in some embodiments, the weight ratio of the two nonionic surfactants is 6:4; preferably, the weight ratio of the two nonionic surfactants is 1:1.

[0500] In some embodiments, the weight ratio of the two nonionic surfactants is 9:1 to 1:9; in some embodiments, the weight ratio of the two nonionic surfactants is 7:3. In some embodiments, the weight ratio of the two nonionic surfactants is 6:4, and preferably, the weight ratio of the two nonionic surfactants is 1:1.

[0501] In some embodiments, the amount of at least one nonionic surfactant is 2.5 to 10% by weight, based on the total weight of the composition.

[0502] In some embodiments, the amount of the third nonionic surfactant is 1 to 5% by weight, based on the total weight of the composition.

[0503] In some embodiments, the amount of the stable system in the composition is from about 5% to about 20% by weight, based on the total weight of the composition.

[0504] In some implementations, cyclohexanedione oxime compounds refer to their neutral derivatives, agriculturally acceptable salts, or esters.

[0505] In some embodiments, the triblock copolymer of polyfatty acid and polyepoxide, ABA, comprises two polyhydroxystearates and one polyepoxide (ABA).

[0506] In some implementations, the triblock copolymer of polyfatty acid and polyepoxide is Atlox® 4912.

[0507] In some implementations, the two nonionic surfactants are Atlox™ 4912 and Soprophor® BSU.

[0508] In some implementations, the two nonionic surfactants are Atlox™ 4912 and ethoxylated castor oil.

[0509] In some implementations, the two nonionic surfactants are polyalkoxylated sorbitol fatty acid esters and alkoxylated castor oil.

[0510] In some embodiments, the composition also comprises a polyalkoxylated alkyl ether.

[0511] In some embodiments, the composition includes an additional herbicide, the type and amount of which can affect the hydrophilic / lipophilic level of the composition, and the hydrophilic / lipophilic level of the composition needs to be adjusted.

[0512] In some embodiments, the method includes adjusting the hydrophilicity / lipophilicity level of the composition.

[0513] In some embodiments, the hydrophilicity / lipophilicity level of the composition is adjusted by adding additional nonionic surfactants, using nonionic surfactants with different HLBs, and / or changing the concentration ratio between surfactants in the composition.

[0514] In some implementations, the hydrophilicity / lipophilicity level can be adjusted by adding additional additives and / or additional active ingredients.

[0515] In some implementations, the hydrophilicity / lipophilicity level can be adjusted in the drum mix.

[0516] In some implementations, one or more nonionic polymeric surfactants are added to the tank mix.

[0517] This article describes the method of using the composition. The compositions described herein are suitable for weed control.

[0518] The present invention provides a method for eliminating plants, comprising the step of contacting the plant or an area susceptible to plant growth with any of the compositions described herein.

[0519] The present invention also provides a method for controlling weeds, comprising: applying any of the compositions described herein to weeds, parts of weeds, areas adjacent to weeds or soil and / or weed seeds, thereby controlling weeds.

[0520] The present invention also provides a method for controlling and / or preventing weeds, comprising applying any of the compositions described herein to weeds, portions of weeds, areas or soil adjacent to weeds, cultivation sites and / or sites where weeds are to be prevented, thereby controlling and / or preventing weeds.

[0521] The present invention also provides a method for increasing plant yield by preventing and / or controlling weeds, wherein the method comprises applying any of the compositions described herein to weeds, parts of weeds, areas or soil adjacent to weeds, cultivation sites and / or sites where weeds are to be prevented and / or controlled, thereby increasing plant yield by preventing and / or controlling weeds.

[0522] In some implementation schemes, the plant is the crop.

[0523] In some embodiments, the composition is diluted in water prior to application. In some embodiments, the diluted composition does not exhibit significant phase separation.

[0524] In some embodiments, the composition is applied by foliar spraying. In some embodiments, the composition is applied using a mounted or towed tractor and spraying equipment. In some embodiments, the composition is applied using an aircraft. In some embodiments, the composition is applied using a helicopter. In some embodiments, the composition is applied using a fixed-wing aircraft. In some embodiments, the composition is applied using a rotary-wing aircraft.

[0525] In some embodiments, the composition is applied at a rate of about 0.6 L / ha to about 1.4 L / ha. In some embodiments, the composition is applied at a rate of about 0.8 L / ha to about 1.2 L / ha. In some embodiments, the composition is applied at a rate of about 1 L / ha.

[0526] In some embodiments, the composition is applied before planting. In some embodiments, the composition is applied at least once, from 21 days prior to planting until just before planting. In some embodiments, the composition is applied after planting. In some embodiments, the composition is applied before emergence. In some embodiments, the composition is applied after emergence. In some embodiments, the composition is applied to pre-planting burndown. Pre-planting burndown is carried out after harvest and before new crop planting.

[0527] In some implementation schemes, the weed is goosegrass (Eleusine indica). Eleusine indica ), Crataegus pinnatifida ( Digitaria insularis ), Bidens genus ( Bidens spp ), Amaranth ( Amaranthus spp ), genus *Pseudobulbus* ( Conyza spp ), Volunteer corn and / or large-flowered sweet potatoes ( Ipomaea grandiflora ).

[0528] This article describes a method for preparing the composition. The present invention also provides a method for controlling weeds, comprising: a) Obtain any of the compositions disclosed herein in a water-miscible organic solvent.

[0529] b) Optional dilution with water c) Apply the composition to weeds, parts of weeds, areas or soil adjacent to weeds, and / or weed seeds to control weeds.

[0530] The method involves adding the composition described herein to a carrier (e.g., water) and using the resulting solution containing the herbicidal organic composition for spray application to control weeds or their plant propagation material in crop or non-crop environments. An emulsion can be formed by diluting the stable liquid composition in water.

[0531] The effective application rate of a herbicidal composition cannot be defined in general terms because it varies depending on various conditions, such as the type of pesticide, the target pest, weather conditions, soil properties, and crop type.

[0532] In one embodiment, the application rate of the stable liquid composition is typically from about 1 to about 5 L / ha. In a preferred embodiment, the application rate of the stable liquid composition is from about 2 to 3 L / ha. In a specific embodiment, the application rate of the stable liquid composition is about 2 L / ha. In another specific embodiment, the application rate of the stable liquid composition is about 3 L / ha. In yet another specific embodiment, the application rate of the stable liquid composition is about 2.5 L / ha.

[0533] In one embodiment, the stable liquid composition may be diluted in a carrier (e.g., water) in an amount of about 1 to 100 L of stable composition per 1000 L of water. In another embodiment, the stable liquid composition may be diluted in a carrier (e.g., water) in an amount of about 1 to 30 L of stable composition per 1000 L of water. In yet another embodiment, the stable liquid composition may be diluted in a carrier (e.g., water) in an amount of about 5 to 15 L of stable composition per 1000 L of water.

[0534] In some implementations, the crop is broadleaf.

[0535] In some implementations, the crop may include, but is not limited to, soybeans, wheat, barley, rye, sugar beets, legumes, and oats.

[0536] In another implementation, the weeds may include, but are not limited to, crabgrass ( Digitaria insularis ), goosegrass ( Eleusine indica ), fragrant grass ( Conyza bonariensis ), small turfgrass ( Conyza canadenses ), Sumatran white wine grass ( Conyza sumatrensis ), thorngrass ( Bidens pilosa ), Round-leaved dayflower ( Commelina benghalensis ), white bract orangutan grass ( Euphorbia heterophylla ), broadleaf floribunda ( Spermacoce latifó lia ), ipegen ( Carapichea ipecacuanha ).

[0537] The stable liquid composition described herein can be mixed with water and / or fertilizer and can be applied to the desired location by any means (e.g., aircraft spray cans, backpack spray cans, cattle dipping vats, agricultural equipment for ground spraying (e.g., boom sprayers, hand sprayers, etc.)). The desired location can be soil, plants, etc.

[0538] The stable liquid compositions of the present invention may include additional crop protectants, such as insecticides, herbicides, fungicides, bactericides, nematicides, molluscicides, growth regulators, biological agents, fertilizers, or mixtures thereof. When used in combination with additional crop protectants, the composition may be formulated with these adjuvants, mixed with these adjuvants, or applied sequentially with these adjuvants.

[0539] Method for preparing the compositions described herein This invention provides a method for preparing any of the compositions described herein, wherein the method comprises the following steps: (i) Mixing a water-miscible organic solvent with at least one nonionic surfactant, and (ii) Add clethodim to the solution from step (i) and mix the resulting blend until a solution is obtained.

[0540] The method may also include adding at least one alkyl polyalkoxylated ether to step (i).

[0541] The method may also include step (iii): filtering the solution from step (ii) to obtain a stable liquid composition.

[0542] In some implementations, the method may also include the use of additional nonionic surfactants.

[0543] In some implementations, the additional nonionic surfactant is an alkyl polyalkoxylated ether.

[0544] In some implementations, step (i) includes adding at least one additional herbicide.

[0545] In some implementations, step (ii) includes adding at least one additional herbicide.

[0546] In some embodiments, the additional herbicide is isooctyl clopyralid.

[0547] This invention provides a method for preparing a stable liquid composition comprising an effective amount of clethodim and an effective amount of at least one other herbicide, wherein the method comprises the following steps: (i) Dissolve at least one nonionic surfactant and a herbicidal active ingredient (other than cyclohexanedione oxime) in a low water miscibility organic solvent to obtain a solution.

[0548] (ii) Add cyclohexanedione oxime herbicide to the solution from step (i); and optionally (iii) Filter the solution from step (ii) to obtain a stable liquid composition.

[0549] This invention provides a method for preparing a stable liquid composition comprising an effective amount of clethodim and an effective amount of at least one other herbicide, wherein the method comprises the following steps: (ii) Dissolve at least one nonionic surfactant and a herbicidal active ingredient (other than cyclohexanedione oxime) in a water-miscible organic solvent to obtain a solution. (ii) Add a cyclohexanedione oxime compound to the solution from step (i); and optionally (iii) Filter the solution from step (ii) to obtain a stable liquid composition.

[0550] In some implementations, a water-miscible organic solvent is added during step (ii).

[0551] In some embodiments, at least one alkyl polyalkoxylated ether is further added to step (i).

[0552] In some embodiments, the method further includes adding at least one surfactant and / or auxiliary agent to the solution of step (i) prior to step (ii). In some embodiments, the method further includes adding at least one surfactant and / or auxiliary agent to the solution of step (ii) prior to step (iii).

[0553] In some embodiments, the method further includes adding a thickener to the suspension of step (ii) prior to step (iii).

[0554] In some embodiments, the method further includes the step of adding a safer to the solution of step (i) prior to step (ii).

[0555] In some embodiments, a water-miscible organic solvent is heated to completely dissolve clethodim and / or nonionic surfactants and / or alkyl polyalkoxy polymers and / or isooctyl clopyralid and / or any other cyclohexanedione oxime herbicide and / or any additives in the composition.

[0556] In some embodiments, a water-miscible organic solvent is heated to completely dissolve clethodim and / or nonionic surfactants and / or alkyl polyalkoxy polymers and / or isooctyl clopyralid and / or any other cyclohexanedione oxime herbicide and / or any additives in the composition.

[0557] In some embodiments, a water-miscible organic solvent is heated to completely dissolve clethodim and / or nonionic surfactants and / or alkyl polyalkoxy polymers and / or isooctyl clopyralid and / or any other cyclohexanedione oxime compounds and / or any additives in the composition.

[0558] In some embodiments, a water-miscible organic solvent is heated to completely dissolve clethodim and / or nonionic surfactants and / or alkyl polyalkoxy polymers and / or isooctyl clopyralid and / or cyclohexanedione oxime compounds and / or any additives in the composition.

[0559] Additives may include, but are not limited to, safety agents and adjuvants.

[0560] In some embodiments, step (i) is performed at a temperature between 15°C and 65°C. In some embodiments, step (i) is performed at a temperature of about 20°C, 30°C, 40°C, 50°C, or 60°C.

[0561] With respect to the foregoing embodiments, it is anticipated that the embodiments disclosed herein are applicable to other disclosed embodiments. Furthermore, the elements described in the composition embodiments may be used in the methods, uses, and method embodiments described herein.

[0562] The invention will be better understood by referring to the experimental section below, but those skilled in the art will readily understand that the detailed experiments are merely a more detailed description of the invention as described in the appended claims.

[0563] Experiment and Results Section Formulating stable compositions containing clethodim is particularly challenging because clethodim is very sensitive and decomposes rapidly.

[0564] Clethodim is known to be unstable in ionic environments. However, attempts to formulate physically and chemically stable compositions containing clethodim in non-aqueous liquid compositions have repeatedly failed.

[0565] General method for preparing clethodim compositions (Examples 1-3) A solution is obtained by mixing an aromatic hydrocarbon solvent, at least two nonionic surfactants, and clethodim.

[0566] Example 1: The chemically and physically stable composition of the present invention composition: After being stored at 54°C for two weeks, the concentration of clethodim was greater than 95%.

[0567] The water content is 0.4 g / kg.

[0568] This is an example of a surfactant system comprising a combination of a polymeric nonionic surfactant with a low HLB value and a nonionic surfactant with a high HLB value.

[0569] Example 2. Chemically and physically stable compositions of the present invention composition: After being stored at 54°C for two weeks, the concentration of clethodim was greater than 95%.

[0570] The water content is 0.4 g / kg.

[0571] This is another embodiment of a surfactant system, which is a combination of polymeric nonionic surfactants with low HLB values ​​and nonionic surfactants with high HLB values.

[0572] Example 3. Clethodim 240 EC Composition Table 1 Specification: After being stored at 54°C for two weeks, the concentration of clethodim was greater than 95%.

[0573] The water content is up to 0.4% by weight.

[0574] This is an example of a surfactant system that is a combination of two polymerized nonionic surfactants, one of which has a low HLB value and the other has a high HLB value.

[0575] Example 4: The stable composition of the present invention comprising clethodim and fluroxypyr. Clethodim 140 + Clopyralid isooctyl ester 288 EC composition : Clopyralid equivalent: 200.0 g / L Agnique® BL 4524 is a surfactant mixture of Montanox™ 80 (polysorbate 80, two-way 80, HLB=15) and ethoxylated castor oil. Example 9 shows that the combination of 54 moles of ethoxylated castor oil (EO, HLB=14) and polysorbate 80 effectively mimics the function of Agnique® BL 4524 in the system.

[0576] Specification: Mix in drums on-site according to the main recommended dosage.

[0577] Preparation method for 1000 liters: Aromatic hydrocarbons (Solvesso™ 150), a blend of nonionic surfactants (Agnique® BL 4524), a block copolymer (Ethylan® NS 500 LQ), and molten isooctyl clopyralid were mixed. Clethodim was added, and the resulting mixture was stirred until completely dissolved. The resulting solution was filtered using a 25-micron filter.

[0578] Remark: The product is stable at 54ºC (14 days).

[0579] Gracilitrile degradation: 4.13 wt% Degradation of clopyralid isooctyl ester: 0.03 wt% This is an example involving a surfactant system, which is a combination of a polymeric nonionic surfactant with a high HLB value and two other nonionic surfactants also with high HLB values. This is to balance the large amount of isooctyl clopyralid, a highly hydrophobic amphiphilic surfactant, which acts as a low-HLB surfactant in the system.

[0580] Comparison of experiments and results Typically, the degradation of clethodim is found to be associated with ionic surfactants, and unstable emulsions are associated with the lack of ionic surfactants. Combining at least two nonionic surfactants can yield chemically and physically stable compositions.

[0581] Different comparative tests were conducted, including testing (1) the effect of HLB value on the physical stability of the composition without ionic surfactant, (2) the effect of stabilizer on chemical stability in the presence of ionic surfactant, and (3) the effect of adding other components that affect the HLB of the composition.

[0582] Example 5. Physically unstable composition Clethodim 240 EC Table 2 Compositions containing only a high-HLB nonionic surfactant and lacking a second nonionic surfactant with a lower HLB were tested. The compositions were found to be physically unstable, and an oil phase was obtained.

[0583] Example 6. The application of clethodim in a composition containing an ionic surfactant and further containing an additional stabilizer. Learning stability Table 3 Table 3 shows a set of experiments conducted to test the effect of chemical stabilizers on the degradation of clethodim in the presence of anionic surfactants.

[0584] General method for preparing a 1000 ml formulation: Mix 467 g of a solution of 30% clethodim in Solvesso™ 150 with 411.5 g of 98% clopyralid isooctyl ester; add 43 g of calcium dodecylbenzenesulfonate (anionic surfactant), 110 g of ethoxylated tristyrylphenol 16EO, and 50 g of castor oil 40EO. Mix the resulting mixture until completely dissolved.

[0585] The composition was mixed with different stabilizers (1 to 7 at 2000 ppm) and the degradation of clethodim was measured.

[0586] The degradation rate of clethodim after aging was found to be higher than 5%. The results indicate that, in the presence of ionic surfactants, stabilizers are insufficient to prevent clethodim degradation.

[0587] In the same table (compositions 9 to 12), it can be seen that when different ionic surfactants (calcium dodecylbenzenesulfonate) are replaced using the above method, the degradation remains above 5%, and there are no significant changes between different ionic surfactants.

[0588] Examples 7-8: Compositions of clethodim and fluroxypyr (30 wt%), which are free of ionic surfactants and contain... Combination of alkoxylated castor oil and alkoxylated alkyl ethers Table 4 Chemical and physical stability were tested, and clethodim was found to be chemically stable; however, the composition was found to be physically untestable according to CIPAC standards. Fluroxapyr meptyl affects the hydrophilic / lipophilic level of the composition. Adjustment of the hydrophilic / lipophilic level is necessary, optionally using a third nonionic surfactant with a higher HLB value.

[0589] Example 9. The use of different ethoxylated castor beans in a composition containing clethodim and fluroxypyr. Oil was used to compare the physical stability of the compositions. Tests were conducted using different ethoxylated castor oils in compositions containing clethodim and fluazinam to compare the physical stability of the compositions. The purpose of these tests was to determine the relationship between the degree of ethoxylation of the ethoxylated castor oil used and the physical stability of the composition.

[0590] Formulations 1-4 and STD have the same composition except for the nonionic surfactants used. Formulations 1-4 each contain 1.5% polysorbate 80 (Tween 80) and 1.5% ethoxylated castor oil with varying degrees of ethoxylation, as shown in Table 5. Formulation STD contains 3% Agnique® BL 4524, sold by BASF. Agnique® BL 4524 is a mixture of polysorbate 80 (Tween 80) and ethoxylated castor oil, but the ratio of polysorbate 80 (Tween 80) to ethoxylated castor oil and the degree of ethoxylation of the ethoxylated castor oil are unknown.

[0591] Table 5 Specification: After 2 hours, the percentage of cream remaining is < 1%.

[0592] As the degree of ethoxylation of castor oil increases, the stability of the emulsion increases proportionally. The % results for the cream in STD (Agnique® BL4524) are similar to those using 54% castor oil EO.

[0593] The HLB of a solvent combination can be affected by the presence of amphiphilic articulators (AIs) (composed of hydrophilic and hydrophobic moieties), such as isooctyl clopyralid. The HLB combination needs to be adjusted based on the solvents and AIs used in the formulation. For example, isooctyl clopyralid acts as a low-HLB compound, and a surfactant with a higher HLB is required to balance the formulation.

[0594] Example 10. Testing chemical stability and water content The chemical stability of the composition of Example 4 was tested in the water concentration range.

[0595] Table 6 shows that the compositions disclosed herein are stable despite increased water content.

[0596] Table 6 in conclusion The test results clearly demonstrate that compositions containing clethodim are stable in low water miscibility organic solvents without ionic surfactants in the presence of a combination of at least two nonionic surfactants, and that HLB combinations need to be adjusted according to the type (polymeric or nonpolymeric) of the solvent, AI, and surfactant used in the formulation.

[0597] Although the subject matter has been shown and described with reference to preferred embodiments, those skilled in the art will understand that many alternatives, modifications and variations may be made therein without departing from its spirit and scope. Therefore, it is intended to cover all such alternatives, modifications and variations that fall within the spirit and broad scope of the appended claims.

[0598] All publications, patents and patent applications mentioned in this specification are incorporated herein by reference to the extent that each individual publication, patent or patent application is specifically and individually cited and incorporated herein by reference.

Claims

1. A physically stable liquid composition comprising a. 50 g / L to 500 g / L of clethodim; b. 10-90% by weight of a water-miscible organic aromatic solvent, based on the total weight of the stable composition; c. A stable system comprising 1% to approximately 20% of at least two nonionic surfactants: a certain amount of at least one high-HLB nonionic surfactant having an HLB value of 12 or higher; and a certain amount of at least one low-HLB nonionic surfactant having an HLB value of 3-6; and optionally 1 to 5% by weight of a third nonionic surfactant, based on the total weight of the composition, wherein the term "about" indicates ±10% of the indicated value; and d. A certain amount of water, selected from... i. Up to 1.5% by weight, based on the total weight of the composition; ii. Equal to or less than 1.5% by weight or 1.0% by weight or 0.5% by weight or 0.2% by weight, based on the total weight of the stable composition; iii. Less than or equal to 1.5% by weight, 1% by weight, or 0.7% by weight, or 0.5% by weight, or 0.2% by weight, or 0.1% by weight, based on the total weight of the stable composition; and iv. Less than or equal to 1 g / L, or 5 g / L; The clethodim and nonionic surfactant are completely soluble in a water-miscible organic solvent, with water solubility in the organic solvent being less than 1% by weight at 20°C, or 1.0 mg / 100 ml based on the total amount of solvent; wherein the amounts of the high-HLB nonionic surfactant and the low-HLB nonionic surfactant are sufficient to physically stabilize the liquid composition containing the stated amount of clethodim, wherein clethodim is chemically stable in the composition, i.e., after storage at 54°C for 14 days, less than 6% decomposition of clethodim is observed, thus eliminating the need for the addition of a chemical stabilizer, and wherein the liquid composition is physically stable according to the emulsion stability test of CIPAC standard MT36.3, producing an emulsion concentration equal to or less than 2% after 2 hours. The composition contains less than 2% by weight of an ionic surfactant based on the total weight of the composition, and is free of isooctyl clopyralid, and is free of chemical stabilizers.

2. The physically stable liquid composition according to claim 1, wherein the composition is a herbicidal composition comprising at least one compound, which is a nonionic adjuvant, a triblock copolymer of a polyfatty acid and a polyepoxide as a nonionic surfactant, and optionally a certain amount of another pesticide, wherein the liquid composition is free of ionic surfactants and is free of isooctyl clopyralid, such that the other pesticide is not isooctyl clopyralid, and wherein the triblock copolymer of the polyfatty acid and the polyepoxide is a block copolymer of polyethylene glycol and 12-hydroxystearic acid.

3. The physically stable liquid composition according to claim 1, wherein: a. At least one of the nonionic surfactants is polymerized. b. At least one of the following nonionic surfactants selected from alkylphenol ethoxylates, hydrogenated castor oil ethoxylates, animal lipamine ethoxylates, natural and synthetic alcohol ethoxylates, oleylamine ethoxylates of PEG (polyethylene glycol), cocoamine ethoxylates, stearylamine ethoxylates, polyalkoxylated alkyl ethers, alkylalkoxylated ethers, sorbitol esters, sorbitol ester ethoxylates, polyalkoxylated vegetable oils, castor oil ethoxylates, EO-PO block copolymers / polymers, EO-PO-EO block copolymers / polymers, ABA block copolymers / polymers, random copolymers / polymers, star copolymers / polymers, graft copolymers / polymers, and modified propylene. Acids and vinyl polymers / copolymers, coconut oil fatty acid ethoxylates, oleic acid ethoxylates, stearic acid ethoxylates, tall oil fatty acid ethoxylates, cocamidoyl alcohol monoethanolamine (MEA), cocamidoyl diethanolamine (DEA), cocamidoyl isopropanolamine (MIPA), ethoxylated tristyrylphenol, ethoxylated tristyrylphenol, ethoxylated fatty alcohols, ethoxylated alkylphenols, polyoxyethylene sorbitan monooleate, polyalkylene glycol ethers, polyalkoxylated sorbitan fatty acid esters, polyoxyethylene polyaryl ethers, polyalkoxylated vegetable oil derivatives, carboxylic amides, monoalkanolamine condensates, polyoxyethylene fatty acid amides, and any combination thereof. c. At least one of the nonionic surfactants is a polymerized nonionic surfactant, wherein the polymerized nonionic surfactant is selected from EO-PO block copolymers / polymers, EO-PO-EO block copolymers / polymers, ABA block copolymers / polymers, random copolymers / polymers, star copolymers / polymers, graft copolymers / polymers, polyalkoxylated alkyl ethers, and any combination thereof. d. The high HLB nonionic surfactant is selected from castor oil ethoxylate, ethoxylated tristyrylphenol, ethoxylated tristyrylphenol, sorbitan ester, sorbitan ester ethoxylate, ethoxylated fatty alcohol, ethoxylated alkylphenol, polyalkoxylated butyl ether, polyoxyethylene sorbitan monooleate, and polyalkylene glycol ether. e. Low HLB nonionic surfactants are selected from ABA block copolymers / polymers, EO-PO block copolymers / polymers, EO-PO-EO block copolymers / polymers, random copolymers / polymers, and star copolymers / polymers. f. One type of nonionic surfactant is an ethoxylated compound. g. One type of nonionic surfactant is a monomer. h. One type of nonionic surfactant is a triblock copolymer of polyfatty acid and polyepoxide. i. One type of nonionic surfactant is polyalkoxylated dehydrated sorbitol fatty acid ester. j. One of the nonionic surfactants is a polyalkoxylated vegetable oil derivative, and / or k. One type of nonionic surfactant is a polyalkoxylated polyaryl ether.

4. The physically stable liquid composition according to claim 1, wherein at least one of the nonionic surfactants is selected from C6-C20 alcohol ethoxylates, alcohol ethoxylate blends, and secondary alcohol ethoxylates.

5. The physically stable liquid composition according to claim 3, wherein: a. Ethoxylated compounds contain at least 20 EOs. b. The monomeric nonionic surfactant is an ethoxylated dehydrated sorbitol ester or an ethoxylated castor oil. c. The polyalkoxylated dehydrated sorbitol fatty acid ester is polysorbate 80. d. The polyalkoxylated vegetable oil derivative is alkoxylated castor oil. e. The polyalkoxylated polyaryl ether is ethoxylated tristyrylphenol, and / or f. Triblock copolymers of polyfatty acids and polyepoxides are block copolymers of polyethylene glycol and 12-hydroxystearic acid.

6. The physically stable liquid composition according to claim 3, wherein the ethoxylated compound contains at least 40 EO atoms.

7. The physically stable liquid composition according to claim 6, wherein the ethoxylated compound contains at least 50 EO atoms.

8. The physically stable liquid composition according to claim 1, wherein the composition comprises a nonionic surfactant selected from polyalkoxylated sorbitol fatty acid esters and triblock copolymers of polyfatty acids and polyepoxides, and a nonionic surfactant selected from polyalkoxylated vegetable oil derivatives and polyalkoxylated polyaryl ethers.

9. The physically stable liquid composition according to claim 1, wherein the composition comprises: a. A block copolymer of polyethylene glycol and 12-hydroxystearic acid and ethoxylated castor oil, b. A block copolymer of polyethylene glycol and 12-hydroxystearic acid and ethoxylated tristyrylphenol, or c. Polyalkoxylated dehydrated sorbitol fatty acid esters and alkoxylated castor oil, d. A light stabilizer, and / or a safener selected from pyrazosulfuron, quinalazine, oxadiazon, acetamiprid, fenproxil fumarate, bispyribac-sodium, and any combination thereof. e. Block copolymers of clethodim, polyethylene glycol, and 12-hydroxystearic acid; ethoxylated tristyrylphenol and / or ethoxylated castor oil; and alkylbenzene solvents, The dielectric constant of the low water miscibility organic solvent is less than 10, and / or the low water miscibility organic aromatic solvent includes alkylbenzene solvent.

10. The physically stable liquid composition according to claim 1, wherein the liquid composition is a. An emulsifiable concentrate liquid composition having a water absorption rate of less than or equal to 1.0%, or 0.7%, or 0.5%, or 0.2% or 0.1%, wherein after storage at 54°C for 14 days, decomposition of clethodim is observed to be no more than 6%, or b. An oil-in-water emulsion or a water-in-oil emulsion, formed when the emulsifiable concentrate liquid composition is mixed with water prior to application, wherein, according to CIPAC standard MT 36.3, the emulsifiable concentrate, oil-in-water emulsion, or water-in-oil emulsion produces a cream concentration equal to or less than 2% after 2 hours of storage at 54°C for 2 weeks and / or after storage at 40°C for 8 weeks.

11. The physically stable liquid composition according to claim 1, wherein the composition comprises: I. a. Approximately 24% by weight of clethodim, based on the total weight of the composition; b. Approximately 3.5% by weight of a block copolymer of polyethylene glycol and 12-hydroxystearic acid, based on the total weight of the composition; c. Approximately 3.5% by weight of ethoxylated tristyrylphenol, based on the total weight of the composition; and d. Approximately 69% by weight of alkylbenzene solvent, based on the total weight of the composition, or II. a. Approximately 24% by weight of clethodim, based on the total weight of the composition; b. Approximately 3.5% by weight of a block copolymer of polyethylene glycol and 12-hydroxystearic acid, based on the total weight of the composition; c. Approximately 3.5% by weight of ethoxylated castor oil, based on the total weight of the composition; and d. Approximately 69% by weight of alkylbenzene solvent, based on the total weight of the composition. The physically stable liquid composition contains less than 1.5% by weight of water, based on the total weight of the composition, and the term "about" means ±10% of the indicated value.

12. The physically stable liquid composition according to claim 1, wherein the composition comprises: Two nonionic surfactants, polyalkoxylated dehydrated sorbitol fatty acid esters and alkoxylated castor oil, and further comprising polyalkoxylated alkyl ethers, wherein the ratio of the nonionic surfactant to the alkoxylated alkyl ether is from 1:1 to 1.5:

1.

13. A method for preparing a composition according to any one of claims 1 to 12, wherein the method comprises the following steps: (i) Mixing a water-miscible liquid organic solvent with a nonionic surfactant to obtain a solution; and (ii) Add 50 to 500 g / L of clethodim to the solution obtained in step (i) and mix until a solution is obtained to obtain a stable liquid composition, wherein the liquid organic solvent accounts for 10-90% by weight of the composition.

14. The method of claim 13, wherein: a. The method further includes step (iii) of filtering the solution from step (ii) to obtain a stable liquid composition. b. Step (ii) includes filtering the solution from step (ii) into packaging to obtain a stable liquid composition in the package. c. Step (i) includes adding a C1-C6 alkyl polyalkoxylated ether to the water-miscible liquid organic solvent and nonionic surfactant solution of step (i), wherein the alkoxy group is selected from ethylene oxide, propylene oxide, and butane oxide, and combinations thereof. and / or d. Step (i) includes the step of adding an alkyl polyalkoxylated ether to a water-miscible organic solvent and a nonionic surfactant, wherein the alkyl polyalkoxylated ether is an ethoxypropoxybutyl ether.

15. The method according to claim 14, wherein the C1-C6 alkyl polyalkoxylated ether is ethoxypropoxybutyl ether.

16. A package comprising the composition of claim 1 prepared by the method according to option b of claim 14.

17. A method for a. To improve the shelf life, stability, herbicidal efficacy, or any combination thereof of compositions containing clethodim, said method comprising formulating said composition as defined in claim 1. b. Improving the chemical stability of clethodim, the method comprising reducing the amount of anionic surfactant in the composition as defined in claim 1 to equal or less than 0.2% by weight, based on the total weight of the composition. c. A stable liquid composition comprising clethodim and a water-miscible organic solvent, the method comprising formulating the composition as defined in claim 1 in the absence of ionic surfactants and in the presence of at least one nonionic surfactant. d. Physically stabilizing a liquid composition of clethodim in a poorly water-miscible organic solvent after dilution in the absence of ionic surfactants, the method comprising formulating the composition to have a high HLB value as defined in claim 1 by using at least one polymerizable surfactant having a high HLB value, or e. Improving the physical stability of a liquid composition containing clethodim in a poorly water-miscible organic solvent after dilution in the absence of ionic surfactants, wherein the composition contains a high HLB component and / or a surfactant, the method comprising formulating the composition as defined in claim 1 using at least two polymerizable surfactants.

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