Herbicidal composition containing a drift retardant and method for preparing the same

Abstract

A herbicidal composition for reducing off-site movement or drift of herbicides is described. The herbicidal composition can comprise a drift retardant (DRA) and at least one auxin herbicide and an emulsifier such as an alkyl polysaccharide, a phosphate ester, an ethoxylated castor oil or a combination thereof. A method for preparing such a composition is also described.

Description

[0001] Cross - reference to related applications

[0002] This application claims the benefit and priority of U.S. Provisional Application Serial No. 62 / 959,429, filed on January 10, 2020, the entire disclosure of which is incorporated herein by reference. TECHNICAL FIELD

[0003] The present disclosure generally relates to herbicidal composition concentrates comprising at least one auxin herbicide, at least one drift retardant agent (DRA), and an emulsifier. The present disclosure also generally relates to methods for preparing such herbicidal composition concentrates and DRA compositions for use in preparing herbicidal application mixtures. BACKGROUND ART

[0004] Auxin herbicides, such as dicamba (3,6-dichloro-2-methoxybenzoic acid) and 2,4-D (2,4-dichlorophenoxyacetic acid), are commonly used to control the growth of auxin-sensitive plants on agricultural and non-agricultural lands. The off-site movement of these herbicides has become a concern and may lead to restrictions in the use of these herbicides. For example, the migration of these herbicides from the application site to neighboring crop plants, such as soybeans and cotton, may occur, causing contact damage to sensitive plants. The off-site movement of auxin herbicides can occur through three main mechanisms: physical movement or drift of small particles in the spray, contamination of the sprayer, and volatility of the herbicide after application. Monsanto addressed the volatility issue by adding potassium acetate to auxin herbicide formulations using the Vaporgrip TM technology.

[0005] To address the drift problem, a drift retardant agent (DRA) (also known as a drift reducer or drift control agent) can be included in the herbicidal composition. DRAs for herbicidal sprays can act by altering the size distribution of the particles formed by the nozzle, for example, by partially suppressing the formation of the smallest particles (also known as driftable fines), which settle the slowest and are most prone to drift with the wind. The definition of the "driftable fines" size limit varies, but particles with a diameter below 150 μm are generally considered to be prone to drift. There are generally two types of DRAs. The first type of DRA is a polymer, which can increase the extensional viscosity of the spray mixture. These polymers, in commercial practice, are limited to polyacrylamide, polyethylene oxide, and guar gum, and can shift the spray particle size distribution to larger diameters. Although such polymers can for some nozzles, for example, TeeJet's Turbo Induction (TTI TM ) nozzles and Ultra Lo-Drift (ULD) nozzles effectively reduce driftable fine powders, but they may be less popular because they can result in significantly coarser sprays, which can provide poorer coverage and thus affect weed control. In addition, if such polymers are incorporated into herbicidal formulations, they typically result in unacceptably high viscosities.

[0006] A second type of DRA is referred to as an "oil-type" or "emulsion-type" DRA. As the name implies, oil-type DRAs (largely immiscible with water) can be included in tank formulations as emulsions or microemulsions. This type of drift retardant can be purchased as an additive to spray tanks under trade names such as Border EG (Precision Labs) and (Winfield). These oil-type or emulsion-type DRAs can effectively inhibit driftable fine powders, are suitable for a variety of nozzles, and have a relatively small effect on the average droplet size of the spray; thus, providing better application coverage and herbicidal efficacy. Although it is common and straightforward to use oil-type or emulsion-type DRAs as tank additives, there are still technical challenges in adding them to auxinic herbicide formulations, especially when producing auxinic herbicide formulations with a high auxinic herbicide load. For example, auxinic herbicides such as dicamba and 2,4-D are typically formulated as salts in concentrated aqueous solutions. It is well known that it is very difficult to stabilize emulsions in concentrated salt solutions because the performance of emulsifiers is poor at high ionic strengths. Current commercial examples are Dow's Enlist and Enlist One TM products, which incorporate a proprietary emulsion-type DRA into an aqueous solution of 2,4-D choline salt. Enlist also contains the dimethylamine salt of glyphosate. Clariant has also published a report on a proprietary DRA that can be added to the diglycolamine (DGA) salt of dicamba.

[0007] Accordingly, there is a need for auxinic herbicide compositions having a DRA added thereto to reduce herbicide drift, especially compositions that reduce drift without a significant reduction in herbicidal efficacy relative to currently available compositions. SUMMARY OF THE INVENTION

[0008] New and useful herbicidal compositions comprising a drift retardant (DRA) and methods of preparing the same are set forth in the appended claims. Illustrative embodiments are also provided to enable those skilled in the art to prepare and use the claimed subject matter.

[0009] In one aspect, a herbicidal composition concentrate is described. The herbicidal composition concentrate comprises at least one auxin herbicide, at least one drift retardant, and an emulsifier selected from: phosphate esters, alkyl polysaccharides, alkoxylated castor oils, and combinations thereof. The at least one drift retardant comprises one or more of the following: soybean oil or methyl ester of soybean oil; a compound according to Formula I:

[0010]

[0011] where n is 50–250; and a compound of Formula II

[0012]

[0013] where i + j + k = 10 to 50 and r + s + t = 3 to 12. In some embodiments, the auxin herbicide is selected from: dicamba, an agriculturally acceptable salt of dicamba, an agriculturally acceptable ester of dicamba, 2,4-D, an agriculturally acceptable salt of 2,4-D, an agriculturally acceptable ester of 2,4-D, and combinations thereof. In some embodiments, the herbicidal composition further comprises at least one monocarboxylic acid or its monocarboxylate salt.

[0014] In another aspect, a method for preparing a herbicidal composition concentrate is described. The method comprises mixing at least one auxin herbicide with at least one drift retardant and an emulsifier to form a herbicidal composition concentrate. The at least one drift retardant comprises one or more of the following: soybean oil or methyl ester of soybean oil; a compound according to Formula I:

[0015]

[0016] where n is 50–250; and a compound of Formula II

[0017]

[0018] where i + j + k = 10 to 50 and r + s + t = 3 to 12. The emulsifier is selected from: phosphate esters, alkyl polysaccharides, alkoxylated castor oils, and combinations thereof. In some embodiments, the auxin herbicide is selected from: dicamba, an agriculturally acceptable salt of dicamba, an agriculturally acceptable ester of dicamba, 2,4-D, an agriculturally acceptable salt of 2,4-D, an agriculturally acceptable ester of 2,4-D, and combinations thereof. In some embodiments, the method further comprises mixing at least one monocarboxylic acid or its monocarboxylate salt with at least one auxin herbicide, at least one drift retardant, and an emulsifier.

[0019] In another aspect, a drift retardant composition for preparing a herbicidal application mixture is described. The drift retardant composition comprises at least one drift retardant and an emulsifier. The at least one drift retardant comprises soybean oil or methyl ester of soybean oil, poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-, and octadecanoic acid, 12-hydroxy-, homopolymer, ester with α,α',α”-1,2,3-propanetriyl tris[ω-hydroxy poly(oxy-1,2-ethanediyl)]. The emulsifier is selected from the following: phosphate esters, alkyl polysaccharides, alkoxylated castor oils, and combinations thereof.

[0020] Upon reading this patent application, further benefits of the present invention will be apparent to those skilled in the art. The embodiments of the present invention described in the following paragraphs are intended to illustrate the present invention and should not be regarded as narrowing the scope of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] Figure 1A and 1B Illustrates a diglycolamine (DGA) dicamba composition with a built-in drift retardant, which is compared with the separate II / Clarity and with 6 oz / acre (ac) of together with II / Clarity.

[0022] Figure 2A and 2B Illustrate the humidome volatility of the I and tank mixture, respectively.

[0023] Figure 3 Illustrates the humidome volatility of a glyphosate and dicamba composition.

[0024] Figure 4 Illustrates the humidome volatility of other glufosinate and dicamba compositions. DETAILED DESCRIPTION

[0025] The following description of example embodiments provides information that enables those skilled in the art to make and use the subject matter set forth in the appended claims, but it may omit certain details that are well known in the art. Accordingly, the following detailed description should be considered illustrative and not restrictive.

[0026] The present invention provides a herbicidal composition concentrate comprising an auxinic herbicide, wherein the composition exhibits reduced drift. In particular, in addition to the auxinic herbicide, the composition further comprises at least one drift retardant (DRA) and an emulsifier. The at least one drift retardant may comprise soybean oil or methyl ester of soybean oil, poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-, and octadecanoic acid, 12-hydroxy-, homopolymer, ester with α,α',α”-1,2,3-propanetriyl tris[ω-hydroxy poly(oxy-1,2-ethanediyl)]. The emulsifier may be selected from the following: phosphate esters, alkyl polysaccharides, alkoxylated castor oils, and combinations thereof. The composition may further comprise at least one monocarboxylic acid or its monocarboxylate salt, which is used to reduce the volatility of the herbicide during application.

[0027] Typically, auxinic herbicides, such as dicamba and 2,4-D, are formulated in concentrated aqueous solutions in salt form. It is well known that it is very difficult to stabilize emulsions in concentrated salt solutions because the performance of emulsifiers is poor at high ionic strength. In addition, the inclusion of a monocarboxylic acid or its monocarboxylate salt for reducing volatility further increases the ionic strength of the composition, subsequently increasing the difficulty of stabilizing the oil-based DRA emulsion and preventing undesired creaming. However, it has surprisingly been found that emulsions and microemulsions of DRA can be stabilized in solutions containing auxinic herbicides, especially high-loaded auxinic herbicides in salt form (e.g., the monoethanolamine (MEA) salt of dicamba) and compositions comprising a monocarboxylic acid or monocarboxylate salt (such as potassium acetate). It has surprisingly been found that the DRA described herein can be included with the auxins described herein by including an emulsifier (such as phosphate esters, alkyl polysaccharides, alkoxylated castor oils or combinations thereof) to form a stable emulsion or microemulsion. The compositions described herein can control drift with a small amount of DRA, e.g., as low as about 0.5 oz / acre of DRA, which is significantly lower than the labeled rate of 4-6 oz / acre of Interlock TM The addition of a reduced amount of DRA is crucial for obtaining stable emulsion and microemulsion formulations with DRA and auxinic herbicides.

[0028] When applied using many common nozzles as per label instructions, the compositions provided herein can advantageously prevent drift of auxinic herbicides such as dicamba and 2,4-D. In addition, when DRA is required, the composition can provide compliance assurance, thus enhancing product stewardship. Adding DRA to the herbicidal composition concentrate also provides convenience and cost savings for growers and applicators compared to purchasing and adding the herbicide and DRA separately. In various aspects, the DRA described herein results in significant suppression of fines through the nozzle, such as but not limited to Greenleaf XL (TDXL), Lechler ID, Wilger DR, AIXR and TTI, without significantly increasing the average droplet size of the spray. The compositions with built-in DRA described herein are capable of improving spray quality, with better coverage and weed control.

[0029] A. Auxin herbicide component

[0030] The term "auxin herbicide" refers to a herbicide that acts as an analogue of the auxin plant growth hormone, thereby affecting plant growth regulation. Examples of auxin herbicides suitable for use in the herbicidal compositions of the present invention include, but are not limited to, benzoic acid herbicides, phenoxy herbicides, picolinic acid herbicides, pyridyloxy herbicides, pyrimidinecarboxylic acid herbicides, quinolinecarboxylic acid herbicides, and benzothiazole herbicides.

[0031] Examples of auxin herbicides include, but are not limited to: 3,6-dichloro-2-methoxybenzoic acid (dicamba); 2,4-dichlorophenoxyacetic acid (2,4-D); 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB); dichloroprop; 2-methyl-4-chlorophenoxyacetic acid (MCPA); 4-(4-chloro-2-methylphenoxy)butyric acid (MCPB); 4-chlorophenoxyacetic acid; 2,4,5-trichlorophenoxyacetic acid (2,4,5-T); clopyralid; picloram; fluroxypyr; triclopyr; mecoprop; picolinafen; quinclorac; cyclosulfamuron; benazolin; halauxifen; fluorpyrauxifen; methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate; 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate; benzyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate; methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indol-6-yl)pyridine-2-carboxylate; methyl 4-amino-3-chloro-6-[1-(2,2-dimethylpropionyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylate; methyl 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl]pyridine-2-carboxylate; methyl 6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate; butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, including its salts and esters; their racemic mixtures and resolved isomers; and combinations thereof.

[0032] In any embodiment, the herbicidal composition concentrate can comprise dicamba, or an agriculturally acceptable salt or ester thereof. Examples of suitable salts of dicamba include, but are not limited to, the N,N-bis-[aminopropyl]methylamine salt, the monoethanolamine (MEA) salt, the dimethylamine salt (e.g., etc.), the isopropylamine salt, the triethanolamine (TEA) salt, the diethanolamine salt (e.g., etc.), the potassium salt, and the sodium salt, and combinations thereof. Commercially available sources of dicamba and its agriculturally acceptable salts include those sold under the trade names DISTINCT, and sold.

[0033] In any embodiment, the herbicidal composition concentrate can comprise an agriculturally acceptable salt of dicamba, wherein the salt is selected from the following: N,N-[aminopropyl]methylamine salt, monoethanolamine salt, dimethylamine salt, isopropylamine salt, diethanolamine salt, potassium salt, and sodium salt, and combinations thereof.

[0034] Throughout the remainder of the specification of the present invention, when referring to dicamba or an agriculturally acceptable salt or ester thereof, those skilled in the art should understand that the principles of the present invention generally apply to auxin herbicides, including those described above, and the present invention is not limited to herbicidal compositions comprising dicamba or an agriculturally acceptable salt or ester thereof.

[0035] Additionally or alternatively, the herbicidal composition concentrate can comprise 2,4-D or an agriculturally acceptable salt or ester thereof. Examples of suitable salts of 2,4-D include, but are not limited to, the choline salt, the dimethylamine salt, the triethanolamine salt, and the isopropylamine salt, and combinations thereof. Examples of suitable esters of 2,4-D include, but are not limited to, the methyl ester, the ethyl ester, the propyl ester, the butyl ester (2,4-DB), and the isooctyl ester, and combinations thereof. Commercially available sources of 2,4-D and its agriculturally acceptable salts and esters include those sold under the trade names FORMULA and WEEDAR sold.

[0036] Additionally or alternatively, the herbicidal composition concentrate can comprise an agriculturally acceptable salt of 2,4-D, wherein the salt is selected from the following: choline salt, dimethylamine salt, triethanolamine salt, and isopropylamine salt, and combinations thereof.

[0037] Additionally or alternatively, the herbicidal composition concentrate can comprise an agriculturally acceptable ester of 2,4-D, wherein the ester is selected from the following: butyl ester (i.e., 2,4-DB) and isooctyl ester, and combinations thereof.

[0038] Alternatively or additionally, the herbicidal composition concentrate can comprise at least two auxin herbicides, for example, dicamba or an agriculturally acceptable salt or ester thereof, and 2,4-D or an agriculturally acceptable salt or ester thereof.

[0039] Alternatively or additionally, the herbicidal composition concentrate can comprise an agriculturally acceptable salt of an auxin herbicide (such as a dicamba salt, a 2,4-D salt, and / or a 2,4-DB salt), which is an ionic liquid as described in the published application US2013 / 0109572, i.e., a salt that is liquid at a temperature of about 150 °C or lower. The entire text of US2013 / 0109572 is incorporated herein by reference.

[0040] B. Drift Retardant (DRA) Component

[0041] In various aspects, the DRA can comprise one or more of the following: an oil or an ester thereof, poly(ethylene glycol) monooleate, and a polymer.

[0042] The oil or an ester thereof can be present in the DRA in an amount greater than or equal to about 50%, greater than or equal to about 60%, greater than or equal to about 70%, greater than or equal to about 80%, greater than or equal to about 85%, greater than or equal to about 90%, or about 95% by weight of the DRA; or from about 50% to about 95%, about 70% to about 95%, about 80% to about 95%, about 85% to about 95%, or about 90% to about 95% by weight of the DRA. Poly(ethylene glycol) monooleate can be present in the DRA in an amount greater than or equal to about 0.10%, greater than or equal to about 0.25%, greater than or equal to about 0.5%, greater than or equal to about 1%, greater than or equal to about 5%, or about 10% by weight of the DRA; from about 0.1% to about 10%, about 0.25% to about 10%, about 0.5% to about 10%, or about 1% to about 5% by weight of the DRA. The polymer can be present in the DRA in an amount greater than or equal to about 1%, greater than or equal to about 3%, greater than or equal to about 5%, greater than or equal to about 10%, greater than or equal to about 20%, greater than or equal to about 30%, greater than or equal to about 40%, or about 50% by weight of the DRA; or from about 1% to about 50%, about 3% to about 50%, about 5% to about 40%, or about 10% to about 30% by weight of the DRA.

[0043] Suitable oils include but are not limited to soybean oil (e.g., CAS Registry Number 8001-22-7) or an ester of soybean oil, such as methyl soyate (e.g., CAS Registry Number 67784-80-9). Suitable poly(ethylene glycol) monooleates include but are not limited to compounds of formula I:

[0044]

[0045] Where n is 50 - 250. In some embodiments, poly(ethylene glycol) monooleate can be poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy- (e.g., CAS Registry No. 9004-96-0).

[0046] Suitable polymers include, but are not limited to, compounds of formula II:

[0047]

[0048] Where i + j + k = 10 to 50 or 20 to 35 and r + s + t = 3 to 12 or 4 to 8. In any embodiment, each of i, j, and k can independently be an integer from 0 to 50, an integer from 0 to 35, an integer from 0 to 20, an integer from 0 to 10, an integer from 1 to 50, an integer from 1 to 35, an integer from 1 to 20, an integer from 1 to 10, an integer from 5 to 50, an integer from 5 to 35, an integer from 5 to 20, or an integer from 5 to 10. For example, i can be 1, j can be 5, and k can be 4; or i can be 0, j can be 10, and k can be 12, etc. In any embodiment, each of r, s, and t can independently be an integer from 0 to 12, an integer from 0 to 8, an integer from 0 to 4, an integer from 0 to 3, an integer from 1 to 12, an integer from 1 to 8, an integer from 1 to 4, an integer from 1 to 3, an integer from 2 to 12, an integer from 2 to 8, an integer from 2 to 4, or an integer from 2 to 3. For example, r can be 1, s can be 1, and t can be 1; or r can be 0, s can be 3, and t can be 5, etc. In some embodiments, the polymer can be octadecanoic acid, 12-hydroxy-, homopolymer, ester with α,α',α”-1,2,3-propanetriyltris[ω-hydroxy poly(oxy-1,2-ethanediyl)] (e.g., CAS Registry No. 1939051-18-9).

[0049] C. Emulsifier Component

[0050] Although the herbicidal activity of known herbicides such as glyphosate can be enhanced by certain cationic surfactants (e.g., tallow amine ethoxylate), it has been found that such surfactants are incompatible with compositions comprising a combination of an auxin herbicide (e.g., dicamba) and the DRA described herein and optionally a monocarboxylic acid or its monocarboxylate salt (e.g., potassium acetate). However, it has surprisingly been found that emulsifiers (such as phosphate esters, alkyl polysaccharides, alkoxylated castor oils or combinations thereof) can be included in the compositions described herein and stabilize emulsions or microemulsions of the DRA and the auxin herbicide and prevent the DRA from liquefying. As used herein, "emulsifier" is intended to cover surfactants and solvents. In addition, the emulsifiers described herein can provide a comparable level of glyphosate herbicidal activity. Thus, the composition concentrates described herein can control drift and provide an effective combination of two herbicides (e.g., dicamba and glyphosate or dicamba and glufosinate) in a convenient, stable, concentrated mixture, which optionally comprises a monocarboxylic acid or its monocarboxylate salt (e.g., potassium acetate, such as Vaporgrip TM Technology) to control the volatility of dicamba.

[0051] In any embodiment, the emulsifier can be a phosphate ester. Examples of suitable phosphate esters include, but are not limited to, alkoxylated phosphate esters of fatty acids. The alkoxylation can include alkoxy chains of any length. For example, polyethylene oxide or polypropylene oxide. Examples of such esters include polyethylene glycol octyl phosphate, polyethylene glycol isotridecyl phosphate, polyethylene glycol cetearyl phosphate, polyethylene glycol decyl phosphate, polyethylene glycol oleyl phosphate, polyethylene glycol polypropylene glycol cetyl phosphate, polyethylene glycol tridecyl phosphate, and polyethylene glycol isotridecyl phosphate. Non-limiting examples of commercially available phosphate esters include 8182, 8181 and 8180, TAABS-8 and TAABS-5.

[0052] Additionally or alternatively, the emulsifier can be an alkyl polysaccharide. Examples of suitable alkyl polysaccharides include, but are not limited to, compounds of formula (1):

[0053] R 11 -O-(sug) u Formula (1)

[0054] wherein R 11is a straight-chain or branched, substituted or unsubstituted hydrocarbyl group selected from alkyl, alkenyl, alkylphenyl, alkenylphenyl having from about 4 to about 22 carbon atoms or from about 4 to 18 carbon atoms. The sug moiety is a sugar residue and can be in an open or cyclic (i.e., pyranose) structure. The sugar can be a monosaccharide, disaccharide, oligosaccharide or polysaccharide having 5 or 6 carbon atoms. Examples of suitable sugar moieties (including their corresponding pyranose forms) include ribose, xylose, arabinose, glucose, galactose, mannose, talose, gulose, allose, altrose, idose, lyxose, ribulose, sorbose (sorbitan), fructose and mixtures thereof. Examples of suitable disaccharides include maltose, lactose and sucrose. The disaccharides, oligosaccharides and polysaccharides can be a combination of two or more of the same sugar, such as maltose (two glucoses), or a combination of two or more different sugars, such as sucrose (a combination of glucose and fructose). The degree of polymerization u is an average value from 1 to about 10, from 1 to about 8, from 1 to about 5, from 1 to about 3 and from 1 to about 2.

[0055] In various embodiments, the alkyl polysaccharide can be an alkyl polyglucoside (APG) surfactant of formula (1), wherein: R 11 is a branched or straight-chain alkyl group preferably having 4 to 22 carbon atoms or 8 to 18 carbon atoms, or a mixture of alkyl groups having an average value within a given range; sug is a glucose residue (e.g., glucoside); and u is from 1 to about 5, and more preferably from 1 to about 3. In various embodiments, the emulsifier component comprises an APG of formula (1), wherein R 11 is a branched or straight-chain alkyl group having 8 to 10 carbon atoms or a mixture of alkyl groups having an average value within a given range, and u is from 1 to about 3.

[0056] Non-limiting examples of commercially available alkyl polyglucosides include, for example, those from BASF Inc. or surfactants such as Agnique PG 264, Agnique PG 8105 and Agnique 8107.

[0057] Additionally or alternatively, the emulsifier can be an alkoxylated castor oil, such as ethoxylated castor oil or propoxylated castor oil. The alkoxylated castor oil can be prepared by reacting castor oil or hydrogenated castor oil with ethylene oxide, propylene oxide, ethylene glycol or propylene glycol. Examples of suitable alkoxylated castor oils include, but are not limited to, those available from Stepan Chemical Company CO-40 (40 EO), 8242, and Cirrasol TM G-1292 (25 EO) available from Croda Inc. Other non-limiting examples include 8243 and 8244. Other suitable examples can include Emulpon CO - 550, CO - 360 from AkzoNobel Nouryon, CO - 200 and Surfom R 360 and R 540 from Oxiteno.

[0058] Additionally or alternatively, the emulsifier can be an alkoxylated fatty acid ester. Non - limiting examples of such esters include ethoxylated methyl esters of fatty acids, such as the commercially available ME 818 - 5. Other suitable examples can include EM V20.

[0059] D. Monocarboxylic acid / monocarboxylate component

[0060] "Monocarboxylic acid" refers to a hydrocarbon or substituted hydrocarbon that contains only one carboxyl functional group (i.e., R 1 -C(O)OH). "Monocarboxylate" refers to a salt (i.e., R 1 -C(O)OM, where M is an agriculturally acceptable cation). In one embodiment, the composition comprises at least one monocarboxylate, which can exist in the aqueous composition in whole or in part in dissociated form as a monocarboxylate anion and the corresponding cation.

[0061] Typical monocarboxylic acids and monocarboxylates generally contain a hydrocarbon or unsubstituted hydrocarbon selected from, for example, unsubstituted or substituted straight - chain or branched alkyl groups (e.g., C1 - C 20 alkyl groups such as methyl, ethyl, n - propyl, isobutyl, etc.), unsubstituted or substituted straight - chain or branched alkenyl groups (e.g., C2 - C 20 hydrocarbon groups such as vinyl, n - propenyl, isopropenyl, etc.), unsubstituted or substituted aryl groups (e.g., phenyl, hydroxyphenyl, etc.), or unsubstituted or substituted aralkyl groups (e.g., benzyl). In one embodiment, the monocarboxylic acid is selected from formic acid, acetic acid, propionic acid, and benzoic acid. In another embodiment, the monocarboxylate is selected from formate, acetate, propionate, and benzoate.

[0062] In one embodiment, the herbicidal composition comprises a monocarboxylate having the formula R 1 -C(O)OM, where R 1 is an unsubstituted or substituted C1 - C 10 alkyl group, and M is an agriculturally acceptable cation other than ammonia. In another embodiment, the herbicidal composition comprises a monocarboxylate having the formula R 1 -C(O)OM, where R 1is an unsubstituted C1-C6 alkyl group, and M is an alkali metal salt. In another embodiment, the herbicidal composition comprises a monocarboxylate having the formula R 1 -C(O)OM, wherein R 1 is an unsubstituted C1-C3 alkyl group, and M is an alkali metal salt selected from sodium and potassium. In another embodiment, the monocarboxylate is potassium acetate. In another embodiment, the monocarboxylate is sodium acetate.

[0063] In any embodiment, the herbicidal composition concentrate described herein may have a pH preferably equal to or higher than the acid dissociation constant (pKa) of the monocarboxylic acid (if present in the composition). For example, the herbicidal composition concentrate may contain acetic acid (which has a pKa of about 4.8) and have a pH equal to or greater than about 4.8.

[0064] E. Alkali metal phosphate / alkali metal carbonate

[0065] The herbicidal composition concentrate may optionally further comprise an alkali metal phosphate, such as dipotassium hydrogen phosphate. For example, dipotassium hydrogen phosphate can provide additional buffering and / or water-conditioning for the aqueous herbicidal composition of the present invention. In a herbicidal composition application mixture prepared using hard water, dipotassium hydrogen phosphate is particularly effective as a substitute for ammonium sulfate.

[0066] Additionally or alternatively, the herbicidal composition concentrate may optionally further comprise an alkali metal carbonate, such as potassium carbonate, to provide additional buffering and / or water-conditioning for the aqueous herbicidal composition of the present invention.

[0067] F. Non-herbicide additives

[0068] The herbicidal composition concentrate may optionally further comprise conventional additives, such as other surfactants, safeners, solubilizers, thickeners, flow enhancers, foam regulators, cryoprotectants, UV protectants, preservatives, antimicrobial agents, and / or other additives that are necessary or desired for improving the performance, crop safety, or handling of the composition.

[0069] In any embodiment, the herbicidal composition concentrate may contain less than about 10 ppm of ammonium sulfate. In another embodiment, the herbicidal composition concentrate does not contain ammonium sulfate.

[0070] In any embodiment, the herbicidal composition concentrate does not contain acids other than monocarboxylic acids.

[0071] G. Other herbicide components

[0072] The herbicidal composition concentrate may optionally comprise at least one other herbicide. Representative examples of other herbicides include, but are not limited to, hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetyl-CoA carboxylase (ACC enzyme) inhibitors, acetolactate synthase (ALS) inhibitors, acetohydroxyacid synthase (AHAS) inhibitors, photosystem II (PS II) inhibitors, photosystem I (PS I) inhibitors, protoporphyrinogen oxidase (PPO or Protox) inhibitors, carotenoid biosynthesis inhibitors, enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, glutamine synthetase inhibitors, dihydropteroate synthase inhibitors, mitotic inhibitors, nucleic acid inhibitors, cellulose inhibitors, oxidative phosphorylation uncouplers, dihydropteroate synthase inhibitors, fatty acid and lipid biosynthesis inhibitors, auxin transport inhibitors, their salts and esters, their racemic mixtures and resolved isomers, and mixtures thereof; their salts and esters; their racemic mixtures and resolved isomers; and combinations thereof.

[0073] The application mixture can be prepared by diluting the aqueous herbicidal concentrate composition as described herein. Other herbicides can be "tank-mixed" with the application mixture prepared from the aqueous herbicidal concentrate composition described herein.

[0074] Examples of herbicides among these other herbicide categories are provided below. When a herbicide is mentioned herein by name generically, unless otherwise restricted, the herbicide includes all commercially available forms known in the art, such as salts, esters, free acids and free bases, and their stereoisomers.

[0075] Representative examples of HPPD inhibitors include, but are not limited to, acifluorfen, aminotriazole, butafenacil, carfentrazone-ethyl, clomazone, dimethenamid, fluridone, flurochloridone, flurtamone, isoxachlortole, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrazolate, pyrazoxyfen, sulcotrione, tefuryltrione, their salts and esters, and mixtures thereof.

[0076] Representative examples of ACC enzyme inhibitors include, but are not limited to, alloxydim, butroxydim, clethodim, cycloxydim, fenoxaprop-P-ethyl, sethoxydim, tepraloxydim, and tralkoxydim, their salts and esters, and mixtures thereof. Another group of ACC enzyme inhibitors includes chlorazifop, clodinafop-propargyl, clofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop-P, fluazifop-P-butyl, isoxaben, metamifop, propaquizafop, quizalofop-P, quizalofop-P-ethyl, and trifop, their salts and esters, and mixtures thereof. ACC enzyme inhibitors also include mixtures of one or more "dim" and one or more "fop", and their salts and esters.

[0077] Representative examples of ALS or AHAS inhibitors include, but are not limited to, acylsulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethoxysulfuron, flazasulfuron, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl-sodium, metsulfuron-methyl, nicosulfuron, penoxsulam, primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, tribenuron-methyl, tritosulfuron, trifloxysulfuron-sodium, and flupyrsulfuron-methyl-sodium, their salts and esters, and mixtures thereof.

[0078] Representative examples of photosystem I inhibitors include, but are not limited to, diquat and paraquat, their salts and esters, and mixtures thereof. Representative examples of photosystem II inhibitors include, but are not limited to, ametryn, amicarbazone, atrazine, bentazone, bromacil, bromoxynil, chlorotoluron, cyanazine, desmedipham, desmetryn, oxaziclomefone, diuron, fluometuron, hexazinone, ioxynil, isoproturon, linuron, metobenzuron, methabenzthiazuron, metoxuron, propazine, simetryn, simazine, terbacil, terbuthylazine, and trietazine, their salts and esters, and mixtures thereof.

[0079] Representative examples of PPO inhibitors include, but are not limited to, diphenyl ethers (acifluorfen, bifenox, methoxyfenozide, nitrofen, lactofen, fluoroglycofen-ethyl, fomesafen, lactofen, oxyfluorfen), N-phenylphthalimides (cinidon-ethyl, fumiclorac, flumiclorac-pentyl, flumioxazin), oxadiazoles (oxadiargyl, oxadiazon), oxazolidinediones (pentoxazone), phenylpyrazoles (fluazolate, pyraflufen-ethyl), pyrimidinediones (bispyribac-sodium, flupropacil, pyriftalid, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate), thiadiazoles (methazole, thidiazimin), triazinones (fluthiacet-methyl), triazolinones (carfentrazone-ethyl, sulfentrazone, mesotrione), and others (flufenpyr-ethyl, fluzolate, bipyriminil).

[0080] Representative examples of carotenoid biosynthesis inhibitors include, but are not limited to, acifluorfen, aminotriazole, flufenican, mesotrione, and sulcotrione.

[0081] Representative examples of EPSP inhibitors include, but are not limited to, N-phosphonomethylglycine (glyphosate).

[0082] Representative examples of glutamine synthetase inhibitors include, but are not limited to, glufosinate.

[0083] Representative examples of dihydropteroate synthase inhibitors include, but are not limited to, sulfometuron.

[0084] Representative examples of mitosis inhibitors include, but are not limited to, acetochlor, alachlor, fluthiacet-methyl, S-metolachlor, and thiazopyr.

[0085] Representative examples of nucleic acid inhibitors include, but are not limited to, difenzoquat, fosamine, metam-sodium, and pelargonic acid.

[0086] In any embodiment, the herbicidal composition concentrate further comprises an additional herbicide selected from: acetochlor, glyphosate, glufosinate, flumioxazin, fomesafen, and their agriculturally acceptable salts.

[0087] In one embodiment, the herbicidal composition concentrate further comprises glyphosate or its agriculturally acceptable salt. Suitable glyphosate salts include, for example, the ammonium salt, diammonium salt, dimethylammonium salt, monoethanolamine salt, isopropylammonium salt, and potassium salt, and combinations thereof. In any embodiment, the glyphosate salt is selected from the monoethanolamine salt, isopropylammonium salt, and potassium salt, and combinations thereof.

[0088] In any embodiment, the herbicidal composition concentrate further comprises glufosinate or its agriculturally acceptable salt.

[0089] In any embodiment, the herbicidal composition concentrate comprises dicamba or its agriculturally acceptable salt or ester, and glyphosate or its agriculturally acceptable salt. Additionally or alternatively, the herbicidal composition concentrate comprises dicamba or its agriculturally acceptable salt; glyphosate or its agriculturally acceptable salt; and an agriculturally acceptable acetate other than ammonia. Commercially available sources of glyphosate and its agriculturally acceptable salts include those sold under the trade names HONCHO ROUNDUP ROUNDUP and those products sold under

[0090] Additionally or alternatively, the herbicidal composition concentrate comprises 2,4-D or its agriculturally acceptable salt or ester, and glyphosate or its agriculturally acceptable salt. Additionally or alternatively, the herbicidal composition concentrate comprises 2,4-D or its agriculturally acceptable salt or ester; glyphosate or its agriculturally acceptable salt; and an agriculturally acceptable acetate other than ammonia.

[0091] In any embodiment, the herbicidal composition concentrate comprises dicamba or an agriculturally acceptable salt or ester thereof, and glufosinate or an agriculturally acceptable salt thereof. Additionally or alternatively, the herbicidal composition concentrate comprises 2,4-D or an agriculturally acceptable salt or ester thereof, and glufosinate or an agriculturally acceptable salt thereof.

[0092] In any embodiment, the herbicidal composition concentrate comprises an agriculturally acceptable non - auxin herbicide salt (such as a glyphosate salt), which is an ionic liquid described in published application US2013 / 0109572, i.e., a salt that is liquid at about 150 °C or lower temperature.

[0093] H. Component Loading

[0094] 1. Herbicide Loading:

[0095] The herbicidal composition concentrates described herein can be diluted with water before application. The concentrated herbicidal compositions as described herein can generally comprise a total herbicide loading, based on acid equivalent (a.e. or ae), for example, from about 120 to about 600 g a.e. / L, from about 300 to about 600 g a.e. / L, from about 350 to about 600 g a.e. / L, from about 400 to about 600 g a.e. / L, from about 450 to about 600 g a.e. / L or from about 500 to about 600 g a.e. / L. As used herein, the term "total herbicide loading" encompasses the herbicide loading when only one herbicide is present in the composition, e.g., one auxin herbicide or one non - auxin herbicide, as well as the total loading when one or more herbicides are present (e.g., two auxin herbicides or an auxin herbicide and a non - auxin herbicide). Other examples of representative total herbicide loadings include about 120, 150, 200, 250, 300, 350, 400, 450, 500, 550 and 600 g a.e. / L and ranges thereof (i.e., total herbicide loadings from about 120 to about 150 g a.e. / L, from about 150 to about 200 g a.e. / L, from about 200 to about 250 g a.e. / L, from about 250 to about 300 g a.e. / L, from about 300 to about 350 g a.e. / L, from about 350 to about 400 g a.e. / L, from about 400 to about 450 g a.e. / L, from about 450 to about 500 g a.e. / L, from about 500 to about 550 g a.e. / L, from about 550 to about 600 g a.e. / L).

[0096] In any embodiment, the herbicidal composition can be a liquid concentrate that contains, for example, based on the weight of the composition concentrate, a total amount (acid equivalent weight) of herbicide that is greater than or equal to about 5%, greater than or equal to about 10%, greater than or equal to about 15%, greater than or equal to about 20%, greater than or equal to about 30%, greater than or equal to about 40%, greater than or equal to about 50%, greater than or equal to about 60%, or about 70%. Additionally or alternatively, the herbicidal composition is a liquid concentrate that contains, for example, based on the weight of the composition concentrate, a total amount (acid equivalent weight) of herbicide from about 5% to about 70%, about 5% to about 60%, about 5% to about 50%, about 10% to about 40%, about 10% to about 30%, or about 10% to about 20%.

[0097] In a herbicidal composition concentrate containing an auxinic herbicide and a non-auxinic herbicide, the weight ratio of the auxinic herbicide to the non-auxinic herbicide, in acid equivalents, is generally not greater than about 50:1, for example, about 50:1, 25:1, 10:1, 5:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:5, about 1:10, or ranges such as from about 50:1 to about 1:10, from about 50:1 to about 1:5, from about 50:1 to about 1:1, from about 50:1 to about 3:1, from about 50:1 to about 5:1, from about 50:1 to about 10:1, from about 25:1 to about 1:1, or from about 25:1 to about 3:1.

[0098] In a particular embodiment, the herbicidal composition concentrate can contain an auxinic herbicide in an amount (acid equivalent weight) of about 5% to about 70%, about 5% to about 60%, about 5% to about 50%, about 10% to about 40%, about 10% to about 30%, or about 10% to about 20% based on the weight of the composition concentrate, and a non-auxinic herbicide in an amount (acid equivalent weight) of about 10% to about 70%, about 15% to about 60%, about 15% to about 50%, or about 20% to about 40% based on the weight of the composition concentrate.

[0099] For any given auxinic herbicide, one of ordinary skill in the art can readily determine, using routine experimentation, the minimum concentration of the auxinic herbicide and the minimum ratio of the auxinic herbicide contained in the herbicidal composition to any other auxinic herbicide and / or non-auxinic herbicide that is required for the intended application.

[0100] 2. Drift Retardant (DRA) Loading:

[0101] In any embodiment, at least one DRA as described herein can be present in the composition concentrate, with the total DRA loading being greater than or equal to about 1%, greater than or equal to about 2%, greater than or equal to about 5%, greater than or equal to about 8%, greater than or equal to about 10%, greater than or equal to about 12%, greater than or equal to about 15%, or about 20% by weight of the composition concentrate. As used herein, the term "total DRA loading" encompasses the DRA loading when only one DRA is present in the composition and the total loading when one or more DRAs are present. Additionally or alternatively, at least one DRA can be present in the composition concentrate, with the total DRA loading being about 1% to about 20%, about 1% to about 15%, about 2% to about 12%, about 2% to about 10%, or about 5% to about 10% by weight of the composition concentrate.

[0102] 3. Total emulsifier loading

[0103] In any embodiment, an emulsifier as described herein can be present in the composition concentrate, with the total emulsifier loading being greater than or equal to about 1 wt.%, greater than or equal to about 2 wt.%, greater than or equal to about 3 wt.%, greater than or equal to about 4 wt.%, greater than or equal to about 5 wt.%, greater than or equal to about 6 wt.%, greater than or equal to about 7 wt.%, greater than or equal to about 8 wt.%, greater than or equal to about 9 wt.%, greater than or equal to about 10 wt.%, greater than or equal to about 12 wt.%, greater than or equal to about 15 wt.%, greater than or equal to about 20 wt.%, greater than or equal to about 25 wt.%, greater than or equal to about 25 wt.%, or about 30 wt.% by weight of the composition concentrate. As used herein, the term "total emulsifier loading" encompasses the emulsifier loading when only one emulsifier is present in the composition and the total loading when one or more emulsifiers are present. Additionally or alternatively, an emulsifier can be present in the composition concentrate, with the total emulsifier loading being about 1 wt.% to about 30 wt.%, about 1 wt.% to about 25 wt.%, about 2 wt.% to about 25 wt.%, about 3 wt.% to about 25 wt.%, about 4 wt.% to about 25 wt.%, about 5 wt.% to about 25 wt.%, about 5 wt.% to about 20 wt.%, about 10 wt.% to about 20 wt.%, about 15 wt.% to about 20 wt.%, or about 10 wt.% to about 15 wt.% by weight of the composition concentrate.

[0104] 4. Monocarboxylic acid / monocarboxylate loading:

[0105] In any embodiment, the herbicidal composition concentrate can comprise a single monocarboxylic acid or its monocarboxylate, or a mixture of two or more monocarboxylic acids or their monocarboxylates.

[0106] In various embodiments, the concentration of the volatile auxin herbicide in the vapor phase of the herbicidal composition comprising an auxin herbicide and a monocarboxylic acid or its monocarboxylate salt is less than about 90%, 80%, 70%, 60%, 50%, 40%, 30%, 20%, 10%, or 5% of the concentration of the volatile auxin herbicide in the vapor phase of a reference composition that does not contain the monocarboxylate salt.

[0107] The loading of the monocarboxylic acid or monocarboxylate salt of the herbicidal composition can generally depend on the auxin herbicide loading of the herbicidal composition, the salt form of the auxin herbicide, and the nature of any other components of the herbicidal composition, and is an amount sufficient to reduce the volatility of the auxin herbicide (relative to a reference composition that does not contain the monocarboxylic acid or monocarboxylate salt but otherwise has the same composition). For example, the monoethanolamine salt and diglycolamine salt of dicamba are less volatile than the dimethylamine salt and isopropylamine salt of dicamba, and the loading required for the less volatile salts can be less than the loading required for the more volatile salts. Additionally, the loading of the monocarboxylic acid or its monocarboxylate salt can vary with the specific combination of the auxin herbicide, optional non-auxin herbicide, and monocarboxylic acid or monocarboxylate salt.

[0108] In the herbicidal composition concentrates described herein, the molar ratio of the auxin herbicide to the monocarboxylic acid or its monocarboxylate salt is generally not less than about 1:10 and not greater than about 10:1. Representative molar ratios of auxin herbicide acid equivalent (a.e.) to total monocarboxylic acid or monocarboxylate salt are, for example, from 1:10 to about 10:1, from about 3:10 to about 10:1, from about 1:5 to about 5:1, and from about 3:1 to about 1:3. In any embodiment, the molar ratio of the auxin herbicide to the monocarboxylic acid or monocarboxylate salt is from about 2:1 to about 1:2. In any embodiment, the molar ratio of the auxin herbicide to the monocarboxylic acid or monocarboxylate salt is about 1:1.

[0109] In any embodiment, the herbicidal composition concentrate can contain the monocarboxylic acid or its monocarboxylate salt in an amount of from about 0.25% to about 35%, about 5% to about 30%, or about 5% to about 20% (by weight of acid equivalent) based on the weight of the concentrate.

[0110] 5. Alkali metal phosphate / alkali metal carbonate loading

[0111] When the herbicidal composition concentrate contains an alkali metal phosphate such as dipotassium hydrogen phosphate, the molar ratio of the alkali metal phosphate to the monocarboxylic acid or its monocarboxylate salt can be, for example, from about 1:5 to about 5:1, from about 3:1 to about 1:3, or from about 2:1 to about 1:2. In any embodiment, the molar ratio of the alkali metal phosphate to the monocarboxylic acid or monocarboxylate salt is about 1:1.

[0112] When the herbicidal composition concentrate comprises an alkali metal carbonate such as potassium carbonate, the molar ratio of the alkali metal carbonate to the monocarboxylic acid or its monocarboxylate salt can be, for example, from about 1:5 to about 5:1, from about 3:1 to about 1:3, or from about 2:1 to about 1:2. In any embodiment, the molar ratio of the alkali metal carbonate to the monocarboxylic acid or its monocarboxylate salt is about 1:1.

[0113] I. Method for preparing a herbicidal composition concentrate

[0114] Also provided is a method for preparing a herbicidal composition concentrate as described herein. The formed herbicidal composition concentrate can be an emulsion or a microemulsion. The method can include mixing at least one auxin herbicide as described herein with at least one drift retardant (DRA) as described herein and an emulsifier as described herein to form a herbicidal composition concentrate. For example, the DRA can comprise soybean oil or methyl ester of soybean oil, poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-, and octadecanoic acid, 12-hydroxy-, homopolymer, ester with α,α',α”-1,2,3-propanetriyltris[ω-hydroxy poly(oxy-1,2-ethanediyl)]. The DRA can comprise soybean oil or methyl ester of soybean oil in an amount of about 80% to about 95% by weight of the DRA, poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy- in an amount of about 0.25% to about 10% by weight of the DRA, and octadecanoic acid, 12-hydroxy-, homopolymer, ester with α,α',α”-1,2,3-propanetriyltris[ω-hydroxy poly(oxy-1,2-ethanediyl)] in an amount of about 3% to about 50% by weight of the DRA.

[0115] The emulsifier can be selected from phosphate esters, alkyl polysaccharides, alkoxylated castor oils, and combinations thereof. For example, at least one auxin herbicide can be selected from dicamba, agriculturally acceptable salts of dicamba (e.g., N,N-[aminopropyl]methylamine salt, monoethanolamine salt, dimethylamine salt, isopropylamine salt, diethanolamine salt, potassium salt, and sodium salt, and combinations thereof), agriculturally acceptable esters of dicamba, 2,4-D, agriculturally acceptable salts of 2,4-D, agriculturally acceptable esters of 2,4-D, and combinations thereof.

[0116] The total herbicide load of the composition concentrate can be as described herein, for example, in an amount of about 5% to about 50% (acid equivalent weight) based on the weight of the composition concentrate. The total DRA load of the composition concentrate can be as described herein, for example, in an amount of about 2% to about 10% based on the weight of the composition concentrate. The total emulsifier load of the composition concentrate can be as described herein, for example, in an amount of about 1% to about 20% based on the weight of the composition concentrate.

[0117] In any embodiment, the method may further comprise mixing at least one auxinic herbicide with water to form an aqueous solution before mixing with at least one drift retardant and an emulsifier. Additionally or alternatively, the method may further comprise mixing at least one monocarboxylic acid (e.g., acetic acid) or its monocarboxylate salt (e.g., potassium acetate) with at least one auxinic herbicide, at least one drift retardant, and an emulsifier. In any embodiment, the herbicidal composition concentrate may contain, by weight of the concentrate, for example, about 5% to about 30% of the amount (acid equivalent weight) of the monocarboxylic acid or its monocarboxylate salt as described herein and / or, for example, a molar ratio of at least one monocarboxylic acid or its monocarboxylate salt to the auxinic herbicide as described herein of about 1:10 to about 10:1.

[0118] Additionally or alternatively, the method may further comprise mixing at least one other herbicide (e.g., glyphosate, an agriculturally acceptable salt of glyphosate, glufosinate, an agriculturally acceptable salt of glufosinate, and combinations thereof) with at least one auxinic herbicide, at least one DRA, and an emulsifier. Optionally, an antifoaming agent may be added to inhibit the formation of foam during mixing. Suitable antifoaming agents include, but are not limited to, silicone antifoaming agents, e.g., SAG 1572 available from Momentive. The other herbicide may be present in the herbicidal composition concentrate in the amounts (acid equivalent weight) as described herein, e.g., about 15% to about 60% by weight of the composition.

[0119] J. Drift Retardant (DRA) Composition

[0120] Also provided herein is a drift retardant (DRA) composition for preparing a herbicidal application mixture. The DRA composition may comprise at least one DRA as described herein and an emulsifier as described herein. For example, the DRA may comprise soybean oil or methyl ester of soybean oil, poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-, and octadecanoic acid, 12-hydroxy-, homopolymer, ester with α,α',α”-1,2,3-propanetriyltris[ω-hydroxy poly(oxy-1,2-ethanediyl)]. The emulsifier may be, for example, a phosphate ester, an alkyl polysaccharide, an alkoxylated castor oil, or a combination thereof. It is contemplated herein that the DRA composition may be mixed with other components such as the herbicides as described herein and / or the monocarboxylic acid / monocarboxylate salt as described herein and / or water to form an application mixture.

[0121] The present invention has been described in detail, and it is apparent that modifications and variations can be made without departing from the scope of the invention as defined by the appended claims.

[0122] Examples

[0123] The following non-limiting examples are provided to further illustrate the present invention. It should be noted that the following composition examples are presented based on the components that were initially combined to form the reported tank mixtures or concentrates. Various embodiments of the present invention are intended to cover such initial compositions as well as any corresponding compositions resulting from the interactions between the components once combined, such as the in-situ formation of a monocarboxylate salt by combining a monocarboxylic acid with a neutralizing base.

[0124] Unless otherwise noted, 2601 used in the following examples includes:

[0125] Soybean oil (CAS Registry Number 8001-22-7), in the range of 80% to 95% by weight;

[0126] Poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy- (CAS Registry Number 9004-96-0), in the range of 0.25% to 10% by weight; and

[0127] Octadecanoic acid, 12-hydroxy-, homopolymer, ester with α,α',α”-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)] (CAS Registry Number 1939051-18-9), in the range of 3% to 50% by weight.

[0128] Unless otherwise noted, 2602 used in the following examples includes:

[0129] Soybean oil methyl ester (CAS Registry Number 67784-80-9), in the range of 80% to 95% by weight;

[0130] Poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy- (CAS Registry Number 9004-96-0), in the range of 0.25% to 10% by weight; and

[0131] Octadecanoic acid, 12-hydroxy-, homopolymer, ester with α,α',α”-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)] (CAS Registry Number 1939051-18-9), in the range of 3% to 50% by weight.

[0132] Example 1 - Dicamba and 2,4-D Straight-Goods Composition without Vaporgrip TM ​

[0133] Prepare the drift retardant formulations shown in Table 1. Mix all components in a beaker with magnetic stirring. Add monoethanolamine (MEA) to neutralize the phosphate ester in the dicamba formulation.

[0134] Table 1: Without Vaporgrip TMAuxin Straight-Goods formulations

[0135]

[0136]

[0137] Spray droplet size studies were conducted on these formulations, all of which had a drift retardant concentration that provided a 2 oz / ac rate in the spray tank ( Figure 1A - 1B ). All data collected was at 1120 / 560 g / ha ae, 10 gallons (37.8541 liters) per acre (ac, 0.404686 ha). Droplet size data was from the Q164 Spray Particle Size Facility, conducted on 6 '05 nozzles at 40 psi. Formulations 1-3 and Formulation 1-1 in-tank mixtures were made with Roundup . All tank mixtures were prepared to deliver 560 / 1120 g / ha ae dicamba / glyphosate at 10 gallons per acre.

[0138] It was found that on most nozzles, 2 oz / ac of 2601 in-tank Formulation 1-1 (which was tank mixed with Roundup ) provided suppression of the driftable fines (volume % < 150 μm), which was comparable to a high ratio. The Wilger DR 11005 and Greenleaf TDXL 11005 nozzles used with Formulation 1-1 at 40 psi provided as low a level of fines as the TTI 11005 nozzle at the same pressure. At 2 oz / ac, 2602 also provided a significant reduction in driftable fines, but 2601 was somewhat more effective at that rate. Unlike polymer drift retardants, emulsion drift retardants had little effect on the volume-weighted mean droplet size Dv50 (also known as VMD).

[0139] Example 2 - Composition with TEA salt of 2,4 - D and DRA

[0140] Conventional emulsions of drift retardants in the TEA salt of 2,4-D were developed based on a 39.4% a.e. solution of the 2,4-D TEA salt, as shown in Table 2 below. Three formulations were developed that exhibited good physical stability.

[0141] Table 2: 2,4-D TEA Compositions with DRA

[0142]

[0143] Example 3 - Dicamba Straight-Goods Composition Containing Vaporgrip TM ​

[0144] Compositions 3-1 and 3-2 were prepared from a dicamba stock solution (Table 3), which was mixed with a drift retardant, then a dispersant was added, and the mixture was stirred with a turrax high-shear mixer at 10 krpm for approximately 15 seconds.

[0145] Table 3: Dicamba compositions containing DRA and Vaporgrip TM

[0146]

[0147] Table 4: Straight-goods dicamba compositions containing high-loading Vaporgrip TM

[0148]

[0149]

[0150] Table 5: Comparison of the compositions in Table 4 with those in Table 3

[0151]

[0152] Example 4 – Humidome study

[0153] Compositions 4-1, 4-2, and 4-3 were submitted as tank mixtures with Roundup I and with for humidity control dome studies. Xtendimax (Xmax)-Powermax (PMax) with or without potassium acetate tank mix adjuvant was used as a control. A new 1-1 / 8 lb glyphosate rate was used for Roundup I and a 34-oz rate of The results are shown in Tables 6 and Figure 2A - 2B as follows. The data in Table 10 show that the Vaporgrip TM levels in Compositions 4-2 and 4-3 reduced the volatility of the high-rate tank mixtures to the level of the gold standard Xmax-Pmax-potassium acetate tank mixture. Using I, none of the formulations reached that level, but both formulations reduced dicamba volatility by approximately one order of magnitude compared to the levels of 0.2 - 0.5 ng / L typically seen with Xtendimax-Powermax in this assay (not performed in this experiment).

[0154] Table 6: Dicamba volatility, expressed as the average air concentration over 24 hours

[0155] ​​

[0156]

[0157] Table 7: Variants of Composition 4-2 with Improved Emulsification

[0158]

[0159] The dicamba straight goods formulation, especially Composition 4-2, provides excellent control of drift and volatility.

[0160] Example 5 - Dicamba - Glyphosate and Vaporgrip TM Premix

[0161] As shown in the table below, a basic formulation 8-1 containing dicamba:acetic acid 1:1.5 mol:mol for emulsifying the drift agent was prepared.

[0162] Table 8: Formulation 8-1

[0163]

[0164] Example 6 – Greenhouse test

[0165] A series of formulations GO5, JO3, JO5, EO5, IO5 were prepared by taking the components shown in Table 9 and adding the balance of the basic formulation 8-1 shown in Table 8. Greenhouse tests with ELEIN control at half rate (560 - 280 g / ha a.e. glyphosate - dicamba) are shown.

[0166] Table 9: Control of Eleusine indica (ELEIN) with formulations containing 2602 dispersed with phosphate esters at 560 - 280 g / ha a.e. glyphosate - dicamba

[0167]

[0168] Example 7 - Preparation of formulations with increased amounts of surfactant

[0169] Formulations with increased levels of Crodafos O5A and Agnique PG 264 were also prepared. A series of formulations '531, '541, '551, '522, '532, '542, '523, '533, '524, '525 were prepared by taking the components shown in Table 10 and adding the balance of the basic formulation 8-1 (MEA dicamba, 56.19% ae + MEA glyphosate, 44.8% ae) microemulsified overnight at room temperature and 54 °C with and without 5% water, as shown in the table below.

[0170] Table 10: Formulations with Increased Crodafos O5A and Agnique PG 264

[0171]

[0172] Table 11: Dicamba - Glyphosate - Vaporgrip TM Specific Gravity and Loading of Formulations

[0173]

[0174] Table 12: Premix Formulation '542

[0175]

[0176] Table 13: High - Vaporgrip TM Formulations, Formulations 13 - 1 and 13 - 2

[0177]

[0178]

[0179] Table 13 shows Formulation 13 - 1, which is characterized by an acetic acid:dicamba ratio of 3.5:1, where dicamba / glyphosate a.e. is 9.5% / 21.7%, and contains a dye, an antifoaming agent (SAG 1572), and an iron safener.

[0180] Example 8 - Dicamba - Glufosinate and Vaporgrip TM Premix

[0181] Glufosinate - ammonium is dissolved in water and stirred, then potassium acetate is added and stirred until dissolved. 55% a.e. MEA dicamba is added together with drift reducer 2602 and emulsifier Crodafos, and stirred until homogeneous. A surfactant is added and stirred for at least 20 minutes.

[0182] Table 14: Dicamba - Glufosinate - ammonium Formulations with Vaporgrip and DRA

[0183]

[0184]

[0185] Table 15: Dicamba - Glufosinate - ammonium Formulations with Vaporgrip and DRA

[0186]

[0187]

[0188] Table 16: Dicamba - Glufosinate - ammonium Formulations with Vaporgrip and Drift Blocker

[0189]

[0190] Example 9 - Weed efficacy study:

[0191] A. Dicamba - Glyphosate and Vaporgrip TM premix

[0192] Greenhouse study:

[0193] The efficacy of formulations ‘541, ‘551, ‘542 and ‘533 (Table 11) was evaluated on ELEIN and ABUTH against Powermax / Xtendimax and first - generation Roundup Xtend (Table 18). The efficacy of the premix formulations using TDXL and TTI nozzles was also tested. All standards (including Roundup Xtend, Enlist Duo and tank - mix treatments) were sprayed only with the TTI nozzle, while the premix formulations were sprayed with TTI and TDXL nozzles. The application rate was 560 / 1120 g / ha ae dicamba / glyphosate. The comparison formulation was potassium glyphosate without any adjuvant. Overall, the four premix formulations performed very well compared to Roundup Xtend and PowerMax + Xtendimax tank mixtures. No significant difference was observed between the premix formulations using TTI and TEDx nozzles. Generally, in most cases, TTI was numerically superior to TDXL. Formulation ‘541 with a lower surfactant was weaker against weeds, but the other three formulations were comparable to each other and to the Powermax / Xtendimax control.

[0194] Field study:

[0195] Field experiments or trials were conducted at 16 Monsanto field locations. A group-unbalanced block (GUBD) design with three replications was used, with power greater than 80%, and an equivalence lower limit of -10 when LSD = 5 and δ < 5 were used for evaluation. Annual field preparation included fall disking, followed by spring disking. In addition to spring disking, if there were native weed populations, a non-residual burn-down chemical was applied at the labeled rate to start cleaning the field and ensure that any native weed bank was at the same growth stage as the planted weed species. Weed seeds (4 broadleaf and 4 grass species, species depending on location) were planted into 10 x 20 ft plots. When the weeds were measured at 4 - 7 inches tall, herbicide treatments were applied at 15 GPS using a CO2-pressurized backpack sprayer or a precision multi-nozzle boom sprayer equipped with Teejet TTI110015 nozzles. In all trials, visual weed control or growth inhibition ratings for each weed species were recorded on a scale of 0 to 100% at 14 days and 21 days after treatment (DAT), where 0 = no control or growth inhibition, and 100 = plant death. Data for different weed species within each weed group (i.e., broadleaf weeds and grass species) were analyzed. Trials and replications within the trials were considered random effects, and herbicide treatments were considered fixed effects.

[0196] As shown in Table 18, at 16 locations, the control percentages for broadleaf and grass species control of 20 treatments (including tank mixtures and 0.5X rates) were evaluated. Only entries 1 - 4 for broadleaf (dicamba alone controls) showed no significant difference in the average control of broadleaf among the 4 treatments. No significant activity in the average control percentage of entries 1 - 4 was observed on grass species. Entries 5 and 6 (glyphosate alone controls) showed no significant difference between treatments for broadleaf or grass species. Entries 7 - 14 (premixes and tank mixtures of dicamba and glyphosate) showed no significant difference from each other in average broadleaf control and were equivalent to the commercial tank mixture check of Xtendimax plus Roundup Powermax plus Intact. When looking at the individual species level, for broadleaf species, the only difference in equivalence was formulation '541, which was significantly lower in controlling redroot pigweed at the full rate; however, when applied at the half-X rate, it was equivalent to all other treatments. For individual grass species, the only significant difference was that the commercial control using the tank mixture of Xtendimax plus Roundup Powermax plus Intact had much lower control of Proso millet. The half-X rate was used to attempt to further differentiate between treatments; however, among both broadleaf and grass species control, all 0.5X entries (15 - 20) were equivalent to each other.

[0197] Table 17: Efficacy (% control) of glyphosate + dicamba premix formulations with built-in DRA

[0198]

[0199]

[0200] Table 18: Average post-emergence broadleaf control at 21 DAT for broadleaf and grass species control

[0201]

[0202]

[0203] Table 19: Greenhouse efficacy data for glufosinate / dicamba formulations in ABUTH, AMAPA, and PANMI

[0204]

[0205]

[0206] Table 20: Greenhouse crop safety data for glufosinate / dicamba formulations in GLXMA and GOSHI

[0207]

[0208]

[0209] Example 10 - Dicamba Microemulsion Composition with DRA and Vaporgrip TM ​

[0210] Mix acetic acid and potassium hydroxide in a given ratio, and then add other ingredients in no specific order to provide the microemulsion compositions shown in Tables 21 - 26 below.

[0211] Table 21: Dicamba microemulsion composition with DRA and 1:1 Vaporgrip TM : Dicamba ratio

[0212]

[0213]

[0214] Table 22: Dicamba microemulsion composition with DRA and 1.5:3.0 Vaporgrip TM : Dicamba ratio

[0215]

[0216] Table 23: Dicamba microemulsion composition with DRA and 2:1 Vaporgrip TM : Dicamba ratio

[0217]

[0218] Table 24: Dicamba Microemulsion Compositions with DRA and 0:1 - 2:1 Vaporgrip TM : Dicamba Ratio of Dicamba Microemulsion Compositions

[0219]

[0220]

[0221] Table 25: Dicamba Microemulsion Compositions with DRA and 2 - 4 Vaporgrip TM : Dicamba of Dicamba Microemulsion Compositions

[0222]

[0223] Table 26: Dicamba ME Compositions with Methyl Soyate / Soybean Oil and 2:1 Vaporgrip TM : Dicamba of Dicamba ME Compositions

[0224]

[0225]

[0226] Example 11 - Dicamba Microemulsion Composition with DRA and Vaporgrip TM Humidity Control Dome Volatility of Dicamba Microemulsion Composition

[0227] The humidity - controlled chamber volatility study was conducted as described in U.S. Patent No. 9,743,664, the entire content of which is incorporated herein by reference. The results are shown in Table 27 below.

[0228] Table 27: Dicamba MEA Compositions with DRA and 2:1 Vapor Grip and Dicamba Ratio

[0229]

[0230]

[0231] Table 28: Humidity - Controlled Chamber Volatility of Dicamba Microemulsions with DRA and 2:1 to 4:1 Vaporgrip TM : Dicamba Ratio

[0232]

[0233]

[0234] Example 12 - 2,4 - D and glyphosate microemulsion composition with DRA

[0235] Preparation method: Add water and DMAPA (3-(dimethylamino)-1-propanamine) into a glass bottle and stir until homogeneous. Then, add 2,4-D acid, and subsequently add the glyphosate acid wet cake and stir until completely dissolved. Then, add the drift retardant 2602 and the surfactant Crodafos TM O5A, and stir until a homogeneous solution is obtained. Finally, add PG PG8107 / AGM 550, and then stir for 20 minutes until a clear formulation is obtained. See, Table 29.

[0236] Table 29

[0237] Ingredient / Sample ID Composition 05 - 1 Composition 05 - 4 Composition 05 - 5 Composition 05 - 6 2,4 - D Tech(98.2%) 13.5％ 15.80％ 15.80％ 13.50％ Glyphosate wet cake(97.73%) 20.46％ 23.73％ 23.73％ 20.46％ DMAPA 11.22％ 13.08％ 13.08％ 11.22％ 2602 2.50％ 3.00％ 3.00％ 2.50％ Crodafos O5A 4.00％ 3.90％ 3.90％ 3.00％ Ethoquad C12 - - 2.00％ - Agnique PG 264 2.00％ 2.50％ 2.50％ 2.00％ Agnique PG 8107 - - - 4.00％ AGM 550 - - - 2.00％ Water 46.3％ 38.0％ 36.0％ 41.3％ Total 100.0％ 100.00％ 100.00％ 100.00％

[0238] This written description uses examples to disclose the invention, including the best mode, and also enables any person skilled in the art to practice the invention, including preparing and using any device or system and performing any combined method. The patent scope of the invention is defined by the claims and may include other embodiments that occur to those skilled in the art. If such other embodiments have structural elements that do not differ from the literal language of the claims, or if they include equivalent structural elements that do not have a substantial difference from the literal language of the claims, they are intended to be within the scope of the claims.

Claims

1. A herbicidal composition concentrate, comprising: (a) at least one auxin herbicide, wherein the at least one auxin herbicide is selected from the following: dicamba, agriculturally acceptable salts of dicamba, agriculturally acceptable esters of dicamba, 2,4-D, agriculturally acceptable salts of 2,4-D, agriculturally acceptable esters of 2,4-D, and combinations thereof; (b) at least one drift retardant, comprising: soybean oil or methyl ester of soybean oil in an amount of 80% to 95% by weight of the drift retardant; a compound according to Formula I in an amount of 0.25% to 10% by weight of the drift retardant: wherein n is 50–250, and the compound of Formula I is poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-; and a compound of Formula II in an amount of 3% to 50% by weight of the drift retardant where i + j + k = 10 to 50 and r + s + t = 3 to 12, and the compound of Formula II is the ester of octadecanoic acid, 12-hydroxy-, homopolymer, with α,α',α”-1,2,3-propanetriyl tris[ω-hydroxy poly(oxy-1,2-ethanediyl)], wherein the sum of all components in the drift retardant is equal to 100%; and (c) an emulsifier selected from the following: phosphate esters, alkyl polysaccharides, alkoxylated castor oils, and combinations thereof; and wherein the at least one auxin herbicide is present in an amount of 5% to 50% (acid equivalent weight) by weight of the composition concentrate; and wherein the at least one drift retardant is present in an amount of 2% to 10% by weight of the composition concentrate.

2. The herbicidal composition concentrate according to claim 1, wherein the at least one auxin herbicide is an agriculturally acceptable salt of dicamba, and the salt is selected from the following: N,N-[aminopropyl]methylamine salt, monoethanolamine salt, dimethylamine salt, isopropylamine salt, diethanolamine salt, potassium salt, sodium salt, and combinations thereof.

3. The herbicidal composition concentrate according to claim 1, further comprising at least one monocarboxylic acid or its monocarboxylate salt.

4. The herbicidal composition concentrate according to claim 3, wherein the at least one monocarboxylic acid or its monocarboxylate salt is present in an amount of 5% to 30% (acid equivalent weight) by weight of the composition concentrate.

5. The herbicidal composition concentrate according to claim 3 or claim 4, wherein the molar ratio of the at least one monocarboxylic acid or its monocarboxylate salt to the auxin herbicide is from 3:10 to 10:

1.

6. The herbicidal composition concentrate according to claim 3 or claim 4, wherein the monocarboxylic acid is acetic acid or the monocarboxylate salt is potassium acetate.

7. The herbicidal composition concentrate according to claim 3 or claim 4, wherein the emulsifier is present in an amount of 1% to 20% by weight of the composition concentrate.

8. The herbicidal composition concentrate according to claim 1, further comprising at least one other herbicide.

9. The herbicidal composition concentrate according to claim 8, wherein the at least one other herbicide is present in an amount of 10% to 50% (weight of acid equivalent) based on the weight of the composition concentrate.

10. The herbicidal composition concentrate according to claim 8 or claim 9, wherein the at least one other herbicide is selected from the following: glyphosate, agriculturally acceptable salts of glyphosate, glufosinate, agriculturally acceptable salts of glufosinate, and combinations thereof.

11. The herbicidal composition concentrate according to claim 1 or claim 2, wherein the composition concentrate is an emulsion or a microemulsion.

12. A method for preparing a herbicidal composition concentrate, the method comprising: mixing at least one auxin herbicide with at least one drift retardant and an emulsifier, wherein the at least one drift retardant comprises: soybean oil or methyl ester of soybean oil in an amount of 80% to 95% by weight of the drift retardant; a compound according to formula I in an amount of 0.25% to 10% by weight of the drift retardant: where n is 50–250, and the compound of formula I is poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-; and a compound of formula II in an amount of 3% to 50% by weight of the drift retardant where i + j + k = 10 to 50 and r + s + t = 3 to 12, and the compound of formula II is the ester of 12-hydroxyoctadecanoic acid, homopolymer, with α,α',α”-1,2,3-propanetriyl tris[ω-hydroxy poly(oxy-1,2-ethanediyl)], where the sum of all components in the drift retardant is equal to 100%; and wherein the emulsifier is selected from the following: phosphate esters, alkyl polysaccharides, alkoxylated castor oils, and combinations thereof, to form the herbicidal composition concentrate, wherein the at least one auxin herbicide is selected from the following: dicamba, agriculturally acceptable salts of dicamba, agriculturally acceptable esters of dicamba, 2,4-D, agriculturally acceptable salts of 2,4-D, agriculturally acceptable esters of 2,4-D, and combinations thereof, wherein the at least one auxin herbicide is present in an amount of 5% to 50% (weight of acid equivalent) based on the weight of the composition concentrate; and wherein the at least one drift retardant is present in an amount of 2% to 10% based on the weight of the composition concentrate.

13. The method according to claim 12, wherein the at least one auxin herbicide is an agriculturally acceptable salt of dicamba, and the salt is selected from the following: N,N-[aminopropyl]methylamine salt, monoethanolamine salt, dimethylamine salt, isopropylamine salt, diethanolamine salt, potassium salt, sodium salt, and combinations thereof.

14. The method according to claim 12 or claim 13, further comprising mixing the at least one auxin herbicide with water to form an aqueous solution before mixing with the at least one drift retardant and the emulsifier.

15. The method according to claim 12, further comprising mixing at least one monocarboxylic acid or its monocarboxylate salt with the at least one auxin herbicide, the at least one drift retardant, and the emulsifier.

16. The method according to claim 15, wherein the composition concentrate comprises the at least one monocarboxylic acid or its monocarboxylate salt in an amount of 5% to 30% (acid equivalent weight) based on the weight of the composition concentrate.

17. The method according to claim 15 or claim 16, wherein the molar ratio of the at least one monocarboxylic acid or its monocarboxylate salt to the auxin herbicide is from 3:10 to 10:

1.

18. The method according to claim 15 or claim 16, wherein the monocarboxylic acid is acetic acid or the monocarboxylate salt is potassium acetate.

19. The method according to claim 15 or claim 16, wherein the composition concentrate comprises the emulsifier in an amount of 1% to 20% based on the weight of the composition concentrate.

20. The method according to claim 12, further comprising mixing at least one other herbicide with the at least one auxin herbicide, the at least one drift retardant, and the emulsifier.

21. The method according to claim 20, wherein the composition concentrate comprises the at least one other herbicide in an amount of 15% to 60% (acid equivalent weight) based on the weight of the composition concentrate.

22. The method according to claim 20 or claim 21, wherein the at least one other herbicide is selected from the group consisting of glyphosate, agriculturally acceptable salts of glyphosate, glufosinate, agriculturally acceptable salts of glufosinate, and combinations thereof.

23. The method according to claim 12 or claim 13, wherein the composition concentrate formed is an emulsion or a microemulsion.

24. A drift retardant composition for preparing a herbicidal application mixture, the drift retardant composition comprising: (a) at least one drift retardant, comprising: soybean oil or methyl ester of soybean oil; and a compound of formula I and a compound of formula II, wherein the compound of formula I is poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-; and wherein the compound of formula II is the ester of 12-hydroxyoctadecanoic acid, homopolymer, with α,α',α”-1,2,3-propanetriyltri[ω-hydroxypoly(oxy-1,2-ethanediyl)]; and (b) an emulsifier selected from the group consisting of phosphate esters, alkyl polysaccharides, alkoxylated castor oils, and combinations thereof, wherein the at least one drift retardant comprises: soybean oil or methyl ester of soybean oil in an amount of 80% to 95% based on the weight of the drift retardant; the compound of formula I in an amount of 0.25% to 10% based on the weight of the drift retardant; and the compound of formula II in an amount of 3% to 50% based on the weight of the drift retardant, wherein the sum of all components in the drift retardant is equal to 100%.

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