Novel soluble liquid composition of saflufenacil, preparation method and use thereof

Abstract

The present invention relates to a soluble liquid (SL) composition comprising saflufenacil and an organic base. Optionally, the composition further comprises at least one agriculturally acceptable carrier and / or additive. The present invention also relates to the use of an amine salt of saflufenacil for preparing a soluble liquid composition.

Description

[0001] This application claims priority to U.S. Provisional Application No. 62 / 891,902, filed on August 26, 2019, the entire contents of which are hereby incorporated by reference. Technical Field

[0002] The present invention relates to a soluble liquid (SL) composition comprising saflufenacil and an organic base. Optionally, the composition further comprises at least one agriculturally acceptable carrier and / or additive. The present invention further relates to the use of an amine salt of saflufenacil for preparing a soluble liquid composition. Background of the Invention

[0004] The chemical name of saflufenacil is 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H-pyrimidine)]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide, and its structural formula (I) is as follows:

[0005]

[0006] Safensulfuron belongs to the pyrimidinedione and / or phenyluracil chemical group and is used as an herbicide, particularly as a foliar contact and residual broadleaf weed herbicide. It can be absorbed by leaves and roots, transported in the apoplast and restricted in phloem. Safensulfuron is applied to the leaves and used for residual control of broadleaf weeds, including glyphosate-resistant biotypes and ALS-resistant biotypes. Safensulfuron is an inhibitor of protoporphyrinogen oxidase and is applied pre-emergence to corn and sorghum at a rate of 50-125 g / ha; pre-planting for soybeans, cereals, cotton, legumes for rapid foliar burn-down, and post-orientation to tree fruit and tree nuts at a rate of 18-25 g / ha.

[0007] Saflufenacil is disclosed in WO 2001 / 083459. Further methods for its preparation are disclosed in WO 2003 / 097589, WO 2005 / 054208 and WO 2006 / 097589 and in the earlier international application PCT / EP2006 / 062414.

[0008] Saflufenacil prepared by the above method is amorphous and extremely difficult to formulate.

[0009] Safensulfuron is almost insoluble in various liquid media, so creating a stable liquid formulation is a challenge. In particular, safensulfuron has a tendency to precipitate from most solvents, organic or aqueous media; the solubility of safensulfuron in water is 0.0025 g / 100 mL at pH 5 and 0.21 g / 100 mL at pH 7, both at 20°C. In acetonitrile, the solubility of safensulfuron at 20°C is 19.4 g / 100 mL. In acetone, the solubility of safensulfuron at 20°C is 27.5 g / 100 mL. In ethyl acetate, the solubility of safensulfuron at 20°C is 6.55 g / 100 mL. In tetrahydrofuran, the solubility of safensulfuron at 20°C is 36.2 g / 100 mL. In methanol, the solubility of safensulfuron at 20°C is 2.98 g / 100 mL. In isopropanol, the solubility of saflufenacil at 20°C is 0.25 g / 100 mL. In toluene, the solubility of saflufenacil at 20°C is 0.23 g / 100 mL. In 1-octanol, the solubility of saflufenacil at 20°C is <0.01 g / 100 mL. In n-heptane, the solubility of saflufenacil at 20°C is <0.005 g / 100 mL.

[0010] Furthermore, the two crystalline modifications of saflufenacil known in the art, saflufenacil form II and the crystalline form of saflufenacil hydrate disclosed in WO 2008 / 043835 and WO 2008 / 043836, are poorly soluble in aqueous media, which can cause problems for formulation.

[0011]

[0006] Therefore, there is a need in the art for anhydrous saflufenacil formulations in non-aqueous media that exhibit improved properties including, for example, improved stability and solubility in water. Summary of the invention

[0012] The present invention provides a soluble liquid (SL) composition comprising (i) a certain amount of saflufenacil, and (ii) a certain amount of an organic base.

[0013] The present subject matter also provides a soluble liquid (SL) composition comprising (i) an amount of saflufenacil, (ii) an amount of 2,4-D, and (iii) an amount of an organic base.

[0014] The present invention also provides a combination comprising:

[0015] (i) a certain amount of saflufenacil, and

[0016] (ii) a certain amount of organic base.

[0017] The present invention also provides a combination comprising:

[0018] (i) an amount of any one of the SL compositions disclosed herein, and

[0019] (ii) an amount of at least one additional pesticide.

[0020] The present invention also provides a combination comprising:

[0021] (i) an amount of any one of the SL compositions disclosed herein, and

[0022] (ii) an amount of at least one additional pesticide,

[0023] The combination is more effective in controlling and / or preventing pests than when the same amount of each pesticide is applied alone.

[0024] The present invention also provides a combination comprising:

[0025] (i) an amount of any one of the SL compositions disclosed herein, and

[0026] (ii) an amount of at least one additional pesticide,

[0027] wherein said amount of saflufenacil and said amount of another pesticide, when applied together, are more effective for controlling and / or preventing pests than when the same amount of each pesticide is applied alone.

[0028] The present invention also provides a combination comprising:

[0029] (i) an amount of any one of the SL compositions disclosed herein, and

[0030] (ii) an amount of at least one additional pesticide,

[0031] wherein the amount of saflufenacil in the combination is less than the pesticide effective amount of saflufenacil when saflufenacil is used alone, and / or

[0032] The amount of the additional pesticide in the combination is less than the pesticidally effective amount of the additional pesticide when the additional pesticide is used alone.

[0033] The present invention also provides a mixture comprising any one of the combinations disclosed herein.

[0034] The present invention also provides a SL composition comprising any one of the combinations or mixtures disclosed herein.

[0035] The present invention also provides a method for controlling and / or preventing pests, comprising applying an effective amount of any one of the SL compositions, combinations or mixtures disclosed herein to a locus where pests are to be controlled and / or prevented, thereby controlling and / or preventing pests.

[0036] The present invention also provides a method for controlling weeds, comprising applying an effective amount of any one of the SL compositions, combinations or mixtures disclosed herein to a locus where weeds are to be controlled, thereby controlling the weeds.

[0037] The present invention also provides a method for controlling weeds in a crop field, comprising applying an effective amount of any one of the SL compositions, combinations or mixtures disclosed herein to the crop field, thereby controlling the weeds in the crop field.

[0038] The present invention also provides use of any one of the SL compositions, combinations or mixtures disclosed herein for controlling and / or preventing pests, comprising applying an effective amount of any one of the SL compositions, combinations or mixtures disclosed herein to a locus where pests are to be controlled and / or prevented.

[0039] The present invention also provides use of any one of the SL compositions or mixtures disclosed herein for controlling weeds, comprising applying an effective amount of any one of the SL compositions, combinations or mixtures disclosed herein to a locus where weeds are to be controlled.

[0040] The present invention also provides any one of the SL compositions, combinations or mixtures disclosed herein for use in controlling and / or preventing pests, comprising applying any one of the SL compositions, combinations or mixtures disclosed herein to a locus where pests are to be controlled and / or prevented.

[0041] The present invention also provides any one of the SL compositions or mixtures disclosed herein for use in controlling weeds, comprising applying an effective amount of any one of the SL compositions, combinations or mixtures disclosed herein to a locus where weeds are to be controlled.

[0042] The present invention also provides a package comprising any one of the SL compositions, combinations or mixtures disclosed herein.

[0043] The present invention also provides a use of an amine salt of saflufenacil for preparing a soluble liquid composition.

[0044] The present invention also provides an amine salt of saflufenacil, which is used for preparing a soluble liquid composition.

[0045] The present invention also provides a method for preparing any one of the SL compositions disclosed herein, wherein the method comprises:

[0046] (i) obtaining a certain amount of saflufenacil and a certain amount of organic base.

[0047] (ii) mixing the saflufenacil obtained in step (i) with an organic base to obtain a SL composition. BRIEF DESCRIPTION OF THE DRAWINGS

[0048] Figure 1 show Efficacy of LQ, saflufenacil 160SL (A) and saflufenacil 160SL (B) on Chenopodium album 3, 7 and 18 days after post-emergence spray application.

[0049] Figure 2 show Efficacy of LQ, saflufenacil 160SL (A) and saflufenacil 160SL (B) on Xanthium strumarium 3, 7 and 18 days after post-emergence spray application.

[0050] Figure 3 show Efficacy of LQ, saflufenacil 160SL (A) and saflufenacil 160SL (B) on Solanum nigrum 3, 7 and 18 days after post-emergence spray application.

[0051] Figure 4 show Efficacy of LQ, saflufenacil 160SL(B) and saflufenacil 160SL(B) blank on Chenopodium album at 3, 10 and 18 days after post-emergence spray application.

[0052] Figure 5 show Efficacy of LQ, saflufenacil 160SL(B) and saflufenacil 160SL(B) blank on Solanum nigrum 3, 10 and 18 days after post-emergence spray application. DETAILED DESCRIPTION

[0053] SL compositions are convenient to use because they can be applied directly after dilution with water. The formulation of SL compositions of saflufenacil is challenging because saflufenacil is not soluble in water or many other solvents commonly used in agricultural formulations. In addition, saflufenacil is chemically sensitive to water at neutral or alkaline pH.

[0054] A novel soluble liquid composition of saflufenacil is described herein. The novel soluble liquid composition comprises saflufenacil and an organic base. Without wishing to be bound by any theory, it is hypothesized that saflufenacil and the organic base form a complex based on electrostatic forces between saflufenacil and the organic base and the stereochemical properties of saflufenacil. The formation of the complex stabilizes saflufenacil in the presence of water. The saflufenacil-organic base complex has a high solubility in water. The formulation of the complex also prevents the sedimentation of saflufenacil in the SL composition and after the SL composition is diluted with water. The novel soluble liquid composition also allows for high-load saflufenacil compositions.

[0055] definition

[0056] Unless defined otherwise, 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 subject matter belongs.

[0057] As used herein, the term "composition" comprises a mixture or mixtures of a crystalline form of saflufenacil and another component, such as an organic base. In some embodiments, the composition may comprise at least one additional pesticide.

[0058] As used herein, the term "soluble liquid composition" or "SL composition" refers to a liquid, homogeneous formulation. The SL composition forms a clear solution upon dilution in water. Preferably, the SL composition is free of water. Preferably, the SL composition comprises an organic base and an active ingredient dissolved in the organic base, such as saflufenacil.

[0059] As used herein, the term "high loading" means that when used in conjunction with a composition or SL composition, the amount of saflufenacil dissolved in the organic base of the composition is greater than 7 wt %, based on the total weight of the composition.

[0060] As used herein, the term "agriculturally acceptable carrier" refers to solvents known and accepted in the art for forming compositions for agricultural or horticultural use.

[0061] As used herein, the term "additive" refers to any substance that is not an active ingredient itself but is added to a composition. Examples of additives include, but are not limited to, adjuvants, surfactants, emulsifiers, antifreeze agents, defoamers, and preservatives.

[0062] As used herein, the term "excipient" refers to any chemical that has no appreciable pesticidal activity, such as a surfactant, solvent, or adjuvant. One or more excipients may be added to any composition disclosed herein.

[0063] As used herein, the term "stable" when used in conjunction with a composition means that the composition is physically and chemically stable. As used herein, the term "chemically stable" means that no significant decomposition of the active ingredient is observed after storage in a closed package at a temperature of 54°C for at least 2 weeks. As used herein, the term "physically stable" means that no significant sedimentation is observed after storage in a closed package at a temperature of 54°C for at least 2 weeks.

[0064] Stability can be assessed according to the test protocol developed by the International Pesticide Analysis Cooperative Committee (CIPAC). Stability can be assessed under normal storage conditions after two years of storage at room temperature. Stability can also be assessed under accelerated storage conditions, i.e. after 2 weeks of storage at 54°C, or after 8 weeks of storage at 40°C, or after 12 weeks of storage at 35°C, or after 3 months of storage at room temperature, or after 2 weeks of storage at 0°C.

[0065] As used herein, the term "mixture" refers to, but is not limited to, a combination in any physical form, such as a blend, a solution, an alloy, and the like.

[0066] As used herein, the term "combination" refers to the application of a collection of agricultural chemicals by simultaneous or synchronous application.

[0067] As used herein, the term "simultaneously" when used in conjunction with the application of an agricultural chemical means that the agricultural chemical is applied in an admixture, e.g., a tank mix. For simultaneous application, the combination can be an admixture or each separate container containing the agricultural chemical is combined prior to application.

[0068] As used herein, the term "simultaneously" when used in conjunction with the application of agricultural chemicals refers to the separate application of a separate agricultural chemical and another agricultural chemical or premix at the same time or sufficiently close in time to achieve at least one advantage from the combination of the agricultural chemicals, for example, an additive or more than additive or synergistic activity relative to the activity of either active ingredient at the same dose if the two active ingredients are applied simultaneously.

[0069] As used herein, the term "tank mix" refers to mixing one or more components of the composition of the present invention in a spray tank at the time of spray application or prior to spray application.

[0070] As used herein, the term "effective" when used in conjunction with the amount of a combination, mixture or composition means that the amount of the combination, mixture or composition achieves an agriculturally beneficial level of control and / or prevention of pests when applied to the locus where the pests are to be controlled and / or prevented.

[0071] As used herein, the term "effective amount" refers to the amount of an active ingredient commercially recommended for controlling and / or preventing pests. The commercially recommended amount of each active ingredient, usually specified as an application rate for a commercial formulation, can be found on the label accompanying the commercial formulation. The commercially recommended application rate of a commercial formulation may vary depending on factors such as the plant species and the pest to be controlled.

[0072] As used herein, the term "more effectively controlling pests" includes, but is not limited to, increasing the effectiveness of controlling pests and reducing the amount of time required to achieve a specified level of pest control.

[0073] As used herein, the term "more effectively preventing pests" includes, but is not limited to, improving the efficacy of preventing pest infestation and extending the protection period against pest infestation after application.

[0074] As used herein, the term "pest" includes, but is not limited to, unwanted fungi, unwanted insects, unwanted nematodes, and weeds.

[0075] As used herein, the term "weeds" includes any unwanted vegetation.

[0076] As used herein, the term "pesticide" broadly refers to an agent that can be used to prevent, control and / or kill pests. The term should be understood to include, but is not limited to, fungicides, insecticides, nematicides, herbicides, miticides, parasiticides or other control agents. For chemical classes and applications and specific compounds of each class, 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 each document are incorporated herein by reference in their entirety.

[0077] As used herein, the term "location" includes not only areas where pests may have occurred, but also areas where pests have not yet occurred, and areas under cultivation. Locations include plants or crops and propagation materials of the plants or crops. Locations also include areas around plants or crops and growing media for plants or crops, such as soil and crop fields.

[0078] As used herein, the term "plant" or "crop" includes whole plants, plant organs (e.g., leaves, stems, twigs, roots, trunks, branches, shoots, fruits, etc.), plant cells or plant seeds. The term encompasses plant crops, such as fruits.

[0079] As used herein, the term "propagation material" of a plant or crop may include all reproductive parts of a plant or crop, such as seeds and vegetative 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 seedlings, which are transplanted after germination or after emergence from the soil.

[0080] As used herein, the term "ha" refers to hectares.

[0081] As used herein, the terms "a" and "an" include both the singular and the plural. Therefore, the terms "a" or "at least one" can be used interchangeably in this application.

[0082] Throughout the application, the description of various embodiments uses the term "comprising"; however, those skilled in the art will appreciate that in some specific cases, the expressions "consisting essentially of" or "consisting of" may be used to describe the embodiments.

[0083] The term "about" herein specifically includes a range of ±10% of the indicated value. In addition, the endpoints of all ranges referred to herein for the same component or property are inclusive of the endpoints, independently combinable, and include all intermediate points and ranges.

[0084] It should be understood that where a parameter range is provided, the present invention also provides all integers and tenths thereof within the range, just as if they were exactly described herein. For example, "0.1% to 70%" includes 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, etc. up to 70%.

[0085] All publications, patents, and patent applications mentioned in this specification are herein incorporated by reference in their entirety into the specification, to the same extent as if each individual publication, patent, or patent application was specifically and individually indicated to be incorporated by reference.

[0086] The following examples illustrate the practice of this theme in some of its embodiments, but should not be construed as limiting the scope of this theme. For those of ordinary skill in the art, other embodiments that are obvious from consideration of the present specification and examples and fall within the spirit and scope of the appended claims are part of the present invention. The description (including the examples) is exemplary only and does not limit the scope and spirit of the present invention.

[0087] Various aspects and embodiments of the invention will now be described.

[0088] The present invention provides a soluble liquid (SL) composition comprising (i) a certain amount of saflufenacil and (ii) a certain amount of an organic base.

[0089] In some embodiments, the SL composition is stable. In some embodiments, the SL composition has low persistent foam.

[0090] In some embodiments, the amount of saflufenacil is dissolved in an organic base.

[0091] In some embodiments, the organic base is an amine.

[0092] In some embodiments, the amine is a primary amine. In some embodiments, the amine is a secondary amine. In some embodiments, the amine is a cyclic amine. In some embodiments, the cyclic amine is an aromatic amine.

[0093] In some embodiments, the primary amine is R1-NH2, wherein R1 is C1-C6 alkyl. In some embodiments, R1 of the primary amine is C4 alkyl. In some embodiments, the alkyl is straight chain. In some embodiments, the alkyl is branched. In some embodiments, R1 of the primary amine is butyl.

[0094] In some embodiments, the secondary amine is R1-NH-R2, wherein R1 and R2 are each C1-C3 straight chain alkyl. In some embodiments, R1 and R2 of the secondary amine are both methyl. In some embodiments, R1 and R2 of the secondary amine are both ethyl. In some embodiments, R1 and R2 of the secondary amine are both propyl. In some embodiments, the alkyl is substituted with an OH group. In some embodiments, R1 and R2 of the secondary amine are both ethanol groups.

[0095] In some embodiments, the pKa of the amine is in the range of 4-11. In some embodiments, the pKa of the amine is about 5. In some embodiments, the pKa of the amine is in the range of 8-9. In some embodiments, the pKa of the amine is in the range of 10-11.

[0096] In some embodiments, the amine is selected from pyridine, diethanolamine, dimethylamine in tetrahydrofuran (THF), butylamine, dipropylamine, ethoxylated fatty acid amines, and any combination thereof. In some embodiments, the amine is pyridine. In some embodiments, the amine is diethanolamine. In some embodiments, the amine is dimethylamine in tetrahydrofuran (THF). In some embodiments, the amine is the butylamine. In some embodiments, the amine is dipropylamine. In some embodiments, the amine is an ethoxylated fatty acid amine. In some embodiments, the ethoxylated fatty acid amine is an ethoxylated coconut fatty acid amine. In some embodiments, the ethoxylated fatty acid amine is ethoxylated with more than 5 ethylene oxides. In some embodiments, the ethoxylated fatty acid amine is ethoxylated with more than 10 ethylene oxides. In some embodiments, the ethoxylated fatty acid amine is ethoxylated with 15 or more ethylene oxides.

[0097] In some embodiments, the amine is sold by Clariant.In C 200. In some embodiments, the amine is sold by Clariant.In C 150. In some embodiments, the amine is sold by Clariant.In C 100. In some embodiments, the amine is sold by Clariant.In C 050. In some embodiments, the amine is sold by Clariant.In C020. In some embodiments, the amine is sold by Clariant.In addition to Amines other than C 050.

[0098] In some embodiments, the amine has the structure:

[0099]

[0100] In some embodiments, the amine is an amine other than aniline, triisopropanolamine, monoethanolamine, triethylamine, diisopropylamine, or dibutylamine.

[0101] In one embodiment, the present invention provides a soluble liquid (SL) composition comprising (i) a certain amount of saflufenacil and (ii) a certain amount of an organic base, wherein the organic base is selected from pyridine, diethanolamine, dimethylamine in tetrahydrofuran (THF), butylamine, dipropylamine, ethoxylated fatty acid amines, and any combination thereof.

[0102] In some embodiments, the amount of saflufenacil in the SL composition is from about 0.1% by weight to about 70% by weight, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is from 0.1% by weight to 70% by weight, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is from about 1% by weight to about 30% by weight, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is from about 10% by weight to about 20% by weight, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is about 15% by weight, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is about 16% by weight, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is 15.38% by weight, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is from about 1% by weight to about 10% by weight, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is from about 1 wt % to about 5 wt %, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is about 3 wt %, based on the total weight of the composition.

[0103] In some embodiments, the amount of saflufenacil in the SL composition is at least 7 wt %, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is greater than 7 wt %, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is greater than 10 wt %, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is greater than 15 wt %, based on the total weight of the composition. In some embodiments, the SL composition is a high-loaded composition.

[0104] In some embodiments, the amount of saflufenacil in the SL composition is less than 60 wt%, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is less than 30 wt%, based on the total weight of the composition. In some embodiments, the amount of saflufenacil in the SL composition is less than 15 wt%, based on the total weight of the composition.

[0105] In some embodiments, a certain amount of saflufenacil in the SL composition described herein refers to the amount of saflufenacil dissolved in the organic base of the SL composition.

[0106] In some embodiments, the amount of organic base in the SL composition is from about 0.1 wt % to about 80 wt %, based on the total weight of the composition. In some embodiments, the amount of organic base in the SL composition is from about 40 wt % to about 80 wt %, based on the total weight of the composition. In some embodiments, the amount of organic base in the SL composition is from about 50 wt % to about 70 wt %, based on the total weight of the composition. In some embodiments, the amount of organic base in the SL composition is from about 60 wt % to about 65 wt %, based on the total weight of the composition. In some embodiments, the amount of organic base in the SL composition is 61 wt %, based on the total weight of the composition. In some embodiments, the amount of organic base in the SL composition is 62 wt %, based on the total weight of the composition. In some embodiments, the amount of organic base in the SL composition is 61.54 wt %, based on the total weight of the composition. In some embodiments, the amount of organic base in the SL composition is from about 10 wt % to about 15 wt %, based on the total weight of the composition. In some embodiments, the amount of organic base in the SL composition is 13 wt %, based on the total weight of the composition.

[0107] In some embodiments, the ratio of saflufenacil and the organic base in the composition is such that the ratio of amine groups to saflufenacil molecules is at least 1:1.

[0108] In some embodiments, the SL composition comprises an amount of at least one agriculturally acceptable carrier. In some embodiments, the agriculturally acceptable carrier is water soluble. In some embodiments, the SL composition comprises at least one water soluble agriculturally acceptable carrier. In some embodiments, the agriculturally acceptable carrier is a solvent or a cosolvent. In some embodiments, the agriculturally acceptable carrier is a dimethylamide ester. In some embodiments, the agriculturally acceptable carrier is PolarClean, sold by Solvay.

[0109] In some embodiments, the agriculturally acceptable carrier is

[0110]

[0111] Examples of suitable agriculturally acceptable carriers for the composition may include aromatic hydrocarbons, such as alkylbenzenes and alkylnaphthalenes; alcohols, such as methanol, cyclohexanol and decanol, ethylene glycol, polypropylene glycol and dipropylene glycol; N,N-dimethylformamide, dimethylamide esters (such as PolarClean), dimethyl sulfoxide, N-alkyl pyrrolidone, paraffin, olive oil, castor oil, linseed oil, tung oil, sesame oil, corn oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil and coconut oil, fatty acid esters; ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, etc.

[0112] In some embodiments, the amount of the agriculturally acceptable carrier in the SL composition is from about 0.1% to about 90% by weight, based on the total weight of the composition. In some embodiments, the amount of the agriculturally acceptable carrier in the SL composition is from about 1% to about 40% by weight, based on the total weight of the composition. In some embodiments, the amount of the agriculturally acceptable carrier in the SL composition is from about 10% to about 30% by weight, based on the total weight of the composition. In some embodiments, the amount of the agriculturally acceptable carrier in the SL composition is from about 20% to about 25% by weight, based on the total weight of the composition. In some embodiments, the amount of the agriculturally acceptable carrier in the SL composition is about 23% by weight, based on the total weight of the composition. In some embodiments, the amount of the agriculturally acceptable carrier in the SL composition is 23.08% by weight, based on the total weight of the composition. In some embodiments, the amount of the agriculturally acceptable carrier in the SL composition is from about 1% to about 10% by weight, based on the total weight of the composition. In some embodiments, the amount of the agriculturally acceptable carrier in the SL composition is about 8% by weight, based on the total weight of the composition. In some embodiments, the amount of the agriculturally acceptable carrier in the SL composition is 7.8 wt %, based on the total weight of the composition.

[0113] In some embodiments, the SL composition does not include an agriculturally acceptable carrier.

[0114] In some embodiments, the SL composition comprises an amount of at least one additive.

[0115] In some embodiments, the additive is selected from the group consisting of an adjuvant, a surfactant, an emulsifier, an antifreeze agent, an antifoaming agent, a preservative, and any combination thereof.

[0116] Other ingredients, such as wetting agents, binders, neutralizers, thickeners, adhesives, chelating agents, stabilizers, solubilizers, salts and / or fertilizers, may also be added to the disclosed compositions.

[0117] In some embodiments, the additive is an emulsifier. In some embodiments, the emulsifier is PEG-36 castor oil. In some embodiments, the emulsifier is Emulsogen EL 360, sold by Clariant.

[0118] In some embodiments, the additive is a surfactant.

[0119] Examples of suitable surfactants include nonionic, anionic, cationic and amphoteric types, such as alkoxylated fatty alcohols, ethoxylated fatty acid amines, ethoxylated polysorbates (such as Tween 20), ethoxylated castor oil, lignin sulfonates, fatty acid sulfonates (such as lauryl sulfonate), phosphates, such as phosphates of alcohol alkoxylates, phosphates of alkylphenol alkoxylates and phosphates of styrylphenol ethoxylates, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, alkylarylsulfonates, ethoxylated alkylphenols and arylphenols, polyalkylene glycols and sorbitan esters.

[0120] In some embodiments, the additive is a nonionic surfactant. In some embodiments, the surfactant is calcium alkylbenzene sulfonate. In some embodiments, the surfactant is EVM70-2E, sold by Huntsman.

[0121] In some embodiments, the amount of one or more additives in the SL composition is from about 1 wt % to about 80 wt %, based on the total weight of the composition. In some embodiments, the amount of one or more additives in the SL composition is from about 1 wt % to about 50 wt %, based on the total weight of the composition. In some embodiments, the amount of one or more additives in the SL composition is from about 1 wt % to about 30 wt %, based on the total weight of the composition. In some embodiments, the amount of one or more additives in the SL composition is from about 1 wt % to about 10 wt %, based on the total weight of the composition. In some embodiments, the amount of one or more additives in the SL composition is from about 5 wt % to about 10 wt %, based on the total weight of the composition. In some embodiments, the amount of one or more additives in the SL composition is about 6 wt %, based on the total weight of the composition. In some embodiments, the amount of one or more additives in the SL composition is 6.2 wt %, based on the total weight of the composition.

[0122] In some embodiments, the amount of emulsifier in the SL composition is from about 1 wt % to about 10 wt %, based on the total weight of the composition. In some embodiments, the amount of emulsifier in the SL composition is from about 1 wt % to about 5 wt %, based on the total weight of the composition. In some embodiments, the amount of emulsifier in the SL composition is about 4 wt %, based on the total weight of the composition. In some embodiments, the amount of emulsifier in the SL composition is 3.7 wt %, based on the total weight of the composition.

[0123] In some embodiments, the amount of surfactant in the SL composition is from about 1 wt % to about 10 wt %, based on the total weight of the composition. In some embodiments, the amount of surfactant in the SL composition is from about 1 wt % to about 5 wt %, based on the total weight of the composition. In some embodiments, the amount of surfactant in the SL composition is about 2.5 wt %, based on the total weight of the composition.

[0124] In some embodiments, the SL composition comprises an amount of at least one additional pesticide.

[0125] In some embodiments, the additional pesticide is a herbicide. In some embodiments, the herbicide is selected from 2,4-D, imazethapyr, pyroxasulfone, S-metolachlor, glufosinate, halauxifen, glyphosate, carfentrazone, sulfentrazone, dimethenamide-P, mesotrione, metribuzin, and bicycopyrone. In some embodiments, the herbicide is 2,4-D.

[0126] In some embodiments, the amount of additional pesticide in the SL composition is from about 1 wt % to about 80 wt %, based on the total weight of the composition. In some embodiments, the amount of additional pesticide in the SL composition is from about 60 wt % to about 80 wt %, based on the total weight of the composition. In some embodiments, the amount of additional pesticide in the SL composition is about 70 wt %, based on the total weight of the composition.

[0127] In some embodiments, the composition comprising additional pesticides is more effective for controlling and / or preventing pests than when the same amount of each pesticide is applied alone.

[0128] In some embodiments, the amount of saflufenacil and the amount of the additional pesticide in the composition, when applied together, are more effective for controlling and / or preventing pests than when the same amount of each pesticide is applied alone.

[0129] In some embodiments, the amount of saflufenacil in the composition is less than the pesticidally effective amount of saflufenacil when used alone. In some embodiments, the amount of the additional pesticide in the composition is less than the pesticidally effective amount of the additional pesticide when used alone.

[0130] In some embodiments, the pest is a weed.

[0131] The present subject matter also provides a soluble liquid composition comprising (i) an amount of saflufenacil, (ii) an amount of 2,4-D, and (iii) an amount of an organic base.

[0132] In some embodiments, the SL composition comprises:

[0133] (i) about 15% by weight of saflufenacil, based on the total weight of the composition,

[0134] (ii) about 62 weight percent of an amine, based on the total weight of the composition, and

[0135] (iii) about 23% by weight of an agriculturally acceptable carrier, based on the total weight of the composition.

[0136] In some embodiments, the SL composition comprises:

[0137] (i) about 15% by weight of saflufenacil, based on the total weight of the composition,

[0138] (ii) about 62% by weight C150, based on the total weight of the composition, and

[0139] (iii) about 23% by weight PolarClean, based on the total weight of the composition.

[0140] In some embodiments, the SL composition comprises:

[0141] (i) 15.38% by weight of saflufenacil, based on the total weight of the composition,

[0142] (ii) 61.54% by weight C150, based on the total weight of the composition, and

[0143] (iii) 23.08 wt% PolarClean, based on the total weight of the composition.

[0144] In some embodiments, the SL composition comprises:

[0145] (i) about 15% by weight of saflufenacil, based on the total weight of the composition,

[0146] (ii) about 62 weight percent of diethanolamine, based on the total weight of the composition, and

[0147] (iii) about 23% by weight PolarClean, based on the total weight of the composition.

[0148] In some embodiments, the SL composition comprises:

[0149] (i) 15.38% by weight of saflufenacil, based on the total weight of the composition,

[0150] (ii) 61.54 wt. % of diethanolamine, based on the total weight of the composition, and

[0151] (iii) 23.08 wt% PolarClean, based on the total weight of the composition.

[0152] In some embodiments, the SL composition comprises:

[0153] (i) about 3% by weight of saflufenacil, based on the total weight of the composition,

[0154] (ii) about 70 weight percent 2,4-D, based on the total weight of the composition,

[0155] (iii) about 13 weight percent of an amine, based on the total weight of the composition,

[0156] (iv) about 4 wt. % of an emulsifier, based on the total weight of the composition,

[0157] (v) about 2.5 weight percent, based on the total weight of the composition, of a surfactant, and

[0158] (vi) about 8 weight percent of an agriculturally acceptable carrier, based on the total weight of the composition.

[0159] In some embodiments, the SL composition comprises:

[0160] (i) about 3% by weight of saflufenacil, based on the total weight of the composition,

[0161] (ii) about 70 weight percent 2,4-D, based on the total weight of the composition,

[0162] (iii) about 13% by weight C 050, based on the total weight of the composition,

[0163] (iv) about 4% by weight of Emulsogen EL 360, based on the total weight of the composition,

[0164] (v) about 2.5% by weight EVM 70-2E, based on the total weight of the composition, and

[0165] (vi) about 8% by weight PolarClean, based on the total weight of the composition.

[0166] In some embodiments, the SL composition comprises:

[0167] (i) about 3% by weight of saflufenacil, based on the total weight of the composition,

[0168] (ii) about 70 weight percent 2,4-D, based on the total weight of the composition,

[0169] (iii) about 13% by weight C 050, based on the total weight of the composition,

[0170] (iv) about 3.7% by weight of Emulsogen EL 360, based on the total weight of the composition,

[0171] (v) about 2.5% by weight EVM 70-2E, based on the total weight of the composition, and

[0172] (vi) about 7.8% by weight PolarClean, based on the total weight of the composition.

[0173] In some embodiments, the SL composition is non-aqueous. In some embodiments, the SL composition is substantially free of water. In some embodiments, the SL composition is anhydrous.

[0174] As will be readily appreciated, any materials that can be added to the disclosed compositions as herbicides may be used so long as they produce the desired effect without significantly interfering with such compositions (including synergistic compositions).

[0175] The disclosed composition may optionally include a combination that may contain at least 1% by weight of one or more compositions and another pesticide compound. This additional pesticide compound may be a herbicide, fungicide, insecticide, nematicide, acaricide, arthropodicide, bactericide, or a combination thereof, which is compatible with the synergistic composition of the present disclosure in the medium selected for application and does not antagonize the activity of the present compound. Therefore, in such an embodiment, the other pesticide compound is used as a supplemental toxicant for the same or different pesticide uses. The pesticide compound and the synergistic composition can generally be mixed together in a weight ratio of 1:100 to 100:1.

[0176] The present invention also provides a combination comprising:

[0177] (i) a certain amount of saflufenacil, and

[0178] (ii) a certain amount of organic base.

[0179] The present invention also provides a combination comprising:

[0180] (i) an amount of any one of the SL compositions disclosed herein, and

[0181] (ii) an amount of at least one additional pesticide.

[0182] In some embodiments, the combination is more effective for controlling and / or preventing pests than the same amount of each pesticide applied alone.

[0183] In some embodiments, the amount of saflufenacil and the amount of the additional pesticide, when applied together, are more effective for controlling and / or preventing pests than when the same amount of each pesticide is applied alone.

[0184] In some embodiments, the amount of saflufenacil in the combination is less than the pesticidally effective amount of saflufenacil when used alone, and / or the amount of the additional pesticide in the combination is less than the pesticidally effective amount of the additional pesticide when used alone.

[0185] In some embodiments, the additional pesticide is a herbicide. In some embodiments, the herbicide is selected from 2,4-D, imazethapyr, sulfonepyrazone, S-isopropylamine, glufosinate, fluclopyralid, glyphosate, triadimefon, sulfentrazone, methacetamiprid-P, mesotrione, metribuzin, and flumetrazol.

[0186] In some embodiments, saflufenacil and the additional pesticide act synergistically. A synergistic effect occurs when the effect of two or more compounds exceeds the effect of the compounds when used alone.

[0187] The present subject matter also provides a mixture comprising any one of the combinations disclosed herein.

[0188] The present subject matter also provides a mixture comprising any one of the SL compositions disclosed herein.

[0189] The present subject matter also provides a mixture comprising any one of the SL compositions disclosed herein and an amount of at least one additional pesticide.

[0190] In some embodiments, the additional pesticide is a herbicide. In some embodiments, the herbicide is selected from 2,4-D, imazethapyr, sulfonepyrazone, S-isopropylamine, glufosinate, fluclopyralid, glyphosate, triadimefon, sulfentrazone, methacetamidosulf-P, mesotrione, metribuzin, and flupyralid. In some embodiments, the herbicide is 2,4-D.

[0191] In some embodiments, the mixture is a tank mix.

[0192] In some embodiments, the mixture is more effective for controlling and / or preventing pests than when the same amount of each pesticide is applied alone.

[0193] In some embodiments, the amount of saflufenacil and the amount of the additional pesticide in the mixture, when applied together, are more effective for controlling and / or preventing pests than when the same amount of each pesticide is applied alone.

[0194] In some embodiments, the amount of saflufenacil in the mixture is less than the pesticidally effective amount of saflufenacil when used alone. In some embodiments, the amount of the additional pesticide in the mixture is less than the pesticidally effective amount of the additional pesticide when used alone.

[0195] In some embodiments, the pest is a weed.

[0196] The present invention also provides a SL composition comprising any one of the combinations disclosed herein.

[0197] The present invention also provides a SL composition comprising any one of the mixtures disclosed herein.

[0198] The present invention also provides a method for controlling and / or preventing pests, comprising applying an effective amount of any one of the SL compositions, mixtures or combinations disclosed herein to a locus where pests are to be controlled and / or prevented, thereby controlling and / or preventing pests.

[0199] In some embodiments, the pest is a weed.

[0200] In some embodiments, the locus where pests are to be controlled and / or prevented is a crop field.

[0201] The present invention also provides a method for controlling weeds, comprising applying an effective amount of any one of the SL compositions, mixtures or combinations disclosed herein to a locus where weeds are to be controlled, thereby controlling the weeds.

[0202] The present invention also provides a method for controlling weeds in a crop field, comprising applying an effective amount of any one of the SL compositions, mixtures or combinations disclosed herein to the crop field, thereby controlling the weeds in the crop field.

[0203] In some embodiments, the crop plant is selected from cotton, rice, bananas, potatoes, coffee, sugar cane, citrus, beans, sunflowers, apples, corn, soybeans, wheat, barley, oats, chickpeas, fruit trees, nut trees, and sorghum.

[0204] In some embodiments, the SL composition is diluted with water prior to administration.

[0205] In some embodiments, the locus where weeds are to be controlled is a crop field.

[0206] The weeds are selected from the group consisting of: Hibiscus trionum, Lolium perenne L.ssp.multiflorum (Lam.) Husnot, Sida rhombifolia L., Anodacristata (L.) Schlecht., Lamium spp.L., Cyperus difformis L., Croton sperrsifeorus, Nicandra physalodes, Chenopodium album L., Echinochloa colona, ​​Amaranthus viridis, Hordeummurinum subsp. Leporinum, Sisymbrium orientale, Ipomoea plebeia, Cerastium vulgatum, Bifora radians Bieb.), Echinochloa crus-galli (L.) Beauv., Digera spp., Digeraarvensis, Arctotheca calendula (L.) Levyns., Cynadon dactylone, Commelina benghalensis L., Eragrostis pilosa (L.) Beauv., Amaranthus retroflexus L., Amaranthus sp., Euphorbia hirta L., Datura wrightii Regel, Capsella bursa-pastoris (L.) Medik., Emex australis, Urtica dioica L., Veronicahederifolia L.), Erodium cicutarium, Juncus tenuis Willd., Juncus bufonius, Lythrum hyssopifolia, Rapistrum rugosum (L.) All.), Salvia reflexa, Buglossoidesarvensis syn Lithospermum arvens, Xanthium pungens, Ribes divaricatum, Ribes nigrum, Cyperus rotundus, Raphanus raphanistrum L., Echium plantagineum, Polygonum aviculare and Polygonum arenastrum, Parthenium, Lactuca serriola L., Acanthospermum, Galium tricornutum Dandy, Amsinckia calycina (Moris) Chater, Amsinckia intermediaFischer & C.Meyer, Amsinckia lycopsoides (Lehm.) Lehm., Triticum sp., Hordeum vulgare, Alopecurus myosuroides Huds., Lolium sp., Elymus repens, Bromus sterilis, Xanthium Spinosum, Datura ferox, Dinebra Arabica, Eleusine indica, Cynodon dactylon, Euphorbia Hirta, Trianthema Portulacasturm, Amaranthus deflexus, Amaranthus hybridus L., Polygonum, Persicaria maculosa), Synapis arvensis, Abutilon theophrasti Medik., Ambrosia artemisiifolia L.), Eastern Solanum ptychanthum, Solanum nigrum, Xanthium strumarium L., Polygonum convolvulus, Alopecurus sp., Bromusmadritensis sp., Panicum sp., Hordeum jubatum sp., Setaria sp., Panicum capillare L., Panicum miliaceum L., Digitaria sp., Cyperus esculentus L., Acanthospermum hispidumDC, Cynotis sp., Tradescantia fluminernsis, Galinsoga sp., Portulaca oleracea L.), Alternanthera caracasana, Tribulus zeyheri, Acanthospermum australe, Acanthospermum glabratum, Cleome monophylla, Phyllanthus sp., Flaveria bidentis, Galinsoga parviflora, Soliva sessilis, Bidens pilosa, Parnassia palustris, Eragrostis, Ipomeas sp., Hierochloe odorata, Anthoxanthum nitens, Rottboellia cochinchinensis L., Schkuhria Bonariensi L., Devil thorn, Zea mays L., Cleome viscosa), Parthenium hysterophorus, Commelina bengalensis, Dinebrasp., Portulaca sp.), Trianthima sp., Dactylocteniumaegyptium, Corchprus sp., Trianthema monogyna and Brachiaria sp.

[0207] In some embodiments, the weed is Chenopodium album. In some embodiments, the weed is Xanthium strumarium L. In some embodiments, the weed is Solanum nigrum.

[0208] The present invention provides a method, wherein the method is used in a crop field, wherein the crop is selected from the group consisting of: onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), beet (Beta vulgaris spec.altissima), beet (Beta vulgaris spec.rapa), European rapeseed (Brassica napus var.napus), turnip (Brassica napus var.napobrassica), turnip (Brassica rapa var.silvestris), large-leaf tea (Camellia sinensis), safflower (Carthamustinctorius), American pecan (Carya illinoinensis), lemon (Citrus limon), sweet orange (Citrussinensis), small-grain coffee (Coffea arabica) (medium-grain coffee (Coffea canephora), large-grain coffee (Coffealiberica)), cucumber (Cucumis sativus), bermudagrass (Cynodon dactylon), wild carrot (Daucuscarota), oil palm (Elaeis guineensis), wild strawberry (Fragaria vesca), soybean (Glycine max), upland cotton (Gossypium hirsutum), tree cotton (Gossypium arboreum), grass cotton (Gossypium herbaceum), kapok (Gossypium vitifolium), sunflower (Helianthus annuus), rubber tree (Heveabrasiliensis), barley (Hordeum vulgare), hops (Humulus lupulus), sweet potato (Ipomoeabatatas), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple (Malus spec.), cassava (Manihot esculenta), alfalfa (Medicago sativa), banana (Musa spec.), tobacco (Nicotiana tabacum) (N.rustica), olive (Olea europaea), rice (Oryza sativa), butter bean (Phaseolus lunatus), kidney bean (Phaseolus vulgaris), European spruce (Picea abies), pine (Pinus spec.), pea (Pisumsativum), apricot (Prunus armeniaca), European sweet cherry (Prunus avium), European sour cherry (Prunuscerasus), almond (Prunus dulcis), (Prunus domesticua), peach (Prunus persica), pear (Pyrus communis), blackcurrant (Ribes sylvestre), castor (Ricinus communis), sugar cane (Saccharum officinarum), rye (Secale cereale), taro (Solanum tuberosum), sorghum (Sorghum bicolor) (Sorghum vulgare), cocoa (Theobroma cacao), red clover (Trifoliumpratense), common wheat (Triticum aestivum), durum wheat (Triticum durum), broad bean (Viciafaba), grape (Vitis vinifera) and maize (Zea mays).

[0209] In some embodiments, the crop plant is selected from cotton, rice, bananas, potatoes, coffee, sugar cane, citrus, beans, sunflowers, apples, corn, soybeans, wheat, barley, oats, chickpeas, fruit trees, nut trees, and sorghum.

[0210] In some embodiments, the SL composition is applied to pasture. In some embodiments, the SL composition is applied to non-crop areas. In some embodiments, the SL composition is applied to fallow land.

[0211] In some embodiments, the SL composition is applied as a pre-harvest aid.

[0212] In some embodiments, the SL composition is incorporated pre-plant. In some embodiments, the SL composition is applied post-emergence. In some embodiments, the SL composition is applied pre-emergence.

[0213] In some embodiments, the mixture or combination is applied to pasture. In some embodiments, the mixture or combination is applied to non-crop areas. In some embodiments, the mixture or combination is applied to fallow land.

[0214] In some embodiments, the mixture or combination is applied as a preharvest adjuvant.

[0215] In some embodiments, the mixture or combination is applied in combination before planting. In some embodiments, the mixture or combination is applied after emergence. In some embodiments, the mixture or combination is applied before emergence.

[0216] In some embodiments, the SL composition is applied in an amount of about 0.001 L / ha to about 0.2 L / ha. In some embodiments, the SL composition is applied in an amount of about 0.001 L / ha to about 0.1 L / ha. In some embodiments, the SL composition is applied in an amount of about 0.001 L / ha to about 0.05 L / ha. In some embodiments, the SL composition is applied in an amount of about 0.006 L / ha. In some embodiments, the SL composition is applied in an amount of about 0.01 L / ha. In some embodiments, the SL composition is applied in an amount of about 0.02 L / ha. In some embodiments, the SL composition is applied in an amount of about 0.03 L / ha. In some embodiments, the SL composition is applied in an amount of about 0.04 L / ha. In some embodiments, the SL composition is applied in an amount of about 0.05 L / ha.

[0217] In some embodiments, the mixture or combination is applied in an amount of about 0.001L / ha to about 0.2L / ha. In some embodiments, the mixture or combination is applied in an amount of about 0.001L / ha to about 0.1L / ha. In some embodiments, the mixture or combination is applied in an amount of about 0.001L / ha to about 0.05L / ha. In some embodiments, the mixture or combination is applied in an amount of about 0.006L / ha. In some embodiments, the mixture or combination is applied in an amount of about 0.01L / ha. In some embodiments, the mixture or combination is applied in an amount of about 0.02L / ha. In some embodiments, the mixture or combination is applied in an amount of about 0.03L / ha. In some embodiments, the mixture or combination is applied in an amount of about 0.04L / ha. In some embodiments, the mixture or combination is applied in an amount of about 0.05L / ha.

[0218] In some embodiments, the SL composition is applied in an amount from about 0.01 g / ha of benzyl flumetsulam to about 15 g / ha of benzyl flumetsulam. In some embodiments, the SL composition is applied in an amount from about 0.5 g / ha of benzyl flumetsulam to about 10 g / ha of benzyl flumetsulam. In some embodiments, the SL composition is applied in an amount from about 0.5 g / ha of benzyl flumetsulam to about 10 g / ha of benzyl flumetsulam. In some embodiments, the SL composition is applied in an amount from about 0.5 g / ha of benzyl flumetsulam to about 5 g / ha of benzyl flumetsulam. In some embodiments, the SL composition is applied in an amount from about 5 g / ha of benzyl flumetsulam to about 10 g / ha of benzyl flumetsulam. In some embodiments, the SL composition is applied in an amount from about 0.5 g / ha of benzyl flumetsulam to about 2 g / ha of benzyl flumetsulam. In some embodiments, the SL composition is applied in an amount from about 3 g / ha of benzyl flumetsulam to about 5 g / ha of benzyl flumetsulam. In some embodiments, the SL composition is applied in an amount from about 7 g / ha of benzylsulfuron to about 9 g / ha of benzylsulfuron. In some embodiments, the SL composition is applied in an amount of about 1 g / ha of benzylsulfuron. In some embodiments, the SL composition is applied in an amount of about 2 g / ha of benzylsulfuron. In some embodiments, the SL composition is applied in an amount of about 4 g / ha of benzylsulfuron. In some embodiments, the SL composition is applied in an amount of about 8 g / ha of benzylsulfuron. In some embodiments, the SL composition is applied in an amount of 0.96 g / ha of benzylsulfuron, 1.060 g / ha of benzylsulfuron, 1.796 g / ha of benzylsulfuron, 4.19 g / ha of benzylsulfuron, or 8.38 g / ha of benzylsulfuron.

[0219] In some embodiments, the mixture or combination is applied in an amount from about 0.01 g / ha benzyl flumetsulam to about 15 g / ha benzyl flumetsulam. In some embodiments, the mixture or combination is applied in an amount from about 0.5 g / ha benzyl flumetsulam to about 10 g / ha benzyl flumetsulam. In some embodiments, the mixture or combination is applied in an amount from about 0.5 g / ha benzyl flumetsulam to about 10 g / ha benzyl flumetsulam. In some embodiments, the mixture or combination is applied in an amount from about 0.5 g / ha benzyl flumetsulam to about 5 g / ha benzyl flumetsulam. In some embodiments, the mixture or combination is applied in an amount from about 5 g / ha benzyl flumetsulam to about 10 g / ha benzyl flumetsulam. In some embodiments, the mixture or combination is applied in an amount from about 0.5 g / ha benzyl flumetsulam to about 2 g / ha benzyl flumetsulam. In some embodiments, the mixture or combination is applied in an amount from about 3g / ha benzsulfuron to about 5g / ha benzsulfuron. In some embodiments, the mixture or combination is applied in an amount from about 7g / ha benzsulfuron to about 9g / ha benzsulfuron. In some embodiments, the mixture or combination is applied in an amount of about 1g / ha benzsulfuron. In some embodiments, the mixture or combination is applied in an amount of about 2g / ha benzsulfuron. In some embodiments, the mixture or combination is applied in an amount of about 4g / ha benzsulfuron. In some embodiments, the mixture or combination is applied in an amount of about 8g / ha benzsulfuron. In some embodiments, the mixture or combination is applied in an amount of 0.96g / ha benzsulfuron, 1.060g / ha benzsulfuron, 1.796g / ha benzsulfuron, 4.19g / ha benzsulfuron or 8.38g / ha benzsulfuron.

[0220] In some embodiments, the methods comprise applying at least one additional pesticide.

[0221] In some embodiments, the additional pesticide is a herbicide. In some embodiments, the herbicide is selected from 2,4-D, imazethapyr, sulfonepyrazone, S-isopropylamine, glufosinate, fluclopyralid, glyphosate, triadimefon, sulfentrazone, methacetamiprid-P, mesotrione, metribuzin, and flumetrazol.

[0222] In some embodiments, saflufenacil and another pesticide are applied simultaneously. In some embodiments, saflufenacil and another pesticide are applied together. In some embodiments, another pesticide is applied with saflufenacil. In some embodiments, another pesticide is applied at the same time as saflufenacil. In some embodiments, saflufenacil and another pesticide are applied sequentially.

[0223] The present invention also provides use of any one of the SL compositions, combinations or mixtures disclosed herein for controlling and / or preventing pests, comprising applying any one of the SL compositions, combinations or mixtures disclosed herein to a locus where pests are to be controlled and / or prevented.

[0224] In some embodiments, the pest is a weed.

[0225] The present invention also provides use of any one of the SL compositions, combinations or mixtures disclosed herein for controlling weeds, comprising applying an effective amount of any one of the SL compositions, combinations or mixtures disclosed herein to a site where weeds are to be controlled.

[0226] The present invention also provides the SL composition, combination or mixture disclosed herein for use in controlling and / or preventing pests, comprising applying any one of the SL compositions, combinations or mixtures disclosed herein to a location where pests are to be controlled and / or prevented.

[0227] In some embodiments, the pest is a weed.

[0228] The present invention also provides the SL composition, combination or mixture disclosed herein for use in controlling weeds, comprising applying an effective amount of any one of the SL compositions, combinations or mixtures disclosed herein to a site where weeds are to be controlled.

[0229] The present invention also provides a package comprising any one of the SL compositions, combinations or mixtures disclosed herein.

[0230] The present invention provides use of an amine salt of saflufenacil for preparing a soluble liquid (SL) composition.

[0231] In some embodiments, the SL composition is any one of the SL compositions disclosed herein.

[0232] The invention provides an amine salt of saflufenacil, which is used for preparing a soluble liquid composition.

[0233] In some embodiments, the SL composition is any one of the SL compositions disclosed herein.

[0234] The formation of complexes based on electrostatic forces between active ingredients such as saflufenacil and organic bases such as amines is possible. The formation of the complex is possible, possibly due to the negative charge of the organic base and the positive charge of saflufenacil (which is a week acid chemical), as well as the stereochemical properties of saflufenacil.

[0235] The present invention also provides a method for preparing the SL composition disclosed herein, wherein the method comprises:

[0236] (i) obtaining a certain amount of saflufenacil and a certain amount of organic base.

[0237] (ii) mixing the saflufenacil obtained in step (i) with an organic base to obtain a SL composition.

[0238] In some embodiments, step (i) further comprises obtaining a certain amount of an agriculturally acceptable carrier, and step (ii) comprises mixing the saflufenacil, the organic base and the agriculturally acceptable carrier obtained in step (i) to obtain a SL composition.

[0239] In some embodiments, the mixing of step (ii) is performed until a homogeneous mixture is obtained.

[0240] In some embodiments, step (ii) comprises heating the mixture of saflufenacil and the organic base.

[0241] In another embodiment, the product of any of the disclosed methods can be isolated from the reaction mixture by any conventional technique known in the art. Such isolation techniques may include, but are not limited to, one or more of: concentration, extraction, precipitation, cooling, filtration, crystallization, and centrifugation followed by drying.

[0242] In another embodiment, the product of any of the disclosed methods may be optionally purified by any conventional technique known in the art. Such purification techniques may include, but are not limited to, one or more of precipitation, crystallization, slurrying, washing in a suitable solvent, filtering through a packed bed column, dissolving in an appropriate solvent, and reprecipitating by adding a second solvent in which the compound is insoluble, or any combination thereof.

[0243] Each embodiment disclosed herein is considered to be applicable to each other disclosed embodiment. Therefore, all combinations of various elements described herein are within the scope of the present invention. In addition, the elements described in the composition embodiment can be used in the combination, mixture, method, use, packaging and method embodiments described herein, and vice versa.

[0244] The present invention will be better understood by reference to the following examples, but those skilled in the art will readily appreciate that the specific experiments described in detail are merely illustrative of the present invention as more fully described in the claims that follow.

[0245] The invention is illustrated by the following examples without being restricted thereby.

[0246] Example

[0247] Example 1 - Safensulfuron SL preparation: Safensulfuron and C 150 is dissolved in PolarClean

[0248] Table 1.

[0249]

[0250] 1. C-150 and PolarClean solvent and saflufenacil were mixed together.

[0251] 2. Continue mixing until homogeneity is achieved.

[0252] Example 2-Safensulfuron SL preparation: Safensulfuron and diethanolamine are dissolved in PolarClean

[0253] Table 2.

[0254]

[0255] 1. Diethanolamine and PolarClean solvent and saflufenacil were mixed together.

[0256] 2. Continue mixing until homogeneity is achieved.

[0257] Example 3 - Saflufenacil and 2,4-D SL formulation containing 3% saflufenacil and 70% 2,4-D 2EH

[0258] Table 3.

[0259]

[0260] 1. C 050 and PolarClean solvent, 2,4-D (acid form), and saflufenacil were mixed together.

[0261] 2. Continue mixing until homogeneity is achieved.

[0262] 3. Add Emulsogen EL 360 (sold by Clariant) while mixing and EVM 70-2E (sold by Huntsman).

[0263] Example 4 - Efficacy of saflufenacil SL formulation (Scheme 1)

[0264] All seeds were sown in plastic pots (8 cm in diameter and 10.5 cm deep) filled with Newe Ya'ar soil (medium-heavy clay-loam). Each treatment was replicated 5 times. Spray applications were performed using an electric sprayer equipped with a flat fan 8001E nozzle 4 and operated at a spray volume of 20 L / dunam at a pressure of 300 kPa. The pots were transferred to a heated greenhouse (35-20°C) at the Newe Ya'ar Research Center in Israel and sprayed to field capacity 4 hours after the herbicide application. Weed development was visually assessed on a scale of 0-100% (0 = dead plants, 100 = healthy and vigorous plants) once a week and at the end of the trial to check the efficacy and selectivity of the applied herbicides.

[0265] The saflufenacil formulations were applied post-emergence. Table 4 below summarizes the application rates of the saflufenacil formulations. LQ is a water-based suspension concentrate (SC) formulation sold by BASF (active ingredient: saflufenacil at a concentration of 342 g / L). Saflufenacil 160SL (B) is the formulation of Example 1. Saflufenacil 160SL (A) is a formulation similar to that of Example 1, except that C150 C50 replacement.

[0266] Table 4.

[0267]

[0268] Example 4a - Efficacy on potted Chenopodium album (post-emergence).

[0269] The saflufenacil formulation was applied to potted Chenopodium album. The efficacy (control %) at 3, 7 and 18 days after spray application (DAA) is shown in Table 5 below.

[0270] Table 5

[0271]

[0272] The results are shown in Figure 1 middle.

[0273] Example 4b - Efficacy against potted Xanthium strumarium (post-emergence)

[0274] The saflufenacil formulation was applied on potted Xanthium strumarium L. The efficacy (% control) at 3, 7 and 18 days after spray application (DAA) is shown in Table 6 below.

[0275] Table 6.

[0276]

[0277] The results are shown in Figure 2 middle.

[0278] Example 4c - Efficacy on potted Solanum nigrum (post-emergence).

[0279] The saflufenacil formulation was applied to potted Solanum nigrum. The efficacy (control %) 3 days, 7 days and 18 days after the spray application is shown in Table 7 below.

[0280] Table 7.

[0281]

[0282] The results are shown in Figure 3 middle.

[0283] Conclusion - Examples 4a-c, Scheme 1

[0284] The results clearly show that the SL formulation of saflufenacil is effective against various types of weeds. In fact, the results show that the SL formulation of saflufenacil has eliminated the three weeds, Chenopodium album, Xanthium sibiricum and Solanum nigrum, in all pots using different concentrations as shown in Scheme 1.

[0285] Example 5 - Efficacy of saflufenacil SL formulation (Scheme 2)

[0286] All seeds were sown in plastic pots (8 cm in diameter and 10.5 cm deep) filled with Newe Ya'ar soil (medium-heavy clay-loam). Each treatment was repeated 5 times. Spray application was performed using an electric sprayer equipped with a flat fan 8001E nozzle 4 and operated at a spray volume of 20 L / dunam at a pressure of 300 kPa. The pots were transferred to a heated greenhouse (35-20°C) at the NeweYa'ar Research Center in Israel and sprayed to field capacity 4 hours after the herbicide application. Weed development was visually evaluated on a scale of 0-100% (0 = dead plants, 100 = healthy and vigorous plants) once a week and at the end of the trial to check the efficacy and selectivity of the applied herbicides.

[0287] The saflufenacil formulations were applied post-emergence. Table 8 below summarizes the application rates of the saflufenacil formulations. LQ is a water-based suspension concentrate (SC) formulation sold by BASF (active ingredient: saflufenacil at a concentration of 342 g / L). Saflufenacil 160SL(B) is the formulation of Example 1. Saflufenacil 160SL(B) Blank is the same formulation as Saflufenacil 160SL(B) but without saflufenacil.

[0288] Table 8.

[0289]

[0290]

[0291] Example 5a - Efficacy of saflufenacil SL formulation on potted Chenopodium album (post-emergence).

[0292] The application rates of saflufenacil formulations on potted Chenopodium album are shown in the following Table 9. The efficacy (% control) 3 days, 10 days and 18 days after spray application (DAA) is also shown in the following Table 9.

[0293] Table 9.

[0294]

[0295] The results are shown in Figure 4 middle

[0296] Example 5b - Efficacy of saflufenacil formulations on potted blackcurrant (Ribes nigrum) (post-emergence).

[0297] The spraying rates of saflufenacil formulations on potted Solanum nigrum are shown in the following Table 10. The efficacy (control %) 7 days, 11 days and 22 days after the spray application is also shown in the following Table 10.

[0298] Table 10.

[0299]

[0300]

[0301] The results are shown in Figure 5 middle.

[0302] Conclusion - Examples 5a-b, Scheme 2

[0303] The results clearly show that the SL formulation of saflufenacil is much more powerful and effective against weeds than the SC formulation of saflufenacil. The SL formulation killed all 3 weeds, namely Xanthium sibiricum, Blackcurrant and Chenopodium.

[0304] Example 6 - Biological Examples

[0305] A synergistic effect exists if the effect of the combination of active ingredients exceeds the sum of the effects of the individual components. The expected effect E for a given combination of active ingredients can be described by the so-called COLBY formula and can be calculated as follows (COLBY, SR "Calculating synergistic and antagonistic responses of herbicide combination". Weeds, Vol. 15, pp. 20-22; 1967):

[0306] ppm = milligrams of active ingredient per liter of spray mixture (= ai)

[0307] X = % of the effect caused by the active ingredient I at an application rate of active ingredient p ppm

[0308] Y = % of the effect caused by the active ingredient II at an application rate of q ppm of the active ingredient

[0309] E = expected effect of active ingredients I + II at an application rate of active ingredient p + q ppm (additive effect)

[0310] XY, then Colby's formula is: E = X + Y - 100

[0311] If the actual observed effect (O) exceeds the expected effect (E), the effect of the combination is superadditive, ie, synergism exists. OE = Synergy Index (FS).

Claims

1. A soluble liquid (SL) composition comprising (i) an amount of saflufenacil and (ii) an amount of an organic base; wherein the composition is free of water, and wherein the organic base is an amine selected from the group consisting of pyridine, diethanolamine, dimethylamine in tetrahydrofuran (THF), butylamine, dipropylamine, and ethoxylated fatty acid amines; wherein the amount of saflufenacil in the SL composition is from 1 wt % to 30 wt %, based on the total weight of the composition; The amount of the organic base in the composition is from 10 wt % to 80 wt %, based on the total weight of the composition.

2. The SL composition of claim 1, wherein the pKa of the amine is in the range of 4-11.

3. The SL composition of claim 1, wherein the amine is ethoxylated coconut fatty acid amine.

4. The SL composition of claim 1, wherein the SL composition is stable.

5. The SL composition of claim 1, wherein the SL composition has low persistent foam.

6. The SL composition of claim 1, wherein the amount of saflufenacil in the SL composition is from 10 wt% to 20 wt%, based on the total weight of the composition.

7. The SL composition of claim 1, wherein the amount of saflufenacil in the SL composition is from 1 wt% to 10 wt%, based on the total weight of the composition.

8. The SL composition of claim 1, wherein the amount of the organic base in the composition is from 50 wt% to 70 wt%, based on the total weight of the composition.

9. The SL composition of claim 1, wherein the amount of the organic base in the composition is from 10 wt% to 15 wt%, based on the total weight of the composition.

10. The SL composition of any one of claims 1 to 9, wherein the ratio of saflufenacil and the organic base in the composition is such that the ratio of the amine group to the saflufenacil molecule is at least 1:

1.

11. The SL composition of any one of claims 1-9, wherein the composition comprises an amount of at least one additive, wherein the amount of the additive in the SL composition is 1 wt% to 80 wt%, based on the total weight of the composition.

12. The SL composition of claim 11, wherein the additive is selected from the group consisting of adjuvants, surfactants, emulsifiers, antifreeze agents, defoamers, solvents, co-solvents and preservatives.

13. The SL composition of claim 11, wherein the amount of the additive in the SL composition is 1 wt% to 30 wt%, based on the total weight of the composition.

14. The SL composition of any one of claims 1-9, wherein the composition comprises an amount of at least one agriculturally acceptable carrier, wherein the amount of the agriculturally acceptable carrier in the composition is from 0.1 wt% to 90 wt%, based on the total weight of the composition.

15. The SL composition of claim 14, wherein the amount of the agriculturally acceptable carrier in the composition is 1 wt% to 40 wt%, based on the total weight of the composition.

16. The SL composition of any one of claims 1-9, wherein the composition comprises: (i) 10-20% by weight of saflufenacil, based on the total weight of the composition, (ii) 50 to 70 wt. % of an amine, based on the total weight of the composition, and (iii) 10-30 wt % of an agriculturally acceptable carrier, based on the total weight of the composition.

17. The SL composition of claim 16, wherein the agriculturally acceptable carrier is selected from aromatic hydrocarbons, alcohols, N,N-dimethylformamide, dimethylamide esters, dimethyl sulfoxide, N-alkyl pyrrolidone, paraffin, olive oil, castor oil, linseed oil, tung oil, sesame oil, corn oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil and coconut oil, fatty acid esters and ketones.

18. The SL composition of any one of claims 1-9, wherein the composition comprises an amount of at least one additional pesticide; wherein the amount of the additional pesticide in the composition is from 1 wt% to 80 wt%, based on the total weight of the composition.

19. The SL composition of claim 18, wherein the pesticide is a herbicide selected from the group consisting of 2,4-D, imazethapyr, sulfamethoxam, S-isopropylamine, glufosinate, fluclopyralid, glyphosate, triadimefon, sulfentrazone, methacetamiprid-P, mesotrione, metribuzin, and fluazifop-butyl.

20. The SL composition of claim 18, wherein the composition comprises: (i) 1-10% by weight of saflufenacil, based on the total weight of the composition, (ii) 60-80 wt. % of 2,4-D, based on the total weight of the composition, (iii) 10 to 15% by weight of an amine, based on the total weight of the composition, (iv) 1 to 10% by weight of an emulsifier, based on the total weight of the composition, (v) 1 to 10 wt % of a surfactant, based on the total weight of the composition, and (vi) 1 to 10 wt % of an agriculturally acceptable carrier, based on the total weight of the composition.

21. The SL composition of any one of claims 1-9, wherein the amount of saflufenacil is dissolved in the organic amine.

22. A combination comprising: (i) a certain amount of the SL composition according to any one of claims 1 to 21, and (ii) an amount of at least one additional pesticide; wherein the combination comprises at least 1% by weight of one or more of the compositions; the additional pesticide and the composition are mixed in a weight ratio of 1:100 to 100:

1.

23. The combination of claim 22, wherein the combination is more effective for controlling and / or preventing pests than when each pesticide is applied alone at the same amount, wherein the pests are weeds.

24. The combination of claim 22 or 23, wherein said amount of saflufenacil and said amount of additional pesticide, when applied together, are more effective for controlling and / or preventing pests than when the same amount of each pesticide is applied alone, wherein the pests are weeds.

25. The combination of claim 22 or 23, wherein the amount of saflufenacil in the combination is less than the pesticidally effective amount of saflufenacil when used alone, and / or the amount of the additional pesticide in the combination is less than the pesticidally effective amount of the additional pesticide when used alone.

26. A mixture comprising the SL composition of any one of claims 1-21 or the combination of any one of claims 22-25.

27. The mixture of claim 26, wherein the mixture further comprises at least one pesticide.

28. The mixture of claim 27, wherein the pesticide is a herbicide selected from the group consisting of 2,4-D, imazethapyr, sulfamethoxam, S-isopropylamine, glufosinate, fluclopyralid, glyphosate, triadimefon, sulfentrazone, methacetamiprid-P, mesotrione, metribuzin, and fluazifop-butyl.

29. The mixture of claim 27 or 28, wherein the pesticide is 2,4-D.

30. The mixture of any one of claims 26-28, wherein the mixture is a tank mix.

31. A SL composition comprising the combination of any one of claims 22-25 or the mixture of any one of claims 26-30.

32. A method for controlling and / or preventing pests, comprising applying an effective amount of the SL composition of any one of claims 1-21 and 31, the combination of any one of claims 22-25, or the mixture of any one of claims 26-30 to a locus where pests are to be controlled and / or prevented, thereby controlling and / or preventing pests, wherein the pests are weeds, wherein the SL composition, mixture or combination is applied in an amount of 0.001 L / ha to 0.2 L / ha.

33. A method for controlling weeds, comprising applying an effective amount of the SL composition of any one of claims 1 to 21 and 31, the combination of any one of claims 22 to 25, or the mixture of any one of claims 26 to 30 to a locus where weeds are to be controlled, thereby controlling weeds, wherein the SL composition, mixture or combination is applied in an amount of 0.001 L / ha to 0.2 L / ha.

34. The method of claim 32 or 33, wherein the locus is a crop field.

35. A method for controlling weeds in a crop field, comprising applying an effective amount of the SL composition of any one of claims 1 to 21 and 31, the combination of any one of claims 22 to 25, or the mixture of any one of claims 26 to 30 to the crop field, thereby controlling weeds in the crop field, wherein the SL composition, mixture or combination is applied in an amount of 0.001 L / ha to 0.2 L / ha.

36. The method of claim 34 or 35, wherein the crop is selected from the group consisting of cotton, rice, bananas, potatoes, coffee, sugar cane, citrus, beans, sunflowers, apples, corn, soybeans, wheat, barley, oats, chickpeas, fruit trees, nut trees, and sorghum.

37. The method of claim 32, 33 or 35, wherein the weed is Chenopodium album, Xanthium strumarium or Solanum nigrum.

38. The method of claim 32, 33 or 35, wherein the SL composition, combination or mixture is applied in combination before planting, applied before emergence or applied after emergence.

39. The method of claim 32, 33 or 35, wherein the SL composition, mixture or combination is applied to pasture, non-crop area and / or fallow land.

40. The method of claim 32, 33 or 35, wherein the SL composition, mixture or combination is applied as a preharvest adjuvant.

41. The method of claim 32, 33 or 35, wherein the SL composition, mixture or combination is applied in an amount of 0.001 L / ha to 0.05 L / ha.

42. The method of claim 32, 33 or 35, wherein the SL composition, mixture or combination is applied in an amount of 0.01 g / ha saflufenacil to 15 g / ha saflufenacil.

43. The method of claim 42, wherein the SL composition, mixture or combination is applied in an amount of 0.5 g / ha saflufenacil to 10 g / ha saflufenacil.

44. Use of the SL composition of any one of claims 1-21 and 31, the combination of any one of claims 22-25 or the mixture of any one of claims 26-30 for controlling and / or preventing pests, wherein the pests are weeds.

45. Use of the SL composition of any one of claims 1-21 and 31, the combination of any one of claims 22-25 or the mixture of any one of claims 26-30 for controlling weeds.

46. ​​The SL composition of any one of claims 1-21 and 31, the combination of any one of claims 22-25 or the mixture of any one of claims 26-30 for use in controlling and / or preventing pests, wherein the pests are weeds.

47. The SL composition of any one of claims 1-21 and 31, the combination of any one of claims 22-25 or the mixture of any one of claims 26-30 for use in controlling weeds.

48. Use of an amine salt of saflufenacil for preparing a soluble liquid (SL) composition; wherein the SL composition is the SL composition of any one of claims 1-21 and 31.

49. A package comprising the SL composition of any one of claims 1-21 and 31, the combination of any one of claims 22-25, or the mixture of any one of claims 26-30.

50. A method for preparing the SL composition of any one of claims 1-21 and 31, wherein the method comprises: (a) obtaining a certain amount of saflufenacil and a certain amount of organic base; (b) mixing the saflufenacil obtained in step (a) with an organic base to obtain a SL composition.

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