## STABLE LIQUID FORMULATIONS AND METHODS OF USING THE SAME 

[0001] Liquid pesticide compositions having enhanced stability, and methods of using the same are provided. 

[0002] Liquid compositions are desirable since they facili› tate easy volumetric measurement and transfer. This advan› tage can be realized for in-process liquid intermediates or final liquid compositions. Liquid compositions can be single-phase or multi-phase compositions, including emul› sions, suspensions, solutions, etc. Common ingredients in liquid compositions contain hydroxy-functionality in the diluents, solvents, surfactants, and/or rheology modifiers, etc. These common ingredients which contain hydroxy› functionality include water, alcohols, glycols, alkoxylated surfactants, etc. 

[0003] Certain pesticides are known to be chemically unstable. These pesticides exhibit unacceptable loss in stored liquid compositions. A chemically unstable pesticide generally has a greater than 5% (w/w) relative loss of that pesticide after storing the liquid composition for 8 weeks at 40° C. (measured using quantitative chromatography, such as HPLC). Chemically unstable liquid compositions are usually not commercially successful since liquid composi› tions are typically stored at 40° C. or higher. 

[0004] The most common composition types for chemi› cally unstable pesticides are solid compositions, such as a water-dispersible powder (WP), water-soluble powder (SP), water-dispersible granule (WG), water-soluble granule (SG), or broadcast-type ready-to-use granule (G). These compositions seek to avoid/minimize liquid-based contact of the pesticide with ingredients commonly used to make liquid compositions, and thereby maximize chemical stabil› ity of the pesticide by avoiding liquid compositions. The existence of commercially successful solid compositions for chemically unstable pesticides implies that liquid composi› tions do not have acceptable storage stability. 

[0005] U.S. Publication No. 2011/0166023 discloses an herbicidal composition comprising a) at least one ALS› inhibiting herbicide; b) at least one HPPD-inhibiting herbi› cide; and c) at least one saturated or unsaturated fatty acid. The publication asserts that the use of a saturated or unsatu› rated fatty acid may chemically stabilize an herbicidal composition comprising at least one sulfonylurea herbicide and at least one HPPD-inhibiting herbicide. However, while the use of certain fatty acids showed improved stability for several HPPD-inhibiting herbicides, almost every sulfony› lurea herbicide tested had an unacceptable storage stability (over 5% (w/w) relative loss after storage for 47 days at 40° C.). 

[0006] A need exists for a stable liquid pesticide (e.g. herbicidal) compositions particularly sulfonylurea herbi› cides exhibiting less than 5% (w/w) relative loss of the active herbicide upon storage at least 47 days at 40° C. 

## SUMMARY OF VARIOUS ASPECTS OF THE DISCLOSURE 

[0007] Liquid pesticide compositions and methods of making and using the same are provided. The liquid pesti› cide composition comprises a) halosulfuron-methyl; b) one 

## FIELD 

## BACKGROUND 

or more diluent(s), where the diluent(s) is a liquid compris› ing: i) a first carbon structure of at least six carbon atoms optionally including one or more heteroatom(s), the first carbon structure being linear, branched, cyclic or aromatic; ii) optionally one or more glyceryl, carbonyl, phenyl, sul› fonyl, or phosphonyl group(s) on the first carbon structure, wherein the organic diluent(s) lack hydroxyl group(s) on the first carbon structure unless they are part of the optional carbonyl, phenyl, sulfonyl, or phosphonyl group(s); c) optionally, one or more surfactant(s), wherein the one or more surfactant(s) comprise: i) a second carbon structure of at least six carbon atoms optionally including one or more heteroatom(s), wherein the second carbon structure is linear, branched, cyclic or aromatic; ii) optionally one or more glyceryl, carbonyl, phenyl, sulfonyl, orphosphonyl group(s) on the second carbon structure, wherein the surfactant(s) lack hydroxyl group(s) on the second carbon structure unless they are part of the optional phenyl, carbonyl, sulfonyl, or phosphonyl group(s); d) optionally, one or more rheology modifier(s); e) optionally, one or more buffering agent(s); wherein the liquid pesticide composition exhibits 5% (w/w) or less loss ofhalosulfuron-methyl upon storage for 8 weeks at 40° C. measured using quantitative chromatography. 

[0008] The liquid pesticide composition may include 0.01- 40% (w/w) of one or more pesticide(s), 40-95% (w/w) of one or more diluent(s), 0-20% (w/w) of one or more surfactant(s), and 0-10% (w/w) of one or more rheology modifier(s). In another embodiment, the liquid pesticide composition may include 5-30% (w/w) of one or more pesticide(s), 40-90% (w/w) ofone or more diluent(s), 5-10% (w/w) of one or more surfactant(s), and 0-5% (w/w) of one or more rheology modifier(s). In another embodiment, the liquid pesticide composition may include 20-30% (w/w) of one or more pesticide(s), 40-82% (w/w) of one or more diluent(s), 5-10% (w/w) of one or more surfactant(s), and 3-8% (w/w) of one or more rheology modifier(s). 

[0009] In addition to halosulfuron-methyl, the liquid pes› ticide composition may include one or more chemically stable pesticide(s), including Benzobicyclon, Dicamba, and/ or Prosulfuron. In one embodiment, the rheology modifier may comprise silica. 

[0010] In one embodiment, the surfactant is an acid selected from oleic, caprylic, decanedioic, or linolenic, or a salt thereof. The surfactant may also be a salt of the acid selected from sodium, potassium, lithium, magnesium, cal› cium, zinc, or aluminum salt, or a mixture of one or more of the foregoing salts and the acid. 

[0011] In one embodiment, the surfactant comprises at least one glyceryl group. The surfactant may be selected from tricaprylate glycerol, trioleate glycerol, tristearate glycerol, di-lineolate/monostearate glycerol, or mixtures thereof. The glyceryl may include a salt of carbonyl, sulfo› nyl, or phosphonyl, in which case any OH groups associated with the carbonyl, sulfonyl, or phosphonyl would not lead to degradation. However, an OH group associated with the glyceryl-moiety itself, such as in the case of a mono- or di-glyceride would lead to instability. 

[0012] In one embodiment, the surfactant may comprise a sulfonyl group. The surfactant may be selected from mono/ di oleyl sulfate, lauryl sulfate, dodecylbenzene sulfonate, oleyl sulfonate, 2-propenoic acid butyl ester polymer with ethenyl acetate and ethyenesulfonate, or a salt thereof. The surfactant may also be a salt of the sulfate or sulfonate selected from sodium, potassium, lithium, magnesium, cal- 

