Aug. 20, 2020  1  US 2020/0260722 Al  STABLE LIQUID FORMULATIONS AND  METHODS OF USING THE SAME  FIELD  BACKGROUND  SUMMARY OF VARIOUS ASPECTS OF THE  DISCLOSURE  [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.  [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  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-