EP4593598A1

EP4593598A1 - Storage-stable compositions including bixlozone and beflubutamid

Info

Publication number: EP4593598A1
Application number: EP23794521.7A
Authority: EP
Inventors: Krishnan Palanichamy
Original assignee: FMC Corp
Current assignee: FMC Corp
Priority date: 2022-09-30
Filing date: 2023-09-29
Publication date: 2025-08-06
Also published as: WO2024073019A1; KR20250077553A; TW202415291A

Abstract

Described herein are storage-stable compositions including bixlozone and beflubutamid. Also described herein are methods of preparing the compositions. Also described herein are methods for controlling undesirable vegetation with the compositions.

Description

TITLE

STORAGE-STABLE COMPOSITIONS INCLUDING BIXLOZONE AND BEFLUBUTAMID

FIELD OF THE DISCLOSURE

[0001] Described herein are storage-stable compositions comprising bixlozone and beflubutamid. Also described herein are methods of preparing the compositions. Also described herein are methods for controlling undesirable vegetation with the compositions.

BACKGROUND OF THE DISCLOSURE

[0002] Bixlozone and beflubutamid are not compatible active ingredients because the melting point of each active ingredient is reduced upon mixing them together. As a result, suspension concentrate formulations prepared either by milling both the active ingredients together or by mixing the individually milled suspension concentrates are not stable at both high temperatures and ambient storage temperatures. This incompatibility limits the feasibility of suspension concentrate formulations containing both bixlozone and beflubutamid. Furthermore, contacting these two active ingredients together promotes formation of a eutectic mixture such that the melting point of the mixture is reduced below the individual components. Consequently, there are no commercially available pre-mix formulations containing both bixlozone and beflubutamid.

BRIEF DESCRIPTION OF THE DISCLOSURE

[0003] It was discovered herein that interactions between bixlozone and beflubutamid can be avoided by encapsulating the beflubutamid. The encapsulation of beflubutamid results in a surprising enhancement in storage stability. Compositions including bixlozone and encapsulated beflubutamid, optionally in combination with a safener, are storage-stable and effective.

[0004] In one embodiment, the present disclosure is directed to a composition comprising: (i) encapsulated bixlozone; (ii) non-encapsulated bixlozone; (iii) encapsulated beflubutamid or an enantiomerically enriched form thereof; (iv) optionally an encapsulated or non-encapsulated active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof; and (v) optionally a non-encapsulated safener.

[0005] In another embodiment, the present disclosure is directed to a method of preparing a composition, the method comprising: I) encapsulating bixlozone; II) encapsulating beflubutamid or an enantiomerically enriched form thereof; III) optionally encapsulating an active ingredient incompatible with beflubutamid; and IV) forming a mixture comprising: (i) the encapsulated bixlozone; (ii) optionally non-encapsulated bixlozone; (iii) the encapsulated beflubutamid or an enantiomerically enriched form thereof; (iv) optionally the encapsulated active ingredient incompatible with beflubutamid and/or a non-encapsulated active ingredient incompatible with beflubutamid; and (v) optionally a non-encapsulated safener.

[0006] In yet another embodiment, the present disclosure is directed to a method for controlling undesirable vegetation, the method comprising applying to the undesirable vegetation or to a locus thereof or applying to soil or water to prevent an emergence or growth of the undesirable vegetation a composition comprising: (i) encapsulated bixlozone; (ii) nonencapsulated bixlozone; (iii) encapsulated beflubutamid or an enantiomerically enriched form thereof; (iv) optionally an encapsulated or non-encapsulated active ingredient incompatible with beflubutamid; and (v) optionally a non-encapsulated safener.

DETAILED DESCRIPTION OF THE DISCLOSURE

[0007] This written description uses examples to illustrate the present disclosure, including the best mode, and also to enable any person skilled in the art to practice the disclosure, including making and using any compositions or systems and performing any incorporated methods. The patentable scope of the disclosure is defined by the claims, and may include other examples that occur to those skilled in the art. Such other examples are intended to be within the scope of the claims if they have elements that do not differ from the literal language of the claims, or if they include equivalent elements with insubstantial differences from the literal language of the claims.

[0008] As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” “contains”, “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.

[0009] The transitional phrase “consisting of’ excludes any element, step, or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of’ appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

[0010] The transitional phrase “consisting essentially of’ is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially of’ occupies a middle ground between “comprising” and “consisting of’. The use of “consisting essentially of’ herein allows the applicant, as lexicographer, to define the invention being claimed by excluding any material, step, feature or method that is considered by the applicant to be non-critical to the claimed invention, but which may be known in the prior art and otherwise can be included in the invention being claimed, whether or not such inclusion or exclusion is specifically described in the specification. Exclusion of any material, step, feature or method by the applicant may be for the sole purpose of excluding elements of the prior art that affect the novelty and, therefore, the patentability of the invention being claimed. As such, the use of “consisting essentially of’ herein does not require explicit support from the specification to exclude any element of the prior art from the invention being claimed if inclusion of said element is detrimental to patentability of the invention claimed.

[0011] Where an invention or a portion thereof is defined with an open-ended term such as “comprising,” it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms “consisting essentially of’ or “consisting of.”

[0012] Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

[0013] Also, the indefinite articles “a” and “an” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. The term “optionally” in connection with an ingredient or method in the present formulation alternatively means “present or absent”. The “optional” component is “present” or “absent” independent of the presence or absence of other formulating ingredients or steps unless otherwise noted or recited.

[0014] As used herein, depending on the context in which it is used, the term “about” provides an estimate of a value associated with the claimed invention, where the estimated value is reasonable when taken in context with the description of the invention and in view of what is known from information available to the public, as such information would be understood or interpreted by a person of ordinary skill in the art. Generally, the term “about” as used herein means that the estimated value will fall within plus or minus 10% of the associated value. The term “about” may be further defined by context, and it is within the applicant’s rights as lexicographer to define how “about” should be interpreted within the specific context in which it is used in describing the invention.

[0015] As used herein, “wt%” refers to the weight percent of the recited component relative to the total weight of the recited composition.

[0016] As used herein, “enantiomerically enriched form thereof’ refers to a non-racemic compound in which either the S enantiomer or the R enantiomer predominates or is even present as the only stereoisomer, preferably the S enantiomer (e.g., beflubutamid-M). The enantiomerically enriched form may include up to 5% of the non-predominant stereoisomer.

[0017] As used herein, “substantially free” generally refers to no more than 2 wt%. In some embodiments, “substantially free” refers to no more than 1.5 wt%, no more than 1.0 wt%, no more than 0.5 wt%, or no more than 0.1 wt%.

[0018] Embodiments of this disclosure can be combined in any manner provided that the combinations result in obtaining the compositions and methods claimed herein.

[0019] Composition embodiments of the present disclosure include:

[0020] Embodiment Al. The composition described in the Summary of the Invention, wherein the encapsulated bixlozone and the non-encapsulated bixlozone are present in a ratio in the range of from about 1:9 to about 9: 1.

[0021] Embodiment A2. The composition described in Embodiment Al, wherein the encapsulated bixlozone and the non-encapsulated bixlozone are present in a ratio in the range of from about 1:8 to about 8:1.

[0022] Embodiment A3. The composition described in Embodiment A2, wherein the encapsulated bixlozone and the non-encapsulated bixlozone arc present in a ratio in the range of from about 1 :7 to about 7:1.

[0023] Embodiment A4. The composition described in Embodiment A3, wherein the encapsulated bixlozone and the non-encapsulated bixlozone are present in a ratio in the range of from about 1:6 to about 6:1.

[0024] Embodiment A5. The composition described in Embodiment A4, wherein the encapsulated bixlozone and the non-encapsulated bixlozone are present in a ratio in the range of from about 1:5 to about 5:1.

[0025] Embodiment A6. The composition described in Embodiment A5, wherein the encapsulated bixlozone and the non-encapsulated bixlozone arc present in a ratio in the range of from about 1:4 to about 4:1. [0026] Embodiment A7. The composition described in Embodiment A6, wherein the encapsulated bixlozone and the non-encapsulated bixlozone are present in a ratio in the range of from about 1:3 to about 3:1.

[0027] Embodiment A8. The composition described in Embodiment A7, wherein the encapsulated bixlozone and the non-encapsulated bixlozone are present in a ratio in the range of from about 1:2 to about 2:1.

[0028] Embodiment A9. The composition described in Embodiment A6, wherein the encapsulated bixlozone and the non-encapsulated bixlozone are present in a ratio in the range of from about 1 : 1 to about 1:1.

[0029] Embodiment B l. The composition described in the Summary of the Invention, wherein the encapsulated bixlozone is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, poly acrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi-synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof.

[0030] Embodiment B2. The composition described in Embodiment B l , wherein the encapsulated bixlozone is encapsulated with a synthetic polymer.

[0031] Embodiment B3. The composition described in Embodiment B2, wherein the encapsulated bixlozone is encapsulated with a polyurea.

[0032] Embodiment Cl. The composition described in the Summary of the Invention, wherein the encapsulated beflubutamid is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, poly acrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi-synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof. [0033] Embodiment C2. The composition described in Embodiment Cl, wherein the encapsulated beflubutamid is encapsulated with a synthetic polymer.

[0034] Embodiment C3. The composition described in Embodiment C2, wherein the encapsulated beflubutamid is encapsulated with a polyurea.

[0035] Embodiment DI. The composition described in the Summary of the Invention, wherein the composition is substantially free of non-encapsulated beflubutamid or an enantiomerically enriched form thereof.

[0036] Embodiment D2. The composition described in Embodiment DI, wherein the composition is free of non-encapsulated beflubutamid or an enantiomerically enriched form thereof.

[0037] Embodiment El. The composition described in the Summary of the Invention, wherein the additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is selected from acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amido sulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, bixlozone, beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, benquinotrione, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bipyrazone, bispyribac and its sodium salt, broclozone, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, cypyrafluone, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimesulfazet, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, dioxopyritrione, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, epyrifenacil, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, fluchloraminopyr, flufenacet, flufenoximacil, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, fhipyrsulfuron-methyl and its sodium salt, flurenol, flurenol- butyl, fluridonc, flurochloridonc, fluroxypyr, flurtamonc, flusulfinam, fluthiacct-mcthyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, L- glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin, icafolin, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin- ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, indolauxipyr, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil- sodium, ipfencarbazone, iptriazopyrid, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lancotrione, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metproxybicyclone, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop. propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriflubenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac- sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimisoxafen, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tcbuthiuron, tcfuryltrionc, tcmbotrionc, tcpraloxydim, terbacil, terbumeton, tcrbuthylazinc, terbutryn, tetflupyrolimet, thenylchlor, thiazopyr, (hicncarbazonc. thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr- triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron-methyl, tripyrasulfone, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4- hydroxy-l-methyl-l,5-naphthyridin-2(lf/)-one, 6-chloro-4-(2,7-dimethyl-l-naphthalenyl)-5- hydroxy-2-methyl-3(2H)-pyridazinone, 5-chloro-3-[(2-hydroxy-6-oxo-l-cyclohexen-l- yl)carbonyl]-l-(4-methoxyphenyl)-2(lH)-quinoxalinone, 2-chloro-A-(l -methyl- lH-tetrazol-5- yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2- difluoroethyl)-84rydroxypyrido[2,3-Z?]pyrazin-6(5H)-one), 4-(2,6-diethyl-4-methylphenyl)-5- hydroxy-2,6-dimethyl-3(2Z/)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5- dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (previously methioxolin), 4-(4-fluorophenyl)- 6- [(2-hydroxy-6-oxo- 1 -cyclohexen- 1 -yl)carbonyl] -2-methyl- 1 ,2,4-triazine-3 ,5(2//,4H)-dione, methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2- pyridinecarboxylate, 2-methyl-3-(methylsulfonyl)-A-(l-methyl-lH-tetrazol-5-yl)-4-

(trifluoromethyl)benzamide and 2-methyl-A-(4-methyl-l,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)- 4-(trifluoromethyl)benzamide, their environmentally compatible salts, “acids”, esters and amides, and combinations thereof. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Bull.) Butl. And Puccinia thlaspeos Schub, their environmentally compatible salts, “acids”, esters and amides, and combinations thereof.

[0038] Embodiment E2. The composition described in Embodiment El, wherein the additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is pethoxamid.

[0039] Embodiment E3. The composition described in Embodiment El, wherein the additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is clomazone.

[0040] Embodiment E4. The composition described in Embodiment El, wherein the additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is selected from atrazine, azimsulfuron, S-bcflubutamid. benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, clomazone, clopyralid potassium, cloransulam-methyl, 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, ethametsulfuron-methyl, flumetsulam, flupyrsulfuron-methyl, fluthiacet-methyl, fomesafen, imazethapyr, lenacil, mesotrione, metribuzin, metsulfuron-methyl, pethoxamid, picloram, pyroxasulfone, quinclorac, rimsulfuron, S-metolachlor, sulfentrazone, thifensulfuron-methyl, triflusulfuron-methyl, tribenuron-methyl, their environmentally compatible salts, “acids”, esters and amides, and combinations thereof.

[0041] Embodiment E5. The composition described in Embodiment El, wherein the additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is selected from flufenacet, flufenoximacil, prosulfocarb, pendimethalin, cinmethylin, tri-allate, pyroxasulfone, aclonifen, picolifen, diflufenican, S-metolachlor, dimethenamid-P, chlorotoluron, pyroxsulam, clodinafop, pinoxaden, florasulam, mesotrione, carfentrazone-ethyl, sulfentrazone, metribuzin, halauxifen, amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac- sodium, cloransulam-methyl, chlorimuron-ethyl, chlor sulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron- sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-A^f-[[(4-methoxy-6-methyl-l,3,5-triazin-2- yl)amino]carbonyl]benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4- (5,6-dihydro-5-methyl-l,4,2-dioxazin-3-yl)-A^-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]- 1 -methyl- l/f-pyrazole-5-sulfonamide), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2- chloro- -[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[l,2-h]pyridazine-3- sulfonamide), prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac- sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N- [2- [(4,6-dimethoxy- 1,3,5 -triazin-2-yl)carbony 1] -6- fluorophenyl]- 1 , 1 -di fl uoro-7V-methy 1 methanesul fonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-mcthyl, tritosulfuron, their environmentally compatible salts, “acids”, esters and amides, and combinations thereof.

[0042] Embodiment E6. The composition described in Embodiment El, wherein the additional active ingredient incompatible with beflubutamid herbicides selected from acetochlor, alachlor, anilophos, benfuresate, bensulide, butachlor, butamifos, butralin, butroxydim, butylate, carfentrazone-ethyl, chloipropham. clodinafop-propargyl, clomazone, cycloxydim, cyhalofop- butyl, diclofop-methyl, dimethametryn, dithiopyr, fenoxaprop-p-ethyl, fentrazamide, fluazifop-P- butyl, fluchloralin, fluchloraminopyr, flufenacet, flufenoximacil, flurochloridone, metazachlor, metolachlor, molinate, oxadiazon, oxyfluorfen, pebulate, pendimethalin, pretilachlor, propachlor, propanil, propaquizafop, prosulfocarb, quizalofop-ethyl, quizalofop-P-tefuryl, rimisoxafen, tebutam, tepraloxydim, thiobencarb, triallate, trifluralin, their environmentally compatible salts, “acids”, esters and amides, and combinations thereof.

[0043] Embodiment Fl. The composition described in the Summary of the Invention, wherein the encapsulated additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, poly acrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi-synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof.

[0044] Embodiment F2. The composition described in Embodiment Fl, wherein the encapsulated additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is encapsulated with a synthetic polymer.

[0045] Embodiment F3. The composition described in Embodiment F2, wherein the encapsulated additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is encapsulated with a polyurea.

[0046] Embodiment Gl. The composition described in the Summary of the Invention, wherein the encapsulated bixlozone is encapsulated separately from beflubutamid or an enantiomerically enriched form thereof.

[0047] Embodiment G2. The composition described in the Summary of the Invention, wherein the bixlozone and beflubutamid or an enantiomerically enriched form thereof, are coencapsulated.

[0048] Embodiment Hl . The composition described in the Summary of the Invention, wherein the safener is selected from benoxacor, cloquintocet, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N- (aminocarbonyl)-2-methylbenzenesulfonamide and A-(aminocarbonyl)-2- fluorobenzenesulfonamide, l-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2- methyl- 1,3 -dioxolane (MG 191), 4-(dichloroacetyl)-l-oxa-4-azospiro[4.5]decane (MON 4660), 2,2-dichloro-l-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone, 2-methoxy-N-[[4-

[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide, and combinations thereof.

[0049] Embodiment H2. The composition described in Embodiment Hl, wherein the safener is selected from benoxacor, cloquintocet, cloquintocet-mexyl, cyprosulfamide, dietholate, fenchlorazole-ethyl, fenclorim, isoxadifen-ethyl, mefenpyr-diethyl, naphthalic anhydride, and combinations thereof.

[0050] Embodiment H3. The composition described in Embodiment H2, wherein the safener is selected from cloquintocet, cloquintocet-mexyl, dietholate, fenchlorazole-ethyl, fenclorim, isoxadifen-ethyl, mefenpyr-diethyl, naphthalic anhydride, and combinations thereof.

[0051] Embodiment H4. The composition described in Embodiment H3, wherein the safener is selected from cloquintocet cloquintocet-mexyl, fenclorim, isoxadifen-ethyl, mefenpyr-diethyl, and combinations thereof.

[0052] Embodiment II. The composition described in the Summary of the Invention, wherein the composition further comprises an auxiliary selected from dispersants, surfactants, biocides, antifoamers, antifreeze agents, rheology modifiers, wetting agents, solvents, salts, and combinations thereof.

[0053] Embodiment 12. The composition described in Embodiment II, wherein the composition further comprises a dispersant.

[0054] Embodiment 13. The composition described in Embodiment II, wherein the composition further comprises a surfactant.

[0055] Embodiment 14. The composition described in Embodiment II, wherein the composition further comprises a biocide.

[0056] Embodiment 15. The composition described in Embodiment II, wherein the composition further comprises an antifoamer.

[0057] Embodiment 16. The composition described in Embodiment II, wherein the composition further comprises an antifreeze agent.

[0058] Embodiment 17. The composition described in Embodiment II, wherein the composition further comprises a rheology modifier. [0059] Embodiment 18. The composition described in Embodiment II, wherein the composition further comprises a wetting agent.

[0060] Embodiment 19. The composition described in Embodiment II, wherein the composition further comprises a solvent.

[0061] Embodiment 110. The composition described in Embodiment II, wherein the composition further comprises a salt.

[0062] Embodiment Il l. The composition described in Embodiment 110, wherein the composition further comprises a salt selected from sodium nitrate, calcium chloride, and combinations thereof.

[0063] Embodiment 112. The composition described in Embodiment II, wherein the composition further comprises two or more auxiliaries.

[0064] Embodiment 113. The composition described in Embodiment II, wherein the composition further comprises three or more auxiliaries.

[0065] Embodiment 114. The composition described in Embodiment II, wherein the composition further comprises four or more auxiliaries.

[0066] Embodiment JI. The composition described in the Summary of the Invention, wherein the composition is in a form selected from a premix, a tank mix, and a ready-to-use formulation.

[0067] Embodiment J2. The composition described in Embodiment JI, wherein the composition is a premix.

[0068] Embodiment J3. The composition described in Embodiment JI, wherein the composition is a tank mix.

[0069] Embodiment J4. The composition described in Embodiment JI, wherein the composition is a ready-to-use formulation. [0070] The composition embodiments of this disclosure may be combined with the methods of preparation embodiments of this disclosure in any manner. Similarly, the methods of preparation embodiments of this disclosure may be combined in any manner. The following embodiments are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever.

[0071] Methods of preparation embodiments of the present disclosure include:

[0072] Embodiment KI. The method of preparing a composition described in the Summary of the Invention, wherein the encapsulated bixlozone is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, poly acrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi-synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof.

[0073] Embodiment K2. The method of preparing a composition described in Embodiment KI, wherein the encapsulated bixlozone is encapsulated with a synthetic polymer.

[0074] Embodiment K3. The method of preparing a composition described in Embodiment K2, wherein the encapsulated bixlozone is encapsulated with a polyurea.

[0075] Embodiment LI. The method of preparing a composition described in the Summary of the Invention, wherein the encapsulated beflubutamid is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, polyacrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi-synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof.

[0076] Embodiment L2. The method of preparing a composition described in Embodiment LI, wherein the encapsulated beflubutamid is encapsulated with a synthetic polymer. [0077] Embodiment L3. The method of preparing a composition described in Embodiment L2, wherein the encapsulated beflubutamid is encapsulated with a polyurea.

[0078] Embodiment Ml. The method of preparing a composition described in the Summary of the Invention, wherein the encapsulated additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, poly acrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi-synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof.

[0079] Embodiment M2. The method of preparing a composition described in Embodiment Ml, wherein the encapsulated additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is encapsulated with a synthetic polymer.

[0080] Embodiment M3. The method of preparing a composition described in Embodiment M2, wherein the encapsulated additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is encapsulated with a polyurea.

[0081] Embodiment Nl. The method of preparing a composition described in the Summary of the Invention, wherein the encapsulated bixlozone is encapsulated separately from beflubutamid or an enantiomerically enriched form thereof.

[0082] Embodiment N2. The method of preparing a composition described in the Summary of the Invention, wherein the bixlozone and beflubutamid or an enantiomerically enriched form thereof, are co-encapsulated.

[0083] The composition embodiments of this disclosure may be combined with the methods for controlling undesirable vegetation embodiments of this disclosure in any manner. Similarly, the methods of preparation embodiments of this disclosure may be combined with the methods for controlling undesirable vegetation embodiments of this disclosure in any manner. Similarly, the methods for controlling undesirable vegetation embodiments of this disclosure may be combined in any manner. The following embodiments are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever.

[0084] Methods for controlling undesirable vegetation embodiments of the present disclosure include:

[0085] Embodiment 01. The method for controlling undesirable vegetation described in the Summary of the Invention, wherein the undesirable vegetation comprises at least one herbicide-resistant or herbicide-tolerant weed species.

[0086] Embodiment 02. The method for controlling undesirable vegetation described in the Summary of the Invention, wherein the undesirable vegetation comprises a broad leaf weed or a grass weed.

[0087] Embodiment 03. The method for controlling undesirable vegetation described in Embodiment 02, wherein the undesirable vegetation is selected from Abutilon theophrasti (ABUTH), Acalypha virginica (ACCVI), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Ambrosia artemisiifolia (AMBEL), Anagallis arvensis (ANGAR), Apera spica-venti (APESV), Arrhenatherum elatius (ARREB), Calystegia sepium (CAGSE), Capsella bursa-pastoris (CAPBP), Centaurea cyanus (CENCY), Chenopodium album (CHEAL), Chenopodium hybridum (CHEHY), Chenopodium polyspermum (CHEPO), Convolvulus arvensis (CONAR), Cynodon dactylon (CYNDA), Cyperus difformis (CYPDI), Cyperus iria (CYPIR), Datura stramonium (DATST), Daucus carota (DAUCA), Descurainia sophia (DESSO), Digitaria sanguinalis (DIGS A), Echinochloa crus-galli (ECHCG), Echinochloa colonum (ECHCO), Fumaria officinalis (FUMOF), Galium aparine (GALAP), Galinsoga quadriradiata (GASCI), Geranium dissectum (GERDI), Geranium mole (GERMO), Geranium pusilium (GERPU), Hibiscus trionum (HIBTR), Lamium amplexicaule (LAMAM), Lamium purpureum (LAMPU), Buglossoides arvensis (LIT AR), Lolium multiflorum (LOLMU), Lolium perenne (LOLPE), Lolium rigidum (LOLRI), Matricaria chamomilla (MATCH), Tripleurospermum inodorum (MATIN), Mercurialis annua (MERAN), Panicum dichotomiflorum (PANDI), Panicum miliaceum (PANMI), Papaver rhoeas (PAPRH), Phalaris minor (PHAMI), Poa annua (POAAN), Polygonum aviculare (POLAV), Fallopia convolvulus (POLCO), Persicaria hydropiper (POLHY), Persicaria lapathifolia (POLLA), Persicaria maculosa (POLPE), Portulaca oleracea (POROL), Potentilla tridentate (PTLTR), Senecio vulgaris (SENVU), Setaria pumila (SETPU), Setaria viridis (SETVI), Solatium nigrum (SOLNI), Sorghum halepense (SORHA), Stellaria media (STEME), Trifolium incarnatum (TRFIN), Veronica arvensis (VERAR), Veronica hederifolia (VERHE), Veronica persica (VERPE), Viola arvensis (VIOAR), and Xanthium strumarium (XANST), and combinations thereof.

[0088] Embodiment 04. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Abutilon theophrasti (ABUTH).

[0089] Embodiment 05. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Acalypha virginica (ACC VI).

[0090] Embodiment 06. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Alopecurus myosuroides (ALOMY).

[0091] Embodiment 07. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Amaranthus retroflexus (AMARE).

[0092] Embodiment 08. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Ambrosia artemisiifolia (AMBEL).

[0093] Embodiment 09. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Anagallis arvensis (ANGAR).

[0094] Embodiment 010. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Apera spica-venti (APESV).

[0095] Embodiment Oi l. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Arrhenatherum elatius (ARREB).

[0096] Embodiment 012. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Calystegia sepium (CAGSE). [0097] Embodiment 013. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Capsella bursa-pastoris (CAPBP).

[0098] Embodiment 014. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Centaurea cyanus (CENCY).

[0099] Embodiment 015. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Chenopodium album (CHEAL).

[0100] Embodiment 016. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Chenopodium hybridum (CHEHY).

[0101] Embodiment 017. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Chenopodium polyspermum (CHEPO).

[0102] Embodiment 018. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Convolvulus arvensis (CONAR).

[0103] Embodiment 019. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Cynodon dactylon (CYNDA).

[0104] Embodiment 020. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Datura stramonium (DATST).

[0105] Embodiment 021. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Daucus carota (DAUCA).

[0106] Embodiment 022. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Descurainia sophia (DESSO).

[0107] Embodiment 023. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Digitaria sanguinalis (DIGSA).

[0108] Embodiment 024. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Echinochloa crus-galli (ECHCG). [0109] Embodiment 025. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Fumaria officinalis (FUMOF).

[0110] Embodiment 026. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Galium aparine (GALAP).

[0111] Embodiment 027. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Galinsoga quadriradiata (GASCI).

[0112] Embodiment 028. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Geranium dissectum (GERD I).

[0113] Embodiment 029. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Geranium mole (GERMO).

[0114] Embodiment 030. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Geranium pusilium (GERPU).

[0115] Embodiment 031. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Hibiscus trionum (HIBTR).

[0116] Embodiment 032. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Lamium amplexicaule (LAMAM).

[0117] Embodiment 033. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Lamium purpureum (LAMPU).

[0118] Embodiment 034. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Buglossoides arvensis (LIT AR).

[0119] Embodiment 035. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Lolium multiflorum (LOLMU).

[0120] Embodiment 036. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Lolium perenne (LOLPE). [0121] Embodiment 037. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Matricaria chamomilla (MATCH).

[0122] Embodiment 038. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Tripleurospermum inodorum (MATIN).

[0123] Embodiment 039. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Mercurialis annua (MERAN).

[0124] Embodiment 040. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Panicum dichotomiflorum (PANDI).

[0125] Embodiment 041. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Panicum miliaceum (PANMI).

[0126] Embodiment 042. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Papaver rhoeas (PAPRH).

[0127] Embodiment 043. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Poa annua (POAAN).

[0128] Embodiment 044. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Polygonum aviculare (POLAV).

[0129] Embodiment 045. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Fallopia convolvulus (POLCO).

[0130] Embodiment 046. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Persicaria hydropiper (POLHY).

[0131] Embodiment 047. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Persicaria lapathifolia (POLLA).

[0132] Embodiment 048. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Persicaria maculosa (POLPE). [0133] Embodiment 049. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Portulaca oleracea (POROL).

[0134] Embodiment 050. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Potentilla tridentate (PTLTR).

[0135] Embodiment 051. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Senecio vulgaris (SENVU).

[0136] Embodiment 052. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Setaria pumila (SETPU).

[0137] Embodiment 053. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Setaria viridis (SET VI).

[0138] Embodiment 054. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Solanum nigrum (SOLNI).

[0139] Embodiment 055. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Sorghum halepense (SORHA).

[0140] Embodiment 056. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Stellaria media (STEME).

[0141] Embodiment 057. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Trifolium incarnatum (TRFIN).

[0142] Embodiment 058. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Veronica arvensis (VERAR).

[0143] Embodiment 059. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Veronica hederifolia (VERHE).

[0144] Embodiment 060. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Veronica persica (VERPE). 2. [0145] Embodiment 061. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Viola arvensis (VIOAR).

[0146] Embodiment 062. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is Xanthium strumarium (XANST).

[0147] Embodiment 063. The method for controlling undesirable vegetation described in Embodiment 03, wherein the undesirable vegetation is selected from annual blue grass, annual ryegrass (Lolium rigidum), ball medic (Medicago spp.), barley grass (Hordeum murinum), bedstraw (Galium tricomutum), Benghal dayflower, bifora (Bifora lesiiculala). black grass, black night shade, broadleaf signal grass, brome grass (Bromus spp.), Canada thistle, capeweed (Arctotheca calendula), cheat, chickweed (Stellaria media), common cocklebur (Xanthium pensylvanicum), common ragweed, com poppies, doublegee (Emex australis), field violet, fleabane (Conyza bonariensis) giant foxtail, fumitory (Fumaria spp), goose grass, green fox tail, guinea grass, hairy beggarticks, herbicide-resistant black grass, horseweed, Indian hedge mustard (Sisymbrium orientale), Italian rye grass, Jersey cudweed (Gnaphalium luteoalbum), jimsonweed, johnsongrass (Sorghum halepense), large crabgrass, lesser loosestrife (Lythrum hyssopifolia), little seed cany grass, morning glory, Patterson’s Curse (Echium plantagineum), Pennsylvania smartweed, phalaris (Phalaris paradoxa), pitted morningglory, prickly lettuce (Lactuca serriola), prickly sida, quack grass, redflowered mallow (Modiola caroliniana), redroot pigweed, rough poppy (Papaver hybridum), serradella, shatter cane, shepherd’s purse, silky windgrass, silvergrass (Vulpia bromoides), sowthistle (Sonchus oleraceus), sub-clover (Trifolium spp.), sunflower (as weed in potato), volunteer chickpea, faba beans, field peas, lentils, lupins and vetch, wild buckwheat (Polygonum convolvulus), wild mustard (Brassica kaber), wild oat (Avena fatua), wild pointsettia, wild radish (Raphanus raphanistrum), wild turnip (Rapistrum rugosum, Brassica tournefortii), wireweed (Polygonum aviculare), yellow foxtail, and yellow nutsedge (Cyperus esculentus).

[0148] Embodiment 063. The method of Embodiment 062 wherein the undesirable vegetation is selected from wild radish (Raphanus raphanistrum), velvetleaf, jimsonweed, common cocklebur, and hairy beggarticks. [0149] Embodiment 064. The method of Embodiment 063 wherein the undesirable vegetation is wild radish (Raphanus raphanistruni).

[0150] Embodiment Pl. The method for controlling undesirable vegetation described in the Summary of the Invention, wherein the composition is applied at a stage selected from pre-emergence, post-emergence, and combinations thereof.

[0151] Embodiment P2. The method for controlling undesirable vegetation described in Embodiment Pl, wherein the composition is applied at pre-emergence.

[0152] Embodiment P3. The method for controlling undesirable vegetation described in Embodiment Pl, wherein the composition is applied at post-emergence.

[0153] Embodiment P4. The method for controlling undesirable vegetation described in Embodiment Pl, wherein the composition is applied at pre-emergence and post-emergence.

[0154] Generally, compositions in accordance with the present disclosure comprise bixlozone and beflubutamid or an enantiomerically enriched form thereof in an effective amount. In some embodiments, compositions in accordance with the present disclosure comprise bixlozone and beflubutamid or an enantiomerically enriched form thereof in a synergistically effective amount. An effective amount of bixlozone and beflubutamid or an enantiomerically enriched form thereof is any amount that has the ability to combat the harmful plants. The effectiveness of said compositions used in methods for the control of harmful plants will depend on various factors such as the mode of application, the harmful plants to be combated, the useful plant to be protected, the application time, etc. Methods of using of said effective compositions can be readily determined by the skilled person using well known principles.

[0155] In many embodiments, bixlozone and beflubutamid are present and/or applied in a ratio of bixlozone to beflubutamid that is an effective amount. In some embodiments, bixlozone and beflubutamid are present and/or applied in a ratio of bixlozone to beflubutamid that is selected to provide a synergistic herbicidal action. An effective amount of bixlozone and beflubutamid or an enantiomerically enriched form thereof is any amount that has the ability to combat the harmful plants. The ratio may be a weight ratio, a molar ratio, an application rate ratio, or a volume ratio. The ratio is preferably an application rate ratio. Grams per hectare is indicated by “g/ha”.

[0156] In some embodiments, bixlozone is employed in an amount of from about 1 g/ha, about 10 g/ha, about 50 g/ha, about 100 g/ha, about 200 g/ha, about 300 g/ha, about 400 g/ha, about 500 g/ha, about 600 g/ha, about 700 g/ha, about 800 g/ha, about 900 g/ha, about 1000 g/ha, about 1100 g/ha, about 1200 g/ha, about 1300 g/ha, about 1400 g/ha, about 1500 g/ha, about 1600 g/ha, about 1700 g/ha, about 1800 g/ha, about 1900 g/ha, about 2000 g/ha, about 2100 g/ha, about 2200 g/ha, about 2300 g/ha, about 2400 g/ha, about 2500 g/ha, about 2600 g/ha, about 2700 g/ha, about 2800 g/ha, about 2900 g/ha, about 3000 g/ha, or greater than about 3000 g/ha, to about 10 g/ha, about 50 g/ha, about 100 g/ha, about 200 g/ha, about 300 g/ha, about 400 g/ha, about 500 g/ha, about 600 g/ha, about 700 g/ha, about 800 g/ha, about 900 g/ha, about 1000 g/ha, about 1100 g/ha, about 1200 g/ha, about 1300 g/ha, about 1400 g/ha, about 1500 g/ha, about 1600 g/ha, about 1700 g/ha, about 1800 g/ha, about 1900 g/ha, about 2000 g/ha, about 2100 g/ha, about 2200 g/ha, about 2300 g/ha, about 2400 g/ha, about 2500 g/ha, about 2600 g/ha, about 2700 g/ha, about 2800 g/ha, about 2900 g/ha, about 3000 g/ha, or greater than about 3000 g/ha. However, higher and lower doses may also provide adequate control.

[0157] In some embodiments, beflubutamid or an enantiomerically enriched form thereof is employed in an amount of from about 1 g/ha, about 10 g/ha, about 50 g/ha, about 100 g/ha, about 200 g/ha, about 300 g/ha, about 400 g/ha, about 500 g/ha, about 600 g/ha, about 700 g/ha, about 800 g/ha, about 900 g/ha, about 1000 g/ha, about 1100 g/ha, about 1200 g/ha, about 1300 g/ha, about 1400 g/ha, about 1500 g/ha, about 1600 g/ha, about 1700 g/ha, about 1800 g/ha, about 1900 g/ha, about 2000 g/ha, about 2100 g/ha, about 2200 g/ha, about 2300 g/ha, about 2400 g/ha, about 2500 g/ha, about 2600 g/ha, about 2700 g/ha, about 2800 g/ha, about 2900 g/ha, about 3000 g/ha, or greater than about 3000 g/ha, to about 10 g/ha, about 50 g/ha, about 100 g/ha, about 200 g/ha, about 300 g/ha, about 400 g/ha, about 500 g/ha, about 600 g/ha, about 700 g/ha, about 800 g/ha, about 900 g/ha, about 1000 g/ha, about 1100 g/ha, about 1200 g/ha, about 1300 g/ha, about 1400 g/ha, about 1500 g/ha, about 1600 g/ha, about 1700 g/ha, about 1800 g/ha, about 1900 g/ha, about 2000 g/ha, about 2100 g/ha, about 2200 g/ha, about 2300 g/ha, about 2400 g/ha, about 2500 g/ha, about 2600 g/ha, about 2700 g/ha, about 2800 g/ha, about 2900 g/ha, about 3000 g/ha, or greater than about 3000 g/ha. However, higher and lower doses may also provide adequate control.

[0158] In some embodiments, bixlozone and beflubutamid or an enantiomerically enriched form thereof are employed in a ratio of 1.6:1 (200 g/ha bixlozone: 125 g/ha beflubutamid), 1:1.25 (200 g/ha bixlozone:250 g/ha beflubutamid), 3.2:1 - 1.6:1 (200 g/ha bixlozone:62.5 g/ha enantiomerically enriched beflubutamid - 200 g/ha bixlozone: 125 g/ha enantiomerically enriched beflubutamid), or 2:1 (200 g/ha bixlozone: 125 g/ha enantiomerically enriched beflubutamid)

[0159] Rates of application of the compositions will vary according to prevailing conditions such as targeted weeds, degree of infestation, weather conditions, soil conditions, crop species, mode of application, and application time. Compositions containing the active compounds may be applied in the form in which they are formulated. For example, they may be applied as sprays, such as water-dispersible concentrates, wettable powders, or water-dispersible granules. In practice of the present disclosure, rates of application of bixlozone and beflubutamid or an enantiomerically enriched form thereof can be varied independent of each other, provided that each of the components are applied within the disclosed limits of the present disclosure.

[0160] Agrochemical compositions according to the present disclosure may be in any suitable form of agrochemical compositions known in the art. The agrochemical compositions may include bixlozone and beflubutamid or an enantiomerically enriched form thereof in the same form or different forms. Example formulations of agrochemical compositions in accordance with the present disclosure are suspension concentrates (SC), capsule suspension concentrates (CS), mixtures of SC and CS formulations (ZC), emulsifiable concentrates (EC), and water-in-oil emulsions (EW). Particularly preferred formulations of agrochemical compositions in accordance with the present disclosure are mixtures of suspension concentrates (SC) and capsule suspension concentrates (CS) formulations (ZC). The acronym “SC” means suspension concentrate (a stable suspension of active ingredient(s) with water as the fluid); “ZC” refers to a mixed formulation of CS and SC (a stable suspension of capsules and active ingredient(s) in a fluid, normally intended for dilution with water before use). [0161] The agrochemical compositions may be applied in various combinations of the two active compounds. For example, they may be applied as a single “pre-mix” form, or in a combined spray mixture composed from separate formulations of the active compounds, e.g., a “tank-mix” form. Likewise, any form of combination of the active components may be applied for either pre- or post-emergence control of harmful plants, e.g., weeds in crops of useful plants.

[0162] Compositions in accordance with the present disclosure may be formulated with further suitable formulation components known in the art. As non-limiting examples, compositions in accordance with the present disclosure may be formulated using known auxiliaries, adjuvants, diluents, solvents, dispersants, surfactants, protective colloids, thickeners, penetrating agents, stabilizers, sequestering agents, anti-caking agents, coloring agents, pigments, corrosion inhibitors, biocides, antifoamers, antifreeze agents, rheology modifiers, and combinations thereof.

[0163] The term surfactant, as used herein, means an agriculturally acceptable material which imparts emulsifiability, stability, spreading, wetting, dispersibility or other surfacemodifying properties. Examples of suitable surfactants include lignin sulfonates, fatty acid sulfonates (e.g., lauryl sulfonate), the condensation product of formaldehyde with naphthalene sulfonate, alkylarylsulfonates, ethoxylated alkylphenols, and ethoxylated fatty alcohols. Other known surfactants that have been used with herbicides are also acceptable.

[0164] Suitable diluents may be added during the formulation process, after the formulation process (e.g., by the user - a farmer or custom applicator), or both. The term diluent includes all liquid and solid agriculturally acceptable material-including carriers which may be added to the herbicides to bring them in a suitable application or commercial form and include solvents, emulsifiers, and dispersants. Examples of suitable solid diluents or carriers are aluminum silicate, talc, lactose, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, absorbent carbon black, chalk, silica, and clays such as kaolin and bentonite. Examples of suitable liquid diluents include water, organic solvents (e.g., acetophenone, cyclohexanone, isophorone, toluene, xylene, petroleum distillates), amines (e.g., ethanolamine, dimethylformamide), and mineral, animal, and vegetable oils (used alone or in combination). [0165] Compositions in accordance with the present disclosure may also be formulated with further suitable additional active ingredients incompatible with beflubutamid or an enantiomerically enriched form thereof known in the art. An additional herbicide may be utilized if broadening of the spectrum of control or preventing the build-up of resistance is desired. Examples of additional active ingredients incompatible with beflubutamid or an enantiomerically enriched form thereof are acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amido sulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, bixlozone, beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, benquinotrione, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bipyrazone, bispyribac and its sodium salt, broclozone, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafcnacil, butamifos, butralin, butroxydim, butylate, cafcnstrolc, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, cypyrafluone, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimesulfazet, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, dioxopyritrione, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, epyrifenacil, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, fluchloraminopyr, flufenacet, flufenoximacil, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol- butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, flusulfinam, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, L- glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin, icafolin, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin- ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, indolauxipyr, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil- sodium, ipfencarbazone, iptriazopyrid, isoproturon, isouron, isoxaben, isoxaflutolc, isoxachlortolc, lactofcn, lancotrionc, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metproxybicyclone, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriflubenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac- sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimisoxafen, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr- triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron-methyl, tripyrasulfone, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4- hydroxy-l-methyl-l,5-naphthyridin-2(l/7)-one, 5-chloro-3-[(2-hydroxy-6-oxo-l-cyclohexen-l- yl)carbonyl]-l-(4-methoxyphenyl)-2(l/f)-quinoxalinone, 2-chloro-A-(l -methyl- l/f-tetrazol-5- yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2- difluorocthyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5//)-onc), 4-(2,6-dicthyl-4-mcthylphcnyl)-5- hydroxy-2,6-dimethyl-3(2//)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5- dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (previously methioxolin), 4-(4-fluorophenyl)- 6- [(2-hydroxy-6-oxo- 1 -cyclohexen- 1 -yl)carbonyl] -2-methyl- 1 ,2,4-triazine-3 ,5 (2 HA Hj-dionc. methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2- pyridinecarboxylate, 2-methyl-3-(methylsulfonyl)-A-(l-methyl-lH-tetrazol-5-yl)-4-

(trifluoromethyl)benzamide and 2-methyl- A-(4-methyl- 1 ,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)- 4-(trifluoromethyl)benzamide. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albeitini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. And Puccinia thlaspeos Schub, their environmentally compatible salts, “acids”, esters and amides, and combinations thereof.

[0166] Any of the water-soluble salts are appropriate in this formulation. Examples of appropriate salts are common inorganic salts. Appropriate salts are those that are easily water-soluble and that are selected from the group consisting of alkali metal halide, alkaline earth metal halide, ammonium halide, alkali metal sulfate, alkaline earth metal sulfate, ammonium sulfate, alkali metal nitrate, alkaline earth metal nitrate, ammonium nitrate, alkali metal carbonate, and ammonium carbonate. Examples of alkali metal halides include LiCl, LiBr, Lil, NaCl, NaBr, Nal, KF, KC1, KBr, KI, RbF, RbCl, RbBr, and Rbl. Examples of alkaline earth metal halides include MgCl₂, MgBr₂, Mgl₂, CaCl₂, CaBr₂, Cal₂, SrCl₂, SrBr₂, Srl₂, BaCl₂, BaBr₂, and Bal₂. Examples of ammonium halide include NH₄F, NH₄C1, NH₄Br, and NH₄I. Examples of alkali metal sulfate are Li₂SO₄, Na₂SO₄, K₂SO₄, and Rb₂SO₄. An example of an alkaline earth metal sulfate is MgSO₄. Ammonium sulfate is (NH₄)₂SO₄. Examples of alkali metal nitrate include LiNC^NaNC^, KNO3, and RbNOg. Examples of alkaline earth metal nitrate include Mg(NO3)₂, Ca(NC>3)₂, and Sr(NO3)₂. Ammonium nitrate is NH₄NO3- Examples of alkali metal carbonate include Na₂CO3, K₂CO3, and Rb₂CO3- Ammonium carbonate is (NH4)₂CO₃.

[0167] Compositions in accordance with the present disclosure may also be formulated with further suitable safcncrs known in the art. A safcncr compound is a compound, which is effective for antagonism of bixlozone or the optional additional herbicide(s), and which is applied in a suitable amount i.e., an amount which counteracts to some degree a phytotoxic response of a useful plant to the herbicide(s). The safener may suitably be incorporated in the composition. Safeners suitable for use include benoxacor, cloquintocet, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N- (aminocarbonyl)-2-methylbenzenesulfonamide and A^/-(aminocarbonyl)-2- fluorobenzenesulfonamide, l-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2- methy 1-1, 3 -dioxolane (MG 191), 4-(dichloroacetyl)-l-oxa-4-azospiro[4.5]decane (MON 4660), 2,2-dichloro-l-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone, 2-methoxy-N-[[4-

[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide, or their environmentally compatible salts, “acids”, esters and amides, and combinations thereof

[0168] The compositions according to the present disclosure can be employed for the selective control of grasses and annual and perennial monocotyledonous and dicotyledonous harmful plants the presence of useful plants such as maize, soya, peas, beans, sunflowers, oilseed rape, sugar cane, cassava, pumpkins, potatoes, vegetables and tobacco. Within the scope of this invention is also the control of such harmful plants found among transgenic useful plants or among useful plants selected by classical means which are resistant to bixlozone. Likewise, the compositions can be employed for controlling undesirable harmful plants in plantation crops.

[0169] Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever.

EXAMPLES

[0170] The invention is illustrated by the following examples.

[0171] Materials.

[0172] The following materials are utilized in these examples:

[0173] Reax 88B: sodium ligno sulfonate dispersant

[0174] Aromatic 200ND: high solvency naphthalene-depleted Cl l aromatic fluid

[0175] Kelzan S+: xantham gum

[0176] Proxel GXL: antibacterial aqueous solution of l,2-benzisothiazol-3(2H)-one

[0177] HMDA: hexamethylene diamine

[0178] PAPI 27: polymethylene polyphenylisocyanate that contains methylene diphenyl diisocyanate

[0179] Supragil MNS: condensed methyl naphthalene sulfonate, sodium salt

[0180] Xiameter AFE-0100: 30% active silicone emulsion

[0181] Example 1. Component compositions.

[0182] Separate component compositions were prepared as follows. [0183] Composition A.

[0184] Table 1. Bixlozone SC composition.

[0185] Composition B .

[0186] Table 2. Cloquintocet-mexyl SC composition.

[0187] Composition C.

[0188] Table 3. Bixlozone CS composition.

[0189] Composition D.

[0190] Table 4. Beflubutamid SC composition.

[0191] Composition E.

[0192] Table 5. Beflubutamid CS composition. [0193] Example 2. Preparation of component compositions.

[0194] The above compositions were prepared as follows.

[0195] Encapsulation of beflubutamid.

[0196] About 30 parts of beflubutamid was mixed with 12 parts of Aromatic 200 ND and heated to around 60 to 65 °C to completely dissolve the beflubutamid in Aromatic 200 ND, then 2 parts of PAPI 27 was added. In a separate vessel, 46 parts of water was mixed with 1.15 part of Reax 88B and heated to 65 °C. The two solutions were added together and mixed to form a stable emulsion. Then, 2 parts of 43% solution of HMDA was added to the emulsified mass to yield the encapsulated beflubutamid. The solution was then cured at 55 °C for 4 hours. After completing the reaction, 2 parts of 2.0% Kelzan S solution was added to increase the viscosity.

[0197] Encapsulation of bixlozone.

[0198] Encapsulation of bixlozone was carried out following a similar procedure as described for beflubutamid.

[0199] Preparation of active ingredients for SC formulations.

[0200] The SC formulations were prepared by wet milling the active ingredient in a media mill until a particle size D90 of less than 10 micron was achieved.

[0201] Example 3. Premix compositions.

[0202] Premix composition A.

[0203] A premix formulation of 150 g/L of bixlozone SC, 50 g/L of bixlozone CS, 125 g/L of beflubutamid SC, and 34.5 g/L of cloquintocet-mexyl SC was prepared by mixing appropriate quantities of the above compositions as follows.

[0204] Table 6. Premix composition A.

[0205] Premix composition B.

[0206] A premix formulation of 150 g/L of bixlozone SC, 50 g/L of bixlozone CS, 125 g/L of beflubutamid SC, and 34.5 g/L of cloquintocet-mexyl SC was prepared by mixing appropriate quantities of the above compositions as follows.

[0207] Table 7. Premix composition B.

[0208] Example 4. Stability studies.

[0209] Premix composition A and premix composition B were each aged at 40 °C for 8 weeks to study the accelerated storage stability of the formulations. Premix composition A solidified entirely in the oven at 40 °C, indicating the physical instability of premix composition A. In contrast, premix composition B remained liquid after 8 weeks at 40 °C with minimum particle growth, and also had good suspensibility upon diluting with water.

[0210] This example demonstrates the surprising enhancement in storage stability for premix composition B, which includes encapsulated beflubutamid, compared to premix composition A, which includes non-encapsulated beflubutamid. [0211] Example 5. Biological studies.

[0212] Efficacy protocol.

[0213] The treated plots were arranged in a randomized complete block of 6 meters of treated block and 2 meters width between the treated plots. Application was as follows: 360 g ai/ha, application 200 L/ha, mix size 96 L, Water volume 150-400 L/ha, horizontal boom sprayer.

[0214] Tested weeds included annual gross weeds (ALOMY and LOLSS) and broad leaf weeds (BRSNW, GALAP, LAMSS, PAPRH, STEME and VERSS) in a single preemergence application. Results are shown in Table 8. The numbers in parentheses indicate the number of treated plots. Premix composition B, EC composition, and Bixlozone SC formulation each have approximately the same loading of bixlozone.

[0215] Table 8. Weed control.

[0216] This example demonstrates the surprising enhancement in efficacy for premix composition B, which includes encapsulated beflubutamid, compared to other compositions in different forms.

Claims

WHAT IS CLAIMED IS: A composition comprising:

(i) encapsulated bixlozone;

(ii) non-encapsulated bixlozone;

(iii) encapsulated beflubutamid or an enantiomerically enriched form thereof;

(iv) optionally an encapsulated or non-encapsulated active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof; and

(v) optionally a non-encapsulated safener. The composition of claim 1, wherein the encapsulated bixlozone and the non-encapsulated bixlozone are present in a ratio in the range of from about 1:9 to about 9:1 The composition of any of claims 1-2, wherein the encapsulated bixlozone and the nonencapsulated bixlozone are present in a ratio in the range of from about 1 :3 to about 3:1 . The composition of any of claims 1-3, wherein the encapsulated bixlozone is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, polyacrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi- synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof. The composition of any of claims 1-4, wherein the encapsulated beflubutamid is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, polyacrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi- synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch. dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof. The composition of any of claims 1-5, wherein the composition is substantially free of nonencapsulated beflubutamid or an enantiomerically enriched form thereof. The composition of any of claims 1-6, wherein the additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is selected from acetochlor, acifluorfen, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amido sulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, benquinotrione, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bipyrazone, bispyribac, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, cypyrafluone, 2,4-D, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB, desmedipham, desmetryn, dicamba, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimesulfazet, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid, dinitramine, dinoterb, dioxopyritrione, diphenamid, diquat dibromide, dithiopyr, diuron. DNOC, endothal, EPTC, epyrifenacil, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, fluchloraminopyr, flufenacet, flufenoximacil, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac -pentyl, flumioxazin, fluometuron, fluoroglycofen -ethyl, flupoxam, fhrpyrsulfuron-methyl, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, flusulfinam, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, L- glufosinate-ammonium, glufosinate-P, glyphosate, halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin, icafolin, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, indolauxipyr, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil- sodium, ipfencarb azone, iptriazopyrid, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lancotrione, lenacil, linuron, maleic hydrazide, MCPA, MCPB, mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metproxybicyclone, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamidc, napropamidc-M, naptalam, ncburon, nicosulfuron, norflurazon, orbcncarb, ortho sulf amuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriflubenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimisoxafen, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr- triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron-methyl, tripyrasulfone, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4- hydroxy- 1 -methyl- 1 ,5-naphthyridin-2(lH)-one, 6-chloro-4-(2, 7 -dimethyl- l-naphthalenyl)-5- hydroxy-2-methyl-3(2H)-pyridazinone, 5-chloro-3-[(2-hydroxy-6-oxo-l-cyclohexen-l- yl)carbonyl]-l-(4-methoxyphenyl)-2(lH)-quinoxalinone, 2-chloro-AM l -methyl- l H-tctrazol-5- yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2- difluoroethyl)-8-hydroxypyrido[2,3-7»]pyrazin-6(5Z/)-one), 4-(2,6-diethyl-4-methylphenyl)-5- hydroxy-2,6-dimethyl-3(2/f)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5- dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (previously methioxolin), 4-(4-fluorophenyl)- 6-[(2-hydroxy-6-oxo-l-cyclohexen-l-yl)carbonyl]-2-methyl-l,2,4-triazine-3.5(2/7,4/7)-dione, methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2- pyridinecarboxylate, 2-methyl-3-(methylsulfonyl)-iV-(l-methyl-lH-tetrazol-5-yl)-4- (trifluoromethyl)benzamide, 2-methyl-A-(4-methy 1-1,2, 5-oxadiazol-3-yl)-3-(methy lsulfinyl)-4- (trifluoromethyl)benzamide, Alternaria destruens, Colletotrichum gloeosporiodes, Drechsiera monoceras, Myrothecium verrucaria, Phytophthora palmivora, Puccinia thlaspeos Schub, environmentally compatible salts, “acids”, esters, and amides thereof, and combinations thereof. The composition of any of claims 1-7, wherein the encapsulated additional active ingredient incompatible with beflubutamid or an enantiomerically enriched form thereof is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, polyacrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi- synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof. The composition of any of claims 1-8, wherein the encapsulated bixlozone is encapsulated separately from beflubutamid or an enantiomerically enriched form thereof. The composition of any of claims 1-8, wherein the bixlozone and beflubutamid or an enantiomerically enriched form thereof, are co-encapsulated. The composition of any of claims 1-10, wherein the safener is selected from benoxacor, cloquintocet, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, A-(aminocarbonyl)-2-methylbenzenesul fonamide and N- (aminocai‘bonyl)-2-fluorobenzenesulfonamide, l-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-l,3-dioxolane (MG 191), 4-(dichloroacetyl)-l-oxa- 4-azospiro[4.5]decane (MON 4660), 2,2-dichloro-l-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone, 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide, and combinations thereof. The composition of claim 11 wherein the safener is selected from benoxacor, cloquintocet, cloquintocet-mexyl, cyprosulfamide, dietholate, fenchlorazole-ethyl, fenclorim, isoxadifen-ethyl, mefenpyr-diethyl, naphthalic anhydride, and combinations thereof. The composition of claim 12 wherein the safener is selected from cloquintocet, cloquintocet-mexyl, dietholate, fenchlorazole-ethyl, fenclorim, isoxadifen-ethyl, mefenpyr-diethyl, naphthalic anhydride, and combinations thereof. The composition of claim 13 wherein the safener is selected from cloquintocet cloquintocet-mexyl, fenclorim, isoxadifen-ethyl, mefenpyr-diethyl, and combinations thereof. The composition of any of claims 1-14, wherein the composition further comprises an auxiliary selected from dispersants, surfactants, biocides, antifoamers, antifreeze agents, rheology modifiers, wetting agents, solvents, salts, and combinations thereof. The composition of any of claims 1-15, wherein the composition is in a form selected from a premix, a tank mix, and a ready-to-use formulation. A method of preparing a composition, the method comprising:

I) encapsulating bixlozone;

II) encapsulating beflubutamid or an enantiomerically enriched form thereof;

III) optionally encapsulating an active ingredient incompatible with beflubutamid; and IV) forming a mixture comprising:

(i) the encapsulated bixlozone;

(ii) optionally non-encapsulated bixlozone;

(iii) the encapsulated beflubutamid or an enantiomerically enriched form thereof;

(iv) optionally the encapsulated active ingredient incompatible with beflubutamid and/or a non-encapsulated active ingredient incompatible with beflubutamid; and

(v) optionally a non-encapsulated safener. The method of claim 17, wherein the encapsulated bixlozone is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, poly acrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi-synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof. The method of any of claims 17-18, wherein the encapsulated beflubutamid is encapsulated with a material selected from synthetic polymers, polyurcas, polyurethanes, polyacrylatcs, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semi-synthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof. The method of any of claims 17-19, wherein the additional active ingredient incompatible with beflubutamid is encapsulated with a material selected from synthetic polymers, polyureas, polyurethanes, polyacrylates, polyamides, polyvinyl alcohols, polyvinylpyrrolidones, semisynthetic materials, modified celluloses, modified starch derivatives, natural materials, gum Arabic, agar agar, dextrins, alginic acid, alginic acid salts, biodegradable natural polymers, collagen, polysaccharides, starch, dextrin, waxes, chitosan, alginate, cellulose, gelatin, derivatives thereof, and combinations thereof. The method of any of claims 17-20, wherein the encapsulated bixlozone is encapsulated separately from beflubutamid. A method for controlling undesirable vegetation, the method comprising applying to the undesirable vegetation or to a locus thereof or applying to a soil or water to prevent an emergence or growth of the undesirable vegetation a composition comprising:

(i) encapsulated bixlozone;

(ii) non-encapsulated bixlozone;

(iii) encapsulated beflubutamid or an enantiomeric ally enriched form thereof;

(iv) optionally an encapsulated or non-encapsulated active ingredient incompatible with beflubutamid; and

(v) optionally a non-encapsulated safener. The method of claim 22, wherein the undesirable vegetation comprises at least one herbicide resistant or tolerant weed species. The method of any of claims 22-23, wherein the undesirable vegetation comprises a weed selected from a broad leaf weed or a grass weed. The method of claim 24, wherein the undesirable vegetation is selected from Abutilon theophrasti (ABUTH), Acalypha virginica (ACCVI), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Ambrosia artemisiifolia (AMBEL), Anagallis arvensis (ANGAR), Apera spica-venti (APESV), Arrhenatherum elatius (ARREB), Calystegia sepium (CAGSE), Capsella bursa-pastoris (CAPBP), Centaurea cyanus (CENCY), Chenopodium album (CHEAL), Chenopodium hybridum (CHEHY), Chenopodium polyspermum (CHEPO), Convolvulus arvensis (CONAR), Cynodon dactylon (CYNDA), Cyperus difformis (CYPDI), Cyperus iria (CYPIR), Datura stramonium (DATST), Daucus carota (DAUCA), Descurainia sophia (DESSO), Digitaria sanguinalis (DIGS A), Echinochloa crus-galli (ECHCG), Echinochloa colonum (ECHCO), Fumaria officinalis (FUMOF), Galium aparine (GALAP), Galinsoga quadriradiata (GASCI), Geranium dissectum (GERDI), Geranium mole (GERMO), Geranium pusilium (GERPU). Hibiscus trionum (HIBTR), Lamium amplexicaule (LAMAM), Lamium purpureum (LAMPU), Buglossoides arvensis (LIT AR), Lolium multiflorum (LOLMU), Lolium perenne (LOLPE), Lolium rigidum (LOLRI), Matricaria chamomilla (MATCH), Tripleurospermum inodorum (MATIN), Mercurialis annua (MERAN), Panicum dichotomiflorum (PANDI), Panicum miliaceum (PANMI), Papaver rhoeas (PAPRH), Phalaris minor (PHAMI), Poa annua (POAAN), Polygonum aviculare (POLAV), Fallopia convolvulus (POLCO), Persicaria hydropiper (POLHY), Persicaria lapathifolia (POLLA), Persicaria maculosa (POLPE), Portulaca oleracea (POROL), Potentilla tridentate (PTLTR), Senecio vulgaris (SENVU), Setaria pumila (SETPU), Setaria viridis (SETVI), Solanum nigrum (SOLNI), Sorghum halepense (SORHA), Stellaria media (STEME), Trifolium incarnation (TRFIN), Veronica arvensis (VERAR), Veronica hederifolia (VERHE), Veronica persica (VERPE), Viola arvensis (VIOAR), and Xanthium strumarium (XANST), and combinations thereof. The method of any of claims 22-25, wherein the composition is applied at a stage selected from pre-emergence, post-emergence, and combinations thereof.