Description:TECHNICAL FIELD
[0001] The present disclosure generally relates to the technical field of herbicidal compositions. More particularly, the present disclosure provides a storage stable liquid composition of pinoxaden.
BACKGROUND
[0002] Background description includes information that may be useful in understanding the present invention. It is not an admission that any of the information provided herein is prior art or relevant to the presently claimed invention, or that any publication specifically or implicitly referenced is prior art.
[0003] Pinoxaden is chemically known as 8-(2,6-diethyl-p-tolyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo [1,2-d]1,4,5]oxadiazepine-9-yl-2,2-dimethylpropionate or 2,2-Dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5] oxa diazepin-7-yl ester. Pinoxaden exhibits herbicidal action against weeds in cereals, especially against grasses in wheat, barley and rye crops.
[0004] WO 99/47525 A1 discloses herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline derivatives, which includes Pinoxaden.
[0005] WO 01/17352 A1 discloses a selective herbicidal agent, characterized in that it contains, in addition to conventional inert formulation auxiliaries, a mixture of a) a herbicidally effective amount of a compound of the formula I (Pinoxaden); b) a herbicidally antagonistically effective amount of a safener selected from cloquintocet, an alkali, alkaline earth, sulfonium or ammonium cation of cloquintocet, cloquintocet mexyl, mefenpyr, an alkali, alkaline earth, sulfonium or ammonium cation of mefenpyr and mefenpyr and diethyl; and c) an additive containing an oil of vegetable or animal origin, or a Mineral oil, their alkyl esters or mixtures of these oils and oil derivatives.
[0006] While several liquid formulations of Pinoxaden has been reported so far, such conventional formulations suffer from a technical problem of chemical degradation of Pinoxaden i.e. chemical instability and/or physical instability. Few approaches have been reported to tackle physical and/or chemical stability of Pinoxaden in liquid compositions. For example, WO 2007/073933 A2 discloses a herbicidal composition in the form of an emulsifiable concentrate, which comprises in addition to emulsifiers and water–insoluble solvents, a) Pinoxaden and b) an alcohol selected from 2-ethyl hexanol, n-octanol, benzyl-alcohol, tetrhydrofurfuryl alcohol, 2-methyl pentane diol, 4-hydroxy-4-methyl-2-pentanone, cyclohexanol, methyl-lactate and butyl-lactate; and WO 2008/049618 A1 discloses a liquid herbicidal composition comprising pinoxaden in an amount of 0.5 - 50 % and an adjuvant in an amount of 2 - 80 %, where the adjuvant is a built-in adjuvant consisting of a tris-(2-ethylhexyl) phosphate, wherein the percentage of breakdown of pinoxaden is less than 2.5% after 2 weeks storage at a temperature of 50˚C.
[0007] Accordingly, there is a long-felt need in the art for improved compositions and formulations of Pinoxaden. The present disclosure provides a storage stable liquid composition comprising Pinoxaden, which is highly effective and also chemically and physically stable.
[0008] All publications herein are incorporated by reference to the same extent as if each individual publication or patent application were specifically and individually indicated to be incorporated by reference. Where a definition or use of a term in an incorporated reference is inconsistent or contrary to the definition of that term provided herein, the definition of that term provided herein applies and the definition of that term in the reference does not apply.
OBJECTS
[0009] An object of the present disclosure is to provide a liquid composition of pinoxaden that has excellent storage stability.
[0010] Another object of the present disclosure is to provide a liquid composition of pinoxaden that is economical.
[0011] Further object of the present disclosure relates to a method for preparation of a liquid composition of pinoxaden.

SUMMARY
[0012] The present disclosure generally relates to the technical field of herbicidal compositions. More particularly, the present disclosure provides a storage stable liquid composition of pinoxaden.
[0013] The present disclosure is, at least in part, on the premise of a surprising observation by inventors of the present application, that incorporating a combination of alkoxylated polyol ester (built-in adjuvant) and an alcohol dramatically reduces chemical degradation of pinoxaden in liquid compositions.
[0014] Accordingly, an aspect of the present disclosure provides a liquid herbicidal composition, said composition comprising: (a) pinoxaden in an amount ranging from 0.5 to 50 wt.% by weight of the composition; (b) a built-in adjuvant in an amount ranging from 10 to 40 wt.% by weight of the composition, said built-in adjuvant being an alkoxylated polyol ester; and (c) an alcohol in an amount ranging from 0.5 to 20 wt.% by weight of the composition.
[0015] In some embodiments, the alcohol comprises an aliphatic alcohol.
[0016] In some embodiments, the composition includes: (a) pinoxaden in an amount ranging from 0.5 to 30 wt.% by weight of the composition; (b) a built-in adjuvant in an amount ranging from 10 to 40 wt.% by weight of the composition, said built-in adjuvant being an alkoxylated polyol ester; (c) an aliphatic alcohol in an amount ranging from 0.5 to 20 wt.% by weight of the composition; (d) a safener in an amount ranging from 0.5 to 20 wt.% by weight of the composition; (e) an emulsifier in an amount ranging from 1 to 20 wt.% by weight of the composition; and (f) a solvent in an amount ranging from 20 to 75 wt.% by weight of the composition.
[0017] In some embodiments, the aliphatic alcohol comprises 2-butoxy ethanol. In some embodiments, the safener comprises Cloquintocet or ester thereof. In some embodiments, the solvent comprises an aromatic solvent.
[0018] In some embodiments, the composition consists of: (a) pinoxaden in an amount ranging from 0.5 to 30 wt.% by weight of the composition; (b) a built-in adjuvant in an amount ranging from 10 to 40 wt.% by weight of the composition, said built-in adjuvant comprising alkoxylated polyol ester; (c) an aliphatic alcohol in an amount ranging from 0.5 to 20 wt.% by weight of the composition; (d) a safener in an amount ranging from 0.5 to 20 wt.% by weight of the composition; (e) an emulsifier in an amount ranging from 1 to 20 wt.% by weight of the composition; and (f) a solvent in an amount ranging from 20 to 75 wt.% by weight of the composition.
[0019] In some embodiments, the composition is prepared in form of an emulsion concentrate (EC).
[0020] Various objects, features, aspects and advantages of the inventive subject matter will become more apparent from the following detailed description of preferred embodiments.

DETAILED DESCRIPTION
[0021] The following is a detailed description of embodiments of the present invention. The embodiments are in such detail as to clearly communicate the invention. However, the amount of detail offered is not intended to limit the anticipated variations of embodiments; on the contrary, the intention is to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the present invention as defined by the appended claims.
[0022] Each of the appended claims defines a separate invention, which for infringement purposes is recognized as including equivalents to the various elements or limitations specified in the claims. Depending on the context, all references below to the “invention” may in some cases refer to certain specific embodiments only. In other cases it will be recognized that references to the “invention” will refer to subject matter recited in one or more, but not necessarily all, of the claims.
[0023] Groupings of alternative elements or embodiments of the invention disclosed herein are not to be construed as limitations. Each group member can be referred to and claimed individually or in any combination with other members of the group or other elements found herein. One or more members of a group can be included in, or deleted from, a group for reasons of convenience and/or patentability.
[0024] Unless the context requires otherwise, throughout the specification which follow, the word “comprise” and variations thereof, such as, “comprises” and “comprising” are to be construed in an open, inclusive sense that is as “including, but not limited to.” It is to be appreciated that the terms "comprising", "comprises" and "comprised of" as used herein includes the terms "consisting of", "consists" and "consists of" within their meaning.
[0025] Reference throughout this specification to “one embodiment” or “an embodiment” means that a particular feature, structure or characteristic described in connection with the embodiment is included in at least one embodiment. Thus, the appearances of the phrases “in one embodiment” or “in an embodiment” in various places throughout this specification are not necessarily all referring to the same embodiment. Furthermore, the particular features, structures, or characteristics may be combined in any suitable manner in one or more embodiments.
[0026] As used in the description herein and throughout the claims that follow, the meaning of “a,” “an,” and “the” includes plural reference unless the context clearly dictates otherwise. Also, as used in the description herein, the meaning of “in” includes “in” and “on” unless the context clearly dictates otherwise.
[0027] In some embodiments, the numbers expressing quantities of ingredients, properties such as concentration, and so forth, used to describe and claim certain embodiments of the invention are to be understood as being modified in some instances by the term “about.” Accordingly, in some embodiments, the numerical parameters set forth in the written description are approximations that can vary depending upon the desired properties sought to be obtained by a particular embodiment. In some embodiments, the numerical parameters should be construed in light of the number of reported significant digits and by applying ordinary rounding techniques. Notwithstanding that the numerical ranges and parameters setting forth the broad scope of some embodiments of the invention are approximations, the numerical values set forth in the specific examples are reported as precisely as practicable.
[0028] The recitation of ranges of values herein is merely intended to serve as a shorthand method of referring individually to each separate value falling within the range. Unless otherwise indicated herein, each individual value is incorporated into the specification as if it were individually recited herein.
[0029] The headings and abstract of the invention provided herein are for convenience only and do not interpret the scope or meaning of the embodiments.
[0030] All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and all examples, or exemplary language (e.g. “such as”) provided with respect to certain embodiments herein is intended merely to better illuminate the invention and does not pose a limitation on the scope of the invention otherwise claimed. No language in the specification should be construed as indicating any non-claimed element essential to the practice of the invention.
[0031] The following discussion provides many example embodiments of the inventive subject matter. Although each embodiment represents a single combination of inventive elements, the inventive subject matter is considered to include all possible combinations of the disclosed elements. Thus if one embodiment comprises elements A, B, and C, and a second embodiment comprises elements B and D, then the inventive subject matter is also considered to include other remaining combinations of A, B, C, or D, even if not explicitly disclosed.
[0032] Various terms as used herein are shown below. To the extent a term used in a claim is not defined below, it should be given the broadest definition persons in the pertinent art have given that term as reflected in printed publications and issued patents at the time of filing.
[0033] The present disclosure generally relates to the technical field of herbicidal compositions. More particularly, the present disclosure provides a storage stable liquid composition of pinoxaden.
[0034] An aspect of the present disclosure provides a liquid herbicidal composition, said composition comprising: (a) pinoxaden in an amount ranging from 0.5 to 50 wt.% by weight of the composition; (b) a built-in adjuvant in an amount ranging from 10 to 40 wt.% by weight of the composition, said built-in adjuvant being an alkoxylated polyol ester; and (c) an alcohol in an amount ranging from 0.5 to 20 wt.% by weight of the composition.
[0035] In some embodiments, pinoxaden is present in an amount ranging from 0.5 to 50 wt.% by weight of the composition, for example, from about 1 to about 40 wt.% by weight of the composition, or from about 2 to about 25 wt.% by weight of the composition, or from about 3 to about 15 wt.% by weight of the composition. In one embodiment, pinoxaden is present in an amount ranging from about 1 to about 10 wt.% by weight of the composition.
[0036] Exemplary alcohols that may be for realizing the composition of the present disclosure include, but not limited to, C1-C12 alkanols such as methanol, ethanol, propanol, hexanol, octanol and dodecanol. The alcohols may be straight-chain or branched, for example, 2-ethylhexanol; may be present in the form of diols or triols, such as, propylene glycol, dipropylene glycol, or 2-methyl-2,4-pentanediol; and may also be optionally substituted, such as, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, 4-hydroxy-4-methyl-2-pentanone; and may be present in the form of lactic acid alkyl esters, such as, ethyl lactate, and butyl lactate. Cyclic alcohols, such as, cyclopentanol or cyclohexanol, can likewise be used. Preferred alcohols for realizing the composition of the present disclosure can be selected from the group consisting of: 2-ethylhexanol, 2-butoxy ethanol, n-octanol, tetrahydrofurfuryl alcohol, 2-methyl-2,4- pentanediol, 4-hydroxy-4-methyl-2-pentanone, lactic acid methylester, lactic acid butylester, cyclohexanol, benzyl alcohol, benzyl benzoate, benzyl lactate, N-methyl pyrrolidone, gamma- butyrolactone, dimethylsulfoxide, ethyl lactate, and a mixture of one or more of these alcohols. In some embodiments, the alcohol comprises an aliphatic alcohol. In some embodiments, the aliphatic alcohol comprises 2-butoxyethanol. In some embodiments, the alcohol comprises an aliphatic branched alcohol having C2-C8. In an embodiment, the alcohol is 2-butoxyethanol.
[0037] In some embodiments, the alcohol is present in an amount ranging from about 0.5 to about 15 wt.% by weight of the composition, for example, from about 1 to about 15 wt.% by weight of the composition, or from about 3 to about 15 wt.% by weight of the composition, or from about 5 to about 15 wt.% by weight of the composition. In one embodiment, the alcohol is present in an amount ranging from about 5 to about 15 wt.% by weight of the composition.
[0038] In some embodiments, the built-in adjuvant (alkoxylated polyol ester) is present in an amount ranging from 10 to 40 wt.% by weight of the composition, for example, from about 10 to about 35 wt.% by weight of the composition, or from about 15 to about 30 wt.% by weight of the composition, or from about 20 to about 30 wt.% by weight of the composition. In one embodiment, the alcohol is present in an amount ranging from about 20 to about 30 wt.% by weight of the composition.
[0039] In some embodiments, the composition includes: (a) pinoxaden in an amount ranging from 0.5 to 30 wt.% by weight of the composition; (b) a built-in adjuvant in an amount ranging from 10 to 40 wt.% by weight of the composition, said built-in adjuvant being an alkoxylated polyol ester; (c) an aliphatic alcohol in an amount ranging from 0.5 to 20 wt.% by weight of the composition; (d) a safener in an amount ranging from 0.5 to 20 wt.% by weight of the composition; (e) an emulsifier in an amount ranging from 1 to 20 wt.% by weight of the composition; and (f) a solvent in an amount ranging from 20 to 75 wt.% by weight of the composition.
[0040] In some embodiments, the safener is selected from a group consisting of: cloquintocet; an alkali metal, alkaline earth metal, sulfonium or ammonium cation of cloquintocet; cloquintocet-mexyl; mefenpyr; an alkali metal, alkaline earth metal, sulfonium or ammonium cation of mefenpyr; and mefenpyr-diethyl. In some embodiments, the safener is cloquintocet-mexyl. In some embodiments, the safener is present in an amount ranging from about 0.5 to about 15 wt.% by weight of the composition, for example, from about 0.5 to about 10 wt.% by weight of the composition, or from about 0.5 to about 7 wt.% by weight of the composition, or from about 0.5 to about 5 wt.% by weight of the composition. In one embodiment, the safener is present in an amount ranging from about 0.5 to about 5 wt.% by weight of the composition.
[0041] In some embodiments, the solvent is a water insoluble solvent. Exemplary water-insoluble solvents that may be used for preparation of composition of the present disclosure include, but not limited to, aromatic hydrocarbons, such as toluene, xylene, cumene, mixtures of aromatic hydrocarbons having a boiling point from 160 to 180°C (Solvesso 100) or from 180 to 210°C (Solvesso 150) or from 230 to 290°C (Solvesso 200, Solvesso 200ND), aliphatic or cycloaliphatic hydrocarbons (Exxsol D80, Exxsol D100, Exxsol D120, lsopar H and lsopar V), fatty alcohol acetates (Exxate 700, Exxate 1000), isobomyl acetate, benzyl acetate, lower alkyl esters of dicarboxylic acids such as maleic, fumaric, succinic, glutaric and adipic acid (Solvent DBE), esters of benzoic acid such as benzyl benzoate, methyl benzoate and dipropylene glycol dibenzoate, as well as lower alkyl esters of higher fatty acids such as C8-C10 fatty acid methyl esters and C16-C18 fatty acid methyl esters, and ketones such as cyclohexanone, acetophenone, methyl-n-pentyl ketone. The water-insoluble solvent may be present in the composition in an amount ranging from about 20 to about 70% w/w of the composition. In some embodiments, the solvent comprises an aromatic solvent. In some embodiments, the aromatic solvent comprises a mixture of aromatic solvents having a boiling point from 230 to 290°C.
[0042] In some embodiments, the solvent is present in an amount ranging from about 25 to about 70 wt.% by weight of the composition, for example, from about 30 to about 70 wt.% by weight of the composition, or from about 35 to about 65 wt.% by weight of the composition or about 40 to about 60 wt.% by weight of the composition. In an embodiment, the solvent is present in an amount ranging from about 40 to about 70 wt.% by weight of the composition.
[0043] Exemplary emulsifiers that may be used for preparation of composition of the present disclosure include, but not limited to, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of arylsulfonates, such as calcium dodecylbenzenesulfonate; alkyl arylsulfonates or salts thereof (e.g. AtloxTM 4838B); polyisobutylene succinic anhydride-polyethylene glycol (AtloxTM 4914); alkylphenol-alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkyl phosphate esters. It is also possible to use a mixture of one or more of these emulsifiers. In some embodiments, the emulsifier comprises a combination of a salt of arylsulfonate (e.g. AtloxTM 4838B), and polyisobutylene succinic anhydride-polyethylene glycol (e.g. AtloxTM 4914).
[0044] In some embodiments, the emulsifier is present in an amount ranging from about 1 to about 20 wt.% by weight of the composition, for example, from about 3 to about 20 % by weight of the composition, or from about 4 to about 20 % by weight of the composition, or from about 5 to about 20 % by weight of the composition. In an embodiment, the emulsifier is present in an amount ranging from about 3 to about 20 % by weight of the composition.
[0045] In an exemplary embodiment of the present disclosure, the composition includes: (a) pinoxaden in an amount ranging from about 1 to about 10 wt.% by weight of the composition; (b) a built-in adjuvant in an amount ranging from 10 to 30 wt.% by weight of the composition, said built-in adjuvant comprising alkoxylated polyol ester (e.g. AtplusTM UEP100); (c) an aliphatic alcohol in an amount ranging from 5 to 15 wt.% by weight of the composition; (d) a safener in an amount ranging from 0.5 to 10 wt.% by weight of the composition; (e) an emulsifier in an amount ranging from 1 to 20 wt.% by weight of the composition; and (f) a solvent in an amount ranging from 20 to 75 wt.% by weight of the composition.
[0046] In some embodiments, the composition optionally further includes a co-herbicide. The co-herbicide may be selected from the group consisting of: aryloxy- and heteroaryloxyphenoxy propionic acids, cyclohexandiones, sulfonyl urea, triazolopyrimidines, nitriles, thiocarbamates, dinitroanilines, benzoic acids, phenoxy acids and pyridine carboxylicacids. Of particular interest are clodinafop, fenoxaprop, tralkoxydim, prosulfocarb, triasulfuron, prosulfuron, amidosulfuron, iodosulfuron, chlorsulfuron, flupyrsulfuron, mesosulfuron, metsulfuron, sulfosulfuron, thifensulfuron, tribenuron, tritosulfuron, florasulam, metosulam, flumetsulam, pyroxsulam, 2,4-D, 2,4-DP, dichlorprop-p, MCPA, mecoprop, mecoprop-p, MCPB, clopyralid, bromoxynil, bromoxynil-octanoate, ioxynil, ioxynil-octanoate, fluroxypyr, trifluralin, diflufenican, picolinafen, pendimethalin and triallate, where tralkoxydim, triasulfuron, diflufenican, florasulam, pyroxsulam, pyroxsulam in combination with cloquintocet, clodinafop and clodinafop in combination with cloquintocet are preferred. The co-herbicide, if used, can be present in the composition in an amount of about 0.1 to about 30% w/w of the composition.
[0047] In some embodiments, the composition further includes one or more excipients that include, but not limited to, crystallisation inhibitors, viscosity-modifying substances, suspending agents, dyes, antioxidants, foaming agents, anti-foaming agents, light absorbers, mixing aids, complexing agents, neutralising or pH-modifying substances and buffers, corrosion-inhibitors, fragrances, wetting agents, absorption improvers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, anti-freezes, microbiocides, liquid fertilisers, and solid fertilisers.
[0048] In some embodiments, the composition consists of: (a) pinoxaden in an amount ranging from 0.5 to 30 wt.% by weight of the composition; (b) a built-in adjuvant in an amount ranging from 10 to 40 wt.% by weight of the composition, said built-in adjuvant comprising alkoxylated polyol ester; (c) an aliphatic alcohol in an amount ranging from 5 to 30 wt.% by weight of the composition; (d) a safener in an amount ranging from 0.5 to 20 wt.% by weight of the composition; (e) an emulsifier in an amount ranging from 1 to 20 wt.% by weight of the composition; and (f) a solvent in an amount ranging from 20 to 75 wt.% by weight of the composition.
[0049] In some embodiments, the composition of the present disclosure are prepared in the form of an emulsion concentrate (EC), oil dispersion (OD), dispersible concentrate (DC), suspo- emulsion (SE) or emulsion in water (EW). It is also possible that the emulsions are present in the form of gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent compressed tablets, microemulsifiable concentrates, oil-in-water emulsions, oil flowables, aqueous dispersions, capsule suspensions, emulsifiable granules, or in other forms known in the art. Such formulations can either be used directly or are diluted prior to use. Diluted formulations can be prepared, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents. In some embodiments, the composition of the present disclosure is prepared in the form of an emulsion concentrate (EC).
[0050] The composition of the present disclosure can be prepared, for example, by mixing the active ingredient (i.e. pinoxaden, optionally in combination with a co-herbicide and/or a safener) with one or more excipients in order to obtain the composition in the form of solution, dispersion or emulsion.
[0051] In some embodiments, the present disclosure relates also to a method for inhibiting or controlling undesirable plant growth, wherein a herbicidally effective amount of the composition of the present disclosure is applied to the plants or their habitat.
[0052] Another aspect of the present disclosure relates to a process for preparation of a liquid herbicidal composition, said process comprising the steps of: (i) mixing a water-insoluble solvent and an alcohol; (ii) adding a safener to the mixture of step (i); (iii) adding pinoxaden to the mixture obtained in step (ii); (iv) adding a built-in adjuvant and an emulsifier to the mixture of step (iii), said built-in adjuvant being an alkoxylated polyol ester; and (ii) formulating the mixture of step (iv) into the liquid herbicidal composition. In some embodiments, the composition is formulated into an emulsion concentrate (EC).
[0053] In some embodiments, the composition prepared by the process above comprises: (a) pinoxaden in an amount ranging from 0.5 to 30 wt.% by weight of the composition; (b) the built-in adjuvant in an amount ranging from 10 to 40 wt.% by weight of the composition, said built-in adjuvant being an alkoxylated polyol ester; (c) the alcohol in an amount ranging from 0.5 to 20 wt.% by weight of the composition; (d) the safener in an amount ranging from 0.5 to 20 wt.% by weight of the composition; (e) the emulsifier in an amount ranging from 1 to 20 wt.% by weight of the composition; and (f) the solvent in an amount ranging from 20 to 75 wt.% by weight of the composition.
[0054] The present disclosure also relates to a process for preparation of an emulsifiable concentrate (EC) composition, the process comprising the steps of: (i) mixing pinoxaden with one or more excipients; and (ii) formulating the blend of step (i) into an emulsifiable concentrate (EC) composition.
[0055] In some embodiments, the process for preparation of an emulsifiable concentrate composition comprises the steps of: (i) mixing pinoxaden with a safener and one or more excipients; and (ii) formulating the blend of step (i) into an emulsifiable concentrate composition.
[0056] In some embodiments, the process for preparation of an emulsifiable concentrate composition comprises the steps of: (i) mixing a water-insoluble solvent and an alcohol; (ii) adding a safener to the mixture of step (i); (iii) adding pinoxaden to the mixture obtained in step (ii); (iv) adding an adjuvant and an emulsifier to the mixture of step (iii); and (ii) formulating the mixture of step (iv) into an emulsifiable concentrate composition.
[0057] While the foregoing description discloses various embodiments of the disclosure, other and further embodiments of the invention may be devised without departing from the basic scope of the disclosure. The invention is not limited to the described embodiments, versions or examples, which are included to enable a person having ordinary skill in the art to make and use the invention when combined with information and knowledge available to the person having ordinary skill in the art.
EXAMPLES
[0058] Example 1: Emulsifiable concentrate (EC) composition of Pinoxaden
[0059] An emulsifiable concentrate formulation was prepared, composition details wherefor are shown below in Table 1.

Table 1: Composition for an emulsifiable concentrate formulation of Pinoxaden
S. No Component Name Quantity (% w/w)
1 Pinoxaden a.i. 5.10
2 Cloquintocet mexyl ester 1.26
3 Nonionic polymeric surfactant with a low HLB value (Atlox™ 4914) 3.00
4 Calcium alkylaryl sulphonate in aromatic solvent (Atlox™ 4838B) 3.00
5 Alkoxylated polyol ester (Atplus™ UEP100) 26.00
6 2-butoxy ethanol 10.00
7 Aromatic fluid (Solvesso™ 200 ND) 51.64

[0060] The processing steps involved in manufacturing of the emulsifiable concentrate formulation are as follows: (i) 2-butoxy ethanol and Solvesso 200 ND were mixed in a suitable vessel and stirred for 5 min.; (ii) Cloquintocet Mexyl ester was added to the above step 1 and stirred for 30 min to get a clear solution; (iii) Pinoxaden was added to the above solution of step (ii) and stirred for 30 min to get a clear solution; and (iv) Atlox UEP 100 was added to the solution of step (iii) followed by Atlox 4914 and Atlox 4838B and stirred for 30 min. to obtain the EC formulation.
[0061] Example 2: Emulsifiable concentrate composition of Pinoxaden
[0062] An emulsifiable concentrate formulation was prepared, composition details wherefor are shown below in Table 2. The processing steps involved in manufacturing of the emulsifiable concentrate formulation were same as mentioned in example 1 above.

Table 2: Composition for an emulsifiable concentrate formulation of Pinoxaden
S. No Component Name Quantity (% w/w)
1 Pinoxaden a.i. 5.10
2 Cloquintocet mexyl ester 1.26
3 Nonionic polymeric surfactant with a low HLB value (Atlox 4914) 3.00
4 Calcium alkylaryl sulphonate in aromatic solvent (Atlox 4838B) 3.00
5 Alkoxylated polyol ester (Atplus UEP100) 20.00
6 Polyoxyethylene (16) sorbitan monolaurate (Tween 24) 6.00
7 2-butoxy ethanol 10.00
8 Aromatic fluid (Solvesso 200 ND) 51.64

[0063] Comparative Example 3: Emulsifiable concentrate composition of Pinoxaden
[0064] An emulsifiable concentrate formulation was prepared, composition details wherefor are shown below in Table 3. The processing steps involved in manufacturing of the emulsifiable concentrate formulation were same as mentioned in example 1 above.
Table 3: Composition for an emulsifiable concentrate formulation of Pinoxaden
S. No Component Name Quantity (% w/w)
1 Pinoxaden a.i. 5.10
2 Cloquintocet mexyl ester 1.26
3 Nonionic polymeric surfactant with a low HLB value (Atlox 4914) 3.00
4 Calcium alkylaryl sulphonate in aromatic solvent (Atlox 4838B) 3.00
5 Alkoxylated polyol ester (Atplus UEP100) 26.00
6 N,N-Dimethylformamide (DMF) 10.00
7 Aromatic fluid (Solvesso 200 ND) 51.64

[0065] Comparative Example 4: Emulsifiable concentrate composition of Pinoxaden
[0066] An emulsifiable concentrate formulation was prepared, composition details wherefor are shown below in Table 4. The processing steps involved in manufacturing of the emulsifiable concentrate formulation were same as mentioned in example 1 above.
Table 4: Composition for an emulsifiable concentrate formulation of Pinoxaden
S. No Component Name Quantity (% w/w)
1 Pinoxaden a.i. 5.10
2 Cloquintocet mexyl ester 1.26
3 Nonionic polymeric surfactant with a low HLB value (Atlox 4914) 3.00
4 Calcium alkylaryl sulphonate in aromatic solvent (Atlox 4838B) 3.00
5 Alkoxylated polyol ester (Atplus UEP100) 20.00
6 Polyoxyethylene (16) sorbitan monolaurate (Tween 24) 6.00
7 N,N-Dimethylformamide (DMF) 10.00
8 Aromatic fluid (Solvesso 200 ND) 51.64

[0067] Assay, Water Content and Physical Attributes of the EC formulations
[0068] The Emulsifiable concentrate formulations prepared in each of the Examples 1-4 were subjected to an assay for determining the amount of Pinxadent and water content of the formulations at initial, 7 days and 14 days after storage at room temperature (RT) and at 54°C. Results from the studies are provided in Table 5 below:
Table 5: Assay and Water Content of EC formulations
Parameter Storage condition – Time period Ex-1 Ex-2 Ex-3 Ex-4
Assay (%) RT – Initial 101.9 101.2 99.6 98.3
RT - 14 days 100.9 100.7 97.9 96.4
54°C - 7 days 100 98.6 82.8 81.4
54°C - 14 days 99 96.8 63.6 62.5
Water content (%) RT – Initial 0.27 0.36 0.42 0.61
RT - 14 days 0.32 0.39 0.45 0.54
54°C - 7 days 0.28 0.36 0.42 0.49
54°C - 14 days 0.28 0.36 0.37 0.45
[0069] The Emulsifiable concentrate formulations prepared in each of the Examples 1-4 were also subjected to measurement of physical attributes, results wherefor are provided in Table 6 below:
Table 6: Physical attributes of the EC formulations
Test Ex-1 Ex-2 Ex-3 Ex-4

Blooming* √√√√ √√√√ √√√√ √√√√
Wettability* √√√√ √√√√ √√√√ √√√√
Blue tint* √√√√ √√√√ √√√√ √√√√
*Note: √- Poor, √√- Good, √√√- Very Good, √√√√- Excellent
[0070] As can be seen from Table 5 and 6 above, formulations/compositions including a combination of Alkoxylated polyol ester and alcohol (specifically, an aliphatic alcohol) affords dramatic improvement in chemical stability of Pinoxaden with excellent physical attributes. Accordingly, it is concluded that ingredients of the composition - Alkoxylated polyol ester, alcohol, and Pinoxaden exhibit excellent synergy and functional reciprocity therebetween. As can also be seen from Table 5 and 6 above, compositions devoid of the combination of Alkoxylated polyol ester and alcohol (specifically, an aliphatic alcohol), while having excellent physical attributes, could not prevent chemical degradation of Pinoxaden to the desired extent.
[0071] A skilled artisan would also appreciate that, a safener, owing to its strong synergy and functional reciprocity, increases the tolerance of target plant(s) to the herbicide without affecting the weed control effectiveness of the herbicide. It is well known scientific fact that Cloquintocet Mexyl acts as a safener when used in combination with Pinoxaden, for example, WO 01/17352 A1 discloses compositions comprising a combination of herbicide and Cloquintocet Mexyl as a safener, contents whereof are incorporated herein in its entirety by way of reference. The compositions of the present disclosure are based on, in part, the well established scientific principle of existence of synergy and functional reciprocity between Pinoxaden and Cloquintocet Mexyl.
FIELD TRIALS
[0072] The EC formulation realized in Example 1 above was subjected to field trials to evaluate the bio-efficacy and Phytotoxicity thereof against Phalaris minor (Canary grass) and Avena sp (Wild oat) in wheat crop. Protocol/details for the field trial is provided in Table 7 below. Treatment details are provided in Table 8 below.

Table 7: Field Trial Details
Crop & Variety Wheat & UAS 334
Targeted weeds to be controlled Phalaris minor (Canary grass) and Avena sp (Wild oat)
Plot Size 6 m  5 m
Design Randomized Block Design (RBD)
Number of applications One
Type of Soil / Land Black soil
Mode of Application Single nozzle Knapsack sprayer
Type of Application Spray
Time and frequency of Application 35 days after sowing

Table 8: Treatment Details
Treatment Details* Dosage
(gm a.i./ha) Formulation (ml)
Pinoxaden 5.1 EC – Test Sample 45 900
Pinoxaden 5.1 EC – Market Sample 45 900
*Note: Code “Pinoxaden 5.1 EC” denotes the EC formulation of Example 1
Weed intensity:
[0073] Weed count: The number of species wise weeds was determined at pre-spray, 30 Days after spray (DAS), 60 DAS and at harvest at about 5 locations per plot using a square quadrant, 1 sq.m.using a square quadrant, 1 sq.m at about five locations per plot.
[0074] Weed Dry Matter: Dry or fresh weight of weeds species wise were determined at pre-spray, 30 DAS, 60 DAS and at Harvest and statistically analysed after transformation.
[0075] Percent weed control efficiency (WCE): Weed control efficiency was mentioned species wise at 30 DAS, 60 DAS and at harvest. Weed Control Efficiency (WCE) was calculated using below formula:
WCE % = (Dry Weight in control) – (Dry Weight treatment) X 100
(Dry Weight in control)

[0076] The Percent weed control efficiency (WCE) was calculated based on the weed density of Phalaris minor (Canary grass) and Avena. Sp (Wild oat) at 60 days after application and the results are provided in the Table 9 below:
Table 8: Comparative weed control efficiency of formulations
S. No Treatment g a.i / ha Formulation Dose Percent weed control efficiency (WCE) at 60 days after application
Phalaris minor Avena. Sp
1 Pinoxaden 5.1% EC formulation
(Test sample) 45 900 ml 94.03 93.33
2 Pinoxaden 5.1% EC formulation
(Market sample) 45 900 ml 92.75 83.89

[0077] The above data clearly indicates that the Pinoxaden 5.1% EC formulation (Test sample) realized according to the present invention is better than the Marketed Pinoxaden 5.1% EC formulation in terms of its weed control activity/efficacy.

ADVANTAGES
[0078] The present disclosure provides a liquid composition of pinoxaden that has excellent storage stability.
[0079] The present disclosure provides a liquid composition of pinoxaden that is economical.
[0080] The present disclosure provides a method for preparation of a liquid composition of pinoxaden, which has excellent storage stability.
, Claims:1. A liquid herbicidal composition, said composition comprising:
(a) pinoxaden in an amount ranging from 0.5 to 50 wt.% by weight of the composition;
(b) a built-in adjuvant in an amount ranging from 10 to 40 wt.% by weight of the composition, said built-in adjuvant being an alkoxylated polyol ester; and
(c) an alcohol in an amount ranging from 0.5 to 20 wt.% by weight of the composition.
2. The composition as claimed in claim 1, wherein the alcohol comprises an aliphatic alcohol.
3. The composition as claimed in claim 2, wherein the aliphatic alcohol comprises 2-butoxy ethanol.
4. The composition as claimed in claim 1, wherein the composition comprises:
(a) pinoxaden in an amount ranging from 0.5 to 30 wt.% by weight of the composition;
(b) a built-in adjuvant in an amount ranging from 10 to 40 wt.% by weight of the composition, said built-in adjuvant being an alkoxylated polyol ester;
(c) an aliphatic alcohol in an amount ranging from 0.5 to 20 wt.% by weight of the composition;
(d) a safener in an amount ranging from 0.5 to 20 wt.% by weight of the composition;
(e) an emulsifier in an amount ranging from 1 to 20 wt.% by weight of the composition; and
(f) a solvent in an amount ranging from 20 to 75 wt.% by weight of the composition.
5. The composition as claimed in claim 4, wherein the safener comprises Cloquintocet or ester thereof.
6. The composition as claimed in claim 4, wherein the solvent comprises an aromatic solvent.
7. The composition as claimed in claim 1, wherein the composition consists of:
(a) pinoxaden in an amount ranging from 0.5 to 30 wt.% by weight of the composition;
(b) a built-in adjuvant in an amount ranging from 10 to 40 wt.% by weight of the composition, said built-in adjuvant comprising alkoxylated polyol ester;
(c) an aliphatic alcohol in an amount ranging from 0.5 to 20 wt.% by weight of the composition;
(d) a safener in an amount ranging from 0.5 to 20 wt.% by weight of the composition;
(e) an emulsifier in an amount ranging from 1 to 20 wt.% by weight of the composition; and
(f) a solvent in an amount ranging from 20 to 75 wt.% by weight of the composition.
8. The composition as claimed in claim 1, wherein the composition is prepared in form of an emulsion concentrate (EC).
9. A process for preparation of a liquid herbicidal composition, said process comprising the steps of:
(i) mixing a water-insoluble solvent and an alcohol;
(ii) adding a safener to the mixture of step (i);
(iii) adding pinoxaden to the mixture obtained in step (ii);
(iv) adding a built-in adjuvant and an emulsifier to the mixture of step (iii), said built-in adjuvant being an alkoxylated polyol ester; and
(ii) formulating the mixture of step (iv) into the liquid herbicidal composition.

10. The process as claimed in claim 9, wherein the composition is formulated into an emulsion concentrate (EC).