Liquid agrochemical composition comprising hexazinone and a lactone

Abstract

An agrochemical liquid composition of hexazinone and at least one γ- or δ-lactone.

Description

[0001] ARE Docket 92513-A-PCT / GJG / LL

[0002] LIQUID AGROCHEMICAL COMPOSITION COMPRISING HEXAZINONE AND A LACTONE FIELD OF THE INVENTION

[0003] The present invention belongs to the field of agrochemistry. It is directed to a liquid hexazinone composition for agricultural applications, to a process for preparation thereof and to methods for controlling weeds.

[0004] This application claims the benefit of U.S. Provisional Application No. 63 / 747,844, filed January 21, 2025, the contents of which are hereby incorporated by reference.

[0005] BACKGROUND

[0006] There is an interest in the field of agrochemistry of liquid stable formulations containing hexazinone. The prior art discloses different types of formulations comprising hexazinone as active ingredient. The prior art document DE 102005006411 discloses a synergistic triple mixture combination of a sulfonyl urea, an urea, and a triazine active ingredients, wherein the triazine active ingredient may be hexazinone and the composition may contain as auxiliary material, for example, a liquid carrier selected, for example, from water, glycols, alcohols or y-butyrolactone among many other liquid carriers. The amount of auxiliary materials may range from 1 to 99.9 percent by weight of the composition, and in the particular case of a liquid emulsion concentrate composition, the amount of liquid carrier is the remaining amount for a composition that contains from 1 to 95% by weight of active ingredients, and 1 to 30% by weight of surfactants. The document W02009 / 054823 A2 refers to a mixture composition that contains at least one sulfonyl urea, diuron and hexazinone. The composition may contain as a liquid diluent, for example, water, glycols, alcohols or y-butyrolactone among many other liquid diluents. The weight percentage of active ingredient ranges from 1 to 50 percent, and the weight percentage of diluent ranges from 40 to 99 percent, for Oil Dispersions, Suspensions, Emulsions, Solutions, including Emulsifiable Concentrates.

[0007] The document W02010 / 046430 A2 discloses a method for controlling pests and / or increasing the plant health that comprises the application of a pesticide wherein the pesticide is selected from a long list of active ingredients, and hexazinone is one of the active ingredients in said list. This document also mentions that the agrochemical composition may comprise customary auxiliary compounds, such as for example, solvents. Suitable solvents are water, organic solvents such as mineral oil fractions of medium to high boiling point, alcohols, fatty acids and esters, or amines. The compound y-butyrolactone is listed as suitable solvent for this composition. This document also provides a general description for water soluble concentrates (SL or LS type

[0008] 100229193.2compositions), 10 parts of active ingredient are dissolved in 90 parts by weight of water or in a water-soluble solvent.

[0009] SUMMARY OF THE INVENTION

[0010] It is an endeavor of the present invention to find liquid compositions that contain hexazinone which are stable compositions.

[0011] A first aspect is a liquid composition that consists of one active ingredient which is hexazinone and comprises at least one agriculturally acceptable carrier selected from the group of y- or 6-lactones in a range of 10 to 35% by total weight of the composition.

[0012] A second aspect of the invention is directed to a tank mix comprising an adjuvant and a liquid composition that consists of one active ingredient which is hexazinone and comprises at least one agriculturally acceptable carrier selected from the group of y- or 6-lactones in a range of 10 to 35% by total weight of the composition.

[0013] A third aspect of the invention is a method for the control of weeds comprising contacting an effective amount of a liquid composition that consists of one active ingredient which is hexazinone and comprises at least one agriculturally acceptable carrier selected from the group of y- or 6-lactones in a range of 10 to 35% by total weight of the composition; or contacting an effective amount of the tank mix comprising an adjuvant and the hereinabove defined liquid composition, with at least one of a locus where the weed is to be controlled, a plant or tree, an area adjacent to a plant or tree, soil adapted to support growth of a plant or tree, a root of a plant or tree, foliage of a plant or tree, and / or a seed adapted to produce a plant or tree.

[0014] DETAILED DESCRIPTION OF THE INVENTION

[0015] Definitions

[0016] Embodiments of the present invention are discussed in detail below. In describing embodiments, specific terminology is employed for the sake of clarity. However, the invention is not intended to be limited to the specific terminology so selected. While specific exemplary embodiments are discussed, it should be understood that this is done for illustration purposes only. A person skilled in the relevant art will recognize that other components and configurations can be used without parting from the spirit and scope of the invention. While a number of embodiments and features are described herein, it is to be understood that the various features of the invention and aspects of embodiments, even if described separately, may be combined

[0017] 2

[0018] 100229193.2unless mutually exclusive or contrary to the specific description. All references cited herein are incorporated by reference as if each had been individually incorporated.

[0019] As used herein, the transitional term "comprising" or "that comprises", which is synonymous with "including," or "containing," is inclusive or open-ended and does not exclude additional, un-recited elements or method steps. However, in each recitation of "comprising" herein, it is intended that the term also encompass, as alternative embodiments, the phrases "consisting essentially of" and "consisting of", where "consisting of" excludes any element or step not specified and "consisting essentially of" permits the inclusion of additional un-recited elements or steps that do not materially affect the essential or basic and novel characteristics of the composition or method under consideration.

[0020] Prior to setting forth the present subject matter in detail, it may be helpful to provide definitions of certain terms to be used herein. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as is commonly understood by one of skill in the art to which this subject matter pertains.

[0021] As used herein, the terms "stable" or "stability" when used in connection with the chemical stability of the liquid composition means that the decomposition of hexazinone in the liquid composition of the invention is less than 20% by weight of hexazinone, when the liquid composition is kept at 54-C for 2 weeks.

[0022] As used herein, the term "effective amount" when used in connection with the hexazinone active ingredient or the liquid composition or the tank mix containing hexazinone, refers to an amount of hexazinone that, when ingested, contacted with or sensed, is sufficient to achieve a good level of control of a weed.

[0023] An "active ingredient" is a substance capable of controlling undesired plants (weeds), plant pests or plant diseases, and does not cause significant damage to the treated plants or trees. The term "active ingredient" comprises, but is not limited to insecticides, nematicides, herbicides, fungicides, algicides, animal repellents or acaricides. Active ingredients are not limited to pesticides, and also include for example hormones, bio-stimulants, and plant growth regulators. As used herein, the term "herbicide" refers to an active ingredient capable of controlling unwanted plants or weeds, for example when growing in the locus of the desired plants or trees. As used herein, the term "agriculturally acceptable carrier" means a carrier which is known and accepted in the art for the formation of compositions for agricultural or horticultural use.

[0024] 3

[0025] 100229193.2As used herein the term "plant" or "tree" includes reference to whole plants, plant organs (e.g. leaves, stems, twigs, roots, trunks, limbs, shoots, fruits etc.), plant cells, or plant seeds, which have industrial interest, including grasslands and pastures, such as for example plants destined to animal consumption or other industrial uses. The term "plant" or "tree" may also include the propagation material thereof, which may include all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers, which can be used for the multiplication of the plant or tree. It may also include spores, corms, bulbs, rhizomes, sprouts basal shoots, stolons, and buds and other parts of plants or tree, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.

[0026] As used herein, the term "locus" includes a habitat, breeding ground, plant, tree, seed adapted to produce a plant or tree, propagation material, soil, field, area adjacent to a plant or tree, material or environment in which a weed is growing or may grow.

[0027] As used herein, the terms "control" or "controlling" or "combatting" refers to preventing the growth of weeds, delaying the onset of weeds, and to killing or to reducing growth of weeds. The liquid composition (or the tank mix thereof) may additionally comprise agriculturally acceptable inert additives. These additives are defined herein as any substance that itself is not an active ingredient but is added to the composition to improve its properties. Some substances can be used as agriculturally acceptable inert additives in the liquid composition of the invention or mixed as tank additives with the liquid composition of the invention prior to application in the field. Non-limiting examples of agriculturally acceptable inert additives and of tank adjuvants are chelating agents, thickeners, anti-foam agents, pH buffers, antifreeze agents, surfactants, dispersants, emulsifiers, wetting agents or humectants, suspending agents, stabilizers, plant penetrants (or translocators), anti-oxidation agents, preservative agents, drift retardants, inverting agents, soil penetrants, UV absorbers, binders, stickers, fertilizers, pigments, colorants or solvents.

[0028] As used herein, the term "adjuvant" is broadly defined as any substance that itself is not an active ingredient, but which enhances or is intended to enhance the effectiveness of the herbicide with which it is used. Adjuvants may be understood to include, but are not limited to, safeners, spreading agents, plant penetrants (or translocators), compatibility agents, drift retardants, soil penetrants, stickers, fertilizers. They are typically used to dilute ready mix formulations prior to application in the field, although some formulations include built-in adjuvants.

[0029] 4

[0030] 100229193.2As used herein, the term "tank mix" refers to the mixture of two or more active ingredients or compositions that are mixed shortly before application. Tank mixtures can therefore be formed by mixing one or more compositions (each comprising one or more active ingredients) with water and / or with one or more adjuvants, or they can be formed by mixing the active ingredients in situ with water and / or with one or more adjuvants.

[0031] The term "a" or "an" as used herein includes the singular and the plural, unless specifically stated otherwise. Therefore, the terms "a," "an" or "at least one" can be used interchangeably in this application.

[0032] 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).

[0033] Unless otherwise specified, references to percentages of a component present in a combination are by weight (wt.) percentages of the component with respect to the total weight of the combination.

[0034] It is further understood that where a parameter range is provided, all integers within that range, and tenths thereof, are also provided by the subject matter. For example, "0.1% to 50%" includes 0.1 %, 0.2 %, 0.3 %, 0.4 % etc. up to 50 %.

[0035] When a ratio herein is to be "X:l or higher", it is meant that the ratio is Y:l, where Y is X or greater, and when a ratio is herein to be "X:l or lower", it is meant that the ratio is Z:l, where Z is X or less. The same logic follows for ratios that are "1:X or higher" and "1:X or lower".

[0036] For purposes of better understanding the present teachings and in no way limiting the scope of the teachings, unless otherwise indicated, all numbers expressing quantities, percentages or proportions, and other numerical values used in the specification and claims, are to be understood as being modified in all instances by the term "about." Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained. At the very least, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques. In this regard, used of the term "about" herein specifically includes ±10% from the indicated values in the range. In addition, the endpoints of all ranges directed to the same component or property herein are inclusive of the endpoints, are independently combinable, and include all intermediate points and ranges. Similarly, the ranges and amounts for each element of the

[0037] 5

[0038] 100229193.2technology described herein can be used together with ranges or amounts for any of the other elements.

[0039] Liquid composition

[0040] The present disclosure relates to a liquid composition that consists of one active ingredient which is hexazinone and comprises at least one agriculturally acceptable carrier selected from the group of y- or 6-lactones in a range of 10 to 35% by total weight of the composition.

[0041] This liquid composition provides an alternative to the existing compositions of hexazinone and particularly, it provides a stable composition, i.e. the decomposition of hexazinone in the liquid composition is less than 20% by weight of hexazinone, when the liquid composition is kept at 54-C for 2 weeks.

[0042] The y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, P-methyl-y-octalactone, 6-valerolactone, 6-caprolactone, or 6-nonalactone. The y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, or -methyl-y-octalactone. The y- or 6-lactone may be y-butyrolactone.

[0043] The amount of the y- or 6-lactone in the liquid composition may range from 10% to 30% by total weight of the composition. The amount of the y- or 6-lactone in the liquid composition may range from 12% to 27% by total weight of the composition. The amount of the y- or 6-lactone in the liquid composition may range from 15% to 25% by total weight of the composition.

[0044] The y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, P-methyl-y-octalactone, 6-valerolactone, 6-caprolactone, or 6-nonalactone, and the amount of the y- or 6-lactone in the liquid composition may range from 10% to 30% by total weight of the composition. The y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, or P-methyl-y-octalactone, and the amount of the y- or 6-lactone in the liquid composition may range from 12% to 27% by total weight of the composition. The y-or 6-lactone may be y-butyrolactone, and the amount of the y- or 6-lactone in the liquid composition may range from 15% to 25% by total weight of the composition.

[0045] 6

[0046] 100229193.2The amount of hexazinone in the liquid composition may range from 12% to 45% by total weight of the composition. The amount of hexazinone in the liquid composition may range from 15% to 35% by total weight of the composition. The amount of hexazinone in the liquid composition may range from 18% to 30% by total weight of the composition.

[0047] The amount of hexazinone in the liquid composition may range from 12% to 45% by total weight of the composition, and the amount of the y- or 6-lactone may range from 10% to 30% by total weight of the composition. The amount of hexazinone in the liquid composition may range from 15% to 35% by total weight of the composition, and the amount of the y- or 6-lactone may range from 12% to 27% by total weight of the composition. The amount of hexazinone in the liquid composition may range from 18% to 30% by total weight of the composition, and the amount of the y- or 6-lactone may range from 15% to 25% by total weight of the composition.

[0048] The amount of hexazinone in the liquid composition may range from 12% to 45% by total weight of the composition, the y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, P-methyl-y-octalactone, 6-valerolactone, 6-caprolactone, or 6-nonalactone, and the amount of the y- or 6-lactone may range from 10% to 30% by total weight of the composition. The amount of hexazinone in the liquid composition may range from 15% to 35% by total weight of the composition, the y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, or P-methyl-y-octalactone, and the amount of the y-or 6-lactone may range from 12% to 27% by total weight of the composition. The amount of hexazinone in the liquid composition may range from 18% to 30% by total weight of the composition, the y- or 6-lactone may be y-butyrolactone, and the amount of the y- or 6-lactone may range from 15% to 25% by total weight of the composition.

[0049] The liquid composition of the invention may optionally further contain one or more agriculturally acceptable carriers selected from glycols, alcohols, ethers, carboxylic acid esters, or carbonate esters. The optionally further one or more agriculturally acceptable carrier may be selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, n-propanol, n-butanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, diglyme, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, diisopropyl carbonate, dibutyl carbonate, dioctyl carbonate, divinyl carbonate, diallyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate. The optionally further one or more

[0050] 7

[0051] 100229193.2agriculturally acceptable carrier may be selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate.

[0052] The amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 78%, from 0% to 70%, from 0% to 65% by total weight of the composition.

[0053] The amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 78% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from glycols, alcohols, ethers, carboxylic acid esters, or carbonate esters. The amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 70% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, n-propanol, n-butanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, diglyme, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, diisopropyl carbonate, dibutyl carbonate, dioctyl carbonate, divinyl carbonate, diallyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate. The amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 65% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate. The amount of hexazinone in the liquid composition may range from 12% to 45% by total weight of the composition, the y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, P-methyl-y-octalactone, 6-valerolactone, 6-caprolactone, or 6-nonalactone, the amount of the y- or 6-lactone may range from 10% to 30% by total weight of the composition, the amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 78% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from glycols, alcohols, ethers, carboxylic acid esters, or carbonate esters. The amount of hexazinone in the liquid composition may range from 15%

[0054] 8

[0055] 100229193.2to 35% by total weight of the composition, the y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, or P-methyl-y-octalactone, the amount of the y- or 6-lactone may range from 12% to 27% by total weight of the composition, the amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 70% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, n-propanol, n-butanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, diglyme, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, diisopropyl carbonate, dibutyl carbonate, dioctyl carbonate, divinyl carbonate, diallyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate. The amount of hexazinone in the liquid composition may range from 18% to 30% by total weight of the composition, the y- or 6-lactone may be y-butyrolactone, the amount of the y- or 6-lactone may range from 15% to 25% by total weight of the composition, the amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 65% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate.

[0056] The liquid composition of the invention may optionally further contain water. The amount of water in the liquid composition may range from 0% to 50%, from 0% to 40%, from 0% to 35% by total weight of the composition.

[0057] The amount of hexazinone in the liquid composition may range from 12% to 45% by total weight of the composition, the y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, P-methyl-y-octalactone, 6-valerolactone, 6-caprolactone, or 6-nonalactone, the amount of the y- or 6-lactone may range from 10% to 30% by total weight of the composition, the amount of water may range from 0% to 50% by total weight of the composition, the amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 78% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from glycols, alcohols, ethers, carboxylic acid esters, or carbonate esters. The amount of hexazinone in the liquid composition may range from 15%

[0058] 9

[0059] 100229193.2to 35% by total weight of the composition, the y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, or P-methyl-y-octalactone, the amount of the y- or 6-lactone may range from 12% to 27% by total weight of the composition, the amount of water may range from 0% to 40% by total weight of the composition, the amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 70% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, n-propanol, n-butanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, diglyme, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, diisopropyl carbonate, dibutyl carbonate, dioctyl carbonate, divinyl carbonate, diallyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate. The amount of hexazinone in the liquid composition may range from 18% to 30% by total weight of the composition, the y- or 6-lactone may be y-butyrolactone, the amount of the y- or 6-lactone may range from 15% to 25% by total weight of the composition, the amount of water may range from 0% to 35% by total weight of the composition, the amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 65% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate.

[0060] The liquid composition of the invention may be a homogeneous liquid formulation. The liquid composition of the invention may be a homogeneous liquid composition selected from the group consisting of Emulsifiable concentrate (EC), Oil miscible liquid (OL), Soluble concentrate (SL), Micro-emulsion (ME), Solution for seed treatment (LS), or Ultra-low volume liquid (UL). The liquid composition of the invention may be a Soluble concentrate (SL).

[0061] The liquid composition of the invention may be a homogeneous liquid composition, the amount of hexazinone in the liquid composition may range from 12% to 45% by total weight of the composition, the y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, P-methyl-y-octalactone, 6-valerolactone, 6-caprolactone, or 6-nonalactone, the amount of the y- or 6-lactone may range from 10% to 30% by total weight of the composition,

[0062] 10

[0063] 100229193.2the amount of water may range from 0% to 50% by total weight of the composition, the amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 78% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from glycols, alcohols, ethers, carboxylic acid esters, or carbonate esters. The liquid composition of the invention may be a homogeneous liquid composition selected from the group consisting of Emulsifiable concentrate (EC), Oil miscible liquid (OL), Soluble concentrate (SL), Micro-emulsion (ME), Solution for seed treatment (LS), or Ultra-low volume liquid (UL), the amount of hexazinone in the liquid composition may range from 15% to 35% by total weight of the composition, the y- or 6-lactone may be selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, or P-methyl-y-octalactone, the amount of the y- or 6-lactone may range from 12% to 27% by total weight of the composition, the amount of water may range from 0% to 40% by total weight of the composition, the amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 70% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, n-propanol, n-butanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, diglyme, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, diisopropyl carbonate, dibutyl carbonate, dioctyl carbonate, divinyl carbonate, diallyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate. The liquid composition of the invention may be a Soluble concentrate (SL), the amount of hexazinone in the liquid composition may range from 18% to 30% by total weight of the composition, the y- or 6-lactone may be y-butyrolactone, the amount of the y- or 6-lactone may range from 15% to 25% by total weight of the composition, the amount of water may range from 0% to 35% by total weight of the composition, the amount of the optionally further one or more agriculturally acceptable carrier may range from 0% to 65% by total weight of the composition, and it may be one or more agriculturally acceptable carriers selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate.

[0064] The pH of the liquid composition may range from 4 to 10, from 5 to 8.

[0065] 11

[0066] 100229193.2The viscosity of the liquid composition may range from 0.1 to 2500 centipoise (cps), from 1 to 500 cps, when it is measured with a Brookfield DV2T viscosimeter at room temperature. The liquid composition of the invention may optionally further contain one or more agriculturally acceptable inert additives. The agriculturally acceptable inert additive may be selected from the group consisting of chelating agents, thickeners, anti-foam agents, pH buffers, antifreeze agents, surfactants, dispersants, emulsifiers, wetting agents or humectants, suspending agents, stabilizers, plant penetrants (or translocators), anti-oxidation agents, preservative agents, drift retardants, inverting agents, soil penetrants, UV absorbers, binders, stickers, fertilizers, pigments, colorants, solvents or mixtures thereof.

[0067] Tank mix

[0068] The present disclosure also relates to a tank mix comprising an adjuvant and a liquid composition that consists of one active ingredient which is hexazinone and comprises at least one agriculturally acceptable carrier selected from the group of y- or 6-lactones in a range of 10 to 35% by total weight of the composition.

[0069] The liquid composition of the invention may be mixed with tank adjuvants, to yield a tank mix, prior to their application in the field to improve physical properties and efficacy. The tank adjuvants can be the same type of additives as the agriculturally acceptable inert additives added into the liquid composition, i.e. they may be selected from the group consisting of chelating agents, thickeners, anti-foam agents, pH buffers, antifreeze agents, surfactants, dispersants, emulsifiers, wetting agents or humectants, suspending agents, stabilizers, safeners, spreading agents, plant penetrants (or translocators), compatibility agents, anti-oxidation agents, preservative agents, drift retardants, inverting agents, soil penetrants, UV absorbers, binders, stickers, fertilizers, pigments, colorants, solvents or mixtures thereof. In one embodiment, the tank mix may comprise at least fertilizers.

[0070] Methods and Applications

[0071] The present document also discloses a method for the control of weeds comprising contacting an effective amount of a liquid composition that consists of one active ingredient which is hexazinone and comprises at least one agriculturally acceptable carrier selected from the group of y- or 6-lactones in a range of 10 to 35% by total weight of the composition; or contacting an effective amount of the tank mix comprising an adjuvant and the hereinabove defined liquid composition, with at least one of a locus where the weed is to be controlled, a plant or tree, an

[0072] 12

[0073] 100229193.2area adjacent to a plant or tree, soil adapted to support growth of a plant or tree, a root of a plant or tree, foliage of a plant or tree, and / or a seed adapted to produce a plant or tree. The methods disclosed in the present document refer to any weed for which hexazinone has known activity. The methods disclosed in the present document refer to any plants, trees or areas, including but not limited to natural rubber plants or trees; ornamental plants or trees (such as flowers, shrubs, broad-leaved trees, evergreens, conifers, tulip poplar); turfgrass, Bermuda grass or bahiagrass; forestry (conifers such as pines, firs or spruces); rangelands or pasture areas. The method disclosed in the present document may refer to ornamental plants or trees, forestry, rangelands or pasture areas.

[0074] The liquid compositions disclosed in the present document, whether neat or as tank mixes, are applied to the field in different amounts depending on the specific active ingredients used in the tank mixes, the targeted method and the weed to be controlled. In some embodiments, hexazinone is applied in an amount from 280 g / ha to 9.0 kg / ha, or from 500 g / ha to 5.6 kg / ha, per year.

[0075] The liquid compositions disclosed in the present document can be applied before planting, at the time of planting or after planting the plant or tree.

[0076] The following examples are included for illustrative purposes only and should not be construed as limitations on the invention claimed herein.

[0077] Examples

[0078] Example 1: Preparation of a liquid composition that consists of hexazinone, propylene glycol, water and y-butyrolactone

[0079] Propylene glycol (propane-1, 2-diol), y-butyrolactone and water are added to a reactor. Hexazinone is gradually added while stirring, until it is completely dissolved and a clear solution is obtained. Table 1 shows the amount of each ingredient in the composition.

[0080]

[0081] Table 1

[0082] 13

[0083] 100229193.2Example 2: Comparative formulations

[0084] Comparative compositions to Example 1 are prepared by replacing y-butyrolactone with the same amounts by weight of propylene glycol methyl ether (comparative composition 1), triethyl citrate (comparative composition 2), N-methyl pyrrolidone (comparative composition 3), N-butyl pyrrolidone (comparative composition 4), or by adding more propylene glycol (comparative composition 5).

[0085] Example 3: Stability of the compositions of Examples 1 and 2

[0086] Composition of Example 1 and comparative compositions are stored for 2 weeks at 54-C. Afterwards, the concentration of hexazinone is measured by HPLC (Thermo Scientific Ulti-Mate 3000 system with UV / PDA detector; column Gemini C18, 5pm, 250x4.6mm, 110 A, Phenomenex; flow rate 1.0 ml / min, solution A: 1 ml of H3PO per 1 L of water, solution B: acetonitrile) in order to calculate the decomposition of hexazinone during the storage. Table 2 shows the concentration of hexazinone and the percentage of hexazinone decomposition.

[0087]

[0088] Table 2

[0089] It is observed that when the liquid composition contains y-butyrolactone, the percentage of hexazinone decomposition is lower than 20% after 2 weeks at 54-C, and therefore, the composition of Example 1 is stable. In opposition, liquid comparative compositions that do not contain y-butyrolactone, are not stable when stored for 2 weeks at 54-C.

[0090] 14

[0091] 100229193.2Example 4: Liquid compositions that consist of hexazinone, propylene glycol and y-butyrolactone

[0092] The following compositions are prepared with the percentages by weight of Table 3:

[0093]

[0094] Table 3

[0095] Example 5: Stability of the Compositions 6 to 11

[0096] The stability of the Compositions 6 to 11 is checked by measuring the hexazinone decomposition after storage for 2 weeks at 54-C, as done in Example 3. The percentages of hexazinone decomposition are shown in Table 4:

[0097]

[0098] Table 4

[0099] It is observed that when the amount of y-butyrolactone is lower than 10 % by weight, then, the composition is not stable, as for Compositions 6 and 7.

[0100] 15

[0101] 100229193.2

Claims

CLAIMS1. A liquid composition that consists of one active ingredient which is hexazinone and comprises at least one agriculturally acceptable carrier selected from the group of y- or 6-lactones in a range of 10 to 35% by total weight of the composition.

2. The liquid composition according to claim 1, wherein the y- or 6-lactone is selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, -methyl-y-octalactone, 6-valerolactone, 6-caprolactone, or 6-nonalactone.

3. The liquid composition according to any of previous claims, wherein the y- or 6-lactone is selected from the group consisting of y-butyrolactone, y-valerolactone, y-octalactone, y-nonalactone, y-decalactone, y-undecalactone, a-methyl-y-butyrolactone, or P-methyl-y-octalactone.

4. The liquid composition according to any of previous claims, wherein the amount of hexazinone ranges from 12% to 45% by total weight of the composition.

5. The liquid composition according to any of previous claims, which optionally further contains one or more agriculturally acceptable carriers selected from glycols, alcohols, ethers, carboxylic acid esters, or carbonate esters.

6. The liquid composition according to claim 5, wherein the optionally further one or more agriculturally acceptable carrier is selected from ethylene glycol, propylene glycol, dipropylene glycol, ethanol, methanol, isopropanol, n-propanol, n-butanol, tert-butanol, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1-4-dioxane, diglyme, ethyl acetate, isopropyl acetate, butyl acetate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, diisopropyl carbonate, dibutyl carbonate, dioctyl carbonate, divinyl carbonate, diallyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate, or 1,2-butylene carbonate.

7. The liquid composition according to any of claims 5 to 6, wherein the amount of the optionally further one or more agriculturally acceptable carrier ranges from 0% to 78%.

8. The liquid composition according to any of previous claims, wherein optionally further contains water.

9. The liquid composition according to claim 8, wherein the amount of optional water in the liquid composition ranges from 0% to 50% by total weight of the composition.16100229193.

210. The liquid composition according to any of previous claims, which is homogeneous.

11. The liquid composition according to any of previous claims, which is a homogeneous liquid composition selected from the group consisting of Emulsifiable concentrate (EC), Oil miscible liquid (OL), Soluble concentrate (SL), Micro-emulsion (ME), Solution for seed treatment (LS), or Ultra-low volume liquid (UL) compositions.

12. A tank mix comprising an adjuvant and a liquid composition that consists of one active ingredient which is hexazinone and comprises at least one agriculturally acceptable carrier selected from the group of y- or 6-lactones in a range of 10 to 35% by total weight of the composition.

13. A method for the control of weeds comprising contacting an effective amount of the liquid composition according to any of claims 1 to 11 or the tank mix according to claim 12 with at least one of a locus where the weed is to be controlled, a plant or tree, an area adjacent to a plant or tree, soil adapted to support growth of a plant or tree, a root of a plant or tree, foliage of a plant or tree, and / or a seed adapted to produce a plant or tree.

14. The method according to claim 13, which is applied in a plant, tree or area selected from the group consisting of natural rubber plants or trees, ornamental plants and trees, turfgrass, Bermuda grass, bahiagrass, forestry, rangelands or pasture areas.

15. The method according to any of claims 13 to 14, wherein hexazinone is applied in an amount from 280 g / ha to 9.0 kg / ha per year.

16. The liquid composition according to any of claims 1 to 11, wherein the amount of hexazinone in the liquid composition ranges from 18% to 30% by total weight of the composition, the y- or 6-lactone is y-butyrolactone, and the amount of the y- or 6-lactone ranges from 15% to 25% by total weight of the composition.17100229193.2

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