Enhancing tolerance of wheat to hydroxyphenylpyruvate dioxygenase-inhibiting herbicides with cloquintocet-mexyl or mefenpyr-diethyl

Abstract

Disclosed herein is the use of cloquintocet-mexyl, mefenpyr-diethyl, or a combination thereof as a wheat safener against hydroxyphenyl pyruvate dioxygenase (HPPD)-inhibiting herbicides.

Description

[0001] ENHANCING TOLERANCE OF WHEAT TO HYDROXYPHENYLPYRUVATE DIOXYGENASE-INHIBITING HERBICIDES WITH CLOQUINTOCET-MEXYL OR MEFENPYR-DIETHYL

[0002] CROSS-REFERENCE TO RELATED APPLICATIONS The present application claims priority to U.S. Provisional Patent Application No.

[0003] 63 / 755,705, filed February 07, 2025, the entire content of which is hereby incorporated by reference.

[0004] BACKGROUND OF THE INVENTION

[0005] Wheat is a grass that is cultivated for its seed, a cereal grain that is a staple food worldwide. Given the importance of wheat as food crops, methods for improved cultivation of such crops are needed.

[0006] BRIEF SUMMARY OF THE INVENTION

[0007] Disclosed herein is a method of growing wheat comprising applying an effective amount of a safener to wheat seed prior to planting and applying an effective amount of a hydroxyphenylpyruvate dioxygenase (HPPD)-inhibiting herbicide to the planting area. The safener may be cloquintocet-mexyl, mefenpyr-diethyl, or a combination thereof. The herbicide may be a triketone, a pyrazolone, a pyrazole, an isoxazole, or an azole carboximide, such as mesotrione, tembotrione, topramezone, tolpyralate, isoxaflutole, or iptriazopyrid.

[0008] The method may include applying the herbicide at a greater than recommended amount. The method may provide weed control and the same or lower amount of injury, bleaching, necrosis, or a combination thereof as compared to a control plant. The method may also provide weed control and improved early season vigor as compared to a control plant.

[0009] BRIEF DESCRIPTION OF THE DRAWINGS

[0010] Non-limiting embodiments of the present invention will be described by way of example with reference to the accompanying figures, which are schematic and are not intended to be drawn to scale. In the figures, each identical or nearly identical component illustrated is typically represented by a single numeral. For purposes of clarity, not every component is labeled in everyfigure, nor is every component of each embodiment of the invention shown where illustration is not necessary to allow those of ordinary skill in the art to understand the invention.

[0011] Figure 1 shows photograph of wheat treated with mesotrione at 420 g ai / ha. The seed treatments from left to right include the no herbicide safener seed treatment, cloquintocet, and mefenpyr. Visually the furthest left two rows (no seed treatment) are injured by the herbicide mesotrione in the form of bleaching and reduced vigor whereas the wheat treated with the herbicide safeners are healthier.

[0012] Figure 2 illustrates wheat visual bleaching with the various treatments from Example 2. The asterisk indicates a significant difference in response compared to the other seed treatment (P-value < 0.05).

[0013] Figure 3 illustrates wheat visual injury with the various treatments from Example 2. The asterisk indicates a significant difference in response compared to the other seed treatment (P-value < 0.01).

[0014] Figure 4 shows wheat injury with mesotrione herbicide as influenced by different seed treatments.

[0015] Figure 5 is a bar graph illustrating percent wheat injury following mesotrione application at various time points after first application.

[0016] Figure 6 is a bar graph illustrating percent wheat bleaching following mesotrione application at various time points after first application.

[0017] Figure 7 is a bar graph illustrating percent wheat necrosis following mesotrione application.

[0018] Figure 8 is a bar graph illustrating wheat plants per meter row following mesotrione application.

[0019] Figure 9 is a bar graph illustrating wheat plants per meter row following application of various herbicides.

[0020] Figure 10 is a bar graph illustrating percent wheat injury at multiple time points following application of various herbicides.

[0021] Figure 11 is a bar graph illustrating percent wheat bleaching following application of various herbicides.

[0022] Figure 12 is a bar graph illustrating percent wheat necrosis following application of various herbicides.DETAILED DESCRIPTION OF THE INVENTION

[0023] Disclosed herein is the use of cloquintocet-mexyl and mefenpyr-diethyl as safeners. The Examples demonstrate that applying cloquintocet-mexyl and / or mefenpyr-diethyl to the seeds of wheat plants enhanced tolerance and reduced plant injury caused by hydroxyphenyl pyruvate dioxygenase (HPPD)-inhibiting herbicides. Specifically, in conjunction with the application of herbicides, wheat crops grown from cloquintocet-mexyl or mefenpyr-diethyl-treated seeds were shown to exhibit increased early-season vigor, decreased injury, decreased necrosis, and / or decreased bleaching as compared to control plants grown from seeds that were not treated with safeners. These effects may result in improved weed control and allow for greater amounts of herbicides to be used with the same or reduced injury when compared against herbicide application without cloquintocet-mexyl or mefenpyr-diethyl seed treatment. These effects may also allow herbicides to be registered and commercially employed that are not currently being applied, or mitigate carryover restrictions from the planting of wheat behind com treated with HPPD herbicides.

[0024] Methods of safening wheat:

[0025] One aspect of the present disclosure provides a method of growing wheat comprising applying an effective amount of a safener to wheat seed prior to planting and applying an effective amount of a hydroxyphenylpyruvate dioxygenase (HPPD)-inhibiting herbicide to the planting area. The safener may be cloquintocet-mexyl, mefenpyr-diethyl, or a combination thereof.

[0026] The term "herbicide" refers to substances used to control weeds. In some embodiments, the wheat is treated with one or more herbicides. Suitable herbicides include preplant, preemergence, and postemergence herbicides. Where an herbicide is referenced generically herein by name, unless otherwise restricted, that herbicide includes all commercially available forms such as salts, esters, free acids and free bases, as well as stereoisomers thereof. In some embodiments, the wheat is treated with one or more herbicides. Herbicides that are used in combination with the cloquintocet-mexyl and / or mefenpyr-diethyl seed treatment include, without limitation, Group 27 herbicides. Group 27 herbicides include hydroxyphenylpyruvate dioxygenase (HPPD)-inhibiting herbicides, such as triketones (e.g., mesotrione and tembotrione), pyrazolones (e.g., topramezone and tolpyralate), pyrazoles, isoxazoles (e.g., isoxaflutole), and azole carboximides (e.g., iptriazopyrid).Any herbicide formulation that is suitable for agricultural use may be used in the methods of the present invention. Suitable herbicide formulations include, without limitation, emulsifiable concentrates, soluble concentrates, and microencapsulated formulations.

[0027] “Emulsifiable concentrates” are oily liquid formulations that are prepared by dissolving an oil-soluble active ingredient in one or more organic solvents (e.g., benzene, toluene, xylene). Emulsifiable concentrates may additionally include surfactants or other additives. Prior to utilization, an emulsifiable concentrate is diluted in water to form an oil-in-water emulsion in which the active ingredient is in the organic phase.

[0028] “Suspension concentrates” are formulations that are prepared by dispersing a solid active ingredient in water. Suspension concentrates may additionally include surfactants or other additives. In some embodiments, the herbicide is applied as a suspension concentrate.

[0029] “Microencapsulated formulations” are formulations in which an active ingredient is contained within a porous shell (e.g., a polymer shell), which serves to protect the active ingredient from degradation. For a detailed description of microencapsulated formulations, see US Patent No.

[0030] 9,877,478, which is hereby incorporated by reference in its entirety. When exposed to soil moisture, the polymer shell dissolves, and the active ingredient is slowly released. Delayed release of the active ingredient gives the crop plant time to imbibe soil water and grow uninhibited before it is affected by the herbicide. In addition, gradual release allows the herbicide to provide longer residual control of weeds relative to non-microencapsulated formulations. In microencapsulated formulations, the release rate of the core material can be controlled through selection of several parameters, including: the shell composition, the core material composition, the weight ratio of the core material to shell material, the microcapsule particle size, and processing conditions such as mixing shear and time. In some formulations, a diluent, such as a solvent, may be added to change the solubility characteristics of the core material to alter the release rate. Any diluent may be used as long as it is compatible with the core material and the shell material. Microencapsulated formulations may comprise multiple populations of particles that each comprise a different core material composition. For example, a microencapsulated formulation may comprise particles with two different core material compositions in which the same active ingredient is mixed with two different solvents to provide a bimodal release rate. Additional ingredients may be added to the core material to improve its properties including, without limitation, thickeners, stabilizers, anti-packing agents, drift control agents, biocides, preservatives, antifreeze agents, and antifoam agents.

[0031] The herbicides may be applied either prior to or after the wheat is planted. In some embodiments, the herbicide is applied after planting, and the application may be either preemergence or postemergence. “Preemergence” refers to anytime during the interval from the planting of a crop plant up to, but not including, emergence of the crop plant (z.e., before cracking or spiking). Thus, the herbicide may also be applied delayed preemergence. "Delayed preemergence" generally refers to the time after germination but before emergence of the seedlings. Preemergence treatment includes both the treatment of the crop area before sowing (i.e., preplant incorporation), and the treatment of the sown crop areas in which the plants have not yet emerged. Postemergence treatments include early postemergence (EPOST) application, as well as application at the spiking, one- to two-leaf, or three- to four-leaf stage. In some embodiments, the herbicide application is preemergence.

[0032] The effective amount of herbicide to be applied to an agricultural field is dependent upon the identity of the herbicide, the release rate of the herbicide, the crop to be treated, and environmental conditions, especially soil type and moisture. Generally, application rates of herbicides, such as, for example, a Group 27 herbicide, are on the order of about 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.11, 0.12, 0.13, 0.14, 0.15, 0.16, 0.17, 0.18, 0.19, 0.2, 0.5, 1, 2, 3, 4 or 5 kilograms of herbicide per hectare, or ranges thereof, such as from 0.01 to 5 kilograms per hectare, 0.01 to 4 kilograms per hectare, 0.01 to 3 kilograms per hectare, 0.01 to 2 kilograms per hectare, 0.01 to 1 kilograms per hectare, 0.01 to 0.5 kilograms per hectare, 0.01 to 0.4 kilograms per hectare, 0.01 to 0.3 kilograms per hectare, 0.01 to 0.2 kilograms per hectare, 0.01 to 0.1 kilograms per hectare, 0.02 to 5 kilograms per hectare, 0.02 to 4 kilograms per hectare, 0.02 to 3 kilograms per hectare, 0.02 to 2 kilograms per hectare, 0.02 to 1 kilograms per hectare, 0.02 to 0.5 kilograms per hectare, 0.02 to 0.4 kilograms per hectare, 0.02 to 0.3 kilograms per hectare, 0.02 to 0.2 kilograms per hectare, 0.02 to 0.1 kilograms per hectare, 0.03 to 5 kilograms per hectare, 0.03 to 4 kilograms per hectare, 0.03 to 3 kilograms per hectare, 0.03 to 2 kilograms per hectare, 0.03 to 1 kilograms per hectare, 0.03 to 0.5 kilograms per hectare, 0.03 to 0.4 kilograms per hectare, 0.03 to 0.3 kilograms per hectare, 0.03 to 0.2 kilograms per hectare, or from 0.03 to 0.1 kilograms per hectare.In some embodiments, herbicide may be applied to the wheat plant or seed at an amount that is less than recommended. The recommended amount of herbicide may be the amount of herbicide recommended for application to the crop plant according to the herbicide's label. The reduction in applied amount of herbicide may be at least 10%, 20%, 30%, 40%, or 50% or between 10 - 90%, 20 - 90%, 30 - 90% 40 - 90% or 50 - 90% to achieve a commercially acceptable rate of weed control.

[0033] In some embodiments, herbicides may be applied to the wheat plant or seed at an amount that is greater than recommended. This is accomplished by increasing the plants tolerance to the herbicide. The recommended amount of herbicide may be the amount of herbicide recommended for application to the crop plant according to the herbicide's label. The increase in applied amount of herbicide may be the amount of herbicide, that in combination with the use of the safener, results in the same or lower amount of injury, necrosis, or bleaching as the control plant. The herbicide may be applied to the crop plant or seed at 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 100%, more than 100%, more than 200%, more than 300%, or more than 400% more than recommended amount to achieve a commercial acceptable rate of weed control. The herbicide may be applied to the crop plant or seed at between 10 - 200%, 20 - 190%, 30 - 180%, 40 - 170%, 50 -160%, 60 - 150%, 70 - 140%, 80 - 130%, or 90 - 120% more than recommended amount to achieve a commercial acceptable rate of weed control.

[0034] In some embodiments, the effective amount of the herbicide is an amount of the herbicide that results in commercially acceptable rate of weed control. In some embodiments, the effective amount of herbicide is an amount of herbicide, that in combination with the use of the safener, results in weed control and the same or lower amount of injury, bleaching, necrosis, or a combination thereof, as compared to a control plant. In some embodiments, the effective amount of herbicide is an amount of herbicide, that in combination with the use of the safener, results in weed control and improved early season vigor as compared to a control plant. For example, the effective amount of herbicide may be an amount of herbicide, that in combination with the use of the safener, results in weed control and improved wheat density, wheat biomass, or combination thereof, as compared to a control plant.

[0035] The methods may be applied in combination with additional herbicides. Applying several herbicides with distinct mechanisms of action may be useful, for example, for treating fields with herbicide-resistant weeds such as barnyardgrass. Exemplary co-herbicides include, withoutlimitation, ACCase inhibitors (e.g., aryloxyphenoxypropionics), enolpyruvyl shikimate-3-phosphate synthaste (EPSPS) inhibitors (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate), synthetic auxins (e.g., aromatic acid, phenoxy and pyridine herbicides), photosystem II (PS II) inhibitors (e.g., ureas and triazines), ALS or AHAS inhibitors (e.g., sulfonylureas, triazol opyrimidines and imidazolinones), photosystem I (PS I) inhibitors (e.g., paraquat), protoporphyrinogen oxidase (PPO) inhibitors (e.g., diphenyl ethers, phenyl pyrazoles, aryl triazones and oxadiazoles), mitosis inhibitors (e.g., anilide, amide, certain organophosphorus and carbanilate herbicides), cellulose inhibitors (e.g., nitrile and oxazole herbicides), oxidative phosphorylation uncouplers, dihydropteroate synthase inhibitors, fatty acid and lipid biosynthesis inhibitors (e.g, thiocarbamate and certain organophosphorus herbicides), auxin transport inhibitors (e.g, amide and urea herbicides) and carotenoid biosynthesis inhibitors (e.g, isoxazolidinone, benzoylcyclohexanedione and benzoylpyrazole herbicides), salts and esters thereof, and mixtures thereof. In some embodiment, the method may comprise applying an additional herbicide, such as a Group 2 herbicide (e.g., thiencarbazone-methyl).

[0036] As used herein, the word "safener" is used to refer to compounds that antagonize the harmful effects of an herbicide on cultivated plants. Safeners were formerly referred to as "antidotes", and these terms may be used interchangeably. Preferably, these compounds protect cultivated plants without noticeably influencing the herbicide's action on the weeds that it is meant to control. The methods of the present invention may utilize any safener that protects wheat plants against injury from an HPPD-inhibiting herbicide. In some embodiments, the safener is cloquintocet-mexyl, mefenpyr-diethyl, or a combination thereof, including all available forms such as salts, esters, free acids and free bases, as well as stereoisomers thereof.

[0037] Safeners are most effective when applied prior to or simultaneously with the herbicides whose injury they prevent. Depending on their properties, safeners can be used for pretreating the seeds of the cultivated plants (dressing seeds or seedlings), can be incorporated in the soil (e.g, in the furrow) before or after sowing seeds, or else applied alone or together with the herbicide (e.g., as a tank mixture) before or after emergence of the plants. Thus, treatment of the plant or seeds with the safener can be carried out independently of the time of application of the herbicide, or alternatively, the treatment can be carried out simultaneously. In some embodiments, the safener is applied to the seeds prior to planting (i.e., by coating the seeds with the safener). In some such embodiments, an optional second safener is applied to the planting area. The second safener maybe applied simultaneously with the herbicide. In some embodiments, the second safener comprises cloquintocet-mexyl, mefenpyr-diethyl, or a combination thereof.

[0038] The safener may be used in an unmodified form or as a composition with conventional adjuvants and carriers. Safeners may be formulated in any known manner, for example, as emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations in e.g. polymer substances. The compositions can also contain further ingredients such as stabilizers, antifoams, viscosity regulators, binders, adhesives, as well as fertilizers or other active compounds, in order to attain special effects.

[0039] The safener formulations are prepared in known manner, e.g. by mixing and / or grinding the active ingredients with extenders, e.g. solvents, solid carriers and, where appropriate, surfaceactive compounds (surfactants). Suitable safener solvents include without limitation: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted naphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane, or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether; ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethyl formamide; as well as epoxidised vegetable oils such as epoxidised coconut oil or soybean oil; or water. Suitable solid carriers used e.g. for dusts and dispersible powders are normally natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite. In order to improve the physical properties it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carriers are materials such as calcite or sand. In addition, a great number of pregranulated materials of inorganic or organic nature can be used, e.g. especially dolomite or pulverized plant residues. Depending on the nature of the safener to be formulated, suitable surface-active compounds are nonionic, cationic and / or anionic surfactants having good emulsifying, dispersing and wetting properties. The surfactants customarily employed in such formulations are described e.g. in the following publications: "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ringwood, N.J., 1979; Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co. Inc., New York, 1964.The rate of application in which the safener is applied in relation to the herbicide depend on the mode of application. When the safener is applied as a field treatment, either alone or as a tank mixture with the herbicide, the ratio of safener to herbicide is usually from 1 : 100 to 10:1, but more typically from 1:5 to 8:1. However, when safeners are applied as a seed dressing, smaller amounts per hectare of crop area are required than when they are applied later. For seed dressing, 0.1 to 10 g active ingredient of safener is usually required per kg of seeds. In some embodiments, the seed dressing comprises from 0.1 to 2 g, 0.1 to 3 g, 0.1 to 4 g, or 0.1 to 5 g per kg seed of the safener. In some embodiments, the seed dressing comprises at least 0.1 g, 0.5 g, 1.0 g, 1.5 g, 2.0 g, or 2.5 g per kg seed of the safener. In some embodiments, the safener may be cloquintocet-mexyl or mefenpyr-di ethyl. In some embodiments, the wheat seeds are treated with cloquintocet-mexyl or mefenpyr-diethyl at a rate of 0.5 g ai / kg-seed. In some embodiments, the wheat seeds are treated with cloquintocet-mexyl or mefenpyr-diethyl at a rate of 1.5 g ai / kg-seed. In some embodiments, the wheat seeds are treated with cloquintocet-mexyl at a rate of 0.5 g ai / kg-seed and mefenpyr-diethyl at a rate of 1.5 g ai / kg-seed.

[0040] In some embodiments, in addition to the seed treatment, an optional second safener is applied to the planting area. In some such embodiments, the second safener may comprise an effective amount of cloquintocet-mexyl, mefenpyr-diethyl, or a combination thereof. The second safener may be applied at a rate of from about 5 to about 50 fl oz / acre, about 5 to about 40 fl oz / acre, about 10 to about 40 fl oz / acre, about 10 to about 30 fl oz / acre, or about 10 to about 20 fl oz / acre.

[0041] The term “effective amount of a safener” refers to an amount of cloquintocet-mexyl, mefenpyr-diethyl, or a combination thereof, respectively, that provides the desired effect (e.g., wheat safening effects and improved early-season vigor such as decreased injury, decreased bleaching, decreased necrosis, decreased mortality rate, increased density, increased stand counts, increased wheat biomass, or any combination thereof), either following single or multiple applications. An effective amount can be determined by one skilled in the art using known techniques and by observing results obtained under analogous circumstances. In determining the effective amount of the safener to be applied to a seed, a number of factors can be considered, such as: the species or variety of the seed, the growing location, the time of planting, soil conditions, abiotic stresses, and the like. In some embodiments, an effective amount of the safener may be an amount that, when used with an effective amount of an agrochemical, allows for or improves theefficacy of the agrochemical as compared to the same amount of the agrochemical alone. In some embodiments, an effective amount of the safener may allow the herbicide to be applied to the wheat plant or seed at an amount that is greater than recommended.

[0042] Seed treatment with the safener can improve early season vigor or canopy formation. The term “early season vigor” refers to the ability of a plant to grow and thrive during the early season. The term “early season” refers to a period of less than 60 days after emergence (i.e., less than 60 days after a growing plant has emerged from the soil). In some contexts, early season refers to a period of less than 30, 35, 40, 45, 50, or 55 days after emergence. Suitably, early season may refer to a period from about 1-60, 10-55, 20-50, or 30-45 days after emergence.

[0043] The term “canopy formation” refers to the formation of the aboveground portion of a plant and is measured as a percentage of the ground area covered by the plant. Early season vigor or canopy formation can be assessed based on various parameters including, without limitation, plant injury, the number of alive plants, leaf area, plant density, plant height, dry matter accumulation, and various growth parameters.

[0044] In some embodiments, at 7-28 days after emergence, wheat plants grown from cloquintocet-mexyl and / or mefenpyr-diethyl-treated seeds have exhibited decreased mortality rates, decreased injury, decreased necrosis, decreased bleaching, increased density, increased stand counts, increased wheat biomass, or any combination thereof as compared to control plants. Thus, in some embodiments, the methods of the present invention decrease mortality rates, decrease injury, decrease necrosis, decrease bleaching, increase density, increase stand counts, increase wheat biomass, or any combination thereof of the wheat plant relative to a control plant. In some embodiments, the methods decreased mortality rates, decreased injury, decreased necrosis, decreased bleaching, increased density, increased stand counts, increased wheat biomass, or any combination thereof of the wheat plant by a statistically significant amount relative to the control plant.

[0045] As used herein, a “control plant” is a comparable plant (e.g., of the same species, variety, and age) that was grown under substantially similar conditions but was grown from a seed that was not treated with cloquintocet-mexyl and / or mefenpyr-diethyl. Plants that are grown in “substantially similar conditions” are grown in similar locations and soil conditions, are planted with similar timing, are subjected to similar abiotic stresses, and the like.When grown under substantially similar conditions, plants of the same variety are expected to exhibit statistically insignificant differences in the absence of a difference in treatment. The term “statistically significant” refers to an experimentally verifiable result that is not likely to occur randomly but is instead likely to be attributable to specific cause (e.g., the cloquintocet-mexyl and / or mefenpyr-diethyl seed treatment). In some embodiments, data were subjected to analysis of variance (ANOVA). A statistically significant result is one based on Fisher’s protected Least Significant Different (LSD) test at a = 0.05. In some embodiments, a statistically significant result is one based on Fisher’s protected Least Significant Different (LSD) test at a = 0.01. In some embodiments, a statistically significant result is one based on Fisher’s protected Least Significant Different (LSD) test at a = 0.1.

[0046] In some embodiments, the methods result in a statistically significant decrease in injury of the wheat plant. In some embodiments, the methods result in a statistically significant decrease in plant injury 7-28 days after treatment. In some embodiments, plant injury decreased by at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, or more than 95% after 7, 14, 21, 28, or more than 28 days after treatment as compared to a control plant. In some embodiments, the methods result in a statistically significant decrease in plant injury 7-28 days after emergence. In some embodiments, plant injury decreased by at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, or more than 95% after 7, 14, 21, 28, or more than 28 days after emergence as compared to a control plant.

[0047] The term “bleaching” refers to interference with pigment production and protection of chlorophyll, causing whitening of the plant. Some herbicides may cause chlorophyll to be destroyed. The absence of these pigments allows excessive light energy to destroy chlorophyll, which causes visible leaf bleaching. Plants are unable to photosynthesize due to a lack of pigments, and they may die after their energy reserves run out. Leaves turn white and may look bleached, and this symptom may be most severe near the leaf veins while interveinal areas may remain green. Purpling of leaf edges may also occur. Leaves that grow after application or exposure may look crinkled. In some embodiments, the methods result in a statistically significant decrease in bleaching of the wheat plant. In some embodiments, the methods result in a statistically significant decrease in bleaching 7-28 days after emergence. In some embodiments, bleaching decreased by at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, or more than 95% after 7, 14, 21, 28, or more than 28 days after emergence as compared to a control plant.The term “biomass” refers to the mass of a portion of plant material (i.e., both live and dead). Biomass may be calculated as dry weight or fresh weight. “Fresh weight” is determined by simply harvesting plant material and weighing it, whereas “dry weight” is determined by harvesting plant material, drying it in an oven, and then weighing it. For example, the plant material may be dried in an oven at 140-160°F (60-70°C) for 24-48 hours. In some embodiments, the methods result in a statistically significant increase in wheat biomass 7-28 days after emergence. In some embodiments, wheat biomass is increased by at least 5%, 10%, 20%, 30%, 40%, 50%, or more than 50% after 7, 14, 21, 28, or more than 28 days after emergence as compared to a control plant.

[0048] By enhancing wheat tolerance to herbicides and reducing plant injury, the methods of the present invention may improve weed control. A “weed” is a plant that is considered a nuisance to or a competitor of a commercially important crop plant. As used herein, the term “weed control” refers to any observable reduction in weed growth or vigor. Weed control can include (1) killing, (2) inhibiting growth, reproduction or proliferation, or (3) removing, destroying, or otherwise diminishing weeds. Weed control can be assessed visually. For example, weed control can be assessed by comparing the number or size of weeds surrounding treated plants to that of weeds surrounding untreated plants. Weed control may be defined, for instance, in terms of the number of weed plants or weight of the weeds that grow around treated plants as a percentage of the number or weight of the weeds that grow around untreated plants. A “commercially acceptable rate of weed control” varies with the weed species, degree of infestation, environmental conditions, and the associated crop plant. Commercially effective weed control may be defined as the destruction (or inhibition) of at least about 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, or even at least 85%, or even at least 90%. Although it is generally preferable from a commercial viewpoint that 70%-80% or more of the weeds be destroyed, commercially acceptable weed control can occur at much lower destruction or inhibition levels, particularly with some very noxious, herbicide-resistant plants.

[0049] Examples of weeds that may be controlled using the methods of the present invention include, but are not limited to, ryegrass, bamyardgrass (Echinochtoa crus-galli) and other weed species within the Echinochloa genus, crabgrasses within the genus Digitaria, Palmer amaranth (Amaranthus palmeri) and other weed species within the Amaranthus genus, common purslane (Portulaca oleracea) and other weed species in the Portulaca genus, Chenopodium album andother Chenopodium spp., Setaria lutescens and other Setaria spp., Solanum nigrum and other Solanum spp., Brachiaria platyphylla and other Brachiaria spp., Conyza canadensis and other Conyza spp., and Eleusine indica, mayweed chamomile Anthemis cotula) and other Anthemis spp., henbit (Lamium amplexicaule) and other Lamium spp., common chickweed (Stelaria media) and other Stelaria spp., and many other weeds in wheat including broadleaves, grasses, and / or lilies.

[0050] In some embodiments, the present invention compares the herbicide tolerance of wheat grown from a seed that was treated with an effective amount of the cloquintocet-mexyl and / or mefenpyr-diethyl to that of a control plant. The comparison comprises (a) growing the wheat plant and the control plant under substantially similar conditions; (b) measuring an indicator of tolerance to herbicides in both the wheat plant and the control plant; and (c) comparing the measurements obtained in (b).

[0051] Suitable indicators of tolerance to herbicides include, without limitation, mortality rates, plant injury, number of alive plants, necrosis, bleaching, plant density, stand counts, wheat biomass, plant height, dry matter accumulation, and various growth parameters. In some embodiments, the inventors demonstrate that wheat plants grown from the cloquintocet-mexyl or mefenpyr-diethyl-treated seeds have decreased mortality rates, decreased injury, decreased necrosis, decreased bleaching, increased density, increased stand counts, increased wheat biomass, or any combination thereof as compared to control plants. Thus, in some embodiments, the indicator of tolerance to herbicides is mortality rates, wheat injury, necrosis, bleaching, wheat density, wheat biomass, stand counts, or any combination thereof.

[0052] In some embodiments, the wheat seed may be additionally treated with one or more agrochemicals, such as an adjuvant, insecticide, fungicide, or plant growth regulator. Application of the cloquintocet-mexyl and / or mefenpyr-diethyl seed treatment may occur before, at the same time, or after the application of another agrochemical.

[0053] In some embodiments, all seeds, including seed that was not treated with cloquintocet-mexyl or mefenpyr-diethyl, were treated with a base treatment comprising a standard insecticide and fungicide. Thus, in some embodiments, the wheat seed is further treated with an insecticide and / or fungicide, or the methods further comprise treating seed of the wheat plant with an insecticide and / or fungicide. An “insecticide” is a chemical used to control insects by killing them or preventing them from engaging in undesirable or destructive behaviors. Examples of suitableinsecticides for use with the present invention include, without limitation, Nipslt® and CruiserMaxx®. A “fungicide” is a chemical used to kill or prevent the growth of fungi and their spores. Examples of suitable fungicides for use with the present invention include, without limitation, metalaxyl, fludioxonil, carboxin, and thiram.

[0054] A “growth regulator” is a chemical used to modify plant growth. Growth regulators can be used, for example, to increase branching, increase shoot growth, or alter fruit maturity. Growth regulators include both synthetic and naturally occurring substances.

[0055] A “adjuvant” is chemical or composition that enhances herbicidal activity by activating the herbicide or modifying the physical properties of the herbicide. Adjuvants can be used to improve spray coverage, provide uniform droplet size, reduce surface tension, slow drying, and / or increase the amount of material that penetrates the waxy outer layer of leaves, thereby increasing contact between the material to be absorbed and the surface membrane of the leaf. Suitable adjuvants include, for example, surfactants, wetting agents, spreaders, or stickers. In some embodiments, the method further comprises applying an adjuvant, such as crop oil concentrates (COC), to the planting area.

[0056] The present invention may also provide an agricultural method that improves the efficacy of an herbicide, by reducing plant injury, reducing necrosis, reducing bleaching, increasing early season vigor and / or increasing canopy formation. The methods may achieve a commercially acceptable rate of weed control.

[0057] Miscellaneous

[0058] Unless otherwise specified or indicated by context, the terms “a”, “an”, and “the” mean “one or more.” For example, “a molecule” should be interpreted to mean “one or more molecules.” As used herein, “about”, “approximately,” “substantially,” and “significantly” will be understood by persons of ordinary skill in the art and will vary to some extent on the context in which they are used. If there are uses of the term which are not clear to persons of ordinary skill in the art given the context in which it is used, “about” and “approximately” will mean plus or minus <10% of the particular term and “substantially” and “significantly” will mean plus or minus >10% of the particular term.

[0059] As used herein, the terms “include” and “including” have the same meaning as the terms “comprise” and “comprising.” The terms “comprise” and “comprising” should be interpreted as being “open” transitional terms that permit the inclusion of additional components further to thosecomponents recited in the claims. The terms “consist” and “consisting of’ should be interpreted as being “closed” transitional terms that do not permit the inclusion additional components other than the components recited in the claims. The term “consisting essentially of’ should be interpreted to be partially closed and allowing the inclusion only of additional components that do not fundamentally alter the nature of the claimed subject matter.

[0060] 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 herein, is intended merely to better illuminate the invention and does not pose a limitation on the scope of the invention unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention.

[0061] All references, including publications, patent applications, and patents, cited herein are hereby incorporated by reference to the same extent as if each reference were individually and specifically indicated to be incorporated by reference and were set forth in its entirety herein.

[0062] Preferred aspects of this invention are described herein, including the best mode known to the inventors for carrying out the invention. Variations of those preferred aspects may become apparent to those of ordinary skill in the art upon reading the foregoing description. The inventors expect a person having ordinary skill in the art to employ such variations as appropriate, and the inventors intend for the invention to be practiced otherwise than as specifically described herein. Accordingly, this invention includes all modifications and equivalents of the subject matter recited in the claims appended hereto as permitted by applicable law. Moreover, any combination of the above-described elements in all possible variations thereof is encompassed by the invention unless otherwise indicated herein or otherwise clearly contradicted by context.

[0063] EXAMPLES

[0064] Hydroxyphenylpyruvate dioxygenase (HPPD)-inhibiting herbicides are widely used in corn and typically cause bleaching / chlorosis symptomology to sensitive crops and weeds. The Examples demonstrate that wheat may be safely treated with HPPD-inhibiting herbicides when cloquintocet-mexyl and / or mefenpyr-diethyl is used as a safener, for example as a seed treatment. As demonstrated here, a cloquintocet-mexyl and / or mefenpyr-diethyl seed treatment in wheat improves the tolerance of the crop to HPPD-inhibiting herbicides, resulting in the crop having greater early-season vigor, less bleaching, less necrosis, and / or less injury relative to treated plotswhere the seed treatment is not used. The safening of wheat with cloquintocet-mexyl and / or mefenpyr-diethyl could potentially allow herbicides to be registered and commercially employed that are not currently being applied, or mitigate carryover restrictions from the planting of wheat behind com treated with HPPD herbicides.

[0065] Example 1

[0066] Methods

[0067] In a greenhouse experiment, two rows of ‘Buster’ wheat were seeded at a 0.5-inch depth into silt loam soil in trays. Two rows were seeded with 1) wheat not treated with a potential safener, 2) seeds treated with cloquintocet at 0.5 or 1.5 g active ingredient (ai) / kg-seed, 3) seeds treated with mefenpyr at 0.5 and 1.5 g ai / kg-seed. There were four replications for each treatment. Immediately after planting, herbicide treatments were applied using a boom-track spray chamber. Herbicides applied preemergence were topram ezone at 196 g ai / hectare (ha), mesotrione at 420 g ai / ha, and tembotrione at 276 g ai / ha. Immediately following treatment, herbicides were activated by overhead irrigation.

[0068] Injury ratings were visually taken at 21 days after treatment (DAT) along with determining plant density. At 28 DAT, photographs were taken of each tray to visually display the safening effects of the seed treatments. The results generated from each herbicide were evaluated independently of one another.

[0069] Results

[0070] Topramezone and tembotrione elicited little to no injury to wheat; therefore, the herbicide safener seed treatments did not improve wheat tolerance. Mesotrione did cause severe bleaching and stunting in wheat while cloquintocet and mefenpyr improved wheat tolerance to the herbicides (Figure 1). The rates to provide improved wheat safety for cloquintocet and mefenpyr were identified as 0.5 and 1.5 g ai / kg of seed, respectively. It is important to note that the herbicide rates tested here are more than 3 times the labeled rate in corn.

[0071] Example 2

[0072] Methods

[0073] Methodology was like that described for Experiment #1. In this experiment, ‘USG 3352’ was either not treated with a safener or treated with cloquintocet or mefenpyr at 0.5 and 1.5 g ai / kg of seed, respectively. Immediately after planting wheat, mesotrione was applied at either 0 or 560 g ai / ha utilizing standard application methods. Herbicides were activated through overheadirrigation immediately after application, and trays containing wheat received overhead irrigation at least twice daily throughout the experiment. Additionally, to elicit a greater wheat response to the herbicides and seed treatments, trays were placed in a growth chamber with a 10 / 15.6 C night / day temperature regime to place the crop under further stress.

[0074] Injury to wheat in the form of bleaching and overall phytotoxicity was visually rated at 7 days after crop emergence (DAE). Wheat density (live plants) was also counted at the first evaluation. Data were subjected to analysis of variance (ANOVA), and a studentized T-test was used to determine if the seed treatment added protection to the crop.

[0075] Results

[0076] Mesotrione caused > 20% injury and > 35% bleaching 7 DAE when wheat had no safener seed treatment (Figures 2 and 3). Wheat seed treated with cloquintocet or mefenpyr had plants that averaged < 3% injury or bleaching. Wheat plant density was not influenced by the various treatments.

[0077] Example 3

[0078] Methods

[0079] Field trials were conducted with the winter wheat variety ‘Hilliard’ planted under typical wheat production practices in Oct 2024. Seeds were treated with various herbicide safeners, in particular cloquintocet and mefenpyr at 0.5 and 1.5 g ai / kg of seed, respectively. The experiment was a randomized complete block design with four replications. Immediately after planting, mesotrione was applied at 210 g ai / ha using standard application methods. Herbicides were activated immediately after application using 1.9 cm of overhead irrigation. Wheat injury was visually estimated after uniform wheat emergence. Data were subjected to ANOVA and pairwise comparisons with studentized T-test was used to compare the safening potential of the seed treatments.

[0080] Results

[0081] Figure 4 shows wheat injury from mesotrione herbicide as influenced by different seed treatments. Use of cloquintocet and mefenpyr results in the least amount of wheat injury among all the safeners tested. In the absence of a seed treatment, mesotrione caused 65% injury, whereas cloquintocet and mefenpyr seed treatments reduced the injury to < 25%.Example 4

[0082] Methods

[0083] Field trials were conducted with the winter wheat variety ‘Hilliard’ planted under typical wheat production practices. Seeds were treated with cloquintocet and mefenpyr at 0.5 and 1.5 g ai / kg of seed, respectively. The experiment was a randomized complete block design with four replications. Immediately after planting, ‘Callisto’ herbicide was applied at 12 fl oz / a or 24 fl oz / a (containing about 420 g ai / ha or about 840 g ai / ha of mesotrione) using standard application methods, along with optional applications of adjuvants and safeners. Wheat injury was visually estimated after uniform wheat emergence. Appl Code A refers to application 5 days preemergence. Appl Code B refers to application 6 days post emergence.

[0084] Table 1. Seed and herbicide treatments for Example 4.

[0085]

[0086]

[0087]

[0088]

[0089] Results

[0090] Figure 5 shows percent wheat injury following mesotrione application 18 days (1*), 25 (2*), 32 (3*), and 39 (4*) days after first application of ‘Calisto’.

[0091] Figure 6 shows percent wheat bleaching following mesotrione application 18 days (5*), 25 (5*), 32 (7*), and 39 (8*) days after first application of ‘Calisto’.

[0092] Figure 7 shows percent wheat bleaching following mesotrione application 39 days after first application of ‘Calisto’.

[0093] Figure 8 shows wheat plants per meter row 20 days after first application of ‘Calisto’. Use of cloquintocet and / or mefenpyr reduced the level of wheat injury compared to applications without safeners.

[0094] Example 5

[0095] Methods

[0096] Field trials were conducted with the winter wheat variety ‘Hilliard’ planted under typical wheat production practices. Seeds were treated with various herbicide safeners, including cloquintocet and mefenpyr at 0.5 and 1.5 g ai / kg of seed, respectively. The experiment was a randomized complete block design with four replications. Immediately after planting, ‘Callisto’ at 24 fl oz / a (containing about 840 g ai / ha of mesotrione), ‘Capreno’ at 9 fl oz / a (containing about 227 g ai / ha of tembotrione), or ‘Impact’ at 4 fl oz / a (containing about 98 g ai / ha of topramezone) were applied using standard application methods. Wheat injury was visually estimated after uniform wheat emergence. Appl Code A refers to application 5 days preemergence.Table 1. Seed and herbicide treatments for Example 5.

[0097]

[0098]

[0099] Results

[0100] Figure 9 shows wheat plants per meter row 20 days after application of various herbicides. Figure 10 shows percent wheat injury 11 (2*), 18 (3*), 25 (4*), 32 (5*), and 40 (6*) days after application of various herbicides.

[0101] Figure 11 shows percent wheat bleaching 25 (7*), 32 (8*), and 40 (9*) days after application of various herbicides

[0102] Figure 12 shows percent wheat necrosis 32 (10*) and 40 (11*) days after application of various herbicides.

[0103] Use of cloquintocet and / or mefenpyr reduced the level of wheat injury compared to other safeners.

Claims

CLAIMSWhat is claimed is:

1. A method of growing wheat comprising applying an effective amount of a safener to wheat seed prior to planting and applying an effective amount of a hydroxyphenylpyruvate dioxygenase (HPPD)-inhibiting herbicide to the planting area, wherein the safener is cloquintocet-mexyl, mefenpyr-diethyl, or a combination thereof.

2. The method of claim 1, wherein the herbicide is a triketone, a pyrazolone, a pyrazole, an isoxazole, or an azole carboxamide.

3. The method of claim 1 , wherein the herbicide is mesotrione, tembotrione or topramezone.

4. The method of claim 1, wherein the herbicide is mesotrione.

5. The method of any one of claims 1-4, wherein the herbicide is applied after the wheat seed is planted.

6. The method of claim 5, wherein the herbicide is applied preemergence.

7. The method of any one of claims 1-6, wherein the method comprises applying the herbicide at a greater than recommended amount.

8. The method of any one of claims 1-7, wherein the effective amount of the herbicide is between 0.01 - 5 kilograms active ingredient per hectare.

9. The method of any one of claims 1-8, wherein the effective amount of the herbicide is between 0.01 - 0.5 kilograms active ingredient per hectare.

10. The method of any one of claims 1-9, wherein the effective amount of the herbicide is an amount of the herbicide that results in commercially acceptable rate of weed control.

11. The method of any one of claims 1-10, wherein the effective amount of herbicide is an amount of herbicide, that in combination with the use of the safener, results in commercially acceptable weed control and the same or lower amount of injury, bleaching, necrosis, or a combination thereof, as compared to a control plant.

12. The method of any one of claims 1-11, wherein the effective amount of herbicide is an amount of herbicide, that in combination with the use of the safener, results in commercially acceptable weed control and improved early season vigor as compared to a control plant.

13. The method of claim 12, wherein the effective amount of herbicide is an amount of herbicide, that in combination with the use of the safener, results in commerciallyacceptable weed control and improved wheat density, wheat biomass, or a combination thereof, as compared to a control plant.

14. The method of any one of claims 1-13, wherein the effective amount of the safener is between 0.1 - 10 grams of safener per kilogram of seed.

15. The method of any one of claims 1-14, wherein the effective amount of the safener is between 0.1 - 3 grams of safener per kilogram of seed.

16. The method of any one of claims 1-15, wherein the method comprises applying an effective amount of cloquintocet-mexyl to wheat seed prior to planting.

17. The method of any one of claims 1-15, wherein the method comprises applying an effective amount of mefenpyr-di ethyl to wheat seed prior to planting.

18. The method of any one of claims 1-17, wherein the herbicide is applied as a suspension concentrate.

19. The method of any one of claims 1-18, wherein the method further comprises applying an adjuvant to the planting area.

20. The method of any one of claims 1-19, wherein the method further comprises applying an effective amount of cloquintocet-mexyl, mefenpyr-diethyl, or a combination thereof, to the planting area.

Images