Compositions of ethoxylated lecithin and PPO inhibitors

Abstract

The present disclosure provides herbicidal compositions comprising a protoporphyrinogen oxidase (PPO) inhibitor (e.g., fomesafen) and ethoxylated lecithin and methods for controlling unwanted plant growth.

Description

COMPOSITIONS OF ETHOXYLATED LECITHIN AND PPO INHIBITORSFIELD

[0001] The present disclosure relates to herbicidal compositions comprising a protoporphyrinogen oxidase (PPO) inhibitor and ethoxylated lecithin and methods for controlling unwanted plant growth.CROSS REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of U.S. Provisional Application No. 63 / 567,751, filed March 20, 2024, the content of which is herein incorporated by reference in its entirety.BACKGROUND

[0003] With the increased demand for high crop productivity, crop protection chemicals (e.g., pesticides, insecticides, herbicides, and fungicides) are widely used to prevent crop damage and increase crop yields. Increasing the effectiveness of crop protection chemical agents can be done by engineering new or existing chemicals. Alternatively, adjuvants can be used to enhance the effectiveness of the crop protection chemicals. Adjuvants assist in the formulation of the crop protection chemical(s) and / or the application of the crop protection chemical(s). Adjuvants commonly include drift controlling agents, stickers, emulsifiers, wetting agents, water conditioners and penetrants. The development of formulations of crop protection chemical(s) with adjuvants that increase the effectiveness of the crop protection chemical(s) would result in a significant contribution to the viable options available to increase crop productivity.SUMMARY

[0004] Disclosed herein are herbicidal compositions comprising a protoporphyrinogen oxidase (PPO) inhibitor, or an agriculturally acceptable salt thereof, and ethoxylated lecithin. In some embodiments, the PPO inhibitor is fomesafen, or an agriculturally acceptable salt thereof.

[0005] In some embodiments, the composition comprises about 0.01% v / v to about 30.0% v / v PPO inhibitor, or an agriculturally acceptable salt thereof. In some embodiments, the composition comprises about 0.01% v / v to about 5.0% v / v PPO inhibitor, or an agriculturally acceptable salt thereof. In some embodiments, the composition comprises about 0.05% v / v to about 4.0% v / v PPO inhibitor, or an agriculturally acceptable salt thereof. In some embodiments, the composition comprises about 10.0% v / v to about 30.0% v / v PPO inhibitor, or an agriculturally acceptable salt thereof. In some embodiments, the composition comprises about 20.0% v / v to about 30.0% v / v PPO inhibitor, or an agriculturally acceptable salt thereof.

[0006] In some embodiments, the composition comprises about 0.01% v / v to about 30.0% v / v fomesafen, or an agriculturally acceptable salt thereof. In some embodiments, the composition comprises about 0.01% v / v to about 5.0% v / v fomesafen, or an agriculturally acceptable salt thereof. In some embodiments, the composition comprises about 0.05% v / v to about 4.0% v / v fomesafen, or an agriculturally acceptable salt thereof. In some embodiments, the composition comprises about 10.0% v / v to about 30.0% v / v fomesafen, or an agriculturally acceptable salt thereof. In some embodiments, the composition comprises about 20.0% v / v to about 30.0% v / v fomesafen, or an agriculturally acceptable salt thereof.

[0007] In some embodiments, the composition comprises about 0.001% v / v to about 20.0% v / v ethoxylated lecithin. In some embodiments, the composition comprises about 0.001% v / v to about 0.5% v / v ethoxylated lecithin. In some embodiments, the composition comprises about 0.01% v / v to about 0.2% v / v ethoxylated lecithin. In some embodiments, the composition comprises about 5% v / v to about 20% v / v ethoxylated lecithin. In some embodiments, the composition comprises about 5% v / v to about 10% v / v ethoxylated lecithin.

[0008] In some embodiments, the composition further comprises a pesticide, fertilizer, additional herbicide, or a combination thereof.

[0009] In some embodiments, the composition further comprises a surfactant.

[0010] Also disclosed herein are methods for controlling undesired plant growth. In some embodiments, the methods comprise applying an effective amount of a composition as disclosed herein to the soil or growth medium. In some embodiments, the methods comprise applying an effective amount of a composition as disclosed herein to the undesired plant. In some embodiments, the undesired plant is a broadleaf weed, a grass or grassy weed, a sedge, or a combination thereof.

[0011] In some embodiments, the applying comprises irrigating, spraying, in-furrow application, or direct incorporation into the soil or growth medium.

[0012] In some embodiments, the applying is prior to undesired plant emergence. In some embodiments, the applying is after emergence of the undesired plant.

[0013] In some embodiments, a desired plant or crop resides in the soil or growth medium or is comingled with the undesired plant. In some embodiments, the desired plant or crop is beans, groundnuts, cotton, or potatoes. In some embodiments, the applying is prior to planting of the desired plant or crop.

[0014] In some embodiments, the method increases uptake and / or penetration of the protoporphyrinogen oxidase (PPO) inhibitor in the undesired plant.

[0015] Other embodiments of the disclosure will be apparent considering the following detailed description.BRIEF DESCRIPTION OF THE DRAWINGS

[0016] FIGS. 1A-1C show Kochia control (FIGS. 1A-1B) and biomass reduction (FIG. 1C) for indicated treatments and an untreated control.

[0017] FIGS. 2A-2B are graphs of Kochia overall biomass (FIG. 2A) and percentage of biomass reduction (FIG. 2B) for indicated treatments and an untreated control (UTC).

[0018] FIGS. 3A-3B are graphs of Waterhemp overall biomass (FIG. 3 A) and percentage of biomass reduction (FIG. 3B) for indicated treatments and an untreated control (UTC).

[0019] FIG. 4 is images of 5 pL droplets of fomesafen formulations (alone (Reflex) or in formulations with ethoxylated lecithin (EXT 1649) or two industry standard surfactants (EXT 1650 and EXT1651) applied on the surface of waterhemp leaves.

[0020] FIGS. 5A-5C show efficacy of fomesafen applied alone (Reflex) or in formulations with ethoxylated lecithin (EXT 1649) or two industry standard surfactants (EXT1650 and EXT1651). Efficacy was assessed by measuring fresh weight (FIG. 5A), percent injury (FIG. 5B), and survival (FIG. 5C) of waterhemp 21 days after treatment.

[0021] FIGS. 6A-6D are images of fomesafen applied as Reflex alone (FIG. 6A) or in formulations with ethoxylated lecithin (FIG. 6B) and two industry standard surfactants (FIGS. 6C- 6D) five days after treatment.

[0022] FIG. 7 is a graph showing the absorption of fomesafen formulations (alone (Fomesafen) or in formulations with ethoxylated lecithin (+49) or two industry standard surfactants (+50 and +51).

[0023] FIG. 8 is a graph of the effect of formulation on protoporphyrin accumulation in plants treated with 1 X the identified formulations (alone (Fomesafen) or in formulations with ethoxylated lecithin (EXT1649) or two industry standard surfactants (EXT1650 and EXT1651)). n=12 and error bars are MSE. ANOVA analysis indicated significant difference in the means (p= 0.00475), means were separated according to Fischer’s LSD test (p= 0.05).

[0024] FIG. 9 shows the effect of (Fomesafen alone (Fom) or the adjuvant comprising ethoxylated lecithin (EXT 1649 or 49) or two industry standard surfactant packages (EXT 1650+50 and +51) on electrolyte leakage based on the conductivity after 16 h dark incubation and 8 h exposure to high light intensity.

[0025] FIG. 10 is a graph of reactive oxygen species (ROS) accumulation in the presence of fomesafen alone (Fomesafen) or in formulations with ethoxylated lecithin (49) or two industry standard surfactants (50 and 51).

[0026] FIG. 11 is a graph of the quantification of malonaldehyde (MDA) for the identified formulations (Reflex (Fomesafen) or in formulations with ethoxylated lecithin (EXT 1649) or two industry standard surfactants (EXT1650 and EXT1651)).DETAILED DESCRIPTION

[0027] The present disclosure provides compositions and methods to control undesired plant growth in a soil or growth medium, e.g., where a desired plant or crop resides. The compositions include a PPO inhibitor, or an agriculturally acceptable salt thereof, and ethoxylated lecithin. The disclosed combinations provide enhanced control of undesired plants (e.g., weeds), as compared to corresponding treatments using either a PPO inhibitor or ethoxylated lecithin alone. As described herein, a herbicidal formulation comprising an exemplary PPO inhibitor, fomesafen, and ethoxylated lecithin improved weed control and reduced survival compared to industry standard surfactants, improved fomesafen uptake (both speed and total amount) and penetration into the plant, increased the buildup of protoporphyrin, the first downstream metabolite produced from the PPO herbicide mode of action, and increased the buildup of reactive oxygen species, the responsible agent for killing the plant, all while showing a lower potential for phytotoxicity compared to industry standard surfactants.

[0028] Section headings as used in this section and the entire disclosure herein are merely for organizational purposes and are not intended to be limiting.1. Definitions

[0029] The terms “comprise(s),” “include(s),” “having,” “has,” “can,” “contain(s),” and variants thereof, as used herein, are intended to be open-ended transitional phrases, terms, or words that do not preclude the possibility of additional acts or structures. The singular forms “a,” “and” and “the” include plural references unless the context clearly dictates otherwise. The present disclosure also contemplates other embodiments “comprising,” “consisting of’ and “consisting essentially of,” the embodiments or elements presented herein, whether explicitly set forth or not.

[0030] For the recitation of numeric ranges herein, each intervening number there between with the same degree of precision is explicitly contemplated. For example, for the range of 6-9, the numbers 7 and 8 are contemplated in addition to 6 and 9, and for the range 6.0-7.0, the number 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, and 7.0 are explicitly contemplated.

[0031] Unless otherwise defined herein, scientific and technical terms used in connection with the present disclosure shall have the meanings that are commonly understood by those of ordinary skill in the art. The meaning and scope of the terms should be clear; in the event, however of any latentambiguity, definitions provided herein take precedent over any dictionary or extrinsic definition. Further, unless otherwise required by context, singular terms shall include pluralities and plural terms shall include the singular.

[0032] As used herein, the term “herbicide” refers to a compound or combination of compounds that reduces or kills undesirable and unwanted plants such as, but not limited to, deleterious, noxious, or problematic weeds, broadleaf plants, grasses, and sedges. Herbicide use may produce an observable desired effect to reduce unwanted plant growth, including the effects of plant necrosis, leaf chlorosis, plant death, root and shoot growth inhibition, reproduction inhibition, inhibition of proliferation, and removal, destruction, or otherwise diminishing the occurrence and activity of undesirable, unwanted plants.

[0033] Preferred methods and materials are described below, although methods and materials similar or equivalent to those described herein can be used in practice or testing of the present disclosure. All publications, patent applications, patents and other references mentioned herein are incorporated by reference in their entirety. The materials, methods, and examples disclosed herein are illustrative only and not intended to be limiting.2. Compositions

[0034] Provided herein are compositions for enhancing the effectiveness of herbicides which inhibit the protoporphyrinogen oxidase (PPO) enzyme in plants, so-called PPO inhibitors. PPO inhibitors block the oxidation of protoporphyrinogen critical for protoporphyrin IX synthesis, a precursor molecule necessary for the biosynthesis of chlorophyll and heme. PPO inhibitors include, without limitation, acifluorfen, carfentrazone, flumioxazin, flumiclorac, fluthiacet, fomesafen, lactofen, oxyfluorfen, pyraflufen-ethyl, saflufenacil and sulfentrazone.

[0035] In some embodiments, the PPO inhibitor is fomesafen, 5-[2-chloro-4-(trifluoromethyl) phenoxy]-N-methylsulfonyl-2-nitrobenzamide. Fomesafen may be in the form of the free base as well as an agriculturally acceptable salt thereof. Examples of agriculturally acceptable salts include both anhydrous as well as hydrated forms of fomesafen salts with alkaline or earth alkaline metals or ammonium or organoammonium salts, for example, sodium, potassium, ammonium, and isopropyl ammonium. In some embodiments, fomesafen is included in the formulation in the form of a sodium salt.

[0036] The ethoxylated lecithin may be derived from a variety of sources. The compositions disclosed herein are not limited by the source of ethoxylated lecithin.

[0037] In some embodiments, the ethoxylated lecithin is produced by the reaction of crude soybean lecithin and ethylene oxide, as described in U.S. Pat. No. 2,310,679, incorporated herein byreference. Ethoxylated lecithin is commercially available, for example, Eucarol NA-6415 and ETMA NA-6416 from Lamberti USA Inc. in Conshohocken, PA, and SURFLEX L 1000 MC from Exacto, Inc. in Sharon, WI. Ethoxylated lecithin from these commercial sources is presumably ethoxylated crude soybean lecithin, also referred to as phospholipid-enriched soybean oil, obtained from ethoxylating a crude soybean lecithin containing from 5-30 wt %, preferably 8-10 wt %, and more preferably about 10 wt % phospholipids. The crude soybean lecithin is a fluid under ambient temperature and pressure. Ethoxylation may be carried out according to the process of U.S. Pat. No. 2,310,679 without the presence of an inert solvent. Triglycerides contained in the soybean oil may include, for example, C16 saturated and C18 saturated, monounsaturated and polyunsaturated fatty acids, particularly palmitic, stearic, oleic, linoleic, and linolenic acid, with an iodine value of 120- 140. The crude soybean lecithin is reacted with 30-90 wt %, preferably 50-70 wt % ethylene oxide between 90- 180° C in the presence of a basic catalyst such as potassium hydroxide, at a pressure between 1 and 5 bar for 60-300 minutes. Small amounts of glycerol (e.g., 1-4 wt %) may be added as an initiator. The reaction conditions (e.g., time and pressure) may be set to obtain a final product comprising 10-200 ethylene oxide units with an ideal amount of 20-50 ethylene oxide units. Temperature is preferably maintained below 170° C (ideally at ~ 160° C) to avoid excessive discoloration. For example, preferred ethoxylated lecithin may be phospholipids having 25 moles ethoxylate functional group incorporated therein (having a number average molecular weight (NAVG MW) of about 1000) and / or lecithin having 30 moles ethoxylate functional group incorporated therein (having a NAVG MW of about 1200). The ethoxylated lecithin for use in the disclosed methods and compositions is not limited to any particular molar amounts or NAVG MW.

[0038] Ethoxylated lecithin can also be derived from crude lecithin from other seed oil crops as well as lecithin derived from chicken eggs. Additionally, ethoxylated lecithin can be derived from any source that has an enriched source of phospholipids.

[0039] In some cases, a composition may be produced by simply physically mixing (“tank mixing”) commercially available products containing a PPO inhibitor (e.g., fomesafen) and ethoxylated lecithin. Alternatively, a package may be manufactured and sold which contains a PPO inhibitor (e.g., fomesafen) and ethoxylated lecithin in separate containers, but co-packaged.

[0040] In some embodiments, the compositions are previously prepared formulations containing the PPO inhibitor (e.g., fomesafen) and ethoxylated lecithin. The formulations can be ready for use as provided or be a concentrated form which requires dilution prior to use. Suitable liquid compositions would include solutions or emulsions containing the PPO inhibitor (e.g., fomesafen) and ethoxylated lecithin. A solid product containing a PPO inhibitor (e.g., fomesafen) andethoxylated lecithin could also be produced, for instance, as impregnated granules or flowable powders.

[0041] The concentration of a PPO inhibitor and / or ethoxylated lecithin in the herbicidal compositions are generally from about 0.001 to about 98 percent by weight. Concentrations from about 0.01 to about 90 percent by weight are often employed. In compositions designed to be employed as concentrates, the active ingredient is generally present in a concentration from about 5 to about 98 weight percent. Such compositions are typically diluted with an inert carrier, such as water, before application. The diluted compositions can contain about 0.001 to about 1 percent PPO inhibitor and / or ethoxylated lecithin.

[0042] The concentration of the PPO inhibitor, or an agriculturally acceptable salt thereof, may range from about 0.01% v / v to about 99.9% v / v. The concentration of the PPO inhibitor, or an agriculturally acceptable salt thereof, may be about 0.01% v / v, about 0.02% v / v, about 0.03% v / v, about 0.04% v / v, about 0.05% v / v, about 0.06% v / v, about 0.07% v / v, about 0.08% v / v, about 0.09% v / v, about 0.1% v / v, about 0.2% v / v, about 0.3% v / v, about 0.4% v / v, about 0.5% v / v, about 0.6% v / v, about 0.7% v / v, about 0.8% v / v, about 0.9% v / v, about 1.0 % v / v, about 2.0 % v / v, about 5.0 % v / v, about 10.0 % v / v, about 15.0 % v / v, about 20.0 % v / v, about 25.0 % v / v, about 30.0 % v / v, about 35.0 % v / v, about 40.0 % v / v, about 45.0 % v / v, about 50.0 % v / v, about 55.0 % v / v, about 60.0 % v / v, about 65.0 % v / v, about 70.0 % v / v, about 75.0 % v / v, about 80.0 % v / v, about 85.0 % v / v, about 90.0 % v / v, about 95.0 % v / v, about 98.0 % v / v, or about 99.0 % v / v.

[0043] In some embodiments, the concentration of the PPO inhibitor, or an agriculturally acceptable salt thereof, is from about 0.01% v / v to about 30% v / v. The concentration of the PPO inhibitor, or an agriculturally acceptable salt thereof, may be about 0.01% v / v, about 0.02% v / v, about 0.03% v / v, about 0.04% v / v, about 0.05% v / v, about 0.06% v / v, about 0.07% v / v, about 0.08% v / v, about 0.09% v / v, about 0.1% v / v, about 0.2% v / v, about 0.3% v / v, about 0.4% v / v, about 0.5% v / v, about 0.6% v / v, about 0.7% v / v, about 0.8% v / v, about 0.9% v / v, about 1.0 % v / v, about 2.0 % v / v, about 5.0 % v / v, about 10.0 % v / v, about 15.0 % v / v, about 20.0 % v / v, about 25.0 % v / v, about 30.0 % v / v

[0044] In some embodiments, the concentration of the PPO inhibitor, or an agriculturally acceptable salt thereof, may range from about 0.01% v / v to about 5.0% v / v (e.g., about 0.01% v / v to about 0.1% v / v, about 0.01% v / v to about 0.5% v / v, about 0.01% v / v to about 1.0% v / v, about 0.01% v / v to about 2.0% v / v, about 0.01% v / v to about 3.0% v / v, about 0.01% v / v to about 4.0% v / v, e.g., about 0.05% v / v to about 0.1% v / v, about 0.05% v / v to about 0.5% v / v, about 0.05% v / v to about 1.0% v / v, about 0.05% v / v to about 2.0% v / v, about 0.05% v / v to about 3.0% v / v, about 0.05% v / v to about 4.0% v / v, about 0.5% v / v to about 5.0% v / v). The concentration of the PPO inhibitor, or anagriculturally acceptable salt thereof, may be about 0.01% v / v, about 0.02% v / v, about 0.03% v / v, about 0.04% v / v, about 0.05% v / v, about 0.06% v / v, about 0.07% v / v, about 0.08% v / v, about 0.09% v / v, about 0.1% v / v, about 0.2% v / v, about 0.3% v / v, about 0.4% v / v, about 0.5% v / v, about 0.6% v / v, about 0.7% v / v, about 0.8% v / v, about 0.9% v / v, about 1.0 % v / v, about 1.5 %v / v, about 2.0 %v / v, about 2.5 %v / v, about 3.0 %v / v, about 3.5 %v / v, about 4.0 %v / v, about 4.5 %v / v, or about 5.0 %v / v.

[0045] In some embodiments, the concentration of the PPO inhibitor, or an agriculturally acceptable salt thereof, may range from about 10.0% v / v to about 30.0% v / v (e.g., about 10.0% v / v to about 15.0% v / v, about 10.0% v / v to about 20.0% v / v, about 15.0% v / v to about 25.0% v / v, about 15.0% v / v to about 30.0% v / v, about 20.0% v / v to about 30.0% v / v). The concentration of the PPO inhibitor, or an agriculturally acceptable salt thereof, may be about 10.0 % v / v, about 11.0 % v / v, about 12.0 % v / v, about 13.0 % v / v, about 14.0 % v / v, about 15.0 % v / v, about 16.0 % v / v, about 17.0 % v / v, about 18.0 % v / v, about 19.0 % v / v, about 20.0 % v / v, about 21.0 % v / v, about 22.0 % v / v, about 23.0 % v / v, about 24.0 % v / v, about 25.0 % v / v, about 26.0 % v / v, about 27.0 % v / v, about 28.0 % v / v, about 29.0 % v / v, about 30.0 % v / v.

[0046] The concentration of fomesafen, or an agriculturally acceptable salt thereof, may range from about 0.01% v / v to about 99.9% v / v. The concentration of the fomesafen, or an agriculturally acceptable salt thereof, may be about 0.01% v / v, about 0.02% v / v, about 0.03% v / v, about 0.04% v / v, about 0.05% v / v, about 0.06% v / v, about 0.07% v / v, about 0.08% v / v, about 0.09% v / v, about 0.1% v / v, about 0.2% v / v, about 0.3% v / v, about 0.4% v / v, about 0.5% v / v, about 0.6% v / v, about 0.7% v / v, about 0.8% v / v, about 0.9% v / v, about 1.0 % v / v, about 2.0 % v / v, about 5.0 % v / v, about 10.0 % v / v, about 15.0 % v / v, about 20.0 % v / v, about 25.0 % v / v, about 30.0 % v / v, about 35.0 % v / v, about 40.0 % v / v, about 45.0 % v / v, about 50.0 % v / v, about 55.0 % v / v, about 60.0 % v / v, about 65.0 % v / v, about 70.0 % v / v, about 75.0 % v / v, about 80.0 % v / v, about 85.0 % v / v, about 90.0 % v / v, about 95.0 % v / v, about 98.0 % v / v, or about 99.0 % v / v.

[0047] In some embodiments, the concentration of fomesafen, or an agriculturally acceptable salt thereof, is from about 0.01% v / v to about 30% v / v. The concentration of the fomesafen, or an agriculturally acceptable salt thereof, may be about 0.01% v / v, about 0.02% v / v, about 0.03% v / v, about 0.04% v / v, about 0.05% v / v, about 0.06% v / v, about 0.07% v / v, about 0.08% v / v, about 0.09% v / v, about 0.1% v / v, about 0.2% v / v, about 0.3% v / v, about 0.4% v / v, about 0.5% v / v, about 0.6% v / v, about 0.7% v / v, about 0.8% v / v, about 0.9% v / v, about 1.0 % v / v, about 2.0 % v / v, about 5.0 % v / v, about 10.0 % v / v, about 15.0 % v / v, about 20.0 % v / v, about 25.0 % v / v, about 30.0 % v / v

[0048] In some embodiments, the concentration of fomesafen, or an agriculturally acceptable salt thereof, may range from about 0.01% v / v to about 5.0% v / v (e.g., about 0.01% v / v to about 0.1%v / v, about 0.01% v / v to about 0.5% v / v, about 0.01% v / v to about 1.0% v / v, about 0.01% v / v to about 2.0% v / v, about 0.01% v / v to about 3.0% v / v, about 0.01% v / v to about 4.0% v / v, e.g., about 0.05% v / v to about 0.1% v / v, about 0.05% v / v to about 0.5% v / v, about 0.05% v / v to about 1.0% v / v, about 0.05% v / v to about 2.0% v / v, about 0.05% v / v to about 3.0% v / v, about 0.05% v / v to about 4.0% v / v, about 0.5% v / v to about 5.0% v / v). The concentration of the fomesafen or an agriculturally acceptable salt thereof, may be about 0.01% v / v, about 0.02% v / v, about 0.03% v / v, about 0.04% v / v, about 0.05% v / v, about 0.06% v / v, about 0.07% v / v, about 0.08% v / v, about 0.09% v / v, about 0.1% v / v, about 0.2% v / v, about 0.3% v / v, about 0.4% v / v, about 0.5% v / v, about 0.6% v / v, about 0.7% v / v, about 0.8% v / v, about 0.9% v / v, about 1.0 % v / v, about 1.5 %v / v, about 2.0 %v / v, about 2.5 %v / v, about 3.0 %v / v, about 3.5 %v / v, about 4.0 %v / v, about 4.5 %v / v, or about 5.0 %v / v.

[0049] In some embodiments, the concentration of fomesafen, or an agriculturally acceptable salt thereof, may range from about 10.0% v / v to about 30.0% v / v (e.g., about 10.0% v / v to about 15.0% v / v, about 10.0% v / v to about 20.0% v / v, about 15.0% v / v to about 25.0% v / v, about 15.0% v / v to about 30.0% v / v, about 20.0% v / v to about 30.0% v / v). The concentration of the fomesafen, or an agriculturally acceptable salt thereof, may be about 10.0 % v / v, about 11.0 % v / v, about 12.0 % v / v, about 13.0 % v / v, about 14.0 % v / v, about 15.0 % v / v, about 16.0 % v / v, about 17.0 % v / v, about 18.0 % v / v, about 19.0 % v / v, about 20.0 % v / v, about 21.0 % v / v, about 22.0 % v / v, about 23.0 % v / v, about 24.0 % v / v, about 25.0 % v / v, about 26.0 % v / v, about 27.0 % v / v, about 28.0 % v / v, about 29.0 % v / v, about 30.0 % v / v.

[0050] The concentration of the ethoxylated lecithin may range from about 0.001% v / v to about 99.9% v / v. The concentration of the ethoxylated lecithin may be about 0.001% v / v, about 0.005% v / v, about 0.01% v / v, about 0.02% v / v, about 0.03% v / v, about 0.04% v / v, about 0.05% v / v, about 0.06% v / v, about 0.07% v / v, about 0.08% v / v, about 0.09% v / v, about 0.1% v / v, about 0.2% v / v, about 0.3% v / v, about 0.4% v / v, about 0.5% v / v, about 0.6% v / v, about 0.7% v / v, about 0.8% v / v, about 0.9% v / v, about 1.0 % v / v, about 2.0 % v / v, about 5.0 % v / v, about 10.0 % v / v, about 15.0 % v / v, about 20.0 % v / v, about 25.0 % v / v, about 30.0 % v / v, about 35.0 % v / v, about 40.0 % v / v, about 45.0 % v / v, about 50.0 % v / v, about 55.0 % v / v, about 60.0 % v / v, about 65.0 % v / v, about 70.0 % v / v, about 75.0 % v / v, about 80.0 % v / v, about 85.0 % v / v, about 90.0 % v / v, about 95.0 % v / v, about 98.0 % v / v, or about 99.0 % v / v.

[0051] In some embodiments, the concentration of the ethoxylated lecithin is between about 0.001% v / v to about 20.0% v / v. The concentration of the ethoxylated lecithin may be about 0.001% v / v to about 0.01% v / v, about 0.001% v / v to about 0.2% v / v, about 0.001% v / v to about 0.5% v / v, about 0.001% v / v to about 1.0% v / v, about 0.001% v / v to about 5.0% v / v, about 0.001% v / v to about 10.0% v / v, about 0.001% v / v to about 15.0% v / v, about 0.01% v / v to about 0.2% v / v, about 0.01%v / v to about 0.5% v / v, about 0.01% v / v to about 1.0% v / v, about 0.01% v / v to about 5.0% v / v, about 0.01% v / v to about 10.0% v / v, about 0.01% v / v to about 15.0% v / v, about 0.01% v / v to about 20.0% v / v, about 0.1% v / v to about 0.2% v / v, about 0.1% v / v to about 0.5% v / v, about 0.1% v / v to about 1.0% v / v, about 0.1% v / v to about 5.0% v / v, about 0.1% v / v to about 10.0% v / v, about 0.1% v / v to about 15.0% v / v, about 0.1% v / v to about 20.0% v / v, about 0.5% v / v to about 1.0% v / v, about 0.5% v / v to about 5.0% v / v, about 0.5% v / v to about 10.0% v / v, about 0.5% v / v to about 15.0% v / v, about 0.5% v / v to about 20.0% v / v, about 1.0% v / v to about 5.0% v / v, about 1.0% v / v to about 10.0% v / v, about 1.0% v / v to about 15.0% v / v, about 1.0% v / v to about 20.0% v / v, about 5.0% v / v to about 10.0% v / v, about 5.0% v / v to about 15.0% v / v, about 5.0% v / v to about 20.0% v / v, about 10.0% v / v to about 15.0% v / v, about 10.0% v / v to about 20.0% v / v, or about 15.0% v / v to about 20.0% v / v.

[0052] In some embodiments, the concentration of the ethoxylated lecithin is between about 0.001% v / v to about 0.5% v / v. The concentration of the ethoxylated lecithin may be about 0.001% v / v, about 0.005% v / v, about 0.01% v / v, about 0.05% v / v, about 0.1% v / v, about 0.2% v / v, about 0.3% v / v, about 0.4% v / v, or about 0.5% v / v.

[0053] In some embodiments, the concentration of the ethoxylated lecithin is between about 5.0% v / v to about 20% v / v. The concentration of the ethoxylated lecithin may be about 5.0% v / v, about 6.0% v / v, about 7.0% v / v, about 8.0% v / v, about 9.0% v / v, about 10.0% v / v, about 11.0% v / v, about 12.0% v / v, about 13.0% v / v, about 14.0% v / v, about 15.0% v / v, about 16.0% v / v, about 17.0% v / v, about 18.0% v / v, about 19.0% v / v, or about 20.0% v / v.

[0054] In some embodiments, the concentration of the PPO inhibitor (e.g., fomesafen), or an agriculturally acceptable salt thereof, may range from about 0.01% v / v to about 1.0% v / v (inclusive of the subranges and concentrations described above) and the concentration of the ethoxylated lecithin is between about 0.001% v / v to about 0.5% v / v (inclusive of the subranges and concentrations described above). In select embodiments, the concentration of the PPO inhibitor (e.g., fomesafen), or an agriculturally acceptable salt thereof, may range from about 0.1% v / v to about 0.5% v / v (inclusive of the subranges and concentrations described above) and the concentration of the ethoxylated lecithin is between about 0.01% v / v to about 0.2% v / v (inclusive of the subranges and concentrations described above).

[0055] In some embodiments, the concentration of the PPO inhibitor (e.g., fomesafen), or an agriculturally acceptable salt thereof, may range from about 10.0% v / v to about 30.0% v / v (inclusive of the subranges and concentrations described above) and the concentration of the ethoxylated lecithin is between about 5.0% v / v to about 20% v / v (inclusive of the subranges and concentrations described above). In select embodiments, the concentration of the PPO inhibitor (e.g., fomesafen), or an agriculturally acceptable salt thereof, may range from about 20.0% v / v to about 30.0% v / v(inclusive of the subranges and concentrations described above) and the concentration of the ethoxylated lecithin is between about 5.0% v / v to about 10% v / v (inclusive of the subranges and concentrations described above).

[0056] The ratio of the PPO inhibitor (e.g., fomesafen), or an agriculturally acceptable salt thereof, to ethoxylated lecithin is greater than 1 :1, based on v / v. In some embodiments, the ratio of the PPO inhibitor (e.g., fomesafen), or an agriculturally acceptable salt thereof, to ethoxylated lecithin is 2: 1 to 10: 1, based on v / v. In select embodiments, the ratio of the PPO inhibitor (e.g., fomesafen), or an agriculturally acceptable salt thereof, to ethoxylated lecithin is 2: 1 to 4: 1, based on v / v. The ratio of the PPO inhibitor (e.g., fomesafen), or an agriculturally acceptable salt thereof, to ethoxylated lecithin may be about 2: 1, about 2.5: 1, about 3: 1, about 3.5:1 or about 4: 1, based on v / v. In select embodiments, the ratio of the PPO inhibitor (e.g., fomesafen), or an agriculturally acceptable salt thereof, to ethoxylated lecithin is between 2: 1 and 2.5:1.

[0057] The composition may comprise other active agents which prevent plant or crop damage, aid in growth, viability, and / or productivity of the desired plant or crop; aid and assist in the application of the composition (e.g., stabilizers, fillers, matrix elements, carriers); act as a solvent for the ingredients in the composition; or act as a preservative for the composition.

[0058] The compositions may further comprise other chemical and non-chemical additives, adjuvants, and / or treatment agents including, but not limited to: chemical and non-chemical pesticides (e.g., fungicides, insecticides, miticides, nematicides), fertilizers, nutrients, minerals, hormones (e.g., auxins, cytokinins, gibberellins, ethylene, and abscisic acid), plant growth enhancers or stimulants, wetting agents, spreading agents, dispersing agents, adhesive agents, buffering agents, coating agents, resins, suspension agents, stickers, penetrants, preservatives, and the like.

[0059] Exemplary fungicides include, but are not limited to: thiabendazole; iprodione; vinclozolin; imazilil; triforine; fenarimol; bitertanol; cyproconazole; difenoconazole; fenbuconazole; flusilazole; ipconazole; metconazole; myclobutanil; propiconazole; prothioconazole; tebuconazole; tetraconazole; triadimefon; triadimenol; triticonazole; metalxyl; mefenoxam; cyprodinil; azoxystrobin; picoxystrobin; pyraclostrobin; etridiazole; fenhexamid; polyoxin; fluazinam; dimethomorph; acibenzolar-S-methyl; chlorothalonil; chloroneb; dicloran; quintozene (PCNB); famoxadone; fenamidone; mineral oils; organic oils.

[0060] Exemplary nematicides include, but are not limited to, 1 ,3 dichloropropene, chloropicrin, metam sodium, metam potassium, dimethyl disulfide, allyl isothiocyanate, oxamyl, fluensulfone, fluopyram, ethoprop, spirotetramat, terbufos, and fluazaindolizine.

[0061] Exemplary insecticides and miticides include, but are not limited to: acephate, aldicarb, azinphos methyl, Bacillus thuringiensis, carbaryl, chlorpyrifos, cyhexatin, cypermethrin, diazinon,dicofol, dicrotophos, difhibenzuron, dimethoate, disulfoton, endosulfan, Ethion, fluvalinate, fonofos, formetanate hydrochloride, lindane, malathion, methamidophos, methidathion, methomyl, methoxychlor, methyl parathion, mevinphos, naled, oxamyl, oxythioquniox, parathion, permethrin, phorate, phosmet, profenofos, propargite, sulprofos, thiodicarb, and trichlorfon.

[0062] Fertilizers can be organic, or inorganic. They can be naturally occurring compounds such as peat or mineral deposits, manufactured through natural processes such as composting, or manufactured through chemical processes. Thus, the term “fertilizer” as used herein, refers to any substance which, when applied to a substrate, e.g., soil, leaves, hydroponic solution etc., enriches or fertilizes that substrate by providing nutrients for the plant’s, necessary biological functions, e.g., growth, flowering etc. In an exemplary embodiment, a fertilizer comprises plant nutrients in the form of agricultural waste products, e.g., manure, grass clippings, compost. In another exemplary embodiment, a fertilizer comprises a synthetic blend of various chemical substances known in the art as plant nutrients, e.g., blends comprising at least one or more of nitrogen, potassium, and / or phosphorus. In yet other exemplary embodiments, a fertilizer comprises a combination of agricultural waste products and synthetic chemicals which, when applied to a substrate, enriches, or fertilizes that substrate. Fertilizers may contain sources of macronutrients (nitrogen, phosphorous, and potassium), secondary macronutrients (calcium (Ca), magnesium (Mg) and sulfur (S)), and micronutrients (boron (B), copper (Cu), iron (Fe), manganese (Mn), molybdenum (Mo) and zinc (Zn)).

[0063] Hormones, growth stimulants and the like include, but are not limited to: trinexepac-ethyl, gibberellic acid, gibberellins, cytokinins, benzyladenine, glycines, quinolenes, phosphoric acid compounds, organic carbamates, quaternary ammonium compounds, acetamides, ethychlozate, azoles, paclobutrazol, anilides, pyradazidine, pyrimidines, napthaleneacetamide, phthalmides, phenoxies, pyrimidines, biostimulants, seaweed extracts, phthalmides, phenoxies, steroids (e.g., brassinosteroids) and organic or carboxylic acids (e.g. gamma amino butyric acid and L-glutamic acid, Napthalene acetic acid, Clofencoet, Sintofen, nicotinic acids).

[0064] Other pesticides, protectants and / or beneficial agents which may find use in the compositions disclosed herein include, animal and bird repellants, bitter flavors, irritants, and malodorous ingredients, molluscicides (e.g., slugs and snails), rodenticides, chemosterilants, plant defense boosters (Harpin protein and Chitosan), frost prevention aids, UV protectants, antioxidants, moisture retention aids, humic acids and humates, and lignins and lignates.

[0065] The compositions may further comprise one or more surfactants. Surfactants include ethoxylated fatty amines, alkylphenol ethoxylate-based surfactants, alcohol ethoxylate-based surfactants, silicone -based surfactants, oils (e.g., petroleum, vegetable, or seed oils). Surfactantswhich can be used in the preparation of the herbicidal compositions disclosed herein include those described in “McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood, N.J., 1981, Stache, H., “Tensid-Taschenbuch” [Surfactant Handbook], Carl Hanser Verlag, Munich / Vienna, 1981 and M. and J. Ash. “Encyclopedia of Surfactants,” Vol I-III, Chemical Publishing Co., New York, 1980-81.

[0066] In some embodiments, the compositions further comprise a nonionic surfactant, an anionic surfactant, cationic surfactant, and / or a zwitterionic surfactant. Exemplary nonionic surfactants include without limitation: Cetomacrogol 1000; cetostearyl alcohol; cetyl alcohol; cocamide diethanolamine; cocamide monoethanolamine; decyl glucoside; decyl polyglucose; glycerol monostearate; IGEPAL CA-630; Isoceteth-20; lauryl glucoside; maltoside; monolaurin; mycosubtilin; narrow-range ethoxylate; Nonidet P-40; Nonoxynol-9; Nonoxynols; NP-40; octaethylene glycol monododecyl ether; N-octyl beta-D-thioglucopyranoside; octyl glucoside; oleyl alcohol; pentaethylene glycol monododecyl ether; polidocanol; poloxamer; poloxamer 407; polyethoxylated tallow amine; polyglycerol polyricinoleate; polysorbate; polysorbate 20; polysorbate 80; sorbitan; sorbitan monolaurate; sorbitan monostearate; sorbitan tristearate; stearyl alcohol; surfactin; Triton X- 100; and Tween 80. Exemplary anionic surfactants include without limitation: 2- acrylamido-2-methylpropane sulfonic acid; alkylbenzene sulfonates; ammonium lauryl sulfate; ammonium perfluorononanoate; chlorosulfolipid; disodium cocoamphodiacetate; docusate; magnesium laureth sulfate; MBAS assay; A-Olefin sulfonate; perfluorobutanesulfonic acid; perfluorodecanoic acid; perfluorohexanesulfonic acid; perfluorononanoic acid; perfluorooctanesulfonic acid; perfluorooctanoic acid; phospholipid; potassium lauryl sulfate; soap; soap substitute; sodium dodecyl sulfate; sodium laurate; sodium laureth sulfate; sodium lauroyl sarcosinate; sodium myreth sulfate; sodium nonanoyloxybenzenesulfonate; sodium pareth sulfate; sodium stearate; sodium sulfosuccinate esters; sodium tetradecyl sulfate; and sulfolipid. Exemplary zwitterionic surfactants include without limitation: CHAPS detergent; cocamidopropyl betaine; cocamidopropyl hydroxysultaine; dipalmitoylphosphatidylcholine; hydroxysultaine; miltefosine; peptitergents; and sodium lauroamphoacetate.

[0067] The compositions are not limited by the type of solvent. Exemplary solvents include, but are not limited to: water; monoethylene glycol; diethylene glycol; propylene glycol or the methyl, ethyl, n-propyl, n-butyl or t-butyl ethers thereof; dipropylene glycol or the methyl, ethyl, n-propyl, n- butyl, or t-butyl ethers thereof; tripropylamine glycol or the methyl, ethyl, n-propyl, n-butyl, or t- butyl ethers thereof; 1,3 butanediol; 1,4 butanediol; 2-methy 1,1, 3 -propanediol; 2,2-methyl-l,3- propanediol; 2-methyl-l,3-pentanediol; 2-methyl-2,4-pentanediol; glycerol; and sorbitol.3. Methods

[0068] The disclosure also provides methods for controlling undesired plant growth. In some embodiments, the undesired plant growth is in a soil or growing media and the methods comprise applying an effective amount of a composition as disclosed herein to the soil or growing media. In some embodiments, the methods comprise applying an effective amount of a composition as disclosed herein to the undesired plant. The phrase “effective amount” means an amount necessary to reduce or inhibit undesired plant growth; increase plant necrosis or plant death, inhibit plant reproduction; or otherwise diminish the occurrence and activity of the undesired plant.

[0069] A variety of undesired plants can be treated and controlled by the methods disclosed herein, and as such the methods are not limited to the type of undesired plant. In some embodiments, the undesired plant is a broadleaf weed, a grass or grassy weed, a sedge, or a combination thereof.

[0070] The compositions of the present invention are suitable for controlling a large number of broadleaf weeds. Broadleaf weeds include but are not limited to: Amaranths (e.g., waterhemp, Palmer amaranth, spiny amaranth, smooth pigweed, redroot pigweed), momingglory (e.g. smallflower, entireleaf, ivyleaf, pitted, red / scarlet, tall, cypressvine, purple moonflower, palmleaf), wild buckwheat, buffalobur, common cocklebur, kochia, common lambsquarters, marshelder, wild mustard, nightshade (e.g. black, eastern black, hairy, horsenettle), croton, eclipta, Galinsoga species, prickly sida, bristly starbur, Florida pusley, hemp, sesbania, sicklepod, Pennsylvania Smartweed, common and giant ragweed, smartweed, wild sunflower, waterhemp (e.g., tall, common), wild watermelon, spurge (e.g., prostrate, spotted), mallow, witchweed, yellow rocket, wild cucumber, ground cherry, jimsonweed, ladysthumb, redweed, anoda, copperleaf (e.g., hophornbeam, Virginia), thistle, dandelion, clover, chickweed, curly dock, velvetleaf, common purslane, wild poinsettia, smellmelon, balloonvine, carpetweed, showy crotalaria, mexicanweed, and the like.

[0071] The compositions of the present invention are also suitable for controlling a large number of grasses or grassy weeds, such as bamyardgrass, crabgrass, green foxtail, giant foxtail, yellow foxtail, johnsongrass, wild oats, annual bluegrass, annual ryegrass, bermudagrass, carpetgrass, creeping bentgrass, blackgrass, goosegrass, signalgrass, panicum, and the like.

[0072] The compositions of the present invention are also suitable for controlling a large number of annual and perennial sedge weeds including cyperus species such as purple nutsedge, yellow nutsedge, hime-kugu, sedge weed, rice flatsedge, and the like.

[0073] In some embodiments, a desired plant or crop resides in the soil or growth medium or is comingled with the undesired plant. The methods and compositions disclosed herein are suitable for use with a wide variety of desired plants or crops such as, grain crops, fruit crops, forage crops, rootvegetable crops, leafy vegetable crops, flowering plants, conifers, trees, oil crops, plants used in phytoremediation, industrial crops, medicinal crops, laboratory model plants, and the like. As such, non-limiting examples of desired plants or crops that may be used with the present methods include: legumes (e.g., soybeans, dry beans, snap beans, groundnuts, peas, peanuts), cotton, potatoes, sweet potatoes, small grains (e.g., wheat, barley, rye), com, peppers, pumpkins and squash, rice, tomatoes, melons (e.g., watermelon, cantaloupe and other musk melons) cucumbers, eggplants, and sorghum.

[0074] Application can be done before, during and / or after emergence of the undesirable plants. In some embodiments, the compositions described herein are applied prior to undesired plant emergence. For example, application of the composition precedes the weeds sprouting through the soil surface. In some embodiments, the application may be prior to germination of the undesired plant. In some embodiments, the compositions described herein are applied after undesired plant emergence. Post-emergence applications include any time when the undesired plant is visibly growing and spreading, preferably when the plants are young and actively growing.

[0075] When the compositions disclosed herein are used in crops, they can be applied after seeding and before or after the emergence of the crop plants. The compositions can also be applied prior to seeding of the crop plants. In some embodiments, the compositions are applied postemergence, after the emergence of the crop and / or the undesirable plants.

[0076] As used herein, the term “applying” in reference to the compositions disclosed herein, refers to any means for treating growth medium and undesired plants or plant parts with the composition, for example, irrigating, spraying, and the like. In some embodiments, the applying comprises irrigating, spraying, foliar spraying, or a combination thereof. The application may be performed once or at multiple time points (e.g., pre- or post-emergence of the undesired plant, pre- or post-planting of the desired crop or plant).

[0077] Irrigation systems and methods that deliver water, often containing plant nutrients and other agents, to plants via networks of irrigation pipes or hoses are very well known, in a process sometimes referred to as chemigation or fertigation. In many such irrigation systems and networks, solution from the pipes or hoses is delivered to the plants by emitters or drippers that are installed on or integrated in the irrigation pipes or hoses. In the methods herein, the compositions disclosed herein, may be added directly to water irrigation solutions, continuously or in bolus amounts at distinct times, or be delivered separately by similar irrigation methods as desired.

[0078] Spraying may be directed towards any part of the undesired plant including the foliage, base of the stems, branches, roots, spraying onto the surface of soil, or spraying at the base of the plants by any industrial or home use methods. The compositions disclosed herein may be applied by spraying methods commonly employed, such as conventional high-gallonage hydraulic sprays, low-gallonage sprays, air-blast, aerial sprays, and dusts. The methods may alternatively employ electrodynamic spraying techniques or other low volume methods or application by land or aerial irrigation systems.

[0079] In some embodiments, the applying comprises adding the compositions to a plant growth medium including liquid or dry in- furrow application, spraying across the area of soil in which a desired plant or crop will be seeded or planted, direct incorporation into soils or other plant growth media, or application of granular formulations or granules.

[0080] Application of the compositions disclosed herein to soil-based growth mediums may take many forms. The compositions can be applied on the top of the soil, for example, as a liquid or granular formulation. Alternatively, soil incorporation is a method of application which physically mixes the compositions in the soil layer, particularly where it is most efficacious for inclusion (e.g., top two to three inches of soil or rhizosphere) rather than applying to the soil surface or placing in furrow.

[0081] In some embodiments, the compositions are applied in rotation with other treatments. In some embodiments, the compositions are applied to the undesired plants at the same time as the other treatments for the soil, undesired plants, and / or desired crops or plants.

[0082] The rate of application may vary within wide limits and depends on the nature of the growth medium or soil, the method of application, the crop plant, the undesired plant to be controlled, the climate or weather conditions, and other factors governed by the method of application and the time of application.

[0083] The compositions disclosed herein can generally be applied at a rate of about 0.5 pt per acre to about 4 pt per acre. In some embodiments, the compositions are applied at a rate of 0.5 to 2 pt per acre (e.g., about 0.5 pt / A, about 0.75 pt / A, about 1.0 pt / A, about 1.25 pt / A, about 1.5 pt / A, about 1.75 pt / A, or about 2.0 pt / A).

[0084] The composition disclosed can generally be applied at about 0. 15 to 0.4 pound active ingredient per acre (pound ai / A). In some embodiments, the compositions are applied at about 0.15 lb ai / A, about 0.16 lb ai / A, about 0.17 lb ai / A, about 0.18 lb ai / A, about 0.19 lb ai / A, about 0.2 lb ai / A, about 0.21 lb ai / A, about 0.22 lb ai / A, about 0.225 lb ai / A, about 0.23 lb ai / A, about 0.27 lb ai / A, about 0.25 lb ai / A, about 0.26 lb ai / A, about 0.27 lb ai / A, about 0.275 lb ai / A, about 0.28 lb ai / A, about 0.29 lb ai / A, about 0.3 lb ai / A, about 0.31 lb ai / A, about 0.32 lb ai / A, about 0.325 lb ai / A, about 0.33 lb ai / A, about 0.34 lb ai / A, about 0.35 lb ai / A, about 0.36 lb ai / A, about 0.37 lb ai / A, about 0.375 lb ai / A, about 0.38 lb ai / A, about 0.39 lb ai / A, or about 0.4 lb ai / A. In select embodiments, the compositions are applied at about 0.1875 to 0.375 lb

[0085] The combination of PPO inhibitors (e.g., fomesafen)and ethoxylated lecithin in the disclosed compositions can provide enhanced control of undesired plants, as compared to a corresponding treatment using either a PPO inhibitor or ethoxylated lecithin alone. In some embodiments, the combination of PPO inhibitors and ethoxylated lecithin in the disclosed compositions increases the control of the undesired plants over treatment using either a PPO inhibitor or ethoxylated lecithin alone. For example, the compositions disclosed herein increase control of the undesired plant at least 1.2 fold (e.g., at least 1.3 fold, at least 1.4 fold, at least 1.5 fold, at least 1.6 fold, at least 1.7 fold, at least 1.8 fold, at least 1.9 fold, at least 2 fold, or more) over treatments using either a PPO inhibitor (e.g., fomesafen) or ethoxylated lecithin alone. In some embodiments, the disclosed compositions decrease undesired plant biomass by at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, or more as compared to treatments using either a PPO inhibitor (e.g., fomesafen) or ethoxylated lecithin alone. In some embodiments, the disclosed compositions decrease undesired plant survival by at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, or more as compared to treatments using either a PPO inhibitor (e.g., fomesafen) or ethoxylated lecithin alone. In some embodiments, the combination of PPO inhibitors and ethoxylated lecithin in the disclosed compositions increases the control of the undesired plants over treatment using a PPO inhibitor with other industry standard surfactant packages, e.g., ethoxylates.Kits

[0086] In another aspect, the disclosure provides kits comprising a composition as described herein or individual components of the composition as described herein. The kits can also comprise other agents and / or products co-packaged, co-formulated, and / or co-delivered with other components.

[0087] The kits can also comprise instructions for using the components of the kit. The instructions are relevant materials or methodologies pertaining to the kit. The materials may include any combination of the following: background information, list of components, brief or detailed protocols for using the compositions, troubleshooting, references, technical support, and any other related documents. Instructions can be supplied with the kit or as a separate member component, either as a paper form or an electronic form which may be supplied on computer readable memory device or downloaded from an internet website, or as recorded presentation.

[0088] It is understood that the disclosed kits can be employed in connection with the disclosed methods. The kit may further contain containers or devices for use with the methods or compositions disclosed herein. For example, the disclosed kit may further provide a means to apply thecomposition (e.g., a sprayer or spray bottle, etc.) or means to measure and mix the components of the composition (e.g., bottles, flasks, containers, pipettes, graduated cylinders, etc.).

[0089] The kits provided herein are in suitable packaging. Suitable packaging includes, but is not limited to, vials, bottles, jars, flexible packaging, and the like. Individual member components of the kits may be physically packaged together or separately.4. ExamplesExample 1 In-Can Fomesafen Bioefficacy Study

[0090] The effects of a fomesafen formulation containing ethoxylated lecithin (EXT 1490) were compared to an identical fomesafen formulation not containing ethoxylated lecithin (EXT 1492), an identical formulation blank with no fomesafen (EXT 1491), Reflex (a commercially available fomesafen formulation) and a mixture of Reflex plus an adjuvant formulation containing ethoxylated lecithin (SURFLEX L 1000 MC).

[0091] Kochia (Bassia scoparia) was grown in 1 L pots filled with Fertilome professional potting mix. Seeds were allowed to germinate under artificial light 13: 11 h L:D photoperiod at 25 °C. Plants were thinned to 1 plant per pot after emergence. Plants were watered as needed. The plants were treated when they reached an average height of 1.5 inches. The applications were made using a DeVries research track sprayer with DG9502 EVS nozzles situated 0.5 meters above the plant canopy. The sprayer carrier volume was 15 gallons per acre, applied at 55 psi and a boom speed of 3 mph. The plants were evaluated at 7 and 14 days after treatment for visual percent weed control, based on an estimate of volume reduction vs. the untreated control, and aboveground plant biomass was measured when the study was terminated at 14 days after treatment.*EL is ethoxylated lecithin

[0092] Treatment with EXT 1490 (fomesafen formulation containing ethoxylated lecithin) resulted in significantly better Kochia control and biomass reduction compared to Reflex, and EXT1490 (fomesafen formulation containing ethoxylated lecithin) provided more kochia control than EXT 1492 (fomesafen formulation without ethoxylated lecithin) (FIGS. 1A-1C).Example 2 In-Can Fomesafen and Adjuvant Bioefficacy Study

[0093] The effects of a fomesafen formulation containing ethoxylated lecithin (EXT 1490) were compared to an identical fomesafen formulation not containing ethoxylated lecithin (EXT 1492), Reflex (a commercially available fomesafen formulation) and mixtures of Reflex plus two different adjuvant formulations containing ethoxylated lecithin (SYNTHEX L 941 and SURFLEX L 1000 MC).

[0094] Kochia (Bassia scoparia) and Waterhemp (Amaranthus tuberculatus) were grown in 1 L pots filled with Fertilome professional potting mix. Seeds were allowed to germinate under artificial light 13: 11 h L:D photoperiod at 25 °C. Plants were thinned to 1 plant per pot after emergence.Plants were watered as needed. The plants were treated when they reached an average height of 1.5 inches. The applications were made using a DeVries research track sprayer with DG9502 EVS nozzles situated 0.5 meters above the plant canopy. The sprayer carrier volume was 15 gallons per acre, applied at 55 psi and a boom speed of 3 mph. The plants were evaluated at 7 and 14 days after treatment for visual percent weed control, based on an estimate of volume reduction vs. the untreated control, and aboveground plant biomass was measured when the study was terminated at 14 days after treatment.*EL is ethoxylated lecithin

[0095] All treatments containing ethoxylated lecithin - EXT 1490, Reflex + SYNTHEX L 941, and Reflex + SURFLEX L 1000 MC - resulted in significantly better kochia control and greater reduction of kochia biomass at 7 days after treatment relative to Reflex alone (FIGS. 2A and 2B).

[0096] All treatments containing ethoxylated lecithin - EXT 1490, Reflex + SYNTHEX L 941, and Reflex + SURFLEX L 1000 MC - resulted in significantly better waterhemp control at 7 daysafter treatment, and EXT 1490 and Reflex + SYNTHEX L 941 significantly reduced waterhemp biomass relative to Reflex alone (FIGS. 3A and 3B).Example 3 Fomesafen Dose Response

[0097] The effects of a fomesafen formulation containing ethoxylated lecithin (EXT 1490) were compared to Reflex (a commercially available fomesafen formulation) in a dose response study with a range of use-rates.

[0098] Waterhemp seeds were planted in potting mix contained in trays and, at the two true leaves, transplanted into 656 ml pots filled with potting mix. Plants were maintained in the greenhouse at 68 to 104 °F (20-40 °C) with a natural ventilation system. Natural lighting was supplemented with 400 watts high-pressure sodium light bulbs simulating a 16 h photoperiod. Plants were watered daily and fertigated weekly with 20-10-20 water-soluble fertilizer delivering 300 ppm of N and K, respectively, and 150 ppm of P. The dose-response experiment was organized in complete randomized design (CRD), with six replications, and a single experimental run. Doses ranged from 1 / 16 to 4x the label rate of reflex and EXT1490 (lx: 1 pt / a). Treatments were sprayed when plants reached 2 to 3 inches in height using a single-nozzle research track spray chamber equipped with a DG9502EVS (medium droplet size at 40 PSI) nozzle and the spray carrier volume was 15 gallons per acre. Visual estimation of weed control was evaluated at 7, 14, and 21 days after treatment. Aboveground biomass was measured at the conclusion of the study - 21 days after treatment. At each rating date, regressions were fitted to the data to determine the ED50 (dose of fomesafen that resulted in 50% control, survival, and biomass accumulation).*EL is ethoxylated lecithin

[0099] EXT 1490 exhibited a significantly lower ED50 compared to Reflex for waterhemp control (42% lower), plant survival (49% lower), and biomass (30% lower) at 21 days after treatment.Example 4Absorption, Protoporphyrin Accumulation, and Reactive Oxygen Species (ROS) Formation

[0100] There is a strong relationship between herbicide absorption, protoporphyrin accumulation, reactive oxygen species (ROS) formation, lipid peroxidation, and the overall efficacy of PPO herbicides. To test the efficacy of fomesafen, technical grade fomesafen (Chemservice; West Chester, PA) was utilized in the formulations below.

[0101] Common waterhemp (Amaranthus tuberculatus) (biotype A90 susceptible to PPO herbicides) was grown in potting soil (Lambert, LM-GPS seedling mix) in the greenhouse under controlled environment conditions of 25 °C and 75% relative humidity until plants were at the third true-leaf stage (2 to 2.5 inches tall).

[0102] Droplet interaction on leaf surfaces

[0103] The effect of the adjuvants on the interaction between the droplets and leaf surfaces was investigated by applying 5 pL drop on the adaxial side of waterhemp leaves, capturing an image with a camera, and observing the shape, spread, and curvature of the droplets (FIG. 4). Reflex (Syngenta), a commercially available fomesafen formulation, showed the least interaction with the leaf surface had the worst interaction, whereas ethoxylated lecithin and the surfactants increased the interaction as most easily seen in the images by a decrease in the contact angle between the leaf and droplet.

[0104] Efficacy

[0105] Waterhemp seedlings were sprayed with the formulations described previously at doses ranging from 0.052-3.33 % v / v (0.0625-4 pt / a) at 15 gal / a using TEEJET DG 9502 EVS with a single nozzle overhead track sprayer (Generation III Research Sprayer: DeVries, Hollandale, MN, USA).*EXT 1649 contains EL (ethoxylated lecithin)

[0106] Pressure was set at 40 psi and the spray nozzle was 40 cm above the canopy and moved at a speed of 2.41 mph. Herbicide application was completed during a time period with anticipated clear days to ensure good light activation of fomesafen. Efficacy was evaluated at various timepoints after application by measuring fresh weight, percent injury, and survival.

[0107] Data for efficacy 21 days after treatment is shown in FIGS. 5A-5C.Fomesafen (Reflex) alone had lower efficacy as measured by all three metrics. Fomesafen applied in combination with ethoxylated lecithin (EXT 1649) consistently outperformed Reflex and formulations comprisingindustry standard surfactants (EXT 1650 and EXT 1651), which provided some beneficial increase in efficiency as compared to fomesafen alone.

[0108] All treatments imparted bumdown injuries to waterhemp 5 days after treatment. Reflex alone was slightly less active with some meristematic tissues surviving the treatment (FIG. 6A), whereas formulations comprising ethoxylated lecithin (FIG. 6B) or an industry standard surfactant (FIGS. 6C-6D) caused similar levels of injury.

[0109] Fomesafen Absorption

[0110] Separately from the efficacy measurements described above, the absorption of fomesafen was evaluated at 6, 24, and 48 hours after application (HAT). Plants were sprayed at recommended field rate (0.83% v / v fomesafen and 0.075 %v / v ethoxylated lecithin or surfactant package, equivalent to or 1 pt / a) and kept in low light intensity to optimize absorption and avoid rapid desiccation of the leaf tissues, which would alter absorption over time. Treated leaves (1 g) were weighed and washed with 15 mL of 50% acetone in a beaker, padded dry, placed in 50 mL tube and stored at -80C until extracted. Leaves were homogenized using the QuEChERS method (10 mL water and 10 mL acetonitrile with 1% formic acid) and samples were centrifuged at 5,000 g. Organic fractions were collected, filtered through 0.2 pm nylon filters and injected in LC-MSMS. The LC- MSMS was optimized for detection of fomesafen and its fragments by multiple reaction monitoring (MRM). A calibration curve was established to quantify fomesafen. LOD and LOQ were determined prior to analysis of plant samples.

[0111] As shown in FIG. 7, both the addition of ethoxylated lecithin (+49) and the two surfactants (+50 and +51) increased the absorption of fomesafen by more than 3 -fold after 12 hours. The increased efficacy described above may be a result of increased absorption.

[0112] Protoporphyrin accumulation

[0113] Injury caused by PPG inhibiting herbicides is known to be proportional to the accumulation of protoporphyrin and the subsequent generation of reactive oxygen species. The effects of fomesafen formulation on protoporphyrin levels were measured in plants treated with fomesafen and the adjuvant packages described above. Samples were collected at 3, 6, 9, 12 and 24 h after application. Protoporphyrin extraction and analysis followed a protocol described by Dayan et al. (Weed Sci. 2015, 63 (spl), 23-63). Approximately 0.3 g of leaf tissue was weighed and stored in falcon tubes at -80 C. To extract porphyrin, frozen leaves were ground to a powder under liquid nitrogen and homogenized in 2 mL of extraction solvent (mcthanokO. I M NH4OH, 9: 1) and centrifuged at 10,000 x g for 15 min. The supernatant was saved, and the pellet was re-homogenized in 1 mL of extraction solvent, centrifuged again at 10,000 x g for 15 min. Supernatants were pooled and then filtered through a 0.2-pm nylon syringe membrane filter before quantification with the LC-MS / MS system. Protoporphyrin was separated in a biphenyl column (100 by 4.6 mm, 2.6 pm, 40 °C) at a flow rate of 0.4 mL min1using a linear gradient of methanol (B) and 10 mM ammonium acetate (A): 0 min, 50% B; 8 min, 70% B; 11 min, 90% B; 13 min, 90% B; 13.5 min, 50% B; 17 min, 50% B. The MRM was optimized to 340.10 > 227.95. A standard curve generated with serial dilutions of technical grade protoporphyrin IX (MilliporeSigma, St. Louis, MO) was used for quantification.

[0114] The efficacy of fomesafen applied alone or in combination with ethoxylated lecithin (EXT 1649), or a surfactant (EXT 1650 or EXT 1651) was consistent with the level of protoporphyrin accumulation in treated waterhemp (FIG. 8).

[0115] Electrolyte leakage

[0116] The efficacy of PPO herbicides can also be assessed by measuring electrolyte leakage from cotyledon discs given that injury caused this type of herbicide results in the generation of reactive oxygen species. Leaf discs of waterhemp were floated on solutions of fomesafen with the formulations described above. Electrolyte leakage was measured using a modified method of Dayan and Watson (Pestic. Biochem. Physiol. 2011, 101 (3), 182-190). For each formulation, 36 discs (6 mm diam.) were cut from waterhemp seedlings at their 3rdtrue-leaf stage and placed in a petri dish. The discs were floated over 5 mL of 1 mM MES buffer (pH 6.5) with 2% sucrose with the fomesafen formulation in low light intensity to prevent photodynamic damage (less than 150 pmol m’2s"1). The initial conductivity (a measure of electrolyte leakage) was measured using a FiveEasy Plus FP30 conductivity meter connected to an InLab 751-4 mm microprobe (Mettler Toledo, Columbus, OH 43240). The plates were kept in a Percival LED-30L1 LED high intensity growth chamber (Percival, Perry Iowa 50220). Conductivity was measured 1, 3, 6, 9, 12 and 24 h after exposure to light intensity (approx. 1,050 pmol m’2s’1).

[0117] Ethoxylated lecithin and the surfactants were tested at a rate of 0.1% v / v. The formulations comprising the surfactants (EXT 1650 and EXT 1651) resulted in maximum electrolyte leakage, while EXT 1649 remained at levels slightly higher than fomesafen alone (FIG. 9). This finding, when combined with the protoporphyrin accumulation and fomesafen absorption assays, suggests that ethoxylated lecithin tank-mixed with fomesafen resulted in lower damage to cellular membranes than the EXT 1650 and EXT 1651, allowing the herbicide to penetrate through and reach the site of action.

[0118] Reactive oxygen species accumulation

[0119] PPO herbicides utilize light-dependent generation of reactive oxygen species (ROS) due to photoexcitation of protoporphyrin accumulation to effectively kill the plant. ROS was measured in leaves exposed to the fomesafen formulations described above. H2O2 was measured using the DAB method. Briefly, leaves were stained in solutions containing 3,3'-diaminobendizine (DAB) and nitroblue tetrazolium chloride (NBT), respectively. ROS levels were quantified using CS3 Photoshop (Adobe Systems, San Jose, CA, USA), measuring the color intensity in each leaf disc, removing background levels. Data was represented as relative intensity of treated samples compared to control samples (treated intensity-control intensity).

[0120] The amount of reactive oxygen species generated by fomesafen was increased by the ethoxylated lecithin (49) and surfactants (50 or 51) (FIG. 10), consistent with the observed increase in absorption and protoporphyrin accumulation.

[0121] Lipid peroxidation

[0122] The quantification of malonaldehyde (MDA) was conducted to measure lipid peroxidation due to ROS accumulation for all treatments. Samples from were collected at 24 h after application with fomesafen (0.83 %v / v) alone and fomesafen (0.83 %v / v) + EXT 1649, EXT 1650 and EXT 1651 at 1 %v / v, respectively. Plant tissue was homogenized with 3 mL of 80:20 (v:v) ethanol: water. A 2 mL aliquot of the solution was transferred to a tube containing 1 mL of 20% (w / v) trichloroacetic acid and 0.65% (w / v) 2-thiobarbituric acid. Samples were mixed for 30 s, heat at 95oC for 30 minutes, cooled in ice for 5 min, and centrifuged at 5000 g for 10 min. Absorbance was measured at 532 nm [A532] and 600 nm [A600] and MDA was calculated as follows: MDA =* 106. The amount of lipid peroxidation was greater in plants treated with fomesafen + ethoxylated lecithin (EXT 1649) (FIG 12).

[0123] It is understood that the foregoing detailed description and accompanying examples are merely illustrative and are not to be taken as limitations upon the scope of the disclosure, which is defined solely by the appended claims and their equivalents.

[0124] Various changes and modifications to the disclosed embodiments will be apparent to those skilled in the art and may be made without departing from the spirit and scope thereof.

Claims

CLAIMSWhat is claimed is:

1. An herbicidal composition comprising: a protoporphyrinogen oxidase (PPO) inhibitor, or an agriculturally acceptable salt thereof; and ethoxylated lecithin.

2. The herbicidal composition of claim 1, wherein the composition comprises about 0.01% v / v to about 30.0% v / v PPO inhibitor, or an agriculturally acceptable salt thereof.

3. The herbicidal composition of claim 1 or 2, wherein the composition comprises about 0.01% v / v to about 5.0% v / v PPO inhibitor, or an agriculturally acceptable salt thereof.

4. The herbicidal composition of claim 3, wherein the composition comprises about 0.05% v / v to about 4.0% v / v PPO inhibitor, or an agriculturally acceptable salt thereof.

5. The herbicidal composition of claim 1 or 2, wherein the composition comprises about 10.0% v / v to about 30.0% v / v PPO inhibitor, or an agriculturally acceptable salt thereof.

6. The herbicidal composition of claim 5, wherein the composition comprises about 20.0% v / v to about 30.0% v / v PPO inhibitor, or an agriculturally acceptable salt thereof.

7. The herbicidal composition of any of claims 1-6, wherein the composition comprises about 0.001% v / v to about 20.0% v / v ethoxylated lecithin.

8. The herbicidal composition of any of claims 1-7, wherein the composition comprises about 0.001% v / v to about 0.5% v / v ethoxylated lecithin.

9. The herbicidal composition of claim 8, wherein the composition comprises about 0.01% v / v to about 0.2% v / v ethoxylated lecithin.

10. The herbicidal composition of any of claims 1-7, wherein the composition comprises about 5% v / v to about 20% v / v ethoxylated lecithin.

11. The herbicidal composition of claim 10, wherein the composition comprises about 5% v / v to about 10% v / v ethoxylated lecithin.

12. The herbicidal composition of any of claims 1-11, wherein the PPO inhibitor is fomesafen.

13. The herbicidal composition of any of claims 1-12, wherein the composition further comprises a pesticide, fertilizer, additional herbicide, or a combination thereof.

14. The herbicidal composition of any of claims 1-13, wherein the composition further comprises a surfactant.

15. A method for controlling undesired plant growth in a soil or growth medium comprising applying an effective amount of a composition of any of claims 1-14 to the soil or growth medium.

16. A method of controlling undesired plant growth comprising applying an effective amount of a composition of any of claims 1-15 to the undesired plant.

17. The method of claim 15 or 16, wherein the applying comprises irrigating (chemigation), spraying, in- furrow application, or direct incorporation into the soil or growth medium.

18. The method of any of claims 15-17, wherein the applying is prior to undesired plant emergence.

19. The method of any of claims 15-17, wherein the applying is after emergence of the undesired plant.

20. The method of any of claims 16-19, wherein the method increases uptake and / or penetration of the protoporphyrinogen oxidase (PPO) inhibitor in the undesired plant.

21. The method of any of claims 15-20, wherein the undesired plant is a broadleaf weed, a grass or grassy weed, a sedge, or a combination thereof.

22. The method of any of claims 15-221, wherein a desired plant or crop resides in the soil or growth medium or is comingled with the undesired plant.

23. The method of claim 22, wherein the desired plant or crop is beans, groundnuts, cotton, or potatoes.

24. The method of claim 22 or 23, wherein the applying is prior to planting of the desired plant or crop.

25. Use of a composition of any of claims 1-15 in controlling undesired plant growth.

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