Adjuvant composition for enhancing herbicide efficacy in soil

WO2025114935A3PCT designated stage expired Publication Date: 2025-07-24OXITENO S A IND E COMERCIO
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Patent Information

Application Number
PCT/IB2024/061966
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2023-11-29
Filing Date
2024-11-27
Publication Date
2025-07-24

AI Technical Summary

Technical Problem

Existing adjuvants used with herbicides face challenges such as tank mix compatibility issues, phytotoxic effects on crops, residual effects on soil and crops, and variable performance across different environmental and agronomic conditions, which affect herbicide efficacy and weed control.

Method used

The development of an herbicide formulation that includes an herbicidally effective amount of an herbicide substantially free of phosphorous atoms, combined with an adjuvant composition comprising a non-copolymer base ingredient and an amphoteric surfactant with a specific general formula, which enhances the residual activity of the herbicide in soil and reduces phytotoxicity to crops.

Benefits of technology

The proposed solution significantly enhances the residual activity of the herbicide in soil, maintaining effective weed control for an extended period without causing significant phytotoxicity to crops, thus improving the overall efficacy and sustainability of weed management practices.

✦ Generated by Eureka AI based on patent content.

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Abstract

Herbicide formulations, adjuvant compositions, and adjuvants that enhance the efficacy of an herbicide as well as systems and methods of making and using thereof may enhance the residual activity of herbicides to control weeds at lower doses than other adjuvants without causing phytotoxicity in the crop of interest or harming its sprouting. In some cases, adjuvants may have excellent physiochemical characteristics, affording compatibility with an herbicide. The adjuvant or adjuvant composition including the adjuvant can work on different types of soil.
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Description

ADJUVANT COMPOSITION FOR ENHANCING HERBICIDE EFFICACY IN SOILCROSS REFERECNE TO RELATED APPLICATIONS

[0001] This application claims priority to U.S. Provisional Application No. 63 / 603,871, entitled “Surfom CS 8889 As A Tankmix Adjuvant To Increase S-Metolachlor Pre-Emergent Herbicide Residue In Soil,” filed November 29, 2023, the entire contents of which is incorporated by reference herein.TECHNICAL FIELD

[0002] The present disclosure generally relates to agrochemical adjuvants.BACKGROUND

[0003] Herbicides may include substances or methods used to control or eliminate unwanted vegetation, such as weeds. They may play a crucial role in modern agriculture by targeting specific weeds or broad-spectrum vegetation, thereby reducing competition for water, nutrients, and sunlight with cultivated crops. By controlling weeds, herbicides may help protect crop yields and maintain agricultural productivity. Additionally, while many herbicides are chemical substances formulated for weed control, alternatives exist. These can include organic herbicides derived from natural sources like plant oils or microbial agents, as well as physical methods such as mulching or flame weeding. Effective herbicide use can reduce the need for mechanical cultivation, conserving soil moisture and minimizing soil erosion.

[0004] Adjuvants are additives that may be formulated to enhance the effectiveness and performance of herbicides and other agricultural chemicals. They may serve various crucial roles in herbicide applications. Adjuvants can improve herbicide performance in several ways. In post-emergent applications, they can increase spray coverage, improve adhesion to plant surfaces, and facilitate penetration into plant cuticles. In pre-emergent applications, adjuvants can help the herbicide overcome the mulch barrier on the soil, improve soil penetration, and aid in herbicide retention, reducing leaching. Additionally, adjuvants can help the herbicide reach the seeds, providing better control of weed germination. The goal is to ensure more effective weed control and optimal use of the active ingredient. Many adjuvants may act as surfactants, reducing surface tension and allowing herbicide solutions to spread more evenly across plant surfaces, straw, soil, and seed, thus improving overall coverage and absorption. Additionally, adjuvants may help mitigate the effects ofenvironmental factors such as temperature, humidity, and soil conditions, which can impact herbicide effectiveness.

[0005] In agricultural practices, herbicides and adjuvants may be combined in a tank mix for application. The compatibility between adjuvant and herbicide may be critical for ensuring efficacy and safety. Compatibility issues between the adjuvant and the specific formulation of herbicide can lead to chemical reactions, precipitation, or reduced effectiveness of both the herbicide and adjuvant. Manufacturers may adjust adjuvant formulations to enhance compatibility with a wide range of herbicides, ensuring stability and efficacy in tank mixes. Properly formulated adjuvants may improve the sprayability and coverage of herbicides, optimizing their performance and minimizing waste.

[0006] Recent advancements in adjuvant technology have led to a diverse range of formulations tailored to specific herbicide applications. Adjuvants may come in various forms, including surfactants, oils, spreaders, stickers, and penetrants, each designed to address specific challenges in herbicide application. Modern adjuvants may be formulated to enhance compatibility with a wide range of herbicide formulations, reducing the risk of chemical reactions or precipitation in tank mixes. Additionally, adjuvants may be designed to meet stringent environmental regulations, ensuring minimal impact on non-target organisms and ecosystems.

[0007] Despite these advancements, challenges persist in the use of adjuvants with herbicides. Some adjuvants may cause unintended phytotoxic effects on crops, especially under adverse environmental conditions or when used at incorrect concentrations. Residual effects of adjuvants on soil and crops may be a concern, particularly in terms of persistence and potential ecological impacts. Adjuvants may not perform consistently across different environmental and agronomic conditions, affecting herbicide efficacy and overall weed control.

[0008] In conclusion, herbicides and adjuvants together play a pivotal role in modem agriculture by effectively controlling weeds and optimizing crop yields. While advancements in adjuvant technology have diversified their types and improved compatibility, challenges such as tank mix compatibility, phytotoxicity, residual effects, and variable performance under different conditions continue to drive innovation. The present disclosure seeks to address these challenges by proposing novel formulations and methods to optimize adjuvant use with herbicides, ensuring sustainable and effective weed management practices in agriculture.SUMMARY

[0009] In some examples, an herbicide formulation may include an herbicidally effective amount of an herbicide and an adjuvant composition. The herbicide may be substantially free of phosphorous atoms. The amphoteric surfactant may have general formula (I)R1— (XR2)m— N+(R3)(R4)— CH2— CH(R5)— COO- (I) where R1is hydrogen or a hydrocarbyl group, each X is independently a heteroatom-containing functional group, each R2is independently a hydrocarbyl group, m is an integer, R3and R4are independently hydrogens or hydrocarbyl groups, and R5is hydrogen or a hydrocarbyl group.The herbicide formulation may be substantially free of copolymers.

[0010] In some examples, a method of preparing an herbicide formulation may include mixing an adjuvant composition and an herbicide substantially free of phosphorous atoms to produce the herbicide formulation, the adjuvant composition comprising an amphoteric surfactant. The amphoteric surfactant may have general formula (I)R1— (XR2)m— N+(R3)(R4)— CH2— CH(R5)— COO- (I) where R1is hydrogen or Ci-is hydrocarbyl group, each X is independently an ether, thioether, sulfoxide, ester, thioester, or amide group, each R2is independently a C3-6 chain, m is a number from 0 to 8 such that the number of carbon atoms in R1— (XR2)mis from 8 to 24,R3and R4are independently hydrogens or C1.4 chains, and R5is hydrogen or a methyl group.The adjuvant composition may be capable of forming a homogenous mixture with an herbicide that exhibits less than a 5% increase in mass of solid residue after being mixed with an herbicide. The homogeneous mixture may have a soil residual life of at least 7 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 7 days.

[0011] In some examples, a system for controlling a population of unwanted vegetation may include an herbicide formulation and soil, which may be a medium for growing a crop. The herbicide formulation may include an herbicidally effective amount of an herbicide and anadjuvant composition. The herbicide may be substantially free of phosphorous atoms. The adjuvant composition may include a non-copolymer base ingredient and an amphoteric surfactant. The amphoteric surfactant may have general formula (I)R1— (XR2)m— N+(R3)(R4)— CH2— CH(R5)— COO- (I) whereR1is hydrogen or a hydrocarbyl group, each X is independently a heteroatom-containing functional group, each R2is independently a hydrocarbyl group, m is an integer,R3and R4are independently hydrogens or hydrocarbyl groups,R5is hydrogen or a hydrocarbyl group, and the herbicide formulation may be substantially free of copolymers.

[0012] In some examples, a method for controlling a population of unwanted vegetation in an environment may include applying an herbicide formulation to the environment. The herbicide formulation may include an herbicidally effective amount of an herbicide and an adjuvant composition. The herbicide may be a pre-emergent herbicide. The adjuvant composition may include an amphoteric surfactant having general formula (I):R1— (XR2)m— N+(R3)(R4)— CH2— CH(R5)— COO- (I) whereR1is hydrogen or a hydrocarbyl group, each X is independently a heteroatom-containing functional group, each R2is independently a hydrocarbyl group, m is an integer,R3and R4are independently hydrogens or hydrocarbyl groups,R5is hydrogen or a hydrocarbyl group.The herbicide formulation may have a soil residual life of at least 7 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 7 days. The herbicide formulation may have a phytotoxicity that reduces a population of a crop by no more than 10% of a population of a crop that is untreated by the herbicide formulation.BRIEF DESCRIPTION OF THE DRAWINGS

[0013] The disclosure can be understood in consideration of the following detailed description of various embodiments in connection with the accompanying drawings.

[0014] FIGS. 1 A through 1C show plots of the weed control (%) of different unwanted vegetation using S-metolachlor 960 EC (1200 mL / ha) without any adjuvant, with adjuvant 1 (0.2% v / v), and with an adjuvant having general formula (I) (0.2% v / v).

[0015] FIG. 1 A shows a plot of the weed control (%) of digitaria insularis without any adjuvant, with adjuvant 1 (0.2% v / v), and an adjuvant having general formula (I) (0.2% v / v).

[0016] FIG. IB shows a plot of the weed control (%) of eleusine indica by S-metolachlor 960 EC (1200 mL / ha) without any adjuvant, with adjuvant 1 (0.2% v / v), and an adjuvant having general formula (I) (0.2% v / v).

[0017] FIG. 1C shows a plot of the weed control commelina benghalensis by S-metolachlor 960 EC (1200 mL / ha) without any adjuvant, with adjuvant 1 (0.2% v / v), and an adjuvant having general formula (I) (0.2% v / v).

[0018] FIGS. 2 A through 2D show photographs of vegetation that includes weeds and the soybean crop after 49 days of application of different treatments that shows differences in weed control and phytotoxicity to the soybean crop.

[0019] FIG. 2A shows a photograph of untreated vegetation (no herbicide, no adjuvant).

[0020] FIG. 2B shows a photograph of vegetation treated with only S-metalachlor 960 EC (1200 mL / ha).

[0021] FIG. 2C shows a photograph of vegetation treated with S-metolachlor 960 EC (1200 mL / ha) and commercially available adjuvant (0.2% v / v).

[0022] FIG. 2D shows a photograph of vegetation treated with S-metolachlor 960 EC (1200 mL / ha) and adjuvant having general formula (I) (0.2% v / v).

[0023] FIG. 3 show bar graphs of the weed control (%) of Amaranthus rudis Sauer using S- metolachlor 83.7% EC (1.7 pt / A) without any adjuvant, with adjuvant 1 (1% v / v), with an adjuvant having General Formula (I) (0.2% v / v), with adjuvant 3 (0.4% v / v), and with adjuvant 2 (0.2% v / v) after 15 days, 41 days, and 66 days of application of a particular weed control treatment.

[0024] FIGS. 4 A through 4D show photographs of vegetation that includes weeds and the soybean crop after 41 days of application of different treatments that shows differences in weed control and no phytotoxicity to the soybean crop.

[0025] FIG. 4A shows a photograph of untreated vegetation (no herbicide, no adjuvant).

[0026] FIG. 4B shows a photograph of vegetation treated with only S-metalachlor 83.7% EC (1.7 pt / A).

[0027] FIG. 4C shows a photograph of vegetation treated with S-metolachlor 83.7% EC (1.7 pt / A) and commercially available adjuvant 1 (1% v / v).

[0028] FIG. 4D shows a photograph of vegetation treated with S-metolachlor 83.7% EC (1.7 pt / A) and adjuvant having general formula (I) (0.2% v / v).DETAILED DESCRIPTION

[0029] For purposes of promoting an understanding of the principles of the disclosure, reference will now be made to the embodiments illustrated in the drawings, and specific language will be used to describe the same. It will nonetheless be understood that no limitation of the scope of the disclosure is intended by the illustration and description of certain embodiments of the disclosure. In addition, any alterations and / or modifications of the illustrated and / or described embodiment s) are contemplated as being within the scope of the present disclosure. Further, any other applications of the principles of the disclosure, as illustrated and / or described herein, as would normally occur to one skilled in the art to which the disclosure pertains, are contemplated as being within the scope of the present disclosure.

[0030] To address the challenges of using adjuvants with herbicides, the present disclosure provides herbicide formulations, adjuvant compositions, and adjuvants that enhances the efficacy of an herbicide as well as systems and methods of making and using thereof. The adjuvant may enhance the residual activity of herbicides to control weeds without causing phytotoxicity in the crop of interest or harming its sprouting. The adjuvant may be used in smaller concentrations with herbicides than other commercially available adjuvants used with herbicides. The adjuvant may promote the residual increase of pre-emergent herbicides at lower doses than other adjuvants without causing phytotoxicity in the crop of interest or harming its sprouting. The residual increase may be characterized by an increased amount of herbicidal residue remaining in soil and weed for a certain duration of time. The residual increase may be characterized by an increase in the duration of herbicidal residue in the soil and weed. The residual increase may be characterized by the increased duration of effectiveness of herbicidal residue in the soil and on weeds.

[0031] The adjuvant may have excellent physiochemical characteristics, affording compatibility with an herbicide. In examples described in further detail below, the adjuvant or composition containing the adjuvant worked well with two very different types of soil on different ends of the soil spectrum, demonstrating the versatility of the adjuvant / adjuvant composition.

[0032] The adjuvant can enhance the effect of herbicides, such as pre-emergent herbicides, in several ways, including increasing herbicide adsorption on soil particles, decreasing availability for degradation via microorganisms and reducing leaching, facilitatingpenetration of the tank mix into the soil, reducing exposing the herbicide to ultraviolet light and heat, increasing the amount of water available in the soil, and making the herbicide more available to come into contact with weed seeds.

[0033] Adjuvant compositions or adjuvants added to a tank to form a mixture with herbicides or added to an herbicide formulation can increase the efficacy of post-emergent herbicides by improving the penetration of the active ingredient on the leaf surface. Adjuvant containing surfactant may promote stabilization and easy processing of high concentrations of herbicides. Additionally, these adjuvants can facilitate the absorption of the herbicide by plant cells, ensuring that a greater amount of the active ingredient reaches the site of action. They can also minimize herbicide drift during application, ensuring that the product reaches the desired target with greater precision. Furthermore, they can promote a more uniform distribution of the herbicide on the leaf surface, increasing coverage and treatment efficacy. Adjuvants can increase the retention of the herbicide on the leaf surface, reducing loss due to runoff or evaporation, and protect the herbicide from degradation by environmental factors such as ultraviolet light and heat, prolonging its activity. They can improve the compatibility and stability of the tank mix, preventing the formation of precipitates or phase separation, and reduce the surface tension of the solution, allowing for better coverage and penetration of the herbicide. Additionally, they can maintain the efficacy of the herbicide even under adverse conditions, such as high humidity or the presence of dust on the leaf surface, and facilitate the controlled release of the herbicide, ensuring prolonged and consistent action in weed control. These combined effects result in greater agronomic efficacy of post-emergent herbicides, providing more efficient and long-lasting weed control.

[0034] Adjuvants can play a crucial role in the pre-emergent herbicide formulation by promoting the uniform dispersion of active ingredients, improving the solubility and stability of the mixture. Surfactants, in turn, can act as wetting agents, spreaders, and emulsifiers, enhancing the stability of the herbicide formulation. The adjuvant can enhance the effect of herbicides, such as pre-emergent herbicides, in various ways. The adjuvant can increase the adsorption of herbicides onto soil particles, decrease the availability for degradation by microorganisms, and reduce leaching. Additionally, the adjuvant can facilitate the penetration of the tank mix into the soil or the straw remaining after harvest, or into the organic matter added as mulch. The adjuvant can also reduce the herbicide’s exposure to ultraviolet light and heat, increase the amount of water available in the soil, and make the herbicide more accessible to come into contact with weed seeds. Furthermore, the adjuvant can improve the uniform distribution of the herbicide in the soil, increase the persistence ofthe herbicide in the action zone, and promote a controlled release of the herbicide, resulting in prolonged and consistent efficacy in weed control.

[0035] The adjuvant may include a surfactant. The surfactant may be an amphoteric surfactant. Amphoteric compounds are molecules that can act as both acids and bases, meaning they can donate or accept protons (H+ ions) depending on the pH of their environment. Amphoteric compounds can function as surfactants in solutions where pH ranges widely, showing stability and varied solubility properties. Amphoteric surfactants can have both hydrophilic (water-attracting) and lipophilic (oil-attracting) groups within the molecule, making them effective at reducing surface tension and stabilizing emulsions.

[0036] The amphoteric surfactant may have general formula (I):R1— (XR2)m— N+(R3)(R4)— CH2— CH(R5)— COO- (I) where:R1is hydrogen or CMS hydrocarbyl, each X is independently an ether, thioether, sulfoxide, ester, thioester or amide bond, each R2is independently a C3-6 chain, m is a number from 0 to 8 such that the number of carbon atoms in R1— (XR2)mis from 8 to 24,R3and R4are independently hydrogens or C1.4 chains,R5is hydrogen or methyl.

[0037] The amphoteric surfactant having general formula (I) may be obtained by reacting the respective tertiary amines with acrylic or methacrylic acid represented by scheme (II).CH(R5)— COO- (II)

[0038] According to the process represented by scheme (II), a tertiary amine may be added to an aqueous solution of (meth)acrylic acid partially neutralized with sodium hydroxide to prevent an acid-base reaction from taking place. A polymerization inhibitor may be used in the process. The mixture may be reacted for 5 hours at 60 °C, and the amphoteric surfactant may be obtained in water, which can be partially removed by means of a drying process.

[0039] Partial removal of water may allow for the addition of a solvent to the amphoteric surfactant, such as solvents belonging to the class of glycols, such as glycerin, which may serve as a moisturizer and aid in spreading agrochemical formulations (Tann, S. 9th International Symposium on Adjuvants for Agrochemicals, 2010, ISAA Society).

[0040] The adjuvant may include an amphoteric surfactant belonging to the class of amphopropanoates, such as the class of triakyl ammonium propanoates.

[0041] The adjuvant may have certain characteristics (e.g., physicochemical characteristics) that may afford compatibility with an herbicide. Physicochemical characteristics generally refers to the physical and chemical properties of a substance and may determine how the substance behaves under different conditions. Physicochemical characteristics may include appearance observed at 25 degrees Celsius, solubility in water, density recorded at 25 degrees Celsius, flash point, melting point / freezing point, and surface tension of 0.5% m / v adjuvant at 25 degrees Celsius measured using the Wilhelmy plate method.

[0042] The physical appearance of the adjuvant may be observed when the adjuvant is at 25°C. The physical appearance of the adjuvant may be liquid, solid, powder, etc. Physical appearance can influence handling packaging, and application methods. For example, powdered surfactants may require different handling compared to liquid forms.

[0043] Solubility relates to the ability of a substance to dissolve in a solvent (e.g., water solubility). Solubility is the maximum amount of a solute that can dissolve in a solvent at a given temperature and pressure. Solubility can indicate whether a mixture remains homogeneous or experiences precipitation. This term broadly describes how substances interact in a mixture, including their tendencies to stay dissolved or precipitate out. In a homogenous mixture, all components are evenly distributed, forming a single phase without any separation. This indicates good solubility of the substances in the solvent. When there is precipitation, one or more components come out of solution, forming a solid phase separate from the liquid. This indicates poor solubility or conditions (e.g., temperature, concentration) that exceed the solubility limits. Factors may affect solubility behavior may include temperature, concentration, nature of solvents and solutes, pH levels, and presence of other ions or compounds. Higher temperatures may increase solubility, while lower temperatures can cause precipitation. Exceeding the solubility limit (saturation point) can lead to precipitation. Polar solvents may dissolve polar solutes (and non-polar solvents dissolve nonpolar solutes) more effectively. pH levels can affect the ionization of solutes and their solubility. Common ion effect, complexation, or interactions with other compounds can affect solubility.

[0044] The adjuvant may be insoluble or soluble (e.g., partially or completely) in water. Surfactants may be used in aqueous solutions so solubility in water may be crucial for their effectiveness. Poor solubility can lead to phase separation or reduced efficacy.

[0045] Density is a measure of how much mass is contained in a given volume of a substance. The density of the adjuvant at 25°C may be 95 g / cm3to 1.10 g / cm3. The density of the adjuvant at 25°C may be 1.0 g / cm3. The density may affect how the adjuvant (e.g.,surfactant) behaves when mixed with other substances, such as herbicides. Differences in density can lead to stratification in tank mixes, affecting application consistency.

[0046] The flash point is the lowest temperature at which a substance can ignite or produce enough vapor to ignite in air. The adjuvant may have a flash point of at least 70°C, at least 75°C, 80°C, at least 85°C, at least 90°C, at least 95°C, or at least 100°C. Flash point may be critical for safety considerations during storage, transportation, and handling of the adjuvant. Lower flash points may indicate higher flammability risks.

[0047] The melting point / freezing point is the temperature at which a substance changes from solid to liquid (melting point) or liquid to solid (freezing point). Melting and freezing points may influence the physical form and stability of the adjuvant, and their consideration may help achieve effective formulation and application of the adjuvant and determine suitable storage conditions of the adjuvant. The adjuvant may have a melting point / freezing point of - 15°C to -25°C. The adjuvant may have a melting point / freezing point of -21°C.

[0048] Surface tension is a measure of the cohesive forces between molecules at the surface of a liquid. Surface tension is the force acting on the surface of a liquid that tends to minimize the area of the surface. A lower surface tension indicates that the liquid molecules at the surface are less tightly held together. Surface tension may be expressed in millinewtons per meter (mN / m). Since surface tension may be temperature-dependent, the surface tension of a substance may be taken at a specific temperature, such as 25°C. The surface tension of a substance may be taken at a certain concentration of the substance, and such concentration of the substance or solute in the solution may be 0.5% m / v (i.e., 0.5 grams of solute per 100 milliliters of solution). The Wilhelmy plate method may be used to measure surface tension. In the Wilhelmy plate method, a thin plate (e.g., made of a material such as platinum or filter plate) may be immersed into the liquid, and the force required to detach the plate from the liquid surface is measured as this force is related to the surface tension of the liquid. An adjuvant at a concentration of 0.5% m / v may have a surface tension of 30 mN / m - 45 mN / m, such as 35 mN / m - 40 mN / m, at 25°C using the Wilhelmy plate method. An adjuvant at a concentration of 0.5% m / v may have a surface tension of 37 mN / m at 25°C using the Wilhelmy plate method.

[0049] When considering an adjuvant, such as a surfactant, for use with herbicides, the surface tension may play a crucial role in determining their effectiveness. Surfactants may lower surface tension, allowing them to reduce interfacial tension between liquids or between a liquid and a solid, which may enhance wetting and spreading on target surfaces.Surfactants with lower surface tensions (e.g., 25-30 mN / m or lower) may be more effective atwetting and spreading herbicide solutions on plant surfaces. This allows the herbicide to cover the leaves more uniformly, improving its efficacy. Lower surface tension may help herbicide solutions penetrate through the waxy cuticle of plant leaves, reaching the target site more effectively. This can be crucial for herbicide uptake and efficacy. Proper surfactant selection can improve the rainfastness of herbicides, ensuring they remain effective even after rainfall by enhancing adhesion and absorption.

[0050] Table 1 shows physiochemical characteristics of an adjuvant.Table 1. Physicochemical Characteristics of an Adjuvant

[0051] The adjuvant may have other defining characteristics. The adjuvant may be biodegradable, which is the capability of being broken down by natural processes into nontoxic components. Biodegradability of the adjuvant may be important for environment safety, ensuring that the adjuvant does not persist in the environment and cause long-term harm. The adjuvant may allow for good handling by being easy and safe to use, suggesting that it does not pose significant risks to the user during application. Good handling may refer to properties, such as low toxicity, non-corrosiveness, and non-irritating. The adjuvant may exhibit versatility; the adjuvant can be used in a variety of applications and formulations. The adjuvant may be compatible with a wide range of products and conditions, making it a flexible option for different scenarios. The adjuvant may prove to enhance the absorption or uptake of the active ingredient into the target organism (e.g., an herbicide into a plant). The validation of uptake may be based on scientific studies or field trials showing increased efficacy of the adjuvant. The adjuvant may have electrolyte resistance, where the adjuvant may remain effective in the presence of electrolytes (e.g., salts) that might be found in water or other mixtures. An adjuvant with electrolyte resistance may mean that the adjuvant does not precipitate or lose it effectiveness when mixed with hard water or other solutions containing salts. The adjuvant may meet the regulatory standards for safety and effectivenessset by the Environmental Protection Agency (EP A). EPA evaluation may include tests for environmental impact, human health risks, and efficacy.

[0052] The adjuvant may be combined with a pest control agent or an agricultural compound, such as an herbicide, by itself without other components or with other components within an adjuvant composition. The adjuvant composition may include an adjuvant. The adjuvant composition may include an adjuvant and other components, such as one or more additives, one or more base ingredients, and / or one or more additional adjuvants.

[0053] In some examples, the adjuvant composition may include one or more additives. Examples of additives include water, oil, solvents, preservatives, stabilizers, antioxidants, acidifiers, chelates, complexing agents, hydrotropes, clarifiers, anti-freezing agents, antifoams, anti-drift agents, dyes, rheology modifiers, surfactants, emulsifiers, dispersants, wetting agents, humectants, penetrants, buffers, thickeners, defoamers, UV protectants, and combinations thereof. The additive may be a non-copolymer. The additive may be an oil, an acid, a resin, and a polyol. The additive may be a mineral oil, seed oil, an acid, a resin, or a polyol. Adjuvants based on seed oils, mineral oils, acids-based, resin-based, polyol-based can increase the residual of pre-emerging herbicides in the soil, prolonging the clean field for sprouting of the crop of interest. In some examples, the additive is a mineral oil.

[0054] The additive may cooperate or enhance the adjuvant and / or herbicide formulation to enhance the residual activity of the herbicide formulation. Adding the additive to a surfactant can significantly improve the performance of the surfactant in herbicide applications by optimizing surface tension, enhancing spreading and coverage, and improving overall efficacy and stability on plant surfaces. The additive may lower the surface tension of the adjuvant and / or herbicide formulation and improve wetting and spreading on plant surfaces, which may enhance the effectiveness of herbicide applications. The combined or synergistic effect of the adjuvant and the additive can bring the surface tension closer to the ideal range (e.g., around 25-30 mN / m) for herbicide applications, ensuring better adhesion and penetration. The additive can alter the viscosity of the surfactant, emulsify the herbicide formulation, enhance the rainfastness and persistence of an herbicide on plant surfaces, and change the compatibility between the adjuvant composition with the herbicide.

[0055] An additive may be considered a base ingredient if it forms the bulk of a formulation. In some examples, the adjuvant composition may include one or more base ingredients or additives that can be considered base ingredients. The base ingredient may serve as the foundational substance in which the adjuvant is mixed, providing support for the overall structure and function of the adjuvant composition and / or herbicide formulation. The baseingredient may be a carrier used to carry and deliver active ingredients, such as a surfactant and / or an herbicide, to the target area. The carrier may ensure even distribution and application of the active ingredient across the target area.

[0056] In some examples, the adjuvant composition may include one or more additional adjuvants. Examples of additional adjuvants include surfactants, oils, acids, resins, and polyols. The additional adjuvant may include one or more anionic surfactant, non-ionic surfactant, amphoteric surfactant, mineral oil, seed oil, an acid, a resin, or a polyol. In some examples, the additional adjuvant may include mineral oil. Non-ionic surfactants do not dissociate into ions in solution. Instead, they remain electrically neutral, which affects their behavior and interactions with other substances in the formulation. The adjuvant composition can contain other surfactants added by means of simple mixture with the aforementioned amphoteric surfactant. Examples of additional surfactants may include, but are not limited to, as an anionic, cationic, nonionic or amphoteric surfactant, and anionic, cationic or nonionic polymers, ethoxylated alkyl ethers, phosphated ethoxylated alkyl ethers, ethoxylated alkyl etheramines, alkylpolyglucosides, ethoxylated alkylpolyglucosides, ethoxylated imidazolines, polysiloxane derivatives, alkyl dimethyl amine oxides, alkyl dimethyl betaines, alkyl amido propyl amines and ethoxylated alkyl amines. One of the advantages of the adjuvant composition may be the ease of compatibilization of amphoteric surfactants having general formula (I) with these other surfactants.

[0057] The adjuvant may be 0.01% v / v to 100% v / v of the adjuvant composition. The adjuvant may be 0.1% v / v to 100% v / v of the adjuvant composition. The adjuvant may be 0.01% v / v to 80% v / v of the adjuvant composition. The adjuvant may be 0.1% v / v to 80% v / v of the adjuvant composition. The adjuvant may be 0.01% v / v to 10% v / v of the adjuvant composition. The adjuvant may be present at a concentration of 0.01% v / v to 10% v / v in water within the adjuvant composition. The adjuvant may be 0.1% v / v to 10% v / v of the adjuvant composition. The adjuvant may be 0.01% v / v to 5% of the adjuvant composition. The adjuvant may be 0.1% v / v to 5% of the adjuvant composition. In some examples, the adjuvant composition may include 0.01% v / v to 100% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the adjuvant composition may include 0.1% v / v to 100% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the adjuvant composition may include 0.01% v / v to 80% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the adjuvant composition may include 0.1% v / v to 80% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the adjuvant composition may include0.01% v / v to 10% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the adjuvant may be present at a concentration of 0.01% v / v to 10% v / v in water within the adjuvant composition. In some examples, the adjuvant composition may include 0.1% v / v to 10% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the adjuvant composition may include 0.01% v / v to 5% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the adjuvant composition may include 0.1% v / v to 5% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the amphoteric surfactant is 0.01% v / v to 5% v / v of the herbicide formulation. In some examples, the amphoteric surfactant is 0.01% v / v to 80% v / v of the herbicide formulation. In some examples, the amphoteric surfactant is less than 1% v / v of the herbicide formulation

[0058] In some examples, the adjuvant can be directly used without the aid of additional surfactants to form an emulsion. In some examples, the adjuvant may be used to combat unwanted vegetation before germination as opposed to improving the growth of vegetation, such as improving soil conditions for enhanced root and plant growth.

[0059] In some examples, the adjuvant composition may be substantially free of phosphorous atoms. As used herein, the term 'substantially free of phosphorous atoms' refers to a formulation that contains phosphorous atoms in an amount that is negligible or non- detectable, such that the presence of phosphorous atoms does not materially affect the performance or properties of the formulation. For example, the phosphorous content may be less than 0.01% by weight of the total composition, the composition may contain no intentionally added phosphorous, with only trace amounts present as impurities, or may be below the detectable limits of standard analytical methods used to measure phosphorous. In some examples, the adjuvant composition does not contain any phosphorous atoms.

[0060] In some examples, the adjuvant composition may be substantially free of copolymers. As used herein, the term 'substantially free of copolymers' refers to a formulation that contains copolymers in an amount that is negligible or non-detectable, such that the presence of copolymers does not materially affect the formulation’s performance or intended properties. For example, the copolymer content may be less than 0.01% by weight of the total composition, or the composition may contain no intentionally added copolymers, with only trace amounts present as impurities.

[0061] In some examples, the adjuvant composition may be substantially free of hydrotropes. In some examples, the adjuvant composition may include a surfactant and be substantially free of hydrotropes. As used herein, the term “substantially free of hydrotropes” refers to aformulation that contains hydrotropes in an amount that is negligible or non-detectable, such that the presence of hydrotropes does not materially affect the formulation’s performance or intended properties. For example, the hydrotrope content may be less than 0.01% by weight of the total composition, or the composition may contain no intentionally added hydrotropes, with only trace amounts present as impurities.

[0062] A hydrotrope is a chemical substance used to improve the solubility of otherwise insoluble substances in water. Hydrotropes can enhance the solubility of hydrophobic substances (like oils or other nonpolar compounds) in water, which otherwise would be insoluble or only sparingly soluble. In some examples, the adjuvant in an adjuvant composition is hydrophilic or exhibit hydrophilic properties. In some examples, the additional one or more adjuvants in the adjuvant composition is hydrophilic or exhibit hydrophilic properties. "Hydrophilic" means "water-loving." A hydrophilic substance has an affinity for water and tends to dissolve in or interact with water. In some examples, the adjuvant in an adjuvant composition is not lipophilic or does not exhibit lipophilic properties. In some examples, the additional one or more adjuvants in the adjuvant composition are not lipophilic or does not exhibit lipophilic properties. "Lipophilic" means "fat-loving" or "oilloving." A lipophilic substance has an affinity for fats, oils, or non-polar solvents and tends to dissolve in or interact with lipids. The adjuvant in an adjuvant composition may or may not be amphiphilic or may or may not exhibit amphiphilic properties. The additional one or more adjuvants in the adjuvant composition may or not be amphiphilic or may or may not exhibit amphiphilic properties. Amphiphilic substances have both hydrophilic and lipophilic regions within the same molecule. This dual nature allows them to interact with both water and fat / oil environments.

[0063] The herbicide formulation may include an herbici dally effective amount of an herbicide and an adjuvant composition.

[0064] An herbicide may be used to control unwanted plants (weeds) by inhibiting specific physiological processes in plants, such as enzymes or processes essential for plant growth, for example, photosynthesis, amino acid synthesis, and fatty acid synthesis. An herbicide may be a pre-emergent or a post-emergent herbicide.

[0065] Pre-emergent herbicides may be applied to the soil before the targeted weed seeds have a chance to germinate and emerge from the soil surface. These herbicides may create a chemical barrier at or just below the soil surface, which affects the emerging seedlings. When the weed seeds begin to germinate, the young shoots or roots may come into contact with the herbicide, which then disrupts their growth processes, preventing the weeds fromestablishing. Pre-emergent herbicides should be applied before the weed seeds germinate, typically in early spring or fall. They may be most effective against annual weeds that germinate from seeds. These herbicides may be incorporated into the soil through rainfall or irrigation to ensure they reach the zone where weed seeds are germinating.

[0066] Post-emergent herbicides may be applied after the targeted weeds have already emerged and are visible above the soil surface. These herbicides may be absorbed by the leaves and stems of the growing plants. Depending on the herbicide, it can either kill the entire plant (non-selective) or target specific types of weeds (selective) without harming desired plants. Post-emergent herbicides may be applied when the weeds are actively growing, which can be any time during the growing season. They may be effective against a wide range of weeds, including annuals, perennials, grasses, and broadleaf weeds. These herbicides are typically sprayed directly onto the foliage of the weeds.

[0067] Unlike post-emergent herbicides, which act on the leaves, fruits, and other visible parts of plants and have various modes of action, such as inhibition of photosynthesis, amino acid synthesis, and cell division, pre-emergent herbicides act directly on the seed or at the beginning of radicle sprouting. These herbicides use specific modes of action, such as inhibiting germination and blocking root growth. Differences in the modes of action and biological targets between pre-emergent and post-emergent herbicides can lead to varying effects from the same composition, including those containing an adjuvant.

[0068] Herbicides can be categorized into several chemical classes, each defined by its distinct chemical structure and mechanism of action. These classes include:

[0069] Amino Acid Synthesis Inhibitors: This class of herbicides functions by inhibiting the synthesis of essential amino acids, which are critical for plant growth and development. Examples of amino acid synthesis inhibitors include glyphosate, glufosinate, and chlorsulfuron.

[0070] Photosynthesis Inhibitors: Herbicides in this category disrupt the photosynthetic process in plants, thereby preventing them from producing the energy necessary for survival. Notable examples of photosynthesis inhibitors are atrazine, simazine, and metribuzin.

[0071] Growth Regulator Herbicides: These herbicides mimic plant hormones, leading to abnormal growth patterns and eventual plant death. Common examples include 2,4-D, dicamba, and triclopyr.

[0072] Carotenoid Biosynthesis Inhibitors: This class inhibits the synthesis of carotenoids, which are pigments essential for protecting plants from oxidative damage. Examples include clomazone and fluridone.

[0073] Cellulose Synthesis Inhibitors: Herbicides classified as cellulose synthesis inhibitors block the formation of cellulose, which is vital for cell wall integrity. Isoxaflutole and flufenacet are examples of this class.

[0074] Seedling Growth Inhibitors: These herbicides prevent the growth of young seedlings by interfering with cell division or elongation. Oxyfluorfen and chlorpropham are examples.

[0075] Microtubule Assembly Inhibitors: This class disrupts the formation of microtubules, which are essential for cell division and growth. Pendimethalin and trifluralin are examples.

[0076] Non-selective Herbicides: Non-selective herbicides affect all plants they come into contact with and are used for total vegetation control. Paraquat and glufosinate fall into this category.

[0077] Selective Herbicides: Selective herbicides are designed to target specific types of weeds or plants while leaving desired crops or plants unharmed. Atrazine and MCPA are examples of selective herbicides.

[0078] Sulfonylureas: This class of herbicides inhibits the synthesis of branched-chain amino acids, which are crucial for plant growth. Chlorsulfuron and metsulfuron methyl are examples of sulfonylureas.

[0079] Each chemical class of herbicide is characterized by its unique mode of action, making them suitable for various weed control applications and agricultural practices.

[0080] An herbicide may be a synthetic organic chemical that is manufactured through chemical synthesis from organic (carbon-based) precursors. For example, an herbicide may be derived from petroleum-based precursors through various synthesis processes. An herbicide may be a nitrogen-containing compound. An herbicide may contain an aromatic ring, which may contribute to the herbicide’s stability and ability to interact with biological molecules. An herbicide may contain a heterocyclic ring (i.e., rings with atoms of at least two different elements), which may contribute to the activity of the herbicide.

[0081] An herbicide may include at least one chemical class selected from the group consisting of: acetamides, arylaminopropionic acid, benzoic acid, chlorocarbonic acid, phenoxycarboxylic acid, phosphinic acid, quinolinecarboxylic acid, amides, aryloxyphenoxypropionates (FOPs), arylpicolinate, benzamides, benzofurans, benzothiadiazinones, bipyridyliums, carbamates, cyclohexanediones (DIMs), chloroacetamides (VI), chloroacetamides (V2), chloroacetamides (V3), diphenyl ethers, dinitroanilines, dinitrophenols, phenylpyrazoles, phenylpyrazolines (DENs), phenylpyridazines, phosphoramidates, phosphorodithioates, phthalates, semicarbazones, glycines, imidazolinones, long-chain fatty acid inhibitors, isoxazoles, isoxazolidinones, N-phenylphthalimides, nitriles, organoarsenicals, oxadiazoles, oxazolidinediones, oxypyrazoles, pyrazolines, pyridazinones, pyridines, pyridinecarboxamides, pyrimidindiones, pyrimidinyl(thio)benzoates, sulfonylaminocarbonyl-triazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolecarboxamides, triazolopyrimidines, triketones, uracils and ureas. The herbicide may also be a beneficial microorganism or its metabolites, selected from the group of fungi, Gram-negative or Gram-positive bacteria. The herbicide may also be a molecule from a renewable source.

[0082] Herbicides may include triazines, triketones, imidazolinones, chloroacetamides, aryl triazolinones, dinitroanilines, amides, isoxazolidinones, oxadiazoles, pyrazoles, phenoxy herbicides, benzoic acids, carbamates, HPPD inhibitors, sulfonylureas, and organophosphorous compounds. Pre-emergent herbicide may include dinitroanilines, chloroacetamides, triazines, imidazolinones, isoxazolidinones, oxadiazoles, or pyridines. An example of a triazine includes atrazine. An example of a triketone or isoxazolidinone includes mesotrione. An example of an imidazolinone is imazetapyr. An example of a chloroacetamide is S-metolachlor. An example of an aryl triazolinone or oxadiazole is sulfentrazone. An example of an organophosporous compound is glyphosate. In some examples, the herbicide in an herbicide formulation is selected from at least one of a triazine, a triketone, an imidazolinone, a chloroacetamide, an aryl triazolinone, and an organophosphorous compound. In some examples, the herbicide in an herbicide formulation is selected from at least one of a triazine, a triketone, an imidazolinone, a chloroacetamide, and an aryl triazolinone. In some examples, the herbicide in an herbicide formulation is selected from at least one of atrazine, mesotrione, imazetapyr, S-metolachlor, sulfentrazone, and glyphosate. In some examples, the herbicide in an herbicide formulation is selected from at least one of atrazine, mesotrione, imazetapyr, S-metolachlor, and sulfentrazone.

[0083] Atrazine can have the chemical formula CxHuCINs. Atrazine may be referred to as 6- chloro-N-ethyl-N'-(l-methylethyl)-l,3,5-triazine-2,4-diamine. Atrazine may be a 1,3,5- triazine derivative. The structure of atrazine includes the 1,3,5-triazine ring substituted with a chlorine atom and two amine groups (ethylamine and isopropylamine) at the 2 and 4 positions, respectively. Atrazine may be synthesized from cyanuric chloride by nucleophilic substitution reactions with ethylamine and isopropylamine. An herbicide, atrazine may inhibit photosynthesis by binding to the DI protein in the photosystem II complex in chloroplasts. This inhibition may prevent the electron transport chain from functioning, thereby halting the production of ATP and NADPH, which are essential for the Calvin cycleand other metabolic processes in plants. Atrazine may be used to control broadleaf and grassy weeds in crops like corn, sorghum, and sugarcane. Atrazine may be used as both a pre-emergent and a post-emergent herbicide. As a pre-emergent, it may inhibit photosynthesis in germinating weed seeds. As a post-emergent, it may be absorbed by leaves and may disrupt photosynthesis in emerged weeds.

[0084] Mesotrione can have the chemical formula C14H13NO7S. Mesotrione may be referred to as 2-(4-methylsulfonyl-2-nitrobenzoyl)-l,3-cyclohexanedione. Mesotrione has a 1,3- cyclohexanedione ring, which is a six-membered ring with two ketone groups. Mesotrione may be derived from the natural phytotoxin leptospermone through synthetic modification, involving steps like chlorination and nitration followed by cyclization. As an herbicide, mesotrione may inhibit the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD). HPPD may be involved in the synthesis of plastoquinone and tocopherols. Inhibition of HPPD can lead to a depletion of carotenoids, which protect chlorophyll from photodegradation. As a result, plants may exhibit bleaching symptoms and may die due to loss of photosynthetic capability. Mesotrione may be used for selective pre- and post-emergence control of broadleaf weeds in maize and other crops. As a pre-emergent, it can control weeds before they emerge. As a post-emergent, it can be absorbed through the leaves and affects the same biochemical pathway.

[0085] Imazetapyr can have the chemical formula C15H19N3O3. Imazetapyr may be referred to as (RS)-2-[4,5-dihydro-4-methyl-4-(l-methylethyl)-5-oxo-lH-imidazol-2-yl]-5-ethyl-3- pyridinecarboxylic acid. Imazetapyr may contain an imidazolinone ring structure. Imazetapyr has a pyridine ring with a carboxylic acid group at the 3 -position. Imazetapyr may be synthesized through a series of steps involving the formation of an imidazolinone ring, typically starting from precursors like 2-aminobenzonitrile. Imazetapyr may inhibit acetohydroxyacid synthase (AHAS) or acetolactate synthase (ALS), enzymes critical for the synthesis of branched-chain amino acids (valine, leucine, and isoleucine). Inhibition of this enzyme can disrupt protein synthesis and cell growth, leading to plant death. Imazetapyr may be used for pre- and post-emergence control of annual and perennial grasses and broadleaf weeds in a variety of crops, such as soybeans, peanuts, and other legumes. It can be applied pre-emergence to control weed seedlings as they germinate and post-emergence to control growing weeds.

[0086] Sulfentrazone can have the chemical formula C11H10CI2F2N4O3S. Sulfentrazone may be referred to as N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-lH- l,2,4-triazol-l-yl]phenyl]methanesulfonamide. Sulfentrazone may contain a triazolinone ringattached to a benzene ring. Sulfentrazone may be synthesized through steps involving the reaction of 4-chlorobenzonitrile with hydrazine to form a triazolinone ring. Sulfentrazone may inhibit protoporphyrinogen oxidase (PPO), an enzyme involved in the synthesis of chlorophyll. This inhibition can lead to the accumulation of protoporphyrin IX, a photosensitizing molecule that generates reactive oxygen species under light, causing cell membrane disruption and plant death. Sulfentrazone may be used for pre-emergence and early post-emergence control of broadleaf weeds and some grasses in soybeans, sunflowers, peanuts, and other crops and turf. As a pre-emergent, it can control weeds before they emerge. As a post-emergent, it can cause rapid membrane disruption in contact with treated weed foliage.

[0087] S-metolachlor can have the chemical formula C15H22CINO2. S-metolachlor may be referred to has (S)-2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-l- methylethyl)acetamide. S-metolachlor may contain a chloroacetamide functional group. The core structure of S-metolachlor is an acetamide derivative with substituents in which the acetamide nitrogen is substituted with a 2-ethyl-6-methylphenyl group (a benzene ring with ethyl and methyl groups at the 2- and 6-positions) and a 2 -m ethoxy- 1 -methylethyl group (a methoxy group attached to a secondary carbon which is also attached to a methyl group) and the acetamide carbonyl carbon is bonded to a chlorine atom (2-chloro). S-Metolachlor may be produced by reacting 2-ethyl-6-methylaniline with methyl chloroacetate, followed by cyclization and separation of the S-isomer. S-metolachlor may inhibit the synthesis of very long chain fatty acids (VLCFAs), affecting cell division and growth in emerging shoots and roots. VLCFAs can be essential components of cell membranes. By inhibiting their synthesis, S-metolachlor can affect cell division and elongation, particularly in emerging shoots and roots, resulting in stunted growth and death of seedlings. S-metolachlor may be used for pre-emergence control of annual grasses and some broadleaf weeds in crops like com, soybeans, and cotton. S-Metolachlor can be primarily used as a pre-emergent herbicide due to its mode of action and effectiveness in controlling weeds at the germination stage. Once weeds have emerged and established themselves, their growth processes and metabolism can change. The pathways that S-metolachlor targets may be less active in mature plants, making it ineffective as a post-emergent herbicide.

[0088] Glyphosate may contain a phosphonomethyl amino acid structure. Glyphosate may be synthesized through the reaction of glycine (an amino acid) with formaldehyde and phosphorus trichloride, followed by oxidation. Glyphosate may inhibit the enzyme 5- enolpyruvylshikimate-3 -phosphate synthase (EPSPS). EPSPS can be a key enzyme in theshikimic acid pathway, which may be essential for the synthesis of aromatic amino acids (phenylalanine, tyrosine, and tryptophan) in plants, bacteria, fungi, and some protozoans. By inhibiting EPSPS, glyphosate may prevent the production of these aromatic amino acids, which can be vital for protein synthesis and plant growth. This can lead to the gradual death of the plant because it cannot produce essential proteins.

[0089] Glyphosphate may uniquely target a fundamental process for aromatic amino acid synthesis, which is different from the other herbicides that target photosynthesis, fatty acid synthesis, or other amino acid synthesis pathways. Glyphosate can be used post-emergence to control a wide range of weeds. It may be a systemic herbicide that is absorbed through the leaves and translocated throughout the plant, effectively killing it. It might not be used as a pre-emergent because it can require active growth for absorption and may not effective on ungerminated seeds.

[0090] Glufosinate may also be used post-emergence. It can be a contact herbicide that may be absorbed through the foliage and may disrupt the production of glutamine, leading to the accumulation of ammonia and subsequent plant death. Like Glyphosate, it may not be effective as a pre-emergent because it may not affect ungerminated seeds.

[0091] The herbicide, such as a pre-emergent herbicide, may be formulated as a suspension concentrate (SC), emulsifiable concentrate (EC), water-dispersible granule (WG), soluble concentrate (SL), wettable powder (WP), granule (GR), microemulsion (ME), capsule suspension (CS), paste (PA), aerosol (AE), dry powder (DP), soluble liquid (SL), water- dispersible concentrate (DC), gel (GL), effervescent tablet (ET), controlled release formulation (CR), suspended capsule (CS), oil dispersion (OD), concentrated suspension for seed treatment (FS), or aqueous dispersion (AD).

[0092] The herbicide formulation may include additional agricultural compounds or pest control agents, such as insecticides, fungicides, herbicides, desiccants, defoliants, acaricides, nutrients, miticides, bactericides, biocides, ovicides, nematicides, insect growth regulators, plant growth regulators, and combinations thereof. The additional agricultural compounds or pest control agents may be mixed with the adjuvant composition prior to being mixed with the herbicide. In some examples, the adjuvant composition may contain an adjuvant and water, and the additional agricultural compounds or pest control agents may be added to the water prior to mixing with the adjuvant to produce the adjuvant composition. In some examples, the additional agricultural compounds or pest control agents may be added to the herbicide formulation after the herbicide and the adjuvant composition are mixed. In someexamples, the herbicide, such as a pre-emergent herbicide, is mixed with water and added to the adjuvant composition to form the herbicide formulation.

[0093] An herbicide formulation may include a synergistic combination of an herbicide and an adjuvant or adjuvant composition. A synergistic combination refers to the combination of multiple components that work together in a way that produces a greater effect than the sum of their individual effects, for example, enhanced performance, efficiency, or functionality beyond what could be achieved by individual components alone. Careful consideration of the balance of each component may ensure that the components are compatible with each other and the herbicide formulation in synergy with the adjuvant composition extends the duration of weed control without causing phytotoxicity to the crop of interest, as long as the herbicide being used is selective and / or the crop is resistant to the herbicide being used. The synergy arising from the combined action of an herbicide and an adjuvant or an adjuvant composition may result in improved or superior herbicidal (e.g., increased residual activity of the herbicide, minimal or no phytotoxicity to the crops of interest (e.g., soybean crop), etc.) and physicochemical characteristics (e.g., surface tension, etc.) of the herbicide formulation as compared to a formulation that lacks the adjuvant or adjuvant composition (e.g., does not use an adjuvant or adjuvant composition or uses a different adjuvant or adjuvant composition).

[0094] An example of a synergistic combination of an herbicide and an adjuvant or adjuvant composition includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition. An herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be measured by the soil residual life of the herbicide or herbicide formulation and / or compatibility between the herbicide and the adjuvant or the adjuvant composition. An herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be characterized by no or minimal phytotoxicity to crops of interest (e.g., soybean crop).

[0095] An herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition containing the adjuvant may be characterized by the herbicide or herbicide formulation having a soil residual life of at least 7 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 7 days. In some examples, the herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be characterized by the herbicide or herbicide formulation having a soil residual life of at least 14 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwantedvegetation that is untreated by the herbicide formulation for at least 14 days. In some examples, the herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be characterized by the herbicide or herbicide formulation having a soil residual life of at least 15 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 15 days. In some examples, the herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be characterized by the herbicide or herbicide formulation having a soil residual life of at least 28 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 28 days. In some examples, the herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be characterized by the herbicide or herbicide formulation having a soil residual life of at least 41 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 41 days. In some examples, the herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be characterized by the herbicide or herbicide formulation having a soil residual life of at least 42 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 42 days. In some examples, the herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be characterized by the herbicide or herbicide formulation having a soil residual life of at least 66 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 66 days. To maintain a population of unwanted vegetation at no more than 10% of an untreated population, an herbicide formulation without an adjuvant may provide control for 7 days to14 days. However, by incorporating an adjuvant or adjuvant composition, the duration of effective control may be extended from 7 days to about 14 to 66 days, for example, 14 days,15 days, 28 days, 41 days, 42 days, or 66 days. For example, by incorporating an adjuvant or adjuvant composition, the duration of effective control may be extended from 7 days to 14 days for Commelina benghalensis, from 14 days to 28 days for Eleusine indica. or from 14 days to 42 days for Digitaria insularis. The increase in residual time by using an adjuvant may be at least 200%, at least 100%, or at least 7%. In some examples, the increase inresidual time by using an adjuvant may be at least 7% after 66 days of application. In some examples, the herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may maintain weed control rates of 80%-97% after 66 days of application. In some examples, the herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be characterized by the herbicide or herbicide formulation having a soil residual life of at least 66 days to maintain a population of unwanted vegetation to not more than 3-20% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 66 days. This parameter may suggest that there is an increase in residual activity or an increase in the duration of residue that remains in the soil or weed or an increase in the amount of residue that remains in the soil or weed for a certain length of time compared to when no adjuvant / adjuvant composition is used. The increase of residual activity or increase of duration of residue that remains in the soil or weed or increase of the amount of residue that remains in the soil or weed for a certain length of time compared to when no adjuvant / adjuvant composition is used may be 5%-20%, 10%- 15%, or at least 14%. The increase of herbicidal residual activity or increase of duration of herbicidal residue that remains in the soil or weed or increase of the amount of herbicidal residue that remains in the soil or weed for a certain length of time compared to when no adjuvant / adjuvant composition is used may extend the duration of weed control. This may be a significant contribution to agriculture and the management of unwanted plants. When herbicides remain active for longer, farmers can reduce the frequency of application and optimize the use of these chemicals, resulting in economic and environmental benefits.

[0096] An herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be characterized by the herbicide formulation having a phytotoxicity that reduces a population of a crop of interest by no more than 10% of a population of unwanted vegetation that is untreated by the herbicide formation for at least 7 days, at least 14 days, at least 15 days, at least 28 days, at least 41 days, at least 42 days, at least 66 days etc.

[0097] The herbicide formulation may be produced by adding an herbicide and an adjuvant or an adjuvant composition to a tank to create a mixture. An herbicide formulation that includes an herbicidally effective amount of an herbicide and an adjuvant or an adjuvant composition may be characterized by the herbicide and the adjuvant or the adjuvant composition being compatible with each other. Compatibility may be indicated by the mixture being homogeneous with little or no precipitate or exhibiting less than a 10%, 9%,8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, etc. Increase in mass of solid residue when the mixture is produced. Compatibility may be determined by solubility, stability, or potential for chemical interactions. In terms of solubility and homogeneity, compatibility may mean that the surfactant and herbicide remain evenly mixed without separating or forming layers, ensuring that the mixture can be uniformly applied. Homogeneity may ensure consistent distribution of the herbicide and adjuvant / adjuvant composition when applied. In terms of chemical stability, the adjuvant / adjuvant composition should not chemically react with the herbicide in a way that reduces the effectiveness of either component. Stability over time of the mixture may ensure effectiveness during application of the mixture. In terms of precipitation, precipitation may indicate poor compatibility as some of the components of the mixture are falling out of solution. Precipitation can clog nozzles and reduce the effectiveness of the herbicide application.

[0098] The degree of synergy or herbicidal effectiveness of an herbicide formulation may be affected by the amounts of each component in the formulation. Formulations with such synergies or herbicidal effectiveness may include 0.1 L / ha to 10 L / ha of at least one herbicide or herbicide composition and 0.01% v / v to 10% v / v of at least one adjuvant or adjuvant composition. Formulations with such synergies or herbicidal effectiveness may include 0.1 L / ha to 10 L / ha of at least one pre-emergent herbicide and 0.01% v / v to 10% v / v of at least one adjuvant. Formulations with such synergies or herbicidal effectiveness may include 0.1 L / ha to 10 L / ha of at least one post-emergent herbicide and 0.01% v / v to 10% v / v of at least one adjuvant. Formulations with such synergies or herbicidal effectiveness may include 0.1 L / ha to 10 L / ha of at least one pre-emergent herbicide and 0.1 L / ha to 10 L / ha of at least one post-emergent herbicide and 0.01% v / v to 10% v / v of at least one adjuvant. Formulations may include one or more base ingredients, one or more additives, and / or one or more additional adjuvants, with each component comprising between 0.01% v / v and 10% v / v of the formulation, or collectively making up 0.01% v / v to 10% v / v of the formulation.

[0099] The adjuvant or the adjuvant composition containing the adjuvant may be 0.01% v / v to 100% v / v of the herbicide formulation. The adjuvant or the adjuvant composition containing the adjuvant may be 0.1% v / v to 100% v / v of the herbicide formulation. The adjuvant or the adjuvant composition containing the adjuvant may be 0.01% v / v to 80% v / v of the herbicide formulation. The adjuvant or the adjuvant composition containing the adjuvant may be 0.1% v / v to 80% v / v of the herbicide formulation. The adjuvant or the adjuvant composition containing the adjuvant may be 0.01% v / v to 10% v / v of the herbicide formulation. The adjuvant or the adjuvant composition containing the adjuvant may bepresent at a concentration of 0.01% v / v to 10% v / v of the herbicide formulation that includes water. The adjuvant or the adjuvant composition containing the adjuvant may be 0.1% v / v to 10% v / v of the herbicide formulation. The adjuvant or the adjuvant composition containing the adjuvant may be 0.01% v / v to 5% of the herbicide formulation. The adjuvant or the adjuvant composition containing the adjuvant may be 0.1% v / v to 5% of the herbicide formulation. In some examples, the herbicide formulation may include 0.01% v / v to 100% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the herbicide formulation may include 0.1% v / v to 100% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the herbicide formulation may include 0.01% v / v to 80% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the herbicide formulation may include 0.1% v / v to 80% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the herbicide formulation may include 0.01% v / v to 10% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the adjuvant may be present at a concentration of 0.01% v / v to 10% v / v in water within the herbicide formulation. In some examples, the herbicide formulation may include 0.1% v / v to 10% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the herbicide formulation may include 0.01% v / v to 5% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the herbicide formulation may include 0.1% v / v to 5% v / v of an amphoteric surfactant, such as trialkyl ammonium propanoate. In some examples, the amphoteric surfactant is 0.01% v / v to 5% v / v of the herbicide formulation. In some examples, the amphoteric surfactant is 0.01% v / v to 80% v / v of the herbicide formulation. In some examples, the amphoteric surfactant is less than 1% v / v of the herbicide formulation.

[0100] The herbicide formulation may include an adjuvant composition and other components, such as one or more additives, one or more base ingredients, and / or one or more additional adjuvants.

[0101] In some examples, the herbicide formulation may include one or more additives. Examples of additives include water, oil, solvents, preservatives, stabilizers, antioxidants, acidifiers, chelates, complexing agents, hydrotropes, clarifiers, anti-freezing agents, antifoams, anti-drift agents, dyes, rheology modifiers, surfactants, emulsifiers, dispersants, wetting agents, humectants, penetrants, buffers, thickeners, defoamers, and UV protectants. The additive may be a non-copolymer. The additive may be an oil, an acid, a resin, and a polyol. The additive may be a mineral oil, seed oil, an acid, a resin, or a polyol. The additivecan increase the residual of pre-emerging herbicides in the soil, prolonging the clean field for sprouting of the crop of interest. In some examples, the additive is a mineral oil.

[0102] The additive may cooperate or enhance the adjuvant and / or herbicide formulation to enhance the residual activity of the herbicide formulation. Adding the additive to a surfactant can significantly improve the performance of the surfactant in herbicide applications by optimizing surface tension, enhancing spreading and coverage, and improving overall efficacy and stability on plant surfaces. The additive may lower the surface tension of the adjuvant and / or herbicide formulation and improve wetting and spreading on plant surfaces, which may enhance the effectiveness of herbicide applications. The combined or synergistic effect of the adjuvant and the additive can bring the surface tension closer to the ideal range (e.g., around 25-30 mN / m) for herbicide applications, ensuring better adhesion and penetration. The additive can alter the viscosity of the surfactant, emulsify the herbicide formulation, enhance the rainfastness and persistence of an herbicide on plant surfaces, and change the compatibility between the adjuvant composition with the herbicide.

[0103] An additive may be considered a base ingredient if it forms the bulk of a formulation. In some examples, the herbicide formulation may include one or more base ingredients or additives that can be considered base ingredients. The base ingredient may serve as the foundational substance in which the adjuvant is mixed, providing support for the overall structure and function of the adjuvant composition and / or herbicide formulation. The base ingredient may be a carrier used to carry and deliver active ingredients, such as a surfactant and / or an herbicide, to the target area. The carrier may ensure even distribution and application of the active ingredient across the target area.

[0104] In some examples, the herbicide formulation may include one or more additional adjuvants. Examples of additional adjuvants include surfactants, oils, acids, resins, and polyols. The additional adjuvant may include one or more anionic surfactant, non-ionic surfactant, amphoteric surfactant, mineral oil, seed oil, an acid, a resin, or a polyol. In some examples, the additional adjuvant may include mineral oil. The herbicide formulation can contain other surfactants added by means of simple mixture with the aforementioned amphoteric surfactant. The most common examples are: ethoxylated alkyl ethers, phosphated ethoxylated alkyl ethers, ethoxylated alkyl etheramines, alkylpolyglucosides, ethoxylated alkylpolyglucosides, ethoxylated imidazolines, polysiloxane derivatives, alkyl dimethyl amine oxides, alkyl dimethyl betaines, alkyl amido propyl amines and ethoxylated alkyl amines.

[0105] The herbicide and the adjuvant composition can be mixed can be mixed in a blending tank, a spray tank, a container, or an inline irrigation system to produce the herbicide formulation.

[0106] The herbicide formulation may be applied to plants, weeds, soil, urban areas, and forests. The herbicide formulation can be applied directly on the soil prior to planting the crop, after planting the crop, or both. The herbicide formulation can be formulated in various forms, such as liquids, soluble powders (SPs), dusts, pellets, tablets, foams, capsules, such as a suspension concentrate (SC), emulsifiable concentrate (EC), water-dispersible granule (WG), soluble concentrate (SL), wettable powder (WP), granule (GR), microemulsion (ME), capsule suspension (CS), paste (PA), aerosol (AE), dry powder (DP), soluble liquid (SL), water-dispersible concentrate (DC), gel (GL), effervescent tablet (ET), controlled release formulation (CR), suspended capsule (CS), oil dispersion (OD), concentrated suspension for seed treatment (FS), or aqueous dispersion (AD). Depending on the form of the herbicide formulation, application may be performed by spreader, hand, sprayers, etc. The herbicide formulation may be applied to an environment (e.g., plants, weeds, soil, urban areas, and forests) via an apparatus, such as an air-assisted sprayer, a conventional sprayer, an ultra-low volume equipment, such as aerial, electrostatic, foggers, and misting spray equipment, and chemigation systems, pivots, sprinklers, and combinations thereof.

[0107] The system for controlling a population of unwanted vegetation may include an herbicide formulation and soil as a medium for growing a crop of interest. The adjuvant, adjuvant composition, and herbicide formulation may be applied to a variety of vegetation and soil.

[0108] The Using the United States Department of Agriculture (USDA) soil taxonomy system classifies soils based on their properties and formation processes. Using the USDA soil taxonomy system, the soil may belong to any soil order, such as mollisols and oxisols, which are at different ends of the soil spectrum.

[0109] Mollisols may be characterized as fertile soils with a thick, dark surface horizon (mollic epipedon) rich in organic matter and may be found in grassland regions. Mollisols may be high productive for agriculture and may be found in major crop-producing regions like the Great Plains. An example of a mollisol is a loamy soil. Oxisols may be characterized as highly weathered soils found in tropical regions and may have a low nutrient content due to extensive leaching and accumulation of iron and aluminum oxides. Oxisols may have limited agricultural use, requiring significant management and fertilization. Anexample of an oxisol is latosol. Loamy soils may be balanced mixtures of sand, silt, and clay, and latosols may be clay-dominated and rich in oxides.

[0110] An example of a mollisol is Bonnie Silt Loam soil. Bonnie Silt Loam soil may be found in the United States, such as the Midwest. The soil may be described as a silty loam with a balanced mixture of silt and loam. The soil may have high fertility and good water retention and be suitable for growing crops, such as corn, soybeans, and wheat. In terms of agricultural use, Bonnie Silt Loam soil may be highly productive due to its nutrient-holding capacity and balanced drainage.[oni] An example of an oxisol is Dystroferric Yellow Latosol soil. Dystroferric Yellow Latosol soil may be found in tropical regions, such as parts of Brazil. The soil may described as highly weathered, acidic, and rich in iron and aluminum oxides. The soil may be poor in nutrients and organic matter but can be productive with proper management. In terms of agricultural use, Dystroferric Yellow Latosol soil may require significant input of lime and fertilizers to improve productivity and may be suitable for crops like coffee, sugarcane, and certain fruits when managed correctly.

[0112] Unwanted vegetation, such as weeds, can belong to various plant families, such as Poaceae (Grass family), Amaranthaceae (Amaranth family), and Commelinaceae (Spiderwort family).

[0113] Grasses in the Poaceae or grass family may be found in lawns, pastures, and fields; they may have narrow leaves and fibrous root systems. Grasses may prefer well-drained, loamy, or sandy soils but can also tolerate compacted or less fertile soils. Grasses may thrive in disturbed soils and may be common in lawns, pastures, and fields. Grasses such as crabgrass and goosegrass can compete aggressively with crops like com, soybeans, and wheat. They may be problematic in no-till systems where soil disturbance is minimal.

[0114] Plants in Amaranthaceae (Amaranth) family may have alternate leaves and can be herbaceous or shrubby. Amaranth weeds may prefer well-drained, fertile soils but can also tolerate a range of soil types, including disturbed soils and those with lower fertility. They may compete with crops like soybeans, corn, and cotton. Their rapid growth and high seed production can make them particularly troublesome.

[0115] Plants in Commelinaceae (Spiderwort) family may have succulent stems and showy flowers. Weeds like Benghal dayflower may thrive in moist, well-drained soils but can also grow in less favorable conditions. These weeds can be problematic in a range of crops, including vegetables and row crops. Their spreading nature can quickly cover crops and reduce yields.

[0116] Examples of weeds from the Poaceae (Grass) family include digitarius insularis and eleusine indica. Digitarius insularis is a type of grass typically found in tropical and subtropical regions and known for its resilience and ability to thrive in various environmental conditions. Eleusine indica is a common weed found in tropical and subtropical regions, known for its fast growth and adaptability, often invading agricultural fields and lawns, and recognized for its high tolerance to various herbicides.

[0117] An example of Commelinaceae (Spiderwort) family is Commelina benghalensis. Commelina benghalensis is a creeping herbaceous plant found in tropical and subtropical areas. It has distinctive blue flowers and is known for its rapid growth and ability to cover the ground, making it a common weed in many regions.

[0118] An example of Amaranthaceae (Amaranth) family is Amaranthus rudis Sauer. Amaranthus rudis Sauer is a highly competitive weed found in agricultural fields, gardens, and disturbed areas. It's known for its rapid growth and ability to thrive in various conditions. The plant can be quite invasive and is often difficult to control.

[0119] Experimental Studies

[0120] When assessing the residual activity of the herbicide formulation with or without the adjuvant or adjuvant composition that contains the adjuvant, the weed control (%) of a selected herbicide without any adjuvant, with an adjuvant not having general formula (I), or with adjuvant having general formula (I) was ascertained. An adjuvant not having general formula (I) may be designated as adjuvant 1, adjuvant 2, or adjuvant 3. An adjuvant not having general formula (I) may be commercially available or a comparative formulation designed or selected to serve as a point for comparison to test the performance of the adjuvant having general formula (I). When assessing phytotoxicity of the herbicide formulation with or without the adjuvant / adjuvant composition, the phytotoxic effects were observed in the unwanted vegetation, and no or minimal phytotoxic effects were observed in the soybean crop.

[0121] Example 1

[0122] When mixed in a tank, the adjuvant or adjuvant composition containing the adjuvant should be compatible with the selected herbicide(s). The herbicide(s) may be a pre-emergent or post-emergent herbicide. The herbicides may include atrazine, mesotrione, imazetapyr, sulfentrazone, S-metolachlor, or glyphosphate. The adjuvant may be a surfactant, such as amphoteric surfactant, or an adjuvant composition that includes the surfactant. The adjuvant may be an amphoteric surfactant having general formula (I) or an adjuvant composition that includes the surfactant having general formula (I).

[0123] This example was designed to illustrate that, as long as it contains an herbicide with a pre-emergent mode of action to combat unwanted vegetation, other herbicides or pest control compounds can be added to the tank mix, creating a versatile solution for the simultaneous control of various pests. In this mixture, the amphoteric adjuvant can be added to enhance the efficacy of the pre-emergent herbicide without altering the appearance of the prepared solution.

[0124] Table 2 records the observations of precipitation or homogeneity of different herbicide formulations with or without an adjuvant or adjuvant composition containing the adjuvant. The adjuvant composition may include the adjuvant and mineral oil. The observation of appearance of the mixture was recorded after 2 hours of the components of the mixture being added to the tank. Each observation was taken after a sample of the mixture was added in a tube and the tube was subjected to ten inversions.Table 2. Compatibility of Adjuvant with Pre-Emergent Herbicides in Tank Mix

[0125] The adjuvant appeared to be suitable for use in tank mixtures with atrazine, mesotrione, glyphosate, imazetapyr, sulfentrazone, and S-metolachlor. The addition of the adjuvant did not appear to have an adverse effect on the mixture, such as producing aprecipitate when the mixture without the addition of the adjuvant did not have a precipitate. A tank mixture of mesotrione and mineral oil precipitated, but such tank mixture with the adjuvant was completely homogenous with no precipitate. Although some mixture presented intrinsic precipitates from the formulation, the adjuvant did not appear to significantly change the mass of solid residue remaining on a 75-micron sieve after 24 hours. The mass of solid residue test may be performed by allowing the mixture to stand for 24 hours, pouring the mixture through the 75-micron sieve to capture any particles that have precipitated, rinsing the sieve, and weighing the dried sieve for comparison with initial weight of the empty sieve. If the mass of solid residue did not significantly change, it may suggest that the adjuvant and herbicide mix did not precipitate or form additional solids. This may indicate good compatibility in terms of maintaining a homogeneous mixture and avoiding nozzle clogging. An increase in solid residue may indicate precipitation, suggesting poor compatibility. This could lead to application issues and reduced effectiveness.

[0126] As shown in the examples below, the adjuvant having general formula (I) or an adjuvant composition that contains the adjuvant having general formula (I) may be an uptake enchancer for herbicides and as a tank mix adjuvant may increase S-metolachlor pre- em ergent herbicide residue in soil.

[0127] Example 2

[0128] The control of different unwanted vegetation digitaria insularis, eleusine indica, and commelina benghalensis in dystroferric yellow latosol soil by S-metolachlor 960 EC (1200 mL / ha) without any adjuvant, with adjuvant 1, and an adjuvant having general formula (I) were studied. S-metalachlor 960 EC (1200 mL / ha) may indicate that the product formulation is an emulsifiable concentrate (eC) with 960 grams of active ingredient per liter (g / L) and the recommended application rate of the product may be 1200 mL / ha. Weed control was evaluated by attributing visual scores, where 0% represents the absence of weed control and 100% represents the death of all weeds.

[0129] FIGS. 1 A-C show plots of the weed control (%) of different unwanted vegetation using S-metolachlor 960 EC (1200 mL / ha) without any adjuvant, with adjuvant 1 (0.2% v / v), and with an adjuvant having general formula (I) (0.2% v / v). FIG. 1 A shows a plot of the weed control (%) of digitaria insularis without any adjuvant, with adjuvant 1 (0.2% v / v), and an adjuvant having general formula (I) (0.2% v / v). FIG. IB shows a plot of the weed control (%) of eleusine indica by S-metolachlor 960 EC (1200 mL / ha) without any adjuvant, with adjuvant 1 (0.2% v / v), and an adjuvant having general formula (I) (0.2% v / v). FIG. 1C shows a plot of the weed control commelina benghalensis by S-metolachlor 960 EC (1200mL / ha) without any adjuvant, with adjuvant 1 (0.2% v / v), and an adjuvant having general formula (I) (0.2% v / v).

[0130] Pre-emergent herbicide S-metolachlor 960 EC (1200 mL / ha) with an adjuvant having the general formula (I) exhibited at least 90% control of digitaria insularis for at least 42 days compared to 14 days without an adjuvant. Pre-emergent herbicide S-metolachlor 960 EC (1200 mL / ha) with an adjuvant having general formula (I) exhibited at least 90% control of eleusine indica for at least 28 days compared to 14 days without an adjuvant. Pre-emergent herbicide S-metolachlor with an adjuvant having general formula (I) exhibited at least 90% control of commelina benghalensis for at least 14 days compared to about 7 days without an adjuvant. Adjuvant having general formula (I) appeared to perform just as well, if not better, than the adjuvant 1 The adjuvant with the general formula (I) allowed a pre-emergent herbicide that is not normally used in a certain type of soil to control weed growth. The adjuvant with the general formula (I) appeared to be able to extend the duration of weed control for at least twice the amount of time, for example, from 7 days to 14 days, 14 days to 28 days, 14 days to 42 days, etc.

[0131] The pre-emergent S-metalachlor 960 EC (1200 mL / ha) is not usually effective in dystroferric yellow latosol soil, and the use of the adjuvant having the general formula (I) with pre-emergent caused the pre-emergent to be more effective in weed control of digitaria insularis by extending weed control from 14 days to 42 days.

[0132] Example 3

[0133] The phytotoxicity to the soybean crop by subjecting in vegetation dystroferric yellow latosol soil to no treatment, treatment with only S-metolachlor 960 EC (1200 mL / ha), treatment with S-metolachlor 960 EC (1200 mL / ha) and adjuvant 1 and treatment S- metolachlor 960 EC (1200 mL / ha) with an adjuvant having general formula (I) (0.2% v / v) were studied. S-metalachlor 960 EC (1200 mL / ha) may indicate that the product formulation is an emulsifiable concentrate (eC) with 960 grams of active ingredient per liter (g / L) and the recommended application rate of the product may be 1200 mL / ha. Phytotoxicity was evaluated by attributing visual scores, where 0% represents the absence of crop injury and 100% represents the death of all crops.

[0134] Fig. 2A-D show photographs of vegetation that includes weeds and the soybean crop after 49 days of application of different treatments that show differences in weed control and phytotoxicity to the soybean crop. FIG. 2A shows a photograph of untreated vegetation (no herbicide, no adjuvant). Vegetation not treated by any herbicide or adjuvant shows an overgrowth of weeds between the the soybean crop. FIG. 2B shows a photograph ofvegetation treated with only S-metalachlor 960 EC (1200 mL / ha). Vegetation treated with only the herbicide shows improved weed control over untreated vegetation. FIG. 2C shows a photograph of vegetation treated with S-metolachlor 960 EC (1200 mL / ha) and adjuvant 1 (0.2% v / v). FIG. 2D shows a photograph of vegetation treated with S-metolachlor 960 EC (1200 mL / ha) and adjuvant having general formula (I) (0.2% v / v). As shown in FIGS. 2C and 2D, both adjuvant 1 and adjuvant having general formula (I) show an improvement in weed control over vegetation that is only treated with the herbicide, and obviously, over untreated vegetation. The adjuvant having general formula (I) may cause no or minimal phytotoxicity in the crop of interest.

[0135] Example 4

[0136] The control of unwanted vegetation Amaranthus rudis Sauer in Bonnie Silt Loam soil after 15 days, 41 days, and 66 days of application of S-metolachlor 83.7% EC (1.7 pt / A) without any adjuvant, with adjuvant 1, an adjuvant having general formula (I), adjuvant 3, and adjuvant 2 were studied. S-metolachlor 83.7% EC (1.7 pt / A) may be an emulsifiable concentrate (EC) with 83.7% active ingredient S-metolachlor by weight and has a recommended application rate of 1.7 pints per acre. Adjuvant 1 may be a blend of hexahydric alcohol ethoxylates, Cl 8-20 fatty acids, aliphatic hydrocarbon oils, and alkanolamides, such as that in GROUNDED®, available from Helena Agri -Enterprises, LLC, Collierville, Tennessee. Weed control was evaluated by attributing visual scores, where 0% represents the absence of weed control and 100% represents the death of all weeds.

[0137] FIG. 3 shows bar graphs of the weed control (%) of Amaranthus rudis Sauer using S- metolachlor 83.7% EC (1.7 pt / A) without any adjuvant, with adjuvant 1 (1% v / v), with an adjuvant having General Formula (I) (0.2% v / v), with adjuvant 3 (0.4% v / v), and with adjuvant 2 (0.2% v / v) after 15 days, 41 days, and 66 days of application of a particular weed control treatment.

[0138] After 15 days of applying different weed control treatments to vegetation, the weed control treatment of S-metolachlor 83.7% EC (1.7 pt / A) with an adjuvant having General Formula (I) (0.2% v / v) demonstrated superior weed control over all other treatments by exhibiting 98% weed control or suppressing the population of Amaranthus rudis Sauer to 2% of a population Amaranthus rudis Sauer in vegetation that is untreated (no herbicide, no adjuvant). The other treatments exhibited 96% or 97% weed control.

[0139] After 41 days of applying different weed control treatments to vegetation, the weed control treatment of S-metolachlor 83.7% EC (1.7 pt / A) with an adjuvant having General Formula (I) (0.2% v / v) demonstrated superior weed control over most treatments and sameweed control as S-metolachlor 83.7% EC (1.7 pt / A) with adjuvant 2 (0.2% v / v) by exhibiting 94% weed control or suppressing the population of Amaranthus rudis Sauer to 6% of a population Amaranthus rudis Sauer in vegetation that is untreated (no herbicide, no adjuvant). The other treatments exhibited 88%, 90%, and 92% weed control.

[0140] After 66 days of applying different weed control treatments to vegetation, the weed control treatment of S-metolachlor 83.7% EC (1.7 pt / A) with an adjuvant having General Formula (I) (0.2% v / v) demonstrated superior weed control over all other treatments by exhibiting 88% weed control or suppressing the population of Amaranthus rudis Sauer to 12% of a population Amaranthus rudis Sauer in vegetation that is untreated (no herbicide, no adjuvant). The other treatments exhibited 66%, 79%, 84%, and 86% weed control.

[0141] Note that the adjuvant having general formula (I) (0.2% v / v) was applied at a dosage or concentration 5 times lower than adjuvant 1 (1% v / v) and 2 times lower than adjuvant 3 (0.4% v / v), and adjuvant having general formula (I) (0.2% v / v) had better weed control over these adjuvants not having General Formula (I).

[0142] Example 5

[0143] The phytotoxicity to the crop of interest by subjecting vegetation in bonnie silt loam soil to no treatment, treatment with only S-metolachlor 83.7% EC (1.7 pt / A), treatment with S-metolachlor 83.7% EC (1.7 pt / A) and adjuvant 1, and treatment S-metolachlor 83.7% EC (1.7 pt / A) with an adjuvant having general formula (I) (0.2% v / v) were studied. S- metolachlor 83.7% EC (1.7 pt / A) may be an emulsifiable concentrate (EC) with 83.7% active ingredient S-metolachlor by weight and has a recommended application rate of 1.7 pints per acre. Adjuvant 1 may be a blend of hexahydric alcohol ethoxylates, Cl 8-20 fatty acids, aliphatic hydrocarbon oils, and alkanolamides. Phytotoxicity was evaluated by attributing visual scores, where 0% represents the absence of crop injury and 100% represents the death of all crops.

[0144] Fig. 4A-D show photographs of vegetation that includes weeds and the soybean crop after 41 days of application of different treatments that show differences in weed control and no phytotoxicity to the soybean crop. FIG. 4A shows a photograph of untreated vegetation (no herbicide, no adjuvant). Vegetation that is not treated by any herbicide or adjuvant shows an overgrowth of weeds in between the soybean crop. FIG. 4B shows a photograph of vegetation treated with only S-metalachlor 83.7% EC (1.7 pt / A). Vegetation treated with only the herbicide shows improved weed control over untreated vegetation. FIG. 4C shows a photograph of vegetation treated with S-metolachlor 83.7% EC (1.7 pt / A) and adjuvant 1 (1% v / v). Comparing FIGS. 4B and 4C, it is questionable whether the addition of commerciallyavailable adjuvant 1 (1% v / v) to S-metolachlor 83.7% EC (1.7 pt / A) shows any improvement in weed control. FIG. 4D shows a photograph of vegetation treated with S-metolachlor 83.7% EC (1.7 pt / A) and adjuvant having general formula (I) (0.2% v / v). As shown in FIG. 4D, the adjuvant having general formula (I) shows superior weed control over all other treatments including adjuvant 1 (1% v / v). Note that the adjuvant having the general formula (I) (0.2% v / v) was applied at a dosage or concentration 5 times lower than adjuvant 1 (1% v / v). Another observation is that there appears to be no loss in the crop of interest that is treated with S-metolachlor 83.7% EC (1.7 pt / A) and adjuvant having general formula (I) (0.2% v / v) compared to other treatments. The adjuvant having the general formula (I) does not appear to be phytotoxic to the crop of interest compared to the other treatments. The adjuvant having general formula (I) may cause no or minimal phytotoxicity in the crop of interest.

[0145] The following clauses illustrate example subject matter described herein.

[0146] Clause 1. An herbicide formulation comprising: an herbicidally effective amount of an herbicide and an adjuvant composition, the herbicide comprises a pre-emergent herbicide, the adjuvant composition comprising a non-copolymer base ingredient and an amphoteric surfactant, the amphoteric surfactant having general formula (I) R1— (XR2)m— N+(R3)(R4) — CEE — CH(R5) — COO- (I) where R1is hydrogen or ahydrocarbyl group, each X is independently a heteroatom-containing functional group, each R2is independently a hydrocarbyl group, m is an integer, R3and R4are independently hydrogens or hydrocarbyl groups, R5is hydrogen or a hydrocarbyl group, the amphoteric surfactant being 0.01% v / v to 5% v / v of the herbicide formulation, and the herbicide formulation having a soil residual life of at least 7 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 7 days.

[0147] Clause 2. The herbicide formulation of Clause 1, wherein R1is hydrogen or Ci- is hydrocarbyl group, each X is independently an ether, thioether, sulfoxide, ester, thioester, or amide group, each R2is independently a C3-6 chain, m is a number from 0 to 8 such that the number of carbon atoms in R1— (XR2)mis from 8 to 24, R3and R4are independently hydrogens or C1.4 chains, and R5is hydrogen or a methyl group.

[0148] Clause 3. The herbicide formulation of any one of Clauses 1 or 2, wherein the herbicide formulation has a soil residual life of at least 14 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 14 days.

[0149] Clause 4. The herbicide formulation of any one of Clauses 1 through 3, wherein the herbicide formulation has a soil residual life of at least 28 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 28 days.

[0150] Clause 5. The herbicide formulation of any one of Clauses 1 through 4, wherein the herbicide formulation has a soil residual life of at least 41 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 41 days.

[0151] Clause 6. The herbicide formulation of any one of Clauses 1 through 5, wherein the herbicide formulation has a soil residual life of at least 66 days to maintain a population of unwanted vegetation to not more than 30% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 66 days.

[0152] Clause 7. The herbicide formulation of any one of Clauses 1 through 6, wherein the non-copolymer base ingredient is at least one of a seed oil, a mineral oil, an acid, and a polyol.

[0153] Clause 8. The herbicide formulation of any one of Clauses 1 through 7, wherein the herbicide comprises at least one of an atrazine, a mesotrione, an imazetapyr, a sulfentrazone, or an S-metolachlor.

[0154] Clause 9. The herbicide formulation of any one of Clauses 1 through 7, wherein the herbicide comprises mesotrione, the non-copolymer base comprises 0.5% v / v mineral oil of the herbicide formulation, and the amphoteric surface is 0.4% v / v of the herbicide formulation.

[0155] Clause 10. The herbicide formulation of any one of Clauses 1 through 7, wherein the herbicide comprises mesotrione and glyphosate, the non-copolymer base comprises 0.5% v / v mineral oil of the herbicide formulation, and the amphoteric surface is 0.4% v / v of the herbicide formulation.

[0156] Clause 11. The herbicide formulation of any one of Clauses 1 through 7, wherein the herbicide comprises mesotrione and glyphosate, the non-copolymer base comprises 0.5% v / v mineral oil of the herbicide formulation, and the amphoteric surface is 0.4% v / v of the herbicide formulation.

[0157] Clause 12. The herbicide formulation of any one of Clauses 1 through 7, wherein the herbicide comprises a post-emergent herbicide.

[0158] Clause 13. The herbicide formulation of any one of Clauses 1 through 7, wherein the amphoteric surfactant is a trialkyl ammonium propanoate.

[0159] Clause 14. An adjuvant composition compatible with an herbicide in a tank mix, comprising a non-copolymer base ingredient and an amphoteric surfactant, the amphoteric surfactant having a surface tension of 30-45 mN / m, the amphoteric surfactant having general formula (I) R1— (XR2)m— N+(R3)(R4) — CH2 — CH(R5) — COO- (I) where R1is hydrogen or Ci-is hydrocarbyl group, each X is independently an ether, thioether, sulfoxide, ester, thioester, or amide group, each R2is independently a C3-6 chain, m is a number from 0 to 8 such that the number of carbon atoms in R1— (XR2)mis from 8 to 24, R3and R4are independently hydrogens or C1.4 chains, and R5is hydrogen or a methyl group, the adjuvant composition capable of forming a homogenous mixture with an herbicide that exhibits less than a 5% increase in mass of solid residue after being mixed with an herbicide, and the homogeneous mixture has a soil residual life of at least 7 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 7 days.

[0160] Clause 15. The adjuvant composition of Clause 14, wherein the amphoteric surfactant has a surface tension of 35-40 mN / m.

[0161] Clause 16. The adjuvant composition of any one of Clauses 14 or 15, wherein the amphoteric surfactant has a surface tension of 37 mN / m.

[0162] Clause 17. The adjuvant composition of any one of Clauses 14 through 16, wherein the amphoteric surfactant has a freezing point of -15 to -25 degrees Celsius, appears as a clear liquid at 25 degrees Celsius, has a density of 95 g / cm3 to 1.10 g / cm3, and has a flash point of at least 95 degrees Celsius.

[0163] Clause 18. The adjuvant composition of any one of Clauses 14 through 17, wherein the amphoteric surfactant has a freezing point of -21 degrees Celsius, appears as a clear liquid at 25 degrees Celsius, has a density of 1.03 g / cm3, and has a flash point of greater than 100 degrees Celsius.

[0164] Clause 19. A system for controlling a population of unwanted vegetation, comprising: an herbicide formulation comprising: an herbicidally effective amount of an herbicide and an adjuvant composition, the herbicide comprises a pre-emergent herbicide, the adjuvant composition comprising a non-copolymer base ingredient and an amphoteric surfactant, the amphoteric surfactant having general formula (I) R1— (XR2)m— N+(R3)(R4) — CH2 — CH(R5) — COO- (I) where R1is hydrogen or ahydrocarbyl group, each X is independently a heteroatom-containing functional group, each R2is independently a hydrocarbyl group, m is an integer, R3and R4are independently hydrogens or hydrocarbylgroups, R5is hydrogen or a hydrocarbyl group, and soil, the soil being a medium for growing a crop, the amphoteric surfactant being 0.01% v / v to 5% v / v of the herbicide formulation, the herbicide formulation having a soil residual life of at least 7 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 7 days, and the herbicide formulation having a phytotoxicity that reduces a population of a crop by no more than 10% of a population of a crop that is untreated by the herbicide formulation.

[0165] Clause 20. The system of Clause 19, further comprising unwanted vegetation, wherein the soil is at least one of dystroferric yellow latosol or bonnie silt loam, the unwanted vegetation is at least one of digitarius insularis, eleusine indica, commelina benghalensis, or amaranthus rudis sauer, and herbicide comprises at least one of an atrazine, a mesotrione, an imazetapyr, a sulfentrazone, or an S-metolachlor.

[0166] Clause 21. The herbicide formulation of any one of Clauses 1 through 6, wherein the non-copolymer base ingredient is selected from the group consisting of oils, acids, resins, and polyols.

[0167] Clause 22. The herbicide formulation of any one of Clauses 1 through 7, wherein the non-copolymer base ingredient is a mineral oil.

[0168] While the disclosure has been described in connection with what is presently considered to be the most practical and preferred embodiments, it is to be understood that the disclosure is not to be limited to the disclosed embodiments, but on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims, which scope is to be accorded the broadest interpretation so as to encompass all such modifications and equivalent structures as permitted under the law. Furthermore, it should be understood that while the use of the word preferable, preferably, or preferred in the description above indicates that feature so described may be more desirable, it nonetheless may not be necessary and any embodiment lacking the same may be contemplated as within the scope of the disclosure, that scope being defined by the claims that follow. In reading the claims it is intended that when words such as “a,” “an,” “at least one” and “at least a portion” are used, there is no intention to limit the claim to only one item unless specifically stated to the contrary in the claim. Further, when the language “at least a portion” and / or “a portion” is used the item may include a portion and / or the entire item unless specifically stated to the contrary.

Claims

CLAIMSWhat is claimed is:

1. An herbicide formulation comprising: an herbicidally effective amount of an herbicide and an adjuvant composition, the herbicide is substantially free of phosphorous atoms, the adjuvant composition comprising an amphoteric surfactant, the amphoteric surfactant having general formula (I)R1— (XR2)m— N+(R3)(R4)— CH2— CH(R5)— COO- (I) whereR1is hydrogen or ahydrocarbyl group, each X is independently a heteroatom-containing functional group, each R2is independently a hydrocarbyl group, m is an integer,R3and R4are independently hydrogens or hydrocarbyl groups, andR5is hydrogen or a hydrocarbyl group, and wherein the herbicide formulation is substantially free of copolymers.

2. The herbicide formulation of claim 1, wherein:R1is hydrogen or Ci-is hydrocarbyl group, each X is independently an ether, thioether, sulfoxide, ester, thioester, or amide group, each R2is independently a C3-6 chain, m is a number from 0 to 8 such that the number of carbon atoms in R1— (XR2)mis from 8 to 24,R3and R4are independently hydrogens or C1.4 chains, andR5is hydrogen or a methyl group.

3. The herbicide formulation of claim 1, wherein the herbicide formulation has a soil residual life of at least 14 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 14 days.

4. The herbicide formulation of claim 1, further comprising one or more additives, the one or more additives comprising water, oil, solvents, preservatives, stabilizers, antioxidants, acidifiers, chelates, complexing agents, hydrotropes, clarifiers, anti-freezing agents, antifoams, anti-drift agents, dyes, rheology modifiers, surfactants, emulsifiers, dispersants, wetting agents, humectants, penetrants, buffers, thickeners, defoamers, or UV protectants.

5. The herbicide formulation of claim 1, further comprising one or more additional adjuvants, the adjuvant comprising an anionic surfactant, a non-ionic surfactant, an amphoteric surfactant, a seed oil, a mineral oil, an acid, or a polyol.

6. The herbicide formulation of claim 1, wherein the amphoteric surfactant is a trialkyl ammonium propanoate in a concentration of 0.1% v / v to 100% v / v in the adjuvant composition.

7. The herbicide formulation of claim 1, wherein the herbicide comprises a pre-emergent herbicide.

8. The herbicide formulation of claim 1, wherein the herbicide comprises at least one of an atrazine, a mesotrione, an imazetapyr, a sulfentrazone, or an S-metolachlor.

9. The herbicide formulation of claim 1, further comprising one or more insecticides, fungicides, herbicides, desiccants, defoliants, acaricides, nutrients, miticides, bactericides, biocides, ovicides, nematicides, insect growth regulators, or plant growth regulators.

10. The herbicide formulation of claim 1, wherein the amphoteric surfactant is 0.01% v / v to 80% v / v of the herbicide formulation.

11. A method of preparing an herbicide formulation comprising: mixing an adjuvant composition and an herbicide substantially free of phosphorous atoms to produce the herbicide formulation, the adjuvant composition comprising an amphoteric surfactant, the amphoteric surfactant having general formula (I)R1— (XR2)m— N+(R3)(R4)— CH2— CH(R5)— COO- (I) whereR1is hydrogen or Ci-is hydrocarbyl group, each X is independently an ether, thioether, sulfoxide, ester, thioester, or amide group, each R2is independently a C3-6 chain, m is a number from 0 to 8 such that the number of carbon atoms in R1—(XR2)mis from 8 to 24,R3and R4are independently hydrogens or C1.4 chains, andR5is hydrogen or a methyl group, and wherein the herbicide formulation being substantially free of copolymers.

12. The method of claim 11, wherein the adjuvant composition forms a homogenous mixture with an herbicide that exhibits less than a 5% increase in mass of solid residue after being mixed with an herbicide, and wherein the homogeneous mixture has a soil residual life of at least 14 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 14 days.

13. The method of preparing the herbicide formulation of claim 11, wherein the wherein the amphoteric surfactant is a trialkyl ammonium propanoate.

14. The method of preparing the herbicide formulation of claim 11, wherein the adjuvant composition and the herbicide is mixed in a blending tank, a spray tank, a container, or an inline irrigation system.

15. The method of preparing the herbicide formulation of claim 11, wherein the adjuvant composition and the herbicide is mixed with one or more additional adjuvants to produce the herbicide formulation.

16. The method of preparing the herbicide formulation of claim 11, wherein the adjuvant composition and the herbicide is mixed with one or more additives to produce the herbicide formulation.

17. A method for controlling a population of unwanted vegetation in an environment, comprising: applying an herbicide formulation to the environment comprising: an herbicidally effective amount of an herbicide and an adjuvant composition, the herbicide comprises a pre-emergent herbicide, the adjuvant composition comprising an amphoteric surfactant, the amphoteric surfactant having general formula (I)R1— (XR2)m— N+(R3)(R4)— CH2— CH(R5)— COO- (I) whereR1is hydrogen or ahydrocarbyl group, each X is independently a heteroatom-containing functional group, each R2is independently a hydrocarbyl group, m is an integer,R3and R4are independently hydrogens or hydrocarbyl groups,R5is hydrogen or a hydrocarbyl group, wherein the herbicide formulation having a soil residual life of at least 7 days to maintain a population of unwanted vegetation to not more than 10% of a population of unwanted vegetation that is untreated by the herbicide formulation for at least 7 days, and wherein the herbicide formulation having a phytotoxicity that reduces a population of a crop by no more than 10% of a population of a crop that is untreated by the herbicide formulation.

18. The method of claim 17, further comprising unwanted vegetation, wherein the soil is at least one of dystroferric yellow latosol or bonnie silt loam, the unwanted vegetation is at least one of digitarius insularis, eleusine indica, commelina benghalensis, or amaranthus rudis sauer, and herbicide comprises at least one of an atrazine, a mesotrione, an imazetapyr, a sulfentrazone, or an S-metolachlor.

19. The method of claim 17, wherein the environment comprises plants, weeds, seeds, soil, urban areas, or forests, and wherein the herbicide is applied to the environment by one or more air-assisted sprayers, conventional sprayers, ultra-low volume equipment, aerial equipment, electrostatic equipment, foggers, and misting spray equipment, and chemigation systems, pivots, or sprinklers.

20. The method of claim 17, wherein the herbicide is substantially free of phosphorous atoms and the herbicide formulation is substantially free of copolymers.

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