WO2025245451A1

WO2025245451A1 - Agrochemical formulations comprising a pesticidally-active oxathiazolidine compound

Info

Publication number: WO2025245451A1
Application number: PCT/US2025/030779
Authority: WO
Inventors: Moira ESSON; Natalie C. Giampietro; Hui Han; Imre MEZEI; Ke Min; Scott O'NEAL; Dwain M. RULE; Bin Wei
Original assignee: Corteva Agriscience LLC
Current assignee: Corteva Agriscience LLC
Priority date: 2024-05-23
Filing date: 2025-05-23
Publication date: 2025-11-27
Anticipated expiration: 2026-11-23

Abstract

Disclosed herein are agrochemical formulations comprising the compound of Formula One. In particular, disclosed herein are solution-based agrochemical formulations of the compound of Formula One.

Description

AGROCHEMICAL FORMULATIONS COMPRISING A PESTICIDALLY-ACTIVE OXATHIAZOLIDINE COMPOUND

This disclosure pertains to the field of agricultural chemistry, specifically to innovative agrochemical formulations comprising the compound of Formula One having a unique chemical structure. The unique chemical structure of the compound of Formula One presents complex challenges in the development of an agrochemical formulation suitable for a variety of applications.

DETAILED DESCRIPTION

Disclosed herein are agrochemical formulations comprising a compound of Formula One.

Formula One

The compound of Formula One has pesticidal utility against pests in Phyla Arthropoda, Mollusca and Nematoda. The compound of Formula One and biological data are disclosed in WO2021/011722 Al. “Pesticidal utility” in this context means that the compound of Formula One having an observable effect on a pest, for example, the effects of necrosis, death, retardation, prevention, removal, destruction, or otherwise diminishing the occurrence and/or activity of a pest in a locus. This compound can be used to control, prevent, combat and/or eliminate pest infestations. The term “locus” means a habitat, breeding ground, plant, seed, soil, material, or environment, in which a pest is growing, may grow, or may traverse. For example, a locus may be where crops, trees, fruits, cereals, fodder species, vines, turf, and/or ornamental plants, are growing; where domesticated animals are residing; the interior or exterior surfaces of buildings (such as places where grains are stored); the materials of construction used in buildings (such as impregnated wood); and the soil around buildings. The compound of Formula One has useful agrochemical properties. Such agrochemically useful compounds, including the compound of Formula One, may need to be appropriately formulated for agrochemical use.

A variety of formulation types, for example, suspension concentrate (SC) formulations and flowable concentrate for seed treatment (FS) formulations, are known in the art, depending on how these compounds are applied to the crops or locus of the targeted pests. Considering the potential for a wide-scope of applications, a formulation that has desirable physical and chemical properties allowing for formulation stability, ease of formulation processing, and effective delivery of the compound of Formula One to a target surface is warranted.

In one aspect, the formulations disclosed herein are related to both aqueous and nonaqueous formulations of the compound of Formula One. Other substances may be added so that the agrochemical formulations comprising Formula One may be used at a required concentration and in an appropriate form, permitting ease of application, handling, transportation, and storage. The compound of Formula One has a unique structure, and distinct chemical and physical properties are imparted by its structure. For example, the compound of Formula One is a lipophilic molecule and it is less soluble in aqueous-based solutions. It comprises a 5-ring structure, and as such, a complex 3 -dimensional structure. In the context of formulations, its interactions with formulation components can present certain advantages and drawbacks As these outcomes are highly unpredictable, it is necessary to validate such effects using empirical data.

One aspect of the agrochemical formulations disclosed herein is a suspension concentrate (SC) formulation comprising the compound of Formula One. Another aspect of the agrochemical formulations disclosed herein is a flowable concentrate for seed treatment (FS) formulation comprising the compound of Formula One. There are several challenges associated with generating a suitable SC or FS formulation comprising the compound of Formula One. Conventional formulations disclosed in the art presented issues such as particle size growth, sedimentation, syneresis, degradation of active compounds leading to decreased effectiveness, difficulty in handling, increased challenges with formulation processing, and decreased shelflife.

The SC and FS formulations disclosed herein are designed to significantly improve the stability and delivery of active ingredients. “Stability” in this context refers to formulation concentrate or dilution being physically stable and chemically stable. In other words, there is an absence of appreciable change in characteristics and properties of the product at the time of manufacture and over shelf-life. For example, in one aspect, after storage at 54 °C for 2 weeks, the disclosed formulations comprising the compound of Formula One show that the change in particle size is less than 20% of the initial particle size. In some other aspect, after storage at 54 °C for 2 weeks, the disclosed formulations comprising the compound of Formula One show that the change in particle size is less than 10% of the initial particle size. In one aspect, after storage at 54 °C for 2 weeks, the disclosed formulations comprising the compound of Formula One show that the change in particle size is less than 5% of the initial particle size. In some instances, the change in the particle size is less than 4%. In some other instances, the change in particle size is less than 2%. In yet another instance, the change in particle size is less than 1%. “Delivery” in this context refers to increased adhesion, retention and/or spreading on a target surface. A target surface may include soil, a crop, or a seed. The innovative formulations encompass a unique combination of inert components and may include surfactants, polymers, dispersants, and wetting agents that synergistically enhance the dispersability and stability of suspended particles including the compound of Formula One in aqueous media.

One aspect of the agrochemical formulations disclosed herein is a formulation that is specifically engineered to prevent syneresis, hard-pack sedimentation, prevent particle size growth, reduce formulation viscosity, and that ensures a homogenous distribution of the active ingredient throughout the shelf-life of the product (i.e., the SC and FS formulations).

Another aspect of the agrochemical formulations disclosed herein is a formulation that can withstand adverse conditions such as UV exposure/irradiation.

Formulations other than SC formulations, including aqueous and non-aqueous formulations, are within the scope of the inventive formulations disclosed herein. For example, suspoemulsions (SE), suspension concentrate-capsule suspensions (ZC), emulsifiable concentrates (EC), and dispersible concentrates (DC) are within the scope of the formulations disclosed herein.

The term “pesticidal compound” or “pesticidal active” means an organic compound that is suitable for combating, eliminating, killing and/or controlling pests or a pest infestation that affect plants and crops, in particular pests of the Phyla Arthropoda, Mollusca and Nematoda. The formulation of pesticidal actives, particularly SC and FS formulations, requires careful consideration of the loading concentration of active compounds to ensure delivery, and stability. The loading concentration refers to the amount of active pesticidal ingredient relative to the total volume or weight of the formulation. It is a critical factor that influences the formulation’s performance, environmental impact, handling and storage. However, achieving optimal loading concentration is challenged by several factors, particularly, the unique structural properties of the active compounds.

Pesticidally active compounds vary widely in their chemical structures, which can significantly impact their solubility, stability and interaction with other formulation components. Depending on the unique properties of these active molecules, there are specific limitations to loading concentrations in certain formulations. For example, the inherent solubility of an active compound such as the compound of Formula One is a primary constraint in solvent-based formulations. An active compound with a low solubility in a given solvent system may precipitate out of solution, leading to an uneven distribution and reduced efficiency. This is particularly challenging in formulations that require high-loading concentrations for certain applications, such as seed treatment compositions and certain soil or in-furrow applications. In these instances, it is challenging to maintain a stable solvent-based homogeneous formulation. In another example, an active compound with high lipophilicity and complex three-dimensional structure may pose challenges with incorporation into aqueous systems, leading to formulation processing challenges. This is exacerbated in formulations that require high-loading concentrations. As used herein “pesticidally active” means an active ingredient or a pesticide that has an observable effect on a pest, for example, the effects of necrosis, death, retardation of growth, prevention, removal, destruction, or otherwise diminishing the occurrence and/or activity of a pest in a locus.

Some active compounds may also be prone to degradation or chemical changes when concentrated, which can be accelerated by factors such as pH, temperature, and exposure to light, in particular, UV light.

The structural properties of active compounds can affect the viscosity and flow characteristics of the formulation. High-loading concentrations might increase the viscosity to inoperable limits narrowing the scope of desired application or in some cases, completely hinder the application. On the other hand, very low viscosities of heterogenous liquid formulations may lead to sedimentation and phase separation (/.e., syneresis).

More importantly, the unique structural properties of the active compounds must be compatible with other ingredients in the formulation (e.g., surfactants, adjuvants). Incompatibilities can lead to flocculation, crystal growth, or sedimentation compromising the formulation’s stability and homogeneous distribution of active particles.

The development of a suspension concentrate formulation or flowable concentrate for seed treatment formulation of the compound of Formula One is challenging and presents specific challenges based on its unique structural properties. Given its lipophilic properties, this compound presents challenges in incorporating it into aqueous systems particularly at high- loading concentrations. High-loading concentrations, while desirable for reducing the application volume, exacerbate these challenges by increasing the risk of particle agglomeration or flocculation, crystal growth, sedimentation, formulation viscosity, and increased processing time. For example, it is challenging to wet the active into the pre-mill concentrate when developing formulations that require higher loading using conventional mill base approaches thereby increasing the processing time. Furthermore, its structural complexity and lipophilicity may interfere with its compatibility with other formulation components such as surfactants and adjuvants, necessitating a careful balance to achieve a stable and effective product. Identifying an optimal loading concentration for the compound of Formula One thus requires a nuanced understanding of its physicochemical properties and innovative approach to formulation design.

Some notable examples of commercial agrochemical suspension concentrate formulations are those of flufenacet, diflufenican, and cyfluthrin, which are highly lipophilic. The loading concentrations of these formulations range between 5-30% weight/weight showcasing the challenges associated with formulating certain lipophilic active compounds. In particular, loading concentrations of cyfluthrin, a synthetic pyrethroid, range from 5-10% weight/weight, reflecting the compound’s formulation challenges posed by its low water solubility.

Loading concentration, particularly in the context of suspension concentrates and flowable concentrates for seed treatment for pesticidally-active compounds, refers to the amount of active ingredient relative to the total volume or weight of the formulation. It is a critical parameter that affects stability, handling, and ease of application. The loading concentration can be measured or specified using many methods. The common methods are weight/weight percentage (%w/w) and weight/volume percentage (%w/v). The weight/weight percentage measurement is the most common method of specifying loading concentration, especially for solid active ingredients in the suspension. It expresses the mass of the active ingredient as a percentage of the total mass of the formulation. For example, a 20% w/w suspension concentrate means that 20 grams of active ingredient is present in 100 grams of the total formulation.

Weight/volume percentage is used when it is more convenient or relevant to consider the volume of the formulation, especially for liquid formulations. It represents the mass of the active ingredient in grams per 100 milliliters of the total formulation. This is particularly useful for formulations where the density of the solvent or carrier medium significantly influences the performance or application of the product. These concentrations can be measured using various analytical techniques known in the art such as gravimetric analysis, spectrophotometry, high- performance liquid chromatography (HPLC) and gas chromatography (GC).

In one aspect, disclosed herein is an agrochemical formulation comprising the compound of Formula One in which the compound of Formula One is present in a loading concentration of less than 80% w/w. In one aspect, the loading concentration is less than 70% w/w. In another aspect, the loading concentration is less than 60% w/w. In some other aspects, the loading concentration is less than 50% w/w. In some aspects, the loading concentration is less than 40% w/w. In other aspects, the loading concentration is less than 30% w/w. In some aspects, the loading concentration is less than 20% w/w. In some other aspects, the loading concentration is less than 10% w/w. In other aspects, the loading concentration is less than or equal to 5% w/w. In further aspects, the loading concentration is less than 1% w/w.

In some instances, the loading concentration depends on the application type. For example, in one aspect for seed treatment formulations and foliar applications, the loading concentration is from 0.8% w/w to 70% w/w. In a particular example for foliar applications, the loading concentration is from 1% w/w to 55% w/w. In another aspect for foliar applications, the loading concentration is from 1% to 40% w/w. In some particular aspects, for foliar applications, the loading concentration is 9% to 25% w/w. In some other aspects, for seed treatment applications, the loading concentration is 1% to40% w/w.

The loading concentration of the compound of Formula One can be expressed as ranges in %w/w. According, in some instances, the agrochemical formulations disclosed herein comprise the compound of Formula One between 0.5-70% w/w. In other instances, the agrochemical formulations disclosed herein comprise the compound of Formula One between 0.8-70% w/w. In some other instances, the agrochemical formulations disclosed herein comprise the compound of Formula One between 1-60% w/w. In other instances, the agrochemical formulations disclosed herein comprise the compound of Formula One between 1-50% w/w. In other instances, the agrochemical formulations disclosed herein comprise the compound of Formula One between 1-40% w/w. In some other instances, the agrochemical formulations disclosed herein comprise the compound of Formula One between 1-35% w/w. In some other instances, the agrochemical formulations disclosed herein comprise the compound of Formula One between 1-30% w/w.

In some particular aspects of foliar applications, for example, when the compound of Formula One is used as a pre-mix with other actives, the loading concentration of the compound of Formula One is between 2-5% w/w. In some other instances, the loading concentration of the compound of Formula One is between 3-5% w/w. In some instances, the loading concentration is between 3-4% w/w.

In some other aspects of foliar pre-mix applications, depending on the other actives in the premix, the loading concentration of the compound of Formula One is between 1-30% w/w. In some other instances, the loading concentration of the compound of Formula One is between 5- 25% w/w. In some instances, the loading concentration is between 10-20% w/w, In a specific instance, the loading concentration of compound of Formula One and the compound of Formula A shown below is between 8-15% w/w.

These loading concentrations are applicable to both aqueous and non-aqueous agrochemical formulations. Solid formulations, for example, water-dispersible granules (WG), or dry flowables (DF) can incorporate very high percentage of the compound of Formula One ranging from 50% to over 90% in some instances. Generally, solid formulations often allow for high concentrations of the compound of Formula One.

In certain aspects, the particle size of the compound of Formula One in the agrochemical formulations disclosed herein is less than 8 pm (Dv90). While the particle size of a particular active molecule may affect many aspects of the active molecule’s performance and formulation processability, this effect is highly unpredictable. Such effects are most likely caused by a variety of factors, including the unique structural features, physiochemical properties and interactions with the formulation components. Especially, compound of Formula One, a highly lipophilic and structurally complex molecule, reduced particle size presents a significant challenge in developing formulation compositions due to aggregation. There are literature reports related to reduced particle size compositions of certain agrochemicals, however, the physical properties are vastly different from those of the compound of Formula One. Preparing a stable composition of a reduced particle size composition of a compound of Formula One is particularly challenging, unexpected and surprising.

For example, it was found that formulations having particle size less than 8 pm (Dv90) have better spreading properties. “Spreading” in this context refers to increased surface area of droplet deposit after adherence to target surface, such as plant or leaf surface. In other words, “spreading” results in increased diameter of spray deposit in comparison to standard water droplet. This results in greater surface area coverage of active ingredient on leaf surface. “Active ingredient” in this context refers to compound of formula one. In some other aspects, the formulations disclosed herein have better retention properties. “Retention” in this context refers to spray adhesion, or droplet adhesion during spray droplet impact to target leaf surface which prevents droplet bounce-off and loss of active ingredient. Active ingredient in this context refers to the compound of Formula One. In some other aspects, the formulations disclosed herein have improved spreading and retention properties. Spreading and /or retention properties of a formulation are beneficial for certain agrochemical applications, such as foliar applications. In some aspects of the formulations disclosed herein, these beneficial properties are further enhanced by certain formulation components.

In some specific instances, the agrochemical formulations disclosed herein comprise compound of Formula One in particles size of less than or equal to 3 pm (Dv90). These formulations exhibit better spreading and/or retention properties in comparison with the formulations that have particle sizes larger than 3 pm (Dv90). In some specific instances, the agrochemical formulations disclosed herein comprise compound of Formula One in particle size of between 1 These formulations exhibit better spreading and/or retention properties in comparison with the formulations that have particle sizes larger than 1 pm (Dv90).

The particle size of the active ingredient is measured by two different techniques. For example, as used herein, the phrase "having an average particle size of less than 1 micron" refers to the active ingredient having the particle size as determined by both the Dv90 and Z-average of below 1 micron. The Dv50 and Z-average will be similar when the particle size is narrow and below 1 micron. The Z-average diameter of the active ingredient is measured by dynamic light scattering (z.e., photon correlation spectroscopy) using equipment readily determinable by those skilled in the art such as a Malvern Nanosizer and / or laser diffraction-based particle size assessment such as Malvern Mastersizer. The Dv90 and Dv50 particle size of the active ingredient is the particle size as determined using available analytical devices such as Malvern Mastersizer (z.t?., laser diffraction-based particle size assessment) or Malvern Nanosizer (i.e., photon correlation spectroscopy). In some aspects, the phrase “having an average particle size of less than 3 micron” as used herein refers to the active ingredient having the particle size determined by both the Dv90 and Z-average of below 3 micron. In some other aspects, the phrase “having an average particle size of less than 3 micron” refers to the active ingredient having the particle size determined by both the Dv90 and Z-average of below 3 micron. Static light scattering techniques will provide a volume weighted particle size distribution (Dv). This means that the contribution of each particle in the distribution relates to the volume of the particle. Dv90 is the 90th percentile of the cumulative volume distribution. For definition purposes, Dv90 less than 1 micron indicates that 90% of the distribution of particles by volume has a size less than 1 micron. Active ingredient in this context refers to the compound of Formula One.

The unexpected finding of benefits related to the particular particle sizes of the compound of Formula One offers several advantages; for example, suitable formulations can be prepared to meet the certain requirements of specific applications such as foliar applications, seed treatment applications, in furrow and soil applications.

It was found that certain formulation adjuvants interact with the compound of Formula One and exhibit certain desirable agrochemical properties. “Adjuvant” in this context refers to an inert ingredient added to a formulation that serves the role of increasing retention and/or spreading of an active ingredient. “Spreading” in this context refers to increased surface area of droplet deposit after adherence to leaf surface (i.e., increased coverage on target). “Retention” in this context refers to spray adhesion, or droplet adhesion during spray droplet impact to target surface (e.g., plant leaf in foliar application) which prevents droplet bounce-off and loss of active. “Retention” in this context may also refer to adherence / maintaining of active to target surface i.e., plant leaf in foliar application) after exposure to environmental factors, such as rain or wind. Accordingly, in certain instances, specific adjuvants increased the retention, spreading, or retention and spreading properties of the formulations disclosed herein by more than 10%; in certain other instances, by more than 20%; and in certain instances, more than 30%; in some instances, by more than 40% -50%, and in additional instances by greater than 50%. In some aspects, the spreading and/or retention properties depend on the particular adjuvant chemistry that is being used; for example, in some instances, polysorbate-based surfactants show unexpected beneficial effects in retention and/or spreading compared to other surfactants or control samples. In some other aspects, polysiloxane-based surfactants show unexpected beneficial effects in retention and/or spreading compared to other surfactants or control samples. In yet another instances, use of both polysorbate-based surfactants and poly siloxane-based surfactants show unexpected beneficial effects in retention and/or spreading compared to other surfactants or control samples.

Improved retention and spreading properties provided unexpected beneficial properties in the context of practical usage of the formulations disclosed herein. For example, in some aspects, the loading concentrations (dosage levels) of the compound of Formula One can be based on the application type or selected crops. For instance, in some aspects, the formulations disclosed herein are used as a foliar application. In these instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 0.5-70 percent weight per weight (%w/w). In some instances, the loading concentration is from 0.8%-70%w/w. In some other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of !%-60%w/w. In some instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 1%- 50%w/w. In some other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 1%- 40%w/w. In some specific instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 1%- 35%w/w. In some instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of !%-30%w/w. In some other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 1%-20%W/W. In some instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 10%w/w. In other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 20% w/w. In other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 23%w/w. In some other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 25%w/w. In other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 30%w/w. In some other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 35%w/w. In other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 40%w/w. In some other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 45% w/w. In some other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 50%w/w. In other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 55%w/w. In other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 60%w/w. In other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 65%w/w. In other instances, some formulations disclosed herein comprise the compound of Formula One in a loading concentration of 70%w/w.

In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%-18%W/W. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%-17%W/W. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%- 16% w/w. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%-15%W/W. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1% - 14%w/w . In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%-12%W/W. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%-11% w/w. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%-10%W/W. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in !%-9%w/w. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%-8%W/W. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%-7%W/W. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in !%-6%w/w. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%-5%W/W. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1%-4%W/W. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in 1% -3%w/w. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One in l%-2% w/w. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One less than l%w/w. In some instances, the formulations disclosed herein comprise a loading concentration of compound of Formula One is 0.8%w/w.

In certain aspects, the adjuvants disclosed herein are nonionic surfactants. Suitable nonionic surfactants are selected from the group consisting of ethyoxylated alkylphenols, ethoxylated fatty alcohols, alkoxylated fatty alcohols, alkyl polyglucosides, block copolymers of ethylene oxide and propylene oxide (poloxomers), sorbitan fatty acid ester ethoxylated (tweens) and fatty acid esters of sucrose. These nonionic surfactants have been selected based on their ability to enhance the dispersion, solubilization, and stability of the compound of Formula One and any other actives that may be present in the formulation. These adjuvants have been carefully selected to ensure their compatibility with a wide range of active ingredients and other formulation components.

Certain formulations disclosed herein comprise retention agents, and certain other formulations comprise spreading agents. In certain formulations, both retention agents and spreading agents are present.

The adjuvants are included in the formulations disclosed herein based on the specific application or as needed. As such, certain formulations disclosed herein do not comprise adjuvants, i.e., spreading and/or retention agents. For example, a certain crop specific treatment might not require the addition of the adjuvant. Or in some instances, certain commercial embodiment may not require such adjuvants. And some geographically-specific formulations may not comprise the adjuvants. The retention agents that can be used as adjuvants are selected from the group consisting of Carboxymethyl cellulose (CMC): A cellulose derivative with carboxymethyl groups (-CH2- COOH) bound to some of the hydroxyl groups of the glucopyranose monomers that make up the cellulose backbone. It is often used due to its high viscosity and non-toxic nature.

Ethyl hydroxy ethyl cellulose (EHEC): A cellulose derivative that has both ethyl groups (CH3-CH2-) bound to some hydroxyl groups of the glucose pyranose monomers. There are also hydroxy ethyl. It is used due to its high viscosity and low toxicity.

Polyvinyl alcohol (PVA): A synthetic polymer which is biodegradable and possesses excellent film-forming, emulsifying, and adhesive properties. It is commonly used in papermaking, textiles, and various coatings.

Starch-based polymers: Natural polymers derived from starch that can be chemically or physically modified to enhance their properties as retention agents. They are biodegradable and widely used in the paper industry.

Gum arabic: A natural gum made of the hardened sap of various species of the acacia tree. It is soluble in water and used as a stabilizer in food industry, as well as in pharmaceuticals and cosmetics.

Alginates: Salts of alginic acid, which is a polysaccharide distributed widely in the cell walls of brown algae. They have the ability to absorb water quickly, forming a gel which makes them effective as retention agents.

Polyacrylamides (PAMs): Synthetic, high molecular weight polymers which are highly water-absorbent and form soft gels when hydrated. They are used extensively in water treatment processes and as flocculants.

Bentonite clay: A natural clay with a fine, soft texture. It forms a paste when mixed with water and is known for its property to remove impurities. It is used in various industrial applications including as a retention agent in drilling and for purification.

Guar gum: A natural gum extracted from the guar bean. It has thickening and stabilizing properties and is used in a wide range of industries, including food, pharmaceutical, and cosmetics. Polyethyleneimine (PEI): A highly branched polymer used in papermaking and water treatment as a retention aid due to its high cationic charge density.

Microparticles: Specifically engineered inorganic or organic particles that can enhance retention by forming a network with the fibers or particles in a formulation. Silicon dioxide (silica) and polymethylmethacrylate (PMMA) microparticles are common examples.

Polysorbates: Ethoxylated sorbitan ester surfactants that are effective in reducing surface tension, thus enhancing the spreading as well as retention of agrochemical formulations.

Ethoxylated fatty alcohols: Ethoxylated alcohols are an important class of non-ionic surfactants that are produced by a stepwise additive reaction of fatty alcohols with ethylene oxide in the presence of catalysts. These surfactants are effective in reduction of surface tension resulting in enhanced spreading and/or retention of agrochemical formulations.

The following can be classified as hydrophobic liquids that may not be nonionic surfactants. However, they can be used as retention agents.

Fatty acid amides: Fatty acid amides, or di -substituted amides, are non-ionic components that increase surface elasticity resulting in increased retention and also impact the droplet deposit. Examples are Hallcomid M-10 and Hallcomid M-8-10.

Methylated seed oils: Methylated seed oils are vegetable oils that have been modified through a process of esterification. Methylated seed oils increase spray droplet size and alter the dynamic surface tension of the solution such that it prevents breaking of water droplets during spray

Mineral oils: Mineral oils are typically transparent, colorless oils obtained from refining crude oil (z.e., a mineral source) and primarily consists of higher alkanes. Mineral oils increase spray droplet size and alter the dynamic surface tension of the spray solution such that it prevents breaking of water droplets during spray application.

This list is not exhaustive, and the selection of a suitable retention agent or combination thereof would depend on the specific requirements of the formulation, including compatibility with other components, desired release profile, regulatory compliance, and environmental impact considerations.

The inclusion of spreading agents can significantly enhance the distribution and coverage of the formulation on target surfaces, such as plant leaves and stems. The spreading activity is particularly important in instances where certain applications of the compound of Formula One requiring low application volumes. Suitable spreading agents are selected from the group consisting of:

Silicone-based surfactants: These are polydimethyl siloxane-poly oxyalkylene block copolymers that reduce surface tension significantly, thus improving spreading on hydrophobic leaf surfaces.

Alkylpolyglucosides (APGs): Biodegradable and non-toxic surfactants derived from sugars and fatty alcohols. They are known for their good wetting and spreading properties. Ethoxylated alcohols: Nonionic surfactants that consist of a hydrophobic alkyl chain and a hydrophilic ethylene oxide chain, which can enhance spreading by lowering the surface tension of the formulation.

Sodium lauryl sulfate (SLS): An anionic surfactant and detergent commonly used to increase wetting and spreading properties due to its ability to disrupt intermolecular interactions. Sorbitan esters: Nonionic surfactants derived from sorbitol and fatty acids, known as Spans, which can act as spreading agents by reducing surface tension.

Lecithins: Naturally occurring phospholipids that can act as spreading agents due to their amphiphilic character, improving the distribution of agrochemical formulations on plant surfaces.

Fluorinated surfactants: Surfactants that contain fluorine atoms in their structure and are known for their ability to lower surface tension dramatically, leading to enhanced spreading and coverage.

Propylene glycol: A synthetic organic compound that can act as a humectant and spreading agent in agrochemical formulations, aiding in the uniform distribution of the product.

Glycerol esters: Fatty acid esters of glycerol that can serve as spreading agents by reducing surface tension and improving the formulation’s wetting properties on plant surfaces.

Polysorbates (Tweens): Ethoxylated sorbitan ester surfactants that are effective in reducing surface tension, thus enhancing the spreading as well as retention of agrochemical formulations.

In certain instances, the spreading agents are polysorbates (Tweens). In other instances, the retention agents are polysorbates (Tweens). There are several Tween variants. Each Tween variant has specific properties and applications depending on the fatty acid chain length and the degree of ethoxylation, affecting their hydrophilic-lipophilic balance (HLB) and thus their solubility and emulsifying capabilities. The selection of a particular Tween for a formulation is guided by the desired properties in the final product, such as the type of emulsion (oil-in-water or water-in-oil), solvent solubility, viscosity, and stability requirements. Tweens that can be used in the formulations disclosed herein are: Tween 20 (Polysorbate 20): This is a laurate ester of sorbitan and polyethylene oxide. It is commonly used in the food industry as an emulsifier (E432), in pharmaceuticals to improve the solubility of APIs (Active Pharmaceutical Ingredients), and in cosmetics for its emulsifying properties in lotions and creams.

Tween 40 (Polysorbate 40): Made from the esterification of sorbitan with polyethoxylated palm oil, Tween 40 is often used in food products as an emulsifier, as well as in pharmaceutical formulations to enhance the solubility and stability of drugs.

Tween 60 (Polysorbate 60): Derived from the stearate ester of sorbitan and ethylene oxide, this surfactant is frequently employed in the bakery industry to improve the volume and texture of baked goods, as well as in cosmetics for its ability to blend ingredients together smoothly.

Tween 80 (Polysorbate 80): A oleate ester of sorbitan and polyethylene oxide, Tween 80 is widely used in the food industry as an emulsifier, in pharmaceuticals to enhance the bioavailability of poorly soluble drugs, and in cosmetics for its emollient and surfactant properties. Accordingly, in one aspect, the agrochemical formulations disclosed herein comprise A) the compound of Formula One, B) one or more of agrochemically acceptable excipients as disclosed herein and C) an adjuvant which is a non-ionic surfactant based on sorbitan ester, or mixtures thereof. For example, the agrochemical formulations disclosed herein may comprise a mixture of adjuvants such as a retention agent and a spreading agent.

Alcohol alkoxylates can be used as retention agents. One specific example is Synergen W 06. Another specific example is Berol 840.

Ethoxylated fatty alcohols can also be used as suitable retention agents. For example, Genapol C-200 (Clariant Corporation), is a fatty alcohol ethoxylate derived from the chemical reaction of a fatty alcohol with ethylene oxide, resulting in a molecule that has both hydrophilic (water-loving) and lipophilic (oil-loving) properties. This dual affinity makes Genapol C-200 and other ethoxylated fatty alcohols effective as surfactants, which can lower the surface tension between two substances, such as oil and water, facilitating their mixture or emulsification. Ethoxylated alcohols can also be used as retention agents. Ethoxylated alcohols, are characterized by their ability to reduce surface tension between two liquids or a liquid and a solid, making them effective as detergents, wetting agents, emulsifiers, and dispersants. These properties are highly valuable in a variety of applications across multiple industries, including cleaning products, personal care formulations, textiles, and agrochemicals. The balance between the hydrophobic (water-repelling) and hydrophilic (water-attracting) segments of such molecules can be adjusted by changing the length of the alkyl chain or the number of ethylene oxide units, allowing for customization of the surfactant’s properties for specific applications. One example of an ethoxylated alcohol is Synperonic 91/6 (Croda Inc.). The nomenclature “91/6” typically refers to the specific structure of the surfactant, where “91” can denote the alkyl chain length or type of the alcohol precursor, and “6” indicates the average number of ethylene oxide units added through ethoxylation. In the case of Synperonic 91/6, it suggests a specific type of fatty alcohol that has been ethoxylated with an average of 6 moles of ethylene oxide. An additional example is Genapol X 060 (Clariant Corporation), which is a fatty alcohol that has an average of 6 moles of ethylene oxide. Other examples are Lutensol TDA 9 (BASF Corporation) and Genapol X 090 (Clariant Corporation), which are fatty alcohols that have been ethoxylated with an average of 9 moles of ethylene oxide. Other examples of fatty alcohols include Agnique TDA 9 (BASF Corporation), Bio-soft N1 -9 (Stepan Company), Brimopol S-1306 (Polaquimia, S.A. de C.V.), Lutensol TDA 8 (BASF Corporation), Makon DA-6 (Stepan Company), Makon DA-9 (Stepan Company), Surfonic TDA-6 (Indorama Ventures Oxides LLC), and Synperonic 13/9 (Croda Inc.)

Silicone-based surfactants, such as Silwet HS-312 (Momentive Performance Materials), Silwet 408 (Momentive Performance Materials), Break-thru S 200 (Evonik), and Break-thru OE 446 (Evonik) can also be used as spreading agents. Specifically, many Silwet products are a type of organosilicone surfactant, which combines the unique properties of silicone with organic modifications that grant them surfactant capabilities. These modifications often involve the incorporation of polyether chains into the silicone backbone, creating molecules with both hydrophobic (silicone) and hydrophilic (polyether) regions. This dual nature allows Silwet surfactants to achieve ultra-low surface tensions when dissolved in water, making them far more efficient at spreading and wetting than traditional hydrocarbon-based surfactants. The unique structure of Silwet surfactants enables them to spread over and penetrate surfaces quickly and efficiently, which is particularly advantageous in applications requiring superior wetting and spreading on hydrophobic surfaces, such as plant leaves in agricultural formulations.

In one aspect, organomodified polyether trisiloxanes can be used as spreading agents. Examples of this chemistry are Break-thru S 301(Evonik), Break-thru S 279 (Evonik), Break- thru S 240 (Evonik), Break-thru SD 260 (Evonik), and Break-thru S 233 (Evonik). Other similar spreading agents of the same chemical class can be used in the formulations disclosed herein, such as Sylgard 309 Silicone surfactant (DOW) and Silwet L-77 (Momentive Performance Materials). Accordingly, in one aspect, the agrochemical formulations disclosed herein comprise A) the compound of Formula One, B) one or more of agrochemically-acceptable excipients as disclosed herein and C) an adjuvant which is a non-ionic surfactant based on organomodified polyether trisiloxane. In another aspect, the agrochemical formulations disclosed herein comprise A) the compound of Formula One, B) one or more of agrochemically-acceptable excipients as disclosed herein and C) one or more an adjuvant which is a non-ionic surfactant based on sorbitan ester and / or a non-ionic surfactant based on organomodified polyether trisiloxane.

In one aspect, disclosed herein is an agrochemical formulation comprising the compound of Formula one, and one or more agrochemically-acceptable excipients. Such formulation can be an aqueous-based formulation or an organic-solvent-based formulation suitable for agrochemical applications such as foliar, soil, in-furrow or seed treatment applications.

“Agrochemically-acceptable excipients” in this context refer to inert substances approved for use in agrochemical formulations that ensure the long-term stability, ease of application, and safety of active ingredients without inducing chemical changes or undesired biological effects and do not possess significant pesticidal properties themselves. These excipients play a crucial role in the formulation of various agrochemical products, including pesticides, herbicides, fungicides, and fertilizers, among others. Their primary function is not to exert direct agrochemical activity but to ensure stability of and allow for application of active ingredients.

In contrast, “Agrochemically-acceptable adjuvants” or “adjuvants” as used herein are specialized substances or mixtures that are added to agrochemical formulations or tank mixes without possessing significant pesticidal properties themselves. In particular instances, these adjuvants improve the delivery of agrochemical actives during or after application, including herbicides, pesticides, fungicides, and fertilizers, facilitating their biological effectiveness. The functions of adjuvants can include improving the solubility and stability of active ingredients, modifying spray droplet characteristics, enhancing foliar absorption and adherence, and reducing environmental impact by minimizing off-target drift and volatilization. Agrochemically- acceptable adjuvants are distinguished by intended use, their compatibility with various agrochemical formulations, and their compliance with environmental and regulatory standards.

In some instances, the one or more agrochemically-acceptable excipients are selected from the group consisting of thickening agents, antifreeze agents, surfactants (i.e. emulsifiers, wetting agents, dispersants), antimicrobials, antifoams, pH modifiers, film formers, colorants, flow aids, and diluents. In some specific instances, the agrochemical formulations disclosed herein do not comprise a further adjuvant. In some other instances, the formulations disclosed herein comprise both an agrochemically-acceptable excipients and an agrochemically-acceptable adjuvant. In additional instances, the formulations disclosed herein comprise both agrochemically-acceptable excipients and a combination of agrochemically-acceptable adjuvants. In some particular instances, agrochemical formulations comprising compound of Formula One having an active concentration (loading) of between 0.5%- 70% w/w show good biological efficacy while possessing beneficial processing properties such as storage stability, even in the absence of adjuvants.

As used herein, “biological efficacy” refers to the effectiveness of the formulations comprising compound of Formula One in killing or controlling or combating target insect populations. It measures the compound of Formula One’s ability to achieve its intended effect, such as reducing, eliminating or controlling the population of harmful insects, and preventing damage to crops.

In formulating suspension concentrates (SC) and flowable concentrate for seed treatment (FS) for agrochemical applications, using the right thickening agent is crucial for ensuring formulation stability and ease of application. In heterogeneous formulations, such as SC and FS, it is preferred to incorporate a thickening agent that imparts the composition with structural viscosity. The thickening agent, as such, helps in maintaining the suspended particles evenly distributed throughout the liquid phase and can also aid in reducing sedimentation and improving spray characteristics. In some aspects, the thickening agents are selected from gum arabic, guar gum, xanthan gum, pectin, cellulose derivatives, clay minerals, white carbon, talc, bentonite, polyacrylic acid and their salts, alginates, guar gum, polyvinylpyrrolidone (PVP), silica, and acacia gum. In some aspects, the specific examples are Rhodopol 23 (Solvay), Rhodopol 50 MC (Solvay), Grindsted Xanthan 80 (Danisco), Kelzan (CP Kelco), Kelzan AR (CP Kelco), Kelzan D (CP Kelco), Kelzan S (CP Kelco), Veegum R (Vanderbilt Minerals, LLC), Xanthan Gum TGRD (Jungbunzlauer) Methocel F4M (International Flavors & Fragrances), and Lattice NTC 65 (International Flavors & Fragrances).

In the field of agrochemical formulations, particularly suspension concentrate (SC) and flowable concentrate for seed treatment (FS), maintaining fluidity and preventing crystal growth, agglomeration or solidification at low temperatures is critical for storage stability, ease of handling, and application efficiency. Antifreeze agents play a pivotal role in enhancing these characteristics by lowering the freezing point of the liquid phase, thereby ensuring that the agrochemical formulation remains fluid under cold conditions. The antifreeze components that can be incorporated into suspension concentrate formulations disclosed herein improve low- temperature stability without compromising the bioavailability of the active ingredients. Antifreeze agents, as described herein, refer to additives capable of lowering the freezing point of water or aqueous solutions in suspension concentrate agrochemical formulations. These agents prevent the formation of ice crystals which can lead to physical instability, including sedimentation and agglomeration of suspended particles. In a heterogenous formulation, if a liquid antifreeze agent is used the solubility of the active ingredient must be low in the antifreeze to prevent physical stability challenges, such as crystal growth of the suspended active ingredient. The effectiveness of an antifreeze agent is measured by its ability to maintain the formulation in a fluid state at temperatures significantly below the freezing point of water. The antifreeze agents that can be used in the formulations disclosed herein can be selected from the group consisting of alcohols (e.g., ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol), glycerols (e.g., glycerine), sugars (e.g., sorbitol, mannitol), salts (e.g., calcium chloride, potassium formate), and ureas (e.g., ethylene urea). In some aspects, specific examples include propylene glycol and glycerin.

Diluents, as defined herein, are inert substances used in suspension concentrate and flowable concentrates for seed treatment agrochemical formulations to adjust the concentration of active ingredients, facilitating their dispersion and stable suspension within the carrier medium. The role of diluents is crucial for achieving the desired viscosity, ensuring ease of application, and as volume adjustment. The diluents suitable for the formulations disclosed herein are selected from the group consisting of water, alcohols, esters, and glycols. Tn specific instances, water is used as a diluent.

In one aspect, disclosed herein is an agrochemical formulation comprising a compound of Formula One and one or more agrochemically-acceptable excipients selected from the group consisting of thickening agents, antifreeze agents, surfactants (z.e., dispersants or wetting agents), antimicrobials, antifoams, pH modifiers, adjuvant, film formers, flow aids, diluents and colorants, wherein the concentration of the compound of Formula One is l%w/w to 70%w/w. In some specific instances, the concentration of the compound of Formula One is l%w/w to 65%w/w. In some other instances, the concentration of the compound of Formula One is l%w/w to 55%w/w. In some other instances, the concentration of the compound of Formula One is l%w/w to 45%w/w. In some specific instances, the concentration of the compound of Formula One is l%w/w to 35%w/w. In some other instances, the concentration of the compound of Formula One is l%w/w to 35%w/w. In some instances, the concentration of the compound of Formula One is l%w/w to 25%w/w. In some other instances, the concentration of compound of Formula One is l%w/w to 15%w/w. In other specific instances, the concentration of the compound of Formulation One is 1% w/w to 10%w/w. In some other specific instances, the concentration of compound of Formulation One is 1% to 5%w/w

In one aspect, disclosed herein is an agrochemical formulation comprising a compound of Formula One and one or more agrochemically-acceptable ingredients selected from the group consisting of thickening agents, antifreeze agents, diluents, surfactants (z.e., dispersants or wetting agents), antimicrobials, antifoams, pH modifiers, adjuvants, film formers, flow aids, and colorants wherein the concentration of the compound of Formula One is selected from any of the following values: l%w/w, 3%w/w, 5%w/w, 7%w/w, 9%w/w, 10%w/w, 15%w/w, 20%w/w, 23%w/w, 25%w/w, 30%w/w, 35%w/w, 40%w/w, 45%w.w, 50%w/w, 55%w/w, 60%w/w/, 65%w/w, and 70%w/w.

In another aspect, disclosed herein is an agrochemical formulation comprising a compound of Formula One and one or more agrochemically-acceptable ingredients selected from the group consisting of thickening agents, antifreeze agents, diluents, surfactants (z.e., dispersants or wetting agents), antimicrobials, antifoams, pH modifiers, adjuvants, film formers, flow aids, and colorants wherein the particle size of the compound of Formula One is less than or equal to 8pm. In certain instances, 99% by volume of the particles of the compound of Formula One is less than or equal to 8 pm (Dv99). In some specific instances, 90% by volume of the particles of the compound of Formula One is less than or equal to 8pm (Dv90). In some other instances, more than 50% of the particles of the compound of Formula One is less than or equal to 8pm

(Dv50).

In another aspect, disclosed herein is an agrochemical formulation comprising a compound of Formula One and one or more agrochemically-acceptable excipients selected from the group consisting of thickening agents, antifreeze agents, diluents, surfactants (i.e., dispersants or wetting agents), antimicrobials, antifoams, pH modifiers, film formers, flow aids, and colorants wherein the particle size of the compound of Formula One is less than or equal to 3 pm. In certain instances, 99% of the particles of compound of Formula One is less than or equal to 3 pm (Dv99). In some specific instances, 90% of the particles of the compound of Formula One is less than or equal to 3 pm (Dv90). In some other instances, more than 50% of the particles of the compound of Formula One is less than or equal to 3pm (Dv50).

In another aspect, disclosed herein is an agrochemical formulation comprising a compound of Formula One and one or more agrochemically-acceptable excipients selected from the group consisting of thickening agents, antifreeze agents, diluents surfactants (i.e., dispersants or wetting agents), antimicrobials, antifoams, pH modifiers, , film formers, flow aids, and colorants wherein the particle size of the compound of Formula One is less than or equal to 1pm. In certain instances, 99% of the particles of the compound of Formula One is less than or equal to 1 pm (Dv99). In some specific instances, 90% of the particles of the compound of Formula

One is less than or equal to 1pm (Dv90). In some other instances, more than 50% of the particles of the compound of Formula One is less than or equal to 1pm (Dv50 Generally, in these formulations, the particle size of the compound of Formula One is between less than or equal to 1pm and greater than or equal to 0.5pm (Dv90). In these instances, such formulations further comprise an adjuvant (in addition to agrochemically-acceptable excipients disclosed herein) selected from the group consisting of retention agent, spreading agent or an agent that acts as both a retention agent and a spreading agent. The retention agent and/or spreading agent are selected from the adjuvants disclosed throughout this disclosure. The specific examples include non-ionic surfactants such as polysorbates, ethoxylated fatty alcohols, ethoxylated alcohols, silicone-based surfactants, organo-modified polyether siloxanes. In another aspect, disclosed herein is an agrochemical formulation comprising a compound of Formula One and one or more agrochemically-acceptable excipients selected from the group consisting of thickening agents, antifreeze agents, diluents, surfactants (/.e., dispersants or wetting agents) antimicrobials, antifoams, pH modifiers, film formers, flow aids, and colorants wherein the particle size of the compound of Formula One is less than or equal to 3 pm (Dv90). In these instances, such formulations further comprise an adjuvant (in addition to agrochemically-acceptable excipients disclosed herein) selected from the group consisting of retention agent, spreading agent or an agent that acts as both a retention agent and a spreading agent. The retention agent and/or spreading agent are selected from the adjuvants disclosed throughout this disclosure. The specific examples include non-ionic surfactants such as polysorbates, ethoxylated fatty alcohols, ethoxylated alcohols, silicone-based surfactants, organo-modified polyether siloxanes.

In another aspect, disclosed herein is an agrochemical formulation comprising a compound of Formula One and one or more agrochemically-acceptable excipients selected from the group consisting of thickening agents, antifreeze agents, diluents, surfactants (i.e., dispersants or wetting agents), antimicrobials, antifoams, pH modifiers, film formers, flow aids, and colorants wherein the particle size of the compound of Formula One is between 1 pm to 0.5 pm (Dv90). In these instances, such formulations further comprise an adjuvant (in addition to agrochemically-acceptable excipients disclosed herein) selected from the group consisting of retention agent, spreading agent and an agent that acts as both a retention agent and a spreading agent. The retention agent and/or spreading agent are selected from the adjuvants disclosed throughout this disclosure. The specific examples include non-ionic surfactants such as polysorbates, ethoxylated fatty alcohols, ethoxylated alcohols, silicone-based surfactants, organo-modified polyether siloxanes.

In another aspect, disclosed herein is an agrochemical formulation comprising a compound of Formula One and one or more agrochemically-acceptable excipients selected from the group consisting of thickening agents, antifreeze agents, diluents , surfactants i.e., dispersants or wetting agents) antimicrobials, antifoams, pH modifiers, film formers, flow aids, and colorants wherein the particle size of the compound of Formula One is less than or equal to 5pm (Dv90). In these instances, such formulations further comprise an adjuvant (in addition to agrochemically-acceptable excipients disclosed herein) selected from the group consisting of a retention agent, a spreading agent and an agent that can act as both a retention agent and a spreading agent. The spreading agent and/or retention agent is selected from the adjuvants disclosed throughout this disclosure. The specific examples include non-ionic surfactants such as polysorbates, ethoxylated fatty alcohols, ethoxylated alcohols, silicone-based surfactants, organo-modified polyether siloxanes.

In another aspect, disclosed herein is an agrochemical formulation comprising a compound of Formula One and one or more agrochemically-acceptable excipients selected from the group consisting of thickening agents, antifreeze, diluent, surfactants (z.c., dispersants or wetting agents), antimicrobial, antifoam, pH modifier, film formers, flow aids, and colorant wherein the particle size of the compound of Formula One is less than or equal to 8pm (Dv90). In these instances, such formulations further comprise an adjuvant (in addition to agrochemically-acceptable excipients disclosed herein) selected from the group consisting of retention agent, spreading agent or an agent that acts as both a retention agent and a spreading agent. The retention agent and/or spreading agent are selected from the adjuvants disclosed throughout this disclosure. The specific examples include non-ionic surfactants such as polysorbates, ethoxylated fatty alcohols, ethoxylated alcohols, silicone-based surfactants, organo-modified polyether siloxanes.

In specific embodiments of the formulations disclosed herein, where adjuvants are present, the adjuvant concentration needs to be carefully selected. In some aspects, the adjuvant concentration is below 40%w/w. In some aspects, the adjuvant concentration is below 35%w/w. In some other aspects, the adjuvant concentration is below 30%w/w. In some aspects, the ratio between the adjuvant concentration and the concentration of the compound of Formula One is 1 : 1, 2:1, 2.5: 1, 3: 1, 4: 1, and 6: 1. In particular examples, the ratio between the adjuvant concentration and the concentration of the compound of Formula One is 2: 1. For example, in one specific embodiment, a formulation with particle size < 1 m disclosed herein comprises 29%w/w adjuvant concentration and 7%w/w to 10%w/w concentration of the compound of Formula One. In some instances, the agrochemical formulations disclosed herein comprise 24%w/w adjuvant concentration and 7%w/w to 36%w/w concentration of the compound of Formula One. In some additional instances, the agrochemical formulations disclosed herein comprise 19%w/w adjuvant concentration and 7%w/w to 36%w/w concentration of the compound of Formula One. In particular examples, the presence of an adjuvant is found to impart certain unexpected and surprising properties. For example, in specific instances, the agrochemical formulations that comprise particle sizes less than or equal to 3 pm or formulations that comprise particle sizes less than or equal to 1 pm exhibited improved delivery, improved retention, improved spreading or combination of one or more properties thereof in comparison to formulations that comprise particle sizes larger than 3 pm.

In some specific embodiments, the formulations disclosed herein comprise two or more adjuvants. For example, in some embodiments, the formulations disclosed herein comprise a retention agent and a spreading agent. In some embodiments, the formulations disclosed herein comprise two retention agents. In such instances, where the formulations comprise two or more adjuvants, the ratio between the adjuvants range from 1 : 10 to 10: 1; 1 :5 to 5: 1; 1 :4 to 4: 1; 1 :3 to 3: 1; 1:2 to 2: 1; 1 : 1. In some specific instances, the ratio is from 1 : 1. In some other instances, the ratio is 2:1. In some instances, the ratio is 1:2. In some other instances, the ratio is 2.1 to 1. In other instances, the ratio is 2.3 to 1. In some other instances, the ratio is 2.5 to 1.

In some specific instances, the concentration of compound of Formula one having a particle size of less than or equal to 8pm (Dv90) is between 1%- 40%w/w.

In some specific instances, the loading concentration of formulations comprising a compound of Formula One having particle size of less than or equal to 3 pm (Dv90) is between 1% - 35%w/w.

In some specific instances, the loading concentration of formulations comprising a compound of Formula One having particle size of less than or equal to 1 pm (Dv90) is between 1% - 25%w/w.

In some instances, the concentration of compound of Formula one in the formulations disclosed herein depends on the adjuvant loading; for example, in some aspects when the adjuvant loading is 24%w/w, where the particle size is 3 pm (Dv90), the loading concentration of compound of Formula one is 4%-20% w/w. In some aspects when the adjuvant loading is 24%w/w, where the particle size is 1pm (Dv90), the loading concentration is 7%-l 5% w/w.

In some instances, the presence of adjuvants may also contribute to other desirable properties. For example, certain adjuvants can improve rainfastness (when it has dried on the plant surfaces or was absorbed into the plant tissue and remains effective even after rain or irrigation) of the disclosed formulations. The agrochemical formulations disclosed herein comprise crystalline forms of the compound of Formula One. Specifically, the suspension concentrate formulations and flowable concentrate formulations for seed treatment disclosed herein comprise the crystalline forms of Formula One. In particular, any of the crystalline forms illustrated below can be used. In some aspects, the agrochemical formulations disclosed herein comprise certain specific crystalline forms of the compound of Formula One. As used herein, the crystalline forms are stable solid forms of the compound of Formula One, and refers to a solid-state form of a compound of Formula One characterized by a defined and repeating three-dimensional arrangement of its constituent molecules, atoms, or ions, as determined by techniques such as X- ray powder diffraction (XRPD), single-crystal X-ray diffraction, and/or other crystallographic methods. The crystalline forms may be further characterized by distinct physicochemical properties.

In some aspects, the agrochemical formulations disclosed herein comprise the crystalline form A of the compound of Formula One comprising at least three of the following reflexes in any combination as 20 ± 0.20 in an X-ray powder diffractogram (PXRD) recorded using Cu-Ka radiation at 25 °C:

In one aspect, the suspension concentrate formulations disclosed herein comprise 0.1- 2%w/w of a wetting agent or combination of wetting agents, 2-10%w/w of a dispersing agent or combination of dispersing agents, 0.05% -3%w/w thickening agent or combination of two or more thickening agents, and 0-20%w/w of antifreeze agent or combination of antifreeze agents.

In some aspects, the suspension concentrate formulations disclosed herein comprise one or more of wetting agents, dispersing agents, antifoam agents, and antifreeze agents. In addition, the formulations also comprise typical suspension concentrate formulation excipients such as thickeners, viscosity modifiers, and biocides. Generally, these formulation ingredients are present in the range of 3-20%w/w. In some instances, these formulation ingredients are present between 3-15 %w/w.

The wetting agent are surfactants or surface active agents. These are selected from the group consisting of :

Nonionic Surfactants: Nonionic surfactants, generally, may include alcohol ethoxylates, fatty acid esters, water-soluble adducts of polyethylene oxide with polypropylene glycol, di ethylenediaminopolypropylene glycol and alkylpolypropylene glycol. Examples of nonionic surfactants include polyoxyethylene sorbitan trioleate, polyoxyethylene-polyoxypropylene block copolymers, polygycol ether derivatives of aliphatic or cycloaliphatic alcohols or saturated or unsaturated fatty acids, polyethoxylated castor oil, polyadducts of polypropylene and polyethylene oxide, tributyl phenol polyethoxylate, polyethylene glycol, acrylic graft copolymers, and polyoyalkylene copolymers. Alkylphenol ethoxylates (APEs), alcohol ethoxylates, ethylene oxi de-propylene oxide (EO/PO) copolymers, alkyl polyglucosides (APGs); Anionic Surfactants: Alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts of higher fatty acids. Examples of the preceding list include sodium salts of oleic or stearic acid. Additional anionic chemistries include alkyl aryl sulfonates, dialkyl sulfonates, dialkyl succinates, aryl sulfonates and condensation products thereof, alkyl sulfuric acid esters, alkyl phosphoric acid esters, alkylaryl sulfuric acid esters, alkylaryl phosphoric acid esters, polycarboxylates, polyoxyalkylene aryl ether sulfates, polyoxyalkylene aryl ether phosphates, polyoxyethylene ether phosphate, lignin sulfonates, ethoxylated tri styrylphenol phosphates. An example is an alkylnaphthalenesulfonate formaldhye condensate, alkylbenzene sulfonates (ABS), linear alkylbenzene sulfonates (LAS), alkyl sulfates (AS), alkyl ether sulfates (AES);

Cationic Surfactants: In general, cationic surfactants are comprised of quaternary ammonium salts carry N-substituents. More specifically these include tetralkyl ammonium salts, alkylamines, and alkyl pyridinium salts. Preferably the salts are in the forms of halides or sulfates (methyl or ethyl). An example can include stearyl trimethyl ammonium chloride;

Amphoteric Surfactants: Alkyl betaines, alkyl amine oxides, alkyl imidazolinium betaines, amino acids, and lecithin;

Silicone Surfactants: polyalkyleneoxide modified heptamethyltri siloxane, and organomodified trisiloxanes;

The dispersing agents are selected from the group consisting of polycarboxylates, naphthalene sulfonate formaldehyde condensates, lignosulfonates, polyvinylpyrrolidone, polysaccharides, polyoxyethylene sorbitan esters (Tweens), polyethylene glycols, block copolymers (e.g., polyethylene oxide)-poly(propylene oxide), ethylene oxide-propylene oxide block copolymers (EO/ PO block copolymers) including both EO-PO-EO and PO-EO-PO block copolymers), alkylphenol ethoxylates (APEs);

Biocides / preservatives include parabens, sorbic acid salts, 5-chloro-2-methyl-4- isothiazolin-3-one, 2-Methyl-l,2-thiazol-3(2H)-one, 2-bromo-2 -propan- 1,3-diol, 1,2- benzisothiazolin-3-one, sodium benzoate, sodium p-hydroxy benzoate and potassium sorbate, and any substance known for this application may be used singly or two or more thereof may be used in combination.

The suspension concentrate formulations for foliar application disclosed herein may also include one or more of adjuvants. In some instances, adjuvants are present up to 5% - 30% w/w. In certain aspects, the suspension concentrate formulations for foliar application disclosed herein may also include one or more pH modifiers. In some instances, pH modifiers are present up to 0.01% - l%w/w.

In some instances, the disclosure provided herein can be used to obtain agrochemical formulations comprising amorphous form of the compound of Formula One, even though the crystalline forms are preferred. For example, in some specific instances, amorphous forms may offer certain advantages over the crystalline forms; for example, amorphous form of the compound of Formula One generally may have better solubility, and a faster dissolution rate in liquid formulations comprised of solvent in which the compound of formula one is present in a dissolved form in the formulation concentrate (e.g., emulsifiable concentrate). In another example, certain stabilizers, humectants, optimized surfactants and wetting agents and viscosity modifiers, with the aid of the disclosure herein, one may generate a suspension concentrate formulation comprising the amorphous form of the compound of Formula One.

In some aspects, the agrochemical formulations disclosed herein require an optimized pH balance. In certain aspects, the pH defined here refers to an undiluted solution of the agrochemical formulation (i.e., neat formulation). In certain other aspects, the pH defined here refers to the diluted solution of the agrochemical formulation (1% dilution of formulation in water). The pH stability across neat and diluted states provides improved stability of the formulation. Unless otherwise specified, the pH is measured at 25°C. In some aspects, both the neat or diluted pH of the agrochemical formulations disclosed herein is less than 9.0. In some aspects, both the neat or diluted pH of the agrochemical formulations disclosed herein is between pH 3.0 - pH 9.0. In some other aspects, both the neat or diluted pH of the agrochemical formulations disclosed herein is between pH 4.0 - pH 9.0. In some specific instances, the pH of the agrochemical formulations disclosed herein, specifically, any solvent-based formulations, cannot exceed pH 9.0. Accordingly, in one aspect, disclosed herein is an agrochemical formulation comprising the compound of Formula One, at least one or more of agrochemically acceptable excipients, optionally, one or more adjuvants, wherein both the neat or diluted pH of the formulation is within the range of 3.0-9.0. In other specific aspects, with one or more adjuvants, wherein both the neat or diluted pH of the formulation is within a range of 3.0 - 6.5. In additional specific aspects, with one or more adjuvants, wherein the neat pH is within a range of 4 - 6.5. And in other additional aspects, with one or more adjuvants, wherein the neat pH is within a range of 5 - 6.5.

The optimum pH balance can be achieved using pH modifiers. Such pH modifiers can be selected from the following: acidic substances such as sulfuric acid, citric acid, lactic acid, malonic acid, adipic acid, maleic acid, phosphoric acid, oleic acid, salicylic acid, acetic acid, fumaric acid, ammonium sulfate and potassium dihydrogen phosphate; basic substances such as sodium hydroxide, potassium hydroxide, triethanol amine, sodium carbonate and calcium carbonate; and mixtures of a weak acid a conjugate base thereof as well as mixtures of a weak base and a conjugate acid thereof, which exhibit a buffering capability in aqueous solutions. Examples include trisodium citrate dihydrate, sodium sulfate, and trisodium phosphate. Inclusion may also be salts that modify pH, such as ethylenediaminetetraacetic acid. Any substance known for pH modification or buffering in this application may be used singly, or two or more thereof may be used in combination as desired. Seed Treatment Formulations

One aspect of the formulations disclosed herein is a formulation comprising the compound of Formula One suitable for seed treatment application. In some aspects, the seed treatment formulation is a flowable concentrate for seed treatment (FS) formulation.

The seed treatment formulations disclosed herein comprise the compound of Formula One in up to 70% w/w. In certain instances, the seed treatment formulations disclosed herein comprise the compound of Formula One in up to 60% w/w. In some instances, the seed treatment formulations disclosed herein comprise the compound of Formula One in up to 50% w/w. In some other instances, the seed treatment formulations disclosed herein comprise the compound of Formula One in up to 40% w/w. In some instances, the seed treatment formulations disclosed herein comprise the compound of Formula One in up to 30% w/w. In some instances, the seed treatment formulations disclosed herein comprise the compound of Formula One in up to 20% w/w. In some instances, the seed treatment formulations disclosed herein comprise the compound of Formula One in up to 10% w/w. In some instances of seed treatment formulations, specifically with respect to certain per-mix formulation, may comprise the compound of Formula One is up to 5% w/w. In certain instances, the loading concentration of the compound of Formula One is less than 5% w/w. In certain other instances, the loading concentration of the compound of Formula One is less than or equal to 2% w/w. In certain instances, the loading concentration of the compound of Formula One may depend on the amount/activity of other actives. In these instances, the compound of Formula One can be present in less than or equal to 1% w/w; In some specific instances, the compound of Formula One is present is less than or equal to 0.5-0.8% w/w.

The seed treatment formulations disclosed herein may comprise other active ingredients other than the compound of Formula One. These active ingredients are selected from the group consisting of fungicides, nematicides, insecticides, biological agents, macronutrients, micronutrients, and plant growth regulators. In some instances, the seed treatment formulations disclosed herein may comprise one or more fungicides. In some other instances, the seed treatment formulations disclosed herein may comprise one or more insecticides. In some instances, the seed treatment formulations disclosed herein may comprise one or more nematicides. In some instances, the seed treatment formulations disclosed herein may comprise one or more of fungicide, insecticide, nematicide and a biological agent.

In some aspects, the active ingredients mixtures are selected from the group consisting of following mixture combinations comprising the actives shown therein. The compound of Formula One is denoted as Fl.

Aspect A: Agrochemical composition selected from the group consisting of

1. Fl, imidacloprid, metalaxyl, picoxystrobin, ethaboxam, ipconazole, oxathiapiprolin

2. Fl, metalaxyl, picoxystrobin, ethaboxam, ipconazole, oxathiapiprolin

3. Fl, mefenoxam, picoxystrobin, ethaboxam, ipconazole, oxathiapiprolin

4. Fl, pydiflumetofen, oxathiapiprolin

5. Fl, imidacloprid, isocycloseram, picoxystrobin, ethaboxam, ipconazole, oxathiapiprolin

6. Fl, isocycloseram, picoxystrobin, ethaboxam, ipconazole, oxathiapiprolin

7. Fl, cyclobutrifluram, picoxystrobin, ethaboxam, ipconazole, oxathiapiprolin

8. Fl, fludioxonil, mefenoxam, thiabendazole, azoxy strobin

9. Fl, inpyrfluxam, ethaboxam, metalaxyl

10. Fl, prothioconazole, fluoxastrobin, metalaxyl

11. Fl, fludioxonil, thiabendazole, azoxystrobin, mefenoxam, sedaxane

12. Fl, penflufen, prothioconazole, metalaxyl

13. Fl, difenaconazole, inpyrfluxam, ipconazole, mefenoxam

14. Fl, thiamethoxam 15. Fl, metalaxyl

16. Fl, mefenoxam

17. Fl, azoxystrobin

18. Fl, clothianidin

19. Fl, fluxapyroxad

20. Fl, prothioconazole

21. Fl, fipronil

22. Fl, difenoconazole

23. Fl, fluopyram

Following aspects are also within the formulations disclosed herein: Aspect B

Another aspect is a agrochemical composition comprising Fl and a mixing partner, wherein the mixing partner is selected from the group consisting of abamectin, acetamiprid, benzpyrimoxan, bifenthrin, chlorantraniliprole, chlorfenapyr, cyantraniliprole, cyclobutrifluram, dimepropyridaz, fipronil, flonicamid, fluoxapiprolin, flupyradifurone, flupyrimin, fluxametamide, imidacloprid, indoxacarb, isocy closeram, /czm/>c7cz-cyhalothrin, methoxyfenozide, pymetrozine, pyriproxyfen, spidoxamat, spinetoram, spinosad, spiropidion, spirotetramat, sulfoxaflor, thiamethoxam, and triflumezopyrim.

Aspect C

Another aspect is a agrochemical composition comprising Fl and a mixing partner wherein the mixing partner is selected from the group consisting of azoxystrobin, copper hydroxide, difenoconazole, ethaboxam, fludioxonil, fluopyram, fluoxastrobin, fluxapyroxad, inpyrfluxam, ipconazole, isoflucypram, mefenoxam, mefentrifluconazole, metalaxyl, myclobutanil, oxathiapiprolin, picoxystrobin, propiconazole, prothiaconazole, pydiflumetofen, pyroclostrobin, sedaxane, tebuconazole, thiabendazole, thiram, titriconazole, trifloxystrobin, abamectin, acetamiprid, afidopyropen, AI-1, AI-2, benpyrimoxan, bifenthrin, broflanilide, chlorantraniliprole, chlorfenapyr, clothianidin, cyantraniliprole, deltamethrin, dinotefuran, fipronil, flonicamid, fluazaindolizine, fluensulfone, flupyradifurone, flupyrimin, fluxametamide, heat-killed Burkholderia spp. Strain A 396, imidacloprid, indoxacarb, lambda cyhalothrin, methoxyfenozide, oxamyl, pyriproxyfen, spinosad, spinetoram, spiromesifen, spirotetramet, sulfoxaflor, tetraniliprole, thiamethoxam, , and triflumezopyrim. Aspect D

Another aspect is a agrochemical composition comprising Fl and a mixing partner wherein the mixing partner is selected from the group consisting of azoxystrobin, copper hydroxide, difenoconazole, ethaboxam, fludioxonil, fluopyram, fluoxastrobin, fluxapyroxad, inpyrfluxam, ipconazole, isoflucypram, mefenoxam, mefentrifluconazole, metalaxyl, myclobutanil, oxathiapiprolin, picoxystrobin, propiconazole, prothiaconazole, pydiflumetofen, pyroclostrobin, sedaxane, tebuconazole, thiabendazole, thiram, titriconazole and trifloxystrobin. Aspect E

Another aspect is a agrochemical composition comprising Fl and a mixing partner wherein the mixing partner is selected from the group consisting of abamectin, acetamiprid, afidopyropen, AI-1, AI-2, benpyrimoxan, bifenthrin, broflanilide, chlorantraniliprole, chlorfenapyr, clothianidin, cyantraniliprole, deltamethrin, dinotefuran, fipronil, flonicamid, fluazaindolizine, fluensulfone, flupyradifurone, flupyrimin, fluxametamide, heat-killed Burkholderia spp. Strain A 396, imidacloprid, indoxacarb, lambda cyhalothrin, m ethoxy fenozi de, oxamyl, pyriproxyfen, spinosad, spinetoram, spiromesifen, spirotetramet, sulfoxaflor, tetraniliprole, thiamethoxam, and triflumezopyrim.

Aspect F

Another aspect is an agrochemical composition comprising Fl and compound of Formula A below:

Compound of Formula A

In any of the pesticidal composition according to aspects A-F , the ratio of Fl to the mixing partner B) is selected from 1 :160,000 to 160,000:1, 1:80,000 to 80,000: 1, 1 :40,000 to 40,000: 1, 1 :20,000 to 20,000: 1, 1 : 10,000 to 10,000: 1, 1 :8000 to 8000: 1, 1 :5000 to 5000: 1, 1 :2000 to 2000: 1, 1 :1000 to 1000: 1, 1 :500 to 500: 1, 1 :250 to 250:1, 1: 100 to 100: 1; 1 :50 to 50:1, 1 :25 to 25: 1, l:10 to 10: 1, l:5 to 5:l, and 1 : 1. In one aspect, the seed treatment formulations disclosed herein comprise 0.2-2% w/w of a wetting agent, 2-10% w/w of a dispersing agent, 1-8% w/w of humectant, and 1-20% w/w of antifreeze agent.

Nonionic Surfactants: Nonionic surfactants, generally, may include alcohol ethoxylates, fatty acid esters, water-soluble adducts of polyethylene oxide with polypropylene glycol, di ethylenediaminopolypropylene glycol and alkylpolypropylene glycol. Examples of nonionic surfactants include polyoxyethylene sorbitan trioleate, polyoxyethylene-polyoxypropylene block copolymers, polygycol ether derivatives of aliphatic or cycloaliphatic alcohols or saturated or unsaturated fatty acids, polyethoxylated castor oil, polyadducts of polypropylene and polyethylene oxide, tributylphenol polyethoxylate, polyethylene glycol, acrylic graft copolymers, and polyoyalkylene copolymers. Alkylphenol ethoxylates (APEs), alcohol ethoxylates, ethylene oxide-propylene oxide (EO/PO) copolymers, alkyl polyglucosides (APGs);

Anionic Surfactants: Alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts of higher fatty acids. Examples of the preceding list include sodium salts of oleic or stearic acid. Additional anionic chemistries include alkyl aryl sulfonates, dialkyl sulfonates, dialkyl succinates, aryl sulfonates and condensation products thereof, alkyl sulfuric acid esters, alkyl phosphoric acid esters, alkylaryl sulfuric acid esters, alkylaryl phosphoric acid esters, polycarboxylates, polyoxyalkylene aryl ether sulfates, polyoxyalkylene aryl ether phosphates, polyoxyethylene ether phosphate, lignin sulfonates, ethoxylated tri styrylphenol phosphates. An example is an alkylnaphthalenesulfonate formaldhye condensate, alkylbenzene sulfonates (ABS), linear alkylbenzene sulfonates (LAS), alkyl sulfates (AS), alkyl ether sulfates (AES);

Amphoteric Surfactants: Alkyl betaines, alkyl amine oxides, alkyl imidazolinium betaines, amino acids, and lecithin; Silicone Surfactants: polyalkyleneoxide modified heptamethyltri siloxane, and organomodified trisiloxanes;

The dispersing agents are selected from the group consisting of polycarboxylates, naphthalene sulfonate formaldehyde condensates, lignosulfonates, polyvinylpyrrolidone, polysaccharides, polyoxyethylene sorbitan esters (Tweens), polyethylene glycols, block copolymers, alkylphenol ethoxylates (APEs);

The humectants are selected from the group consisting of glycerin, propylene glycol, sorbitol, urea, polyethylene glycol, ethylene glycol, and tri ethylene glycol. The antifreeze agents are selected from the group consisting of ethylene glycol, propylene glycol, glycerol, potassium formate, ethanol, methanol, and calcium chloride. Specific examples include propylene glycol and glycerine;

The seed treatment formulations disclosed herein comprise one or more of wetting agents, dispersing agents, antifoam agents, humectants, antifreeze agents, and film forming agents. In addition, the formulations also comprise typical seed treatment formulation excipients such as thickeners, viscosity modifiers, flow aids, colorants, and biocides. Generally, these formulation ingredients are present up to 10-15%w/w. In some instances, these formulation ingredients are present up to 10%w/w.

Accordingly, one aspect of the agrochemical formulations disclosed herein is a seed treatment formulation comprising compound of Formula One in up to 60%w/w, preferably up to 50%w/w, more preferably up to 40%w/w, l%-2%w/w of a wetting agent, 2%-6%w/w of a dispersing agent, 2%-6%w/w of humectant, and 2%-6% w/w of antifreeze agent. The formulations further comprise a film forming agent, a thickener, flow aid, colorant and a biocide. Generally, water is used as a carrier agent.

In one aspect, the composition includes at least one polymer selected from water-soluble and water-dispersible film-forming polymers. Suitable polymers have an average molecular weight of at least about 1,000 up to about 100,000; more specifically at least about 5,000, up to about 100,000. The aqueous compositions generally contain from about 0.01% to about 10% by weight of the composition of water-soluble and water-dispersible film-forming polymer. In a specific aspect, the compositions contain from about 1.0% up to about 5% by weight of a filmforming polymer. Suitable polymers are selected from polyalkyleneglycol including the polypropylene glycols and polyethylene glycols; alkyleneoxide random and block copolymers such as ethylene oxi de-propylene oxide block copolymers (EO/ PO block copolymers) including both EO-PO-EO and PO-EO-PO block copolymers; ethylene oxide-butylene oxide random and block copolymers; C2-C6 alkyl adducts of ethylene oxide-propylene oxide random and block copolymers; C2-C6 alkyl adducts of ethylene oxi de-butylene oxide random and block copolymers; polyoxyethylene-polyoxypropylene monoalkylethers such as methyl ether, ethyl ether, propyl ether, butyl ether or mixtures thereof; vinylacetate/vinylpyrrolidone copolymers, alkylated vinylpyrrolidone copolymers; and polyvinylpyrrolidone; natural polymers such as collagen, latex; and polysaccharides including starch, glycogen, cellulose, chitin, including xanthan gum, dextran, welan gum, gellan gum, diutan gum and pullulan. Specific examples of suitable polymers include Agrimer 30 (Ashland), Agrimer 90 (Ashland), Agrimer 120 (Ashland), Agrimer VA 31 (Ashland), Agrimer VA 51 (Ashland), Agrimer VA 6 (Ashland), Agrimer VA 71 (Ashland), Selvol 24-203 (Sekisui), Selvol 203S (Sekisui), Selvol 21-205 (Sekisui), Selvol 205S (Sekisui), Selvol Ultiloc 4005 (Sekisui), ELVANOL 51-05 (DuPont), GOHSENOL GL03 (Nippon Gohsei), Mowiol 44-88 (Kuraray America), Polyvinyl Alcohol (British Traders & Shippers Ltd.), Poval 5-88 (Kuraray), Grindsted Xanthan 80 (Danisco), Kelzan (CP Kelco), Kelzan AR (CP Kelco), Kelzan D (CP Kelco), Kelzan S (CP Kelco), Rhodopol 23 (Solvay), Rhodopol 50 MC (Solvay), Xanthan Gum TGRD (Jungbunzlauer), and Lattice NTC 65 (International Flavors & Fragrances).

In a further aspect, the formulations disclosed herein comprise preservatives / biocides. Examples of the biocides / preservatives include parabens, sorbic acid salts, 5-chloro-2-methyl- 4-isothiazolin-3-one, 2-Methyl-l,2-thiazol-3(2H)-one, 2-bromo-2 -propan- 1,3-diol, 1,2- benzisothiazolin-3-one, sodium benzoate, sodium p-hydroxy benzoate and potassium sorbate, and any substance known for this application may be used singly or two or more thereof may be used in combination.

In light of the above disclosure, further details are provided below: dl. An agrochemical formulation comprising

A. a compound of Formula One; and

B. one or more agrochemically-acceptable excipients selected from the group consisting of a thickening agent, antifoam, biocide, wetting agent, dispersant and a diluent;

C. optionally another excipient selected from the group consisting of an antifreeze agent, a pH modifier, and a colorant; and wherein the concentration of the compound of Formula One in the formulation is 0.8% by weight to 70% by weight . d2. An agrochemical formulation comprising

A. a compound of Formula One; and

C. one or more adjuvants selected from the group consisting of fatty alcohol alkoxylates, ethoxylated alcohols, polysorbates, silicone-based surfactants, polymethylsiloxane copolymers, methylated seed oils, and mineral oil.;

C. optionally another excipient selected from the group consisting of an antifreeze agent, a pH modifier, and a colorant; and wherein the concentration of the compound of Formula One in the formulation is 0.8% by weight to 70% by weight . d3. An agrochemical formulation comprising

A. a compound of Formula One; and B. one or more agrochemically-acceptable excipients selected from the group consisting of a thickening agent, antifoam, biocide, wetting agent, dispersant and a diluent;

C. one or more adjuvants selected from the group consisting of an organomodified polyether trisiloxane and a polyethoxylated sorbitan ester;

C. and a pH modifier. d4. The agrochemical formulation according to dl-d3, wherein the concentration of the compound of Formula One is l%w/w to 55%w/w. d5. The agrochemical formulation according to dl-d3, wherein the concentration of the compound of Formula One is l%w/w to 35%w/w. d6. The agrochemical formulation according to any of the dl-d3, wherein the particle size of the compound of Formula One is less than or equal to 8 pm (Dv90). d7. The agrochemical formulation according to any of the dl-d3, wherein the particle size of the compound of Formula One is less than or equal to 3 pm (Dv90). d8. The agrochemical formulation according to any of the dl-d3, wherein the particle size of the compound of Formula One is less than or equal to 1 pm (Dv90). d9. The agrochemical formulation according to any of the dl -d3, wherein the particle size of the compound of Formula One is between 1 pm (Dv90) - 0.5 pm (Dv90). dlO. The agrochemical formulation according to any of the dl, further comprising an adjuvant. dl 1. The agrochemical formulation according to d2-d!0, wherein the adjuvant is a retention agent, spreading agent or an agent that is both a retention and spreading agent. dl2. The agrochemical formulation according to any of d2-dl 1, wherein the adjuvant is a retention agent. dl 3. The agrochemical formulation according to any of the d2-dl 1, wherein the adjuvant is a spreading agent. d!4. The agrochemical formulation according to any of the d2-dl 1, wherein the adjuvant is an agent that is both a retention and spreading agent. dl 5. The agrochemical formulation according to any of d2-d!4, wherein the adjuvant is a non-ionic surfactant. dl6. The agrochemical formulation according to any of the d2-dl4, wherein the adjuvant is selected from the group consisting of fatty alcohol alkoxylates, ethoxylated alcohols, polysorbates, silicone-based surfactants, polymethylsiloxane copolymers, methylated seed oils, and mineral oil. dl7. The agrochemical formulation according to any of d 1 -dl 6, wherein the particle size of the compound of Formula One is < 3 pm (Dv90), and further comprising an adjuvant selected from the group consisting of a retention agent, spreading agent and retention and spreading agent. dl 8. The agrochemical formulation according to any of dl-dl6, wherein the particle size of the compound of Formula One is < 1 pm (Dv90), and further comprising an adjuvant selected from the group consisting of a retention agent, spreading agent and an agent that is both a retention and spreading agent. dl9. The agrochemical formulation according to any of dl7-dl 8, wherein the concentration of the compound of Formula One is between 1% - 40%w/w. d20. The agrochemical formulation according to any of d2-dl9 wherein loading concentration of adjuvant is between 5%-30 % w/w. d21. The agrochemical formulation according to any of d2-dl9, wherein the concentration of the compound of Formula One is l-40%w/w and adjuvant concentration is 5%-30%w/w. d22. The agrochemical formulation according to any of d2-dl9, wherein the concentration of the compound of Formula One is 1%-35%W/W and adjuvant concentration is 5%-30%w/w. d23. The agrochemical formulation according to any d2-d22, comprising a mixture of two adjuvants, wherein the ratio between the two adjuvants is between 1 : 1 ratio and 4: 1 ratio. d24. The agrochemical formulation according to d23, wherein at least one adjuvant is a polyethoxylated sorbitan ester. d25. The agrochemical formulation according to d23, wherein at least one adjuvant is an organomodified polyether trisiloxane. d26. The agrochemical formulation according to d23, wherein one adjuvant is an organomodified polyether trisiloxane and other adjuvant is a polyethoxylated sorbitan ester. d27. The agrochemical formulation according to dl-d26, which is a suspension concentrate (SC) formulation. d28. The agrochemical formulation according to dl-d27, further comprising a pH modifier. d29. The agrochemical formulation according to claim d28, wherein the pH modifier is selected from the group consisting of citric acid, acetic acid, lactic acid, propionic acid, benzoic acid, salicylic acid, gluconic acid, tartaric acid, fumaric acid, maleic acid, succinic acid, oxalic acid, malic acid, glycolic acid, 2-amino-2-methyl-l -propanol (AMP), monoethanolamine, diethanolamine, piperazine, morpholine, and tromethamine (TRIS base). d30. The agrochemical formulation according to any of the claims dl-d29, wherein the particle size the compound of Formula One is more than or equal to 8 pm (Dv90). d31. The agrochemical formulation according to dl, further comprising at least one of a colorant, flow aid and a film forming or polymeric binder. d32. The agrochemical formulation according to d31, which is a seed treatment formulation. d33. The agrochemical formulation according to d32, which is a flowable concentrate for seed treatment (FS). d34. The agrochemical formulation according to any of d31 -d33 , further comprising an additional active selected from the group consisting of insecticides, fungicides, and nematicides. d35. A method of using the agrochemical formulation according to any of dl-d34 to prevent, mitigate, combat or eliminate a pest or pest infestation, comprising the step of applying the agrochemical formulation according to any of dl-d34 to the locus where the pest inhabits or the locus of the pest infestation. d36. Use of the agrochemical formulation according to any of dl-d34 to prevent, mitigate, combat or eliminate a pest or pest infestation, comprising of applying the agrochemical formulation according to any of dl -d34 to the locus where the pest inhabits or the locus of the pest infestation.

Further details include the following: dl. An agrochemical formulation comprising

A. a compound of Formula One

Formula One

B. one or more agrochemically-acceptable excipients selected from the group consisting of a thickening agent, an antifoam, a biocide, a wetting agent, a dispersant and a diluent; and

C. optionally another excipient selected from the group consisting of an antifreeze agent, a pH modifier, and a colorant; and wherein the concentration of the compound of Formula One in the formulation is 0.8% by weight to 70% by weight. d2. The agrochemical formulation according to dl, wherein the concentration of the compound of Formula One is 1% w/w to 55% w/w. d3. The agrochemical formulation according to dl, wherein the concentration of the compound of Formula One is 1% w/w to 40% w/w. d4. The agrochemical formulation according to any of dl-d3, wherein the particle size of the compound of Formula One is less than or equal to 8 pm (Dv90). d5. The agrochemical formulation according to any of d 1 -d3, wherein the particle size of the compound of Formula One is less than or equal to 3 pm (Dv90). d6. The agrochemical formulation according to any of dl-d3, wherein the particle size of the compound of Formula One is less than or equal to 1 pm (Dv90). d7. The agrochemical formulation according to any of dl-d3, wherein the particle size of the compound of Formula One is between 1 pm (Dv90) - 0.5 pm (Dv90). d8. The agrochemical formulation according to any of dl-d7, further comprising an adjuvant. d9. The agrochemical formulation according to d8, wherein the adjuvant is a retention agent, spreading agent or an agent that is both a retention and spreading agent. dlO. The agrochemical formulation according to any of d8-d9, wherein the adjuvant is a retention agent. dl l. The agrochemical formulation according to any of d8-d9, wherein the adjuvant is a spreading agent. dl2. The agrochemical formulation according to any of d8-d9, wherein the adjuvant is both a retention and spreading agent. dl 3. The agrochemical formulation according to any of d8-d!2, wherein the adjuvant is a nonionic surfactant. dl4. The agrochemical formulation according to any of d8-dl3, wherein the adjuvant is selected from the group consisting of fatty alcohol alkoxylates, ethoxylated alcohols, polysorbates, silicone-based surfactants, polymethylsiloxane copolymers, methylated seed oils, and mineral oil. dl 5. The agrochemical formulation according to any of dl-dl4, wherein the particle size of the compound of Formula One is < 3 pm (Dv90), and further comprising an adjuvant selected from the group consisting of a retention agent, spreading agent and retention and spreading agent. dl6. The agrochemical formulation according to any of dl -dl 4, wherein the particle size of the compound of Formula One is < 1 pm (Dv90), and further comprising an adjuvant selected from the group consisting of a retention agent, spreading agent and retention and spreading agent. dl 7. The agrochemical formulation according to any of dl 5-d 16, wherein the concentration of the compound of Formula One is between 1% - 40%w/w. dl 8. The agrochemical formulation according to any of d8-dl7 wherein loading concentration of adjuvant is between 5%-30%w/w. dl 9. The agrochemical formulation according to any of d8-dl6, wherein the concentration of the compound of Formula One is l%-40%w/w and adjuvant concentration is 5%-30%w/w. d20. The agrochemical formulation according to any of d8-dl9, wherein the concentration of the compound of Formula One is 1 %-35% w/w and adjuvant concentration is 5%-30% w/w. d21. The agrochemical formulation according to any of d8-d20, comprising a mixture of two adjuvants, wherein the ratio between the two adjuvants is between 1 : 1 and 4: 1. d22. The agrochemical formulation according to dl -d21 , which is a suspension concentrate (SC) formulation. d23. The agrochemical formulation according to dl, further comprising a colorant, flow aid and a film forming or polymeric binder. d24. The agrochemical formulation according to d23, which is a seed treatment formulation. d25. The agrochemical formulation according to d24, which is a flowable concentrate for seed

(FS) treatment. d26. The agrochemical formulation according to any of d22-d25, further comprising an additional active selected from the group consisting of insecticides, fungicides, nematicides and biologicals. d27. The agrochemical formulation according to d26, wherein the further active is an insecticide selected from the group consisting of chlorantraniliprole and cyantraniliprole. Additionally, in a particular aspect, the agrochemical formulations disclosed herein is selected from the group consisting of:

A) an agrochemical composition comprising compound of Formula One in 5% - 20%w/w; A) ethylene oxide - propylene oxide copolymer in 2%-10%w/w B) and branched alcohol ethoxylate in 0.1%-1.0%w/w.

B) an agrochemical composition comprising compound of Formula One in 5% - 20%w/w; A) acrylic graft copolymer copolymer in 2%-10%w/w B) and sodium alkyl naphthalene sulfonate blend in 0.5%-4.0%w/w.

C) is an agrochemical composition comprising compound of Formula One in 10% - 30% w/w; A) ethylene oxide - propylene oxide copolymer in 1%-10%W/W B) sodium alkyl naphthalene sulfonate blend in 1%-10%W/W; and C) sodium alkyl naphthalene sulfonate blend 0.1%-2.0%w/w.

D) is an agrochemical composition comprising compound of Formula One in 5% - 20%w/w;

A) acrylic graft copolymer copolymer in 2%-10%w/w B) branched alcohol ethoxylate in 0.1%-2.0%w/w C) at least one polyethylene sorbitan D) at least one organomodified polyether trisiloxane and E) at least one alcohol alkoxylate.

E) Disclosed herein is an agrochemical composition comprising compound of Formula One in 5% - 20%w/w; A) ethylene oxide - propylene oxide copolymer in 0.5%-10%w/w B) sodium alkyl naphthalene sulfonate blend in 0-2%w/w C) at least one polyethylene sorbitan and D) at least one organomodified polyether trisiloxane .

F) An agrochemical composition comprising: a. from 3% to 55% by weight of a compound of Formula One; b. from 0.1% to 5% by weight of an anionic surfactant; and c. from 0.1% to 22% by weight of a nonionic surfactant.

G) An agrochemical composition comprising: a. from 30% to 50% by weight of a compound of Formula One; b. from 1% to 5% by weight of one or more anionic surfactants; c. from 0.5% to 2% by weight of one or more nonionic surfactants; d. from 2% to 6% by weight of a humectant; e. from 0.2% to 0.4% by weight of an antifoam agent; and f. from 0.05% to 0.6% by weight of one or more rheology modifiers. H) An agrochemical composition comprising: a. from 5% to 15% by weight of a compound of Formula One; b. from 25% to 40% by weight of chlorantraniliprole; c. from 3% to 5% by weight of one or more anionic surfactants; and d. from 0.5% to 2% by weight of one or more nonionic surfactants;

EXPERIMENTAL SECTION:

Example 1: Milling process and millbase preparation for suspension concentrate formulations with particle size Dv(90) < 8 pm, Dv(90) < 3 pm and Dv(90) < 1 pm

This example provides a composition, according to the present invention, which is a millbase of compound of Formula One and which may be used to prepare further compositions or formulations according to the present invention. The method of preparation of suspension concentrate formulations and suspension concentrate millbases are known in the art and can be produced by those known methods familiar to those skilled in the art.

Suspension concentrate mill base (i.e., compound of Formula One mill base) can include well known formulation additives such as powder viscosity modifier, biocide, surfactants, antifreeze, and antifoam agent.

In this example, water was added to a formulation vessel and mixed at ambient temperature. A powder viscosity modifier was added and the mixture was stirred until the viscosity modifier was fully incorporated, identified by no clumps of powder and a visual increase in viscosity observed. An antifreeze, an antifoam agent, a wetting agent, surfactants, and a biocide were added with continued mixing. After mixing, the compound of Formula One was added to the formulation vessel and mixed until the active was completed wetted.

In each instance, after full incorporation of active into aqueous medium, higher shear mixing (Silverson high-shear mixer) was utilized to reduce particle size of compound of Formula One. The mixture was sheared continuously for 5 minutes. Once high-shear mixing was completed, the mixture was transferred to a horizontal bead until the desired Dv(90) particle size was achieved as measured by laser diffraction particle size analyzer (e.g., Malvern Mastersizer 3000) and/or dynamic light scattering particle size analyzer (e.g., Malvern Nanosizer)..

The concentration of the components added to form the millbase of Example 1 are listed in the below Table 1, and are expressed as percentage by weight over the total weight of compound of Formula One millbase.

Millbase composition for suspension concentrate for compound of Formula One (Table 1)

Example 2. Suspension concentrate formulation without adjuvants

This example provides a suspension concentrate formulation without adjuvant according to the present invention. Once particle size is achieved, remaining formulation components are combined to produce a suspension concentrate formulation. The following components were added to a vessel: water, antifreeze, antifoam, biocide (or biocides), millbase from example 1 and viscosity modifier. The components were all mixed with an overhead mixer. The biocide, antifreeze, antifoam agent, viscosity modifier, and wetting agents are all known to those skilled in the art. The final concentrations of components are shown in Table 2, and all are expressed in percentage by weight over the total weight of the suspension concentrate.

Suspension concentrate formulation without adjuvants (Table 2) Example 3. Suspension concentrate formulation with adjuvant

This example provides a suspension concentrate formulation with adjuvant according to the present invention. Once particle size is achieved, remaining formulation components are combined to produce a suspension concentrate formulation. The following components were added to a vessel: water, antifoam, biocide (or biocides), optionally a pH modifier, optionally an anttifreeze, millbase from example 1 and viscosity modifier. The components were all mixed with an overhead mixer until viscosity modifier was well incorporated. Then adjuvants were added and the mixture was thoroughly mixed with an overhead mixer. The biocide, antifreeze, antifoam agent, and viscosity modifier are all known to those skilled in the art.

The final concentration of components are shown in Table 3, and all are expressed in percentage by weight over the total weight of the suspension concentrate.

Suspension concentrate formulation with adjuvant (Table 3) Example 4 - 16. Particle size stability data/comparison of the above formulations

Particle size stability protocol:

To evaluate the temperature-stability of the samples, formulations were stored in a temperature controlled oven set at 54 °C for 2 weeks or an oven set on a 4 week cycle between freezing and thawing (4 weeks F/T). More specifically, this oven ramps in a cycle from -10 °C for 2 weeks and 40 °C for 2 weeks. The physical stability of samples characterized by assessing particle size growth in comparison to ambiently stored samples. Ambient temperature refer to samples stored at room temperature. Particle size was assessed by laser diffraction particle size analyzer (e. ., Malvern Mastersizer 3000).

Particle size stability assessment of suspension concentrate without adjuvant (Table 4)

5 The concentrations of the components in Examples 4 - 8, expressed in percentage by weight over the total weight of the composition, as well as particle size are shown in Table 4. A range of dispersant chemistries can be selected to stabilize compound of Formula One in an aqueous suspension. It is noted that poly(ethylene oxide)-poly(propylene oxide) co-polymers with higher molecular weight more effectively stabilizing lower Dv(90) particle sizes as demonstrated by comparison of Example 6 and Example 7.

Particle size stability assessment of suspension concentrate with adjuvant (Table 5)

The concentrations of the components in Examples 9 - 16, expressed in percentage by weight over the total weight of the composition, as well as particle size are shown in Table 5. A range of dispersant chemistries can be selected to stabilize compound of Formula One in an aqueous suspension, with poly(ethylene oxide)-poly(propylene oxide) co-polymers with higher molecular weight more effectively stabilizing lower Dv(90) particle sizes when pH modifier is introduced. This is demonstrated by comparison of

comparative particle size growth from ambient storage and 4 week freeze / thaw cycle of Example 14 and Example 16. Significantly larger particle size growth is observed for Example 14 (lower molecule weight poly(ethylene oxide)-poly(propylene oxide) copolymer and pH modifier) as compared to Example 16 (higher molecular weight polyethylene oxide)-poly(propylene oxide) copolymer and pH modifier).

Example 17 - 20. Shelf-life assessment of suspension concentrate with adjuvant

Shelf-life stability protocol: To evaluate the temperature-stability of the samples, formulations were stored in a temperature controlled oven set at 54 °C for 2 weeks. The chemical stability of compound of Formula One in formulation samples was assessed using methods known to those skilled in the art, specifically high-performance liquid chromatography to assess concentration of compound of Formula One in a formulation sample stored at ambient compared to sample stored at 54 °C for 2 weeks.

Chemical stability assessment for compound of Formula One (Table 6)

The concentrations of the components in Examples 17 - 20 are expressed in percentage by weight over the total weight of the composition in Table 6. All compositions of Examples 17 - 20 contain both a retention aid adjuvant and a spreading aid adjuvant. The chemical stability of compound of Formula One can be tracked comparatively to pH.

It is noted that pH plays a role in ensuring longer shelf-life of the formulated product as indicated by the chemical stability of compound of Formula One. As the undiluted formulation pH is reduced below 7, the chemical stability of compound of Formula One improves (Table 6). As the undiluted formulation pH is reduced below 6, the stability of compound of Formula One even more greatly improves. The greatest chemical stability of compound of Formula One is observed with undiluted formulation pH below 5 (Table 6). Overall, lower percent loss of compound of Formula One after storage at 54 °C for 2 weeks is a proxy for indicating long shelflife. Suitable pH modifiers for use in the formulation include, but are not limited to, organic acids analogous to citric acid. Examples include lactic acid, a mild, biodegradable acid; and acetic acid, a simple carboxylic acid providing effective acidification but with potential volatility considerations. Tartaric acid and malic acid are both dicarboxylic acids offering moderate acidity and good water solubility, making them suitable substitutes for citric acid. Fumaric acid provides stronger acidification though it has lower solubility, while succinic acid enables gentle pH adjustment with minimal impact on stability. Gluconic acid, a weak organic acid derived from glucose oxidation, offers mild acidification and potential chelating benefits. Formic acid is a stronger acid but may require careful use to avoid hydrolysis of sensitive actives. Ascorbic acid (vitamin C) may also be used, offering the added benefit of antioxidative protection. Among these, tartaric acid, malic acid, salicylic acid, malonic acid and lactic acid are particularly preferred for achieving optimal pH control while maintaining formulation stability.

Dynamic surface tension assessment for shelf-life (Table 7)

The concentrations of the components in Examples 18 - 20 are expressed in percentage by weight over the total weight of the

5 composition in Table 7. An organomodified polysiloxane spreading aid adjuvant is present in Examples 18 - 20. The dynamic surface tension of a 0.25% volume per volume solution of formulation in water as compared to pH of an undiluted formulation stored at ambient temperature is also shown in Table 7.

Dynamic surface tension (DST) measurements serve as a useful proxy for assessing the effectiveness and overall stability of spreading aid adjuvants. Effective spreading aids lower the dynamic tension as surfactants accumulate at the air-water interface,

10 reducing the cohesive forces between water molecules. As such, the lower the dynamic surface tension the more effective spreading is observed.

It has been unexpectedly found that certain combinations of adjuvants and pH modifiers can increase the dynamic surface tension (DST) of a formulation comprising a spreading aid. More specifically, as the pH is reduced the dynamic surface tension increases. This is specifically observed when comparing Example 18 to Example 20. Example 18 has the highest undiluted formulation pH and it is noted that it has the lowest DST of all samples. In comparison, the highest DST (z.e., less effective spreading)

5 is observed for Example 20 which has the lowest undiluted formulation pH. Without wishing to be bound by theory, it is believed that the interaction between specific adjuvants and the pH environment impacts the stability and integrity of the spreading aid effectively modulating molecular organization of the spreading aid at the air-liquid interface. Thus, DST measurements serve as a useful proxy for predicting the stability of spreading aid over time.

Given the unique challenges associated with the chemical stability of compound of Formula One (Table 6) as well as the 10 stability of the spreading aid (Table 7), an optimal pH range must be targeted to ensure shelf-life stability of the formulated product. Combinations of adjuvants such as block copolymer surfactants, sulfonated dispersants, and selected organic acids as pH modifiers (e.g., citric acid, tartaric acid) have demonstrated particular efficacy in maintaining desirable DST profiles and stability of compound of Formula One, thereby contributing to improved overall formulation robustness.

Example 21. Rainfastness comparison between formulation comprising adjuvants and a control formulation

Rainfastness protocol for evaluation of rainfastenss of suspension concentrate formulations on cabbage leaves:

Formulation dilutions were prepared at concentrations representative of a typical use rate. Formulation dilution is then directly added onto the leaf surface using a pipette in the form of 10 pL droplets amounting to a total volume of 50 pL of formulation dilution. Cabbage leaves are placed in a horizontal position and droplets are allowed to dry for 2 hours at room temperature (21-22°C) in a fume hood at an air face velocity of 100 ft/min. After droplets have dried, leaves are placed on platform and subjected to overhead water spray for 15 minutes with 25 mm of rain, simulating approximately 105 mm per hour of rain. After rain application, leaves are collected and prepared for analytical measurements. Leaves are transferred to ball milling container filled with 5 mL of an 80% acetonitrile solution in water and stainless-steel beads. Leaves are subjected to bead milling until leaves are fully digested. Extract is then assessed via high- performance liquid chromatography. Concentration of active material on leaves subjected to artificial rainfall are compared to the concentration of active on leaves that were not subjected to artificial rainfall (z.e., control) to calculate % recovery.

Summary of rainfastness comparison of SC without adjuvant (Example 5) and SC with adjuvant (Example 9 and Example 10) (Table 8)

Rainfastness of a formulation denominates the formulation’s ability to resist active ingredient wash-off by rain. In this context, rainfastness can directly relate to retention of an active. Improved rainfastness results in increased retention of active ingredient after deposit on leaf surface. To quantitatively compare the rainfastness of a formulation, comparison of the percent recovery of active on a leaf surface that has been subjected to artificial rainfall can be completed. Comparison of the percent recovery of compound of formulation one in an SC without adjuvant (Example 5) and SC formulations with adjuvant (Example 9 and Example 10) demonstrates that the inclusion of adjuvant results in numerically greater rainfastness of compound of Formula One on cabbage leaf surface after artificial rainfall. Comparison of Example 9 and Example 10 also demonstrate numerically improved rainfastness with lower Dv(90) particle size. Assessments were completed with ambiently stored samples and, as such, particle sizes of these samples (Example 9 and Example 10) correlate to are shown in Table 4 and Table 5.

Example 22 - 23. Retention comparison of suspension concentration formulation with and without adjuvant

Quantitative foliar retention testing protocol:

Plants selected for assessment are grown to the first true leaf stage. 1-4 plants are utilized per treatment. Formulation dilutions are prepared and plants are treated using a track sprayer calibrated to 200 liters per hectare application volume resulting in application of 50 grams active ingredient per hectare. Active ingredient refers to compound of Formula One. The spray plants are allowed to sit at ambient temperature for 1 hour after application prior to additional processing. Once 1 hour interval has been completed leaf discs are harvested (using a 1/6” diameter borer) from 4 leaves for each treatment and placed in a tube. This is completed in triplicate for each treatment. The leaf tissue is processed through grinding with 80% acetonitrile 20% water solution. The sample are centrifuged and supernatant is assessed via liquid chromatography - mass spectrometry for quantification.

Key compositional differences (adjuvants) for retention assessment (Table 9)

The concentrations of the components in Examples 5 and Examples 22 - 23 are expressed in percentage by weight over the total weight of the composition in Table 9.

Summary of foliar spray retention of suspension concentrate formulations without adjuvant (Example 5) and with adjuvant (Example 22 and Example 23) on cabbage (Table 10) Inclusion of adjuvant into suspension concentrate formulations with compound of Formula One results in increased foliar retention (z.e., reduction in bounce-off of spray droplets). This is shown in comparison of Example 5 to Example 22 and Example 23.

Example 24. Biological efficacy protocol for suspension concentration formulation using track spray in laboratory greenhouse for foliar application

Biology data for all materials tested were collected at two different rates (10 and 2.5g/Ha) using a track sprayer assay with three insect species on cabbage leaf. The three target insect species were all tested at the 2nd instar life stage with a sample size of 16 insects per species per treatment. Cabbage plants were grown to the two-leaf stage and treated as whole plants, utilizing twelve plants per treatment. Plants were treated on a Mandel Track Sprayer at 200 L/Ha with a spray height of 40 cm. After application of materials, plants were allowed to dry for 1 h at ambient conditions in the spray room. Subsequently, the two leaves were clipped from each plant into labeled wells of a 32-well plastic tray with a thin layer of 1.0% agar covering the bottom of each well to prevent desiccation of the leaves. Each well was then infested with two insect larvae and sealed with a removable lid. Trays are held in a controlled environment holding room for three days at approximately 26°C with 16 hours of light. Mortality/morbidity evaluations are conducted at three days after infestation (DAI).

Biological efficacy of exemplary suspension concentrate formulations without adjuvant (Example 5) and with adjuvant (Example 11) (Table 11) Example 25. Milling process for flowable concentrate for seed treatment

In this example, formulation components in mill base were added to a vessel and stirred with an overhead mixer equipped with Cowles blade at ambient temperature till uniform: further mixing with homogenizer is optional. The mixture was transferred to a bead mill and was milled until the desired particle size was achieved. The remaining formulation components were added to the collected mixture followed by agitation with an overhead mixer until the components were uniformly incorporated.

Flowable concentrate comprising compound of Formula One for seed treatment a) Specific embodiment of flowable concentrate for seed treatment without built-in colorant at 40% w/w compound of Formula One b) Specific embodiment of flowable concentrate for seed treatment without built-in colorant at 55% w/w compound of Formula One c) Specific embodiment of flowable concentrate for seed treatment with built-in colorant d) Specific embodiment of flowable concentrate for seed treatment premixture of compound of Formula One with chlorantraniliprole without built in colorant e) Specific embodiment of flowable concentrate for seed treatment premixture of compound of Formula One with chlorantraniliprole and inclusion of built-in colorant f) Specific embodiment of flowable concentrate for seed treatment without built-in colorant at 35% w/w compound of Formula One g) Specific embodiment of flowable concentrate for seed treatment with built-in colorant at 10% w/w compound of Formula One

These formulations are stable and possess a longer shelf-life, easy to use, and suitable for a variety of intended seeds. They have greater compatibility with other seed treatment products, including active molecules such as other insecticides, fungicides, nematicides and biological agents and meet typical requirements of seed treatment use.

Claims

CLAIMS:

1. An agrochemical formulation comprising

A. a compound of Formula One

Formula One

C. optionally another excipient selected from the group consisting of an antifreeze agent, a pH modifier, and a colorant; and wherein the concentration of the compound of Formula One in the formulation is 0.8% by weight to 70% by weight.

2. The agrochemical formulation according to claim 1, wherein the concentration of the compound of Formula One is 1% w/w to 55%w/w.

3. The agrochemical formulation according to claim 1, wherein the concentration of the compound of Formula One is 1% w/w to 40%w/w.

4. The agrochemical formulation according to any of the claims 1-3, wherein the particle size of the compound of Formula One is less than or equal to 8 pm (Dv90).

5. The agrochemical formulation according to any of the claims 1-3, wherein the particle size of the compound of Formula One is less than or equal to 3 pm (Dv90).

6. The agrochemical formulation according to any of the claims 1-3, wherein the particle size of the compound of Formula One is less than or equal to 1 pm (Dv90).

7. The agrochemical formulation according to any of the claims 1-3, wherein the particle size of the compound of Formula One is between 1 pm (Dv90) - 0.5 pm (Dv90).

8. The agrochemical formulation according to any of the claims 1-7, further comprising an adjuvant.

9. The agrochemical formulation according to claim 8, wherein the adjuvant is a retention agent, spreading agent or an agent that is both a retention and spreading agent.

10. The agrochemical formulation according to any of the claims 8-9, wherein the adjuvant is a retention agent.

11. The agrochemical formulation according to any of the claims 8-9, wherein the adjuvant is a spreading agent.

12. The agrochemical formulation according to any of the claims 8-9, wherein the adjuvant is both a retention and spreading agent.

13. The agrochemical formulation according to any of the claims 8-12, wherein the adjuvant is a non-ionic surfactant.

14. The agrochemical formulation according to any of the claims 8-13, wherein the adjuvant is selected from the group consisting of fatty alcohol alkoxylates, ethoxylated alcohols, polysorbates, silicone-based surfactants, polymethyl siloxane copolymers, methylated seed oils, and mineral oil.

15. The agrochemical formulation according to any of the claims 1-14, wherein the particle size of the compound of Formula One is < 3 pm (Dv90), and further comprising an adjuvant selected from the group consisting of a retention agent, spreading agent and retention and spreading agent.

16. The agrochemical formulation according to any of the claims 1-14, wherein the particle size of the compound of Formula One is < 1 pm (Dv90), and further comprising an adjuvant selected from the group consisting of a retention agent, spreading agent and retention and spreading agent.

17. The agrochemical formulation according to any of the claims 15-16, wherein the concentration of the compound of Formula One is between 1 - 40% w/w.

18. The agrochemical formulation according to any of the claims 8-17 wherein loading concentration of adjuvant is between 5-30 %w/w.

19. The agrochemical formulation according to any of the claims 8-16, wherein the concentration of the compound of Formula One is 1-40% w/w and adjuvant concentration is 5- 30%

20. The agrochemical formulation according any of the claims 8-19, further comprising a pH modifier.

21. The agrochemical formulation according to claim 20, wherein the pH modifier is selected from the group consisting of citric acid, lactic acid, malonic acid, maleic acid, phosphoric acid, oleic acid, salicylic acid, acetic acid, and fumaric acid.