Fungicidal formulations containing ARYL amidines and methods of use
Fungicidal formulations with 4-(difluoromethoxy)benzyl 4-(((ethyl(methyl)amino)methylene)amino)-2,5-dimethylbenzoate address stability and safety issues, offering effective fungal control with minimal crop harm through innovative formulation types and adjuvants.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- CORTEVA AGRISCIENCE LLC
- Filing Date
- 2025-11-04
- Publication Date
- 2026-05-15
AI Technical Summary
Existing fungicidal formulations face challenges in achieving stability, ease of use, safety, and effectiveness in protecting plants from agriculturally relevant fungi while minimizing harm to desirable crops.
Development of fungicidal formulations containing 4-(difluoromethoxy)benzyl 4-(((ethyl(methyl)amino)methylene)amino)-2,5-dimethylbenzoate or its acceptable salts, solvates, and hydrates, formulated in various forms such as emulsifiable concentrates, emulsion-in-water, and suspo-emulsions, which include adjuvants like Hallcomid® M-10 for enhanced efficacy.
The formulations provide effective protection against fungal diseases in crops and other plant locations with improved stability, user-friendliness, and safety, while maintaining minimal impact on desirable vegetation.
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Abstract
Description
FUNGICIDAL FORMULATIONS CONTAINING ARYL AMIDINES AND METHODS OF USECROSS REFERENCE TO RELATED APPLICATION
[0001] This application claims the benefit of U.S. Provisional Patent Application Serial No. 63 / 718,607 filed November 9, 2024, which is expressly incorporated by reference herein.FIELD
[0002] The present disclosure is directed to fungicidal formulations containing 4- (difluoromethoxy)benzyl 4-(((ethyl(methyl)amino)methylene)amino)-2,5-dimethylbenzoate (Formula I) or an acceptable salt, solvate, or hydrate thereof, and methods of using the fungicidal formulations thereof to treat and control fungal diseases or disorders in agriculture. Also disclosed herein are fungicidal formulations containing 4-(difluoromethoxy)benzyl 4- (((ethyl(methyl)amino)methylene)amino)-2,5-dimethylbenzoate hydrochloride (Formula I-B).BACKGROUND
[0003] Many recurring problems in agriculture involve protecting and / or curing plants against damage caused by agriculturally relevant fungi. To help protecting and / or curing plants, researchers have produced a variety of fungicidal chemicals effective in protecting and / or curing plants against damage caused by agriculturally relevant fungi. While these fungicidal chemicals may be used neat, it is typically preferable to incorporate the fungicidal chemicals in formulations. Such formulations may be liquid formulations or solid formulations. Such formulations can be designed to be stable under typical storage conditions; easy for the end user to transport, dilute, mix, and apply; safe for the end user and the environment; effective in protecting and / or curing plants against damage caused by agriculturally relevant fungi; and no or minimum damage or injury on desirable crops. Achieving most or all of these goals can be challenging. Therefore, there is an ongoing need for fungicidal formulations that are stable, easy to use, and safe.SUMMARY
[0004] In some aspects of the disclosure herein provide fungicidal formulations comprising the compound of Formula I or an acceptable salt, solvate, or hydrate thereof to protect and / or cure plants against damage caused by agriculturally relevant fungi. The disclosure also relates to processes for the preparation of these formulations, and to their use in the treatment and control of fungal diseases or disorders in agriculture.
[0005] In some aspects of the disclosure herein provide fungicidal formulations comprising a fungicidal compound of the Formula I:Formula I or an acceptable salt, solvate, or hydrate thereof.
[0006] In some aspects of the disclosure herein provide fungicidal formulations comprising an acceptable fungicidal salt of a compound of Formula I, where the acceptable fungicidal salts of Formula I include but not limited to hydrochloride, hydrobromide, sulfate, phosphate, trifluoroacetate, formate, citrate, maleate, oxalate, tartrate, fumarate, or combinations thereof.
[0007] In some aspects of the disclosure herein provide fungicidal formulations comprising an acceptable fungicidal salt of a compound of Formula I, where the acceptable fungicidal salts of Formula I is the hydrochloride salt (Formula I-B):Formula I-B
[0008] Applicants have found that compounds of Formula I, or an acceptable salt, solvate, or hydrate thereof, disclosed in the present disclosure exhibit fungicidal activity against damage caused by agriculturally relevant fungi. In some aspects, the acceptable fungicidal salt of Formula I is the hydrochloride salt (Formula I-B).
[0009] Throughout the disclosure, reference to the compounds of Formula I is read as also including all acceptable salts, solvates, hydrates, and mixtures thereof; reference to the compounds of Formula I-B is read as also including all solvates, hydrates, and mixtures thereof.
[0010] Throughout the disclosure, reference to the compounds of Formula I and Formula I-B is read as also including all regioisomers, structural isomers, geometrical isomers, rotational isomers, tautomers, and stereoisomers, for example diastereomers, enantiomers, and mixtures thereof.
[0011] The compounds of Formula I and Formula I-B may also contain linkages (e.g., carbon-carbon bonds) wherein bond rotation is restricted about that particular linkage e.g., restriction resulting from the presence of a ring or a double bond. Accordingly, any cis / trans and E / Z isomers are expressly included in the present disclosure.
[0012] The compounds of Formula I and Formula I-B may also be present in multiple tautomeric forms. Where one or more tautomeric forms exist, the disclosure expressly includes all such tautomeric forms of the compounds described herein, even though only a single tautomeric form may be represented.
[0013] The compounds of Formula I and Formula I-B may exist in one or more crystalline or polymorphic forms. All crystalline forms and polymorphs of the compounds of the disclosure are expressly included in the present disclosure.
[0014] In some aspects, the pesticidal formulation of the compounds of Formula I, or an acceptable salt, solvate, or hydrate thereof, may be present in suspended, emulsified, dissolved, or solid form. In some aspects, the acceptable fungicidal salt of Formula I is the hydrochloride salt (Formula I-B). Exemplary formulations include, but are not limited to, soluble liquid concentrates, aqueous suspension concentrates, oil-in-water emulsions, oil-in-water microemulsions, aqueous suspo-emulsions, water-in-oil emulsion, water-in-oil microemulsions, oil suspensions, emulsifiable concentrates, self-emulsifying formulations, pastes, gels, powders, dusts, granules, water-dispersible granules, wettable granules, wettable powders, and materials for spreading. In some aspects, the formulation can be provided as a fungicidal concentrate. In some aspects, the formulation can be provided as a ready-to-use composition.
[0015] In some preferred aspects, the pesticidal formulation of the compounds of Formula I, or an acceptable salt, solvate, or hydrate thereof, may be present in the form of emulsifiable concentrate (EC), emulsion-in-water (EW), suspo-emulsion (SE), microemulsion (ME), soluble concentrate (SL), or capsule suspension (CS). In some more preferred aspects, the pesticidal formulation of the compounds of Formula I, or an acceptable salt, solvate, or hydrate thereof, may be present in the form of emulsifiable concentrate (EC), emulsion-in-water (EW), or suspo-emulsion (SE).
[0016] In some alternatively preferred aspects, the pesticidal formulation of an acceptable salt of the compounds of Formula I may be in the form of suspension concentrate (SC) or water- dispersible granule (WDG).
[0017] In some aspects, the formulation can further comprise an agriculturally acceptable adjuvant or carrier, an additional fungicide, or combinations thereof.
[0018] In some aspects, the formulation may further comprise multifunctional ingredients. For example, some emulsifiers are known to be also adjuvants, antifoam agents, or wetting agents. Multifunctional ingredients are desirable in the field for reasons such as formulation optimization, cost reduction, efficacy boost, and so on. In some preferred aspects, the multifunctional aspects of an ingredient are unexpected. For example, some ingredients are not known to have multifunctional aspects but can be discovered to have surprising additional functions in some specific formulations. It is most useful when an ingredient has surprising additional functions specific to the active ingredients. Disclosed herein is that the solvent Hallcomid® M-10 can be an adjuvant in formulations containing the compound of Formula I. The disclosure herein provides an unexpected fungicidal formulation comprising a compound of Formula I and Hallcomid® M-10.
[0019] Also disclosed herein are methods of controlling plant derived fungal pathogens or diseases comprising contacting the contacting a seed, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and / or foliage of the plant to prevent the growth of the fungal pathogens or diseases with a fungicidal formulation comprising compounds of Formula I, or an acceptable salt, solvate, or hydrate thereof, disclosed herein. In some aspects, the acceptable fungicidal salt of Formula I is the hydrochloride salt (Formula I- B). In some aspects, the fungal pathogens or diseases are in croplands, orchards, lawns, pastures, gardens, and recreational areas. In some aspects, the fungal pathogens or diseases are in row crops. In some aspects, the fungal pathogens or diseases are in cereals. In some aspects, the fungal pathogens or diseases are in broadleaf crops. In some aspects, the fungal pathogens or diseases are in fruits. In some aspects, the fungal pathogens or diseases are in vegetables. In some aspects, the fungal pathogens or diseases are in nuts. In some aspects, the fungal pathogens or diseases are in maize, soy, canola, cotton, pulses, sunflower, flax, sugar beets, wheat, barley, rice, sorghum, millet, oats, strawberries, tomatoes, potatoes, apples, bananas, pumpkins, cucumbers, or peppers.
[0020] In some aspects, the fungicidal formulation is applied in any known technique for applying fungicides. Exemplary application techniques include, but are not limited to, spraying, atomizing, dusting, sprinkling, spreading, or direct application. The method of application can vary depending on the intended purpose. In some aspects, the method ofapplication can be chosen to ensure the finest possible distribution of the compositions disclosed herein.
[0021] In some aspects, the pesticidal formulation comprises the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, present in a liquid formulation at a concentration from 0.006 to 1000 gram active ingredient per liter (g ai / L) of the liquid formulation. In some aspects, the pesticidal formulation comprises the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, present in a solid formulation at a concentration from 0.006 to 950 gram active ingredient per kilogram (g ai / kg) of the solid formulation.
[0022] In some aspects, the pesticidal formulation comprises the compound of Formula I- B present in a liquid formulation at a concentration from 0.006 to 600 gram active ingredient per liter (g ai / L) of the liquid formulation. In some aspects, the pesticidal formulation comprises the compound of Formula LB present in a solid formulation at a concentration from 0.006 to 850 gram active ingredient per kilogram (g ai / kg) of the solid formulation.
[0023] The description below sets forth details of one or more aspect of the present disclosure. Other features, objects, and advantages will be apparent from the description and from the claims.DETAILED DESCRIPTION
[0024] The present disclosure includes pesticidal formulations comprising compounds of Formula I, or an acceptable salt, solvate, or hydrate thereof, as pesticides to protect and / or cure plants against damage caused by agriculturally relevant fungi in various locations, such as croplands, orchards, lawns, pastures, gardens, and recreational areas. The present disclosure also includes methods for using the pesticidal formulations comprising compounds of Formula I, or an acceptable salt, solvate, or hydrate thereof, to treat and control fungal diseases or disorders in agriculture. In some aspects, the acceptable fungicidal salt of Formula I is the hydrochloride salt (Formula LB). In some aspects, the fungal pathogens or diseases are in croplands, orchards, lawns, pastures, gardens, and recreational areas. In some aspects, the fungal pathogens or diseases are in row crops. In some aspects, the fungal pathogens or diseases are in cereals. In some aspects, the fungal pathogens or diseases are in broadleaf crops. In some aspects, the fungal pathogens or diseases are in fruits. In some aspects, the fungal pathogens or diseases are in vegetables. In some aspects, the fungal pathogens or diseases are in nuts. In some aspects, the fungal pathogens or disease are in specialty crops. In some aspects, the fungalpathogens or diseases are in sugar beet, strawberry, tomato, potato, avocado, almond, dragon fruit, durian; banana, citrus, coffee, grape, peppers (for example, bell peppers and chili peppers), pome and stone fruit (for example, apple, cherry, pear, nashi, quince, plum, nectarine, mango, and peach), pulse crops (for example, pea, lentil, faba beans, peanuts, mung beans, and common beans), leafy vegetables (for example, lettuce, mustard, onion, oregano, spinach), cole crops (for example, cabbage, broccoli, cauliflower, and kale), oilseed rape, sunflowers, sorghum, cotton, sugar cane, cucurbits (for example, pumpkin, cucumber, melon, squash, and watermelon), turfgrasses, ornamental crops (for example, rose, chrysanthemum, tulips), and bulbs.I. Definitions
[0025] Terms used herein will have their customary meaning in the art unless specified otherwise. The use of the terms “a”, “an”, “the”, “at least one” and similar referents in the context of describing the invention (especially in the context of the following claims) are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. The use of the term “at least one” followed by a list of one or more items (for example, “at least one of A and B”) is to be construed to mean one item selected from the listed items (A or B) or any combination of two or more of the listed items (A and B), unless otherwise indicated herein or clearly contradicted by context. To the extent that the term "or" is employed (e.g., A or B) it is intended to mean "A or B or both." If this disclosure intends to indicate "only A or B but not both" then the term "only A or B but not both" will be employed. Thus, use of the term "or" herein is the inclusive and not the exclusive use. The term "about" when referring to a number or a numerical range means that the number or numerical range referred to is an approximation within experimental variability (or within statistical experimental error), and thus the number or numerical range, in some instances, will vary between 1% and 15% of the stated number or numerical range. The terms “comprising,” “having,” “including,” and “containing” are to be construed as open-ended terms (i.e., meaning “including, but not limited to,”) unless otherwise noted. Recitation of ranges of values herein are merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and all examples, or exemplary language (e.g., “such as”) provided herein, is intended merely to better illuminatethe invention and does not pose a limitation on the scope of the invention unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention.
[0026] The chemical moieties mentioned when defining variable positions within the general formulae described herein (e.g. , the term “alkyl”) are collective terms for the individual substituents encompassed by the chemical moiety. The prefix Cn-Cm preceding a group or moiety indicates, in each case, the possible number of carbon atoms in the group or moiety that follows.
[0027] As used herein, the terms “pesticide” and “pesticidal active ingredient” refer to an active ingredient that controls or decreases the fitness (e.g., kills or inhibits the growth, proliferation, division, reproduction, or spread) of an agricultural, environmental, or domestic / household pest, such as an undesirable vegetation, insect, mollusk, nematode, fungus, bacterium, or vims. Pesticides are understood to encompass naturally occurring or synthetic herbicides, fungicides, insecticides, insect growth regulators, acaricides (miticides), molluscicides, nematicides, ectoparasiticides, or bactericides. The terms “pesticide” and “pesticidal active ingredient” as used herein include fungicides and fungicidal active ingredients.
[0028] As used herein, the terms “fungicide,” “fungicidal chemical,” and “fungicidal active ingredient” may be understood to include an active ingredient that kills, controls, or otherwise adversely modifies the growth of agriculturally relevant fungi, when applied in an appropriate amount.
[0029] As used herein, the term “pesticidal formulation” may be understood to include compositions that comprise at least one pesticide and at least one additional component. A pesticidal formulation is understood to include a “fungicidal formulation”.
[0030] As used herein, the terms “fungicidal formulation” or “formulation” may be understood to include compositions that comprise at least one fungicide and at least one additional component. The additional component may be a solvent, a diluent, a carrier, an adjuvant, a surfactant, a dispersant, a chemical stabilizer, a physical stabilizer, an anti-foam agent, an emulsifier, an antifreeze agent, a dye or colorant, or other such component. The additional component may be another fungicide or another agricultural chemical, such as a herbicide, an insecticide, a fungicide, a fertilizer, a nematocide, a miticide, an arthropodicide,a bactericide, a plant growth regulator, or combinations thereof that are compatible with the formulations of the present disclosure.
[0031] As used herein, the term “tank mix” may be understood to refer to a fungicidal mixture prepared from the formulation disclosed herein by the end user, by diluting the formulation, adding other ingredients and additives, mixing the formulation ingredients, or other such activities before application. The end user may then apply the tank mix, as-is or with other additives, to the seed, the area adjacent to the plant, soil adapted to support growth of the plant, the root of the plant, and / or foliage of the plant.
[0032] As used herein, the term “adjuvant” may be understood to include additives to the formulation or tank mix that, while having no fungicidal effect in themselves, help to stabilize, improve, or otherwise enhance the fungicidal effect of the fungicidal active ingredient. For example, adjuvants may be surfactants that enhance the absorption of the fungicidal active ingredient into the plant. Adjuvants may be added to the formulation, or adjuvants may be added to the fungicidal tank mix by the end user prior to application of the tank mix. Adjuvants may also be included in the fungicidal formulation, in which case the adjuvant may be referred to as a “built-in adjuvant.”
[0033] As used herein, the term "applying" a fungicide or fungicidal formulation refers to delivering the fungicide or fungicidal formulation directly to the seed, the area adjacent to the plant, soil adapted to support growth of the plant, the root of the plant, and / or foliage of the plant, where control of fungal pathogens or diseases is desired.
[0034] As used herein, the term “vegetation” can include, for instance, dormant seeds, germinating seeds, emerging seedlings, plants propagating from vegetative propagules, immature vegetation, and established vegetation.
[0035] As used herein, the term "crop" refers to desired vegetation, for instance, plants that are grown to provide food, shelter, pasture, erosion control, etc. Example crops include row crops, maize, soy, canola, cotton, pulses, sunflower, sugar beet, wheat, barley, rice, sorghum, millet, oats, flax, cereals, legumes, vegetables, orchard and timber trees, grapevines, etc. Preferably, fungicides or fungicidal compositions have zero or minimal negative effect on crops.
[0036] As used herein, the terms "active ingredient" or "ai" may be understood to include a chemical compound or composition that has an effect on fungal pathogens or diseases. The term “active ingredient” or “ai” may also be used in expressions relating concentrations orapplications rates, such as “grams active ingredient per hectare” or “g ai / ha” to clarify that the amount of the ingredient is measured as the compound as-is, including salts, esters, N-oxides, solvates, hydrates, etc.
[0037] As used herein, "acid equivalent" or "ae" may be understood to include the amount of the acid form of an active ingredient that is calculated from the amount of a salt, ester, N- oxide, solvates, or hydrate form of that active ingredient. For example, if the acid form of an active ingredient "Z " has a molecular weight of 100 Dalton, and the salt form of Z has a molecular weight of 130 Dalton, an application of 130 g ai / ha of the Z salt would be equal to applying 100 g ae / ha of the acid form of Z :130 g ai / ha Z salt * (100 Da Z acid / 130 Da Z salt) = 100 g ae / ha Z acid.The term “acid equivalent” or “ae” may also be used in expressions relating concentrations or applications rates, such as “grams acid equivalent per hectare” or “g ae / ha” to clarify that the amount of the ingredient is measured as the acid form of the compound, corrected to eliminate the mass contribution of associated salts, esters, N-oxides, solvates, hydrates, etc.
[0038] As used herein, “organic liquid” or “organic solvent” may be understood to refer to organic compounds (that is, compounds comprising carbon atoms) that are liquid at most or all typical ambient outdoor temperatures, such as from about -10 °C to 55 °C, about 0 °C to 40 °C, about 5 °C to about 50 °C, or about 8 °C to 38 °C. Organic liquids are frequently, although not always, hydrophobic and immiscible in water or aqueous liquids. It should be understood that the term “organic solvent” does not necessarily imply that any material mixed into the organic solvent dissolves in the organic solvent.
[0039] As used herein, “agriculturally acceptable salts, esters, N-oxides, solvates, and hydrates” may be understood to include salts, esters, N-oxides, solvates, and hydrates that exhibit fungicidal activity, or that are or can be converted in plants, water, or soil to the referenced fungicide.
[0040] As used herein, the terms “formulation” or “composition” refer to a mixture comprising at least one fungicide, and also comprising other ingredients used to enhance the properties or effectiveness of the mixture in some way. The other ingredients may include, but are not limited to, diluents, surfactants, adjuvants, anti-foam agents, emulsifiers, colorants, dispersants, antifreeze agents, and other such ingredients.
[0041] As used herein, the term “locus”, refers to the area in which the vegetation or plants are growing or will grow, typically a field.
[0042] As used herein, unless otherwise specified, “acyl” refers to formyl, C1-C3 alkylcarbonyl, and C1-C3 haloalkylcarbonyl. Ci-Ce acyl refers to formyl, C1-C5 alkylcarbonyl, and C1-C5 haloalkylcarbonyl (the acyl group contains a total of 1 to 6 carbon atoms).
[0043] As used herein, “alkyl” refers to saturated, straight-chained or branched saturated hydrocarbon moieties. Unless otherwise specified, C1-C16 alkyl groups are intended. Examples include methyl, ethyl, propyl, 1-methyl-ethyl, butyl, 1-methyl-propyl, 2-methyl-propyl, 1,1- dimethyl-ethyl, pentyl, 1-methyl-butyl, 2-methyl-butyl, 3-methyl-butyl, 2,2-dimethyl-propyl,1-ethyl-propyl, hexyl, 1,1-dimethyl-propyl, 1,2-dimethyl-propyl, 1-methyl-pentyl, 2-methyl- pentyl, 3-methyl-pentyl, 4-methyl-pentyl, 1,1-dimethyl-butyl, 1,2-dimethyl-butyl, 1,3- dimethyl-butyl, 2,2-dimethyl-butyl, 2,3-dimethyl-butyl, 3,3-dimethyl-butyl, 1 -ethyl -butyl, 2- ethyl-butyl, 1,1,2-trimethyl-propyl, 1,2,2-trimethyl-propyl, 1 -ethyl- 1-methyl-propyl, and 1- ethyl-2-methyl-propyl.
[0044] As used herein, “haloalkyl” refers to straight-chained or branched alkyl groups, where in these groups the hydrogen atoms may be substituted partially or entirely with halogen atoms. Unless otherwise specified, C1-C16 groups are intended. Examples include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, di chlorofluoromethyl, chlorodifluoromethyl, 1- chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2- trichloroethyl, pentafluoroethyl, and l,l,l-trifluoroprop-2-yl.
[0045] As used herein, “alkenyl” refers to unsaturated, straight-chained, or branched hydrocarbon moieties containing a double bond. Unless otherwise specified, C3-C16 alkenyl are intended. Alkenyl groups may contain more than one unsaturated bond. Examples include ethenyl, 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl- 1 -propenyl, 2-methyl-l -propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2- pentenyl, 3 -pentenyl, 4-pentenyl, 1 -methyl- 1-butenyl, 2-methyl- 1-butenyl, 3 -methyl- 1- butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3 -butenyl, 2- methyl-3-butenyl, 3-methyl-3-butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-l -propenyl, l,2-dimethyl-2-propenyl, 1 -ethyl- 1 -propenyl, l-ethyl-2-propenyl, 1 -hexenyl, 2-hexenyl, 3- hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl- 1 -pentenyl, 2-methyl- 1 -pentenyl, 3 -methyl- 1- pentenyl, 4-methyl-l -pentenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2- pentenyl, 4-methyl-2-pentenyl, l-methyl-3 -pentenyl, 2-methyl-3 -pentenyl, 3-methyl-3- pentenyl, 4-methyl-3 -pentenyl, 1 -methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, l,l-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, l,2-dimethyl-2-butenyl, l,2-dimethyl-3-butenyl, 1,3 -dimethyl- 1-butenyl, 1,3- dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3 -dimethyl- 1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2- butenyl, 1 -ethyl- 1-butenyl, l-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl- 1-butenyl, 2-ethyl-2- butenyl, 2-ethyl-3-butenyl, l,l,2-trimethyl-2-propenyl, 1 -ethyl- l-methyl-2-propenyl, 1-ethyl-2-methyl-l -propenyl, and l-ethyl-2-methyl-2-propenyl. Vinyl refers to a group having the strutcture -CH=CH2; 1 -propenyl refers to a group with the structure-CH=CH-CH3; and 2- propenyl refers to a group with the structure -CH2-CH=CH2.
[0046] As used herein, “alkynyl” represents straight-chained or branched hydrocarbon moieties containing a triple bond. Unless otherwise specified, C3-C16 alkynyl groups are intended. Alkynyl groups may contain more than one unsaturated bond. Examples include C2- Ce-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3- butynyl, l-methyl-2-propynyl, 1 -pentynyl, 2-pentynyl, 3 -pentynyl, 4-pentynyl, 3 -methyl- 1- butynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, l,l-dimethyl-2- propynyl, l-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3- m ethyl- 1 -pentynyl, 4-methyl-l -pentynyl, l-methyl-2-pentynyl, 4-methyl-2-pentynyl, 1- methyl-3 -pentynyl, 2-methyl-3 -pentynyl, l-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3- methyl-4-pentynyl, l,l-dimethyl-2-butynyl, l,l-dimethyl-3-butynyl, l,2-dimethyl-3-butynyl,2.2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, l-ethyl-2-butynyl, l-ethyl-3-butynyl, 2- ethyl-3-butynyl, and 1 -ethyl- l-methyl-2-propynyl.
[0047] As used herein, “alkoxy” refers to a group of the formula R-O-, where R is alkyl as defined above. Unless otherwise specified, alkoxy groups wherein R is a C1-C10 alkyl group are intended. Examples include methoxy, ethoxy, propoxy, 1 -methyl-ethoxy, butoxy, 1- methyl-propoxy, 2-methyl-propoxy, 1,1 -dimethyl-ethoxy, pentoxy, 1-methyl-butyloxy, 2- methyl-butoxy, 3-methyl-butoxy, 2,2-dimethyl-propoxy, 1-ethyl-propoxy, hexoxy, 1,1- dimethyl-propoxy, 1,2-dimethyl-propoxy, 1-methyl-pentoxy, 2-methyl-pentoxy, 3-methyl- pentoxy, 4-methyl-pentoxy, 1,1-dimethyl-butoxy, 1,2-dimethyl-butoxy, 1,3-dimethyl-butoxy,2.2-dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-dimethyl-butoxy, 1-ethyl-butoxy, 2-ethyl- butoxy, 1,1,2-trimethyl-propoxy, 1,2,2-trimethyl-propoxy, 1 -ethyl- 1-methyl-propoxy, and 1- ethyl-2-methyl-propoxy.
[0048] As used herein, “haloalkoxy” refers to a group of the formula R-O-, where R is haloalkyl as defined above. Unless otherwise specified, haloalkoxy groups wherein R is a Ci-Cio alkyl group are intended. Examples include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, di chlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1- bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2- chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy, pentafluoroethoxy, and l,l,l-trifluoroprop-2-oxy.
[0049] As used herein, “alkylthio” refers to a group of the formula R-S- where R is alkyl as defined above. Unless otherwise specified, alkylthio groups wherein R is a Ci-Cio alkyl group are intended. Examples include methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1-methyl-propylthio, 2-m ethylpropylthio, 1,1 -dimethylethylthio, pentylthio, 1- methylbutylthio, 2-m ethylbutylthio, 3 -methylbutylthio, 2,2-dimethylpropylthio, 1- ethylpropylthio, hexylthio, 1,1 -dimethylpropylthio, 1,2-dimethylpropylthio, 1- methylpentylthio, 2-methylpentylthio, 3 -methylpentylthio, 4-methylpentylthio, 1,1- dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3- dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2- trimethylpropylthio, 1,2,2-trimethylpropylthio, 1 -ethyl- 1 -methylpropylthio, and l-ethyl-2- methylpropylthio.
[0050] As used herein, “haloalkylthio” refers to an alkylthio group as defined above wherein the carbon atoms are substituted partially or entirely with halogen atoms. Unless otherwise specified, haloalkylthio groups wherein R is a Ci-Cs alkyl group are intended. Examples include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1- chloroethylthio, 1 -bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2- dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio, and 1,1,1- trifluoroprop-2-ylthio.
[0051] As used herein, “aryl”, as well as derivative terms such as aryloxy, refers to a phenyl, indanyl or naphthyl group with phenyl being preferred. The term heteroaryl, as well as derivative terms such as heteroaryloxy, refers to a 5- or 6-membered aromatic ring containing one or more heteroatoms, viz., N, O or S; these aromatic and heteroaromatic rings may be fused to other aromatic and / or heteroaromatic systems. The aryl or heteroaryl substituents may be unsubstituted or substituted with one or more substituents selected from halogen, hydroxy,nitro, cyano, formyl, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, Ci-Ce alkoxy, Ci-Ce haloalkyl, Ci-Ce haloalkoxy, Ci-Ce acyl, Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce alkoxycarbonyl, Ci-Ce carbamoyl, hydroxycarbonyl, Ci-Ce alkylcarbonyl, aminocarbonyl, Ci- Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied.
[0052] As used herein, “alkylcarbonyl” refers to an alkyl group bonded to a carbonyl group. C1-C3 alkylcarbonyl and C1-C3 haloalkylcarbonyl refer to groups wherein a C1-C3 alkyl group is bonded to a carbonyl group (the group contains a total of 2 to 4 carbon atoms).0
[0053] As used herein, “alkoxycarbonyl” refers to a group of the formulawherein R is alkyl.
[0054] As used herein, “arylalkyl” refers to an alkyl group substituted with an aryl group. For example, “C7-C10 arylalkyl” refers to a group wherein the total number of carbon atoms in the group is 7 to 10.
[0055] As used herein, “alkylamino” refers to an amino group substituted with one or two alkyl groups, which may be the same or different.
[0056] As used herein, “haloalkylamino” refers to an alkylamino group wherein the alkyl carbon atoms are substituted partially or entirely with halogen atoms.
[0057] As used herein, “Ci-Ce alkylaminocarbonyl” refers to a group of the formula RNHC(O)- wherein R is Ci-Ce alkyl, and Ci-Ce dialkylaminocarbonyl refers to a group of the formula R2NC(O)- wherein each R is independently Ci-Ce alkyl.
[0058] As used herein, “alkylcarbamyl” refers to a carbamyl group substituted on the nitrogen with an alkyl group.O11— S-RII
[0059] As used herein, “alkyl-sulfonyl” refers to a group of the formula O , where R is alkyl.
[0060] As used herein, “carbamyl” (also referred to as carbamoyl and aminocarbonyl) o refers to a group of the formulaII — P-OR
[0061] As used herein, “dialkylphosphonyl” refers to a group of the formula OR where R is independently alkyl in each occurrence.
[0062] As used herein, “Ci-Ce trialkyl silyl” refers to a group of the formula -SiRa wherein each R is independently a Ci-Ce alkyl group (the group contains a total of 3 to 18 carbon atoms).
[0063] As used herein, “Me” refers to a methyl group; “OMe” refers to a methoxy group; and “i-Pr” refers to an isopropyl group.
[0064] As used herein, the term “halogen” including derivative terms such as halo refers to fluorine, chlorine, bromine and iodine.II. Aryl Amidines Pesticides
[0065] Formulations and methods of the present disclosure include pesticidal formulations comprising a compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, to control fungal pathogens and diseases in various locations, such as croplands, orchards, lawns, pastures, gardens, and recreational areas. Also disclosed herein are pesticidal formulations comprising a compound of Formula I-B to control fungal pathogens and diseases in various locations, such as croplands, orchards, lawns, pastures, gardens, and recreational areas.
[0066] In some aspects of the disclosure herein provide fungicidal formulations comprising a fungicidal compound of the Formula I:Formula I or an acceptable salt, solvate, or hydrate thereof.
[0067] In some aspects of the disclosure herein provide fungicidal formulations comprising an acceptable fungicidal salt of a compound of Formula I, where the acceptable fungicidal salts of Formula I include but not limited to hydrochloride, hydrobromide, sulfate, phosphate, trifluoroacetate, formate, citrate, maleate, oxalate, tartrate, fumarate, or combinations thereof.
[0068] In some aspects of the disclosure herein provide fungicidal formulations comprising an acceptable fungicidal salt of a compound of Formula I, where the acceptable fungicidal salts of Formula I is the hydrochloride salt (Formula I-B):Formula I-BIII. Formulations
[0069] The present disclosure includes pesticidal formulations of compounds of Formula I, or an acceptable salt, solvate, or hydrate thereof, and methods of use of the pesticidal formulation disclosed herein to control fungal pathogens and diseases.A. Physical States
[0070] In some aspects, the pesticidal formulation of compounds of Formula I, or an acceptable salt, solvate, or hydrate thereof, may be present in suspended, emulsified, dissolved, or solid form. Exemplary formulations include, but are not limited to, soluble liquid concentrates, aqueous suspension concentrates, oil-in-water emulsions, oil-in-water microemulsions, aqueous suspo-emulsions, water-in-oil emulsion, water-in-oil microemulsions, oil suspensions, emulsifiable concentrates, self-emulsifying formulations, pastes, gels, powders, dusts, granules, water-dispersible granules, wettable granules, wettable powders, and materials for spreading. A comprehensive list of formulation types with official definitions is available from CropLife International (croplife.org / wp- content / uploads / 2017 / 04 / Technical-Monograph-2-7th-Edition-Revised-March-2017.pdf).
[0071] In some aspects, the pesticidal formulation is a liquid formulation that can be diluted before use. Exemplary liquid formulations include, but are not limited to, soluble liquid concentrates, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, microemulsions, suspension concentrates, capsule suspensions, suspo-emulsions, oil dispersions. The liquid formulation may be diluted with a carrier such as water by the end user, and then applied by the end user as needed.
[0072] Soluble liquid concentrates are liquid, homogenous formulations in water or one or more water miscible solvent or their mixtures that become homogenous solution when diluted with water or a liquid by the end user. Emulsifiable concentrates are liquid, homogeneous formulations in hydrophobic organic liquids that become oil-in-water emulsions when diluted with water or an aqueous liquid by the end user. Emulsions are two-phase (or more phases) liquid mixtures containing two or more immiscible liquid phases, with fine droplets of oneimmiscible liquid dispersed in a continuous phase of the other immiscible liquid. The diluted emulsion is then applied by the end user as needed. Oil-in-water emulsions are liquid, heterogeneous formulations containing an organic liquid dispersed as fine droplets in a continuous water or aqueous liquid phase. In one aspect, the fungicide may be dissolved or dispersed in the organic liquid droplets dispersed in an oil-in-water emulsion. In another aspect, the fungicide may be dissolved or dispersed in the continuous water or aqueous liquid phase of an oil-in-water emulsion. Water-in-oil emulsions are liquid, heterogeneous formulations containing water or an aqueous liquid dispersed as fine droplets in a continuous hydrophobic organic liquid phase. In one aspect, the fungicide may be dissolved or dispersed in the water or aqueous liquid droplets dispersed in a water-in-oil emulsion. In another aspect, the fungicide may be dissolved or dispersed in the continuous organic liquid phase of a water- in-oil emulsion. Multi-phase emulsions, such as water-in-oil-in-water emulsions, are also known. The size of the dispersed droplets in these emulsions (also called “conventional emulsions”) is typically in the range of about 0.1 to 100 pm in diameter. A microemulsion is a clear to opalescent liquid containing both organic liquid and water or an aqueous liquid. The microemulsion may be oil-in-water or water-in-oil emulsions, where the dispersed globules are very small, typically less than 1 pm or less than 0.1 pm. Microemulsions differ from conventional emulsions in that: a) the droplet size in microemulsions is smaller; b) microemulsions are typically clear or opalescent, whereas conventional emulsions are cloudy or milky; and c) microemulsions are thermodynamically stable and remain dispersed, whereas conventional emulsions are kinetically stable but thermodynamically unstable, and typically require mixing energy, such as high-shear mixing, to maintain the emulsion droplets dispersed within the continuous liquid phase.
[0073] Formulations comprising the fungicidal compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, may be emulsifiable concentrates, where the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, is dissolved in one or more organic liquid(s) or solvent(s). The emulsifiable concentrate forms an oil-in-water emulsion when diluted with water before use. The emulsifiable concentrate formulation may also include one or more emulsifiers, and optionally, one or more of co-solvent(s), built-in adjuvant(s), antifoam agent(s), or other components.
[0074] Suitable organic solvents for forming emulsifiable concentrates of the compound ofFormula I, or an acceptable salt, solvate, or hydrate thereof, include, but are not limited to: long-chain alkyl amides, such as N,N-dimethylalkyl amide, Agnique® AMD 810 or AgniqueAMD 10 (Agnique® is a registered trademark of BASF Corporation, Florham Park, NJ, USA), Hallcomid® M-10 or Hallcomid® M-8-10 or Hallcomid® M8-10 Ultra or Hallcomid® 1025 or Hallcomid-M-12-14 or Hallocmid-M-12 (Hallcomid® is a registered trademark of Stepan Company, Northfield, Illinois, USA), Genagen PA or Genagen® 4166 (Genagen® is a registered trademark of Clariant Produkte (Deutschland) GmbH, Frankfurt am Main, Germany) or Armid® DM810 (Armid® is a registered trademark of Noury on, Amsterdam, Netherlands); methylated seed oils, such as Agnique® 610 U, Agnique® MEI 8 RD-F, Agnique® MEI 8 S- U, Agnique® ME 2337 , or Agnique® ME 1218; fatty acid or triglyceride esters, such as Steposol® ME, Steposol® C-48, Stepan® C-25, Stepan® 108 (Steposol® and Stepan® are registered trademarks of Stepan Company, Northfield, Illinois, USA); fatty acid morpholine amide, such as Jeffsol® AG 1730 (Jeffsol® is a registered trademark of Huntsman Petrochemical Corporation, Salt Lake City, Utah, USA); ketones such as 2-heptanone, cyclopentanone, acetophenone, or Cyrene® (Cyrene® is a registered trademark of Circa Group Pty Ltd, Coburg, Victoria, Australia); or phosphate triesters, such as DisflamollTOF (Disflamoll® is a registered trademark of Lanxess Corporation, Pittsburgh, PA, USA), or Amgard® TBEP (Amgard® is a trademark of Syensqo S.A., Brussels, Belgium); aromatic solvents, such as Aromatic 100, Aromatic 150, Aromatic 150 ND, Aromatic 200, or Aromatic 200 ND (Aromatic solvents are available from ExxonMobil Chemical Company, Spring, TX, USA), or Solvesso™ 100, or Solvesso™ 150, Solvesso™ 150ND, Solvesso™ 200, Solvesso™ 200ND (Solvesso™ is a trademark of ExxonMobil Chemical Company, Spring, TX, USA); or aliphatic / paraffinic oils, such as Isopar® M, Isopar N, or Exxsol® D130 (Isopar®, and Exxsol® are trademarks of ExxonMobil Corporation, Irving, Texas, USA); or alkyl alcohol, such as 2-ethylhexanol; alkyl benzoate or dibenzoate, such as Surfonic® AG 1700 (Surfonic® is a trademark of Indorama, The Woodlands, TX, USA) or Zendex® DB-120 (Zendex® is a trademark of Eastman Chemical Company, Kingsport, TN, USA); alkyl lactates, such as Agnique® AE 3-2EH, or Purasolv® EHL (Purasolv® is a registered trademark of Purac Biochem B.V., Gorinchem, Netherlands); ester solvents, such as Rhodiasolv® RPDE (Rhodiasolv® is a trademark of Syensqo S. A., Brussels, Belgium), or benzyl acetate, or triethyl citrate, or Isobornyl acetate, or ethyl 5-methyl-2-furoate; p-anisaldehyde. Suitable co-solvents for the emulsifiable concentrates of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, s include, but are not limited to: alkyl pyrrolidone, such as Genagen NBP and Tamisolve® NxG (Tamisolve is a registered trademark of Eastman Chemical Company, Kingsport, TN, USA), l-dodecyl-2-pyrrolidone, or N-octyl-2-pyrrolidione; ether solvents, such as Atlox® Solvall™ BDE l-LQ-(AP) (Atlox® and Solvall™ are trademarks of CrodaInc., Edison, NJ, USA); aprotic glycol ethers, such as Dowanol DPM, or butyl Cellosolve™ solvent, or Carbitol™ solvent, or Proglyde® DMM (Dowanol, Cellosolve™, Carbitol™ and Proglyde® are registered trademarks of Dow Chemical Company, Midland, Michigan, USA); glycol ether acetate, such as Dowanol® PMA; alkanol solvent, such as hexylene glycol; N,N- dimethyl lactamide, such as Agnique® AMD 3L; alkylene carbonates, such as Jeffsol® AG 1505 or Jeffsol® AG 1555; alkyl lactates, such as Purasolv® EL; lactone solvent, such as y- butyrolactone, y-caprolactone, d-valerolactone; cyclohexanone; or diamides and ester amides, such as Rhodiasolv® PolarClean; Augeo® SL191 (Augeo® is a trademark of Syensqo S.A., Brussels, Belgium); ester solvent, such as UCAR™ Filmer IBT (UCAR™ is a trademark of the Dow Chemical Company, Midland, MI, USA); N-formylmorpholine; or benzyl alcohol.
[0075] Suitable emulsifiers include, but are not limited to, non-ionic, anionic, and polymeric emulsifiers. Suitable non-ionic emulsifiers include: ethoxylated castor oil, such as Agnique® CSO-25, Toximul® 8240 (Toximul® is a registered trademark of Stepan Company, Northfield, Illinois, USA), or Etocas™ 29 (Etocas™ is a trademark of Croda International Pic, Goole, East Yorkshire, UK); or ethoxylated fatty alcohols / fatty acids, such as, Makon® DA-6 (Makon® is a registered trademark of Stepan Company, Northfield, Illinois, USA), Synperonic® 13 / 12 (Synperonic® is a registered trademark of Croda International Pic, Goole, East Yorkshire, UK), Ecosurf™ SA-4 (Ecosurf™ is a registered trademark of Dow Chemical Company, Midland, Michigan, USA), or Tergitol 15-S-12 (Tergitol® is a registered trademark of Union Carbide Corporation, Midland, Michigan, USA); or alkoxylated fatty alcohols, such as Dehypon® LS 54 (Dehypon® is a registered trademark of BASF Corporation, Mount Olive, New Jersey, USA), Genapol® EP 2552 (Genapol® is a registered trademark of Clariant); or sorbitan ester ethoxylate / alkoxylate, such as Tween® 80 (Tween® is a registered trademark of Croda International Pic, Goole, East Yorkshire, UK); or sorbitan esters, such as Span® 80 (Span® is a registered trademark of Uniqema Americas LLC, Wilmington, Delaware, USA); or polyglycerol ester, such as Break-thru® SP 133 (Break-thru® is a registered trademark of Evonik Operations GmbH, Essen, Germany); or Trisiloxane / Polysiloxane, such as Break- thru® OE 446, Break-thru® S 233, Break-thru® S 240, or Silwet®-L77 (Silwet® is a registered trademark of Momentive). Suitable polymeric emulsifiers include: EO / PO block copolymers, such as Toximul® 8320, Termul® 5500 (Termul® is a registered trademark of Indorama Ventures Oxides LLC, The Woodlands, Texas, USA), Ethylan™ NS-500LQ (Ethylan™ is a trademark of Nouryon Surface Chemistry LLC, Chicago, Illinois, USA), Tergitol® XD (Tergitol® is a registered trademark of Union Carbide Corporation, Midland,Michigan, USA), Pluronic® P-105 (Pluronic® is a registered trademark of BASF Corporation, Mount Olive, New Jersey, USA), or Atlas® G-5002L (Atlas® is a registered trademark of Croda International Pic, Goole, East Yorkshire, UK); or other polymeric surfactants, such as Atlox® 4912 or Atlox® 4914. Suitable anionic emulsifiers include: various salts of dodecylbenzene sulfonates, such as Bio-Soft® N-411 (Bio-Soft® is a registered trademark of Stepan Company, Northfield, Illinois, USA), Nansa® EVM 70 / 2E (Nansa® is a trademark of Innospec Performance Chemicals Europe Ltd, Cheshire, UK); or sodium dioctyl sulfosuccinates, such as Geropon® SDS (Geropon® is a registered trademark of Rhodia Chimie SAS, Aubervilliers, France), Lankropol™ KPH 70 (Lankropol™ is a trademark of Noury on Surface Chemistry LLC, Chicago, Illinois, USA) , or Aerosol OT (Aerosol OT is available from Syensqo S.A., Brussels, Belgium); or sodium lauryl sulfonates, such as Stepanol® ME Dry (Stepanol® is a registered trademark of Stepan Company, Northfield, Illinois, USA); or phosphate ester, such as STEPFAC™ 8180 (STEPFAC™ is a registered trademark of Stepan Company, Northfield, Illinois, USA), or Rhodafac® RS 610 (Rhodafac® is a registered trademark of Syensqo S.A., Brussels, Belgium). Some emulsifiers can be multifunctional. For example, some Trisiloxane / Polysiloxane, such as Break-thru® OE 446, Break-thru® S 233, and Break-thru® S 240, are also recognized adjuvants.
[0076] Suitable antifoam agents include polydimethylsiloxanes emulsified in water, such as Foamaster® UDB (Foamaster® is a registered trademark of BASF Corporation, Florham Park, NJ, USA), or SAG™ 1572, or SAG™ 1538, or SAG™ 1599 (SAG™ is a trademark of Momentive Performance materials, Friendly, WV, USA), or Xiameter™ ACP-0001, or Xiameter™ ACP-0100, or Xiameter™ ACP-1400, or Xiameter™ AFE-0010, or Xiameter™ AFE-0300 (Xiameter™ is a trademark of the Dow Chemical Company, Midland, MI, US), or Antifoam 10, or Antifoam 100, or Antifoam 8810 IND, or Antifoam 8830 IND, or Silfar® S 184; or Silfar® SE 4; or Silfoam® SC 132, or Silfoam® SE-23 (Silfar® and Silfoam® are trademarks of Wacker Silicones, Adrian, MI, USA); or Break-thru® AF 9902, or Break-thru® AF 9903, or Break-thru® AF 9905.
[0077] Suitable built-in adjuvants can be any of the agriculturally acceptable adjuvants disclosed herein above. Exemplary built-in adjuvants include: methylated seed oils, including Cl 8 soyate and Cl 8 rapeate, such as Agnique® ME 18 RD-F, Agnique® ME 18 SD-F, Agnique® ME 2337, or Edenor® ME 12-18; non-ionic surfactants, including ethoxylated castor oils such as Agnique® CSO-25, Etocas™ 10, Etocas™ 29, or Etocas™ 40; C16-C18 alcohol ethoxylate propoxylate ether, such as PLURAFAC LF 1300 manufactured and sold byBASF (previously sold under the name Agnique® BP-420); ethoxylated fatty alcohols, such as Synperonic® 13 / 12; polysorbates, such as Tween® 80 (Tween® is a registered trademark of Croda International Pic, Goole, East Yorkshire, UK); sorbitan esters, such as Span® 80 (Span® is a registered trademark of Uniqema Americas LLC, Wilmington, Delaware, USA); and phosphates, such as tris(2-ethylhexyl) phosphate (TEHP).
[0078] Formulations comprising the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, of the present disclosure may be oil-in-water emulsions, where the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, is dissolved in the dispersed droplets of the organic liquid phase. The emulsion formation may contain: the organic liquid; an emulsifier; and water, aqueous liquid, or other diluent. Suitable organic liquids and emulsifiers may be chosen from the solvents, co-solvents, and emulsifiers listed for emulsifiable concentrates. The oil-in-water emulsion formulation may also contain one or more of antimicrobial agent(s), viscosity modifier(s), antifreeze(s), pH modifier(s), antifoam agent(s), or built-in adjuvant(s). Suitable antimicrobial agents include: 1,2-benzisothiazolin- 3-one, such as Proxel® GXL (Proxel® is a registered trademark of Arch UK Biocides Ltd, Castleford, West Yorkshire, UK); 5-chloro-2-methyl-4-isothiazolin-3-one; or 2-methyl4- isothiazolin-3-one, such as Kathon® CG / ICP (Kathon® is a registered trademark of Rohm and Haas Company, Philadelphia, Pennsylvania, USA). Suitable viscosity modifiers include: smectite clay, such as Veegum® (Veegum® is a registered trademark of Vanderbilt Minerals LLC, Norwalk, Connecticut, USA); microcrystalline cellulose, such as Avicel® CL-611 (Avicel® is a registered trademark of DuPont Nutrition USA, Wilmington, Delaware, USA); xantham gum, such as Rhodopol® 23, Rhodopol® Extra 2, or Rhodicare® CFT (Rhodopol® and Rhodicare® are registered trademarks of Rhodia Chimie Corporation, Aubervilliers, France); or diutan gum. Suitable antifreeze compounds include: propylene glycol; glycerol; or electrolyte-based antifreeze, such as sodium chloride or sodium acetate. Suitable pH modifiers include agriculturally-acceptable weak acidic or basic buffers, such as sodium phosphate, potassium phosphate, phosphoric acid, sodium citrate, potassium citrate, citric acid, sodium lactate, potassium lactate, or lactic acid. Suitable antifoam agents include polydimethylsiloxanes emulsified in water, such as Foamaster® UDB (Foamaster® is a registered trademark of BASF Corporation, Florham Park, NJ, USA), or SAG™ 1572, or SAG™ 1538, or SAG™ 1599 (SAG™ is a trademark of Momentive Performance materials, Friendly, WV, USA), or Xiameter™ ACP-0001, or Xiameter™ ACP-0100, or Xiameter™ ACP-1400, or Xiameter™ AFE-0010, or Xiameter™ AFE-0300 (Xiameter™ is a trademarkof the Dow Chemical Company, Midland, MI, US), or Antifoam 10, or Antifoam 100, or Antifoam 8810 IND, or Antifoam 8830 IND, or Silfar® S 184; or Silfar® SE 4; or Silfoam® SC 132, or Silfoam® SE-23 (Silfar® and Silfoam® are trademarks of Wacker Silicones, Adrian, MI, USA); or Break-thru® AF 9902, or Break-thru® AF 9903, or Break-thru® AF 9905. For diluents, water, an aqueous liquid, or a polar solvent that is not miscible with the organic phase can be selected. Suitable built-in adjuvants include: methylated seed oils, including Cl 8 soyate and C18 rapeate, such as Agnique® ME 18 RD-F, Agnique® ME 18 SD- F, Agnique® ME 2337, or Edenor® ME 12-18; ethoxylated castor oils such as Agnique® CSO-25, Etocas™ 10, Etocas™ 29, or Etocas™ 40; ethoxylated fatty alcohols, such as Synperonic® 13 / 12; polysorbates, such as Tween® 80; sorbitan esters, such as Span® 80; and phosphates, such as tris(2-ethylhexyl) phosphate.
[0079] Formulations comprising the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, of the present disclosure may be microemulsions comprising a water- immiscible organic liquid phase (e.g., an oil phase) and a water-miscible phase. The compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, may be dissolved in the oil phase or the water-miscible phase. The microemulsion formulation may contain: a water immiscible organic liquid; water, an aqueous liquid, or a water-miscible solvent; and an emulsifier. Suitable water-immiscible organic liquids and emulsifiers may be chosen from the solvents, co-solvents, and emulsifiers listed for emulsifiable concentrates. Suitable water-miscible solvents include, but are not limited to, propylene carbonates, such as Jeffsol® AG 1555. The microemulsion formulation may also contain an antimicrobial agent, a pH modifier, an antifoam agent, or a built-in adjuvant, such as these components described above for oil-in- water emulsions.
[0080] A suspension is a liquid, heterogeneous formulation containing a finely-divided solid dispersed within a continuous liquid phase. A suspension concentrate is a stable suspension of active ingredients with water or an aqueous liquid as the continuous liquid phase, intended for dilution with water by the end user before use. A capsule suspension is a stable suspension of capsules, such as microencapsulated solid or liquid fungicides or fungicidal compositions, dispersed in a continuous liquid phase, intended for dilution with water by the end user before use. An oil dispersion is a stable suspension of fungicide in a water-immiscible organic liquid phase, intended for dilution with water by the end user before use.
[0081] Formulations comprising the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, of the present disclosure may be suspension concentrates comprising astable suspension of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, suspended in a water or aqueous liquid continuous phase. The suspension concentrate may contain water, a wetting agent, a dispersant, a viscosity modifier, an antifoam agent, an antimicrobial agent, antifreeze, a pH modifier, and a built-in adjuvant. Suitable wetting agents include sodium alkyl sulfosuccinate, such as Lankropol™ KPH 70; sodium naphthalenesulfonate or its blend, such as Morwet® EFW (Morwet® is a registered trademark of Noury on Surface Chemistry LLC, Chicago, Illinois, USA); sodium lauryl sulfonates, such as Stepanol® ME Dry; EO / PO block copolymer, such as Pluronic® P-105; or alcohol ethoxylates, such as Synperonic® 13 / 12. Suitable dispersants include: condensed naphthalene formaldehydes, such as Morwet® D-425; EO / PO block copolymers, such as Pluronic® P-105; lignosulfonate, such as Kraftsperse®. REAX® (Kraftsperse® and REAX® are registered trademarks of Ingevity South Carolina LLC, North Charleston, South Carolina, USA), or Borresperse NA (Borresperse® is a registered trademark of Borregaard, Rothschild, Wisconsin, USA); sodium styrene acrylates, such as Atlox Metasperse® 500L (Atlox Metasperse® is a registered trademark of Croda International Pic, Goole, East Yorkshire, UK); acrylic copolymer sulfonates, such as Agrilan® 789 (Agrilan® is a registered trademark of Noury on, Amsterdam, Netherlands); comb polymers, such as Atlox® 4913; tristyrylpheol ethoxylate, such as Soprophor® BSU (Soprophor® is registered trademark of Syensqo S.A., Brussels, Belgium); or polymeric dispersant, such as Atlox 4915. Suitable viscosity modifiers include: smectite clay, such as Veegum®; microcrystalline cellulose, such as Avicel® CL-611; xantham gum, such as Rhodopol® 23, Rhodopol® Extra 2, or Rhodicare® CFT; or diutan gum. Suitable antifoam agents include polydimethylsiloxanes emulsified in water, such as Foamaster® UDB (Foamaster® is a registered trademark of BASF Corporation, Florham Park, NJ, USA), or SAG™ 1572, or SAG™ 1538, or SAG™ 1599 (SAG™ is a trademark of Momentive Performance materials, Friendly, WV, USA), or Xiameter™ ACP-0001, or Xiameter™ ACP-0100, or Xiameter™ ACP-1400, or Xiameter™ AFE-0010, or Xiameter™ AFE-0300 (Xiameter™ is a trademark of the Dow Chemical Company, Midland, MI, US), or Antifoam 10, or Antifoam 100, or Antifoam 8810 IND, or Antifoam 8830 IND, or Silfar® S 184; or Silfar® SE 4; or Silfoam® SC 132, or Silfoam® SE-23 (Silfar® and Silfoam® are trademarks of Wacker Silicones, Adrian, MI, USA); or Break-thru® AF 9902, or Break-thru® AF 9903, or Break-thru® AF 9905. Suitable antimicrobial agents include: 1,2- benzisothiazolin-3-one, such as Proxel® GXL; 5-chloro-2-methyl-4-isothiazolin-3-one; and 2- methyl-4-isothiazolin-3-one, such as Kathon® CG / ICP. Suitable antifreeze agents include glycols, such as propylene glycol, or glycerol, or electrolyte-based antifreeze, such as sodiumchloride, or sodium acetate. Suitable pH modifiers include agriculturally-acceptable weak acidic or basic buffers, such as sodium phosphate, potassium phosphate, phosphoric acid, sodium citrate, potassium citrate, citric acid, sodium lactate, potassium lactate, or lactic acid. Suitable built-in adjuvants include: ethoxylated castor oils, such as Agnique® CSO-25, Etocas™ 10, Etocas™ 29, or Etocas™ 40; ethoxylated fatty alcohols, such as Synperonic® 13 / 12); polysorbates, such as Tween® 80; sorbitan esters, such as Span® 80; or phosphates, such as tris(2-ethylhexyl) phosphate.
[0082] Formulations comprising the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, of the present disclosure may be capsule suspensions (CS) comprising a stable suspension of microcapsules in a water or aqueous liquid continuous phase. The compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, may be encapsulated in the microcapsules. The capsule suspension formulation may contain microcapsules, organic solvents, water or aqueous liquid, an emulsifier, a dispersant, a viscosity modifier or suspending aid, an antimicrobial agent, antifreeze, a pH modifier, and a built-in adjuvant. For the microcapsule, methylene diphenyl diisocyanate (such as PAPI 27) and a water soluble primary or secondary polyamine (such as ethylenediamine or diethylenetriamine) can be used to form the microcapsules. Suitable organic solvents include high flash-point aromatic solvents, such as Aromatic 100, Aromatic 150, Aromatic 150 ND, Aromatic 200, or Aromatic 200 ND (Aromatic solvents are available from ExxonMobil Chemical Company, Spring, TX, USA). Suitable emulsifiers include: poly(vinyl alcohol), such as Selvol® 205 (Selvol® is a registered trademark of Sekisui Specialty Chemicals America, Dallas, Texas, USA) or Gohsenol® GL3 (Gohsenol® is a registered trademark of Mitsubishi Chemical Corporation, Tokyo, Japan); alkylpolyglycosides, such as Agnique® PG 8107; alcohol ethoxylates, such as Tergitol® 15-S-7 or Tergitol® 15-S-9; EO-PO block copolymers, such as Pluronic® P-105; polymethylmethacrylate-PEG graft copolymers, such as Atlox® 4913; phosphate esters, such as Multitrope™ 1214 (Multitrope™ is a trademark of Croda International Pic, Goole, East Yorkshire, UK); sodium dioctyl sulfosuccinates such as Geropon® SDS; isopropylamine dodecylbenzene sulfonates, such as Bio-Soft® N-411; or calcium dodecylbenzene sulfonates, such as Nansa® EVM 70 / 2E. Suitable dispersants include: sodium lignosulfonate, such as Kraftsperse® 25M; sodium styrene acrylates, such as Atlox Metasperse® 500L; acrylic copolymer sulfonates, such as Agrilan® 789; comb polymers such as Atlox® 4913; or tristyrylphenol ethoxylates, such as Soprophor® FLK. Suitable viscosity modifiers or suspending aides include: smectite clay, such as Veegum®; microcrystalline cellulose, such asAvicel® CL-611; xantham gum, such as Rhodopol® 23, Rhodopol® Extra 2, or Rhodicare® CFT; or diutan gum. Suitable antifoam agents include poly dimethylsiloxanes emulsified in water, such as Foamaster® UDB (Foamaster® is a registered trademark of BASF Corporation, Florham Park, NJ, USA), or SAG™ 1572, or SAG™ 1538, or SAG™ 1599 (SAG™ is a trademark of Momentive Performance materials, Friendly, WV, USA), or Xiameter™ ACP- 0001, or Xiameter™ ACP-0100, or Xiameter™ ACP-1400, or Xiameter™ AFE-0010, or Xiameter™ AFE-0300 (Xiameter™ is a trademark of the Dow Chemical Company, Midland, MI, US), or Antifoam 10, or Antifoam 100, or Antifoam 8810 IND, or Antifoam 8830 IND, or Silfar® S 184; or Silfar® SE 4; or Silfoam® SC 132, or Silfoam® SE-23 (Silfar® and Silfoam® are trademarks of Wacker Silicones, Adrian, MI, USA); or Break-thru® AF 9902, or Break-thru® AF 9903, or Break-thru® AF 9905. Suitable antimicrobial agents include: 1,2- benzisothiazolin-3-one, such as Proxel® GXL; 5-chloro-2-methyl-4-isothiazolin-3-one; and 2- methyl-4-isothiazolin-3-one, such as Kathon® CG / ICP. Suitable antifreeze agents include glycols, such as propylene glycol, or glycerol, or electrolyte-based antifreeze, such as sodium chloride, or sodium acetate. Suitable pH modifiers include agriculturally-acceptable weak acidic or basic buffers, such as sodium phosphate, potassium phosphate, phosphoric acid, sodium citrate, potassium citrate, citric acid, sodium lactate, potassium lactate, or lactic acid. Suitable built-in adjuvants include: ethoxylated castor oils, such as Agnique® CSO-25, Etocas™ 10, Etocas™ 29, or Etocas™ 40; ethoxylated fatty alcohols, such as Synperonic® 13 / 12); polysorbates, such as Tween® 80; sorbitan esters, such as Span® 80; or phosphates, such as tris(2-ethylhexyl) phosphate.
[0083] Formulations comprising the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, of the present disclosure may be oil dispersions (OD) comprising a stable suspension of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, in an organic solvent. The compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, may be dissolved or dispersed in the organic solvent. The oil dispersion formulation may contain an organic solvent or oil, a surfactant, a thickener, antifreeze, an antifoam agent, and a built-in adjuvant. Suitable organic solvents or oils include: high flash-point aromatic solvents, such as Aromatic 100, Aromatic 150, Aromatic 150 ND, Aromatic 200, or Aromatic 200 ND; aliphatic / paraffinic oils, such as Isopar® M or Exxsol® D130; methylated seed oils, such as Agnique® ME 18 RD-F, Agnique® ME 18 SD-F, Agnique® ME 2337, or Agnique® ME 12-18; or fatty acid or triglyceride esters, such as Steposol® SC or Stepan® 108. Suitable thickeners include: rheological modifiers of hydrophobic organoclay, such as Bentone® 34(Bentone® is a registered trademark of Elementis Specialties, Inc., Hightstown, New Jersey, USA); oil-based polymers; or hydrophobic modified silica, such as Aerosil® R974 (Aerosil® is a registered trademark of Evonik Operations GmbH, Essen, Germany). Suitable surfactants include non-ionic polymeric surfactants, such as Pluronic® F-108 or Atlox® 4912. Suitable antifreeze agents include: glycols, such as propylene glycol; glycerol; or electrolyte-based antifreeze, such as sodium chloride, or sodium acetate. Suitable antifoam agents include polydimethylsiloxanes emulsified in water, such as Foamaster® UDB (Foamaster® is a registered trademark of BASF Corporation, Florham Park, NJ, USA), or SAG™ 1572, or SAG™ 1538, or SAG™ 1599 (SAG™ is a trademark of Momentive Performance materials, Friendly, WV, USA), or Xiameter™ ACP-0001, or Xiameter™ ACP-0100, or Xiameter™ ACP-1400, or Xiameter™ AFE-0010, or Xiameter™ AFE-0300 (Xiameter™ is a trademark of the Dow Chemical Company, Midland, MI, US), or Antifoam 10, or Antifoam 100, or Antifoam 8810 IND, or Antifoam 8830 IND, or Silfar® S 184; or Silfar® SE 4; or Silfoam® SC 132, or Silfoam® SE-23 (Silfar® and Silfoam® are trademarks of Wacker Silicones, Adrian, MI, USA); or Break-thru® AF 9902, or Break-thru® AF 9903, or Break-thru® AF 9905. Suitable built-in adjuvants include: methylated seed oils, such as Agnique® ME 18 RD- F, Agnique® ME 18 SD-F, Agnique® ME 2337, or Edenor® ME 12-18; ethoxylated castor oils, such as Agnique® CSO-25, Etocas™ 10, Etocas™ 29, or Etocas™ 40; ethoxylated fatty alcohols, such as Synperonic® 13 / 12); polysorbates, such as Tween® 80; sorbitan esters, such as Span® 80; or phosphates, such as tris(2-ethylhexyl) phosphate.
[0084] A suspo-emulsion is a liquid, heterogeneous formulation consisting of a stable dispersion of active ingredient(s) in the form of solid particles and of an oil-in-water emulsion in a continuous water or aqueous liquid phase.
[0085] Formulations comprising the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, of the present disclosure may be suspo-emulsions, where the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, may be dissolved in the organic solvent as part of the oil-in-water emulsion, or dispersed as solid particles. The suspo-emulsion formation may contain an organic solvent, an emulsifier, and water or other diluents. Suitable organic solvents and emulsifiers may be chosen from the solvents, co-solvents, and emulsifiers listed for emulsifiable concentrates. Other suitable organic solvents include: high flash-point aromatic solvents, such as Aromatic 100, Aromatic 150, Aromatic 150 ND, Aromatic 200, or Aromatic 200 ND; or aliphatic / paraffinic oils, such as Isopar® M or Exxsol® D130. Suitable diluents include, but are not limited to, water or propylene carbonates, such as Jeffsol® AG1555. The suspo-emulsion formulation may also contain a wetting agent, a dispersant, a viscosity modifier, an antifoam agent, an antimicrobial agent, antifreeze, a pH modifier, or a built-in adjuvant such as these components described above for suspension concentrates. Suitable wetting agents include: blend of octyl sulfosuccinate and sodium naphthalene, such as Morwet® EFW; EO / PO block polymers, such as Pluronic® P-105; alcohol ethoxylates, such as Synperonic® 13 / 12; sodium taurates, such as Geropon® T-77; or polycarboxylates, such as Geropon® T-36. Suitable dispersants include: sodium naphthalene sulfonate formaldehyde condensates, such as Morwet® D-425; EO-PO block copolymers, such as Pluronic® P-105; or comb copolymers, such as Atlox® 4913. Suitable viscosity modifiers include: smectite clays, such as Veegum®; microcrystalline cellulose, such as Avicel® CL-611; xanthum gum, such as Rhodopol® 23, Rhodicare® CFT, or Rhodopol® Extra 2; or diutan gum. Suitable antifoam agents include poly dimethyl siloxanes emulsified in water, such as Foamaster® UDB (Foamaster® is a registered trademark of BASF Corporation, Florham Park, NJ, USA), or SAG™ 1572, or SAG™ 1538, or SAG™ 1599 (SAG™ is a trademark of Momentive Performance materials, Friendly, WV, USA), or Xiameter™ ACP-0001, or Xiameter™ ACP- 0100, or Xiameter™ ACP-1400, or Xiameter™ AFE-0010, or Xiameter™ AFE-0300 (Xiameter™ is a trademark of the Dow Chemical Company, Midland, MI, US), or Antifoam 10, or Antifoam 100, or Antifoam 8810 IND, or Antifoam 8830 IND, or Silfar® S 184; or Silfar® SE 4; or Silfoam® SC 132, or Silfoam® SE-23 (Silfar® and Silfoam® are trademarks of Wacker Silicones, Adrian, MI, USA); or Break-thru® AF 9902, or Break-thru® AF 9903, or Break-thru® AF 9905. Suitable antimicrobial agents include: l,2-benzisothiazolin-3-one, such as Proxel® GXL; 5-chloro-2-methyl-4-isothiazolin-3-one; and 2-methyl4-isothiazolin-3- one, such as Kathon® CG / ICP. Suitable antifreeze agents include: glycols, such as propylene glycol; glycerol; or electrolyte-based antifreeze, such as sodium chloride, or sodium acetate. Suitable pH modifiers include agriculturally-acceptable weak acidic or basic buffers, such as sodium phosphate, potassium phosphate, phosphoric acid, sodium citrate, potassium citrate, citric acid, sodium lactate, potassium lactate, or lactic acid. Suitable built-in adjuvants include: ethoxylated castor oils, such as Agnique® CSO-25, Etocas™ 10, Etocas™ 29, or Etocas™ 40; ethoxylated fatty alcohols, such as Synperonic® 13 / 12; polysorbates, such as Tween® 80; sorbitan esters, such as Span® 80; or phosphates, such as tris(2-ethylhexyl) phosphate (TEHP).
[0086] In a preferred suspo-emulsion formulation with another fungicide, the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, is dissolved in the high flashpoint aromatic solvents, such as Aromatic 100, Aromatic 150, Aromatic 150 ND, Aromatic200, or Aromatic 200 ND, as a part of the oil-in-water emulsion, while the other fungicide is dispersed as solid particles. In one preferred aspect, the other fungicide is Chlorothalonil.
[0087] A soluble liquid formulation is a stable, clear to opalescent liquid containing a solution of the active ingredient, where the active ingredient remains in solution after dilution in water. The soluble liquid formulation may contain water-insoluble ingredients. Soluble liquid formulations may be concentrates, where the concentrate is diluted with water by the end user prior to use.
[0088] Formulations comprising the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, of the present disclosure may be soluble liquid formulations, where the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, may be dissolved in a diluent. The soluble liquid formulation may contain a salt counter ion, a wetting agent, an antifoam agent, an antifreeze, a sequestrant or dispersant agent, a diluent, and a built-in adjuvant. Suitable diluents include: water; a polar solvent such as propylene carbonate; a water- miscible solvent such as Purasolv® EL; or combination thereof. Suitable salt counter ions include: various bases, such as potassium hydroxide or sodium hydroxide; or various amines, such as dimethylamine (DMA), triisopropanolamine (TIP A), monoethanolamine (MEA), or 2- hydroxyethyl(trimethylammonium) (choline). Suitable wetting agents include EO / PO block polymeric ethers such as Polyglycol 26-2 or Polyglycol 26-2N (Polyglycol 26-2 or 26-2N may be obtained from the Dow Chemical Company, Midland, Michigan, USA). Suitable antifoam agents include poly dimethyl siloxanes emulsified in water, such as Foamaster® UDB (Foamaster® is a registered trademark of BASF Corporation, Florham Park, NJ, USA), or SAG™ 1572, or SAG™ 1538, or SAG™ 1599 (SAG™ is a trademark of Momentive Performance materials, Friendly, WV, USA), or Xiameter™ ACP-0001, or Xiameter™ ACP- 0100, or Xiameter™ ACP-1400, or Xiameter™ AFE-0010, or Xiameter™ AFE-0300 (Xiameter™ is a trademark of the Dow Chemical Company, Midland, MI, US), or Antifoam 10, or Antifoam 100, or Antifoam 8810 IND, or Antifoam 8830 IND, or Silfar® S 184; or Silfar® SE 4; or Silfoam® SC 132, or Silfoam® SE-23 (Silfar® and Silfoam® are trademarks of Wacker Silicones, Adrian, MI, USA); or Break-thru® AF 9902, or Break-thru® AF 9903, or Break-thru® AF 9905. Suitable antifreeze agents include: glycols, such as propylene glycol; glycerol; or electrolyte-based antifreeze, such as sodium chloride, or sodium acetate. Suitable sequestrants or dispersants include polyaminocarboxylic acid-lignosulphonates, such as EDTA-lignosulphonates. Suitable diluents include: water or propylene carbonate, such as Jeffsol® AG 1555. Suitable built-in adjuvants include: ethoxylated castor oils, such asAgnique® CSO-25, Etocas™ 10, Etocas 29™, or Etocas™ 40; ethoxylated fatty alcohols, such as Synperonic® 13 / 12); polysorbates, such as Tween® 80; sorbitan esters, such as Span® 80; or phosphates, such as tris(2-ethylhexyl) phosphate (TEHP).
[0089] In various aspects, the formulation may be provided as a high-strength formulation such as a concentrate. In some aspects, the concentrate is stable and retains potency during storage and shipping. In various aspects, the concentrate is a clear, homogeneous liquid that is stable at temperatures of 54 °C or greater. In some aspects, the concentrate does not exhibit any precipitation of solids at temperatures of -10 °C or lower. In some aspects, the concentrate does not exhibit separation, precipitation, or crystallization of any components at low temperatures. For example, the concentrate remains a clear solution at temperatures below 0 °C (e.g., below -5 °C, below -10 °C, below -15 °C). In some aspects, the concentrate exhibits a viscosity of less than 50 centipoise (50 megapascals), even at temperatures as low as 5 °C. In some aspects, the concentrate does not exhibit separation, precipitation, or crystallization of any components during storage for a period of 2 weeks or greater (e.g., 4 weeks, 6 weeks, 8 weeks, 3 months, 6 months, 9 months, or 12 months or greater). In some aspects, the concentrate may be a technical concentrate (TK).
[0090] In some alternative aspects, the formulation in the form of a concentrate may comprise, in weight percent based on the total weight of the formulation, from 15% to about 99%, preferably from about 30% to about 99% of the compound of Formula I (e.g., about 35%, 40%, 45%, 50%, 52.5%, 55%, 60%, 62.5%, 65%, 67.5%, 70%, 72.5%, 75%, 80%, 82.5%, 85%, 87.5%, 90%, 92.5%, 95%, or 97.5% of the compound of Formula I), or within any range defined from any two of the forgoing values, such as from about 30% to about 70%, from about 40% to about 65%, from about 45% to about 75%, from about 50% to about 97.5%, from about 55% to about 85%, from about 60% to about 80%, from about 65% to about 75%, or from about 52.5% to about 72.5% of the compound of Formula I, by weight percent based on the total weight of the formulation. In some aspects, the concentrate is stable and retains potency during storage and shipping.
[0091] In some preferred aspects, the disclosure provides for concentrates comprising the compound of Formula I and a solvent selected from the group consisting of solvents listed in Table A and any combination thereof. Preferably, the disclosure provides for concentrates comprising the compound of Formula I and a solvent selected from the group consisting of solvents listed in Table A. More preferably, the disclosure provides for concentrates comprising the compound of Formula I and a solvent selected from the group consisting ofsolvents listed in Table A, at the compound of Formula I’s concentration equal to or greater than the minimum concentration corresponding to the solvent in Table A. Alternatively preferably, the disclosure provides for concentrates comprising the compound of Formula I and a solvent selected from the group consisting of any combination of solvents listed in Table A.
[0092] In some more preferred aspects, the disclosure provides for concentrates consisting essential of the compound of Formula I and a solvent selected from the group consisting of solvents listed in Table A and any combination thereof.
[0093] In some most preferred aspects, the disclosure provides for concentrates consisting of the compound of Formula I and a solvent selected from the group consisting of solvents listed in Table A and any combination thereof.Table A. Solvents suitable for technical concentrates of the compound of Formula I.
[0094] In some more preferred aspects, the disclosure provides for concentrates comprising the compound of Formula I and a solvent selected from the group consisting of solvents listed in Table B and any combination thereof. Preferably, the disclosure provides for concentrates comprising the compound of Formula I and a solvent selected from the group consisting of solvents listed in Table B. More preferably, the disclosure provides for concentrates comprising the compound of Formula I and a solvent selected from the group consisting of solvents listed in Table B, at the compound of Formula F s concentration equal to or greater than the minimum concentration corresponding to the solvent in Table B. Alternatively preferably, the disclosure provides for concentrates comprising the compound of Formula I and a solvent selected from the group consisting of any combination of solvents listed in Table B.
[0095] In some most preferred aspects, the disclosure provides for concentrates consisting essential of the compound of Formula I and a solvent selected from the group consisting of solvents listed in Table B and any combination thereof.
[0096] In some particularly preferred aspects, the disclosure provides for concentrates consisting of the compound of Formula I and a solvent selected from the group consisting of solvents listed in Table B and any combination thereof.Table B. Preferred solvents suitable for technical concentrates of the compound of Formula I.
[0097] In some more preferred aspects, the formulation in the form of a concentration may comprise a solvent selected from the group consisting of 2-ethylhexanol, Benzyl alcohol, Disponil ANA, Agnique AMD 3L, Genagen NBP (TamiSolve NxG), Hallcomid M-8-10 (Genagen 4166 / Agnique AMD 810), Hallcomid M-10, Hallcomid 1025, Aromatic 100 S, Aromatic 150 ND, Aromatic 200 ND, Jeffsol AG 1555, Surfonic AG 1700, Zendex DB-120, Citrofol Al, Rhodiasolv RPDEZEstasol, Rhodiasolv Polarclean, Solvall BDE-1, Hexylene Glycol, Butyl Cellosolve, Carbitol Solvent, Dowanol DPM (Tersperse 2612 / (2- methoxymethylethoxy)propanol), Cyrene, 2-Heptanone, Purasolv EL, Purasolv EHL (Agnique AE3 2EH), y-Caprolactone, Drakeol 13 L, Jeffsol AG 1730, SURFOM® CE 8434, Stepan C- 42, AGNIQUE ME 18 SD (RADIA 7064 / STEPOSOL M), Agnique ME 18 RD-F (Steposol ROE-W), Stepan 108 (Agnique GTC), TEHP (Disflamoll TOF), and mixtures thereof. Preferably, the formulation in the form of a concentration may comprise 2-ethylhexanol, Benzyl alcohol, Disponil ANA, Agnique AMD 3L, Genagen NBP (TamiSolve NxG), Hallcomid M-8-10 (Genagen 4166 / Agnique AMD 810), Hallcomid M-10, Hallcomid 1025, Aromatic 150 ND, Aromatic 200, Jeffsol AG 1555, Surfonic AG 1700, Zendex DB-120, Citrofol Al, Rhodiasolv RPDEZEstasol, Rhodiasolv Polarclean, Solvall BDE-1, Hexylene Glycol, Butyl Cellosolve, Carbitol Solvent, Dowanol DPM (Tersperse 2612 / (2- methoxymethylethoxy)propanol), Cyrene, 2-Heptanone, Purasolv EL, Purasolv EHL (Agnique AE3 2EH), y-Caprolactone, Drakeol 13 L, Jeffsol AG 1730, SURFOM® CE 8434, Stepan C- 42, AGNIQUE ME 18 SD ( RADIA 7064 / STEPOSOL M), Agnique ME 18 RD-F (Steposol ROE-W), Stepan 108 (Agnique GTC), or TEHP (Disflamoll TOF) as the solvent.
[0098] In some aspects, the formulation is a solid or semi-solid. The solid or semi-solid formulation may be in the form of powders, granules, tablets, briquettes, gels, pastes, or greases. The solid or semi-solid formulations may be mixed with water by the end user before use, or the solid or semi-solid formulations may be applied directly as solids by the end user.
[0099] Powders are free-flowing, finely divided solid formulations. Dustable powders are free-flowing powders suitable for dusting onto the area adjacent to the plant or soil adapted to support growth of the plant, or directly upon to the seed, the root of the plant, and / or foliage of the plant, where control of fungal pathogens and diseases is desired. Emulsifiable powders are powder formulations, which may contain water-insoluble ingredients, to be applied as an oil- in-water emulsion of the active ingredients after dispersion in water or an aqueous liquid. An oil dispersible powder is a powder formulation to be applied as a suspension after dispersion in an organic liquid. A water-soluble powder is a powder formulation to be applied as a truesolution of the active ingredient after dissolution in water or an aqueous liquid, but which may contain insoluble inert ingredients. A wettable powder is a powder formulation to be applied as a suspension after dispersion in water or an aqueous liquid. A water dispersible powder for slurry treatment is a powder to be dispersed at a high concentration in water or an aqueous liquid before application as a slurry. Powders may also be applied onto the area adjacent to the plant or soil adapted to support growth of the plant, or directly upon to the seed, the root of the plant, and / or foliage of the plant, where control of fungal pathogens and diseases is desired.
[0100] Granules are a free-flowing solid formulation of particles that are larger than powders, where the particles are of a defined size range. Typical granules may be roughly spheroid or cuboid in shape, with sizes ranging from about 0.3 mm to about 1 cm in diameter or side. A water soluble granule is a granular formulation containing granules to be applied as a true solution of the active ingredient after dissolution in water or an aqueous liquid, but which may contain insoluble inert ingredients. An emulsifiable granule is a granular formulation, which may include water-insoluble ingredients, which is applied as an oil-in-water emulsion of the active ingredient after disintegration in water or an aqueous liquid. A wettable granule is a granular formulation to be applied as a suspension after the granule is dispersed in water or an aqueous liquid. Granules can also be applied directly to the area adjacent to the plant or soil adapted to support growth of the plant, or upon to the seed, the root of the plant, and / or foliage of the plant, where control of fungal pathogens and diseases is desired.
[0101] Formulations comprising the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, of the present disclosure may be wettable granules including water dispersible granules and soluble granules, where the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, is incorporated in the granule as a solid material. The wettable granule formulation may contain a wetting agent, a dispersing agent, a binding agent, a disintegrating agent or processing aid, a filler or solid diluent, a pH modifier, and an antifoam agent. Suitable wetting agents include: blends of octyl sulfosuccinate and sodium naphthalene, such as Morwet® EFW; sodium lauryl sulfonates, such as Stepanol® ME Dry; sodium taurates, such as Geropon® T-77; or polycarboxylates, such as Geropon® T-36. Suitable dispersing and binding agents include: sodium lignosulfonates, such as Kraftsperse® 25M or Polyfon® (Polyfon® is a registered trademark of Ingevity South Carolina, North Charleston, South Carolina, USA); or condensed naphthalene formaldehydes, such as Morwet® D-425. Suitable disintegrating agents or processing aids include: polymethyl urea resins, such as Pergopak® M (Pergopak® is a registered trademark of J.M. Huber Corporation, Atlanta, GA, USA), orlactose / com starch granulation compositions. Suitable fillers or solid diluents include: organoclays, such as kaolin or bentonite; or lactose monohydrates. Suitable pH modifiers include agriculturally-acceptable weak acidic or basic buffers, such as sodium phosphate, potassium phosphate, phosphoric acid, sodium citrate, potassium citrate, citric acid, sodium lactate, potassium lactate, or lactic acid. Suitable antifoam agents include powder defoamers such as Agnique® Soap L.
[0102] Tablets are dry formulations that are typically in pre-formed and pre-measured solid units of uniform shape and dimensions, often disk-shaped, with either flat or convex faces, where the distance between faces is less than the diameter of the tablet. Tablets for direct application are tablet formulations that can be applied individually and directly in the soil or bodies of water, without preparation of a spraying solution or dispersion. Water soluble tablets are tablet formulations that are used individually to form a solution of the active ingredient after the tablet is disintegrated in water or an aqueous liquid. Water dispersible tablets are tablet formulations that are used individually to form a dispersion of the active ingredient after the tablet is disintegrated in water or an aqueous liquid.
[0103] Briquettes are dry formulations in the form of solid blocks, for controlled release of the active ingredient into water.
[0104] Semi-solid formulations may be in the form of pastes, gels, or greases. A gel is a formulation where in the active ingredient is suspended or dissolved in plastic (that is, gelatinous) semi-solid. A paste is a water-based film-forming composition. A grease is a very viscous formulation where the active ingredient is suspended or dissolved in an oil or fat. A gel or paste concentrate is a solid formulation to be applied as a gel or paste after dilution with water or an aqueous liquid. An emulsifiable gel, paste, or grease is a formulation to be diluted with water or an aqueous liquid to form an emulsion. A water-soluble gel is a formulation to be dissolved in water or an aqueous liquid and applied as an aqueous solution. A gel, paste, or grease may be applied directly without dilution.
[0105] In some aspects, powders, materials for spreading, or dusts can be prepared by mixing or concomitant grinding of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, and optionally other additives with a solid carrier. In some aspects, granules (e.g., coated granules, impregnated granules and homogeneous granules) can be prepared by binding the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, andoptionally other additives with solid carriers. In some aspects, the granules may be prepared using an extrusion process.
[0106] In some aspects, the formulations comprise, in weight percent based on the total weight of the formulation, from about 0.1% to about 99% of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, (e.g., about 0.1%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 7.5%, 8%, 9%, 10%, 12.5%, 15%, 17.5%, 20%, 25%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 82.5%, 85%, 87.5%, 90%, 92.5%, or 95% of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof), or within any range defined from any two of the forgoing values, such as from about 1% to about 95%, from about 10% to about 60%, from about 20% to about 45%, from about 55% to about 82.5%, or from about 12.5% to about 50% of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, by weight percent based on the total weight of the formulation. In some aspects, the liquid formulations comprise, in grams active ingredient per liter (g ai / L) of the formulation, a concentration from about 1 g ai / L to about 850 g ai / L of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, (e.g., about 1, 1.5, 2, 2.5, 3, 4, 5, 6, 7, 7.5, 8, 9, 10, 12.5, 15, 17.5, 20, 25, 30, 35, 40, 45, 50, 60, 70, 75, 80, 90, 100, 110, 112, 115, 117, 120, 125, 130, 140, 150, 160, 170, 175, 180, 190, 200, 210, 215, 220, 225, 230, 240, 250, 275, 300, 325, 350, 375, 400, 425, 450, 475, 500, 525, 550, 575, 600, 625, 650, 675, 700, 725, 750, 800, or 850 g ai / L of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof), or within any range defined from any two of the forgoing values, such as from about 1 g ai / L to about 750 g ai / L, from about 1 g ai / L to about 600 g ai / L, from about 1 g ai / L to about 500 g ai / L, from about 1 g ai / L to about 450 g ai / L, from about 10 g ai / L to about 350 g ai / L, from about 20 g ai / L to about 150 g ai / L, or from about 112 g ai / L to about 250 g ai / L of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof. In some aspects, the solid formulations comprise, in grams active ingredient per kilogram (g ai / kg) of the formulation, a concentration from about 1 g ai / kg to about 750 g ai / kg of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, (e.g., about 1, 1.5, 2, 2.5, 3, 4, 5, 6, 7, 7.5, 8, 9, 10, 12.5, 15, 17.5, 20, 25, 30, 35, 40, 45, 50, 60, 70, 75, 80, 90,100, 110, 112, 115, 117, 120, 125, 130, 140, 150, 160, 170, 175, 180, 190, 200, 210, 215, 220, 225, 230, 240, 250, 275, 300, 325, 350, 375, 400, 425, 450, 475, 500, 525, 550, 575, 600, 625, 650, 700, 725, or 750 g ai / kg of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof), or within any range defined from any two of the forgoing values, such as from about 1 g ai / kg to about 750 g ai / kg, from about 1 g ai / kg to about 600 g ai / kg, from about 1 g ai / kg to about500 g ai / kg, from about 10 g ai / kg to about 400 g ai / kg, from about 100 g ai / kg to about 350 g ai / kg, from about 200 g ai / kg to about 250 g ai / kg, or from about 125 g ai / kg to about 300 g ai / kg of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof. In a formulation designed to be employed as a concentrate, the concentrate can be diluted with an inert carrier, such as water or an aqueous liquid, to form a tank mix prior to application. The tank mix applied to the area adjacent to the plant or soil adapted to support growth of the plant, or directly upon to the seed, the root of the plant, and / or foliage of the plant, can contain from about 0.006 to about 80 g ai / L of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, (e.g., about 0.01, 0.05, 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2, 2.5, 5, 7.5, 10, 11, 12,12.5, 13, 14, 15, 16, 17, 17.5, 18, 19, 20, 22, 22.5, 24, 25, 26, 27.5, 28, 30, 32, 32.5, 34, 35, 36,37.5, 38, 40, 42, 44, 45, 46, 48, 50, 52.5, 55, 57.5, 60, 62.5, 65, 67.5, 70, 72.5, 75, or 77.5 g ai / L of compound of Formula I, or an acceptable salt, solvate, or hydrate thereof,), or within any range defined from any two of the forgoing values, such as from about 0.01 g ai / L to about 30 g ai / L, about 7.5 g ai / L to about 25 g ai / L, about 7.5 g ai / L to about 75 g ai / L, or about 0.25 g ai / L to about 5 g ai / L of the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, in the tank mix.
[0107] In some aspects, the formulations comprise, in weight percent based on the total weight of the formulation, from about 0.1% to about 99% of the compound of Formula B (e.g., about 0.1%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 7.5%, 8%, 9%, 10%, 12.5%, 15%, 17.5%, 20%, 25%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 82.5%, 85%, 87.5%, 90%, 92.5%, or 95% of the compound of Formula LB), or within any range defined from any two of the forgoing values, such as from about 1% to about 95%, from about 10% to about 60%, from about 20% to about 45%, from about 55% to about 82.5%, or from about 12.5% to about 50% of the compound of Formula LB, by weight percent based on the total weight of the formulation. In some aspects, the liquid formulations comprise, in grams active ingredient per liter (g ai / L) of the formulation, a concentration from about 1 g ai / L to about 850 g ai / L of the compound of Formula LB (e.g., about 1, 1.5, 2, 2.5, 3, 4, 5, 6, 7, 7.5, 8, 9, 10, 12.5, 15, 17.5, 20, 25, 30, 35, 40, 45, 50, 60, 70, 75, 80, 90, 100, 110, 112, 115, 117, 120, 125, 130, 140, 150, 160, 170, 175, 180, 190, 200, 210, 215, 220, 225, 230, 240, 250, 275, 300, 325, 350, 375, 400, 425, 450, 475, 500, 525, 550, 575, 600, 625, 650, 675, 700, 725, 750, 800, or 850 g ai / L of the compound of Formula LB), or within any range defined from any two of the forgoing values, such as from about 1 g ai / L to about 750 g ai / L, from about 1 g ai / L to about 600 g ai / L, from about 1 g ai / L to about 500 g ai / L, from about 1 g ai / Lto about 450 g ai / L, from about 10 g ai / L to about 350 g ai / L, from about 20 g ai / L to about 150 g ai / L, or from about 112 g ai / L to about 250 g ai / L of the compound of Formula LB. In some aspects, the solid formulations comprise, in grams active ingredient per kilogram (g ai / kg) of the formulation, a concentration from about 1 g ai / kg to about 750 g ai / kg of the compound of Formula I-B (e.g., about 1, 1.5, 2, 2.5, 3, 4, 5, 6, 7, 7.5, 8, 9, 10, 12.5, 15, 17.5, 20, 25, 30, 35, 40, 45, 50, 60, 70, 75, 80, 90,100, 110, 112, 115, 117, 120, 125, 130, 140, 150, 160, 170, 175, 180, 190, 200, 210, 215, 220, 225, 230, 240, 250, 275, 300, 325, 350, 375, 400, 425, 450, 475, 500, 525, 550, 575, 600, 625, 650, 700, 725, or 750 g ai / kg of the compound of Formula LB), or within any range defined from any two of the forgoing values, such as from about 1 g ai / kg to about 750 g ai / kg, from about 1 g ai / kg to about 600 g ai / kg, from about 1 g ai / kg to about 500 g ai / kg, from about 10 g ai / kg to about 400 g ai / kg, from about 100 g ai / kg to about 350 g ai / kg, from about 200 g ai / kg to about 250 g ai / kg, or from about 125 g ai / kg to about 300 g ai / kg of the compound of Formula B. In a formulation designed to be employed as a concentrate, the concentrate can be diluted with an inert carrier, such as water or an aqueous liquid, to form a tank mix prior to application. The tank mix applied to the area adjacent to the plant or soil adapted to support growth of the plant, or directly upon to the seed, the root of the plant, and / or foliage of the plant, can contain from about 0.006 to about 80 g ai / L of the compound of Formula I-B (e.g., about 0.01, 0.05, 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2, 2.5, 5, 7.5, 10, 11, 12, 12.5, 13, 14, 15, 16, 17, 17.5, 18, 19, 20, 22, 22.5, 24, 25, 26, 27.5, 28, 30, 32, 32.5, 34, 35, 36, 37.5, 38, 40, 42, 44, 45, 46, 48, 50, 52.5, 55, 57.5, 60, 62.5, 65, 67.5, 70, 72.5, 75, or 77.5 g ai / L of compound of Formula LB), or within any range defined from any two of the forgoing values, such as from about 0.01 g ai / L to about 30 g ai / L, about 7.5 g ai / L to about 25 g ai / L, about 7.5 g ai / L to about 75 g ai / L, or about 0.25 g ai / L to about 5 g ai / L of the compound of Formula B, in the tank mix.B. Additives[0.108] The pesticidal formulations containing the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, disclosed herein can also comprise one or more additives, such as the additives described herein above. In some aspects, the additive is premixed with the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof. In some aspects, the additive is added sequentially. In some aspects, the additive is added simultaneously.1. Other Pesticides
[0109] Some aspects of the described pesticidal formulations include adding one or more additional pesticide active ingredients to the pesticidal formulations. These pesticide active ingredients may include one or more of an herbicide, an insecticide, a fungicide, a nematocide, a miticide, an arthropodicide, a bactericide, a plant growth regulator, or combinations thereof that are compatible with the formulations of the present disclosure.
[0110] Examples of additional pesticides include: (3-ethoxypropyl)mercury bromide, 1,2- dibromoethane, 1,2-dichloroethane, 1,2-di chloropropane, 1,3 -di chloropropene, 1-MCP, 1- methylcyclopropene, 1-naphthol, 2-(octylthio)ethanol, 2,3,3-TPA, 2,3,5-tri-iodobenzoic acid, 2,3,6-TBA, 2,4, 5-T, 2,4,5-TB, 2,4,5-TP, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 2,4-DES, 2,4-DP, 2,4-MCPA, 2,4-MCPB, 2iP, 2-methoxyethylmercury chloride, 2-phenylphenol, 3,4-DA, 3,4- DB, 3,4-DP, 3,6-dichloropicolinic acid, 4-aminopyridine, 4-CPA, 4-CPB, 4-CPP, 4- hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate, 8-phenylmercurioxyquinoline, abamectin, abamectin-aminomethyl, abscisic acid, ACC, acephate, acequinocyl, acetamiprid, acethion, acetochlor, acetofenate, acetophos, acetoprole, acibenzolar, acifluorfen, aclonifen, ACN, acrep, acrinathrin, acrolein, acrylonitrile, acynonapyr, acypetacs, afidopyropen, afoxolaner, alachlor, alanap, alanycarb, albendazole, aldicarb, aldicarb sulfone, aldimorph, aldoxycarb, aldrin, allethrin, allicin, allidochlor, allosamidin, alloxydim, allyl alcohol, allyxycarb, alorac, a / / ra-cypermethrin, a / / ra-endosulfan, alphamethrin, altretamine, aluminium phosphide, aluminum phosphide, ametoctradin, ametridione, ametryn, ametryne, amibuzin, amicarbazone, amicarthiazol, amidithion, amidoflumet, amidosulfuron, aminocarb, aminocyclopyrachlor, aminopyralid, aminopyrifen, aminotriazole, amiprofos-methyl, amiprophos, amiprophos-methyl, amisulbrom, amiton, amitraz, amitrole, ammonium sulfamate, amobam, amorphous silica gel, amorphous silicon dioxide, ampropylfos, AMS, anabasine, ancymidol, anilazine, anilofos, anisflupurin, anisuron, anthraquinone, antu, apholate, aramite, arprocarb, arsenous oxide, asomate, aspirin, asulam, athidathion, atraton, atrazine, aureofungin, avermectin Bl, AVG, aviglycine, azaconazole, azadirachtin, azafenidin, azamethiphos, azidithion, azimsulfuron, azinphosethyl, azinphos-ethyl, azinphosmethyl, azinphos-methyl, aziprotryn, aziprotryne, azithiram, azobenzene, azocyclotin, azothoate, azoxystrobin, bachmedesh, barban, barbanate, barium hexafluorosilicate, barium polysulfide, barium silicofluoride, barthrin, basic copper carbonate, basic copper chloride, basic copper sulfate, BCPC, beflubutamid, beflubutamid-M, benalaxyl, benalaxyl-M, benazolin, bencarbazone, benclothiaz, bendaqingbingzhi, bendiocarb, bendioxide, benefin, benfluralin,benfuracarb, benfuresate, benmihuangcaoan, benodanil, benomyl, benoxacor, benoxafos, benquinox, benquitrione, bensulfuron, bensulide, bensultap, bentaluron, bentazon, bentazone, benthiavalicarb, benthiazole, benthiocarb, bentioflumin, bentranil, benzadox, benzalkonium chloride, benzamacril, benzamizole, benzamorf, benzene hexachloride, benzfendizone, benzimine, benzipram, benzobicyclon, benzoepin, benzofenap, benzofluor, benzohydroxamic acid, benzomate, benzophosphate, benzothiadi azole, benzovindiflupyr, benzoximate, benzoylprop, benzpyrimoxan, benzthiazuron, benzuocaotong, benzyl benzoate, benzyladenine, berberine, Z>eta-cyfluthrin, Z>eta-cypermethrin, bethoxazin, BHC, bialaphos, bicyclopyrone, bifemetstrobin, bifenazate, bifenox, bifenthrin, bifujunzhi, bilanafos, binapacryl, bingqingxiao, bioallethrin, bioethanomethrin, biopermethrin, bioresmethrin, biphenyl, bipyrazone, bisazir, bismerthiazol, bismerthiazol-copper, bisphenylmercury methylenedi(x-naphthalene-y- sulphonate), bispyribac, bistrifluron, bisulflufen, bisultap, bitertanol, bithionol, bixafen, bixlozone, blasticidin-S, borax, Bordeaux mixture, boric acid, boscalid, BPPS, brassinolide, brassinolide-ethyl, brevicomin, broclozone, brodifacoum, brofenprox, brofenvalerate, broflanilide, brofluthrinate, bromacil, bromadiolone, bromchlophos, bromethalin, bromethrin, bromfenvinfos, bromoacetamide, bromobonil, bromobutide, bromociclen, bromocyclen, bromo-DDT, bromofenoxim, bromofos, bromomethane, bromophos, bromophos-ethyl, bromopropylate, bromothalonil, bromoxynil, brompyrazon, bromuconazole, bronopol, BRP, BTH, bucarpolate, bufencarb, buminafos, bupirimate, buprofezin, Burgundy mixture, busulfan, busulphan, butacarb, butachlor, butafenacil, butam, butamifos, butane-fipronil, butathiofos, butenachlor, butene-fipronil, butethrin, buthidazole, buthiobate, buthiuron, butifos, butocarboxim, butonate, butopyronoxyl, butoxycarboxim, butralin, butrizol, butroxydim, buturon, butylamine, butylate, butylchlorophos, butylene-fipronil, cacodylic acid, cadusafos, cafenstrole, calciferol, calcium arsenate, calcium chlorate, calcium cyanamide, calcium cyanide, calcium polysulfide, calvinphos, cambendichlor, camphechlor, camphor, captafol, captan, carbarn, carbamorph, carbanolate, carbaril, carbaryl, carbasulam, carbathion, carbendazim, carbendazol, carbetamide, carbofenotion, carbofuran, carbon disulfide, carbon tetrachloride, carbonyl sulfide, carbophenothion, carbophos, carbosulfan, carboxazole, carboxide, carboxin, carfentrazone, carpropamid, cartap, carvacrol, carvone, CAVP, CDAA, CDEA, CDEC, cellocidin, CEPC, ceralure, cerenox, cevadilla, Cheshunt mixture, chinalphos, chinalphos-methyl, chinomethionat, chinomethionate, chiralaxyl, chitosan, chi obenthi azone, chlomethoxyfen, chloralose, chloramben, chloramine phosphorus, chloramphenicol, chloraniformethan, chloranil, chloranocryl, chlorantraniliprole, chlorazifop, chlorazine, chlorbenside, chlorbenzuron, chlorbicyclen, chlorbromuron, chlorbufam, chlordane,chlordecone, chlordimeform, chlorempenthrin, chloretazate, chi or ethephon, chlorethoxyfos, chloreturon, chlorfenac, chlorfenapyr, chlorfenazole, chlorfenethol, chlorfenidim, chlorfenprop, chlorfenson, chlorfensulphide, chlorfenvinphos, chlorfenvinphos-methyl, chlorfluazuron, chlorflurazole, chlorflurecol, chlorfluren, chlorflurenol, chloridazon, chlorimuron, chlorinate, chlor-IPC, chlormephos, chlormequat, chlormesulone, chlormethoxynil, chlornidine, chlornitrofen, chloroacetic acid, chlorobenzilate, chlorodinitronaphthalenes, chlorofenizon, chloroform, chloroinconazide, chloromebuform, chloromethiuron, chloroneb, chlorophacinone, chlorophos, chloropicrin, chloropon, chloroprallethrin, chloropropylate, chlorothalonil, chlorotoluron, chloroxifenidim, chloroxuron, chloroxynil, chlorphonium, chlorphoxim, chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos, chlorpyrifos-methyl, chlorquinox, chlorsulfuron, chlorthal, chlorthiamid, chlorthiophos, chlortoluron, chlozolinate, chitosan, cholecalciferol, choline chloride, chromafenozide, cicloheximide, cimectacarb, cimetacarb, cinerin I, cinerin II, cinerins, cinflubrolin, cinidon-ethyl, cinmethylin, cinosulfuron, cintofen, ciobutide, cisanilide, cismethrin, clacyfos, clefoxydim, clenpirin, clenpyrin, clethodim, climbazole, cliodinate, clodinafop, cloethocarb, clofencet, clofenotane, clofentezine, clofenvinfos, clofibric acid, clofop, clomazone, clomeprop, clonitralid, cloprop, cloproxydim, clopyralid, cloquintocet, cloransulam, closantel, clothianidin, clotrimazole, cloxyfonac, cloxylacon, clozylacon, CMA, CMMP, CMP, CMU, codlelure, colecalciferol, colophonate, copper 8-quinolinolate, copper acetate, copper acetoarsenite, copper arsenate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper silicate, copper sulfate, copper sulfate, basic, copper zinc chromate, coumachlor, coumafene, coumafos, coumafuryl, coumaphos, coumatetralyl, coumethoxystrobin, coumithoate, coumoxystrobin, CPMC, CPMF, CPPC, credazine, cresol, cresylic acid, crimidine, crotamiton, crotoxyfos, crotoxyphos, crufomate, cryolite, cue-lure, cufraneb, cumyleron, cumyluron, cuprobam, cuprous oxide, curcumenol, CVMP, cyanamide, cyanatryn, cyanazine, cyanofenphos, cyanogen, cyanophos, cyanthoate, cyantraniliprole, cyanuric acid, cyazofamid, cybenzoxasulfyl, cybutryne, cyclafuramid, cyclanilide, cyclaniliprole, cyclethrin, cycloate, cyclobutrifluram, cycloheximide, cycloprate, cycloprothrin, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyenopyrafen, cyetpyrafen, cyflufenamid, cyflumetofen, cyfluthrin, cyhalodiamide, cyhalofop, cyhalothrin, cyhexatin, cymiazole, cymoxanil, cyometrinil, cypendazole, cypermethrin, cyperquat, cyphenothrin, cyprazine, cyprazole, cyproconazole, cyprodinil, cyproflanilide, cyprofuram, cypromid, cyprosulfamide, cypyrafluone, cyromazine, cythioate, cytrex, daimuron, dalapon, daminozide, dayoutong, dazomet, DBCP, tZ-camphor,DCB, DCIP, DCPA (Japan), DCPA (USA), DCPTA, DCU, DDD, DDPP, DDT, DDVP, debacarb, decafentin, decamethrin, decarbofuran, deet, dehydroacetic acid, deiquat, delachlor, delnav, deltamethrin, demephion, demephion-O, demephion-S, demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methyl sulphone, demeton-S-methylsulphon, DEP, depallethrine, derris, desmedipham, desmetryn, desmetryne, d-fanshiluquebingjuzhi, diafenthiuron, dialifor, dialifos, diallate, di-allate, diamidafos, dianat, diatomaceous earth, diatomite, diazinon, dibrom, dibutyl phthalate, dibutyl succinate, dicamba, dicapthon, dichlobenil, dichlobentiazox, dichlofenthion, dichlofluanid, dichlone, dichloralurea, dichlorbenzuron, dichlorfenidim, dichlorflurecol, di chlorflurenol, dichlormate, dichlormid, dichloromethane, dichlorophen, dichlorprop, dichlorprop-P, dichlorvos, dichlozolin, dichlozoline, diclobutrazol, diclocymet, diclofop, diclomezine, dicloran, dicloromezotiaz, diclosulam, dicofol, dicophane, dicoumarol, dicresyl, dicrotophos, dicryl, dicumarol, dicyclanil, dicyclonon, dieldrin, dienochlor, diethamquat, diethatyl, diethion, diethion, diethofencarb, dietholate, diethon, diethyl pyrocarbonate, diethyltoluamide, difenacoum, difenoconazole, difenopenten, difenoxuron, difenzoquat, difethialone, diflovidazin, diflubenzuron, diflufenican, diflufenicanil, diflufenzopyr, diflumetorim, dikegulac, dilor, dimatif, dimefluthrin, dimefox, dimefuron, dimehypo, dimepiperate, dimesulfazet, dimetachlone, dimetan, dimethacarb, dimethachlone, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethirimol, dimethoate, dimethomorph, dimethrin, dimethyl carbate, dimethyl disulfide, dimethyl phthalate, dimethylvinphos, dimetilan, dimexano, dimidazon, dimoxystrobin, dimpropyridaz, dimpylate, dimuron, dinex, dingjunezuo, diniconazole, diniconazole-M, dinitramine, dinitrophenols, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinofenate, dinopenton, dinoprop, dinosam, dinoseb, dinosulfon, dinotefuran, dinoterb, dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathion, dioxation, dioxopyritrione, diphacin, diphacinone, diphenadione, diphenamid, diphenamide, diphenyl sulfone, diphenylamine, diphenylsulphide, diprogulic acid, dipropalin, dipropetryn, dipterex, dipymetitrone, dipyrithione, diquat, disodium tetraborate, disosultap, disparlure, disugran, disul, disulfiram, disulfoton, ditalimfos, dithianon, dithicrofos, dithioether, dithiometon, dithiopyr, diuron, dixanthogen, d-limonene, DMDS, DMPA, DNOC, dodemorph, dodicin, dodine, dofenapyn, doguadine, dominicalure, doramectin, DPC, drazoxolon, DSMA, d-trans-allethrin, d-trans-resmethrin, dufulin, dymron, EBEP, EBP, ebufos, ecdysterone, echlomezol, EDB, EDC, EDDP, edifenphos, eglinazine, emamectin, EMPC, empenthrin, enadenine, endosulfan, endothal, endothall, endothion, endrin, enestroburin, enilconazole, enoxastrobin, ephirsulfonate, EPN, epocholeone, epofenonane,epoxiconazole, eprinomectin, epronaz, epsilon-metofluthrin, epsilon-momfluorothrin, EPTC, epyrifenacil, erbon, ergocalciferol, erlujixiancaoan, esdepallethrine, esfenval erate, ESP, esprocarb, etacelasil, etaconazole, etaphos, etem, ethaboxam, ethachlor, ethalfluralin, ethametsulfuron, ethaprochlor, ethephon, ethidimuron, ethiofencarb, ethiolate, ethion, ethiozin, ethiprole, ethirimol, ethoate-methyl, ethobenzanid, ethofumesate, ethohexadiol, ethoprop, ethoprophos, ethoxyfen, ethoxyquin, ethoxysulfuron, ethychlozate, ethyl formate, ethyl pyrophosphate, ethylan, ethyl-DDD, ethylene, ethylene dibromide, ethylene dichloride, ethylene oxide, ethylicin, ethylmercury 2,3 -dihydroxypropyl mercaptide, ethylmercury acetate, ethylmercury bromide, ethylmercury chloride, ethylmercury phosphate, etinofen, ETM, etnipromid, etobenzanid, etofenprox, etoxazole, etridiazole, etrimfos, etrimphos, eugenol, EXD, famoxadone, famphur, fenac, fenamidone, fenaminosulf, fenaminstrobin, fenamiphos, fenapanil, fenarimol, fenasulam, fenazaflor, fenazaquin, fenbuconazole, fenbutatin oxide, fenchlorazole, fenchlorphos, fenclofos, fenclorim, feneptamidoquin, fenethacarb, fenfluthrin, fenfuram, fenhexamid, fenidin, fenitropan, fenitrothion, fenizon, fenjuntong, fenmezoditiaz, fenobucarb, fenolovo, fenoprop, fenopyramid, fenothiocarb, fenoxacrim, fenoxanil, fenoxaprop, fenoxaprop-P, fenoxasulfone, fenoxycarb, fenpiclonil, fenpicoxamid, fenpirithrin, fenpropathrin, fenpropidin, fenpropimorph, fenpyrazamine, fenpyrazone, fenpyroximate, fenquinotrione, fenridazon, fenson, fensulfothion, fenteracol, fenthiaprop, fenthion, fenthion- ethyl, fentiaprop, fentin, fentrazamide, fentrifanil, fenuron, fenuron-TCA, fenvalerate, feproxydim, ferbam, ferimzone, ferric phosphate, ferrous sulfate, fipronil, flamprop, flamprop- M, flazasulfuron, flocoumafen, flometoquin, flonicamid, florasulam, florpyrauxifen, florylpicoxamid, fluacrypyrim, fluazaindolizine, fluazifop, fluazifop-P, fluazinam, fluazolate, fluazuron, flubendiamide, flubeneteram, flubenzimine, flubrocythrinate, flucarbazone, flucetosulfuron, fluchloralin, fluchloraminopyr, fluchlordiniliprole, flucofuron, flucycloxuron, flucythrinate, fludioxonil, fluenethyl, fluenetil, fluensulfone, flufenacet, flufenerim, flufenican, flufenoxadiazam, flufenoximacil, flufenoxuron, flufenoxystrobin, flufenprox, flufenpyr, flufenzine, flufiprole, fluhexafon, fluindapyr, flumethrin, flumetnicam, flumetover, flumetralin, flumetsulam, flumetyl sulforim, flumezin, flumiclorac, flumioxazin, flumipropyn, flumorph, fluometuron, fluopicolide, fluopimomide, fluopyram, fluorbenside, fluoridamid, fluoroacetamide, fluoroacetic acid, fluorochloridone, fluorodifen, fluoroglycofen, fluoroimide, fluoromide, fluoromidine, fluoronitrofen, fluoroxypyr, fluothiuron, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluoxytioconazole, flupentiofenox, flupoxam, flupropacil, flupropadine, flupropanate, flupyradifurone, flupyrimin, flupyroxystrobin, flupyrsulfuron, fluquinconazole, fluquinometoate, fluralaner, flurazole, flurecol, flurenol, fluridone,flurochloridone, fluromidine, fluroxypyr, flurprimidol, flursulamid, flurtamone, flusilazole, flusulfamide, flusulfinam, flutenzine, fluthiacet, fluthiamide, flutianil, flutolanil, flutriafol, fluvalinate, fluxametamide, fluxapyroxad, fluxofenim, folpel, folpet, fomesafen, fonofos, foramsulfuron, for chlorfenuron, formaldehyde, formetanate, formothion, formparanate, fosamine, fosetyl, fosmethilan, fospirate, fosthiazate, fosthietan, frontalin, fthalide, fuberidazole, fucaojing, fucaomi, fujunmanzhi, fulumi, fumarin, funaihecaoling, fuphenthiourea, furalane, furalaxyl, furamethrin, furametpyr, furan tebufenozide, furathiocarb, furcarbanil, furconazole, furconazole-c / .s, furethrin, furfural, furilazole, furmecyclox, furophanate, furyloxyfen, galquin, gamma-BHC, gamma-cyhalothrin, gamma-HCH, genit, gibberellic acid, gibberellin A3, gibberellins, gliftor, glitor, glucochloralose, glufosinate, glufosinate-P, glyodin, glyoxime, glyphosate, glyphosine, gossyplure, grandlure, griseofulvin, guanoctine, guazatine, halacrinate, halauxifen, halfenprox, halofenozide, halosafen, halosulfuron, haloxydine, haloxyfop, haloxyfop-P, haloxyfop-R, HCA, HCB, HCH, hemel, hempa, HEOD, heptachlor, heptafluthrin, heptenophos, heptopargil, herbimycin, herbimycin A, heterophos, hexachlor, hexachloran, hexachloroacetone, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexaflumuron, hexafluoramin, hexaflurate, hexalure, hexamide, hexazinone, hexylthiofos, hexythiazox, HHDN, holosulf, homobrassinolide, huancaiwo, huanchongjing, huangcaoling, huanjunzuo, hydramethylnon, hydrargaphen, hydrated lime, hydrogen cyanamide, hydrogen cyanide, hydroprene, hydroxyisoxazole, hymexazol, hyquincarb, IAA, IBA, IBP, icafolin, icaridin, imazalil, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, imibenconazole, imicyafos, imidacloprid, imidaclothiz, iminoctadine, imiprothrin, inabenfide, indanofan, indazapyroxamet, indaziflam, indolauxipyr, indoxacarb, inezin, infusorial earth, inpyrfluxam, iodobonil, iodocarb, iodofenphos, iodomethane, iodosulfuron, iofensulfuron, ioxynil, ipazine, IPC, ipconazole, ipfencarbazone, ipfentrifluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, iprymidam, ipsdienol, ipsenol, IPSP, iptriazopyrid, IPX, isamidofos, isazofos, isobenzan, isocarbamid, isocarbamide, isocarbophos, isocil, isocycloseram, isodrin, isofenphos, isofenphos-methyl, isofetamid, isoflualanam, isoflucypram, isolan, isomethiozin, isonoruron, isopamphos, isopolinate, isoprocarb, isoprocil, isopropalin, isopropazol, isoprothiolane, isoproturon, isopyrazam, isopyrimol, isothioate, isotianil, isouron, isovaledione, isoxaben, isoxachlortole, isoxadifen, isoxaflutole, isoxapyrifop, isoxathion, isuron, ivermectin, ixoxaben, izopamfos, izopamphos, japonilure, japothrins, jasmolin I, jasmolin II, jasmonic acid, jiahuangchongzong, jiajizengxiaolin, jiaxiangjunzhi, jiecaowan, jiecaoxi, Jinganmycin A, jodfenphos, juvenile hormone I, juvenilehormone II, juvenile hormone III, kadethrin, A / / y / -bifenthrin, ^a / ? / ?a-tefluthrin, karbutilate, karetazan, kasugamycin, kejunlin, kelevan, ketospiradox, kieselguhr, kinetin, kinoprene, kiralaxyl, kresoxim-methyl, kuicaoxi, lactofen, / r / a-cyhalothrin, lancotrione, latilure, lead arsenate, ledprona, lenacil, lepimectin, leptophos, lianbenjingzhi, lime sulfur, lindane, lineatin, linuron, lirimfos, litlure, looplure, lotilaner, lufenuron, liifuqingchongxianan, liixiancaolin, Ivdingjunzhi, Ivfumijvzhi, Ivxiancaolin, lythidathion, M-74, M-81, MAA, magnesium phosphide, malathion, maldison, maleic hydrazide, malonoben, maltodextrin, MAMA, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, matrine, mazidox, MCC, MCP, MCPA, MCPA-thioethyl, MCPB, MCPP, mebenil, mecarbam, mecarbinzid, mecarphon, mecoprop, mecoprop-P, medimeform, medinoterb, medlure, mefenacet, mefenoxam, mefenpyr, mefentrifluconazole, mefluidide, megatomoic acid, melissyl alcohol, melitoxin, MEMC, menazon, MEP, mepanipyrim, meperfluthrin, mephenate, mephosfolan, mepiquat, mepronil, meptyldinocap, mercaptodimethur, mercaptophos, mercaptophos thiol, mercaptothion, mercuric chloride, mercuric oxide, mercurous chloride, merphos, merphos oxide, mesoprazine, mesosulfuron, mesotrione, mesulfen, mesulfenfos, mesulphen, metacresol, metaflumizone, metalaxyl, metalaxyl-M, metaldehyde, metam, metamifop, metamitron, metaphos, metarylpicoxamid, metaxon, metazachlor, metazosulfuron, metazoxolon, metcamifen, metconazole, metepa, metflurazon, methabenzthiazuron, methacrifos, methalpropalin, metham, methamidophos, methasulfocarb, methazole, methfuroxam, methibenzuron, methidathion, methiobencarb, methiocarb, methiopyrisulfuron, methiotepa, methiozolin, methiuron, methocrotophos, metholcarb, methometon, methomyl, methoprene, methoprotryn, methoprotryne, methoquin-butyl, methothrin, methoxychlor, methoxyfenozide, methoxyphenone, methyl apholate, methyl bromide, methyl eugenol, methyl iodide, methyl isothiocyanate, methyl parathion, methylacetophos, methylchloroform, methyldithiocarbamic acid, methyldymron, methylene chloride, methyl-isofenphos, methylmercaptophos, methylmercaptophos oxide, methylmercaptophos thiol, methylmercury benzoate, methylmercury dicyandiamide, methylmercury pentachlorophenoxide, methylneodecanamide, methylnitrophos, methyltriazothion, metiozolin, metiram, metiram- zinc, metobenzuron, metobromuron, metofluthrin, metolachlor, metolcarb, metometuron, metominostrobin, metosulam, metoxadiazone, metoxuron, metproxybicyclone, metrafenone, metriam, metribuzin, metrifonate, metriphonate, metsulfovax, metsulfuron, metyltetraprole, mevinphos, mexacarbate, miechuwei, mieshuan, miewenjuzhi, milbemectin, milbemycin oxime, milneb, mimanan, mipafox, MIPC, mirex, mivorilaner, MNAF, modoflaner, moguchun, molinate, molosultap, momfluorothrin, monalide, monisuron, monoamitraz,monochloroacetic acid, monocrotophos, monolinuron, monomehypo, monosulfiram, monosulfuron, monosultap, monuron, monuron-TCA, morfamquat, moroxydine, morphothion, morzid, moxidectin, MPMC, MSMA, MTMC, muscalure, myclobutanil, myclozolin, myricyl alcohol, A-(ethylmercury)- / ?-toluenesulphonanilide, NAA, NAAm, nabam, naftalofos, naled, naphthalene, naphthaleneacetamide, naphthalic anhydride, naphthalophos, naphthoxyacetic acids, naphthyl acetic acids, naphthylindane- 1,3 -di ones, naphthyloxyacetic acids, naproanilide, napropamide, napropamide-M, naptalam, natamycin, NBPOS, neburea, neburon, nendrin, neonicotine, nichlorfos, niclofen, niclosamide, nicobifen, nicofluprole, nicosulfuron, nicotine, nicotine sulfate, nifluridide, nikkomycins, NIP, nipyraclofen, nipyralofen, nitenpyram, nithiazine, nitralin, nitrapyrin, nitrilacarb, nitrofen, nitrofluorfen, nitrostyrene, nitrothal- isopropyl, nobormide, nonanol, norbormide, norea, norflurazon, nomicotine, noruron, novaluron, noviflumuron, NPA, nuarimol, nuranone, OCH, octachlorodipropyl ether, octhilinone, o-di chlorobenzene, ofurace, omethoate, o-phenyl phenol, orbencarb, orfralure, orthobencarb, ortho- chlorobenzene, orthosulfamuron, oryctalure, orysastrobin, oryzalin, osthol, osthole, ostramone, ovatron, ovex, oxabetrinil, oxadiargyl, oxadiazon, oxadixyl, oxamate, oxamyl, oxapyrazon, oxapyrazone, oxasulfuron, oxathiapiprolin, oxaziclomefone, oxazosulfyl, oxine-copper, oxine-Cu, oxolinic acid, oxpoconazole, oxycarboxin, oxydemeton- methyl, oxydeprofos, oxy di sulfoton, oxyenadenine, oxyfluorfen, oxymatrine, oxytetracycline, oxythioquinox, PAC, paclobutrazol, paichongding, pallethrine, PAP, para- chlorobenzene, parafluron, paraquat, parathion, parathion-methyl, parinol, Paris green, PCNB, PCP, PCP-Na, / ?-dichlorobenzene, PDJ, pebulate, pedinex, pefurazoate, pelargonic acid, penconazole, pencycuron, pendimethalin, penfenate, penflufen, penfluron, penoxalin, penoxsulam, pentachlorophenol, pentachlorophenyl laurate, pentanochlor, penthiopyrad, pentmethrin, pentoxazone, perchlordecone, perfluidone, permethrin, pethoxamid, PHC, phenamacril, phenamacril-ethyl, phenaminosulf, phenazine oxide, phenetacarbe, phenisopham, phenkapton, phenmedipham, phenmedipham-ethyl, phenob enzur on, phenothiol, phenothrin, phenproxide, phenthoate, phenylmercuriurea, phenylmercury acetate, phenylmercury chloride, phenylmercury derivative of pyrocatechol, phenylmercury nitrate, phenylmercury salicylate, phorate, phosacetim, phosalone, phosametine, phosazetim, phosazetin, phoscyclotin, phosdiphen, phosethyl, phosfolan, phosfolan-methyl, phosglycin, phosmet, phosnichlor, phosphamide, phosphamidon, phosphine, phosphinothricin, phosphocarb, phosphorus, phostin, phoxim, phoxim-methyl, phthalide, phthalophos, phthalthrin, picarbutrazox, picaridin, picloram, picolinafen, picoxystrobin, pimaricin, pindone, pinoxaden, pioxaniliprole, piperalin, piperazine, piperflanilide, piperonyl butoxide, piperonyl cyclonene, piperophos, piproctanly,piproctanyl, piprotal, pirimetaphos, pirimicarb, piriminil, pirimioxyphos, pirimiphos-ethyl, pirimiphos-methyl, pival, pivaldione, plifenate, PMA, PMP, polybutenes, polycarbamate, polychlorcamphene, polyethoxyquinoline, polyoxin D, polyoxins, polyoxorim, polythialan, potassium arsenite, potassium azide, potassium cyanate, potassium ethylxanthate, potassium naphthenate, potassium polysulfide, potassium thiocyanate, pp'-DDT, prallethrin, precocene I, precocene II, precocene III, pretilachlor, primidophos, primisulfuron, probenazole, prochloraz, proclonol, procyazine, procymidone, prodiamine, profenofos, profluazol, profluralin, profluthrin, profoxydim, profurite-aminium, proglinazine, prohexadione, prohydrojasmon, promacyl, promecarb, prometon, prometryn, prometryne, promurit, pronamide, pronitridine, propachlor, propafos, propamidine, propamocarb, propanil, propaphos, propaquizafop, propargite, proparthrin, propazine, propetamphos, propham, propiconazole, propidine, propineb, propisochlor, propoxur, propoxycarbazone, propyl isome, propyrisulfuron, propyzamide, proquinazid, prosuler, prosulfalin, prosulfocarb, prosulfuron, prothidathion, prothiocarb, prothioconazole, prothiofos, prothoate, protrifenbute, proxan, prymidophos, prynachlor, psoralen, psoralene, pydanon, pydiflumetofen, pyflubumide, pymetrozine, pyracarbolid, pyraclofos, pyraclonil, pyraclostrobin, pyraflufen, pyrafluprole, pyramat, pyrametostrobin, pyraoxystrobin, pyrapropoyne, pyraquinate, pyrasulfotole, pyraziflumid, pyrazolate, pyrazolynate, pyrazon, pyrazophos, pyrazosulfuron, pyrazothion, pyrazoxyfen, pyresmethrin, pyrethrin I, pyrethrin II, pyrethrins, pyribambenz-isopropyl, pyribambenz- propyl, pyribencarb, pyribenzoxim, pyributicarb, pyriclor, pyridaben, pyridachlometyl, pyridafol, pyridalyl, pyridaphenthion, pyridaphenthione, pyridate, pyridinitril, pyrifenox, pyriflubenzoxim, pyrifluquinazon, pyriftalid, pyrimetaphos, pyrimethanil, pyrimicarbe, pyrimidifen, pyriminobac, pyriminostrobin, pyrimiphos-ethyl, pyrimiphos-methyl, pyrimisulfan, pyrimitate, pyrinuron, pyriofenone, pyriprole, pyripropanol, pyriproxyfen, pyrisoxazole, pyrithiobac, pyrolan, pyroquilon, pyroxasulfone, pyroxsulam, pyroxychlor, pyroxyfur, qincaosuan, qingkuling, quassia, quinacetol, quinalphos, quinalphos-methyl, quinazamid, quinclorac, quinconazole, quinmerac, quinoclamine, quinofumelin, quinomethionate, quinonamid, quinothion, quinoxyfen, quintiofos, quintozene, quizalofop, quizalofop-P, quwenzhi, quyingding, rabenzazole, rafoxanide, R-diniconazole, rebemide, reglone, renriduron, rescalure, resmethrin, rhodethanil, rhodojaponin-III, ribavirin, rimisoxafen, rimsulfuron, rizazole, R-metalaxyl, rodethanil, ronnel, rotenone, ryania, sabadilla, saflufenacil, saijunmao, saisentong, salicylanilide, salifluofen, sanguinarine, santonin, S- bioallethrin, schradan, scilliroside, seboctylamine, sebuthylazine, secbumeton, sedaxane, selamectin, semiamitraz, sesamex, sesamolin, sesone, sethoxydim, sevin, shuangjiaancaolin,shuangjianancaolin, S-hydroprene, siduron, sifumijvzhi, siglure, silafluofen, silatrane, silica aerogel, silica gel, silthiofam, silthiopham, silthiophan, silvex, simazine, simeconazole, simeton, simetryn, simetryne, sintofen, S-kinoprene, slaked lime, SMA, S-methoprene, S- metolachlor, sodium arsenite, sodium azide, sodium chlorate, sodium cyanide, sodium fluoride, sodium fluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodium o- phenylphenoxide, sodium orthophenylphenoxide, sodium pentachlorophenate, sodium pentachlorophenoxide, sodium polysulfide, sodium silicofluoride, sodium tetrathiocarbonate, sodium thiocyanate, solan, sophamide, spidoxamat, spinetoram, spinosad, spirobudifen, spirodiclofen, spiromesifen, spiropidion, spirotetramat, spiroxamine, stirofos, streptomycin, strychnine, sulcatol, sulcofuron, sulcotrione, sulfallate, sulfentrazone, sulfiflumin, sulfiram, sulfluramid, sulfodiazole, sulfometuron, sulfosate, sulfosulfuron, sulfotep, sulfotepp, sulfoxaflor, sulfoxamyl, sulfoxide, sulfoxime, sulfur, sulfuric acid, sulfuryl fluoride, sulglycapin, sulphosate, sulprofos, sultropen, swep, toz -fluvalinate, tavron, tazimcarb, TBTO, TBZ, TCA, TCBA, TCMTB, TCNB, TDE, tebuconazole, tebufenozide, tebufenpyrad, tebufloquin, tebupirimfos, tebutam, tebuthiuron, tecloftalam, tecnazene, tecoram, tedion, teflubenzuron, tefluthrin, tefuryltrione, tembotrione, temefos, temephos, tepa, TEPP, tepraloxydim, teproloxydim, terallethrin, terbacil, terbucarb, terbuchlor, terbufos, terbumeton, terbuthylazine, terbutol, terbutryn, terbutryne, terraclor, terramicin, terramycin, tetcyclacis, tetflupyrolimet, tetrachlorantraniliprole, tetrachloroethane, tetrachlorvinphos, tetraconazole, tetradifon, tetradisul, tetrafluron, tetramethrin, tetramethylfluthrin, tetramine, tetranactin, tetraniliprole, tetrapion, tetrasul, thallium sulfate, thallous sulfate, thenylchlor, theta- cypermethrin, thiabendazole, thiacloprid, thiadiazine, thiadifluor, thiamethoxam, thiameturon, thiapronil, thiazafluron, thiazfluron, thiazone, thiazopyr, thicrofos, thicyofen, thidiazimin, thidiazuron, thiencarbazone, thifensulfuron, thifluzamide, thimerosal, thimet, thiobencarb, thiocarboxime, thiochlorfenphim, thiochlorphenphime, thiocyanatodinitrobenzenes, thiocyclam, thiodan, thiodiazole-copper, thiodicarb, thiofanocarb, thiofanox, thiofluoximate, thiohempa, thiomersal, thiometon, thionazin, thiophanate, thiophanate-ethyl, thiophanate- methyl, thiophos, thioquinox, thiosemicarbazide, thiosultap, thiotepa, thioxamyl, thiram, thiuram, thuringiensin, tiabendazole, tiadinil, tiafenacil, tiaojiean, tiapyrachlor, TIB A, tifatol, tigolaner, tiocarbazil, tioclorim, tiorantraniliprole, tioxazafen, tioxymid, tirpate, TMTD, tolclofos-methyl, tolfenpyrad, tolprocarb, tolpyralate, tolyfluanid, tolylfluanid, tolylmercury acetate, tomarin, topramezone, toxaphene, TPN, tralkoxydim, tralocythrin, tralomethrin, tralopyril, transfluthrin, transpermethrin, tretamine, triacontanol, triadimefon, triadimenol, triafamone, triallate, tri-allate, triamiphos, triapenthenol, triarathene, triarimol, triasulfuron,triazamate, triazbutil, triaziflam, triazophos, triazothion, triazoxide, tribasic copper chloride, tribasic copper sulfate, tribenuron, tribufos, tributyltin oxide, tricamba, trichlamide, trichlopyr, trichlorfon, trichlormetaphos-3, trichloronat, tri chi or onate, trichlorotrinitrobenzenes, trichlorphon, triclopyr, triclopyricarb, tricresol, tricyclazole, tricyclohexyltin hydroxide, tridemorph, tridiphane, trietazine, trifenmorph, trifenofos, trifloxystrobin, trifloxysulfuron, trifludimoxazin, trifluenfuronate, triflumezopyrim, triflumizole, triflumuron, trifluralin, triflusulfuron, trifop, trifopsime, triforine, trihydroxytriazine, trimedlure, trimethacarb, trimeturon, trinexapac, triphenyltin, triprene, tripropindan, triptolide, tripyrasulfone, tritac, trithialan, triticonazole, tritosulfuron, trunc-call, tuoyelin, tyclopyrazoflor, umifoxolaner, uniconazole, uniconazole-P, urbacide, uredepa, vadescana, valerate, validamycin, validamycin A, valifenalate, valone, vamidothion, vangard, vaniliprole, vernolate, vinclozolin, vitamin D3, warfarin, xiaochongliulin, xinjunan, xiwojunan, xiwojunzhi, XMC, xylachlor, xylenols, xylylcarb, xymiazole, yishijing, zarilamid, zeatin, zengxiaoan, zengxiaolin, zeta-cypermethrin, zinc naphthenate, zinc phosphide, zinc thiazole, zinc thiozole, zinc tri chlorophenate, zinc trichlorophenoxide, zineb, ziram, zolaprofos, zoocoumarin, zoxamide, zuoanjunzhi, zuocaoan, zuojunzhi, zuomihuanglong, a-chlorohydrin, a-ecdysone, a-multistriatin, a- naphthaleneacetic acids, and P-ecdysone.
[0111] In some preferred aspects, the pesticidal formulation of the present disclosure can contain one or more additional fungicide as pre-mix, or being tank mixed with the one or more additional fungicides, or applied sequentially with the one or more additional fungicides. The additional fungicides may include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, acibenzolar-S-methyl, ametoctradin, aminopyrifen, amisulbrom, antimycin, azaconazole, azoxystrobin, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzovindiflupyr, benzylaminobenzene-sulfonate (BABS) salt, bicarbonates, bifem etstrobin, biphenyl, bismerthiazol, bitertanol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, carvone, chlazafenone, chloroinconazide, chloroneb, chlorothalonil, chlozolinate, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazofamid, cyclobutrifluram, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diammonium ethylenebi s-(dithiocarbamate), dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, difenzoquat ion, diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorphacetate, dodine, dodine free base, edifenphos, enestrobin, enestroburin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, feneptamidoquin, fenfuram, fenhexamid, fenopyramid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, flubeneteram, fludioxonil, flufenoxadiazam, fluindapyr, flumetyl sulforim, flumorph, fluopicolide, fluopyram, fluoroimide, fluoxapiprolin, fluoxastrobin, fluoxytioconazole, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetates, GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate), inpyrfluxam, iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isofetamid, isoflucypram, isoprothiolane, isopyrazam, isotianil, kasugamycin, kasugamycin hydrochloride hydrate, kresoxium-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metam-potassium, metam-sodium, metarylpicoxamid, metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid (fatty acids), orysastrobin, oxadixyl, oxathiapiprolin, oxine-copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercury acetate, phosphonic acid, phthalide, picarbutrazox, picoxystrobin, polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propi conazole, propineb, proquinazid, prothioconazole, pydiflumetofen, pyrametostrobin, pyraoxystrobin, pyraclostrobin, pyraziflumid, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyrisoxazole, pyroquilon, quinoclamine, quinoxyfen, quintozene, seboctylamine, sedaxane, silthiofam, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, fungicidal sulfur derivatives, SYP-Z048, tar oils, tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate- methyl, thiram, tiadinil, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triti conazole, validamycin, valifenalate, valiphenal, vinclozolin, zineb, ziram, zoxamide, (RS)-N-(3,5- dichlorophenyl)-2-(methoxymethyl)-succinimide, 1,2-di chloropropane, 1,3 -di chi oro-1, 1,3,3-tetrafluoroacetone hydrate, 1 -chi oro-2, 4-dinitronaphthalene, l-chloro-2-nitropropane, 2-(2- heptadecyl-2-imidazolin- 1 -yl)ethanol, 2,3 -dihydro-5 -phenyl- 1 ,4-dithi-ine 1 , 1 ,4,4-tetraoxide, 2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-l-enyl)phenyl thiocyanateme, ampropylfos, anilazine, azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox, bentaluron, benzamacril; benzamacril-isobutyl, benzamorf, binapacryl, bi s(m ethylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmium calcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis(3-phenylsalicylate), copper zinc chromate, coumoxystrobin, cufraneb, cupric hydrazinium sulfate, cuprobam, cyclafuramid, cypendazole, cyprofuram, decafentin, dichlobentiazox, dichlone, dichlozoline, diclobutrazol, dimethirimol, dinocton, dinosulfon, dinoterbon, dipymetitrone, dipyrithione, ditalimfos, dodicin, drazoxolon, EBP, enoxastrobin, ESBP, etaconazole, etem, ethirim, fenaminstrobin, fenaminosulf, fenapanil, fenitropan, fenpicoxamid, florylpicoxamid, flufenoxystrobin, fluopimomide, fluotrimazole, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, ICIA0858, ipfentrifluconazole, ipflufenoquin, isopamphos, isovaledione, mandestrobin, mebenil, mecarbinzid, mefentrifluconazole, metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, metyltetraprole, milneb, mucochloric anhydride, myclozolin, A-3,5-dichlorophenyl-succinimide, N-3- nitrophenylitaconimide, natamycin, A-ethylmercurio-4-toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercury dimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride, pyracarbolid, pyrapropoyne, pyridachlometyl, pyridinitril, pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol; quinacetol sulfate, quinazamid, quinconazole, quinofumelin, rabenzazole, salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trichlamide, triclopyricarb, triflumezopyrim, urbacid, and zarilamid.
[0112] In some aspects, the formulations of the present disclosure may include one or more fungicidal active ingredients in addition to the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof. In some aspects, the formulations do not include a fungicidal active ingredient in addition to the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof. In some aspects, the formulations may exclude one or more fungicidal active ingredients specified above. In some aspects, the formulations may include one or morefungicidal active ingredients in addition to the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, but may exclude one or more fungicidal ingredients specified above.2. Adjuvants
[0113] In some aspects, the additive includes an agriculturally acceptable adjuvant. Suitable adjuvants can enhance the biological performance of the formulation. Examples of adjuvants are any agents which promote solubility, stability, defoaming, compatibility of ingredients, and UV light protection of the pesticidal formulation; draft reduction and spray efficiency of the pesticidal formulation; and wetting, spreading, retention, deposition, adhesion, and penetration of the pesticidal formulation. The adjuvant as a component of the formulation refers to built-in adjuvant. Examples of suitable built-in adjuvants include, but not limited to, solvent and emulsifiers that are exemplified in previous context. Exemplary agriculturally acceptable adjuvants include, but are not limited to, solvents, co-solvents, antifreeze agents, antifoam agents, compatibilizing agents, sequestering agents, neutralizing agents and buffers, pH modifiers, corrosion inhibitors, colorants, odorants, penetration aids, wetting agents, spreading agents, dispersing agents, thickening agents, flow aids, anti-caking agents, crystallization inhibitors, antimicrobial agents, crop oil, adhesives (for instance, for use in seed formulations), surfactants, protective colloids, emulsifiers, tackifiers, UV absorbers or stabilizers, and mixtures thereof.
[0114] Exemplary agriculturally acceptable adjuvants include, but are not limited to, crop oil concentrates (e.g., 85% mineral oil + 15% emulsifiers); benzylcocoalkyldimethyl quaternary ammonium salts; nonylphenol ethoxylates; polyalkylene oxide alkyl ethers; blends of petroleum hydrocarbon, alkyl esters, organic acids, and anionic surfactants; C9-C11 alkylpolyglycoside; phosphate alcohol ethoxylates; natural primary alcohol (C12-C16) ethoxylate; di- ec-butylphenol EO-PO block copolymers; polysiloxane-methyl cap; nonylphenol ethoxy late+urea ammonium nitrates; emulsified methylated seed oils; tridecyl alcohol (synthetic) ethoxylates (e.g., 8 EO); tallow amine ethoxylates (e.g., 15 EO); and PEG(400) dioleate-99.
[0115] Exemplary surfactants (e.g., wetting agents, tackifiers, dispersants, emulsifiers) include, but are not limited to: the alkali metal salts, alkaline earth metal salts and ammonium salts of fatty acids or of aromatic sulfonic acids (e.g., lignosulfonic acids, phenolsulfonic acids, naphthalenesulfonic acids, and dibutylnaphthalenesulfonic acid); alkyl- andalkylarylsulfonates; alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates; salts of sulfated hexa-, hepta- and octadecanols; salts of fatty alcohol glycol ethers; condensates of sulfonated naphthalene and its derivatives with formaldehyde; condensates of naphthalene or of the naphthalene sulfonic acids with phenol and formaldehyde; polyoxyethylene octylphenol ether; ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether; alkyl aryl polyether alcohols; isotridecyl alcohol; fatty alcohol / ethylene oxide condensates; ethoxylated castor oil; polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers; lauryl alcohol polyglycol ether acetate; sorbitol esters; lignosulfite waste liquors and proteins; denatured proteins, polysaccharides (e.g., methylcellulose); hydrophobically modified starches; and polyvinyl alcohol, polycarboxylates, polyalkoxylates, polyvinyl amine, polyethyleneimine, polyvinylpyrrolidone, and copolymers thereof.
[0116] Exemplary thickeners include, but are not limited to, polysaccharides (e.g., xanthan gum), organic and inorganic sheet minerals, and mixtures thereof.
[0117] Exemplary antifoam agents include, but are not limited to, silicone emulsions, long- chain alcohols, fatty acids, fatty acid salts, organofluorine compounds, and mixtures thereof.
[0118] Exemplary antimicrobial agents include, but are not limited to, bactericides based on dichlorophen and benzyl alcohol hemiformal; isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones; and mixtures thereof.
[0119] Exemplary antifreeze agents include, but are not limited to ethylene glycol, propylene glycol, urea, glycerol, and mixtures thereof.
[0120] Exemplary colorants include, but are not limited to, the dyes known under the names Rhodamine B, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108, and mixtures thereof.
[0121] Exemplary adhesives include, but are not limited to, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose, and mixtures thereof.3. Carriers
[0122] In some aspects, the additive includes a carrier. In some aspects, the additive includes a liquid or solid carrier. In some aspects, the additive includes an organic or inorganic carrier. Exemplary liquid carriers include, but are not limited to: water; aqueous liquids; petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; fatty acid esters; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, / / -butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like; toluene; xylene; petroleum naphtha; crop oil; acetone; methyl ethyl ketone; cyclohexanone; trichloroethylene; perchloroethylene; ethyl acetate; amyl acetate; butyl acetate; propylene glycol monomethyl ether and diethylene glycol monomethyl ether; methyl alcohol; ethyl alcohol; isopropyl alcohol; amyl alcohol; ethylene glycol; propylene glycol; glycerin; 7V-methyl-2-pyrrolidinone; 'A-dimethyl alkylamides; dimethyl sulfoxide; and liquid fertilizers, as well as mixtures thereof. Exemplary solid carriers include, but are not limited to: silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, pyrophyllite clay, attapulgus clay, kieselguhr, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, and mixtures thereof.
[0123] Exemplary adhesives include, but are not limited to, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose, and mixtures thereof.4. Multifunctional Ingredients
[0124] In some aspects, the additive includes multifunctional ingredients. Multifunctional ingredients are desirable in the field for reasons such as formulation optimization, cost reduction, efficacy boost, and so on. In some preferred aspects, the additive includes long chain alkyl amides. In some more preferred aspects, the additive includes N, N-dimethyldecanamide. Disclosed herein is that the solvent N, N-dimethyldecanamide can be an adjuvant informulations containing the compound of Formula I. The present disclosure provides an unexpected fungicidal formulation comprising a compound of Formula I and N, N- dimethyldecanamide.
[0125] In some aspects, the formulations comprise, in weight percent based on the total weight of the formulation, from about 0.01% to about 99% of N, N-dimethyldecanamide (e.g., about 0.01%, 0.05%, 0.1%, 0.2%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 7.5%, 8%, 9%, 10%, 12.5%, 15%, 17.5%, 20%, 25%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 82.5%, 85%, 87.5%, 90%, 92.5%, or 95% of the compound of Formula I-B), or within any range defined from any two of the forgoing values, such as from about 1% to about 95%, from about 10% to about 60%, from about 20% to about 45%, from about 55% to about 82.5%, or from about 12.5% to about 50% of the N, N- dimethyldecanamide, by weight percent based on the total weight of the formulation.C. Packaging
[0126] In some aspects, the formulation can be in the form of a single package formulation containing the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof. In some aspects, the formulation can be in the form of a single package formulation containing the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, and further including at least one additive. In some aspects, the formulation can be in the form of a multipackage formulation, such as a two-package formulation, wherein one package contains the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, while the other package contains at least one additive. In some aspects of the two-package formulation, the formulation contains the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, and the formulation including at least one additive are mixed before application and then applied simultaneously. In some aspects, the mixing is performed as a tank mix (e.g., the formulations are mixed immediately before or upon dilution with water). In some aspects, the formulation contains the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, and the formulation including at least one additive are not mixed as a tank mix, but rather are applied sequentially (in succession), for example, immediately or within 1 hour, within 2 hours, within 4 hours, within 8 hours, within 16 hours, within 24 hours, within 2 days, or within 3 days, of each other.VI. Methods of Use
[0127] The pesticidal formulations disclosed herein can be applied in any known technique for applying pesticides or fungicides. Exemplary application techniques include, but are not limited to, spraying, atomizing, dusting, sprinkling, spreading, or direct application into water. The method of application can vary depending on the intended purpose. In some aspects, the method of application can be chosen to ensure the finest possible distribution of the formulations disclosed herein.
[0128] In some aspects, the present disclosure provides a method for the control or prevention of fungal attack. This method comprises applying to the soil, plant, roots, foliage, or locus of the fungus, or to a locus in which the infestation is to be prevented with any of the formulations disclosed herein.
[0129] In some aspects, the present disclosure provides a method for the control or prevention of fungal attack on a plant, the method including the steps of applying any of the formulations disclosed herein to at least one of the fungus, a seed, the plant, and an area adjacent to the plant.
[0130] In some aspects, the present disclosure provides a method for the control or prevention of fungal attack on a plant, the method comprising contacting an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, foliage of the plant, and a growth medium adapted to grow a plant or a seed, with any of the formulations disclosed herein.
[0131] In some aspects, the present disclosure provides a method for the control or prevention of fungal attack on a plant, the method including the steps of applying any of the formulations disclosed herein to a growth medium adapted to grow a plant or a seed.
[0132] In some aspects, the present disclosure provides a use of the formulations disclosed herein, for protection of a plant against attack by a phytopathogenic organism or the treatment of a plant infested by a phytopathogenic organism, comprising the application of any of the formulations disclosed herein to soil, a plant, a part of a plant, foliage, and / or roots.
[0133] In some aspects, the formulations disclosed herein are applied to an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, foliage of the plant, and a growth medium adapted to grow a plant or a seed, by spraying (e.g., foliar spraying). In some aspects, the spraying techniques use, for example, water as carrier and spray volume rates of from 2 liters per hectare (L / ha) to 2000 L / ha (e.g., from 10-1000 L / ha or from 50-500 L / ha).In some aspects, the formulations disclosed herein are applied by the low-volume or the ultra- low-volume method, wherein the application is in the form of micro granules. In some aspects, the formulations disclosed herein can be applied as dry formulations (e.g., granules, water dispersible granules (WDG), powders, or dusts).
[0134] In some aspects, fungicidal activity is exhibited by the compounds of the mixture when they are applied directly to the plant or to the locus of the plant at any stage of fungal diseases or before infestation. The effect observed can depend upon the type of fungal pathogen and disease to be controlled, the stage of the fungal disease, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. In some aspects, these and other factors can be adjusted to promote non-selective or selective fungicidal action.
[0135] The formulations and methods disclosed herein can be used to control fungal pathogens or diseases from fungal pathogens in a variety of applications. The formulations and methods disclosed herein can be used for controlling fungal pathogens or diseases from fungal pathogens in areas including, but not limited to, farmland, turfgrass, pastures, grasslands, rangelands, fallow land, rights-of-way, aquatic settings, tree and vine, wildlife management areas, or rangeland. In some aspects, the fungal pathogen or disease is controlled in a row crop. Exemplary crops include, but are not limited to, wheat, barley, triticale, rye, teff, oats, maize, cotton, soy, sorghum, rice, millet, sugarcane and range land (e.g, pasture grasses). In some aspects, the formulations and methods disclosed herein can be used for controlling fungal pathogens or diseases from fungal pathogens in maize, wheat, barley, rice, sorghum, millet, oats, or a combination thereof. In some aspects, the formulations and methods disclosed herein can be used for controlling fungal pathogens or diseases from fungal pathogens in broadleaf crops. In some aspects, the formulations and methods disclosed herein can be used for controlling fungal pathogens or diseases from fungal pathogens in canola, flax, sunflower, soy, or cotton. In some aspects, the formulations and methods disclosed herein can be used to control fungal pathogens or diseases from fungal pathogens in conservation reserve program lands (CRP), trees, vines, grasslands, and grasses grown for seeds. In some aspects, the formulations and methods disclosed herein can be used on lawns (e.g, residential, industrial, and institutional), golf courses, parks, cemeteries, athletic fields, and sod farms.
[0136] The compositions and methods disclosed herein can also be used in crop plants that are resistant to, for instance, herbicides, insecticides, fungicides, pathogens, insects, or combinations thereof. In some aspects, the compositions and methods disclosed herein can be used in crop plants that are resistant to one or more herbicides because of genetic engineering or breeding. In some aspects, the compositions and methods disclosed herein can be used in crop plants that are resistant to one or more pathogens such as plant pathogenic fungi owing to genetic engineering or breeding. In some aspects, the compositions and methods disclosed herein can be used in crop plants that are resistant to attack by insects owing to genetic engineering or breeding. In some aspects, the compositions described herein and other complementary fungicides are applied at the same time, either as a combination composition or as a tank mix, or as sequential applications. The compositions and methods may be used in controlling fungal pathogens or diseases from fungal pathogens in crops possessing agronomic stress tolerance (including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH), pest tolerance (including but not limited to insects, fungi, and pathogens), and crop improvement traits (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture).
[0137] The formulation described herein may be used to control fungal pathogens that may include, but are not limited to:[01.38] On cucurbits: powdery mildew (Erysiphe cichoracearum, Sphaerotheca fuliginea, Podosphaera xanthii), ring spot (Mycosphaerella brassicicola), blackleg (Plenodomus lingam), anthracnose (Colletotrichum higginsianum, Colletotrichum obiculare, Colletotrichum spp., Glomerella lagenarium), gummy stem blight (Mycosphaerella melonis, Didymella bryoniae, Stagonosporopsis cucurbilacearum): Altemaria leaf spot and blight (Alternaria cucumerina, Alternaria alternata f. sp. cucurbitae, Alternaria spp.), Cercospora leaf spot (Cercospora citrullina, Cercospora spp.), Fusarium wilt (Fusarium oxysporum), belly rot (Rhizoctonia solani), Corynespora blight / target spot (Corynespora cassiicola), scab (Cladosporium cucumerinum), Verticillium wilt (Verticillium dahliae, Verticillium albo- atrum), black root rot (Thielaviopsis basicola), blue mold rot (Penicillium spp.), charcoal rot (Macrophomina phaseolina), and crater rot (fruit) (Myrothecium roridum):
[0139] On tomato: powdery mildew (Leveillula taurica), Septoria leaf spot (Septoria lycopersici), white mold (Sclerotinia sclerotiorum, Sclerotinia minor), target spot (Corynespora cassiicola), southern blight (Sclerotium rolfsii), gray mold (Botrytis cinerea), gray leaf spot (Stemphylium spp.), Fusarium wilt, Fusarium crown and root rot (Fusariumoxysporum), anthracnose (Colletotrichum coccodes, Colletotrichum dematium, Colletotrichum gloeosporioides, Glomerella cingulate), Altemaria stem canker and black mold (Alternaria alternata), black root rot (Chalara elegans), Cercospora leaf mold (Cercospora fuligena), charcoal rot (Macrophomina phaseolina), corky root rot (Pyrenochaeta lycopersici), Didymella stem rot (Didymella lycopersici , early blight (Alternaria solani), leaf mold (Passalora fulva, Mycovellosiella fulva), phoma rot (Phoma destructiva), and sour rot (Geotrichum candidum),'
[0140] On leafy vegetables: Cercospora leaf spot (Cercospora longissimi, Cercospora spp.), gray mold / Botrytis rot (Botrytis cinerea), Altemaria leaf spot and blight (Alternaria sonchi, Alternaria spp.), powdery mildew (Erysiphe cichor acearum, Golovinomyces cichor acearum, Uncinula spp.), rust (Puccinia dioicae), Septoria leaf spot (Septoria lactucae, Septoria spp.), southern blight (Sclerotium rolfsii), basal rot (Phoma exigua), Rhizoctonia bottom rot (Rhizoctonia solani), Sclerotinia drop (Sclerotinia minor, Sclerotinia sclerotiorum), and Stemphylium leaf spot (Stemphylium botryosum),'
[0141] On potato: anthracnose or black dot (Colletotrichum coccodes), brown spot and black pit (Alternaria alternata), Cercospora leaf blotch (Cercospora concors), charcoal rot (Macrophomina phaseolina), common rust (Puccinia pittieriana), deforming rust (Aecidium cantensis), early blight (Alternaria solani), Fusarium dry rot and Fusarium wilt (Fusarium spp.), gangrene (Phoma exigua f. sp. foveata), gray mold (Botrytis cinerea), black blight or Phoma leaf spot (Stagonosporopsis andigena, Phoma andigena var. andinai), powdery mildew (Erysiphe cichoracearum), Rhizoctonia canker and black scurf (Rhizoctonia solani), Rosellinia black rot (Rosellinia sppi), Septoria leaf spot (Septoria lycopersici var. malagutil), silver scurf (Helminthosporium solani), skin spot (Polyscytalum pustulans), stem rot (Sclerotium rolfsii), Thecaphora smut (Thecaphora solani), Ulocladium blight (Ulocladium atrum), Verticillium wilt (Verticillium albo-atrum), and white mold (Sclerotinia sclerotiorum),'
[0142] On peppers: southern blight (Sclerotium rolfsii), powdery mildew (Leveillula taurica), anthracnose (Colletotrichum capsici, Colletorichum acutatum, Colletorichum spp.), Cercospora (frogeye) leaf spot (Cercospora capsici, Cercospora spp.), charcoal rot (Macrophomina phaseolina), damping-off and root rot (Rhizoctonia solani), Fusarium stem rot (Fusarium solani), Fusarium wilt (Fusarium oxysporum f. sp. capsici), gray leaf spot (Stemphylium spp.), gray mold (Botrytis cinerea), Verticillium wilt (Verticillium albo-atrum), and white mold (Sclerotinia sclerotiorum),'
[0143] On cole crops: Altemaria leaf spot and blight (Alternaria brassicicola, Alternaria spp.), Anthracnose (Colletotrichum spp.), black leg (Leptosphaeria maculans. Phoma lingam), Cercospora leaf spot (Cercopsora spp.), Fusarium yellows and other diseases (Fusarium spp.), gray mold / Botrytis blight (Botrytis cinerea), powdery mildew (Erysiphe polygoni), Rhizoctonia rot and blight (Rhizoctonia solani), ring spot (Mycosphaerella brassicicola , Sclerotinia rot (Sclerotinia spp.), white leaf spot (Pseudocercosporella capsellae).
[0144] On sugar beets: Alternaria leaf spot (Alternaria alternate, Alternaria brassicae), anthracnose (Colletrotrichum dematium), Aphanomyces root rot (Aphanomyces cochlioides), Cercospora leaf spot Cercospora beticola), charcoal rot (Macrophomina paseaolina), Choanephora rot (Choanephora cucurbitarum), damping-off, black leg, black root, and seedling blight (Aphanomyces cochlioides, Cylindrocladium spp., Fusarium spp., Phoma betae, Pleospora betae, Rhizoctonia solani, Thanatephorus cucumeris), Fusarium yellows (Fusarium oxysporum), leaf gall / beet tumor / crown wart (Physoderma leproides), phoma leaf spot and root rot Phoma betae), cotton root rot (Phymatotrichopsis omnivore), powdery mildew (Erysiphe polygoni, Erysiphe betae), Ramularia leaf spot (Ramularia beticola), Rhizoctonia foliar blight, crown rot, root rot (Rhizoctonia solani), Rhizopus root rot (Rhizopus arrhizus, Rhizopus stolonifera), rust (Uromyces betae), Sclerotinia crown and root rot (Sclerotinia sclerotiorum), seedling rust (Puccini subnitens), southern blight, Sclerotium root rot and stem rot (Sclerotium rolfsii), Stemphylium leaf spot (Stemphylium botryosum), storage rots (Botrytis cinerea, Penicillium spp., Phoma betae), Verticillium wilt (Verticillium albo- atrum) and violet root rot (Helicobasidium brebissonii),'
[0145] On rice: Seedling Diseases - Seedling Blight (Cochliobolus miyabeanus, Curvularia spp., Fusarium spp., Rhizoctonia solani, Sclerotium rolfsii, Athelia rolfsii and others); Seed Box Diseases - Cochliobolus miyabeanus, Gibberella fujikuroi (anam. Fusarium moniliforme), Phoma exigua, Fusarium ssp., Pythium ssp., Rhizopus spp., Tricoderma viride, Rhizoctonia solani, Sclerotium rolfsii,' Foliar Diseases - blast (Magnaporthe grisea), brown spot (Cochliobolus miyabeanus), leaf scald (Monographella albescens, Microdochium oryzae, Rhynchosporium oryzae), narrow brown leaf spot (Sphaerulina oryzina, Cercospora janseana, Cercospora oryzae), stackburn or Alternaria leaf spot (Alternaria padwickii), leaf smut (Eballistra oryzae, Entyloma oryzae), eyespot (Drechslera gigantea), white leaf streak (Mycovellosiella oryzae), collar rot (Phomopsis oryzae-sativae), rusts (Puccinia graminis f. sp. oryzae, Uromyces coronatus), Sheath and Culm Diseases - stem rot (Magnaporthe salvinii, Sclerotium oryzae [synanamorph]), sheath blight (Thanatephorus cucumeris, Rhizoctoniasolani [anamorph]), sheath spot (Waited circinata, Rhizoctonia oryzae [anamorph]), aggregate sheath spot (Thanetephorus cucumeris, Rhizoctonia solani [anamorph]), Waited circinata, Rhizoctonia oryzae [anamorph]), Ceratobasidium oryzae sativae, Rhizoctonia oryzae-sativae [anamorph]), sheath net blotch (Cylindrocladium scoparium), sheath rot (Sarocladium oryzae), crown sheath rot (Gaeumannomyces graminis), Myrothecium blotch (Myrothecium verrucaria), sheath blotch (Pyrenochaeta oryzae ,' Root and Crown Diseases - bakanae (Gibberella fujikuroi, Fusarium moniliforme [anamorph]), root rots (Fusarium spp.); Grain Diseases - false smut (Villosiclava virens), Udbatta (Balansia oryzae-sativae), glume blight (Epicoccum sorghi), black kernel (Cochliobolus lunatus), minute leaf and grain spot (Cochliobolus miyabeanus), red blotch of grains Epicoccum nigrum), ear blight (Cochliobolus miyabeanus, Sphaerulina oryzina, Cochliobolus lunatus, Monographella nivalis, Fusarium spp., Phoma spp., Monographella albescens, Magnaporthe salvinii, Cladosporoium spp., Epicoccum sp., Nigrospora spp.);[01.46] On soybean: Altemaria leaf spot (Alternaria spp.), anthracnose (Colletotrichum truncatum, Colletotrichum dematium f. truncatum, Glomerella glycines), black leaf blight (Arkoola nigra), black root rot (Thielaviopsis basicola, Chalara elegans), brown spot (Septoria glycines, Mycosphaerella usoenskajae), brown stem rot (Phialophora gregata, Cephalosporium gregatum), charcoal rot (Macrophomina phaseolina), Choanephora leaf blight Choanephora infundibulifera, Choanephora trispora), damping-off, stem, root rot and aerial blight Rhizoctonia solani, Thanatephorus cucumeris), Drechslera blight (Drechslera glycines), frogeye leaf spot (Cercospora sojina), Fusarium root rot (Fusarium spp.), Leptosphaerulina leaf spot (Leptosphaerulina trifolii), Mycoleptodiscus root rot (Mycoleptodiscus terrestris), Neocosmospora stem rot (Neocosmospora vasinfecta, Acremonium spp.), Phomopsis seed decay Phomopsis spp.), Phyllosticta leaf spot (Phyllosticta sojaecola), Phymatotrichum root rot, cotton root rot (Phymatotrichopsis omnivora, Phymatotrichum omnivorum), pod and stem blight (Diaporthe phaseolorum, Phomopsis sojae), powdery mildew (Microsphaera diffusa), purple seed stain Cercospora kikuchii), Pyrenochaeta leaf spot (Pyrenochaeta glycines), red crown rot (Cylindrocladium crotalariae, Calonectria crotalariae), red leaf blotch, Dactuliophora leaf spot (Coniothyrium glycines, Dactuliochaeta glycines), rust (Phakopsora pachyrhizi), scab (Spaceloma glycines), Sclerotinia stem rot (Sclerotinia sclerotiorum), Southern blight, Sclerotium blight, damping- off and stem rot (Sclerotium rolfsii, Athelia rolfsii), stem canker (Diaporthe phaseolorum, Diaporthe phaseolorum var. caulivora, Phomopsis phaseoli), Stemphylium leaf blight(Stemphylium botryosum, Pleospora tarda), sudden death syndrome (Fusarium virguliforme, Fusarium solani f. sp. glycines), target spot (Corynespora cassiicola), white mold (Sclerotinia sclerotiorum), yeast spot (Nematospora coryli),'
[0147] On com: Anthracnose (Colletotrichum graminicola, Glomerella tucumanensis), Aspergillus ear and kernel rot (Aspergillus flavus), banded leaf and sheath spot (Rhizoctonia solani, Rhizoctonia microsclerotia , black bundle disease (Acremonium strictum, Cephalosporium acremonium), black kernel rot (Marasmiellus spp.), brown spot, black spot, stalk rot (Physoderma maydis), Cephalosporium kernel rot (Acremonium strictum, Cephalosporium acremonium), charcoal rot (Macrophomina phaseolina), Corticium ear rot (Thanatephorus cucumeris, Corticium sasakii), Curvularia leaf spot (Curvularia spp.), Didymella leaf spot (Didymella exitalis), Diplodia ear rot, stalk rot, leaf spot, leaf streak (Diplodia spp.), dry ear rot, cob, kernel and stalk rot (Nigrospora oryzae), ear rots (Alternaria spp., Aspergillus spp., Botrytis cinerea, Fusarium culmorum, Cunninghamella spp., Curvularia pallescens, Rhizopus spp., Gonatobotrys simplex, Doratomyces stemonitis, Cephalotrichum stemonitis, Pithomyces maydicus, Scopulariopsis brumptii), ergot (Claviceps gigantea), eyespot (Aureobasidium zeae, Kabatiella zeae), Fusarium kernel, root and stalk rot, seed rot, stalk rot, ear rot, and seedling blight (Fusarium spp., Gibberella spp.), gray ear rot (Botryosphaeria zeae, Physalospora zeae), gray leaf spot, Cercospora leaf spot (Cercospora sorghi, Cercospora zeae-maydis), Helminthosporium root rot (Exserohilum pedicellatum, Helminthosporium pedicellatum), Cladosporium rot (Cladosporium spp.), leaf spots (Alternaria alternata, Ascochyta maydis, Ascochyta tritici, Ascochyta zeicola, Bipolaris victoriae, Helminthosporium victoriae, Cochliobolus victoriae, Cochliobolus sativus, Bipolaris sorokiniana, Epicoccum nigrum, Exserohilum prolatum, Drechslera prolata, Graphium penicillioides, Leptosphaeria maydis, Leptothyrium zeae, Ophiosphaerella herpotricha, Paraphaeosphaeria michotii, Phoma spp., Septoria spp.), Northern corn leaf blight (Setosphaeria turcica), white blast, stalk rot, stripe (Exserohilum turcicum, Helminthosporium turcicum), Northern corn leaf spot (Cochliobolus carbonum), Helminthosporium ear rot (Bipolaris zeicola, Helminthosporium carbonum), Penicillium ear rot, blue eye, blue mold (Pennicillium spp.), Phaeocytostroma stalk rot and root rot (Phaeocytostroma ambiguum, Phaeocytosporella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis, Sphaerulina maydis), Physalospora ear rot, Botryosphaeria ear rot (Botryosphaeria festucae, Physalospora zeicola), Pyrenochaeta stalk rot and root rot (Phoma terrestris, Pyrenochaeta terrestris), red kernel disease, ear mold, leaf and seed rot (Epicoccumnigrum), Rhizoctonia ear rot, root rot, stalk rot (Rhizoctonia spp.), root rots (Ahernaria alternata, Cercospora sorghi, Dictochaeta fertilis, Fusarium spp., Gibberella spp., Microdochium bolleyi, Mucor spp., Periconia circinata, Rhizopus arrhizus) Rostratum leaf spot, Helminthosporium leaf disease, ear and stalk rot (Setosphaeria rostrata, Helminthosporium rostratum), rusts (Puccinia spp., Physopella spp.), brown rust of corn (Puccinia polysora), Sclerotium ear rot, Southern blight (Sclerotium rolfsii), seed rot-seedling blight (Bipolaris spp., Helminthosporium spp., Diplodia maydis, Exserohilum spp., Fusarium spp., Gibberella spp., Macrophomina phaseolina, Penicillium spp., Phomopsis spp., Rhizoctonia spp., Sclerotium rolfsii, Spicaria spp.), Selenophoma leaf spot (Selenophoma sp.), sheath rot (Gaeumannomyces graminis), shuck rot (Myrothecium gramineum), silage mold (Monascus spp.), smuts (Ustilago spp., Ustilaginoidea virens, Sphacelotheca reiliana, Sporisorium holci-sorghi), Southern corn leaf blight and stalk rot (Cochliobolus heterostrophus, Bipolaris maydis, Helminthosporium maydis), stalk rots (Cercospora sorghi, Fusarium spp., Nectria haematococca, Mariannaea elegans, Mucor spp., Rhopographus zeae, Spicaria spp.), storage rots (Aspergillus spp., Penicillium spp.), tar spot (Phyllachora maydis, Monographella maydis, Coniothyrium phyllachorae), Trichoderma ear rot and root rot (Trichoderma viride, Trichoderma lignorum, Hypocrea spp), white ear rot, root and stalk rot (Stenocarpella maydis, Diplodia zeae), yellow leaf blight (Ascochyta ischaemi, Phyllosticta maydis, Mycosphaerella zeae-maydis) and Zonate leaf spot (Gloeocercospora sorghi), '
[0148] On barley: Anthracnose (Colletotrichum cereale Manns), barley stripe (Pyrenophora graminea), common root rot, crown rot and seedling blight (Cochliobolus sativus, Fusarium culmorum, Fusarium graminearum), dwarf bunt (Tilletia controversa), ergot (Claviceps purpurea), eyespot (Pseudocercosoporella herpotrichoides), halo spot (Pseudoseptoria donacis), kernel blight (Alternaria spp., Arthrinium arundinis, Cochliobolus sativus, Fusarium spp.), Ascochyta leaf spot (Ascochyta spp.), net blotch (Drechslera teres, Pyrenophora teres), powdery mildew (Erysiphe graminis f.sp. hordei, Blumeria graminis), Rhizoctonia root rot (Rhizoctonia solani), crown rust (Puccinia coronata var. hordei), leaf rust (Puccinia hordei), stem rust (Puccinia graminis), stripe rust / yellow rust (Puccinia striiformis f. sp. hordei), scab / head blight (Fusarium spp.), Septoria speckled leaf blotch (Septoria passerinii, Stagonospora avenae f.sp. triticae), sharp eyespot (Rhizoctonia cerealis), covered smut (Ustilago hordei), false loose smut (Ustilago nigra), loose smut (Ustilago nuda), gray snow mold / Typhula blight (Typhula incarnata, Typhula ishikariensis), pink snow mold / Fusarium patch (Microdochium nivale), Ramularia leaf spot of barley (Ramularia collo-cygni), speckled snow mold (Typhula idahoensis), snow scald / Sclerotinia snow mold (Myriosclerotinia borealis, Sclerotinia borealis), southern blight (Sclerotium rolfsii), spot blotch (Cochliobolus sativus), Stagonospora blotch (Stagonospora avenae f.sp. triticae, Stagonospora nodorum, Septoria nodorum), take-all (Gaeumannomyces graminis var. tritici), tan spot (Pyrenophora tritici-repentis, Pyrenophora trichostoma) and Verticillium wilt (Verticillium dahliae),'
[0149] On wheat: Altemaria leaf blight (Alternaria triticina), anthracnose (Glomerella graminicola, Colletotrichum graminicola), Ascochyta leaf spot (Ascochyta tritici), Aureobasidium decay (Microdochium bolleyi, Aureobasidium bolleyi), black head molds, sooty molds (Alternaria spp., Cladosporium spp., Epicoccum spp., Sporobolomyces spp., Stemphylium spp.), black point, kernel smudge (Alternaria spp., Cochliobolus sativus, Cladosporium spp.), Cephalosporium stripe (Hymenula cerealis, Cephalosporium gramineum), common bunt = stinking smut (Tilletia spp.), common root rot (Cochliobolus sativus, Bipolaris sorokiniana, Helminthosporium sativum), cottony snow mold (Coprinus psychromorbidus), crown rot, foot rot, seedling blight, dryland root rot (Fusarium spp., Gibberella spp.), Dilophospora leaf spot, twist (Dilophospora alopecuri), dwarf bunt (Tilletia controversa), ergot (Claviceps purpurea, Sphacelia segetum), eyespot, foot rot, strawbreaker (Tapesia yallundae, Ramulispora herpotrichoides, Pseudocercosporella herpotrichoides, Tapesia acuformis, Ramulispora acuformis, Pseudocercosporella herpotrichoides var. acuformis), false eyespot (Gibellina cerealis), flag smut (Urocystis agropyri), halo spot (Pseudoseptoria donacis, Selenophoma donacis), karnal bunt, partial bunt (Tilletia indica, Neovossia indica), rusts (Puccinia spp.), Leptosphaeria leaf spot (Phaeosphaeria herpotrichoides, Leptosphaeria herpotrichoides, Stagonospora), loose smut (Ustilago spp.), Microscopica leaf spot (Phaeosphaeria microscopica, Leptosphaeria microscopica), Phoma spot (Phoma spp.), pink snow mold, Fusarium patch (Microdochium nivale, Fusarium nivale, Monographella nivalis), Platyspora leaf spot (Clathrospora pentamera, Platyspora pentamera), powdery mildew (Erysiphe graminis f.sp. tritici, Blumeria graminis, Erysiphe graminis, Oidium monilioides), Rhizoctonia root rot (Rhizoctonia solani, Thanatephorus cucumeris), scab, head blight, Fusarium head blight (FHB) (Fusarium spp., Gibberella spp., Microdochium nivale, Monographella nivalis), Sclerotinia snow mold, snow scald (Myriosclerotinia borealis, Sclerotinia borealis), Sclerotium wilt, Southern blight, Sclerotium base rot (Sclerotium rolfsii, Athelia rolfsii), Septoria blotch (Septoria tritici, Mycosphaerella graminicola), sharp eyespot (Rhizoctonia cerealis, Ceratobasidium cereale), speckled snowmold, gray snow mold, Typhula blight (Typhula spp.), spot blotch (Cochliobolus sativus, Bipolaris sorokiniana, Helminthosporium sativum), Stagonospora blotch (Phaeosphaeria spp., Stagonospora spp., Septaria spp.), storage molds (Aspergillus spp., Penicillium spp.), take-all (Gaeumannomyces graminis), tan spot, yellow leaf spot, red smudge (Pyrenophora tritici- repentis, Drechslera tritici-repentis), tar spot (Phyllachora graminis, Linochora graminis) and wheat blast (Magnaporthe grisea
[0150] On peanut: Alternaria leaf blight and leaf spot (Alternaria spp.), anthracnose (Colletotrichum spp.), Aspergillus crown rot (Aspergillus niger), blackhull (Thielaviopsis basicola), Botrytis blight (Botrytis cinerea), Charcoal rot and Macrophomina leaf spot (Macrophomina phaseolina), Choanephora leaf spot (Choanephora spp.), Collar rot (Lasiodiplodia theobromae), Cylindrocladium black rot and leaf spot (Cylindr ocladium spp., Calonectria spp.), damping-off (Aspergillus spp., Fusarium spp., Rhizoctonia spp., Rhizopus spp.), Drechslera leaf spot (Bipolaris spicifera), Fusarium wilt and peg / root rot (Fusarium spp.), early leaf spot (Cercospora arachidicola), late leaf spot (Phaeoisariopsis personala, Cercosporidium personatum), melanosis (Stemphylium botryosum), Myrothecium leaf blight (Myrothecium roridum), Pepper spot and scorch (Leptosphaerulina crassiasca), Pestalotiopsis leaf spot (Pestalotiopsis arachidis), Phoma leaf blight (Phoma microspore). Phomopsis foliar blight and leaf spot (Phomopsis spp.), Phyllosticta leaf spot (Phyllosticta spp.), Phymatotrichum root rot (Phymatotrichopsis omnivore, Fusarium scirpi), pod rot (Fusarium spp., Rhizoctonia spp.), powdery mildew (Oidium arachidis), Rhizoctonia foliar blight, peg and root rot (Rhizoctonia solani), rust (Puccinia arachidis), scab (Sphaceloma arachidis), Sclerotinia blight (Sclerotinia spp.), stem rot / southern blight (Sclerotium rolfsii), Verticillium wilt (Verticillium spp.), web blotch / net blotch (Phoma arachidicola, Didymosphaeria arachidicola), yellow mold (Aspergiillus spp.), and zonate leaf spot (Cristulariella moricoldy,
[0151] On other grain crops (including but not limited to rye, sorghum, oat, and triticale): Anthracnose (Colletotrichum spp.) black head molds (Alternaria spp., Cladosporium spp., Sporobolomyces spp., Stemphylium spp.), black point (Bipolaris spp., Fusarium spp.), bunt / stinking smut (Tilletia spp.), Cephalosporium stripe (Hymenula cerealis), Common root rot and seedling blight (Bipolaris sorokiniana), winter crown rot (Coprinus psychromorbidus), Dilophospora leaf spot (Dilophospora alopecuri), dwarf bunt (Tilletia controversa), ergot (Claviceps purpurea), Fusarium root rot (Fusarium culmorum), halo spot (Pseudoseptoria donacis), karnal bunt (Neovossia indica), leaf streak (Cercosporidium graminis), Leptosphaeria leaf spot (Phaeosphaeria herpotrichoides), loose smut (Ustilago tritici), pinksnow mold (Fusarium spp.), powdery mildew (Erysiphe spp.), scab (Fusarium graminearum), Septoria leaf blotch and tritici blotch (Septaria spp.), sharp eyespot and Rhizoctonia root rot (Rhizoctonia cerealis), snow mold (Typhula spp.), spot blotch (Bipolaris sorokiniana). glume blotch (Septoria nodorum). stalk / stripe smut (Urocystis occulta), stem rust (Puccinia graminis), eyespot / foot rot (Pseudocercosporella herpotrichoides), stripe rust (Puccinia slriiformis), take-all (Gaeumannomyces graminis), and tan spot (Pyrenophora tritici-repentis).
[0152] On stone and pome fruits: leaf spot (Mycosphaerella cersella, Mycosphaerella pyri,Cercospora rubrolincla), anthracnose (Glomerella cingulata, Glomerella aculala), leaf spot of cherry (Blumeriella jaapii), powdery mildew (Podosphaeria leucotricha, Podosphaeria pannosa), Altemaria rot / black spot (Alternaria alternata, A. gaisen), gummosis (Botryosphaeria spp.), fruit rot (Botrytis cinerea), scab (Venturia inequalis, V. pirinia, V. carpophila, V. nashicola, Venturia spp.), southern blight (Sclerotium rolfsii), black rot (Botryosphaeria oblusa), Altemaria blotch and rot (Alternaria mali, Alternaria spp.), cedar apple rust (Gymnosporangium juniper -virginianae), American hawthorn rust (Gymnosporagium globosum), Japanese pear rust (Gymnosporangium asiaticum), European pear rust (Gymnosporangium sabinae), Kern’s pear rust (Gymnosporangium kernianum), pacific coast pear rust (Gymnosporangium libocedri), Rocky Mountain pear rust (Gymnosporangium nelsoni), bitter rot (Colletotrichum spp.), white rot (Botryosphaeria dolhidea), black rot (Diplodia seriala), sooty blotch and flyspeck (pathogen complex including Dothideomycetes and Sordariomycetes), Fabraea leaf spot (Fabraea maculata, Diplocarpon mespili), brown spot (Stemphylium vesicarium), Brooks fruit spot (Mycosphaerella pomi), Phoma leaf and fruit spot (Phoma spp.), blotch (Phyllosticta solitaria), black pox and blister canker (Ellisembia asterinum), apple ring spot (Botryosphaeria spp.), calyx-end rot (Sclerotinia sclerotioruni), Monilinia leaf blight and brown rot (Monilinia spp.), Marssonina blotch (Diplocarpon mall), blue mold (Penicillium spp.), gray mold (Botrytis cinerea), and canker and wood rot diseases (Neonectria spp., Neofabraea spp., Diaporthe spp., Valsa spp., Botryosphaeria spp., Armilllaria spp., Chondrostereum spp., Schizophylum spp., Stereum spp., Trametes spp.);
[0153] On grapes: black rot (Guignardia bidwellii, Phyllosticta ampelicida), bitter rot (Greeneria uvicola), Eutypa dieback (Eutypa lata), Botryosphaeria dieback and Macrophoma rot (Botryosphaeria spp. Botrytis bunch rot and blight (Botrytis cinerea), Phomopsis cane and leaf spot Phomopsis viticola, Cryptosporella viticola), Rotbrenner (Pseudopezicula tracheiphila, Pseudopeziza tracheiphila), anthracnose (Elsinoe ampelina), rust (Phakopsoraampelopsidis, Phakopsora euvitis), Septoria leaf spot (Seploria ampelina), leaf blight (Pseudocercospora vitis), leaf blotch (Briosia ampelophaga), powdery mildew (Erysiphe necator), white rot (Coniella diplodiella, Pdidiella diplodiella), ripe rot (Colletotrichum spp.), berry rots and molds (Alternaria spp., Cladosporium spp., Botrytis cinerea, Colletotrichum spp., Diplodia spp., Greeneria sp / , Phomopsis spp., Aspergillus spp., Penicillium spp., Rhizopus spp., Fusarium spp., Stemphyilium spp., Ascochyta spp.);
[0154] On strawberries: Septoria hard rot and leaf spot (Septoria spp.), powdery mildew (Sphaerotheca macular is, Podosphaera macularis), anthracnose (Colletotrichum spp.), common leaf spot (Mycosphaerella fragariae), Cercospora leaf spot (Cercospora spp.), leaf rust (Phragmidium potentillae, Frommeella tormentillae), Sclerotinia crown and fruit rot (Sclerotinia sclerotiorum), Alternaria fruit rot and black leaf spot (Alternaria spp.), anther and pistil blight / black root rot / hard brown rot (Rhizoctonia spp.), charcoal rot (Macrophomina phaseolina), Coniothyrium diseases (Coniothyrium fuckelii, Coniella fragariae), Dematophora crown and root rot / white root rot (Rosellinia necatrix), Diplodina rot / leaf and stalk rot (Phoma lycopersici), fruit rots (Aspergillus niger, Cladosporium spp., Penicillium spp.), Byssochlamys rot (Byssochlamys fulva), Fruit blotch (Peronospora potentillae, Sphaeropsis malorum, Sclerotium rolfsii, Schizoparme slraminea . Gray mold leaf blight and dry crown rot (Botrytis cinerea), leaf scorch (Diplocarpon earlianum), Pestalotia fruit rot (Pestalotia sp.), Leaf blight (Phomopsis obscurans), Postharvest rots (Botrytis cinerea, Pichia spp., Saccharomyces spp.), southern blight (Sclerotium rolfsii)
[0155] On bananas: Anthracnose (Colletotrichum musae, Armillaria corn rot (Armillaria mellea, Armillaria tabescens), Black cross (Phyllachora musicola), Black root rot (Rosellinia bunodes), Black Sigatoka (Mycosphaerella fijiensis), Brown blotch (Pestalotiopsis leprogena), Brown spot (Cercospora hayi), Ceratocystis fruit rot (Ceratocystis paradoxa), Cigar-end (Verticillium theobromae, Trachysphaera frucligena), Cladosporium speckle (Cladosporium musae), Corm dry rot (Junghuhnia vincta), Cordana leaf spot (Cordana johnstonii, Cordana musae), Crown rot (Colletotrichum musae, Verticillium theobromae, Fusarium spp., Acremonium spp.), Cylindrocladium root rot (Cylindr ocladium spp.), Deightoniella fruit speckle, damping off, leaf spot and tip rot (Deightoniella torulosa), Diamond spot (Cercospora hayi, Fusarium spp.), Dwarf Cavendish tip rot (Nattrassia mangiferae), Eyespot (Drechslera gigantean), Fruit freckle (Guignardia musae), Fruit rot (Botryosphaeria ribis), Fungal root-rot (Fusarium spp., Rhizoctonia spp.), Fungal scald (Colletotrichum musae), Leaf rust (Uredo musae, Uromyces musae), Leaf speckle (Acrodontium simplex), Leaf spot (Curvulariaeragrostidis., Drechslera musae-sapientum, Leptosphaeria musarum, Pestalotiopsis disseminata), Main stalk rot (Ceratocystis paradoxa), Malayan leaf spot (Haplobasidion musae , Marasmiellus rot (Marasmiellus inoderma), Panama disease (Fusarium oxysporum f. sp. cubense), Peduncle rot (Lasiodiplodia theobromae, Fusarium spp., Verticillium theobromae), Pestalotiopsis leaf spot Pestalotiopsis palmarum), Phaeoseptoria leaf spot (Phaeoseptoria musae), Pitting (Pyricularia grisea), Pseudostem heart rot (Fusarium moniliforme), Root & rhizome rot Cylindr ocarpon musae , Sclerotinia fruit rot (Sclerotinia sclerotiorum), Septoria leaf spot (Septoria eumusae), Sheath rot (Nectria foliicola, Mycosphaerella musicola), Sooty mold (Limacinula tenuis), Speckle (Mycosphaerella musae), Black end disease (Nigrospora sphaerica), Stem-end rot (Colletotrichum musae), Tropical speckle (Ramichloridium musae), Verticillium tip rot (Verticillium theobromae), and Yellow Sigatoka (Mycosphaerella musicola .
[0156] On turfgrasses: Anthracnose (Glomerella graminicola, Colletotrichum graminicola), Ascochyta leaf blight (Ascochyta spp.), Brown and Large patch (Rhizoctonia solani), Brown ring patch (Waitea circinata), Copper spot (Gloeocercospora sorghi), Dead spot (Ophiosphaerella agrostis), Dollar spot (Sclerotinia homoeocarpa), Fairy ring (Agaricus spp., Lepiota spp., Marasmius oreades, Lycoperdon spp., Agrocybe pediades, etc.), Gray leaf spot (Pyricularia grisea , Gray snow mold (Typhula spp.), Leaf spot and Melting out (Drechslera spp., Bipolaris spp. / Leaf and sheath spot Waitea circinata var. zeae, Waitea circinata var. oryzae), Necrotic ring spot (Ophiosphaerella spp.), Pink patch (Limonomyces roseipellis), Pink snow mold (Microdochium nivale), Powdery mildew (Blumeria graminis), Pythium blight (Pythium spp.), Red leaf spot (Drechslera (Pyrenophora) erythrospila). Red thread (Laetisaria fuciformis), Rust diseases (Puccinia spp.), Smut diseases (Ustilago spp.), Spring dead spot (Ophiosphaerella korrae, O. herpotrich, O. narmari), Summer patch (Magnaporthe poae), Take-all patch (Gaeumannomyces graminis), Yellow patch (Rhizoctonia cerealis), and Yellow tuft (Sclerophthora macrospora).
[0157] By way of non-limiting illustration, examples of some aspects of the present disclosure are given below. Parts and percentages are on a per weight basis unless otherwise indicated.Examples
[0158] A list of formulations comprising the compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, were prepared for chemical and physical stability and other typesof tests, as detailed herein below. The compound of Formula I, or an acceptable salt, solvate, or hydrate thereof, included in the studies include the compounds of Formula I and Formula I- B disclosed herein. Compounds of Formula I and Formula I-B were successfully prepared according to the methods disclosed in International Application No. PCT / US2024 / 027678. Compounds of Formula I and Formula I-B are observed to be solid.
[0159] The formulations prepared in the studies include emulsifiable concentrate (EC), soluble liquid (SL), oil-in-water emulsion (EW), microemulsion (ME), capsule suspension (CS), suspension concentrate (SC), oil dispersion (OD), and water dispersible granule (WDG) formulations.[01.60] Compounds of Formula I and Formula I-B can be formulated into any of the emulsifiable concentrate (EC), soluble liquid (SL), oil-in-water emulsion (EW), microemulsion (ME), and capsule suspension (CS) formulations. Solid compounds of Formula I and Formula I-B can be further formulated into suspension concentrate (SC), oil dispersion (OD), and water dispersible granule (WDG) formulations.[01.61] Ingredients used in experiments herein are: Plurafac LF 1300 (purchased from BASF SE, chemical name: Alcohols, Cl 6- 18, ethoxylated propoxylated, CAS no.: 68002-96- 0), Agnique® CSO-25 (purchased from BASF, chemical name: ethoxylated castor oil, CAS no.: 61791-12-6), Aromatic 200ND (purchased from ExxonMobil, chemical name: Solvent naphtha petroleum, Heavy aromatic, naphthalene depleted, CAS no. : 64742-94-5), ATLAS® G-5002L (purchased from Croda, chemical name: Polyalkylene oxide block copolymer, CAS no.: 9038-95-3), Break-thru® S233 (purchased from Evonik, chemical name: polyether modified trisiloxane, CAS no.: 134180-76-0), Hallcomid® M-10 (purchased from Stepan Company, chemical name: N, N-dimethyldecanamide, CAS no.: 14433-76-2), Genagen NBP (purchased from Clariant Corporation, chemical name: 2-Pyrrolidinone, 1 -butyl-, CAS no.: 3470-98-2).
[0162] Premix samples of the compounds of Formula I and Formula I-B with different mixing partners can also be prepared.Example 1
[0163] Unexpected Efficacy Improvements from A Solvent
[0164] Emulsifiable concentrates of the compound of Formula I were prepared with solvents and surfactants. The compound of Formula I was added and dissolved in the solvents listed in Table 1 and then the surfactants were added sequentially under agitation forhomogenization. The resulting samples (Sample 1-4) were found to be transparent, light brown homogeneous solution with acceptable emulsion performance.
[0165] Dynamic surface tension was used to understand how quickly a surfactant migrates to the droplet surface for samples made (as shown in Table 1). To collect a measurement, the instrument produces a small bubble and measures the bubble pressure. The pressure is used to calculate the surface tension via the Young-Laplace equation. The lifetime of the bubble is increased, and the surface tension is measured with respect to that time. Typically, for a spray droplet to be retained on the leaf surface, the dynamic surface tension should be less than 55 mN / m at a measurement time of 50 ms.Table 1. Emulsifiable concentrate (EC) formulations with Compound of Formula I and Surface Tension Measurements
[0166] Surface spreading measurements (as shown in Table 2) were done on emulsifiable concentrates of the compound of Formula I (Samples 1, 3, and 5-7) to obtain relative information of formulation spreading. The spray dilution was dyed using a fluorescent (Rhodamine B) or blue dye. The droplet was applied to the leaf surface using a micropipette. The sample incubated for a relevant time period. Then, the videometer was used to determine the droplet spreading area (the videometer collected an image, and a program calculated the droplet area).Table 2. Emulsifiable concentrate (EC) formulations with Compound of Formula I and Cuticle Penetration Measurements
[0167] As shown in Tables 1 and 2, Hallcomid® M-10 unexpectedly improved the EC formulations of the Compound of Formula I on the surface tension, spreading, and penetration, while a solvent like Aromatic 200ND had negative effects on surface tension and spreading. It was also surprising that Hallcomid® M-10, a recognized solvent, improved the formulation more than typical adjuvants like Break-thru® S233 and PLURAFAC LF 1300 did.Example 2
[0168] Preparation and Study of Solo EC Formulations
[0169] Emulsifiable concentrates of the compound of Formula I were prepared with solvents and surfactants. The compound of Formula I was added and dissolved in the solvents listed in Table 3 and then the surfactants were added sequentially under agitation for homogenization. The resulting samples were found to be transparent, light brown homogeneous solution with acceptable emulsion performance.Table 3. Emulsifiable concentrate (EC) formulations with the Compound of Formula I.
[0170] Samples 1 and 4 were made with the same process, with the difference that in Sample 1, Aromatic 200ND was used instead of Hallcomid® M-10 in Sample 4. Disease control efficacy of Samples 1 and 4 were tested.
[0171] EC formulations (Samples 1 and 4) with the Compound of Formula I were evaluated against Septoria leaf blotch (SEPTTR). The EC formulations were applied onto wheat seedlings using an automated booth sprayer to run-off. All sprayed plants were allowed to air dry prior to further handling. Wheat plants (variety Yuma) were grown in soil-less Metro mix, with seven to 10 plants per pot. Ten-day old seedlings were used for testing. Plants were inoculated 1 day after fungicide treatments. Plants were incubated for 24 h in a dark dew room at 22°C and 100% RH then transferred to a greenhouse at 23°C for disease to develop. Once disease fully expressed on untreated plants, disease severity was assessed on the sprayed first true unifoliate leaves. Percent disease control (%DC) was calculated based on the disease severity ratio between treated and untreated plants as follows: %DC = (l-%disease severity(trt) / %disease severity(untrt))*100, where trt = treated and untrt = untreated.Table 3. Efficacy of EC formulations with the Compound of Formula I against Septoria leaf blotch (SEPTTR).
[0172] EC formulations (Samples 1 and 4) with the Compound of Formula I were evaluated against Septoria leaf blotch (SEPTTR) (results shown in Table 4). The number of applications ranged from 1 to 4 applications and spraying volumes from 150-300 L / ha. The first application was conducted 7 days after the inoculation. Percent disease severity was visually estimated using a 0 to 100% scale where 0 indicated absence of disease and 100 corresponded to 100% disease severity. Percent disease control (%DC) was calculated based on the disease severityratio between treated and untreated plants as follows: %DC = (l-%disease severity(trt) / %disease severity(untrt))*100, where trt = treated and untrt = untreated.Table 4. Efficacy of EC formulations with the Compound of Formula I against Septoria leaf blotch (SEPTTR).
[0173] As shown in Tables 3 and 4, Sample 4, which contains Halcomid® M-10 instead of Aromatic 200ND in Sample 1, showed significantly higher curative performance against SEPPTTR than Sample 1 did.Example 3
[0174] Preparation of Premix EC Formulations
[0175] Examples of EC premix formulations are prepared with the Compound of Formula I and another premix partner compound in the following formulations. The formulations are detailed in Table 5 below.Table 5. Emulsifiable concentrate (EC) formulations with Compounds of Formula I and Compound B.Example 4
[0176] Preparation of Solo Formulations
[0177] Examples of solo formulation are prepared with the Compound of Formula I and Formula I-B in the following formulations.Table 6. Soluble liquid (SL) formulations with Compounds of Formula I and Formula I- B, respectively.Table 7. Oil-in-water emulsion (EW) formulations with Compounds of Formula I and Formula I-B, respectively.Table 8. Microemulsion (ME) formulations with Compounds of Formula I and Formula I-B, respectively.Table 9. Capsule suspension (CS) formulations with Compounds of Formula I and Formula I-B, respectively.Table 10. Suspension concentrate (SC) formulations with Compounds of Formula I andFormula I-B, respectively.Table 11. Oil dispersion (OD) formulations with Compounds of Formula I and Formula I-B, respectively.Table 12. Water dispersible granule (WDG) formulations with Compounds of Formula I and Formula I-B, respectively.Example 5
[0178] Preparation and Study of Solo EC Formulations
[0179] Emulsifiable concentrates of the compound of Formula I were prepared with solvents and surfactants. The compound of Formula I was added and dissolved in the solvents listed in Table 13 and then the surfactants were added sequentially under agitation for homogenization. The resulting samples were found to be transparent, light brown homogeneous solution with acceptable emulsion performance.
[0180] Each sample was split into two sub-samples, placing one sub-sample at -10°C and the other at 54°C for two weeks. Once the two-week storage period had ended, the -10°C and 54°C samples were analyzed for the compound of Formula I content. The results in Tables 13 show the retention of the compound of Formula I after the two-week accelerated storage test.
[0181] Each sample was also observed at -10°C for the cold storage stability and at room temperature for 24 hours for the emulsion stability.Table 13. Emulsifiable concentrate (EC) formulations with the Compound of Formula I.
[0182] Samples 8-15 showed good cold stability and emulsion stability. Furthermore, Samples 8-15 showed very good chemical stability in the two-week accelerated storage test, as shown in Table 13.Example 6
[0183] Preparation and Study of Solo EW Formulations
[0184] Oil-in-water emulsion (EW) Formulations of the compound of Formula I were prepared with ingredients listed in Table 14.Table 14. Oil-in-water emulsion (EW) formulations with the Compound of Formula I.
[0185] Samples 16 and 17 showed good cold stability and emulsion stability.
[0186] Furthermore, Samples 16 and 17 were evaluated against wheat and soybean diseases. Foliar applications were conducted by diluting Sample 16 and 17 into water. The number of applications ranged from 1 to 4 applications and spraying volumes from 150-300 L / ha depending upon the crop and target, at the rate by the compound of Formula I of 75 g ai / ha. Percent disease severity was visually estimated using a 0 to 100% scale where 0 indicatedabsence of disease and 100 corresponded to 100% disease severity. Percent disease control (%DC) was calculated based on the disease severity ratio between treated and untreated plants as follows: %DC = (l-%disease severity(trt) / %disease severity(untrt) )*100, where trt = treated and untrt = untreated. Samples 16 and 17 showed very good efficacies against multiple wheat (SEPTTR, PUCCRT, and PUCCST) and soybean (PHAKPA, CORYCA, MCRSDI, CERCSP, and SEPTGL) diseases.Table 17. Efficacy of EW Formulations of the compound of Formula I against wheat and soybean diseases.Example 7
[0187] Preparation and Study of Technical Concentrates (TKs)
[0188] Technical grade compound of Formula I was dissolved into different solvents to evaluate the solubility of the compound of Formula I. Technical concentrates (TKs) were then made according to Table 16 to evaluate the chemical stability of highly concentrated TKs.
[0189] Each sample then was split into two sub-samples, placing one sub-sample at -10°C and the other at 54°C for two weeks. Once the two-week storage period had ended, the -10°C and 54°C samples were analyzed for the compound of Formula I content.
[0190] The results in Tables 16 showed the retention of the compound of Formula I in respective TKs after the two-week accelerated storage test, which met the industrial requirement for chemical stability.Table 16. Technical concentrates (TKs) of the Compound of Formula I.
[0191] The formulations and methods of the appended claims are not limited in scope by the specific formulations and methods described herein, which are intended as illustrations of a few aspects of the claims and any formulations and methods that are functionally equivalent are intended to fall within the scope of the claims. Various modifications of the formulations and methods in addition to those shown and described herein are intended to fall within the scope of the appended claims. Further, while only certain representative formulations and method steps disclosed herein are specifically described, other combinations of the formulations and method steps also are intended to fall within the scope of the appended claims, even if not specifically recited. Thus, a combination of steps, elements, components, or constituents may be explicitly mentioned herein; however, other combinations of steps, elements, components, and constituents are included, even though not explicitly stated. The term “comprising” and variations thereof as used herein is used synonymously with the term “including” and variations thereof and are open, non-limiting terms. Although the terms “comprising” and “including” have been used herein to describe various aspects, the terms “consisting essentially of’ and “consisting of’ can be used in place of “comprising” and “including” to provide for more specific aspects of the disclosure and are also disclosed. Other than in the examples, or where otherwise noted, all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood to be construed in light of the number of significant digits and ordinary rounding approaches, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims.
Claims
WHAT IS CLAIMED IS:
1. A Fungicidal formulation, comprising:(a) a fungicidal compound of Formula (I):Formula (I) or an acceptable salt, solvate, or hydrate thereof; and(b) an additional component; wherein the additional component is selected from the group consisting of a solvent, a co-solvent, a diluent, an emulsifier, a carrier, a binding agent, microcapsules or microcapsuleforming ingredients, an adjuvant, a built-in adjuvant, a second fungicide, another agricultural chemical, and combinations thereof; and wherein the formulation is in a form selected from the group consisting of emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, microemulsions, suspension concentrates, capsule suspensions, suspo-emulsions, oil dispersions, soluble liquids, powders, granules, water dispersible granules, tablets, briquettes, gels, pastes, and greases.
2. The formulation of any of claims 1, wherein the acceptable salt of the fungicidal compound of Formula (I) is 4-(difluoromethoxy)benzyl 4- (((ethyl(methyl)amino)methylene)amino)-2,5-dimethylbenzoate hydrochloride (Formula I- B):Formula I-B3. The formulation of any of claims 1-2, wherein the formulation is a liquid formulation and wherein the fungicidal compound of Formula (I) or an acceptable salt, solvate, or hydratethereof is present in the liquid formulation at a concentration from 0.006 to 600 gram active ingredient per liter (g ai / L) of the liquid formulation.
4. The formulation of claim 3, wherein the liquid formulation is a soluble liquid concentrate, an aqueous solution, an oil solution, a suspension concentrate, an aqueous suspension, an aqueous dispersion, an aqueous emulsion, an aqueous microemulsion, an aqueous suspo-emulsion, an emulsifiable concentrate, an oil-in-water emulsion, an oil dispersion, an oil microemulsion, an oil suspo-emulsion, or a water-in-oil emulsion.
5. The formulation of claim 4, wherein the liquid formulation is an emulsifiable concentrate or an oil-in-water emulsion.
6. The formulation of claims 4, wherein the liquid formulation comprises a solvent or a co-solvent selected from the group consisting of water, a long chain alkyl amide, a fatty acid morpholin amide, a diamide, an ester amide, an alkylene carbonate, a methylated seed oil, a fatty acid ester, a triglyceride ester, an aprotic glycol diether, a glycol ether acetate, a ketone, a phosphate triester, an aromatic solvent, a paraffinic oil, an alkyl alcohol, an alkyl benzoate, a dibenzoate, an alkyl lactate, an ester solvent, an alkyl pyrrolidone, or a polymeric ether.
7. The formulation of claim 6, wherein the liquid formulation is an emulsifiable concentrate and the solvent is a long chain alkyl amide.
8. The formulation of claim 7, wherein the long chain alkyl amide is N, N- dimethyldecanamide.
9. The formulation of claim 8, wherein N, N-dimethyldecanamide is present in the emulsifiable concentrate at a concentration from 1% to 99%.
10. The formulation of any of claims 1-2, wherein the formulation is a solid formulation, and the fungicidal compound of Formula (I) or an acceptable salt, solvate, or hydrate thereof is present in the solid formulation at a concentration from 0.006 to 850 gram active ingredient per kilogram (g ai / kg) of the solid formulation.
11. The formulation of claim 10, wherein the solid formulation is a water-dispersible granule or a soluble granule.
12. The formulation of claim 1, wherein the formulation is in the form of a concentrate; the additional ingredient is a solvent selected from the group consisting of solvents listed in Table A, and mixtures thereof.
13. The formulation of claim 12, wherein the additional ingredient is a solvent selected from the group consisting of solvents listed in Table A.
14. A method of controlling fungal pathogens or diseases from fungal pathogens on a plant, comprising contacting an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, foliage of the plant, and a growth medium adapted to grow a plant or a seed, with the formulation according to any one of claims 1-11.
15. Use of the formulation according to any one of claims 1-11 in control of fungal pathogens or diseases from fungal pathogens on a plant.