Formulations containing substituted 5-membered ring pesticides and methods of use

Abstract

Disclosed herein are pesticidal formulations comprising a substituted 5-membered ring molecule pesticide for controlling undesirable vegetation. Also disclosed herein are methods of controlling undesirable vegetation, comprising applying to the undesirable vegetation or an area adjacent the undesirable vegetation or applying in soil or water to control the emergence or growth of undesirable vegetation a formulation comprising the substituted 5-membered ring molecule pesticide thereof.

Description

FORMULATIONS CONTAINING SUBSTITUTED 5-MEMBERED RINGMOLECULE PESTICIDES AND METHODS OF USEFIELD

[0001] The present disclosure is directed to pesticidal formulations containing substituted 5-membered ring molecules having pesticidal activity, and methods of using the pesticidal formulations thereof to control undesirable vegetation.BACKGROUND

[0002] Many recurring problems in agriculture involve controlling the growth of undesirable vegetation that can, for instance, negatively affect the growth of desirable vegetation. To help control undesirable vegetation, researchers have produced a variety of herbicidal chemicals effective in controlling such unwanted growth. While these herbicidal chemicals may be used neat, it is typically preferable to incorporate the herbicidal 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 controlling undesirable vegetation; 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 herbicide formulations that are stable, easy to use, and safe.SUMMARY

[0003] Disclosed herein are pesticidal formulations that contain a substituted 5-membered ring molecule as a pesticide to control undesirable vegetation in various locations, such as croplands, lawns, pastures, gardens, and recreational areas. The molecules may include lactams or thiolactams, either of which may be substituted with a hydrogenated or halogenated benzyl group and other groups, such as an amino acid or other derivatives thereof.

[0004] In some aspects, the pesticidal formulation comprises a substituted 5-membered ring molecule pesticide having a structure of Formula (I):Formula (I) wherein:X1and X2are independently selected from the group consisting of O and S;Y is selected from the group consisting of O, NR5, and S;R1is selected from the group consisting of H and F;R2is selected from the group consisting of methyl and cyclopropyl;R3is selected from the group consisting of H, methyl, and methoxy;R4is selected from the group consisting of H, (Ci-Cie)-alkyl, (C3-Cio)-cycloalkyl, (C3-Cie)-alkenyl, (C3-Cie)-alkynyl, (Ci-Cio)-alkyl-aryl, aryl, (Ci-Cio)-alkyl-heteroaryl, heteroaryl, (Ci-Cio)-alkyl-cyano, (Ci-Cie)-haloalkyl, (Ci-Cio)-alkoxy-(Ci-Cio)-alkyl, (Ci- Cio)-alkylthio-(Ci-Cio)-alkyl, (Ci-Cio)-alkyl-sulfonyl-(Ci-Cio)-alkyl, R72R73N, SiR75R76R77, (Ci-Cio)-alkyl-SiR75R76R77, R78R79C=N, (Ci-Cio)-alkyl-C(=0)QR70, aryl-(Ci- Cio)-alkyl-C(=0)QR70, heteroaryl-(Ci-Cio)-alkyl-C(=0)QR70, (C3-Cio)-cycloalkyl-(Ci- Cio)-alkyl-C(=0)QR70, R7°QC(=0)-(Ci-Cio)-alkyl-C(=0)QR71, R7°QC(=0)Q-(Ci-Cio)- alkyl-C(=O)QR71, hydroxy-(Ci-Cio)-alkyl-C(=0)QR70, (Ci-Cio)-alkylthio-(Ci-Cio)-alkyl- C(=O)QR70, and (R8°0)2P(=0)-(Ci-Cio)-alkyl;Q is selected from the group consisting of O, S, and NR71,R70, R71, R72, R73, R74and R80are independently selected from the group consisting of H, (Ci-Cie)-alkyl, aryl, heteroaryl, (Ci-Cie)-alkyl-aryl, and (Ci-Cie)-haloalkyl;R72and R73together form a substituted or unsubstituted ring;R75, R76, and R77are independently selected from the group consisting of (Ci-Cie)- alkyl and aryl;R78and R79are independently selected from the group consisting of (Ci-Cie)-alkyl, (C1-C16)-alkyl-aryl, (Ci-Cie)-haloalkyl, aryl, and heteroaryl;R78and R79together form a substituted or unsubstituted ring; andR5is selected from the group consisting of H, (Ci-Cie)-alkyl, (C3-Cie)-alkenyl, (C3- Cie)-alkynyl, (Ci-Cio)-alkyl-aryl, (Ci-Cio)-alkoxy, (C3-Cio)-alkenyloxy, (C3-Cio)-alkynyloxy,aryl-(Ci-Cio)-alkoxy, heterocyclyl-alkoxy, hydroxy, (Ci-Cio)-alkyl-sulfonyl, (Cs-Cs)- cycloalkyl-sulfonyl, (C3-C8)-cycloalkyl-(Ci-Cio)-alkyl-sulfonyl, aryl-sulfonyl, heteroarylsulfonyl, R72R73N-sulfonyl, (Ci-Cio)-alkoxy-NR74-sulfonyl, and aryl-oxy-sulfonyl, or an agriculturally acceptable N-oxide or salt thereof.

[0005] In some aspects, X1and X2are each O; Y is O; and R1, R2, R3and R4are each the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (II):Formula (II)

[0006] In some aspects, X1and X2are each O; Y is O; R2is methyl; R3is methoxy, and R1and R4are each the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (III):Formula (III)

[0007] In some aspects, X1is S; Y is O; R2and R3are each methyl; and X2, R1and R4are each the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (IV):Formula (IV)

[0008] In some aspects, X1, X2and Y are each O; R1is H; R2and R3are each methyl; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (V):Formula (V)

[0009] In some aspects, X1, X2and Y are each O; R1is H; R2is cyclopropyl; R3is H; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (VI):Formula (VI)

[0010] In some aspects, X1and X2are each O; Y is O; R1is F; R2and R3are each methyl; and R4is the same as disclosed herein above; and the substituted 5-membered ring moleculepesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (VII):Formula (VII)

[0011] In some aspects, X1and X2are each O; Y is O; R1is F; R2is cyclopropyl; R3is H; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (VIII):Formula (VIII)

[0012] In some aspects, X1and X2are each O; Y is O; R1is H; R2is methyl; R3is methoxy; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (IX):Formula (IX)

[0013] In some aspects, X1and X2are each O; Y is O; R1is F; R2is methyl; R3is methoxy; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (X):

[0014] In some aspects, X1is S; Y is O; and X2, R1, R2, R3and R4are each the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (XI):Formula (XI)

[0015] In some aspects, X1and X2are independently S; Y is O; and R1, R2, R3and R4are each the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (XII):Formula (XII)

[0016] Applicants have found that various substituted 5-membered ring molecules, such as lactam-based or thiolactam-based molecules, disclosed in the present disclosure exhibit pesticidal activity against various key species of undesirable vegetation.

[0017] In some aspects, the pesticidal formulation of the substituted 5-membered ring molecule pesticides 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. In some aspects, the formulation can be provided as a herbicidal concentrate. In some aspects, the formulation can be provided as a ready -to-use composition.

[0018] In some aspects, the formulation can further comprise an agriculturally acceptable adjuvant or carrier, a herbicidal safener, an additional pesticide, or combinations thereof.

[0019] Also disclosed herein are methods of controlling undesirable vegetation, comprising applying to the undesirable vegetation or to an area adjacent the the undesirable vegetation, or to soil or water prior to the emergence or growth of the undesirable vegetation, a pesticidal formulation comprising any of the substituted 5-membered ring molecule pesticides disclosed herein above. In some aspects, the formulation is applied pre-emergence of the undesirable vegetation. In some aspects, the formulation is applied post-emergence of the undesirable vegetation. In some aspects, the undesirable vegetation is in croplands, lawns, pastures, gardens, and recreational areas. In some aspects, the undesirable vegetation is in row crops. In some aspects, the undesirable vegetation is in maize, soy, canola, cotton, pulses, sunflower, flax, sugar beets, wheat, barley, rice, sorghum, millet, oats, or cereals. In some aspects, the undesirable vegetation is in broadleaf crops. In some aspects, the undesirable vegetation is in canola, flax, sunflower, soy, or cotton.

[0020] In some aspects, the pesticidal formulation is applied in any known technique for applying herbicides. 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 of application can be chosen to ensure the finest possible distribution of the compositions disclosed herein.

[0021] In some aspects, the pesticidal formulation comprising the substituted 5-membered ring molecule pesticide is 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 comprising the substituted 5-membered ring molecule pesticide is 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.

[0022] 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.BRIEF DESCRIPTION OF THE DRAWINGS

[0023] FIG. 1 shows the physical stability of the test oil-in-water formulations EW-1 (Compound A) and EW-2 (Compound B) prepared with TEHP solvent as freshly prepared and after storage at 54 °C for two weeks, as indicated by the particle size changes before and after storage.DETAILED DESCRIPTION

[0024] The present disclosure includes pesticidal formulations comprising substituted 5- membered ring molecules as pesticides to control undesirable vegetation in various locations, such as croplands, lawns, pastures, gardens, and recreational areas. These substituted 5- membered ring molecule pesticides, such as lactams or thio-lactams based molecules, may be substituted with fluorinated benzyl groups and other groups, such as amino acid groups or derivatives thereof. The present disclosure also includes methods for using the pesticidal formulations comprising the substituted 5-membered ring molecule pesticides for controlling undesirable vegetation. In some aspects, the undesirable vegetation is in row crops. In some aspects, the undesirable vegetation is in maize, soy, canola, cotton, pulses, sunflower, sugar beet, wheat, barley, rice, sorghum, millet, oats, flax or cereals. In some aspects, the substituted 5-membered ring molecules are graminicides used to control undesirable vegetation including grass-type species.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 beconstrued 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 illuminate the invention and does not pose a limitation on the scope of the invention unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention.

[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 virus. Pesticides are understood to encompass naturally occurring orsynthetic herbicides, fungicides, insecticides, insect growth regulators, acaricides (miticides), molluscicides, nematicides, ectoparasiticides, or bactericides. The terms “pesticide” and “pesticidal active ingredient” as used herein include herbicides and herbicidal active ingredients.

[0028] As used herein, the terms “herbicide,” “herbicidal chemical,” and “herbicidal active ingredient” may be understood to include an active ingredient that kills, controls, or otherwise adversely modifies the growth of vegetation, particularly undesirable vegetation such as weed species, 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 “herbicidal formulation”.

[0030] As used herein, the terms “herbicidal formulation” or “formulation” may be understood to include compositions that comprise at least one herbicide 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 herbicide or another agricultural chemical, such as 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 herbicidal 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 undesirable vegetation or locus thereof.

[0032] As used herein, the term “adjuvant” may be understood to include additives to the formulation or tank mix that, while having no herbicidal effect in themselves, help to stabilize, improve, or otherwise enhance the herbicidal effect of the herbicidal active ingredient. For example, adjuvants may be surfactants that enhance the absorption of the herbicidal active ingredient into the plant. Adjuvants may be added to the formulation, or adjuvants may be added to the herbicide tank mix by the end user prior to application of the tank mix. Adjuvantsmay also be included in the herbicide formulation, in which case the adjuvant may be referred to as a “built-in adjuvant.”

[0033] As used herein, the term “herbicidal effect” may be understood to include an adversely modifying effect of an active ingredient (e.g., a herbicide) on vegetation, including, for example, a deviation from natural growth or development, killing, regulation, desiccation, growth inhibition, growth reduction, and retardation. The term "herbicidal activity" refers generally to herbicidal effects of an active ingredient. As used herein, the terms “control,” “prevent,” “reduce,” or similar terms such as “controlling,” “preventing,” or “reducing” may be understood by a person of ordinary skill to include herbicide or herbicidal formulation that shows a herbicidal effect or adversely modifies the competitive capability of the weed with respect to a crop; however, it should be understood that ’’controlling,” “preventing,” or “reducing” does not imply complete or 100% control of the undesirable vegetation.

[0034] As used herein, the term "applying" a herbicide or herbicidal formulation refers to delivering the herbicide or herbicidal formulation directly to the targeted vegetation or to the locus thereof or to the area where control of undesirable vegetation is desired. Methods of application include, but are not limited to, pre-emergently contacting soil or water, postern ergently contacting the undesirable vegetation, or contacting the area adjacent to the undesirable vegetation.

[0035] 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.

[0036] 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, herbicides or herbicidal compositions have zero or minimal herbicidal effect on crops.

[0037] As used herein, the term "undesirable vegetation" refers to vegetation that is not wanted in a given area, for instance, weed species. Herbicides or herbicidal formulations are used to control the undesirable vegetation. Preferably, herbicides or herbicidal formulations have a large or complete herbicidal effect on undesirable vegetation.

[0038] As used herein, the terms "active ingredient" or "ai" may be understood to include a chemical compound or composition that has an effect on vegetation, for example, a herbicidal effect or a safening effect on the vegetation. The term “active ingredient” or “ai” may also be used in expressions relating concentrations or applications 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, hydrates, etc.

[0039] 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, 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, hydrates, etc.

[0040] 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.

[0041] As used herein, “agriculturally acceptable N-oxides and salts” may be understood to include N-oxides and salts that exhibit herbicidal activity, or that are or can be converted in plants, water, or soil to the referenced herbicide.

[0042] As used herein, the term “herbicide resistance” refers to an inherited ability of an individual plant to survive an herbicide application that would kill a normal population of the same species of plant. Herbicide resistance in a plant species often arises due to the application of an herbicide on plants of that species in a specific location.

[0043] As used herein, the term “herbicide tolerance” refers to the inherent ability of a species of plants to survive and reproduce after herbicide treatment at a normal use rate. Herbicide tolerance is therefore a natural tolerance within the normal population of the plant species, rather than resistance selected for in that species by the application of an herbicide.

[0044] As used herein, the terms “formulation” or “composition” refer to a mixture comprising at least one herbicide, 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.

[0045] As used herein, the term “locus”, refers to the area in which the vegetation or plants are growing or will grow, typically a field.

[0046] 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).

[0047] 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.

[0048] 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.

[0049] 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- 1 -propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2- pentenyl, 3 -pentenyl, 4-pentenyl, 1 -methyl- 1-butenyl, 2-methyl-l-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 -CEUCH2; 1 -propenyl refers to a group with the structure-CEUCH-CEE; and 2- propenyl refers to a group with the structure -CH2-CEUCH2.

[0050] 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.

[0051] 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.

[0052] 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-fhioroethoxy, 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.

[0053] 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-methylbutylthio, 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.

[0054] 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-tri chloroethylthio, pentafluoroethylthio, and 1,1,1- trifluoroprop-2-ylthio.

[0055] 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.

[0056] 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).

[0057] As used herein, “alkoxycarbonyl” refers to a group of the formula ' OR wherein R is alkyl.

[0058] 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.

[0059] As used herein, “alkylamino” refers to an amino group substituted with one or two alkyl groups, which may be the same or different.

[0060] As used herein, “haloalkylamino” refers to an alkylamino group wherein the alkyl carbon atoms are substituted partially or entirely with halogen atoms.

[0061] 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.

[0062] As used herein, “alkylcarbamyl” refers to a carbamyl group substituted on the nitrogen with an alkyl group.OII— S-RII

[0063] As used herein, “alkyl-sulfonyl” refers to a group of the formula O , where R is alkyl.

[0064] As used herein, “carbamyl” (also referred to as carbamoyl and aminocarbonyl) o refers to a group of the formulao i i — P- OR

[0065] As used herein, “dialkylphosphonyl” refers to a group of the formula OR where R is independently alkyl in each occurrence.

[0066] As used herein, “Ci-Ce trialkylsilyl” refers to a group of the formula -SiR? wherein each R is independently a Ci-Ce alkyl group (the group contains a total of 3 to 18 carbon atoms).

[0067] As used herein, “Me” refers to a methyl group; “OMe” refers to a methoxy group; and “i-Pr” refers to an isopropyl group.

[0068] As used herein, the term “halogen” including derivative terms such as halo refers to fluorine, chlorine, bromine and iodine.

[0069] As used herein, the term “agriculturally acceptable esters” refers to esters that exhibit herbicidal activity or that are or can be converted in plants, water, or soil to the referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can by hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.II. Substituted 5-membered ring molecule pesticides

[0070] Formulations and methods of the present disclosure include pesticidal formulations comprising a substituted 5-membered ring molecule pesticide, such as a substituted lactam- molecule or thiolactam-molecule that may be used as a pesticide, to control undesirable vegetation in various locations, such as croplands, lawns, pastures, gardens, and recreational areas. The substituted 5-membered ring molecule pesticide include molecules that are substituted with fluorinated benzyl groups and amino acid groups, and derivatives thereof.

[0071] In some aspects, the pesticidal formulation comprises a substituted 5-membered ring molecule pesticide having a structure of Formula (I):Formula (I) wherein:X1and X2are independently selected from the group consisting of O and S;Y is selected from the group consisting of O, NR5, or S;R1is selected from the group consisting of H and F;R2is selected from the group consisting of methyl and cyclopropyl;R3is selected from the group consisting of H, methyl, and methoxy;R4is selected from the group consisting of H, (Ci-Cie)-alkyl, (C3-Cio)-cycloalkyl, (C3- Cie)-alkenyl, (C3-Cie)-alkynyl, (Ci-Cio)-alkyl-aryl, aryl, (Ci-Cio)-alkyl-heteroaryl, heteroaryl, (Ci-Cio)-alkyl-cyano, (Ci-Cie)-haloalkyl, (Ci-Cio)-alkoxy-(Ci-Cio)-alkyl, (Ci-Cio)-alkylthio- (Ci-Cio)-alkyl, (Ci-Cio)-alkyl-sulfonyl-(Ci-Cio)-alkyl, R72R73N, SiR75R76R77, (Ci-Cio)-alkyl- SiR75R76R77, R78R79C=N, (Ci-Cio)-alkyl-C(=0)QR70, aryl-(Ci-Cio)-alkyl-C(=0)QR70, heteroaryl-(Ci-Cio)-alkyl-C(=0)QR70, (C3-Cio)-cycloalkyl-(Ci-Cio)-alkyl-C(=0)QR7°, R7°QC(=0)-(Ci-Cio)-alkyl-C(=0)QR71, R7°QC(=0)Q-(Ci-Cio)-alkyl-C(=0)QR71, hydroxy- (Ci-Cio)-alkyl-C(=0)QR70, (Ci-Cio)-alkylthio-(Ci-Cio)-alkyl-C(=0)QR70, and (R80O)2P(=O)- (Ci-Cio)-alkyl;Q is selected from the group consisting of O, S, and NR71,R70, R71, R72, R73, R74and R80are independently selected from the group consisting of H, (Ci-Cie)-alkyl, aryl, heteroaryl, (Ci-Cie)-alkyl-aryl, and (Ci-Cie)-haloalkyl;R72and R73together form a substituted or unsubstituted ring;R75, R76, and R77are independently selected from the group consisting of (Ci-Cie)-alkyl and aryl;R78and R79are independently selected from the group consisting of (Ci-Cie)-alkyl, (C1- C16)-alkyl-aryl, (Ci-Cie)-haloalkyl, aryl, and heteroaryl;R78and R79together form a substituted or unsubstituted ring; andR5is selected from the group consisting of H, (Ci-Cie)-alkyl, (C3-Cie)-alkenyl, (C3- Cie)-alkynyl, (Ci-Cio)-alkyl-aryl, (Ci-Cio)-alkoxy, (C3-Cio)-alkenyloxy, (C3-Cio)-alkynyloxy, aryl-(Ci-Cio)-alkoxy, heterocyclyl-alkoxy, hydroxy, (Ci-Cio)-alkyl-sulfonyl, (Cs-Cs)- cycloalkyl-sulfonyl, (C3-C8)-cycloalkyl-(Ci-Cio)-alkyl-sulfonyl, aryl-sulfonyl, heteroarylsulfonyl, R72R73N-sulfonyl, (Ci-Cio)-alkoxy-NR74-sulfonyl, and aryl-oxy-sulfonyl, or an N-oxide or agriculturally acceptable salt thereof.

[0072] In some aspects, X1is O, and the substituted 5-membered ring molecule is a lactam- based molecule which includes, but is not limited to, the substituted 5-membered ring molecule pesticides having structures of Formulas (II), (III), and (V)-(X) disclosed herein below and elsewhere in the present disclosure.

[0073] In some aspects, X1is S, and the substituted 5-membered ring molecule is a thiolactam-based molecule which includes, but is not limited to, the substituted 5-membered ring molecule pesticides having structures of Formulas (IV), (XI) and (XII) disclosed herein below and elsewhere in the present disclosure.

[0074] In some aspects, X1and X2are each O; Y is O; and R1, R2, R3and R4are each the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (II):Formula (II)

[0075] In some aspects, X1and X2are each O; Y is O; R2is methyl; R3is methoxy, and R1and R4are each the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide of Formula (I) disclosed herein above has a structure of Formula (III):Formula (III)

[0076] In some aspects, X1is S; Y is O; R2and R3are each methyl; and X2, R1and R4are each the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide of Formula (I) disclosed herein above has a structure of Formula (IV):Formula (IV)

[0077] In some aspects, X1and X2are each O; Y is O; R1is H; R2and R3are each methyl; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide of Formula (I) disclosed herein above has a structure of Formula (V):Formula (V)

[0078] In some aspects, X1and X2are each O; Y is O; R1is H; R2is cyclopropyl; R3is H; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide of Formula (I) disclosed herein above has a structure of Formula (VI):Formula (VI)

[0079] In some aspects, X1and X2are each O; Y is O; R1is F; R2and R3are each methyl; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide of Formula (I) disclosed herein above has a structure of Formula (VII):Formula (VII)

[0080] In some aspects, X1and X2are each O; Y is O; R1is F; R2is cyclopropyl; R3is H; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide of Formula (I) disclosed herein above has a structure of Formula (VIII):Formula (VIII)

[0081] In some aspects, X1and X2are each O; Y is O; R1is H; R2is methyl; R3is methoxy; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide of Formula (I) disclosed herein above has a structure of Formula (IX):Formula (IX)

[0082] In some aspects, X1and X2are each O; Y is O; R1is F; R2is methyl; R3is methoxy; and R4is the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide of Formula (I) disclosed herein above has a structure of Formula (X):Formula (X)

[0083] In some aspects, X1is S; Y is O; and X2, R1, R2, R3and R4are each the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (XI):Formula (XI)

[0084] In some aspects, X1and X2are each S; Y is O; and R1, R2, R3and R4are each the same as disclosed herein above; and the substituted 5-membered ring molecule pesticide having a structure of Formula (I) disclosed herein above has a structure of Formula (XII):Formula (XII)

[0085] In some aspects, the substituted 5-membered ring molecule pesticides include the molecules of Compound A to Compound Q listed in Table 1 disclosed herein below.

[0086] In some aspects, the pesticidal formulation comprises a substituted 5-membered ring molecule pesticide selected from the group consisting of the molecules listed below in Table 1 as Compound A to Compound Q.Table 1 : Exemplary Substituted 5-Membered Ring Molecule Pesticides

[0087] The substituted 5-membered ring molecule pesticides of the present disclosure can exist in specific chiral forms, as shown in the molecular structures shown herein above. The substituted 5-membered ring molecules may also exist in different geometric or optical isomeric forms at other locations within each molecule. It will be appreciated by those skilled in the art, with the benefit of this disclosure, that one stereoisomer may be more active than the other stereoisomers. Individual stereoisomers may be obtained by known selective synthetic procedures, by conventional synthetic procedures using resolved starting materials, or by conventional resolution procedures, using the procedures and compositions disclosed herein. This disclosure covers all such chiral forms, isomers, and mixtures thereof, in all proportions.

[0088] In some aspects, the pesticidal formulation can comprise a substituted 5-membered ring molecule pesticides selected from the group consisting of Compound PYR-1 to Compound PYR-21 disclosed in Table 2 below and all stereoisomers thereof.Table 2: Examples of Additional Substituted 5-Membered Ring molecule Pesticides (PYR)

[0089] Some of the substituted 5-membered ring molecule pesticides disclosed herein above are in a liquid form, such as Compounds A-D, I, K, M, P, Q, PYR-3, PYR-5, PYR-17, PYR-18, and PYR-20, which are viscous liquids. Some of the substituted 5-membered ring molecule pesticides disclosed herein above are in a solid form, such as Compounds E-H, J, L, O, PYR-1, PYR-4, PYR-6, PYR-9, PYR-15, PYR-16, PYR-19 and PYR-21, which are solids or powders.

[0090] The substituted 5-membered ring molecule pesticides of the present disclosure can be applied to undesirable vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of undesirable vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, the substituted 5-membered ring molecule pesticide is applied to undesirable vegetation or an area adjacent the undesirable vegetation or applied to soil or water to prevent the emergence or growth of the undesirable vegetation in an amount of 0.1 grams acid equivalent per hectare (g ae / ha) or greater, such as 0.2 g ae / ha or greater, 0.3 g ae / ha or greater, 0.4 g ae / ha or greater, 0.5 g ae / ha or greater, 0.6 g ae / ha or greater, 0.7 g ae / ha or greater, 0.8 g ae / ha or greater, 0.9 g ae / ha or greater, 1 g ae / ha or greater, 1.1 g ae / ha or greater, 1.2 g ae / ha or greater, 1.3 g ae / ha or greater, 1.4 g ae / ha or greater, 1.5 g ae / ha or greater, 1.6 g ae / ha or greater, 1.7 g ae / ha or greater, 1.8 g ae / ha or greater, 1.9 g ae / ha or greater, 2 g ae / ha or greater, 2.25 g ae / ha or greater, 2.5 g ae / ha or greater, 2.75 g ae / ha or greater, 3 g ae / ha or greater, 4 g ae / ha or greater, 5 g ae / ha or greater, 6 g ae / ha or greater, 7 g ae / ha or greater, 8 g ae / ha or greater, 9 g ae / ha or greater, 10 g ae / ha or greater, 11 g ae / ha or greater, 12 g ae / ha or greater, 13 g ae / ha or greater, 14 g ae / ha or greater, 15 g ae / ha or greater, 16 g ae / ha or greater, 17 g ae / ha or greater, 18 g ae / ha or greater, 19 g ae / ha or greater, 20 g ae / ha or greater, 22 g ae / ha or greater, 24 g ae / ha or greater, 25 g ae / ha or greater, 26 g ae / ha or greater, 28 g ae / ha or greater, 30 g ae / ha or greater, 32 g ae / ha or greater, 34 g ae / ha or greater, 35 g ae / ha or greater, 36 g ae / ha or greater, 38 g ae / ha or greater, 40 g ae / ha or greater, 42.5 g ae / ha or greater, 45 g ae / ha or greater, 47.5 g ae / ha or greater, 50 g ae / ha or greater, 52.5 g ae / ha or greater, 55 g ae / ha or greater, 57.5 g ae / ha or greater, 60 g ae / ha or greater, 65 g ae / ha or greater, 70 g ae / ha or greater, 75 g ae / ha or greater, 80 g ae / ha or greater, 85 g ae / ha or greater, 90 g ae / ha or greater, 95 g ae / ha or greater, 100 g ae / ha or greater, 110 g ae / ha or greater, 120 g ae / ha or greater, 130 g ae / ha or greater, 140 g ae / ha or greater, 150 g ae / ha or greater, 160 g ae / ha or greater, 170 g ae / ha or greater, 180 g ae / ha or greater, 190 g ae / ha or greater, 200 g ae / ha or greater, 210 g ae / ha or greater, 220 g ae / ha or greater, 230 g ae / ha or greater, 240 g ae / ha or greater, 250 g ae / ha or greater, 260 g ae / ha or greater, 270 g ae / ha orgreater, 280 g ae / ha or greater, or 290 g ae / ha or greater; in an amount of 300 g ae / ha or less, such as 290 g ae / ha or less, 280 g ae / ha or less, 270 g ae / ha or less, 260 g ae / ha or less, 250 g ae / ha or less, 240 g ae / ha or less, 230 g ae / ha or less, 220 g ae / ha or less, 210 g ae / ha or less, 200 g ae / ha or less, 190 g ae / ha or less, 180 g ae / ha or less, 170 g ae / ha or less, 160 g ae / ha or less, 150 g ae / ha or less, 140 g ae / ha or less, 130 g ae / ha or less, 120 g ae / ha or less, 110 g ae / ha or less, 100 g ae / ha or less, 95 g ae / ha or less, 90 g ae / ha or less, 85 g ae / ha or less, 80 g ae / ha or less, 75 g ae / ha or less, 70 g ae / ha or less, 65 g ae / ha or less, 60 g ae / ha or less, 57.5 g ae / ha or less, 55 g ae / ha or less, 52.5 g ae / ha or less, 50 g ae / ha or less, 47.5 g ae / ha or less, 45 g ae / ha or less, 42.5 g ae / ha or less, 40 g ae / ha or less, 38 g ae / ha or less, 36 g ae / ha or less, 35 g ae / ha or less, 34 g ae / ha or less, 32 g ae / ha or less, 30 g ae / ha or less, 28 g ae / ha or less, 26 g ae / ha or less, 25 g ae / ha or less, 24 g ae / ha or less, 22 g ae / ha or less, 20 g ae / ha or less, 19 g ae / ha or less, 18 g ae / ha or less, 17 g ae / ha or less, 16 g ae / ha or less, 15 g ae / ha or less, 14 g ae / ha or less, 13 g ae / ha or less, 12 g ae / ha or less, 11 g ae / ha or less, 10 g ae / ha or less, 9 g ae / ha or less, 8 g ae / ha or less, 7 g ae / ha or less, 6 g ae / ha or less, 5 g ae / ha or less, 4 g ae / ha or less, 3 g ae / ha or less, 2.75 g ae / ha or less, 2.5 g ae / ha or less, 2.25 g ae / ha or less, 2 g ae / ha or less, 1.9 g ae / ha or less, 1.8 g ae / ha or less, 1.7 g ae / ha or less, 1.6 g ae / ha or less, 1.5 g ae / ha or less, 1.4 g ae / ha or less, 1.3 g ae / ha or less, 1.2 g ae / ha or less, 1.1 g ae / ha or less, 1 g ae / ha or less, 0.9 g ae / ha or less, 0.8 g ae / ha or less, 0.7 g ae / ha or less, 0.6 g ae / ha or less, 0.5 g ae / ha or less, 0.4 g ae / ha or less, 0.3 g ae / ha or less, or 0.2 g ae / ha or less, or in an amount within any range defined between any pair of the preceding values, such as 0.1-300 g ae / ha, 1-150 g ae / ha, 10-200 g ae / ha, 25-75 g ae / ha, 1.5-26 g ae / ha, or 40-100 g ae / ha.III. Formulations

[0091] The present disclosure includes pesticidal formulations of the substituted 5- membered ring molecule pesticides and methods of use of the pesticidal formulation disclosed herein to control undesirable vegetation.A. Physical States

[0092] In some aspects, the pesticidal formulation of the substituted 5-membered ring molecule pesticides 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- Revi sed-March-2017. pdf) .

[0093] 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.

[0094] 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 one immiscible 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 herbicide may be dissolved or dispersed in the organic liquid droplets dispersed in an oil-in-water emulsion. In another aspect, the herbicide 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 herbicide may be dissolved or dispersed in the water or aqueous liquid droplets dispersed in a water-in-oil emulsion. In another aspect, the herbicide 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 fromconventional 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.

[0095] Formulations comprising the substituted 5-membered ring molecule pesticides of the present disclosure may be emulsifiable concentrates, where the substituted 5-membered ring molecule pesticide 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.

[0096] Suitable organic solvents for forming emulsifiable concentrates of the substituted 5-membered ring molecule pesticides include, but are not limited to: long-chain alkyl amides, such as N,N-dimethylalkyl amide, Agnique® AMD 810 or Agnique AMD 10 (Agnique® is a registered trademark of BASF Corporation, Florham Park, NJ, USA), Hallcomid® M-10 or Hallcomid® M-8-10 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® ME18 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 tri ethyl citrate, or Isobornyl acetate, or ethyl 5-methyl-2-furoate; p-anisaldehyde. Suitable co-solvents for the emulsifiable concentrates of the substituted 5-membered ring molecule pesticides 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 Croda Inc., 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.

[0097] 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 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® G5002L (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 Nouryon 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).

[0098] Suitable antifoam agents include polydimethylsiloxanes emulsified in water, such as Foamaster® UDB (Foamaster® is a registered trademark of BASF Corporation, FlorhamPark, 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.

[0099] 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; 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).

[0100] Formulations comprising the substituted 5-membered ring molecule pesticides of the present disclosure may be oil-in-water emulsions, where the substituted 5-membered ring molecule pesticide 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, cosolvents, 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: l,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 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. 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 C18 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; 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.

[0101] Formulations comprising the substituted 5-membered ring molecule pesticides 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 substituted 5-membered ring molecule pesticide 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.

[0102] 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 herbicides or herbicide 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 herbicide in a water-immiscible organic liquid phase, intended for dilution with water by the end user before use.

[0103] Formulations comprising the substituted 5-membered ring molecule pesticides of the present disclosure may be suspension concentrates comprising a stable suspension of substituted 5-membered ring molecule pesticide 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 Nouryon 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 Nouryon, 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: l,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.

[0104] Formulations comprising the substituted 5-membered ring molecule pesticides of the present disclosure may be capsule suspensions (CS) comprising a stable suspension of microcapsules in a water or aqueous liquid continuous phase. The substituted 5-membered ring molecule pesticide 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 tri styrylphenol ethoxylates, such as Soprophor® FLK. Suitable viscosity modifiers or suspending aides 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: l,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.

[0105] Formulations comprising the substituted 5-membered ring molecule pesticides of the present disclosure may be oil dispersions (OD) comprising a stable suspension of the substituted 5-membered ring molecule pesticide in an organic solvent. The substituted 5-membered ring molecule pesticide 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.

[0106] 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.

[0107] Formulations comprising the substituted 5-membered ring molecule pesticides of the present disclosure may be suspo-emulsions, where the substituted 5-membered ring molecule pesticide 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® AG 1555. 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 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: 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 modifiersinclude 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).

[0108] 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.

[0109] Formulations comprising the substituted 5-membered ring molecule pesticides of the present disclosure may be soluble liquid formulations, where the substituted 5-membered ring molecule pesticide 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 (ME A), 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 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 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 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).

[0110] 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).

[0111] 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.

[0112] Powders are free-flowing, finely divided solid formulations. Dustable powders are free-flowing powders suitable for dusting onto soil, water, or directly upon undesirable vegetation where control of undesirable vegetation 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 true solution 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 forslurry 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 soil, water, or directly upon undesirable vegetation where control of undesirable vegetation is desired.

[0113] 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 soil or water where control of undesirable vegetation is desired.

[0114] Formulations comprising the substituted 5-membered ring molecule pesticides of the present disclosure may be wettable granules including water dispersible granules and soluble granules, where the substituted 5-membered ring molecule pesticide 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), or lactose / 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.

[0115] 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.

[0116] Briquettes are dry formulations in the form of solid blocks, for controlled release of the active ingredient into water.

[0117] 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.

[0118] In some aspects, powders, materials for spreading, or dusts can be prepared by mixing or concomitant grinding of the substituted 5-membered ring molecule pesticide 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 substituted 5-membered ring molecule pesticide and optionally other additives with solid carriers. In some aspects, the granules may be prepared using an extrusion process.

[0119] 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 substituted 5-membered ring molecule pesticide (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 substituted 5- membered ring molecule pesticide), or within any range defined from any two of the forgoingvalues, 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 substituted 5-membered ring molecule pesticide, 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 substituted 5-membered ring molecule pesticide (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 substituted 5-membered ring molecule pesticide), 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 substituted 5- membered ring molecule pesticide. 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 substituted 5-membered ring molecule pesticide (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 substituted 5-membered ring molecule pesticide), 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 substituted 5-membered ring molecule pesticide. 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 undesirable vegetation or the locus of undesirable vegetation can contain from about 0.006 to about 80 g ai / L of the substituted 5-membered ring molecule pesticide (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 substituted 5-membered ring molecule pesticide), or within any range defined from any two of the forgoing values, such as from about 0.01 g ai / Lto 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 substituted 5-membered ring molecule pesticide in the tank mix.B. Additives

[0120] The pesticidal formulations containing the substituted 5-membered ring molecule herbicides 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 substituted 5- membered ring molecule pesticide or agriculturally acceptable N-oxide or salt thereof. In some aspects, the additive is added sequentially. In some aspects, the additive is added simultaneously.1. Other Pesticides

[0121] 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, a arthropodicide, a bactericide, a plant growth regulator, or combinations thereof that are compatible with the formulations of the present disclosure.

[0122] In some aspects, the additive is an additional herbicide. The pesticidal formulation of the present disclosure can contain one or more additional herbicides, being tank mixed with the one or more additional herbicides, or applied sequentially with the one or more additional herbicides. Exemplary additional herbicides include, but are not limited to an acetolactate synthase (ALS) inhibitor, a triazolopyrimidine sulfonamide herbicide (such as florasulam, cloransulam, diclosulam, flumetsulam, metosulam, penoxsulam, or pyroxsulam), an imidazolinone herbicide (such as imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, or imazethapyr), a pyrimidinyl oxybenzoate herbicide (such as bispyribac, pyribenzoxim, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac), a sulfonylaminocarbonyl triazolinone herbicide (such as flucarbazone, propoxycarbazone, thiencarbazone), a sulfonylurea herbicide (such as amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metsulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, propyrisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, triasulfuron, tribenuron, thifensulfuron, trifloxysulfuron, triflusulfuron,tritosulfuron), a synthetic auxin herbicide (such as phenoxy herbicides, benzoic acid herbicides, aryl picolinate herbicides, quinoline carboxylic acid herbicides, pyrimidine carboxylic acid herbicides, benzothiazole herbicides, aminocyclopyrachlor, or benazolin), a phenoxycarboxylic acid herbicide (such as 2,4-D, 2,4-DB2, clomeprop, dichlorprop, mecoprop, MCPA, or MCPB), a benzoic acid herbicide (such as chloramben, dicamba, or TBA), a pyridine carboxylate herbicide (such as aminopyralid, clopyralid, fluroxypyr, florpyrauxifen, halauxifen, indolauxipyr, picloram, or triclopyr), a quinoline carboxylic acid herbicide (such as quinclorac, or quinmerac), an auxin transport inhibitor (such as chlorflurenol, diflufenzopyr, naptalam, or 2,3,5-triiodobenzoic acid (2,3,5-TIBA)), a PPO inhibitor herbicide (such as flufenoximacil), a PDS inhibitor herbicide, glyphosate, glufosinate, a photosystem II (PS II) inhibitor herbicide, a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide, an acetyl CoA carboxylase (ACCase) inhibitor herbicide, a plant growth regulator (PGR), a very long chain fatty acid (VLCFA) synthesis inhibitor herbicide, a microtubule assembly inhibitor (MAI) herbicide, a fatty acid and lipid synthesis inhibitor (FA / LSI) herbicide, a 1 -deoxy -D-xyulose 5-phosphate synthase (DOXP)-inhibiting herbicide (such as broclozone), flusulfinam, a isoxazole herbicide such as icafolin, iptriazopyrid, metproxybicyclone, or an agriculturally acceptable N-oxide, salt or ester thereof, or combinations thereof.

[0123] Exemplary additional herbicides include, but are not limited to: 4-CPA; 4-CPB; 4- CPP; 2;4-D; 2;4-D choline salt; 2,4-D salts, esters and amines; 2,4-DB; 3,4-DA; 3,4-DB; 2,4- DEB; 2,4-DEP; 2,4-DP; 3,4-DP; 2,3,6-TBA; 2,4, 5-T; 2,4,5-TB; acetochlor; acifluorfen; aclonifen; acrolein; alachlor; allidochlor; alloxydim; allyl alcohol; alorac; ametridione; ametryne; amibuzin; amicarbazone; amidosulfuron; aminocyclopyrachlor; 4-aminopicolinic acid based herbicides, such as halauxifen, halauxifen-methyl, florpyrauxifen, and those described in U.S. Patent Nos. 7,314,849 and 7,432,227 to Balko, et al.; aminopyralid; amiprofos-m ethyl; amitrole; ammonium sulfamate; anilofos; anisuron; asulam; atraton; atrazine; azafenidin; azimsulfuron; aziprotryne; barban; BCPC; beflubutamid; benazolin; bencarbazone; benfluralin; benfuresate; bensulide; bensulfuron; benthiocarb; bentazone; benzadox; benzfendizone; benzipram; benzobicyclon; benzofenap; benzofluor; benzoylprop; benzthiazuron; bilanafos; bicyclopyrone; bifenox; bilanafos; bipyrazone; bispyribac; bixlozone; borax; bromacil; bromobonil; bromobutide; bromofenoxim; bromoxynil; brompyrazon; butachlor; butafenacil; butamifos; butenachlor; buthidazole; buthiuron; butralin; butroxydim; buturon; butylate; cacodylic acid; cafenstrole; calcium chlorate; calciumcyanamide; cambendichlor; carbasulam; carbetamide; carboxazole; chlorprocarb; carfentrazone-ethyl; CDEA; CEPC; chlomethoxyfen; chloramben; chloranocryl; chlorazifop; chlorazine; chlorobromuron; chlorbufam; chloreturon; chlorfenac; chlorfenprop; chlorflurazole; chlorflurenol; chloridazon; chlorimuron; chlornitrofen; chloropon; chlorotoluron; chloroxuron; chloroxynil; chlorpropham; chlorsulfuron; chlorthal; chlorthiamid; cinidon-ethyl; cinmethylin; cinosulfuron; cisanilide; clacyfos; clethodim; cliodinate; clodinafop-propargyl; clofop; clomazone; clomeprop; cloprop; cloproxydim; clopyralid; clopyralid-olamine; cloransulam-methyl; CMA; copper sulfate; CPMF; CPPC; credazine; cresol; cumyluron; cyanatryn; cyanazine; cycloate; cyclopyranil; cyclopyrimorate; cyclosulfamuron; cycloxydim; cycluron; cyhalofop-butyl; cyperquat; cyprazine; cyprazole; cypromid; daimuron; dalapon; dazomet; delachlor; desmedipham; desmetryn; di-allate; dicamba; dichlobenil; dichloralurea; dichlormate; dichlorprop; dichlorprop-P; diclofop- methyl; diclosulam; diethamquat; diethatyl; difenopenten; difenoxuron; difenzoquat; diflufenican; diflufenzopyr; dimefuron; dimepiperate; dimethachlor; dimethametryn; dimethenamid; dimethenamid-P; dimexano; dimidazon; dinitramine; dinofenate; dinoprop; dinosam; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; disul; dithiopyr; diuron; DMPA; DNOC; DSMA; EBEP; eglinazine; endothal; epronaz; EPTC; erbon; esprocarb; ethalfluralin; ethametsulfuron; ethbenzamide; ethametsulfuron; ethidimuron; ethiolate; ethobenzamid; ethofumesate; ethoxyfen; ethoxysulfuron; etinofen; etnipromid; etobenzanid; EXD; fenasulam; fenoprop; fenoxaprop; fenoxaprop-P-ethyl; fenoxaprop-P-ethyl + isoxadifen-ethyl; fenoxasulfone; fenquinotrione; fenteracol; fenthiaprop; fentrazamide; fenuron; ferrous sulfate; flamprop; flamprop-M; flazasulfuron; florpyrauxifen; florpyrauxifen-benzyl; florasulam; fluazifop; fluazifop-P -butyl; fluazolate; flucarbazone; flucetosulfuron; fluchloralin; flufenacet; flufenican; flufenpyr-ethyl; flumetsulam; flumezin; flumiclorac-pentyl; flumioxazin; flumipropyn; fluometuron; fluorodifen; fluoroglycofen; fluoromidine; fluoronitrofen; fluothiuron; flupoxam; flupropacil; flupropanate; flupyrsulfuron; fluridone; flurochloridone; fluroxypyr; fluroxypyr-meptyl; flurtamone; fluthiacet; fomesafen; foramsulfuron; fosamine; fumiclorac; furyloxyfen; glufosinate; glufosinate-ammonium; glufosinate-P-ammonium; glyphosate salts and esters; halauxifen; halauxifen-methyl; halosafen; halosulfuron; haloxydine; haloxyfop; hexachloroacetone; hexaflurate; hexazinone; imazamethabenz; imazamox; imazapic; imazapyr; imazaquin; imazethapyr; imazosulfuron; indanofan; indaziflam; indolauxypyr; iodobonil; iodomethane; iodosulfuron; iodosulfuron-ethyl-sodium; iofensulfuron; ioxynil; ipazine; ipfencarbazone; iprymidam; isocarbamid; isocil; isomethiozin; isonoruron; isopolinate; isopropalin; isoproturon; isouron; isoxaben; isoxachlortole;isoxaflutole; isoxapyrifop; karbutilate; ketospiradox; lactofen; lenacil; linuron; MAA; MAMA; MCPA; MCPA esters and amines; MCPA-thioethyl; MCPB; mecoprop; mecoprop-P; medinoterb; mefenacet; mefluidide; mesoprazine; mesosulfuron; mesotrione; metam; metamifop; metamitron; metazachlor; metflurazon; methabenzthiazuron; methalpropalin; methazole; methiobencarb; methiozolin; methiuron; methometon; methoprotryne; methyl bromide; methyl isothiocyanate; methyldymron; metobenzuron; metobromuron; metolachlor; metosulam; metoxuron; metribuzin; metsulfuron; molinate; monalide; monisouron; monochloroacetic acid; monolinuron; monuron; morfamquat; MSMA; naproanilide; napropamide; napropamide-M; naptalam; neburon; nicosulfuron; nipyraclofen; nitralin; nitrofen; nitrofluorfen; norflurazon; noruron; OCH; orbencarb; ortho- chlorobenzene; orthosulfamuron; oryzalin; oxadiargyl; oxadiazon; oxapyrazon; oxasulfuron; oxaziclomefone; oxyfluorfen; paraflufen-ethyl; parafluron; paraquat; pebulate; pelargonic acid; pendimethalin; penoxsulam; pentachlorophenol; pentanochlor; pentoxazone; perfluidone; pethoxamid; phenisopham; phenmedipham; phenmedipham-ethyl; phenobenzuron; phenylmercury acetate; picloram; picolinafen; pinoxaden; piperophos; potassium arsenite; potassium azide; potassium cyanate; pretilachlor; primisulfuron; procyazine; prodiamine; profluazol; profluralin; profoxydim; proglinazine; prohexadione-calcium; prometon; prometryne; pronamide; propachlor; propanil; propaquizafop; propazine; propham; propisochlor; propoxycarbazone; propyrisulfuron; propyzamide; prosulfalin; prosulfocarb; prosulfuron; proxan; prynachlor; pydanon; pyraclonil; pyraflufen; pyrasulfotole; pyrazogyl; pyrazone; pyrazolynate; pyrazosulfuron; pyrazoxyfen; pyribenzoxim; pyributicarb; pyriclor; pyridafol; pyridate; pyriftalid; pyriminobac; pyrimisulfan; pyrithiobac- sodium; pyroxasulfone; pyroxsulam; quinclorac; quinmerac; quinoclamine; quinonamid; quizalofop; quizalofop-P-ethyl; quizalofop-P-tefuryl; rhodethanil; rimsulfuron; saflufenacil; S-metolachlor; sebuthylazine; secbumeton; sethoxydim; siduron; simazine; simeton; simetryn; SMA; sodium arsenite; sodium azide; sodium chlorate; sulcotrione; sulfallate; sulfentrazone; sulfometuron; sulfosate; sulfosulfuron; sulfuric acid; sulglycapin; swep; TCA; tebutam; tebuthiuron; tefuryltrione; tembotrione; tepraloxydim; terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryne; tetrafluron; thenylchlor; thiameturon; thiazafluron; thiazopyr; thidiazimin; thidiazuron; thiencarbazone; thifensulfuron; thiobencarb; tiafenacil; tiocarbazil; tioclorim; tolpyralate; topramezone; tralkoxydim; tri-allate; triafamone; triasulfuron; triaziflam; tribenuron; tribenuron; tricamba; triclopyr choline salt; triclopyr esters and amines; tridiphane; trietazine; trifloxysulfuron; trifludimoxazin; trifluralin; triflusulfuron; trifop; trifopsime; trihydroxytriazine; trimeturon; tripropindan; tritac; tritosulfuron; vernolate; xylachlor; andsalts, esters, optically active isomers, and mixtures thereof. In some aspects, preferred herbicidal active ingredients in addition to the substituted 5-membered ring molecule pesticide include halauxifen, florasulam, penoxsulam, pyroxsulam, clopyralid, florpyrauxifen, triclopyr, cinmethylin, 2,4-D, MCPA, dicamba, glyphosate, glufosinate, agriculturally acceptable N- oxides, salts, or esters thereof, and mixtures thereof.

[0124] In some aspects, the formulations of the present disclosure may include one or more herbicidal active ingredients in addition to the substituted 5-membered ring molecule pesticide. In some aspects, the formulations do not include an herbicidal active ingredient in addition to the substituted 5-membered ring molecule pesticide. In some aspects, the formulations may exclude one or more herbicidal active ingredients specified above. In some aspects, the formulations may include one or more herbicidal active ingredients in addition to the substituted 5-membered ring molecule pesticide, but may exclude one or more herbicidal ingredients specified above.2. Safeners

[0125] In some aspects, the additive is a safener. Safeners are compounds leading to better crop plant compatibility when applied with a herbicide. In some aspects, the safener itself is herbicidally active. In some aspects, the safener acts as an antidote or antagonist in the crop plants and can protect the crop plants from damage that might otherwise occur from an applied herbicide. Exemplary safeners include, but are not limited to, AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet, cloquintocet-mexyl, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, disulfoton, fenchlorazole, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen- ethyl, jiecaowan, jiecaoxi, mefenpyr, mefenpyr-di ethyl, mephenate, naphthalic anhydride, 2,2,5-trimethyl-3-(dichloroacetyl)-l,3-oxazolidine, 4-(dichloroacetyl)-l-oxa-4-azaspiro [4.5]decane, oxabetrinil, R29148, and A-phenyl-sulfonylbenzoic acid amides, as well as thereof agriculturally acceptable salts and, provided they have a carboxyl group, their agriculturally acceptable derivatives.

[0016] In some aspects, the safener can be cloquintocet or an ester or salt or ester thereof, such as cloquintocet-mexyl. In some aspects, the safener can be mefenpyr or an ester or salt thereof, such as mefenpyr-di ethyl. In some aspects, the safener is employed in rice, cereal, or maize. For example, mefenpyr or cloquintocet can be used to antagonize harmful effects of the formulations on rice, row crops, and cereals.

[0127] It is known that when dry formulations, such as powders or granules, contain cloquintocet-mexyl, the cloquintocet-mexyl may readily convert to its hydrate form when the dry formulation is added to water or an aqueous liquid. Cloquintocet-mexyl hydrate tends to form large crystals, which can interfere with effective spraying of the herbicide composition. For this reason, a crystal inhibitor, such as a polycarboxylate, may be added to the dry formulation. A suitable polycarboxylate may be found in such products as Geropon® T-36. Dry formulations, such as powders or granules, can contain cloquintocet acid.3. Adjuvants

[0128] 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 with undesirable vegetation. 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.

[0129] 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; 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.

[0130] 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- and alkylarylsulfonates; 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.

[0131] Exemplary thickeners include, but are not limited to, polysaccharides (e.g., xanthan gum), organic and inorganic sheet minerals, and mixtures thereof.

[0132] Exemplary antifoam agents include, but are not limited to, silicone emulsions, long- chain alcohols, fatty acids, fatty acid salts, organofluorine compounds, and mixtures thereof.

[0133] 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.

[0134] Exemplary antifreeze agents include, but are not limited to ethylene glycol, propylene glycol, urea, glycerol, and mixtures thereof.

[0135] 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.

[0136] Exemplary adhesives include, but are not limited to, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose, and mixtures thereof.4. Carriers

[0137] 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; / ' / .' / ' / -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.C. Packaging

[0138] In some aspects, the formulation can be in the form of a single package formulation containing the substituted 5-membered ring molecule pesticide or an agriculturally acceptable N-oxide, or salt thereof. In some aspects, the formulation can be in the form of a single package formulation containing the substituted 5-membered ring molecule pesticide or an agriculturally acceptable N-oxide or salt thereof and further including at least one additive. In some aspects,the formulation can be in the form of a multi-package formulation, such as a two-package formulation, wherein one package contains the substituted 5-membered ring molecule pesticide or an agriculturally acceptable N-oxide or salt thereof while the other package contains at least one additive. In some aspects of the two-package formulation, the formulation contains the substituted 5-membered ring molecule pesticide or an agriculturally acceptable N-oxide or salt 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 substituted 5-membered ring molecule pesticide or an agriculturally acceptable N-oxide or salt 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

[0139] The pesticidal formulations disclosed herein can be applied in any known technique for applying pesticides or herbicides. 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.

[0140] In some aspects, a method of controlling undesirable vegetation comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation any of the formulations disclosed herein.[014.1 ] The formulations disclosed herein can be applied pre-emergence (before the emergence of undesirable vegetation) or post-emergence (e.g., during or after emergence of the undesirable vegetation). In some aspects, the composition is applied post-emergence to the undesirable vegetation. In some aspects, the composition is applied pre-emergence to the undesirable vegetation.

[0142] When the formulations are used in crops, the formulations can be applied after seeding and before or after the emergence of the crop plants. In some aspects, the formulations disclosed herein show good crop tolerance even when the crop has already emerged and can be applied during or after the emergence of the crop plants. In some aspects, when theformulations are used in crops, the formulations can be applied before seeding of the crop plants. In some aspects, when the formulations are used in crops, the formulations can be applied after seeding but before the emergence of the crop plants.

[0143] In some aspects, the formulations disclosed herein are applied to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation 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, wherein the formulations disclosed herein are less well tolerated by certain crop plants, the formulations can be applied with the aid of the spray apparatus in such a way that they come into little contact, if any, with the leaves of the sensitive crop plants while reaching the leaves of undesirable vegetation that grows underneath or on the bare soil (e.g., post-directed or lay-by). In some aspects, the formulations disclosed herein can be applied as dry formulations (e.g., granules, water dispersible granules (WDG), powders, or dusts).

[0144] In some aspects, wherein the undesirable vegetation is treated post-emergence, the formulations disclosed herein are applied by foliar application. In some aspects, herbicidal 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 growth or before planting or emergence. The effect observed can depend upon the type of undesirable vegetation to be controlled, the stage of growth of the undesirable vegetation, 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 herbicidal action.

[0145] The formulations and methods disclosed herein can be used to control undesirable vegetation in a variety of applications. The formulations and methods disclosed herein can be used for controlling undesirable vegetation 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 undesirable vegetation 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 undesirable vegetation 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 undesirable vegetation in broadleaf crops. In some aspects, the formulations and methods disclosed herein can be used for controlling undesirable vegetation in canola, flax, sunflower, soy, or cotton. In some aspects, the formulations and methods disclosed herein can be used in industrial vegetation management (IVM) or for utility, pipeline, roadside, and railroad rights-of-way applications. In some aspects, the formulations and methods disclosed herein can also be used in forestry (e.g. , for site preparation or for combating undesirable vegetation in plantation forests). In some aspects, the formulations and methods disclosed herein can be used to control undesirable vegetation 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.

[0146] 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. Exemplary resistant crops include, but are not limited to, crops that are resistant to photosystem II inhibitors, or crop plants that, owing to introduction of the gene for Bacillus thuringiensis (or Bl) toxin by genetic modification, are resistant to attack by certain insects. In some aspects, the compositions and methods described herein can be used in conjunction with glyphosate, glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, acetolactate synthase (ALS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, protoporphyrinogen oxidase (PROTOX) inhibitors, triazines, and bromoxynil to control vegetation in crops tolerant to glyphosate, glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates, ACCase inhibitors, imidazolinones, synthetic auxin herbicides, HPPD inhibitors, PROTOX inhibitors, triazines, bromoxynil, orcombinations thereof. In some aspects, the undesirable vegetation is controlled in glyphosate, glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates, ACCase inhibitors, synthetic auxin herbicide, HPPD inhibitors, PROTOX inhibitors, triazines, and bromoxynil tolerant crops possessing single, multiple or stacked traits conferring tolerance to single or multiple chemistries and / or multiple modes of action. In some aspects, the undesirable vegetation can be controlled in a crop that is ACCase-tolerant, ALStolerant, or a combination thereof. In some aspects, the compositions described herein and other complementary herbicides 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 undesirable vegetation 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).

[0147] The formulation described herein may be used to control plant species described, but not limited to, weeds species found in Randall, R.P. (2017). A Global Compendium of Weeds. 3rd Edition. Perth, Western Australia. In some aspects, the compositions disclosed herein can be used for controlling undesirable vegetation including grasses, broadleaf weeds, sedge weeds, and combinations thereof. In some aspects, the compositions disclosed herein can be used for controlling undesirable vegetation including, but not limited to, Acanthospermum species, Aegilops species, Agrostis species, Alopecurus species, Ambrosia species, Anthemis species, Apera species, Amaranthus species, Avena species, Brachiaria species, Bromus species, Chenopodium species, Cenchrus species, Cirsium species, Commelina species, Cyperus species, Datura species, Digitaria species, Echinochloa species, Eleusine species, Atriplex species, Brassica species, Convolvulus species, Conyza species, Cassia species, Euphorbia species, Geranium species, Galinsoga species, Ipomea species, Lamium species, Leptochloa species, Lolium species, Monochoria species, Malva species, Matricaria species, Panicum species, Phalaris species Polygonum species, Prosopis species, Rumex species, Setaria species, Sida species, Sisymbrium species, Solanum species, Sorghum species, Trifolium species, Xanthium species, Veronica species, and Viola species. In some aspects, the undesired vegetation includes blackgrass (Alopecurus myosuroides Huds.), wild oat (Avena fatua), barnyard grass (Echinochloa crus-galli) common chickweed (Stellaria media), velvetleaf (Abutilon theophrasti), hemp sesbania (Sesbania exaltata Cory), Anodacristata, Bidens pilosa, Brassica kaber, shepherd’s purse (Cap sella bursa-pastoris), cornflower (Centaurea cyanus or Cyanus segetum), hempnettle (Galeopsis tetrahit), cleavers (Galium aparine), common sunflower (Helianthus annuus), Desmodium tortuosum, Italian ryegrass (Lolium multiflorum), kochia (Kochia scoparia), Medicago arabica, Mercurialis annua, Myosotis arvensis, common poppy (Papaver rhoeas), Raphanus raphanistrum, broadleaf dock (Rumex obtusifolius), Russian thistle (Salsola kali), wild mustard (Sinapis arvensis), Sonchus arvensis, Thlaspi arvense, Tagetes minuta, Richardia brasiliensis, Plantago major, Plantago lanceolata, bird’seye speedwell (Veronica persica), pigweed (Amaranthus retroflexus), winter rape (Brassica napus), lambsquarters (Chenopodium album), Canadian thistle (Cirsium arvense), nutsedge (Cyperus esculentus), poinsettia (Euphorbia heterophylla), prickly lettuce (Lactuca serriola), purple deadnettle (Lamium purpureum), wild chamomile (Matricaria chamomilla), false chamomile (Matricaria inodora), field chamomile (Anthemis arvensis), common buckwheat (Fagopyrum esculentum), wild buckwheat (Polygonum convulvus), giant foxtail (Setaria faberi), green foxtail (Setaria viridis), yellow foxtail (Setaria pumila) common sorghum (Sorghum vulgare), wild pansy (Viola tricolor), or combinations thereof.

[0148] The compositions described herein can be used to control herbicide resistant or tolerant weeds. The methods employing the compositions described herein may also be employed to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins (e.g., benzoic acids, phenoxycarboxylic acids, pyridine carboxylates, quinoline carboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors (e.g., bipyridyliums, such as paraquat and diquat), 5 -enolpyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, bilanafos), microtubule assembly inhibitors (e.g., benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (e.g., carbamates), very long chain fatty acid (VLCFA) inhibitors (e.g., acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid synthesis inhibitors(e.g., phosphorodithioates, thiocarbamates, benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase (PROTOX) inhibitors e.g., diphenylethers, N- phenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidinediones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS) inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulose biosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac, triazol ocarboxamides), herbicides with multiple modes of action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endothall, and organoarsenicals. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple herbicide modes of action, and biotypes with multiple resistance or tolerance mechanisms (e.g., target site resistance or metabolic resistance).

[0149] 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

[0150] A list of formulations comprising different substituted 5-membered ring molecule pesticides respectively were prepared for chemical and physical stability and other types of tests, as detailed herein below. The substituted 5-membered ring molecule pesticides included in the studies include Compounds A, B, E and F disclosed herein above in Table 1. Compounds A, B, E and F were successfully prepared according to the methods disclosed in International Application No. PCT / US2023 / 076654. Compounds A and B are observed to be viscous liquid, and Compounds E and F are observed to be solid.

[0151] 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.

[0152] All Compounds disclosed herein in Tables 1 and 2 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 substituted 5-membered ring molecule pesticides disclosed herein in Tables 1 and 2 can be further formulated into suspension concentrate (SC), oil dispersion (OD), and water dispersible granule (WDG) formulations.

[0153] Premix samples of the substituted 5-membered ring molecule pesticides with different mixing partners were also successfully prepared. The physical and chemical stabilities of each of the premix samples were tested. The premix samples preparation and test results are detailed herein below.Example 1

[0154] Preparation of Solo F ormulations

[0155] Test samples were each successfully prepared with Compounds A and B (liquid) in the following formulations, respectively: emulsifiable concentrate (EC), soluble liquid (SL), oil-in-water (EW), microemulsion (ME), and capsule suspension (CS) formulations. The formulations are detailed in Tables 3-7 below, respectively.Table 3. Emulsifiable concentrate (EC) formulations with Compounds A and B, respectively.Table 4. Soluble liquid (SL) formulations with Compounds A and B, respectively.Table 5. Oil-in-water emulsion (EW) formulations with Compounds A and B, respectively.Table 6. Microemulsion (ME) formulations with Compounds A and B, respectively.Table 7. Capsule suspension (CS) formulations with Compounds A and B, respectively.

[0156] Test samples were each successfully prepared with Compounds E and F (solid) disclosed in Table 1 herein above in the following formulations, respectively: suspension concentrate (SC) formulations, oil dispersion (OD) formulations, and water dispersible granule (WDG) formulations. The formulations are detailed in Tables 8-10 below.Table 8. Suspension concentrate (SC) formulations with Compounds E and F, respectively.Table 9. Oil dispersion (OD) formulations with Compounds E and F, respectively.Table 10. Water dispersible granule (WDG) formulations with Compounds E and F, respectively.Example 2.

[0157] Physical and Chemical Stability Tests

[0158] The physical appearance of the solo formulations (shown in Tables 3-10) prepared in Example 1 were observed and recorded in Table 11. The physical and chemical stabilities of substituted 5-membered ring molecule pesticides (Compounds A and B) in these soloformulations during storage at about room temperature (25 °C±3 °C) and 54 °C were tested, respectively.

[0159] For the chemical stability test, portions of each test solo formulations prepared in Example 1 were stored at about room temperature or at 54 °C for two weeks. Physical appearance and chemical stability are detailed in Tables 11 below.Tables 11. Physical and chemical stabilities of the solo formulations having Compounds A and B, respectively.

[0160] As shown in Table 11, the solo formulations, successfully prepared in Example 1, are physically stable. No change in physical appearance was observed for any of the test solo EC, SL, EW, and ME formulations after two weeks at room temperature.

[0161] The test results in Table 11 further clearly demonstrated that Compound A and B are chemically stable at 54 °C in all the tested solo EC, SL, EW, and ME formulations for at least two weeks. The retention rates of both Compounds A and B in all the tested solo EC, SL, EW, and ME formulations are higher than 95% after two weeks storage at 54 °C.

[0162] Particle size analysis was also performed for the oil-in-water (EW) formulations EW-1 to EW-4. The particle sizes of the test solo formulations EW-1 to EW-4 were measured when the test samples were freshly prepared and after two weeks storage at 54°C by particle size analyzer. The selected test results of the test solo formulations EW-1 and EW-2 are shown in FIG. 1 and Table 12. As shown in Table 12 and FIG. 1, the particle sizes of the test soloformulations EW-1 (Compound A) and EW-2 (Compound B) showed no significant change after storage at 54 °C for two weeks. The test results demonstrated a good physical stability of the prepared oil-in-water (EW) formulations.Table 12. Particle size results of the test solo oil-in-water (EW) formulations EW-1 and EW- 2 after sample preparation and after two weeks storage at 54 °C. Particle size was measured by particle size analyzer.Example 3.

[0163] Preparation of Premix Formulations

[0164] Premix formulation of Compound A and B (liquid) disclosed in Table 1 herein above with additional pesticide active ingredient(s) disclosed herein above were each successfully prepared with the following premix formulations shown in Tables 13-24 below.Table 13. Composition of 2,4-D premix formulations with Compound A (Premix- 1) and with Compound B (Premix-2).Table 14. Composition of Glyphosate IPA premix formulations with Compound A (Premix- 3) and with Compound B (Premix-4).Table 15. Composition of Glufosinate NH4 premix formulations with Compound A (Premix- 5) and with Compound B (Premix-6).Table 16. Composition of Imazethapyr premix formulations with Compound A (Premix-7) and with Compound B (Premix-8).Table 17. Composition of Haloxyfop premix formulations with Compound A (Premix-9) and with Compound B (Premix-10).Table 18. Composition of Clethodim premix formulations with Compound A (Premix-11) and with Compound B (Premix- 12).Table 19. Composition of Halauxifen-Me premix formulations with Compound A (Premix- 13) and with Compound B (Premix-14).Table 20. Composition of Quizalofop-P-ethyl premix formulations with Compound A (Premix- 15) and with Compound B (Premix- 16).Table 21. Composition of Halauxifen-Me and Cloquintocet-mexyl premix formulations with Compound A (Premix-17) and with Compound B (Premix-18).Table 22. Composition of Diclosulam premix formulations with Compound A (Premix-19) and with Compound B (Premix-20).Table 23. Composition of Mesotrione premix formulations with Compound A (Premix-21) and with Compound B (Premix-22).Table 24. Composition of Saflufenacil premix formulations with Compound A (Premix-23) and with Compound B (Premix-24).Example 4.

[0165] Physical and Chemical Stability Tests

[0166] The physical appearance of the test premix formulations (shown in Tables 13-24), successfully prepared in Example 3, were observed and recorded in Table 25 below.Table 25. Physical appearance of the test premix formulations having Compound A or B.

[0167] For the chemical stability test, portions of each test premix formulations prepared in Example 3 were stored at about room temperature or at 54 °C for two weeks. The chemical stability of substituted 5-membered ring molecule pesticides (Compounds A and B) in these test premix formulations were detailed in Table 26 below.Table 26. Chemical stability of Compound A or B in each of the test premix formulations.

[0168] As shown in Table 25, the test premix formulations, successfully prepared in Example 3, are physical stable. No significant change in physical appearance was observed for any of the test premix formulations after storage for two weeks at room temperature. The test results in Table 26 further clearly demonstrated that the Compounds A and B are chemically stable after an accelerated storage at 54 °C after two weeks in a presence of additional pesticide active ingredient(s). The retention rates of both Compounds A and B in the tested premix formulations are higher than 95% after two weeks storage at 54 °C.

[0169] 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 andmethod 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 pesticidal formulation, comprising:(a) a substituted 5-membered ring molecule pesticide having a structure of Formula (I):Formula (I) wherein:X1and X2are independently selected from the group consisting of O and S;Y is selected from the group consisting of O, NR5, and S;R1is selected from the group consisting of H and F;R2is selected from the group consisting of methyl and cyclopropyl;R3is selected from the group consisting of H, methyl, and methoxy;R4is selected from the group consisting of H, (Ci-Cie)-alkyl, (C3-Cio)-cycloalkyl, (C3- Cie)-alkenyl, (C3-Cie)-alkynyl, (Ci-Cio)-alkyl-aryl, aryl, (Ci-Cio)-alkyl-heteroaryl, heteroaryl, (Ci-Cio)-alkyl-cyano, (Ci-Cie)-haloalkyl, (Ci-Cio)-alkoxy-(Ci-Cio)-alkyl, (Ci-Cio)-alkylthio- (Ci-Cio)-alkyl, (Ci-Cio)-alkyl-sulfonyl-(Ci-Cio)-alkyl, R72R73N, SiR75R76R77, (Ci-Cio)-alkyl- SiR75R76R77, R78R79C=N, (Ci-Cio)-alkyl-C(=0)QR70, aryl-(Ci-Cio)-alkyl-C(=0)QR70, heteroaryl-(Ci-Cio)-alkyl-C(=0)QR70, (C3-Cio)-cycloalkyl-(Ci-Cio)-alkyl-C(=0)QR7°, R7°QC(=0)-(Ci-Cio)-alkyl-C(=0)QR71, R7°QC(=0)Q-(Ci-Cio)-alkyl-C(=0)QR71, hydroxy- (Ci-Cio)-alkyl-C(=0)QR70, (Ci-Cio)-alkylthio-(Ci-Cio)-alkyl-C(=0)QR70, and (R80O)2P(=O)- (Ci-Cio)-alkyl;Q is selected from the group consisting of O, S, and NR71,R70, R71, R72, R73, R74and R80are independently selected from the group consisting of H, (Ci-Cie)-alkyl, aryl, heteroaryl, (Ci-Cie)-alkyl-aryl, and (Ci-Cie)-haloalkyl;R72and R73together form a substituted or unsubstituted ring;R75, R76, and R77are independently selected from the group consisting of (Ci-Cie)-alkyl and aryl;R78and R79are independently selected from the group consisting of (Ci-Cie)-alkyl, (C1- C16)-alkyl-aryl, (Ci-Cie)-haloalkyl, aryl, and heteroaryl; or R78and R79together form a substituted or unsubstituted ring; andR5is selected from the group consisting of H, (Ci-Cie)-alkyl, (C3-Cie)-alkenyl, (C3- Cie)-alkynyl, (Ci-Cio)-alkyl-aryl, (Ci-Cio)-alkoxy, (C3-Cio)-alkenyloxy, (C3-Cio)-alkynyloxy, aryl-(Ci-Cio)-alkoxy, heterocyclyl-alkoxy, hydroxy, (Ci-Cio)-alkyl-sulfonyl, (Cs-Cs)- cycloalkyl-sulfonyl, (C3-C8)-cycloalkyl-(Ci-Cio)-alkyl-sulfonyl, aryl-sulfonyl, heteroarylsulfonyl, R72R73N-sulfonyl, (Ci-Cio)-alkoxy-NR74-sulfonyl, and aryl-oxy-sulfonyl, or an agriculturally acceptable N-oxide or salt 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 herbicide, a safener, 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 claim 1, wherein X1, X2and Y are each O; and the substituted 5- membered ring molecule pesticide has a structure of Formula (II):Formula (II)3. The formulation of claim 1, wherein X1, X2and Y are each O; R2is methyl; R3is methoxy; and the substituted 5-membered ring molecule pesticide has a structure of Formula (III):Formula (III).

4. The formulation of claim 1, wherein X1is S; X2is selected from O or S; Y is O; R2and R3are each methyl; and the substituted 5-membered ring molecule pesticide has a structure of Formula (IV):Formula (IV).

5. The formulation of claim 1, wherein X1, X2and Y are each O; R1is H; R2and R3are each methyl; and the substituted 5-membered ring molecule pesticide has a structure of Formula (V):

6. The formulation of claim 1, wherein X1, X2and Y are each O; R1is H; R2is cyclopropyl; R3is H; and the substituted 5-membered ring molecule pesticide has a structure of Formula (VI):Formula (VI).

7. The formulation of claim 1, wherein X1, X2and Y are each O; R1is F; R2and R3are each methyl; and the substituted 5-membered ring molecule pesticide has a structure ofFormula (VII):Formula (VII).

8. The formulation of claim 1, wherein X1, X2and Y are each O; R1is F; R2is cyclopropyl; R3is H; and the substituted 5-membered ring molecule pesticide has a structure of Formula (VIII):Formula (VIII).

9. The formulation of claim 1, wherein X1, X2and Y are each O; R1is H; R2is methyl; R3is methoxy; and the substituted 5-membered ring molecule pesticide has a structure of Formula (IX):Formula (IX).

10. The formulation of claim 1, wherein X1, X2and Y are each O; R1is F; R2is methyl; R3is methoxy; and the substituted 5-membered ring molecule pesticide has a structure of Formula (X):Formula (X).

11. The formulation of claim 1, wherein X1is S; X2is selected from O or S; Y is O; and the substituted 5-membered ring molecule pesticide has a structure of Formula (XI):Formula (XI).

12. The formulation of claim 1, wherein X1and X2are independently S; Y is O; and the substituted 5-membered ring molecule pesticide has a structure of Formula (XII):Formula (XII)13. The formulation of claim 1, wherein the substituted 5-membered ring molecule pesticide is selected from the group of Compounds A-Q:Compound I Compound J Compound K Compound LCompound M Compound N Compound OThe formulation of claim 1, wherein the substituted 5-membered ring molecule pesticide is selected from the group of Compounds PYR-1 to PYR-21 :PYR-9 PYR-10 PYR-11 PYR-12PYR-21.

15. The formulation of any of claims 1-14, wherein the formulation is a liquid formulation and wherein the substituted 5-membered ring molecule pesticide 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.

16. The formulation of claim 15, wherein the 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.

17. The formulation of claim 15 or 16, 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 diamides, an ester amide, an alkylene carbonate, a methylated seedoil, 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, a ester solvent, an alkyl pyrrolidone, or a polymeric ether.

18. The formulation of any of claims 1-14, wherein the formulation is a solid formulation, and the substituted 5-membered ring molecule pesticide 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.

19. The formulation of claim 18, wherein the solid formulation is a water-dispersible granule or a soluble granule.

20. A method of controlling undesirable vegetation comprising: applying the pesticidal formulation of any one of claims 1-19 to the undesirable vegetation or an area adjacent the undesirable vegetation or applied to soil or water around the undesirable vegetation by spraying, atomizing, dusting, sprinkling, spreading, or direct application of the pesticidal formulation.

21. The method of claim 20, wherein the pesticidal formulation is applied in crop plants that are resistant to one or more of herbicides, insecticides, fungicides, pathogens, insects, or combinations thereof.

22. The method of claim 20 or 21, wherein the undesirable vegetation comprises grasses, broadleaf weeds, sedge weeds, and combinations thereof.

23. The method of any of claims 20-22, wherein the pesticidal formulation is applied preemergence or post- emergence to the undesirable vegetation.

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