Substituted 5-membered ring molecules and their use as pesticides
Substituted 5-membered ring molecules, particularly lactams or thiolactams, are developed to address the inadequacies of existing herbicides, providing effective control of undesirable vegetation with minimal impact on desirable crops.
Patent Information
- Application Number
- PCT/US2025/023383
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-04-09
- Filing Date
- 2025-04-07
- Publication Date
- 2025-10-16
AI Technical Summary
Existing herbicides are inadequate for effectively controlling undesirable vegetation in various locations such as croplands, lawns, pastures, gardens, and recreational areas, necessitating the development of new herbicides with improved efficacy and specificity.
Development of substituted 5-membered ring molecules, including lactams or thiolactams, with hydrogenated or halogenated benzyl groups and other substituents, which can be used as herbicides to control undesirable vegetation.
The substituted 5-membered ring molecules exhibit herbicidal activity, effectively controlling undesirable vegetation with minimal impact on desirable crops, offering targeted and efficient herbicidal effects.
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Abstract
Description
[0001] Attorney Docket: 212168-WO-SEC-1 SUBSTITUTED 5-MEMBERED RING MOLECULES AND THEIR USE ASPESTICIDES CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Application Serial No. 63 / 631,539,filed on April 9, 2024, entitled SUBSTITUTED 5-MEMBERED RING MOLECULES ANDTHEIR USE AS PESTICIDES, the entire disclosure of which is hereby expressly incorporated byreference. FIELD The present disclosure is directed to substituted 5-membered ring molecules havingherbicidal activity. Methods of synthesizing these substituted 5-membered ring molecules,compositions comprising these molecules, and processes for using these molecules are alsodisclosed. These molecules may be used, for example, as herbicides to control undesirable vegetation. BACKGROUND Many recurring problems in agriculture involve controlling the growth of undesirablevegetation. If it is not controlled, the undesirable vegetation can, for instance, negatively affect the growth of desirable vegetation, such as crops, lawns, pastures, gardens, and recreational areas. To help control undesirable vegetation, researchers have produced a variety of chemicals and chemical compositions effective in controlling such unwanted growth. However, there exists an ongoingneed for new herbicides and methods to control the growth of undesirable vegetation in variouslocations. SUMMARY Disclosed herein are substituted 5-membered ring molecules that may be used asherbicides to control undesirable vegetation in various locations, such as croplands, lawns,pastures, gardens, and recreational areas. The molecules may include lactams or thiolactams, eitherof which may be substituted with a hydrogenated or halogenated benzyl group and other groups,such as an amino acid or other derivatives thereof. Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula(I): wherein: X1 and X2 are independently selected from the group consisting of O and S;Y is selected from the group consisting of O, NH, and S; R1, R2, and R3 are independently selected from the group consisting of H, Cl, and F,with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R4 is selected from the group consisting of methyl, methoxy, and cyclopropyl;R5 is selected from the group consisting of H, methyl, and methoxy;R6is selected from the group consisting of H, hydroxy, (C1-C8)-alkyl, (C3-C8)-alkenyl, (C3- C8)-alkynyl, (C3-C8)-cycloalkyl, (C4-C10)-alkyl cycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C5-C12)-aryl, (C6-C18)-alkylaryl, (C1-C12)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C8)-alkoxy, (C5-C16)-arylalkoxy, (C1-C6)-alkylcyano, (C1- C8)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C6)-alkylthio-(C1-C6)-alkyl, (C0-C6)-alkyl- sulfonyl-R74, NR72R73, SiR75R76R77, (C1-C6)-alkyl-SiR75R76R77, R78R79C=N, (C1-C10)-alkyl- C(=O)QR70, aryl-(C1-C6)-alkyl-C(=O)QR70, heteroaryl-(C1-C6)-alkyl-C(=O)QR70, (C3-C10)- cycloalkyl-(C0-C6)-alkyl-C(=O)QR70, R70QC(=O)-(C1-C6)-alkyl-C(=O)QR71, R70QC(=O)Q-(C1-C6)- alkyl-C(=O)QR71, hydroxy-(C1-C6)-alkyl-C(=O)QR70, (C1-C6)-alkylthio-(C1-C6)-alkyl-C(=O)QR70, and salts thereof; Q is selected from the group consisting of O, S, and NR72, R70, R71, R72, R73, and R74are independently selected from the group consisting of H, (C1- C16)-alkyl, (C4-C16)-aryl, (C1-C16)-heteroaryl, (C5-C16)-alkylaryl,(C1-C16)-haloalkyl, (C1-C16)- arylalkoxy, NR78R79, and R72and R73together may form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl andaryl; and Attorney Docket: 212168-WO-SEC-1 R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (I). In some aspects, the substituted 5-membered ring molecules are molecules of Formula (II): wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (II). Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (III): wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring: or an agriculturally-acceptable salt of the molecule of Formula (III). Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (IV): wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (IV). Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (V): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (V).
[0002] Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (VI): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)-alkyl- aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (VI).
[0003] Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (VII): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)-alkyl- aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (VII). In some aspects, the substituted 5-membered ring molecules are molecules of Formula (VIII): Attorney Docket: 212168-WO-SEC-1 wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; and R6is selected from the group consisting of H, (C1-C16)-alkyl, (C1-C10)-alkyl-aryl, and aryl; or an agriculturally-acceptable salt of the molecule of Formula (VIII). In some aspects, the substituted 5-membered ring molecules are molecules of Formula (IX): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; and R6is selected from the group consisting of H, (C1-C16)-alkyl, ((C1-C10)-alkyl-aryl, and aryl; or an agriculturally-acceptable salt of the molecule of Formula (IX). Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (X): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; and R6is selected from the group consisting of H, (C1-C16)-alkyl, (C1-C10)-alkyl-aryl, and aryl; or an agriculturally-acceptable salt of the molecule of Formula (X). The description below sets forth details of one or more aspects of the present disclosure. Other features, objects, and advantages will be apparent from the description and from the claims. DETAILED DESCRIPTION The present disclosure includes molecules that may be used as herbicides to control undesirable vegetation in various locations, such as croplands, lawns, pastures, gardens, and recreational areas. These substituted 5-membered ring molecules, such as lactam- or thiolactam-based molecules, may be substituted with hydrogenated or halogenated benzyl groups and othergroups, such as amino acid groups or derivatives thereof. The present disclosure also includesmethods of synthesizing these substituted 5-membered ring molecules, compositions comprisingthese molecules, and processes for using the molecules for controlling undesirable vegetation. Insome 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, or oats. In some aspects, the molecules are graminicides used to control undesirable vegetation including grass-type species.1. DefinitionsTerms used herein will have their customary meaning in the art unless specified otherwise. The singular forms "a" and "the" include plural references unless stated otherwise. 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 Attorney Docket: 212168-WO-SEC-1 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. As used herein, the terms “herbicide” and “herbicidal active ingredient” refer to 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.As used herein, the term “herbicidal effect” is an adversely modifying effect of an active ingredient 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 term “herbicide resistance” refers to an inherited ability of anindividual plant to survive an herbicide application that would kill a normal population of the samespecies 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. As used herein, the term “herbicide tolerance” refers to the inherent ability of a speciesof 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, ratherthan resistance selected for in that species by the application of an herbicide.As used herein, a “composition” is a mixture comprising at least one herbicide and 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. As used herein, "applying" an herbicide or herbicidal composition refers to delivering itdirectly 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, post-emergently contacting the undesirable vegetation, or contacting the area adjacent to the undesirable vegetation. 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. 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 cereals, Attorney Docket: 212168-WO-SEC-1 legumes, vegetables, orchard and timber trees, grapevines, etc. Preferably, herbicides or herbicidal compositions have zero or minimal herbicidal effect on crops. As used herein, the term "undesirable vegetation" refers to vegetation not wanted in a given area, for instance, weed species. Herbicides or herbicidal compositions are used to control undesirable vegetation. Preferably, herbicides or herbicidal compositions have a large or complete herbicidal effect on undesirable vegetation. As used herein, “alkyl” refers to saturated, straight-chained, or branched saturatedhydrocarbon moieties. Unless otherwise specified, C1-C16 alkyl groups are intended. Examplesinclude 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. As used herein, “cycloalkyl” refers to saturated hydrocarbon moieties arranged in a ring.As used herein, “alkylcycloalkyl” refers to cycloalkyl moities with alkyl substituents. Unlessotherwise specified, C3-C16cycloalkyl or alkylcycloalkyl groups are intended. Examples include cyclopropyl, cyclobutyl, methylcyclopropyl, 1,1-dimethylcyclopropyl, 1,2-dimethylcyclopropyl, cyclopentyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 1,2-dimethylcyclobutyl, 1,3-dimethylcyclobutyl, 1-ethylcyclobutyl, cyclohexyl, 1,2-dimethylcyclobutyl, 1,3-dimethylcyclobutyl, 1-ethylcyclobutyl, 1-methylcyclopentyl, 2-methylcyclopentyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1,1-dimethylcyclopentyl, 1,2- dimethylcyclopentyl, 1,3-dimethylcyclopentyl, 1,4-dimethylcyclopentyl, 2,3- dimethylcyclopentyl, 1-ethylcyclopentyl, 1,1,2-trimethylcyclobutyl, 1,2,3-trimethylcyclopentyl, 1-ethyl-1-methylcyclohexyl, cyclooctyl, 1-ethylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3- dimethylcyclohexyl, and 1-ethylcyclohexyl. As used herein, “haloalkyl” refers to straight-chained or branched alkyl groups, wherein 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, dichlorofluoromethyl, 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 1,1,1- trifluoroprop-2-yl. Attorney Docket: 212168-WO-SEC-1 As used herein, “alkenyl” refers to unsaturated straight-chained, or branchedhydrocarbon 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, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3- pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2- butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3- methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1- ethyl-1-propenyl, 1-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-1-pentenyl, 1-methyl-2- pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-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, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3- butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1- butenyl, 1,3-dimethyl-2-butenyl, 1,3-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-1-butenyl, 3,3-dimethyl-2- butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2- butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2- methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl. Vinyl refers to a group having the strutcture –CH=CH2; 1-propenyl refers to a group with the structure–CH=CH-CH3; and 2-propenyl refers to a group with the structure –CH2-CH=CH2. As used herein, “alkynyl” represents unsaturated straight-chained or branchedhydrocarbon moieties containing a triple bond. Unless otherwise specified, C3-C16 alkynyl groupsare intended. Alkynyl groups may contain more than one unsaturated bond. Examples include C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3- butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1- butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2-pentynyl, 4-methyl-2-pentynyl, 1-methyl-3-pentynyl, 2-methyl- 3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 1,1-dimethyl-2- butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl- 1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2- propynyl. As used herein, “alkoxy” refers to a group of the formula R-O-, where R is alkyl asdefined above. Unless otherwise specified, alkoxy groups wherein R is a C1-C10alkyl group are Attorney Docket: 212168-WO-SEC-1 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. As used herein, “alkylthio” refers to a group of the formula R-S- where R is alkyl asdefined above. Unless otherwise specified, alkylthio groups wherein R is a C1-C10alkyl group are intended. Examples include methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1- methyl-propylthio, 2-methylpropylthio, 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 1-ethyl-2-methylpropylthio. 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 derivativeterms such as heteroaryloxy, refers to a 5- or 6-membered aromatic ring containing one or moreheteroatoms, 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, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, C1-C6haloalkyl, C1-C6haloalkoxy, C1-C6acyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6alkoxycarbonyl, C1-C6carbamoyl, hydroxycarbonyl, C1-C6alkylcarbonyl, aminocarbonyl, C1-C6alkylaminocarbonyl, C1- C6dialkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. As used herein, “alkylaryl”, as well as derivative terms such as arylalkoxy, refers to aC1-C16 alkyl group substituted with one or more phenyl, indanyl or naphthyl groups, with phenylor benzyl substituents being preferred. For instance, C7-C16 alkylaryl refers to a group wherein thetotal number of carbon atoms in the group is 7 to 16. Attorney Docket: 212168-WO-SEC-1 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). As used herein, “alkoxycarbonyl” refers to a group of the formula wherein R isalkyl. As used herein “alkyl-sulfonyl” refers to a group of the formula , where R isalkyl. As used herein carbamyl (also referred to as carbamoyl and aminocarbonyl) refers to a group of the . As used C6 trialkylsilyl refers to a group of the formula –SiR3 wherein each R is independently a C1-C6 alkyl group (the group contains a total of 3 to 18 carbon atoms). As used herein Me refers to a methyl group; OMe refers to a methoxy group; i-Pr refers to an isopropyl group. As used herein, the term halogen including derivative terms such as halo refers to fluorine, chlorine, bromine and iodine. As used herein, “substituted” refers to any of the moities defined above, such as “alkyl,”“alkenyl,” “cycloalkyl,” etc., which is substituted with one or more substituents selected fromhalogen, hydroxy, nitro, cyano, formyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, C1-C6haloalkyl, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1- C6alkoxycarbonyl, C1-C6carbamoyl, hydroxycarbonyl, C1-C6alkylcarbonyl, aminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. As used herein, agriculturally acceptable salts refer to salts that are approved for use inagricultural applications. Agriculturally acceptable salts of herbicides may be converted in plants,water, or soil to the referenced herbicide, which, depending on the pH, may be in the dissociated or undissociated form. Exemplary agriculturally acceptable salts include but are not limited to: cationic alkali metals or alkali earth metals; ammonium ions; mono-, di-, tri-, or tetra- alkylammonium ions; mono-, di-, tri-, or tetra-alkylhydroxyammonium ions; and unsubstituted or substituted morpholinium ions. Attorney Docket: 212168-WO-SEC-1 As used herein, "active ingredient" or "ai" refers to a chemical compound or composition that has an effect on vegetation, for example, a herbicidal effect or a safening effect on the vegetation. As used herein, "acid equivalent" or "ae" refers to the amount of the acid form of an active ingredient that is calculated from the amount of a salt or ester form of that active ingredient. For example, if the acid form of an active ingredient "Z" has a molecular weight of 120 Dalton,and the salt form of Z has a molecular weight of 150 Dalton, an application of 75 grams of activeingredient per hectare (g ai / ha) of the Z salt would be equal to applying 60 grams of acid equivalentper hectare (g ae / ha) of the acid form of Z:75 g ai / ha Z salt * (120 Da Z acid / 150 Da Z salt) = 60 g ae / ha Z acid.2. Substituted 5-Membered Ring MoleculesDisclosed herein are substituted 5-membered ring molecules, such as substituted lactam-based molecules or thiolactam-based molecules, that may be used as herbicides to controlundesirable vegetation in various locations, such as croplands, lawns, pastures, gardens, and recreational areas. The molecules include molecules that are substituted with halogenated benzylgroups and amino acid groups, and derivatives thereof.In some aspects, the substituted 5-membered ring molecules are molecules 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, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R4 is selected from the group consisting of methyl, methoxy, and cyclopropyl; Attorney Docket: 212168-WO-SEC-1 R5is selected from the group consisting of H, methyl, and methoxy; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C1-C10)-alkyl-aryl, aryl, (C1-C10)-alkyl-heteroaryl, heteroaryl, (C1-C10)- alkyl-cyano, (C1-C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl-sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring. In some aspects, the substituted 5-membered ring molecules are molecules of Formula (II): wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C1-C10)-alkyl-aryl, aryl, (C1-C10)-alkyl-heteroaryl, heteroaryl, (C1-C10)- alkyl-cyano, (C1-C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl-sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N; Attorney Docket: 212168-WO-SEC-1 R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring.. In some aspects, the substituted 5-membered ring molecules are molecules of Formula (III) wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C1-C10)-alkyl-aryl, aryl, (C1-C10)-alkyl-heteroaryl, heteroaryl, (C1-C10)- alkyl-cyano, (C1-C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl-sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and Attorney Docket: 212168-WO-SEC-1 R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring. In some aspects, the substituted 5-membered ring molecules are molecules of Formula (IV): wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C1-C10)-alkyl-aryl, aryl, (C1-C10)-alkyl-heteroaryl, heteroaryl, (C1-C10)- alkyl-cyano, (C1-C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl-sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N; and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring. Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (V): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C1-C10)-alkyl-aryl, aryl, (C1-C10)-alkyl-heteroaryl, heteroaryl, (C1-C10)- alkyl-cyano, (C1-C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl-sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a or unsubstituted ring.
[0004] Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (VI): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C1-C10)-alkyl-aryl, aryl, (C1-C10)-alkyl-heteroaryl, heteroaryl, (C1-C10)- alkyl-cyano, (C1-C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl-sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N; and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring.
[0005] Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (VII): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C1-C10)-alkyl-aryl, aryl, (C1-C10)-alkyl-heteroaryl, heteroaryl, (C1-C10)- alkyl-cyano, (C1-C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl-sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N; and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring.
[0006] Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (VIII): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; and R6is selected from the group consisting of H, (C1-C16)-alkyl, (C1-C10)-alkyl-aryl, and aryl. In some aspects, the substituted 5-membered ring molecules are molecules of Formula (IX): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; and R6is selected from the group consisting of H, (C1-C16)-alkyl, ((C1-C10)-alkyl-aryl, and aryl. Attorney Docket: 212168-WO-SEC-1 In some aspects, the substituted 5-membered ring molecules are molecules of Formula (X): wherein: R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; and R6is selected from the group consisting of H, (C1-C16)-alkyl, (C1-C10)-alkyl-aryl, and aryl. Examples of the substituted 5-membered ring molecules of the present disclosure arelisted in Table 1 below. Analytical data and the method of preparation are also given in Table 1.The methods of preparation are described in Section 3 below. Table 1: Examples of 5-member ring-based molecules Cm d Prep od Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method
[0007] Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method
[0008] Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method
[0009] Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMPrep No R (H , C or F)Method Attorney Docket: 212168-WO-SEC-1 CmpdStructure Mass NMR (Prep No H , C or F)Method 3. Preparation of Substituted 5-membered Ring MoleculesSubstituted 5-membered ring molecules of the present disclosure were prepared inaccordance with the methods given below.Method 1: Preparation of Methyl (S)-2-(1-benzyl-5-oxopyrrolidin-2-yl)acetate (Intermediate 1- A) In a round-bottomed flask charged with magnetic stir bar was added methyl (S)-2-(5- oxopyrrolidin-2-yl)acetate (600 mg, 1 equiv) followed by THF (15 mL, 0.25 M) under N2. Lithium bis(trimethylsilyl)amide (0.5M in THF, 8.4 mL, 1.1 equiv) added at 23 °C for 15 min. Benzyl bromide (784 mg, 1.2 equiv) was added and then the reaction was stirred at 65 °C for 24 hr or until the reaction was complete. The crude reaction was concentrated and purified by silica column chromatography, (0-100% acetone in hexanes). Collection and concentration of the appropriate column fractions affords methyl (S)-2-(1-benzyl-5-oxopyrrolidin-2-yl)acetate as a yellow oil. (480 mg, 51% yield). Preparation of (S)-2-(1-benzyl-5-oxopyrrolidin-2-yl)acetic acid (Intermediate 1-B) To a stirred solution of methyl (S)-2-(1-benzyl-5-oxopyrrolidin-2-yl)acetate (385 mg, 1 equiv) in MeOH:THF (2:1, 0.25 M) was added 2M NaOH (1.6 mL, 2 equiv). The reaction was stirred at 23 °C for 20 h. After this time the reaction was concentrated by rotary evaporation, the Attorney Docket: 212168-WO-SEC-1 residue diluted with 0.1 M HCl (200 mL), and extracted with DCM. The combined organic layers were dried with Na2SO4, filtered, and concentrated to afford (S)-2-(1-benzyl-5-oxopyrrolidin-2- yl)acetic acid as a tan wax. (360 mg, 99% yield). Preparation of Methyl (2-((S)-1-benzyl-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.1) 1-Ethyl-3-(3- hydrochloride (EDC) (270 mg, 1.4 mmol, 1.2 equiv) and 4-dimethylaminopyridine (DMAP) (170 mg, 1.4 mmol, 1.2 equiv) were sequentially added to a stirred solution of (S)-2-(1-benzyl-5-oxopyrrolidin-2-yl)acetic acid (270 mg, 1.2 mmol, 1.0 equiv), methyl L-valinate hydrochloride (230 mg, 1.4 mmol, 1.2 equiv), and triethylamine (200 μL, 1.4 mmol, 1.2 equiv) in dichloromethane (5.8 mL) at 23 °C. The resulting homogeneous yellow solution was stirred at 23 °C for 16 hours or until complete. The reaction mixture was concentrated by rotary evaporation and the residue was purified by silica gel column chromatography (0% to 100% acetone in hexane gradient) to afford the desired product, methyl (2-((S)-1-benzyl-5-oxopyrrolidin-2-yl)acetyl)-L-valinate, as a colorless oil. (290mg, 72% yield) The following compounds were prepared in accordance to the procedure in Method 1: Benzyl (2-((S)-1-benzyl-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.4) The title compound as a colorless oil. (317mg, 83% yield) Attorney Docket: 212168-WO-SEC-1 Methyl (S)-2-(2-((S)-1-benzyl-5-oxopyrrolidin-2-yl)acetamido)-3-cyclopropyl- propanoate (Compound No.5) The title compound was as a colorless oil. (595mg, 92% yield) Tert-butyl (2-((S)-1-benzyl-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.3) The title compound was as a colorless oil. (733mg, 93% yield) Methyl N-(2-((S)-1-benzyl-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L-threoninate (Compound No.7) The title compound was prepared and was isolated as a yellow solid. (344mg, 84% yield) Attorney Docket: 212168-WO-SEC-1 Method 2: Preparation of Methyl (S)-2-(1-(2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetate (Intermediate 2-A) In a round-bottomed flask charged with magnetic stir bar was added methyl (S)-2-(5- oxopyrrolidin-2-yl)acetate (472 mg, 1 equiv) followed by THF (15 mL, 0.2 M) under N2. Lithium bis(trimethylsilyl)amide (1 M in THF, 3.0 mL, 1.0 equiv) added at 0 °C for 15 min. 1- (bromomethyl)-2-fluorobenzene (851 mg, 1.5 equiv) was added and then the reaction was stirred at 55 °C for 18 hr or until the reaction was complete. The crude reaction was concentrated and purified by silica column chromatography, (0-100% acetone in hexanes). Collection andconcentration of the appropriate column fractions affords methyl (S)-2-(1-(2-fluorobenzyl)-5- oxopyrrolidin-2-yl)acetate as a yellow oil. (675 mg, 81% yield). Preparation of (S)-2-(1-(2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid (Intermediate 2-B) To a stirred solution of methyl (S)-2-(1-(2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetate (575 mg, 1 equiv) in THF:water (3:1, 0.5 M) was added Lithium hydroxide monohydrate (260 mg, 5 equiv). The reaction was stirred at 20 °C for 18 h. After this time the reaction was diluted with 1.0 M HCl (11 mL, 5 equiv), and extracted with DCM. The combined organic layers were dried with Na2SO4, filtered, and concentrated to afford (S)-2-(1-(2-fluorobenzyl)-5-oxopyrrolidin-2- yl)acetic acid as a white solid. (545 mg, 95% yield).Preparation of Methyl (2-((S)-1-(2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L- valinate (Compound No.8) 1-Ethyl-3-(3- hydrochloride (EDC) (407 mg, 1.2 equiv) and 4-dimethylaminopyridine (DMAP) (170 mg, 1.4 mmol, 1.2 equiv) were sequentially added to a stirred solution of (S)-2-(1-(2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid (444 mg, 1.0 equiv), methyl L-valinate hydrochloride (296 mg, 1.0 equiv), and triethylamine (296 μL, 1.2 Attorney Docket: 212168-WO-SEC-1 equiv) in dichloromethane (10 mL) at 20 °C. The resulting homogeneous yellow solution was stirred at 20 °C for 18 hours or until complete. The reaction mixture was concentrated by rotary evaporation and the residue was purified by silica gel column chromatography (0% to 100% acetone in hexane gradient) to afford the title compound as a colorless oil. (290mg, 72% yield) The following compounds were prepared in accordance to the procedure in Method 2: Methyl (S)-2-cyclopropyl-2-(2-((S)-1-(2-fluorobenzyl)-5-oxopyrrolidin-2-yl)- acetamido)acetate (Compound No.11) The title compound was as a colorless liquid. (87mg) Methyl (2-((S)-1-(2,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.32) The title compound was prepared and was isolated as a viscous colorless oil. (307.3 mg,76% yield)Methyl (2-((S)-1-(5-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.34) Attorney Docket: 212168-WO-SEC-1 The title compound as a glassy colorless oil. (830.8 mg, 88% yield)Methyl N-(2-((S)-1-(2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threoninate (Compound No.49) The title compound was as a pale-yellow liquid. (80 mg)Methyl (S)-3-yclopropyl-2-(2-((S)-1-(2,5-difluorobenzyl)-5-oxopyrrolidin-2- yl)acetamido)propanoate (Compound No.61) The title compound was prepared and was isolated as a pale yellow liquid. (65 mg) Attorney Docket: 212168-WO-SEC-1 Methyl N-(2-((S)-1-(2,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threoninate (Compound No.63) The title compound was as a pale yellow liquid. (74 mg)Methyl (S)-2-(2-((S)-1-(5-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoate (Compound No.73) The title compound as a brown semi-solid. (163 mg)Methyl N-(2-((S)-1-(5-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl- L-threoninate (Compound No.75)
[0010] Attorney Docket: 212168-WO-SEC-1 The title compound was prepared and was isolated as a white gummy material. (120 mg)Method 3: Preparation of Methyl (S)-2-(1-(3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetate (Intermediate 3-A) (S)-2-(5- mg, N2. Lithium bis(trimethylsilyl)amide (1 M in THF, 3.0 mL, 1.0 equiv) added at 0 °C for 15 min. 1- (bromomethyl)-2-fluorobenzene (851 mg, 1.5 equiv) was added and then the reaction was stirred at 55 °C for 18 hr or until the reaction was complete. The crude reaction was concentrated and purified by silica column chromatography, (0-100% acetone in hexanes). Collection and concentration of the appropriate column fractions affords methyl (S)-2-(1-(2-fluorobenzyl)-5- oxopyrrolidin-2-yl)acetate as a yellow oil (650 mg, 77% yield). Preparation of (S)-2-(1-(3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid 2-yl)acetate (550 mg, 1 equiv) in THF:water (3:1, 0.25 M) was added Lithium hydroxide monohydrate (248 mg, 5 equiv). The reaction was stirred at 20 °C for 18 h. After this time the reaction was diluted with 1.0 M HCl (10 mL, 5 equiv), and extracted with DCM. The combined organic layers were dried with Na2SO4, filtered, and concentrated to afford (S)-2-(1-(3-fluorobenzyl)-5-oxopyrrolidin- 2-yl)acetic acid as a white solid (487 mg, 93% yield).Preparation of Methyl (2-((S)-1-(3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L- valinate (Compound No.12) In a 25 mL reaction stir bar was added (S)-2-(1-(3- fluorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid (387 mg, 1.540 mmol) and methyl L-valinate Attorney Docket: 212168-WO-SEC-1 hydrochloride (258 mg, 1.540 mmol) in CH2Cl2(15.40 mL). Triethylamine (0.258 mL, 1.848 mmol), 3-(((ethylimino)methylene)amino)-N,N-dimethylpropan-1-amine hydrochloride (354 mg, 1.848 mmol) and N,N-dimethylpyridin-4-amine (226 mg, 1.848 mmol) was added sequentially. The reaction was stirred at 20 °C for 18 hr. The reaction was concentrated and purified by silica column chromatography (0-100% acetone in hexanes) to afford the title compound as a colorless oil. (441.8mg, 76% yield) The following compounds were prepared in accordance to the procedure in Method 3: Methyl (S)-2-cyclopropyl-2-(2-((S)-1-(3-fluorobenzyl)-5-oxopyrrolidin-2- yl)acetamido) acetate (Compound No.15) as a colorless liquid. (116mg) Methyl (2-((S)-1-(3,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.36) The title compound was as a clear oil. (195.6 mg, 50% yield)Methyl (S)-3-cyclopropyl-2-(2-((S)-1-(3,5-difluorobenzyl)-5-oxopyrrolidin-2- yl)acetamido)propanoate (Compound No.38) Attorney Docket: 212168-WO-SEC-1 The title compound as a colorless liquid. (114 mg)Methyl N-(2-((S)-1-(3,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threoninate (Compound No.40) The title compound as a clear galssy semi solid. (350.9 mg, 86% yield)Methyl (2-((S)-1-(3-chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.44)
[0011] Attorney Docket: 212168-WO-SEC-1 The title compound was prepared and was isolated as a clear oil. (522 mg, 63% yield)Methyl (2-((S)-1-(2-chloro-3,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.46) The title compound as a crystalline white solid. (401 mg,91% yield)Methyl N-(2-((S)-1-(3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threoninate (Compound No.50) The title compound as a pale-yellow liquid. (80 mg)Methyl (S)-2-(2-((S)-1-(3-chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoate (Compound No.65) Attorney Docket: 212168-WO-SEC-1 The title compound was as a pale yellow liquid. (99 mg)Methyl N-(2-((S)-1-(3-chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl- L-threoninate (Compound No.71) The title compound as a pale yellow liquid. (80 mg)Method 4: Preparation of Methyl (S)-2-(1-(3-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetate a was (S)-2-(5- oxopyrrolidin-2-yl)acetate (800 mg, 1.0 equiv) followed by THF (20 mL, 0.25 M) under N2. Lithium bis(trimethylsilyl)amide (0.5 M in THF, 11.2 mL, 1.1 equiv) added at 23 °C for 15 min. 1-(bromomethyl)-3-chlorobenzene (1.26 g, 1.2 equiv) was added and then the reaction was stirred at 65 °C for 24 hr. The crude reaction was concentrated and purified by silica column chromatography, (0-100% acetone in hexanes). Collection and concentration of the appropriate column fractions affords methyl (S)-2-(1-(3-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetate as a yellow oil (990 mg, 69% yield). Attorney Docket: 212168-WO-SEC-1 Preparation of (S)-2-(1-(3-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid (Intermediate 4-B) 2-yl)acetate (880 mg, 1 equiv) in MeOH:THF (2:1, 0.25 M) was added 2M NaOH (3 mL, 2 equiv). The reaction was stirred at 23 °C for 20 h. After this time the reaction was concentrated, the residue diluted with 0.1 M HCl (200 mL), and extracted with DCM. The combined organic layers were dried with Na2SO4, filtered, and concentrated to afford (S)-2-(1-(3-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid as a yellow powder (750 mg, 90% yield). Preparation of Methyl (2-((S)-1-(3-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L- valinate (Compound No.18) 1-Ethyl-3-(3- hydrochloride (EDC) (275 mg, 1.2 equiv) and 4-dimethylaminopyridine (DMAP) (175 mg, 1.2 equiv) were sequentially added to a stirred solution of (S)-2-(1-(3-chlorobenzyl-5-oxopyrrolidin-2-yl)acetic acid (320 mg, 1.0 equiv), methyl L-valinate hydrochloride (240 mg, 1.2 equiv), and triethylamine (200 μL, 1.2 equiv) in dichloromethane (6 mL) at 23°C. The resulting homogeneous yellow solution was stirred at 23 °C for 18 hours or until complete. The reaction mixture was concentrated by rotary evaporation and the residue was purified by silica gel column chromatography (0% to 100% acetone in hexane gradient) to afford the title compound as a colorless oil. (370mg, 81% yield) Method 5: Preparation of Methyl (S)-2-(1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetate In a round-bottomed flask charged with magnetic stir bar was added methyl (S)-2-(5- oxopyrrolidin-2-yl)acetate (1.0 g, 1 equiv) followed by THF (30 mL, 0.2 M) under N2. Lithium Attorney Docket: 212168-WO-SEC-1 bis(trimethylsilyl)amide (1 M in THF, 1.0 equiv) added at 23 °C for 15 min.1-(bromomethyl)-2- chloro-3-fluorobenzene (1.71 g, 1.2 equiv) was added and then the reaction was stirred at 23 °C for 18 hr. The crude reaction was concentrated and purified by silica column chromatography, (0- 100% acetone in hexanes). Collection and concentration of the appropriate column fractions affords methyl (S)-2-(1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetate as a yellow oil. (1.20 g, 62% yield). Preparation of (S)-2-(1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid (Intermediate 5-B) To a stirred solution of methyl (S)-2-(1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2- yl)acetate (1.09 g, 1 equiv) in THF:water (3:1, 0.2 M) was added Lithium hydroxide monohydrate (262 mg, 3 equiv). The reaction was stirred at 23 °C for 16 h. After this time the reaction was concentrated, diluted with 0.1 M HCl (100 mL, 3 equiv), and extracted with DCM. The combined organic layers were dried with Na2SO4, filtered, and concentrated to afford (S)-2-(1-(2-chloro-3- fluorobenzyl)-5-oxopyrrolidin-2-yl)acetic acidas a white solid. (1.02 g, 96% yield). Preparation of Methyl (2-((S)-1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2- yl)acetyl)-L-valinate (Compound No.26) 1-Ethyl-3-(3- - hydrochloride (EDC) (201 mg, 1.2 equiv) and 4-dimethylaminopyridine (DMAP) (128 mg, 1.2 equiv) were sequentially added to a stirred solution of (S)-2-(1-(2-chloro-3-fluorobenzyl-5-oxopyrrolidin-2-yl)acetic acid (250 mg, 1.0 equiv), methyl L-valinate hydrochloride (176 mg, 1.2 equiv), and triethylamine (146 μL, 1.2 equiv) in dichloromethane (10 mL, 0.1 M) at 23 °C. The resulting homogeneous yellow solution was stirred at 23 °C for 18 hours or until complete. The reaction mixture was concentrated by rotary evaporation and the residue was purified by silica gel column chromatography (0% to 100% acetone in hexane gradient) to afford the title compound as a colorless oil. (295mg, 84% yield) Attorney Docket: 212168-WO-SEC-1 The following compounds were prepared in accordance to the procedure in Method 5: Methyl N-(2-((S)-1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl- L-threoninate (Compound No.30) The title compound as a thick clear and colorless oil. (318mg, 84% yield) Methyl (S)-2-(2-((S)-1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoate (Compound No.28) The title compound isolated as a thick clear and colorless oil. (354mg, 95%) Method 6: Preparation of Methyl (S)-2-(1-(2-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetate Attorney Docket: 212168-WO-SEC-1 In a round-bottomed flask charged with magnetic stir bar was added methyl (S)-2-(5- oxopyrrolidin-2-yl)acetate (900 mg, 1.0 equiv) followed by THF (30 mL, 0.2 M) under N2.Lithium bis(trimethylsilyl)amide (1 M in THF, 6.9 mL, 1.2 equiv) added at 23 °C for 15 min. 1- (bromomethyl)-2-chlorobenzene (1.41 g, 1.2 equiv) was added and then the reaction was stirred at 23 °C for 18 hr or until the reaction was complete. The crude reaction was concentrated and purified by silica column chromatography, (0-100% acetone in hexanes). Collection and concentration of the appropriate column fractions affords methyl (S)-2-(1-(2-chlorobenzyl)-5- oxopyrrolidin-2-yl)acetate as a yellow oil (787 mg, 48% yield). Preparation of (S)-2-(1-(2-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid (Intermediate 6-B) 2-yl)acetate (708 mg, 1 equiv) in THF:water (3:1, 0.2 M) was added Lithium hydroxide monohydrate (181 mg, 3 equiv). The reaction was stirred at 23 °C for 16 h. After this time the reaction was concentrated, the residue diluted with 0.1 M HCl (100 mL, 4 equiv), and extracted with DCM. The combined organic layers were dried with Na2SO4, filtered, and concentrated to afford (S)-2-(1-(2- chlorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid as a white solid (660 mg, 95% yield). Preparation of Methyl (2-((S)-1-(2-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L- valinate (Compound No.16) 1-Ethyl-3-(3- hydrochloride (EDC) (298 mg, 1.2 equiv) and 4-dimethylaminopyridine (DMAP) (190 mg, 1.2 equiv) were sequentially added to a stirred solution of (S)-2-(1-(2-fluorobenzyl-5-oxopyrrolidin-2-yl)acetic acid (347 mg, 1.0 equiv), methyl L-valinate hydrochloride (261 mg, 1.2 equiv), and triethylamine (217 μL, 1.2 equiv) in dichloromethane (10 mL) at 23 °C. The resulting homogeneous yellow solution was stirred at 23 °C for 18 hours or until complete. The reaction mixture was concentrated by rotary evaporation Attorney Docket: 212168-WO-SEC-1 and the residue was purified by silica gel column chromatography (0% to 100% acetone in hexane gradient) to afford the title compound as a colorless oil. (436mg, 86% yield) The following compounds were prepared in accordance to the procedure in Example 6: Methyl (2-((S)-1-(2-chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.42) The title compound was prepared and was isolated as a clear and colorless thick oil. (378 mg, 88% yield)Methyl (S)-2-(2-((S)-1-(2-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoate (Compound No.53) The title compound was was as a pale yellow liquid. (115 mg)Methyl N-(2-((S)-1-(2-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threoninate (Compound No.55) Attorney Docket: 212168-WO-SEC-1 The title compound as a pale yellow liquid. (120 mg)Methyl (S)-2-(2-((S)-1-(2-chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoate (Compound No.66) The title compound was as a pale yellow liquid. (91 mg)Methyl N-(2-((S)-1-(2-chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl- L-threoninate (Compound No.68) The title compound was prepared and was isolated as a pale yellow liquid. (99 mg) Attorney Docket: 212168-WO-SEC-1 Methyl (2-((S)-1-(2,5-dichlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.77) The title compound was as an aff white gummy material. (135mg) Methyl (S)-3-cyclopropyl-2-(2-((S)-1-(2,5-dichlorobenzyl)-5-oxopyrrolidin-2-yl)- acetamido)propanoate (Compound No.79) The title compound was as an off white gummy material. (106Methyl N-(2-((S)-1-(2,5-dichlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threoninate (Compound No.81)
[0012] Attorney Docket: 212168-WO-SEC-1 The title compound was prepared and was isolated as an off white gummy material. (98 mg) Method 7: Preparation of Methyl (S)-2-(1-(3-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetate (Intermediate 7-A) bottomed flask charged with magnetic stir bar was added methyl (S)-2-(5- oxopyrrolidin-2-yl)acetate (1.572 g, 1 equiv) followed by THF (50 mL, 0.2 M) under N2. Lithium bis(trimethylsilyl)amide (1 M in THF, 50.0 mL, 1.0 equiv) added at 0 °C for 15 min. 1- (bromomethyl)-3-chloro-2-fluorobenzene (3.35 g, 1.5 equiv) was added and then the reaction was stirred at 20 °C for 18 hr. The crude reaction was concentrated and purified by silica columnchromatography, (0-100% acetone in hexanes). Collection and concentration of the appropriate column fractions affords methyl (S)-2-(1-(3-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetate as a yellow oil. (1.54 g, 46% yield). Preparation of (S)-2-(1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid To a stirred solution of methyl (S)-2-(1-(3-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2- yl)acetate (1.54 g, 1 equiv) in THF:water (3:1, 0.25 M) was added Lithium hydroxide monohydrate (614 mg, 5 equiv). The reaction was stirred at 20 °C for 18 h. After this time the reaction was diluted with water (10 mL), acidified with 3 M HCl (9 mL, 5 equiv), and extracted with DCM. The combined organic layers were dried with Na2SO4, filtered, and concentrated to afford (S)-2- (1-(3-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid as a white solid. (1.29 g, 79% yield). Preparation of Methyl (2-((S)-1-(3-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2- yl)acetyl)-L-valinate (Compound No.20) Attorney Docket: 212168-WO-SEC-1 1-Ethyl-3-(3- hydrochloride (EDC) (211 mg, 1.1 equiv) and 4- mg, 1.2 equiv) were sequentially added to a stirred solution of (S)-2-(1-(3-chloro-2-fluorobenzyl-5-oxopyrrolidin-2-yl)acetic acid (286 mg, 1.0 equiv), methyl L-valinate hydrochloride (168 mg, 1.0 equiv), and triethylamine (418 μL, 3.0 equiv) in dichloromethane (0.5 mL, 0.2 M) at 20 °C. The resulting homogeneous yellow solution was stirred at 20 °C for 16 hours or until complete. The reaction mixture was concentrated by rotary evaporation and the residue was purified by silica gel column chromatography (0% to 100% acetone in hexane gradient) to afford the title compound as a colorless oil. (302 mg, 74% yield) The following compounds were prepared in accordance to the procedure in Method 7: Methyl N-(2-((S)-1-(3-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl- L-threoninate (Compound No.24) The title compound was as a clear oil. (345.4mg, 81% yield) Methyl (S)-2-(2-((S)-1-(3-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-2- cyclopropylacetate (Compound No.23) Attorney Docket: 212168-WO-SEC-1 The title compound as a colorless liquid. (472mg, 74% yield) Methyl (S)-2-(2-((S)-1-(3-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoate (Compound No.57) The title compound as a pale yellow liquid. (120 mg)Methyl N-(2-((S)-1-(3-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threoninate (Compound No.59) The title compound was prepared and was isolated as a pale yellow liquid. (135 mg) Attorney Docket: 212168-WO-SEC-1 Methyl (2-((S)-1-(3,5-dichlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valinate (Compound No.83) The title compound as a pale yellow gummy material.(72 mg)Methyl (S)-3-cyclopropyl-2-(2-((S)-1-(3,5-dichlorobenzyl)-5-oxopyrrolidin-2-yl)- acetamido)propanoate (Compound No.85) The title compound as an off white gummy material. (99mg) Methyl N-(2-((S)-1-(3,5-dichlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threoninate (Compound No.87)
[0013] Attorney Docket: 212168-WO-SEC-1 The title compound as a colourless gummy material. (114mg) Method 8: Preparation of (2-((S)-1-(2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No.9) In a round-bottomed stir bar was added methyl (2-((S)-1- (2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valinate or appropriate ester intermediate (260 mg, 0.713 mmol, 1 equiv) and THF:H2O (0.2 M, 3:1). To this was added lithium hydroxide (3 equiv) and the reaction was stirred at room temperature for 16 hours or until the reaction was complete. After this time the reaction was diluted to 0.05 M with H2O, the acidified to pH 2-4 with HCl. The reaction was extracted with EtOAc (3x), the combined organic layer washed with brine, and dried over Na2SO4. The solids are filtered off and solvent removed in vacuo to afford the product as an off-white solid. (107.3mg, 41% yield) The following compounds were prepared in accordance to the procedure in Method 8: Attorney Docket: 212168-WO-SEC-1 (S)-2-(2-((S)-1-benzyl-5-oxopyrrolidin-2-yl)acetamido)-3-cyclopropylpropanoic acid (Compound No.6) The title compound was as a white solid. (150mg, 74% yield) (S)-2-(2-((S)-1-(2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoic acid (Compound No.10) The title compound was as an off white solid. (92mg, melting point = 208-210 °C) (2-((S)-1-(3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No.13) The title compound was as a white solid. (158.7mg, 51% yield) Attorney Docket: 212168-WO-SEC-1 (S)-2-(2-((S)-1-(3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3-cyclopropyl- propanoic acid (Compound No.14) The title compound was as a off white solid. (132mg, melting point = 183-185 °C) N-(2-((S)-1-(3-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threonine (Compound No.25) The title compound was as a white solid. (173.6mg, 89% yield) (2-((S)-1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No.27) Attorney Docket: 212168-WO-SEC-1 The title compound was as a white solid. (69mg, 58% yield) (2-((S)-1-(2-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No.17) The title compound was as a white solid. (222mg, 86% yield) (S)-2-(2-((S)-1-(3-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoic acid (Compound No.22)
[0014] Attorney Docket: 212168-WO-SEC-1 The title compound was as a off white solid. (99mg, melting point = 165-167 °C) (S)-2-(2-((S)-1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoic acid (Compound No.29) The title compound was as a white solid. (98mg, 58% yield) N-(2-((S)-1-(2-chloro-3-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threonine (Compound No.31)
[0015] Attorney Docket: 212168-WO-SEC-1 The title compound was as a white solid. (78mg, 55% yield) (2-((S)-1-(5-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No.35) The title compound as a white powder. (600 mg, 86%yield) (2-((S)-1-(3,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No. 37) Attorney Docket: 212168-WO-SEC-1 The title compound was prepared and was isolated as a white solid. (268.7 mg, 92%yield) (S)-3-Cyclopropyl-2-(2-((S)-1-(3,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)- acetamido)propanoic acid (Compound No.39) The title compound as an off white solid. (105 mg)N-(2-((S)-1-(3,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L-threonine (Compound No.41) The title compound as a white solid. (135.8 mg, 77%yield) (2-((S)-1-(2-chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No.43) Attorney Docket: 212168-WO-SEC-1 The title compound was as a white solid. (198 mg, 77% yield)(2-((S)-1-(3-chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No.45) The title compound was was as a white solid. (276 mg, 90% yield)(2-((S)-1-(2-chloro-3,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (47)
[0016] Attorney Docket: 212168-WO-SEC-1 The title compound was prepared and was isolated as a white solid. (148 mg, 70% yield)N-(2-((S)-1-Benzyl-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L-threonine (Compound No.48) The title compound as a pale-yellow semi solid. (70 mg)N-(2-((S)-1-(3-Fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L-threonine (Compound No.51)
[0017] Attorney Docket: 212168-WO-SEC-1 The title compound was prepared and was isolated as a pale-yellow liquid. (80 mg)N-(2-((S)-1-(2-Fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L-threonine (Compound No.52) The title compound as an off white solid. (50 mg)(S)-2-(2-((S)-1-(2-Chlorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3-cyclopropyl- propanoic acid (Compound No.54) The title compound as an off-white solid. (100 mg)N-(2-((S)-1-(2-Chlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L-threonine (Compound No.56)
[0018] Attorney Docket: 212168-WO-SEC-1 The title compound as a white solid. (95 mg)(S)-2-(2-((S)-1-(3-Chlorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3-cyclopropyl- propanoic acid (Compound No.58) The title compound as a gray solid. (120 mg)N-(2-((S)-1-(3-Chlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L-threonine (Compound No.60) The title compound was prepared and was isolated as a white solid. (80 mg) Attorney Docket: 212168-WO-SEC-1 (S)-3-Cyclopropyl-2-(2-((S)-1-(2,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)- propanoic acid (Compound No.62) The title compound as a white solid. (31 mg)N-(2-((S)-1-(2,5-Difluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L-threonine (Compound No.64) The title compound was as a white solid. (59 mg)(S)-2-(2-((S)-1-(2-Chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoic acid (Compound No.67)
[0019] Attorney Docket: 212168-WO-SEC-1 The title compound was prepared and was isolated as a white solid. (89 mg)N-(2-((S)-1-(2-Chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threonine (Compound No.69) The title compound was as a white solid. (71 mg)(S)-2-(2-((S)-1-(3-Chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoic acid (Compound No.70) The title compound as a white solid. (88 mg)(S)-1-(3-Chloro-5-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threonine (Compound No.72)
[0020] Attorney Docket: 212168-WO-SEC-1 The title compound as a white solid. (61 mg)(S)-2-(2-((S)-1-(5-Chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)-3- cyclopropylpropanoic acid (Compound No.74) The title compound was as a white solid. (249 mg)N-(2-((S)-1-(5-Chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L- threonine (Compound No.76) The title compound was was as an off white solid. (62 mg)(2-((S)-1-(2,5-Dichlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No. 78) Attorney Docket: 212168-WO-SEC-1 The title compound was as an off white solid. (120 mg)(S)-3-Cyclopropyl-2-(2-((S)-1-(2,5-dichlorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)- propanoic acid (Compound No.80) The title compound as an off white solid. (118 mg)N-(2-((S)-1-(2,5-Dichlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L-threonine (Compound No.82) The title compound was prepared and was isolated as an off white solid. (88 mg) Attorney Docket: 212168-WO-SEC-1 (2-((S)-1-(3,5-Dichlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No. 84) The title compound as a white solid. (68 mg)(S)-3-Cyclopropyl-2-(2-((S)-1-(3,5-dichlorobenzyl)-5-oxopyrrolidin-2-yl)acetamido)- propanoic acid (Compound No.86) The title compound was as a white solid. (76 mg)N-(2-((S)-1-(3,5-Dichlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-O-methyl-L-threonine (Compound No.88) The title compound was prepared and was isolated as a white solid. (106 mg) Attorney Docket: 212168-WO-SEC-1 Method 9: Preparation of (2-((S)-1-benzyl-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No. 2) A 2M aqueous solution of μL, 0.95 mmol, 2.0 equiv) was added to a stirred solution of methyl (2-((S)-1-benzyl-5-oxopyrrolidin-2-yl)acetyl)-L-valinate or appropriate methyl-L-valinate (165 mg, 0.48 mmol, 1.0 equiv) in 2:1 methanol : tetrahydrofuran (4.5 mL) at 23 °C. The homogeneous colorless solution was stirred at 23 °C for 20 h. The reaction mixture was concentrated by rotary evaporation and the residue was diluted with 0.1M aqueous hydrochloric acid solution (100 mL) and extracted with ethyl acetate (6 x 40 mL). The combined organic layers were dried with sodium sulfate, filtered, and concentrated by rotary evaporation to afford the desired product, (2-((S)-1-benzyl-5-oxopyrrolidin-2-yl)acetyl)-L-valine, as a white powder. (150 mg, 95% yield, melting point = 209-211 °C) The following compounds were prepared in accordance to the procedure in Method 9: (2-((S)-1-(3-chloro-2-fluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No.21) The title compound was as a white powder. (184 mg, 76% yield) Attorney Docket: 212168-WO-SEC-1 (2-((S)-1-(2-chlorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No.19) The title compound was as a white powder. (200 mg, 94% yield, melting point = 197-199 °C) (2-((S)-1-(2,5-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetyl)-L-valine (Compound No. 33) The title compound was as a white solid. (88 mg, 37% yield)4. CompositionsThe present disclosure also includes compositions containing the substituted 5- membered ring molecule herbicides disclosed herein. A composition is a mixture comprising atleast one substituted 5-membered ring molecule herbicide and further comprising other additivesused to enhance the properties or effectiveness of the mixture in some way. Exemplary additives include but are not limited to adjuvants, safeners, carriers, and combinations thereof. Compositions may be in various physical states, including but not limited to as solutions, emulsions, suspensions, granules, powders, and other such states. 1. CarriersIn 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. Attorney Docket: 212168-WO-SEC-1 Exemplary liquid carriers include, but are not limited to: water; 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; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-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; N-methyl-2-pyrrolidinone; N;N-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. 2. AdjuvantsIn some aspects, the additive includes an agriculturally acceptable adjuvant. Exemplary agriculturally acceptable adjuvants include, but are not limited to, antifreeze agents, antifoam agents, compatibilizing agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, colorants, odorants, penetration aids, wetting agents, spreading agents, dispersing agents, thickening agents, freeze point depressants, antimicrobial agents, crop oil, adhesives (for instance, for use in seed formulations), surfactants, protective colloids, emulsifiers, tackifiers, and mixtures thereof. Exemplary agriculturally acceptable adjuvants include, but are not limited to, crop oil concentrates (e.g., 85% mineral oil + 15% emulsifiers); nonylphenol ethoxylates; quaternary ammonium salts; blends of petroleum hydrocarbon, alkyl esters, organic acids, and anionic surfactants; C9-C11alkylpolyglycoside; alkyl phosphates, such as tris(2-ethylhexyl) phosphate (TEHP); phosphate alcohol ethoxylates; natural primary alcohol (C12- C16) ethoxylate; di-sec-butylphenol EO-PO block copolymers; polysiloxane-methyl cap; nonylphenol ethoxylate+urea ammonium nitrates; emulsified methylated seed oils; tridecyl alcohol Attorney Docket: 212168-WO-SEC-1 (synthetic) ethoxylates (e.g., 8 EO); tallow amine ethoxylates (e.g., 15 EO); and PEG(400) dioleate-99. 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- andoctadecanols; salts of fatty alcohol glycol ethers; condensates of sulfonated naphthalene and its derivatives with formaldehyde; condensates of naphthalene or of the naphthalene sulfonic acidswith phenol and formaldehyde; polyoxyethylene octylphenol ether; ethoxylated isooctyl-, octyl- ornonylphenol, 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 amines, polyethyleneimine, polyvinylpyrrolidone, and copolymers thereof. Exemplary thickeners include, but are not limited to, polysaccharides (e.g., xanthan gum), organic and inorganic sheet minerals, and mixtures thereof. Exemplary antifoam agents include, but are not limited to, silicone emulsions, long- chain alcohols, fatty acids, fatty acid salts, organofluorine compounds, and mixtures thereof. Exemplary antimicrobial agents include, but are not limited to, bactericides based ondichlorophen and benzyl alcohol hemiformal; isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones; and mixtures thereof. Exemplary antifreeze agents, include, but are not limited to ethylene glycol, propylene glycol, urea, glycerol, and mixtures thereof. 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. Attorney Docket: 212168-WO-SEC-1 Exemplary adhesives include, but are not limited to, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose, and mixtures thereof. 3. SafenersIn 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-diethyl, mephenate, naphthalic anhydride, 2,2,5-trimethyl-3-(dichloroacetyl)- 1,3-oxazolidine, 4-(dichloroacetyl)-1-oxa-4-azaspiro [4.5]-decane, oxabetrinil, R29148, and N- phenyl-sulfonylbenzoic acid amides, agriculturally acceptable salts as well as thereof and, provided they have a carboxyl group, their agriculturally acceptable derivatives. In some aspects, the safener can be cloquintocet or an ester or salt thereof, such as cloquintocet-mexyl. In some aspects, the safener can be mefenpyr or an ester or salt thereof, such as mefenpyr-diethyl. In some aspects, thesafener is employed in rice, cereal, or maize. For example, mefenpyr or cloquintocet can be usedto antagonize harmful effects of the compositions on rice, row crops, and cereals. In some aspects, the weight ratio of (a) the compounds according to Formula I (in g ae / ha) to (b) the safener or an agriculturally acceptable salt or ester thereof (in g ai / ha) can be 1:5or more, such as 1:4.75 or more, 1:4.5 or more, 1:4.25 or more, 1:4 or more, 1:3.75 or more, 1:3.5or more, 1:3.25 or more, 1:3 or more, 1:2.75 or more, 1:2.5 or more, 1:2.25 or more, 1:2 or more, 1:1.9 or more, 1:1.8 or more, 1:1.7 or more, 1:1.6 or more, 1:1.5 or more, 1:1.4 or more, 1:1.3 or more, 1:1.2 or more, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1 or more, 1.9:1 or more, 2:1 or more, 2.25:1 or more, 2.5:1 or more, 2.75:1 or more, 3:1 or more, 3.25:1 or more, 3.5:1 or more, 3.75:1 or more, 4:1 or more, 4.25:1 or more, 4.5:1 or more, 4.75:1 or more, or 5:1 or more; the weight ratio of (a) to (b) can be 5:1 or less, such as 4.75:1 or less, 4.5:1 or less, 4.25:1 or less, 4:1 or less,3.75:1 or less, 3.5:1 or less, 3.25:1 or less, 3:1 or less, 2.75:1 or less, 2.5:1 or less, 2.25:1 or less,2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 or less, 1.2:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 or less, 1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 or less, 1:1.7 or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:2.25 or less, 1:2.5 or less, 1:2.75 or less, 1:3 or less, 1:3.25 or less, 1:3.5 or less, 1:3.75 or less, 1:4 or less, 1:4.25 or less, 1:4.5 or less, or 1:4.75 or less; or the weight ratio of (a) to (b) can range from any of the Attorney Docket: 212168-WO-SEC-1 minimum ratios to any of the maximum ratios provided above, such as from 1:5 to 5:1, from 1:2 to 5:1, from 1:1 to 3:1, from 1:3 to 4:1, or from 1:1.5 to 3.5:1. 4. Other HerbicidesIn some aspects, the additive is an additional herbicide. For example, the compositions described herein can be applied in conjunction with one or more additional herbicides to control undesirable vegetation. The composition can be formulated with the one or more additional herbicides, tank mixed with the one or more additional herbicides, or applied sequentially with the one or more additional herbicides, such as the exemplary herbicides described below. ALS Inhibitors In addition to the compounds according to Formula I, the compositions can include an acetolactate synthase (ALS) inhibitor. ALS inhibitors disrupt the production of amino acids in the plant, which eventually leads to inhibition of DNA synthesis. Examples of ALS inhibitors include sulfonylureas, imidazolinones, triazolopyrimidine sulfonamides, pyrimidinyl oxybenzoates and sulfonylaminocarbonyl triazolinones. In some aspects, the ALS inhibitor can contain a triazolopyrimidine sulfonamide herbicide. In some aspects, the ALS inhibitor can contain an imidazolinone herbicide. In some aspects, the ALS inhibitor can contain a pyrimidinyl oxybenzoate herbicide. In some aspects, the ALS inhibitor can contain a sulfonylaminocarbonyl triazolinone herbicide. In some aspects, the ALS inhibitor can contain a sulfonylurea herbicide. In some aspects, the composition can include an ALS inhibitor selected from the group of imidazolinones, triazolopyrimidine sulfonamides, pyrimidinyl oxybenzoates, sulfonylaminocarbonyl triazolinones, sulfonylureas, and combinations thereof. In some cases, the composition can include amidosulfuron, azimsulfuron, bispyribac, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cloransulam, cyclosulfamuron, diclosulam, ethametsulfuron, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucetosulfuron, flumetsulam, flupyrsulfuron, foramsulfuron, halosulfuron, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metosulam, metsulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, propoxycarbazone, propyrisulfuron, prosulfuron, pyrazosulfuron, pyribenzoxim, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, pyroxsulam, rimsulfuron, sulfometuron, sulfosulfuron, thiencarbazone, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, agriculturally acceptable salts and esters thereof, and combinations thereof. The ALS inhibitor or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence Attorney Docket: 212168-WO-SEC-1 or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, the ALS inhibitor or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 0.25 grams active ingredient per hectare (g ai / ha) or more, such as 0.3 g ai / ha or more, 0.4 g ai / ha or more, 0.5 g ai / ha or more, 0.6 g ai / ha or more, 0.7 g ai / ha or more, 0.8 g ai / ha or more, 0.9 g ai / ha or more, 1 g ai / ha or more, 1.5 g ai / ha or more, 2 g ai / ha or more, 2.5 g ai / ha or more, 3 g ai / ha or more, 3.5 g ai / ha or more, 4 g ai / ha or more, 4.5 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 220 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 280 g ai / ha or more, 300 g ai / ha or more, 320 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha or more, 380 g ai / ha or more, 400 g ai / ha or more, 420 g ai / ha or more, 440 g ai / ha or more, 460 g ai / ha or more, 480 g ai / ha or more, 500 g ai / ha or more, 520 g ai / ha or more, 540 g ai / ha or more, 560 g ai / ha or more, 580 g ai / ha or more, 600 g ai / ha or more, 625 g ai / ha or more, 650 g ai / ha or more, 675 g ai / ha or more, 700 g ai / ha or more, 725 g ai / ha or more, 750 g ai / ha or more, 775 g ai / ha or more, 800 g ai / ha or more, 825 g ai / ha or more, 850 g ai / ha or more, 875 g ai / ha or more, 900 g ai / ha or more, 925 g ai / ha or more, 950 g ai / ha or more, 975 g ai / ha or more, 1000 g ai / ha or more, 1050 g ai / ha or more, 1100 g ai / ha or more, 1150 g ai / ha or more, 1200 g ai / ha or more, 1250 g ai / ha or more, 1300 g ai / ha or more, 1350 g ai / ha or more, 1400 g ai / ha or more, 1450 g ai / ha or more, 1500 g ai / ha or more, 1550 g ai / ha or more, 1600 g ai / ha or more, 1650 g ai / ha or more, 1675 g ai / ha or more, 1680 g ai / ha or more, or 1690 g ai / ha or more; in an amount of 1700 g ai / ha or less, such as 1690 g ai / ha or less, 1680 g ai / ha or less, 1675 g ai / ha or less, 1650 g ai / ha or less, 1600 g ai / ha or less, 1550 g ai / ha or less, 1500 g ai / ha or less, 1450 g ai / ha or less, 1400 g ai / ha or less, 1350 g ai / ha or less, 1300 g ai / ha or less, 1250 g ai / ha or less, 1200 g ai / ha or less, 1150 g ai / ha or less, 1100 g ai / ha or less, 1050 g ai / ha or less, 1000 g ai / ha or less, 975 g ai / ha or less, 950 g ai / ha or less, 925 g ai / ha or less, 900 g ai / ha or less, 875 g ai / ha or less, 850 g ai / ha or less, 825 g ai / ha or less, 800 g ai / ha or less, 775 g ai / ha or less, 750 g ai / ha or less, 725 g ai / ha or less, 700 g ai / ha or less, 675 g ai / ha or less, 650 g ai / ha or less, 625 g ai / ha or less, 600 g ai / ha or less, 580 g ai / ha or less, 560 g ai / ha or less, 540 g ai / ha or less, 520 g ai / ha or less, 500 g ai / ha or less, 480 g ai / ha or less, 460 g ai / ha or less, 440 g ai / ha or less, 420 g ai / ha or less, 400 g ai / ha or less, 380 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 320 g ai / ha or less, 300 g ai / ha or Attorney Docket: 212168-WO-SEC-1 less, 280 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 220 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, 55 g ai / ha or less, 50 gai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 15 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, 8 g ai / ha or less, 7 g ai / ha or less, 6 g ai / ha or less, 5 g ai / ha or less, 4.5 g ai / ha or less, 4 g ai / ha or less, 3.5 g ai / ha orless, 3 g ai / ha or less, 2.5 g ai / ha or less, 2 g ai / ha or less, 1.5 g ai / ha or less, 1 g ai / ha or less, 0.9 g ai / ha or less, 0.8 g ai / ha or less, 0.7 g ai / ha or less, 0.6 g ai / ha or less, 0.5 g ai / ha or less, 0.4 g ai / ha or less, or 0.3 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 0.25–1700 g ai / ha, 0.25–1250 g ai / ha, 0.5–150 g ai / ha, 2–90 g ai / ha, 2.5–200 g ai / ha, 3–900 g ai / ha, 5–260 g ai / ha, 5–750 g ai / ha, 5–1000 g ai / ha, 6–280 g ai / ha, 7–100 g ai / ha, 10–560 g ai / ha, 10–1600 g ai / ha, 20–500 g ai / ha, 25– 140 g ai / ha, 30–480 g ai / ha, 40–400 g ai / ha, 50–320 g ai / ha, 60–300 g ai / ha, 70–1250 g ai / ha, 100– 140 g ai / ha, 140–520 g ai / ha, or 250–1700 g ai / ha. Synthetic Auxin Herbicide In addition to the compounds according to Formula I, the compositions can include asynthetic auxin herbicide. Synthetic auxin herbicides mimic natural plant hormones and can inhibit cell division and growth. Synthetic auxin herbicides include phenoxy herbicides, benzoic acid herbicides, aryl picolinate herbicides, quinoline carboxylic acid herbicides, pyrimidine carboxylicacid herbicides, and benzothiazole herbicides, as well as agriculturally acceptable salts and esters thereof. In some aspects, the composition can include a synthetic auxin herbicide selected from the group consisting of 2,4-D; 2,4-DB; 2,3,6-TBA, 2,4-D DMA, 2,4-D choline,aminocyclopyrachlor, aminopyralid, benazolin-ethyl, chloramben, clomeprop, clopyralid, dichlorprop, dichlorprop-P, dicamba, florpyrauxifen (such as florpyrauxifen-benzyl), fluchloraminopyr (e.g., fluchloraminopyr-tefuryl), fluroxypyr, fluroxypyr-MHE, halauxifen (such as halauxifen-methyl), indolauxipyr (such as indolauxipyr-cyanomethyl), mecoprop, mecoprop-P, MCPA, MCPA-thioethyl, MCPB, picloram, quinclorac, quinmerac, triclopyr, agriculturally acceptable salts and esters thereof, and combinations thereof. In some aspects, the synthetic auxin herbicide can comprise 2,4-D, MCPA, aminopyralid, clopyralid, dicamba, florpyrauxifen, fluroxypyr, halauxifen, quinclorac, agriculturally acceptable salts and esters thereof, and combinations thereof. Attorney Docket: 212168-WO-SEC-1 The synthetic auxin herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, the synthetic auxin herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergenceor growth of vegetation in an amount of 1 gram acid equivalent per hectare (g ai) or more, such as1.5 g ai or more, 2 g ai or more, 2.5 g ai or more, 3 g ai or more, 3.5 g ai or more, 4 g ai or more, 4.5 g ai or more, 5 g ai or more, 6 g ai or more, 7 g ai or more, 8 g ai or more, 9 g ai or more, 10 g ai or more, 15 g ai or more, 20 g ai or more, 25 g ai or more, 30 g ai or more, 35 g ai or more, 40 g ai or more, 45 g ai or more, 50 g ai or more, 55 g ai or more, 60 g ai or more, 65 g ai or more, 70 g ai or more, 75 g ai or more, 80 g ai or more, 85 g ai or more, 90 g ai or more, 95 g ai or more, 100 g ai or more, 110 g ai or more, 120 g ai or more, 130 g ai or more, 140 g ai or more, 150 g ai or more, 160 g ai or more, 170 g ai or more, 180 g ai or more, 190 g ai or more, 200 g ai or more, 220 g ai or more, 240 g ai or more, 250 g ai or more, 260 g ai or more, 280 g ai or more, 300 g ai or more, 320 g ai or more, 340 g ai or more, 350 g ai or more, 360 g ai or more, 380 g ai or more, 400 g ai or more, 450 g ai or more, 500 g ai or more, 550 g ai or more, 600 g ai or more, 650 g ai or more, 700 g ai or more, 750 g ai or more, 800 g ai or more, 850 g ai or more, 900 g ai or more, 950 g ai or more, 1000 g ai or more, 1050 g ai or more, 1100 g ai or more, 1150 g ai or more, 1200 g ai or more, 1250 g ai or more, 1300 g ai or more, 1350 g ai or more, 1400 g ai or more, 1450 g ai or more, 1500 g ai or more, 1600 g ai or more, 1700 g ai or more, 1800 g ai or more, 1900 g ai or more, 2000 g ai or more, 2050 g ai or more, 2100 g ai or more, 2150 g ai or more, 2200 g ai or more, 2240 g ai or more, 2250 g ai or more, 2300 g ai or more, 2350 g ai or more, 2400 g ai or more, 2450 g ai or more, 2500 g ai or more, 2600 g ai or more, 2700 g ai or more, 2750 g ai ormore, 2800 g ai or more, 2900 g ai or more, 3000 g ai or more, 3050 g ai or more, 3100 g ai ormore, 3150 g ai or more, 3200 g ai or more, 3250 g ai or more, 3300 g ai or more, 3350 g ai or more, 3400 g ai or more, 3450 g ai or more, 3500 g ai or more, 3600 g ai or more, 3700 g ai ormore, 3750 g ai or more, 3800 g ai or more, 3900 g ai or more, or 3950 g ai or more; in an amountof 4000 g ai or less, such as 3950 g ai or less, 3900 g ai or less, 3800 g ai or less, 3750 g ai or less, 3700 g ai or less, 3600 g ai or less, 3500 g ai or less, 3450 g ai or less, 3400 g ai or less, 3350 g ai or less, 3300 g ai or less, 3250 g ai or less, 3200 g ai or less, 3150 g ai or less, 3100 g ai or less, 3050 g ai or less, 3000 g ai or less, 2900 g ai or less, 2800 g ai or less, 2750 g ai or less, 2700 g ai or less, 2600 g ai or less, 2500 g ai or less, 2450 g ai or less, 2400 g ai or less, 2350 g ai or less, 2300 g ai or less, 2250 g ai or less, 2240 g ai or less, 2200 g ai or less, 2150 g ai or less, 2100 g aior less, 2050 g ai or less, 2000 g ai or less, 1900 g ai or less, 1800 g ai or less, 1750 g ai or less,1700 g ai or less, 1600 g ai or less, 1500 g ai or less, 1450 g ai or less, 1400 g ai or less, 1350 g ai or less, 1300 g ai or less, 1250 g ai or less, 1240 g ai or less, 1200 g ai or less, 1150 g ai or less, Attorney Docket: 212168-WO-SEC-1 1100 g ai or less, 1050 g ai or less, 1000 g ai or less, 950 g ai or less, 900 g ai or less, 850 g ai or less, 800 g ai or less, 750 g ai or less, 700 g ai or less, 650 g ai or less, 600 g ai or less, 550 g ai or less, 500 g ai or less, 450 g ai or less, 400 g ai or less, 380 g ai or less, 360 g ai or less, 350 g ai or less, 340 g ai or less, 320 g ai or less, 300 g ai or less, 280 g ai or less, 260 g ai or less, 250 g ai or less, 240 g ai or less, 220 g ai or less, 200 g ai or less, 190 g ai or less, 180 g ai or less, 170 g ai orless, 160 g ai or less, 150 g ai or less, 140 g ai or less, 130 g ai or less, 120 g ai or less, 110 g ai or less, 100 g ai or less, 95 g ai or less, 90 g ai or less, 85 g ai or less, 80 g ai or less, 75 g ai or less, 70 g ai or less, 65 g ai or less, 60 g ai or less, 55 g ai or less, 50 g ai or less, 45 g ai or less, 40 g ai or less, 35 g ai or less, 30 g ai or less, 25 g ai or less, 20 g ai or less, 15 g ai or less, 10 g ai or less, 9g ai or less, 8 g ai or less, 7 g ai or less, 6 g ai or less, 5 g ai or less, 4.5 g ai or less, 4 g ai or less,3.5 g ai or less, 3 g ai or less, 2.5 g ai or less, 2 g ai or less, 1.5 g ai or less, or 1 g ai or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 1–4000 g ai, 1–2240 g ai, 1-150 g ai, 1.5–3150 g ai, 2–900 g ai, 2.5–3200 g ai, 3–1250 g ai, 5–260 g ai, 6–750 g ai, 7–2100 g ai, 10–2240 g ai, 20–3600 g ai, 40–3950 g ai, 50–400 g ai, 70–1250 g ai, 100–1400 g ai, or 250–1700 g ai. Auxin Transport Inhibitors In addition to the compounds according to Formula I, the compositions can include anauxin transport inhibitor. Auxin transport inhibitors inhibit polar transport of naturally occurring auxin, indole acetic acid (IAA), and synthetic auxin-mimicking herbicides in sensitive plants. Examples of auxin transport inhibitors include phthalamate herbicides, semicarbazone herbicides and others. In some aspects, the composition can include an auxin transport inhibitor selected from the group consisting of: chlorflurenol; diflufenzopyr; naptalam; 2,3,5-triiodobenzoic acid (2,3,5- TIBA); agriculturally acceptable salts and esters thereof; and combinations thereof. The auxin transport inhibitor or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, the auxin transport inhibitor or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 gram acid equivalent per hectare (g ai) or more, such as1.5 g ai or more, 2 g ai or more, 2.5 g ai or more, 3 g ai or more, 3.5 g ai or more, 4 g ai or more, 4.5 g ai or more, 5 g ai or more, 6 g ai or more, 7 g ai or more, 8 g ai or more, 9 g ai or more, 10 g ai or more, 15 g ai or more, 20 g ai or more, 25 g ai or more, 30 g ai or more, 35 g ai or more, 40 g ai or more, 45 g ai or more, 50 g ai or more, 55 g ai or more, 60 g ai or more, 65 g ai or more, 70 g ai or more, 75 g ai or more, 80 g ai or more, 85 g ai or more, 90 g ai or more, 95 g ai or more, 100 Attorney Docket: 212168-WO-SEC-1 g ai or more, 110 g ai or more, 120 g ai or more, 130 g ai or more, 140 g ai or more, 150 g ai or more, 160 g ai or more, 170 g ai or more, 180 g ai or more, 190 g ai or more, 200 g ai or more, 220 g ai or more, 240 g ai or more, 250 g ai or more, 260 g ai or more, 280 g ai or more, 300 g ai or more, 320 g ai or more, 340 g ai or more, 350 g ai or more, 360 g ai or more, 380 g ai or more, 400 g ai or more, 450 g ai or more, 500 g ai or more, 550 g ai or more, 600 g ai or more, 650 g ai or more, 700 g ai or more, 750 g ai or more, 800 g ai or more, 850 g ai or more, 900 g ai or more, 950 g ai or more, 1000 g ai or more, 1050 g ai or more, 1100 g ai or more, 1150 g ai or more, 1200 g ai or more, 1250 g ai or more, 1300 g ai or more, 1350 g ai or more, 1400 g ai or more, 1450 g ai or more, 1500 g ai or more, 1600 g ai or more, 1700 g ai or more, 1800 g ai or more, 1900 g ai or more, 2000 g ai or more, 2050 g ai or more, 2100 g ai or more, 2150 g ai or more, 2200 g ai or more, 2240 g ai or more, 2250 g ai or more, 2300 g ai or more, 2350 g ai or more, 2400 g ai or more, 2450 g ai or more, 2500 g ai or more, 2600 g ai or more, 2700 g ai or more, 2750 g ai or more, 2800 g ai or more, 2900 g ai or more, 3000 g ai or more, 3050 g ai or more, 3100 g ai or more, 3150 g ai or more, 3200 g ai or more, 3250 g ai or more, 3300 g ai or more, 3350 g ai or more, 3400 g ai or more, 3450 g ai or more, 3500 g ai or more, 3600 g ai or more, 3700 g ai or more, 3750 g ai or more, 3800 g ai or more, 3900 g ai or more, or 3950 g ai or more; in an amount of 4000 g ai or less, such as 3950 g ai or less, 3900 g ai or less, 3800 g ai or less, 3750 g ai or less, 3700 g ai or less, 3600 g ai or less, 3500 g ai or less, 3450 g ai or less, 3400 g ai or less, 3350 g ai or less, 3300 g ai or less, 3250 g ai or less, 3200 g ai or less, 3150 g ai or less, 3100 g ai or less, 3050 g ai or less, 3000 g ai or less, 2900 g ai or less, 2800 g ai or less, 2750 g ai or less, 2700 g ai or less, 2600 g ai or less, 2500 g ai or less, 2450 g ai or less, 2400 g ai or less, 2350 g ai or less, 2300 g ai or less, 2250 g ai or less, 2240 g ai or less, 2200 g ai or less, 2150 g ai or less, 2100 g ai or less, 2050 g ai or less, 2000 g ai or less, 1900 g ai or less, 1800 g ai or less, 1750 g ai or less, 1700 g ai or less, 1600 g ai or less, 1500 g ai or less, 1450 g ai or less, 1400 g ai or less, 1350 g ai or less, 1300 g ai or less, 1250 g ai or less, 1240 g ai or less, 1200 g ai or less, 1150 g ai or less, 1100 g ai or less, 1050 g ai or less, 1000 g ai or less, 950 g ai or less, 900 g ai or less, 850 g ai or less, 800 g ai or less, 750 g ai or less, 700 g ai or less, 650 g ai or less, 600 g ai or less, 550 g ai or less, 500 g ai or less, 450 g ai or less, 400 g ai or less, 380 g ai or less, 360 g ai or less, 350 g ai or less, 340 g ai or less, 320 g ai or less, 300 g ai or less, 280 g ai or less, 260 g ai or less, 250 g ai or less, 240 g ai or less, 220 g ai or less, 200 g ai or less, 190 g ai or less, 180 g ai or less, 170 g ai or less, 160 g ai or less, 150 g ai or less, 140 g ai or less, 130 g ai or less, 120 g ai or less, 110 g ai or less, 100 g ai or less, 95 g ai or less, 90 g ai or less, 85 g ai or less, 80 g ai or less, 75 g ai or less, 70 g ai or less, 65 g ai or less, 60 g ai or less, 55 g ai or less, 50 g ai or less, 45 g ai or less, 40 g ai or less, 35 g ai or less, 30 g ai or less, 25 g ai or less, 20 g ai or less, 15 g ai or less, 10 g ai or less, 9 g ai or less, 8 g ai or less, 7 g ai or less, 6 g ai or less, 5 g ai or less, 4.5 g ai or less, 4 g ai or less, 3.5 g ai or less, 3 g ai or less, 2.5 g ai or less, 2 g ai or less, 1.5 g ai or less, or 1 g ai or less; or in Attorney Docket: 212168-WO-SEC-1 an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 1–4000 g ai, 1–2240 g ai, 1-150 g ai, 1.5–3150 g ai, 2–900 g ai, 2.5–3200 gai, 3–1250 g ai, 5–260 g ai, 6–750 g ai, 7–2100 g ai, 10–2240 g ai, 20–3600 g ai, 40–3950 g ai,50–400 g ai, 70–1250 g ai, 100–1400 g ai, or 250–1700 g ai. Protoporphyrinogen Oxidase (PPO) Inhibitors In addition to the compounds according to Formula I, the compositions can include an inhibitor of a protoporphyrinogen oxidase (PPO), which is an enzyme involved in the biosynthesis of both heme and chlorophyll. It is believed that PPO inhibitors generate large amounts of singletoxygen, which leads to the peroxidation of the lipids in cell membranes. Examples of PPO inhibitors include acifluorfen, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, chlomethoxyfen, cinidon, fluazolate, flufenpyr, flumiclorac, flumioxazin, fluoroglycofen, fluthiacet, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4- tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3- (2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1- carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1-H-pyrazole-1- carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5- methyl-1H-pyrazo-le-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6- fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 45100-03-7), 3- [7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6- thioxo[1,3,5]triazinan-2,4-dione, agriculturally acceptable esters thereof, or combinations thereof. The PPO inhibitor herbicides or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent to the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, the PPO inhibitor or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 0.5 grams active ingredient per hectare (g ai / ha) or more, such as 1 g ai / ha or more, 1.25 g ai / ha or more, 1.5 g ai / ha or more, 1.75 g ai / ha or more, 2 g ai / ha or more, 2.5 g ai / ha or more, 3 g ai / ha or more, 3.5 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 21 g ai / ha or more, 22 g ai / ha or more, 23 g ai / ha or more, 24 g ai / ha or more, 25 g ai / ha or more, 26 g ai / ha or more, 27 g ai / ha or more, 28 g ai / ha or more, 29 g ai / ha or more, 30 g ai / ha or more, 31 g ai / ha Attorney Docket: 212168-WO-SEC-1 or more, 32 g ai / ha or more, 33 g ai / ha or more, 34 g ai / ha or more, 35 g ai / ha or more, 36 g ai / ha or more, 37 g ai / ha or more, 38 g ai / ha or more, 39 g ai / ha or more, 40 g ai / ha or more, 41 g ai / ha or more, 42 g ai / ha or more, 43 g ai / ha or more, 44 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 220 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 280 g ai / ha or more, 300 g ai / ha or more, 320 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha or more, 380 g ai / ha or more, 400 g ai / ha or more, 450 g ai / ha or more, 500 g ai / ha or more, 550 g ai / ha or more, 600 g ai / ha or more, 650 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more, or 975 g ai / ha or more; in an amount of 1000 g ai / ha or less, such as 975 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 650 g ai / ha or less, 600 g ai / ha or less, 550 g ai / ha or less, 500 g ai / ha or less, 450 g ai / ha or less, 400 g ai / ha or less, 380 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 320 g ai / ha or less, 300 g ai / ha or less, 280 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 220 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, 55 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 44 g ai / ha or less, 43 g ai / ha or less, 42 g ai / ha or less, 41 g ai / ha or less, 40 g ai / ha or less, 39 g ai / ha or less, 38 g ai / ha or less, 37 g ai / ha or less, 36 g ai / ha or less, 35 g ai / ha or less, 34 g ai / ha or less, 33 g ai / ha or less, 32 g ai / ha or less, 31 g ai / ha or less, 30 g ai / ha or less, 29 g ai / ha or less, 28 g ai / ha or less, 27 g ai / ha or less, 26 g ai / ha or less, 25 g ai / ha or less, 24 g ai / ha or less, 23 g ai / ha or less, 22 g ai / ha or less, 21 g ai / ha or less, 20 g ai / ha or less, 19 g ai / ha or less, 18 g ai / ha or less, 17 g ai / ha or less, 16 ai / ha or less, 15 g ai / ha or less, 14 g ai / ha or less, 13 g ai / ha or less, 12 g ai / ha or less, 11 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, 8 g ai / ha or less, 7 g ai / ha or less, 6 g ai / ha or less, 5 g ai / ha or less, 4 g ai / ha or less, 3.5 g ai / ha or less, 3 g ai / ha or less, 2.5 g ai / ha or less, 2 g ai / ha or less, 1.75 g ai / ha or less, 1.5 g ai / ha or less, 1.25 g ai / ha or less, or 1 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 0.5-1000 g ai / ha, 2–900 g ai / ha, 1.75-300 g ai / ha, 75–550 g ai / ha, 90–900 g ai / ha, 55–400 g ai / ha, 36–250 g ai / ha, 80–650 g ai / ha, 120–360 g ai / ha, 65–170 g ai / ha, 34–700 g ai / ha, 12–200 g ai / ha, 5–220 g ai / ha, 1.5-25 g ai / ha, 70–450 g ai / ha, 39–110 g ai / ha, or 1–975 g ai / ha. Attorney Docket: 212168-WO-SEC-1 Photoene Desaturase (PDS) Inhibitors In addition to the compounds according to Formula I, the compositions can include aphytoene desaturase (PDS) inhibitor herbicide or agriculturally acceptable salt or ester thereof.PDS inhibitors block carotenoid biosynthesis by inhibition of phytoene desaturase, a key enzyme in the carotenoid biosynthesis pathway. An absence of carotenoids leads to destruction of membrane fatty acid and chlorophyll by excessive energy. Examples of PDS inhibitors include,but are not limited to, beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, and picolinafen. In some aspects, the composition can include a PDS inhibitor herbicide selected from the group consisting of beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone,norflurazon, picolinafen, agriculturally acceptable salts and esters thereof, and combinations thereof. The PDS inhibitor herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, the PDS inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 12.5 gram active ingredient per hectare (g ai / ha) or more, such as 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 220 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 280 g ai / ha or more, 300 g ai / ha or more, 320 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha or more, 380 g ai / ha or more, 400 g ai / ha or more, 450 g ai / ha or more, 500 g ai / ha or more, 550 g ai / ha or more, 600 g ai / ha or more, 650 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more, 1000 g ai / ha or more, 1050 g ai / ha or more, 1100 g ai / ha or more, 1150 g ai / ha or more, 1200 g ai / ha or more, 1250 g ai / ha or more, 1300 g ai / ha or more, 1350 g ai / ha or more, 1400 g ai / ha or more, 1450 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2050 g ai / ha or more, 2100 g ai / ha or more, 2150 g ai / ha or more, 2200g ai / ha or more, 2240 g ai / ha or more, 2250 g ai / ha or more, 2300 g ai / ha or more, 2350 g ai / ha or more, 2400 g ai / ha or more, 2450 g ai / ha or more, 2500 g ai / ha or more, 2600 g ai / ha or more, 2700 Attorney Docket: 212168-WO-SEC-1 g ai / ha or more, 2750 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3250 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3900 g ai / ha or more, 3950 g ai / ha or more, 4000 g ai / ha or more, 4100 g ai / ha or more, 4200 g ai / ha or more, 4250 g ai / ha or more, 4300 g ai / ha or more, 4400 g ai / ha or more, or 4450 g ai / ha or more; in an amount of 4500 g ai / ha or less, such as 4450 g ai / ha or less, 4400 g ai / ha or less, 4300 g ai / ha or less, 4250 g ai / ha or less, 4100 g ai / ha or less, 4000 g ai / ha or less, 3950 g ai / ha or less, 3900 g ai / ha or less, 3800 g ai / ha or less, 3750 g ai / ha or less, 3700 g ai / ha or less, 3600 g ai / ha or less, 3500 g ai / ha or less, 3400 g ai / ha or less, 3300 g ai / ha or less, 3250 g ai / ha or less, 3200 g ai / ha or less, 3100 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 g ai / ha or less, 2750 g ai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 gai / ha or less, 2450 g ai / ha or less, 2400 g ai / ha or less, 2350 g ai / ha or less, 2300 g ai / ha or less, 2250 g ai / ha or less, 2240 g ai / ha or less, 2200 g ai / ha or less, 2150 g ai / ha or less, 2100 g ai / ha orless, 2050 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1750 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1450 g ai / ha or less, 1400 g ai / ha or less, 1350 g ai / ha or less, 1300 g ai / ha or less, 1250 g ai / ha or less, 1240 g ai / ha or less, 1200 g ai / ha or less, 1150 g ai / ha or less, 1100 g ai / ha or less, 1050 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 650 g ai / ha or less, 600 g ai / ha or less, 550 g ai / ha or less, 500 g ai / ha or less, 450 g ai / ha or less, 400 g ai / ha or less, 380 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 320 g ai / ha or less, 300 g ai / ha or less, 280 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 220 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 gai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, 55 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, or 15 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 12.5–4500 g ai / ha, 15–2250 g ai / ha, 20-2500 g ai / ha, 25–3150 g ai / ha, 30–900 g ai / ha, 45–4200 g ai / ha, 50–1200 g ai / ha, 50–4100 g ai / ha, 60–750 g ai / ha, 75–2100 g ai / ha, 100–4000 g ai / ha, 200–3600 g ai / ha, 250–3000 g ai / ha, 250–1000 g ai / ha,700–4250 g ai / ha, 800–1400 g ai / ha, or 1000–3700 g ai / ha. Glyphosate, Glufosinate, and Bilanafos In addition to the compounds according to Formula I, the compositions can includeglyphosate, glufosinate, bilanafos, an agriculturally acceptable salt thereof, or mixtures thereof. Attorney Docket: 212168-WO-SEC-1 In some aspects, compositions and methods of the present disclosure can includeglyphosate or an agriculturally acceptable salt thereof. Glyphosate, as well as methods of preparing glyphosate, are known in the art. Exemplary uses of glyphosate include its use for control of annual and perennial grasses and broadleaf weeds, particularly in crops that have been genetically modified to be tolerant of glyphosate. Exemplary chemical forms of glyphosate include, but are not limited to, for example, glyphosate potassium salt, glyphosate sodium salt, glyphosate monoammonium salt, glyphosate diammonium salt, glyphosate isopropylamine (IPA) salt, glyphosate monoethanolamine (MEA) salt, glyphosate monomethylamine (MMA) salt, and glyphosate dimethylamine (DMA) salt. As used herein, glyphosate salt or salt of glyphosate generally refers to the reaction product of glyphosate with a moiety that can act as a base. Typically, the reaction is an acid-base reaction. In some aspects, compositions and methods of the present disclosure can include glufosinate or an agriculturally acceptable salt thereof. Glufosinate, shown below, is 2-amino-4- (hydroxy(methyl)phosphinyl)butanoic acid. Exemplary uses of glufosinate include its use forcontrol of annual and perennial grasses and broadleaf weeds, particularly in crops that have been genetically modified to be tolerant of glufosinate. An exemplary salt of glufosinate is glufosinate- ammonium, which is also known as 2-amino-4-(hydroxy(methyl)phosphinyl)butanoic acid ammonium salt. Glufosinate-ammonium is registered for controlling a wide variety of broad- leaved weeds and grasses particularly in glufosinate-tolerant crops like canola, maize, soybean, rice, cotton, and sugar beet. As used herein, glufosinate salt or salt of glufosinate generally refers to the reaction product of glufosinate with a moiety that can act as a base. Typically, the reaction is an acid-base reaction.Other chemical forms of glufosinate include bilanafos, also known as bialaphos.Bilanafos also can be used in the salt form such as bilanafos sodium. Exemplary uses include its use to control annual and perennial broadleaf weeds and grasses. Photosystem II (PS II) Inhibitors to the compounds according to Formula I, the compositions can include a II (PS II) inhibitor herbicide or agriculturally acceptable salt or ester thereof.Photosystem II inhibitors inhibit photosynthesis by binding to the photosystem II complex in the chloroplast. Examples of photosystem II inhibitors include phenylcarbamate herbicides, pyridazinone herbicides, triazolinone herbicides, triazine herbicides, urea herbicides, uracil herbicides, amide herbicides, nitrile herbicides, and phenylpyridazine herbicides. In some aspects, the composition can include a PS II inhibitor herbicide selected from the group consisting of ametryne, amicarbazone, atrazine, bentazone, bromacil, bromofenoxim, Attorney Docket: 212168-WO-SEC-1 bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, ethiozin, fenuron, fluometuron, hexazinone, iodobonil, ioxynil, isocil, isomethiozin, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryne, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, trietazine, and combinations thereof. The PS II inhibitor herbicide or agriculturally acceptable salt or ester thereof can beapplied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, the PS II inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergenceor growth of vegetation in an amount of 5 grams active ingredient per hectare (g ai / ha) or more,such as 10 g ai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more,210 g ai / ha or more, 220 g ai / ha or more, 230 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha ormore, 260 g ai / ha or more, 270 g ai / ha or more, 280 g ai / ha or more, 290 g ai / ha or more, 300 g ai / ha or more, 320 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha or more, 380 g ai / ha or more, 400 g ai / ha or more, 420 g ai / ha or more, 440 g ai / ha or more, 460 g ai / ha ormore, 480 g ai / ha or more, 500 g ai / ha or more, 525 g ai / ha or more, 550 g ai / ha or more, 575 gai / ha or more, 600 g ai / ha or more, 625 g ai / ha or more, 650 g ai / ha or more, 675 g ai / ha or more, 700 g ai / ha or more, 725 g ai / ha or more, 750 g ai / ha or more, 775 g ai / ha or more, 800 g ai / ha or more, 825 g ai / ha or more, 850 g ai / ha or more, 875 g ai / ha or more, 900 g ai / ha or more, 925 g ai / ha or more, 950 g ai / ha or more, 975 g ai / ha or more, 1000 g ai / ha or more, 1100 g ai / ha or more, 1200 g ai / ha or more, 1300 g ai / ha or more, 1400 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha ormore, 2100 g ai / ha or more, 2200 g ai / ha or more, 2300 g ai / ha or more, 2400 g ai / ha or more, 2500g ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3300 g ai / ha or more, 3400g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3800 g ai / ha ormore, 3900 g ai / ha or more, 4000 g ai / ha or more, 5000 g ail / ha or more, 6000 g ai / ha or more, Attorney Docket: 212168-WO-SEC-1 8000 g ai / ha or more, or 9,000 g ai / ha or more; in an amount of 10,000 g ai / ha or less, such as 9,000 g ai / ha or less, 8000 g ai / ha or less, 6000 g ai / ha or less, 5000 g ai / ha or less, 4000 g ai / ha or less, 3900 g ai / ha or less, 3800 g ai / ha or less, 3700 g ai / ha or less, 3600 g ai / ha or less, 3500 g ai / ha or less, 3400 g ai / ha or less, 3300 g ai / ha or less, 3200 g ai / ha or less, 3100 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 g ai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 g ai / ha or less, 2400 g ai / ha or less, 2300 g ai / ha or less, 2200 g ai / ha or less, 2100 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1400 g ai / ha or less, 1300 g ai / ha or less, 1200 g ai / ha or less, 1100 g ai / ha or less, 1000 g ai / ha or less, 975 g ai / ha or less, 950 g ai / ha or less, 925 g ai / ha or less, 900 g ai / ha or less, 875 g ai / ha or less, 850 g ai / ha or less, 825 g ai / ha or less, 800 g ai / ha or less, 775 g ai / ha or less, 750 g ai / ha or less, 725 g ai / ha or less, 700 g ai / ha or less, 675 g ai / ha or less, 650 g ai / ha or less, 625 g ai / ha or less, 600 g ai / ha or less, 575 g ai / ha or less, 550 g ai / ha or less, 525 g ai / ha or less, 500 g ai / ha or less, 480 g ai / ha or less, 460 g ai / ha or less, 440 g ai / ha or less, 420 g ai / ha or less, 400 g ai / ha or less, 390 g ai / ha or less, 380 g ai / ha or less, 370 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 330 g ai / ha or less, 320 g ai / ha or less, 310 g ai / ha or less, 300 g ai / ha or less, 290 g ai / ha or less, 280 g ai / ha or less, 270 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 230 g ai / ha or less, 220 g ai / ha or less, 210 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, 55 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 15 g ai / ha or less, or 10 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 15–4000 g ai / ha, 100-3000 g ai / ha, 3000–8000 g ai / ha, 10–2900 g ai / ha, 250–8000 g ai / ha, 625–2700 g ai / ha, 1500–2600 g ai / ha, 725–4000 g ai / ha, 90–400 g ai / ha, 420 g ai / ha, 120–2100 g ai / ha, 10–200 g ai / ha, 250–1800 g ai / ha, 300–2600 g ai / ha, 370–2000 g ai / ha, 100–1000 g ai / ha, 500–900 g ai / ha, 85–440 g ai / ha, 600 g ai / ha, 95–950 g ai / ha, 35–2500 g ai / ha, 10–3000 g ai / ha, 350–2000 g 1000–3000 g ai / ha, 25–1600 g ai / ha, 220–2400 g ai / ha, 30–5000 g ai / ha, g ai / ha, 50–10,000 g ai / ha, 210–370 g ai / ha, 35–200 g ai / ha, 20–1500 g ai / ha, 70–400 g ai / ha, 60– 350 g ai / ha, 15–250 g ai / ha, 70–2000 g ai / ha, 100–700 g ai / ha, 80–900 g ai / ha, 100–2500 g ai / ha, or 150–800 g ai / ha. In some aspects, the photosystem II inhibitor or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 30-1000 g ai / ha. Attorney Docket: 212168-WO-SEC-1 4-Hydroxyphenyl-Pyruvate Dioxygenase (HPPD) Inhibitors In addition to the compounds according to Formula I, the compositions can include a 4- hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide. HPPD inhibitor herbicidesinterfere with an oxygenase enzyme involved in the creation of energy in plants and higher order eukaryotes. Examples of HPPD inhibitors include benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxachlortole, isoxaflutole, lancotrione, mesotrione, pyraquinate, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, or an agriculturally acceptable salt or ester thereof, and combinations thereof. In some aspects, the composition can include a HPPD inhibitor herbicide selected from the group consisting of benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxachlortole, isoxaflutole, lancotrione, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, an agriculturally acceptable salt or ester thereof, and combinations thereof. The HPPD inhibitor herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In someaspects, the HPPD inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai / ha or more, such as 1.1 g ai / ha or more, 1.25 g ai / ha or more, 1.5 g ai / ha or more, 1.75 g ai / ha or more, 2 g ai / ha or more, 2.5 g ai / ha or more, 3 g ai / ha or more, 3.5 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 21 g ai / ha or more, 22 g ai / ha ormore, 23 g ai / ha or more, 24 g ai / ha or more, 25 g ai / ha or more, 26 g ai / ha or more, 27 g ai / ha or more, 28 g ai / ha or more, 29 g ai / ha or more, 30 g ai / ha or more, 31 g ai / ha or more, 32 g ai / ha or more, 33 g ai / ha or more, 34 g ai / ha or more, 35 g ai / ha or more, 36 g ai / ha or more, 37 g ai / ha or more, 38 g ai / ha or more, 39 g ai / ha or more, 40 g ai / ha or more, 41 g ai / ha or more, 42 g ai / ha or more, 43 g ai / ha or more, 44 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha ormore, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 220 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 280 g ai / ha or more, 300 g ai / ha or more, 320 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g Attorney Docket: 212168-WO-SEC-1 ai / ha or more, 380 g ai / ha or more, 400 g ai / ha or more, 450 g ai / ha or more, 500 g ai / ha or more, 550 g ai / ha or more, 600 g ai / ha or more, 650 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more, 1000 g ai / ha or more, 1050 g ai / ha or more, 1100 g ai / ha or more, 1150 g ai / ha or more, 1200 g ai / ha or more, 1250 g ai / ha or more, 1300 g ai / ha or more, 1350 g ai / ha or more, 1400 g ai / ha or more, 1450 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2050 g ai / ha or more, 2100 g ai / ha or more, 2150 g ai / ha or more, 2200 g ai / ha or more, 2240 g ai / ha or more, 2250 g ai / ha or more, 2300 g ai / ha or more, 2350 g ai / ha or more, 2400 g ai / ha or more, 2450 g ai / ha or more, 2500 g ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2750 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3250 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3900 g ai / ha or more, 3950 g ai / ha or more, 4000 g ai / ha or more, 4100 g ai / ha or more, 4200 g ai / ha or more, 4250 g ai / ha or more, 4300 g ai / ha or more, or 4350 g ai / ha or more, or 4400 g ai / ha or more; in an amount of 4500 g ai / ha or less, such as 4450 g ai / ha or less, 4400 g ai / ha or less, 4350 g ai / ha or less, 4300 g ai / ha or less, 4250 g ai / ha or less, 4100 g ai / ha or less, 4000 g ai / ha or less, 3950 g ai / ha or less, 3900 g ai / ha or less, 3800 g ai / ha or less, 3750 g ai / ha or less, 3700 g ai / ha or less, 3600 g ai / ha or less, 3500 g ai / ha or less, 3400 g ai / ha or less, 3300 g ai / ha or less, 3250 g ai / ha or less, 3200 g ai / ha or less, 3100 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 g ai / ha or less, 2750 g ai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 g ai / ha or less, 2450 g ai / ha or less, 2400 g ai / ha or less, 2350 g ai / ha or less, 2300 g ai / ha or less, 2250 g ai / ha or less, 2240 g ai / ha or less, 2200 g ai / ha or less, 2150 g ai / ha or less, 2100 g ai / ha or less, 2050 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1750 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1450 g ai / ha or less, 1400 g ai / ha or less, 1350 g ai / ha or less, 1300 g ai / ha or less, 1250 g ai / ha or less, 1240 g ai / ha or less, 1200 g ai / ha or less, 1150 g ai / ha or less, 1100 g ai / ha or less, 1050 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 650 g ai / ha or less, 600 g ai / ha or less, 550 g ai / ha or less, 500 g ai / ha or less, 450 g ai / ha or less, 400 g ai / ha or less, 380 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 320 g ai / ha or less, 300 g ai / ha or less, 280 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 220 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, 55 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 44 g ai / ha or less, 43 g ai / ha or less, 42 g ai / ha or less, 41 g Attorney Docket: 212168-WO-SEC-1 ai / ha or less, 40 g ai / ha or less, 39 g ai / ha or less, 38 g ai / ha or less, 37 g ai / ha or less, 36 g ai / ha or less, 35 g ai / ha or less, 34 g ai / ha or less, 33 g ai / ha or less, 32 g ai / ha or less, 31 g ai / ha or less, 30 g ai / ha or less, 29 g ai / ha or less, 28 g ai / ha or less, 27 g ai / ha or less, 26 g ai / ha or less, 25 g ai / ha or less, 24 g ai / ha or less, 23 g ai / ha or less, 22 g ai / ha or less, 21 g ai / ha or less, 20 g ai / ha or less, 19 g ai / ha or less, 18 g ai / ha or less, 17 g ai / ha or less, 16 ai / ha or less, 15 g ai / ha or less, 14 g ai / haor less, 13 g ai / ha or less, 12 g ai / ha or less, 11 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, 8 g ai / ha or less, 7 g ai / ha or less, 6 g ai / ha or less, 5 g ai / ha or less, 4 g ai / ha or less, 3.5 g ai / ha or less, 3 g ai / ha or less, 2.5 g ai / ha or less, 2 g ai / ha or less, 1.75 g ai / ha or less, 1.5 g ai / ha or less, 1.25 g ai / ha or less, or 1.1 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 1–4500 g ai / ha, 4–3900 g ai / ha, 1.75-2500 g ai / ha, 75–3100 g ai / ha, 90–900 g ai / ha, 55–4200 g ai / ha, 50–2350 g ai / ha, 80– 2900 g ai / ha, 120–4100 g ai / ha, 65–2700 g ai / ha, 300–4000 g ai / ha, 1200–3600 g ai / ha, 250–2000 g ai / ha, 1.75-250 g ai / ha, 700–4250 g ai / ha, 39–1100 g ai / ha, or 1.1–4450 g ai / ha. Acetyl CoA Carboxylase (ACCase) Inhibitors In addition to the compounds according to Formula I, the compositions can include anacetyl CoA carboxylase (ACCase) inhibitor herbicide or an agriculturally acceptable salt or esterthereof. ACCase inhibitor herbicides inhibit lipid biosynthesis in the plant. Examples of ACCaseinhibitor herbicides include aryloxyphenoxypropionates, cyclohexanediones, andphenylpyrazolines. In some aspects, the ACCase inhibitor herbicide can include anaryloxyphenoxypropionate herbicide. In some aspects, the ACCase inhibitor herbicide can includea cyclohexanedione herbicide. In some aspects, the ACCase inhibitor herbicide can include aphenylpyrazoline herbicide. In some aspects, the composition can include an ACCase inhibitor selected from the group of cyclohexanediones, aryloxyphenoxypropionates, phenylpyrazolines, or combinations thereof. In some cases, the composition can include clodinafop, cyhalofop, diclofop, fenoxaprop, fenthiaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, agriculturally acceptable salts or esters thereof, or combinations thereof. In some cases, the composition can include, alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, pyriflubenzoxim, sethoxydim, tepraloxydim, tralkoxydim, agriculturally acceptable salts or esters thereof, or combinations thereof. In some cases, the composition can include pinoxaden. In some aspects, the composition can include an ACCase inhibitor herbicide selected from the group consisting of alloxydim, butroxydim, clethodim, clodinafop, cloproxydim, cycloxydim, cyhalofop, diclofop, fenoxaprop, fenthiaprop, fluazifop, haloxyfop, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim, tralkoxydim,agriculturally acceptable salts and esters thereof, and combinations thereof. Attorney Docket: 212168-WO-SEC-1 The ACCase inhibitor herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In someaspects, the ACCase inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2 g ai / ha or more, such as 2.5 g ai / ha or more, 3 g ai / ha or more, 3.5 g ai / ha or more, 4 g ai / ha or more, 4.5 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more,70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more,95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 220 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 280 g ai / ha or more, 300 g ai / ha or more, 320 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha or more, 380 g ai / ha or more, 400 g ai / ha or more, 450 g ai / ha or more, 500 g ai / ha or more, 550 g ai / ha or more, 600 g ai / ha or more, 650 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more, 1000 g ai / ha or more, 1050 g ai / ha or more, 1100 g ai / ha or more, 1150 g ai / ha or more, 1200 g ai / ha or more, 1250 g ai / ha or more, 1300 g ai / ha or more, 1350 g ai / ha or more, 1400 g ai / ha or more, or 1450 g ai / ha or more; in an amount of 1500 g ai / ha or less, such as 1450 g ai / ha or less, 1400 g ai / ha or less, 1350 g ai / ha or less, 1300 g ai / ha or less, 1250 g ai / ha or less, 1240 g ai / ha or less, 1200 g ai / ha or less, 1150 g ai / ha or less, 1100 gai / ha or less, 1050 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 650 g ai / ha or less, 600 gai / ha or less, 550 g ai / ha or less, 500 g ai / ha or less, 450 g ai / ha or less, 400 g ai / ha or less, 380 gai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 320 g ai / ha or less, 300 g ai / ha or less, 280 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 220 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 110 gai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / haor less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, 55 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 15 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, 8 g ai / ha or less, 7 g ai / ha or less, 6 g ai / ha or less, 5 g ai / ha or less, 4.5 g ai / ha or less, 4 g ai / ha or less, 3.5 g ai / ha or less, 3 g ai / ha or less, or 2.5 g ai / ha or less; or in an amount ranging from any of the Attorney Docket: 212168-WO-SEC-1 minimum values described above to any of the maximum values described above, such as 2-1500 g ai / ha, 5–1300 g ai / ha, 6-250 g ai / ha, 75–1240 g ai / ha, 90–900 g ai / ha, 55–290 g ai / ha, 7–600 g ai / ha, 20–700 g ai / ha, 190–1450 g ai / ha, 65–1100 g ai / ha, 320–1000 g ai / ha, 250–750 g ai / ha, 700– 1200 g ai / ha, 850–1400 g ai / ha, or 2.5–1450 g ai / ha. Plant Growth Regulator (PGR) In addition to the compounds according to Formula I, the compositions can include aplant growth regulator (PGR), an agriculturally acceptable salt or ester thereof, or mixtures thereof. PGRs, also called plant hormones, function as chemical messengers for intercellularcommunication. PGRs can be classified into several modes of action that may influence, forexample, the growth, division, elongation, or differentiation of plant cells. Examples of PGRs include 1,4-dimethylnapththalene, 1-methylcyclopropene, 1-napthylacetic acid, 2,6- diisopropylnaphthalene, 2-naphthyloxyacetic acid, 4-chlorophenoxyacetic acid (4-CPA), 6- benzylaminopurine, abscisic acid, amidochlor, ancymidol, aviglycine, butralin, carbaryl, chlorflurenol, chlormequat, chlorphonium chloride, chlorpropham, clofencet, cloprop, cloxyfonac, cuprous chloride, cyanamide, cyclanilide, cycloheximide, cytokinins, daminozide, decan-1-ol, dikegulac, dimethipin, dimexano, endothal, etacelasil, ethephon, ethychlozate, fenoprop, fenridazon, flumetralin, flurenol, flurprimidol, forchlorfenuron, gibberellins, glyphosine, heptamaloxyloglucan, heptopargil, hexafluoroacetone trihydrate, inabenfide, indol-3-butyric acid (IBA), indol-3-ylacetic acid (IAA), isoprothiolane, maleic hydrazide, mefluidide, mepiquat, N- acetylthiazolidine-4-carboxylic acid, naphthaleneacetamide, N-m-tolylphthalamic acid, N- phenylphthalamic acid, nitrophenolates, paclobutrazol, pelargonic acid, piproctanyl bromide, prohexadione, prohydrojasmon, propham, propyl-3-tert-butylphenoxyacetate, sintofen, tetcyclacis, thidiazuron, triacontanol, triapenthenol, trinexapac, and uniconazole. In some aspects, the composition can include a PGR selected from the group consisting of 1,4-dimethylnapththalene, 1-methylcyclopropene, 1-napthylacetic acid, 2,6- diisopropylnaphthalene, 2-naphthyloxyacetic acid, 4-chlorophenoxyacetic acid (4-CPA), 6- benzylaminopurine, abscisic acid, amidochlor, ancymidol, aviglycine, butralin, carbaryl, chlorflurenol, chlormequat, chlorphonium chloride, chlorpropham, clofencet, cloprop, cloxyfonac, cuprous chloride, cyanamide, cyclanilide, cycloheximide, cytokinins, daminozide, decan-1-ol, dikegulac, dimethipin, dimexano, endothal, etacelasil, ethephon, ethychlozate, fenoprop, fenridazon, flumetralin, flurenol, flurprimidol, forchlorfenuron, gibberellins, glyphosine, heptamaloxyloglucan, heptopargil, hexafluoroacetone trihydrate, inabenfide, indol-3-butyric acid (IBA), indol-3-ylacetic acid (IAA), isoprothiolane, maleic hydrazide, mefluidide, mepiquat, N- acetylthiazolidine-4-carboxylic acid, naphthaleneacetamide, N-m-tolylphthalamic acid, N- phenylphthalamic acid, nitrophenolates, paclobutrazol, pelargonic acid, piproctanyl bromide, Attorney Docket: 212168-WO-SEC-1 prohexadione, prohydrojasmon, propham, propyl-3-tert-butylphenoxyacetate, sintofen, tetcyclacis, thidiazuron, triacontanol, triapenthenol, trinexapac, uniconazole, agriculturally acceptable salts or esters thereof, and mixtures thereof. PGRs can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, the PGR is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amountof 0.020 g ai / ha or more, such as 0.025 g ai / ha or more, 0.03 g ai / ha or more, 0.04 g ai / ha or more,0.05 g ai / ha or more, 0.06 g ai / ha or more, 0.07 g ai / ha or more, 0.08 g ai / ha or more, 0.09 g ai / haor more, 0.1 g ai / ha or more, 0.11 g ai / ha or more, 0.125 g ai / ha or more, 0.15 g ai / ha or more, 0.175 g ai / ha or more, 0.20 g ai / ha or more, 0.25 g ai / ha or more, 0.3 g ai / ha or more, 0.4 g ai / ha or more, 0.5 g ai / ha or more, 0.6 g ai / ha or more, 0.7 g ai / ha or more, 0.8 g ai / ha or more, 0.9 g ai / ha or more, 1 g ai / ha or more, 1.1 g ai / ha or more, 1.25 g ai / ha or more, 1.5 g ai / ha or more, 1.75 g ai / ha or more, 2 g ai / ha or more, 2.25 g ai / ha or more, 2.5 g ai / ha or more, 2.75 g ai / ha or more, 3 g ai / ha or more, 3.25 g ai / ha or more, 3.5 g ai / ha or more, 3.75 g ai / ha or more, 4 g ai / ha or more, 4.25 g ai / ha or more, 4.5 g ai / ha or more, 4.75 g ai / ha or more, 5 g ai / ha or more, 5.25 g ai / ha or more, 5.5 g ai / ha or more, 5.75 g ai / ha or more, 6 g ai / ha or more, 6.25 g ai / ha or more, 6.5 g ai / ha or more, 6.75 g ai / ha or more, 7 g ai / ha or more, 7.25 g ai / ha or more, 7.5 g ai / ha or more, 8 g ai / haor more, 8.5 g ai / ha or more, 9 g ai / ha or more, 9.5 g ai / ha, or more, 10 g ai / ha or more, 15 g ai / haor more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 175 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 210 g ai / ha or more, 220 g ai / ha or more, 225 g ai / ha or more, 230 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 270 g ai / ha or more, 275 g ai / ha or more, 280 g ai / ha or more, 290 g ai / ha or more, 300 g ai / ha or more, 310 g ai / ha or more, 320 g ai / ha or more, 325 g ai / ha or more, 330 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha or more, 370 g ai / ha or more, 375 g ai / ha or more, 380 g ai / ha or more, 390 g ai / ha or more, 400 g ai / ha or more, 410 g ai / ha or more, 420 g ai / ha or more, 425 g ai / ha or more, 430 g ai / ha or more, 440 g ai / ha or more, 450 g ai / ha or more, 460 g ai / ha or more, 470 g ai / ha or more, 475 g ai / ha or more, 480 g ai / ha or more, 490 g ai / ha or more, 500 g ai / ha or more, 525 g ai / ha or more, 550 g ai / ha or more, 575 g ai / ha or more, 600 g ai / ha or more, 625 g ai / ha or more, 650 g ai / ha ormore, 675 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g Attorney Docket: 212168-WO-SEC-1 ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more, 1000 g ai / ha or more, 1050 g ai / ha or more, 1100 g ai / ha or more, 1150 g ai / ha or more, 1200 g ai / ha or more, 1250 g ai / ha or more, 1300 g ai / ha or more, 1350 g ai / ha or more, 1400 g ai / ha or more, 1450 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2100 g ai / ha or more, 2200 g ai / ha or more, 2300 g ai / ha or more, 2400 g ai / ha or more, 2500 g ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3250 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3750 g ai / ha or more, 4000 g ai / ha or more, 4250 g ai / ha or more, 4500 g ai / ha or more, 4750 g ai / ha or more, 5000 g ai / ha or more, 5250 g ai / ha or more, 5500 g ai / ha or more, 5750 g ai / ha or more, 6000 g ai / ha or more, 6500 g ai / ha or more, 7000 g ai / ha or more, 7500 g ai / ha or more, 8000 g ai / ha or more, 8500 g ai / ha or more, 9000 g ai / ha or more, 9500 g ai / ha or more, or 10 kg ai / ha or more; in an amount of 11 kg ai / ha or less, such as 10 kg ai / ha or less, 9500 g ai / ha or less, 9000 g ai / ha or less, 8500 g ai / ha or less, 8000 g ai / ha or less, 7500 g ai / ha or less, 7000 g ai / ha or less, 6500 g ai / ha or less, 6000 g ai / ha or less, 5750 g ai / ha or less, 5500 g ai / ha or less, 5250 g ai / ha or less, 5000 g ai / ha or less, 4750 g ai / ha or less, 4500 g ai / ha or less, 4250 g ai / ha or less, 4000 g ai / ha or less, 3750 g ai / ha or less, 3500 g ai / ha or less, 3400 g ai / ha or less, 3300 g ai / ha or less, 3250 g ai / ha or less, 3200 g ai / ha or less, 3100 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 g ai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 g ai / ha or less, 2400 g ai / ha or less, 2300 g ai / ha or less, 2200 g ai / ha or less, 2100 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1400 g ai / ha or less, 1350 g ai / ha or less, 1300 g ai / ha or less, 1250 g ai / ha or less, 1200 g ai / ha or less, 1150 g ai / ha or less, 1100 g ai / ha or less, 1050 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 675 g ai / ha or less, 650 g ai / ha or less, 625 g ai / ha or less, 600 g ai / ha or less, 575 g ai / ha or less, 550 g ai / ha or less, 525 g ai / ha or less, 500 g ai / ha or less, 490 g ai / ha or less, 480 g ai / ha or less, 475 g ai / ha or less, 470 g ai / ha or less, 460 g ai / ha or less, 450 g ai / ha or less, 440 g ai / ha or less, 430 g ai / ha or less, 425 g ai / ha or less, 420 g ai / ha or less, 410 g ai / ha or less, 400 g ai / ha or less, 390 g ai / ha or less, 380 g ai / ha or less, 375 g ai / ha or less, 370 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 330 g ai / ha or less, 325 g ai / ha or less, 320 g ai / ha or less, 310 g ai / ha or less, 300 g ai / ha or less, 290 g ai / ha or less, 280 g ai / ha or less, 275 g ai / ha or less, 270 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 230 g ai / ha or less, 225 g ai / ha or less, 220 g ai / ha or less, 210 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 175 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, Attorney Docket: 212168-WO-SEC-1 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, 55 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha orless, 15 g ai / ha or less, 10 g ai / ha or less, 9.5 g ai / ha or less, 9 g ai / ha or less, 8.5 g ai / ha or less, 8 g ai / ha or less, 7.5 g ai / ha or less, 7.25 g ai / ha or less, 7 g ai / ha or less, 6.75 g ai / ha or less, 6.5 g ai / ha or less, 6.25 g ai / ha or less, 6 g ai / ha or less, 5.75 g ai / ha or less, 5.5 g ai / ha or less, 5.25 g ai / ha or less, 5 g ai / ha or less, 4.75 g ai / ha or less, 4.5 g ai / ha or less, 4.25 g ai / ha or less, 4 g ai / ha or less, 3.75 g ai / ha or less, 3.5 g ai / ha or less, 3.25 g ai / ha or less, 3 g ai / ha or less, 2.75 g ai / ha or less, 2.5 g ai / ha or less, 2.25 g ai / ha or less, 2 g ai / ha or less, 1.75 g ai / ha or less, 1.5 g ai / ha or less, 1.25 g ai / ha or less, 1.1 g ai / ha or less, 1 g ai / ha or less, 0.9 g ai / ha or less, 0.8 g ai / ha or less, 0.7 g ai / ha or less, 0.6 g ai / ha or less, 0.5 g ai / ha or less, 0.4 g ai / ha or less, 0.3 g ai / ha or less, 0.2 g ai / ha or less, 0.175 g ai / ha or less, 0.15 g ai / ha or less, 0.125 g ai / ha or less, 0.11 g ai / ha or less, 0.1 g ai / ha or less, 0.09 g ai / ha or less, 0.08 g ai / ha or less, 0.07 g ai / ha or less, 0.06 g ai / ha or less, 0.05 g ai / ha or less, 0.04 g ai / ha or less, 0.03 g ai / ha or less, or 0.025 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 0.020 g – 11 kg ai / ha, 950–6500 g ai / ha, 7–250 g ai / ha, 460–3750 g ai / ha, 600–2500g ai / ha, 50–5000 g ai / ha, 110–450 g ai / ha, 15-160 g ai / ha, 1900–4000 g ai / ha, 1–4 g ai / ha, 750–2200 g ai / ha, 380–5250 g ai / ha, 0.2–17.25 g ai / ha, 500–1400 g ai / ha, 3.25–950 g ai / ha, 440–2900 g ai / ha, or 0.025 –250 g ai / ha. Very Long Chain Fatty Acid Synthesis (VLCFA) Inhibitors In addition to the compounds according to Formula I, the compositions can include avery long chain fatty acid (VLCFA) synthesis inhibitor herbicide. Very long chain fatty acids havemultiple functions in the plant, primarily serving as precursors of cuticle wax biosynthesis, and as components of storage lipids, sphingolipids and phospholipids. Examples of VLCFA synthesis inhibitors include, but are not limited to, acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fentrazamide, flufenacet, ipfencarbazone, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor. In some aspects, the composition can include a VLCFA synthesis inhibitor herbicide selected from the group consisting of acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fentrazamide, flufenacet, ipfencarbazone, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, thenylchlor, agriculturally acceptable salts and esters thereof, and combinations thereof. The VLCFA synthesis inhibitor herbicide or agriculturally acceptable salt or ester can be applied to vegetation or an area adjacent the vegetation or applied to soil or water Attorney Docket: 212168-WO-SEC-1 to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, the VLCFA synthesis inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 40 gram active ingredient per hectare (g ai / ha) or more, such as 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 220 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 280 g ai / ha or more, 300 g ai / ha or more, 320 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha or more, 380 g ai / ha or more, 400 g ai / ha or more, 450 g ai / ha or more, 500 g ai / ha or more, 550 g ai / ha or more, 600 g ai / ha or more, 650 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more, 1000 g ai / ha or more, 1050 g ai / ha or more, 1100 g ai / ha or more, 1150 g ai / ha or more, 1200 g ai / ha or more, 1250 g ai / ha or more, 1300 g ai / ha or more, 1350 g ai / ha or more, 1400 g ai / ha or more, 1450 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2050 g ai / ha or more, 2100 g ai / ha or more, 2150 g ai / ha or more, 2200 g ai / ha or more, 2240 g ai / ha or more, 2250 g ai / ha or more, 2300 g ai / ha or more, 2350 g ai / ha or more, 2400 g ai / ha or more, 2450 g ai / ha or more, 2500 g ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2750 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3250 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3900 g ai / ha or more, 3950 g ai / ha or more, 4000 g ai / ha or more, 4100 g ai / ha or more, 4200 g ai / ha or more, 4250 g ai / ha or more, 4300 g ai / ha or more, 4400 g ai / ha or more, 4450 g ai / ha or more, 4500 g ai / ha or more, 4640 g ai / ha or more, 4780 g ai / ha or more, 4920 g ai / ha or more, 5000 g ai / ha or more, 5060 g ai / ha or more, 5200 g ai / ha or more, 5340 g ai / ha or more, 5480 g ai / ha or more, 5620 g ai / ha or more, 5760 g ai / ha or more, 5900 g ai / ha or more, 6040 g ai / ha or more, 6180 g ai / ha or more, 6320 g ai / ha or more, 6460 g ai / ha or more, or 6600 g ai / ha or more; in an amount of 6720 g ai / ha or less, such as 6645 g ai / ha or less, 6575 g ai / ha or less, 6500 g ai / ha or less, 6425 g ai / ha or less, 6350 g ai / ha or less, 6275 g ai / ha or less, 6200 g ai / ha or less, 6125 g ai / ha or less, 6050 g ai / ha or less, 5975 g ai / ha or less, 5900 g ai / ha or less, 5825 g ai / ha or less, 5750 g ai / ha or less, 5675 g ai / ha or less, 5600 g ai / ha or less, 5525 g ai / ha or less, 5450 g ai / ha or less, 5375 g ai / ha or less, 5300 g ai / ha or less, 5225 g ai / ha or less, 5150 g ai / ha or less, 5075 g ai / ha or less, 5000 g ai / ha or less, 4925 g ai / ha or less, 4850 g ai / ha or less, 4775 g ai / ha or less, 4700 g ai / ha or less, 4625 g ai / ha or less, 4550 g ai / ha or less, 4475 g Attorney Docket: 212168-WO-SEC-1 ai / ha or less, 4450 g ai / ha or less, 4400 g ai / ha or less, 4300 g ai / ha or less, 4250 g ai / ha or less,4100 g ai / ha or less, 4000 g ai / ha or less, 3950 g ai / ha or less, 3900 g ai / ha or less, 3800 g ai / ha or less, 3750 g ai / ha or less, 3700 g ai / ha or less, 3600 g ai / ha or less, 3500 g ai / ha or less, 3400 g ai / ha or less, 3300 g ai / ha or less, 3250 g ai / ha or less, 3200 g ai / ha or less, 3100 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 g ai / ha or less, 2750 g ai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 g ai / ha or less, 2450 g ai / ha or less, 2400 g ai / ha or less, 2350 g ai / ha or less, 2300 g ai / ha or less, 2250 g ai / ha or less, 2240 g ai / ha or less, 2200 g ai / ha or less, 2150 g ai / ha or less, 2100 g ai / ha or less, 2050 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1750 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1450 g ai / ha or less, 1400 g ai / ha or less, 1350 g ai / ha or less, 1300 g ai / ha or less, 1250 g ai / ha or less, 1240 g ai / ha or less, 1200 g ai / ha or less, 1150 g ai / ha or less, 1100 g ai / ha or less, 1050 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 650 g ai / ha or less, 600 g ai / ha or less, 550 g ai / ha or less, 500 g ai / ha or less, 450 g ai / ha or less, 400 g ai / ha or less, 380 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 320 g ai / ha or less, 300 g ai / ha or less, 280 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 220 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, 55 g ai / ha or less, 50 gai / ha or less, or 45 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 40–6720 g ai / ha, 45–5825 g ai / ha, 60-2500 g ai / ha, 75–3100 g ai / ha, 90–900 g ai / ha, 55–4200 g ai / ha, 50–6050 g ai / ha, 80– 4700 g ai / ha, 120–4775 g ai / ha, 65–2100 g ai / ha, 300–4000 g ai / ha, 1200–3600 g ai / ha, 250–5000 g ai / ha, 250–1000 g ai / ha, 700–4250 g ai / ha, 800–1400 g ai / ha, or 1000–6720 g ai / ha.Microtubule Assembly Inhibitors (MAI)In addition to the according to Formula I, the compositions can include a microtubule assembly inhibitor an agriculturally acceptable salt or ester thereof, or mixtures thereof. MAI herbicides may inhibit plant cell division by binding to tubulin, the major protein needed to form the microtubules required in cell division. Examples of MAI herbicides include benfluralin, butamifos, butralin, carbetamide, chlorpropham, chlorthal, dithiopyr, ethalfluralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, thiazopyr, trifluralin, and agriculturally acceptable salts or esters thereof. MAI herbicides can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce Attorney Docket: 212168-WO-SEC-1 a herbicidal effect. In some aspects, the MAI herbicide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai / ha or more, such as 105 g ai / ha or more, 110 g ai / ha or more, 115 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 135 g ai / ha or more, 140 g ai / ha or more, 145 g ai / ha or more, 150 g ai / ha or more, 155 g ai / ha or more, 160 g ai / ha or more, 165 g ai / ha or more, 170 g ai / ha or more, 175 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 210 g ai / ha or more, 220 g ai / ha or more, 225 g ai / ha or more, 230 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 270 g ai / ha or more, 275 g ai / ha or more, 280 g ai / ha or more, 290 g ai / ha or more, 300 g ai / ha or more, 310 g ai / ha or more, 320 g ai / ha or more, 325 g ai / ha or more, 330 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha or more, 370 g ai / ha or more, 375 g ai / ha or more, 380 g ai / ha or more, 390 g ai / ha or more, 400 g ai / ha or more, 500 g ai / ha or more, 600 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 900 g ai / ha or more, 1000 g ai / ha or more, 1100 g ai / ha or more, 1200 g ai / ha or more, 1300 g ai / ha or more, 1400 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2100 g ai / ha or more, 2200 g ai / ha or more, 2300 g ai / ha or more, 2400 g ai / ha or more, 2500 g ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3750 g ai / ha or more, 4000 g ai / ha or more, 4250 g ai / ha or more, 4500 g ai / ha or more, 4750 g ai / ha or more, 5000 g ai / ha or more, 5250 g ai / ha or more, 5500 g ai / ha or more, 5750 g ai / ha or more, 6000 g ai / ha or more, 6500 g ai / ha or more, 7000 g ai / ha or more, 7500 g ai / ha or more, 8000 g ai / ha or more, 8500 g ai / ha or more, 9000 g ai / ha or more, 9500 g ai / ha or more, or 10 kg ai / ha or more; in an amount of 10.5 kg ai / ha or less, such as 10 kg ai / ha or less, 9500 g ai / ha or less, 9000 g ai / ha or less, 8500 g ai / ha or less, 8000 g ai / ha or less, 7500 g ai / ha or less, 7000 g ai / ha or less, 6500 g ai / ha or less, 6000 g ai / ha or less, 5750 g ai / ha or less, 5500 g ai / ha or less, 5250 g ai / ha or less, 5000 g ai / ha or less, 4750 g ai / ha or less, 4500 g ai / ha or less, 4250 g ai / ha or less, 4000 g ai / ha or less, 3750 g ai / ha or less, 3600 g ai / ha or less, 3500 g ai / ha or less, 3400 g ai / ha or less, 3300 g ai / ha or less, 3200 g ai / ha or less, 3100 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 g ai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 g ai / ha or less, 2400 g ai / ha or less, 2300 g ai / ha or less, 2200 g ai / ha or less, 2100 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1400 g ai / ha or less, 1300 g ai / ha or less, 1200 g ai / ha or less, 1100 g ai / ha or less, 1000 g ai / ha or less, 900 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 600 g ai / ha or less, 500 g ai / ha or less, 400 g ai / ha or less, 390 g ai / ha or less, 380 g ai / ha or less, 375 g ai / ha or less, 370 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 330 g ai / ha or less, 325 g ai / ha or less, 320 g ai / ha or Attorney Docket: 212168-WO-SEC-1 less, 310 g ai / ha or less, 300 g ai / ha or less, 290 g ai / ha or less, 280 g ai / ha or less, 275 g ai / ha or less, 270 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 230 g ai / ha or less, 225 g ai / ha or less, 220 g ai / ha or less, 210 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 175 g ai / ha or less, 170 g ai / ha or less, 165 g ai / ha or less, 160 g ai / ha or less, 155 g ai / ha or less, 150 g ai / ha or less, 145 g ai / ha or less, 140 g ai / ha or less, 135 g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 115 g ai / ha or less, 110 g ai / ha or less, or 105 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, e.g., 100 g –10.5 kg ai / ha, 350–1800 g ai / ha,160–3750 g ai / ha, 225–2500 g ai / ha, 375–1400 g ai / ha, 115–350 g ai / ha, 3400–6750 g ai / ha, 185– 8000 g ai / ha, 390–3100 g ai / ha, 2000–4250 g ai / ha, 1200–3300 g ai / ha, or 250–600 g ai / ha.Fatty Acid and Lipid Synthesis (FA / LSI) InhibitorsIn addition to the compounds according to Formula I, the compositions can include a fatty acid and lipid synthesis inhibitor (FA / LSI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof. FA / LSI herbicides appear to interfere with the biosynthesis of fatty acids and lipids, thereby reducing the deposition of cuticle wax, and to cause abnormal cell development or to inhibit cell division in germinating seedlings. Examples of FA / LSI herbicides include benfuresate, bensulide, butylate, cycloate, dalapon, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, prosulfocarb, thiobencarb, tiocarbazil, tri-allate, vernolate. In some aspects, the composition can include a FA / LSI herbicide selected from the group consisting of benfuresate, bensulide, butylate, cycloate, dalapon, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, prosulfocarb, thiobencarb, tiocarbazil, tri-allate, vernolate, agriculturally acceptable salts or esters thereof, and mixtures thereof. FA / LSI herbicides can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, the FA / LSI herbicide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ai / ha or more, such as 310 g ai / ha or more, 320 g ai / ha or more, 325 g ai / ha or more, 330 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha ormore, 370 g ai / ha or more, 375 g ai / ha or more, 380 g ai / ha or more, 390 g ai / ha or more, 400 g ai / ha or more, 410 g ai / ha or more, 420 g ai / ha or more, 425 g ai / ha or more, 430 g ai / ha or more, 440 g ai / ha or more, 450 g ai / ha or more, 460 g ai / ha or more, 470 g ai / ha or more, 475 g ai / ha or more, 480 g ai / ha or more, 490 g ai / ha or more, 500 g ai / ha or more, 525 g ai / ha or more, 550 g ai / ha or more, 575 g ai / ha or more, 600 g ai / ha or more, 625 g ai / ha or more, 650 g ai / ha or more, 675 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more,1000 g ai / ha or more, 1100 g ai / ha or more, 1200 g Attorney Docket: 212168-WO-SEC-1 ai / ha or more, 1300 g ai / ha or more, 1400 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2100 gai / ha or more, 2200 g ai / ha or more, 2300 g ai / ha or more, 2400 g ai / ha or more, 2500 g ai / ha ormore, 2600 g ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3250 g ai / ha or more, 3500 g ai / ha or more, 3750 g ai / ha or more, 4000 g ai / ha or more, 4250 g ai / ha or more, 4500 g ai / ha or more, 4750 g ai / ha or more, 5000 g ai / ha or more, 5250 g ai / ha or more, 5500 g ai / ha or more, 5750 g ai / ha or more, 6000 g ai / ha or more, 6250 g ai / ha or more, 6500 g ai / ha or more, 6750 g ai / ha or more, 7000 g ai / ha or more, 7500 g ai / ha or more, 8000 gai / ha or more, 8500 g ai / ha or more, 9000 g ai / ha or more, 9500 g ai / ha or more, 10 kg ai / ha ormore, 10.5 kg ai / ha or more, 11 kg ai / ha or more, or 11.5 kg ai / ha or more; in an amount of 12 kgai / ha or less, such as 11.5 kg ai / ha or less, 11 kg ai / ha or less, 10.5 kg ai / ha, 10 kg ai / ha or less, 9500 g ai / ha or less, 9000 g ai / ha or less, 8500 g ai / ha or less, 8000 g ai / ha or less, 7500 g ai / ha or less, 7000 g ai / ha or less, 6750 g ai / ha or less, 6500 g ai / ha or less, 6250 g ai / ha or less, 6000 g ai / ha or less, 5750 g ai / ha or less, 5500 g ai / ha or less, 5250 g ai / ha or less, 5000 g ai / ha or less, 4750 g ai / ha or less, 4500 g ai / ha or less,4250 g ai / ha or less, 4000 g ai / ha or less, 3750 g ai / ha or less, 3500 g ai / ha or less, 3250 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 gai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 g ai / ha or less, 2400 g ai / ha or less, 2300 g ai / ha or less, 2200 g ai / ha or less, 2100 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1400 g ai / ha or less, 1300 g ai / ha or less, 1200 g ai / ha or less, 1100 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 675 g ai / ha or less, 650 g ai / ha or less, 625 g ai / ha or less, 600 g ai / ha or less, 575 g ai / ha or less, 550 g ai / ha or less, 525 g ai / ha or less, 500 g ai / ha or less, 490 g ai / ha or less, 480 g ai / ha or less, 475 g ai / ha or less, 470 g ai / ha or less, 460 g ai / ha or less, 450 g ai / ha or less, 440 g ai / ha or less, 430 g ai / ha or less, 425 g ai / ha or less, 420 g ai / ha or less, 410 g ai / ha or less, 400 g ai / ha or less, 390 g ai / ha or less, 380 g ai / ha or less, 375 g ai / ha or less, 370 g ai / ha or less,360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 330 g ai / ha or less, 325 g ai / ha or less, 320 g ai / ha or less, or 310 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 300 g–12 kg ai / ha, 950–4500 g ai / ha, 460–3750 g ai / ha, 10–12 kg ai / ha, 900–1700 g ai / ha, 320–450 g ai / ha, 8500 g–10 kgai / ha, 750–2200 g ai / ha, 390–5250 g ai / ha, 400–1200 g ai / ha, 250-1250 g ai / ha, 1200–3500 g ai / ha,or 310 g–10 kg ai / ha.More Recent Herbicides In addition to the compounds according to Formula I, the compositions can include another herbicide or an agriculturally acceptable salt or ester thereof, as identified herein. These Attorney Docket: 212168-WO-SEC-1 more recent herbicides include broclozone, flufenoximacil, flusulfinam, icafolin, iptriazopyrid, and metproxybicyclone. Broclozone, the ISO name for 2-[(2-bromo-4-chlorophenyl)methyl]-4,4-dimethyl-3- isoxazolidinone (CAS No.2766607-82-1), is a DOXP-inhibiting oxazole herbicide from Qingdao KingAgroot Chemical Compound Co. and is disclosed in WO202302027. Broclozone may be used with foliar and / or soil applications, and may be used on crops such as wheat, soybeans, peanuts, oilseed rape, cabbage, rice, cotton, garlic, and watermelon. Flufenoximacil, the ISO name for methyl (2R)-2-[[(E)-[[2-chloro-5-[3,6-dihydro-3- methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4- fluorophenyl]methylene]amino]oxy]-propanoate (CAS No. 2759011-88-4), is a phenyluracil herbicide for non-selective weed control from Qingdao KingAgroot Chemical Compound Co. and is described in U.S Patent Application Publication No.2023 / 0111310. Flusulfinam, the ISO name for 2-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3- (propylsulfinyl)-4-(trifluoromethyl)benzamide (the (R)-enantiomer), is an amide herbicide from Qingdao KingAgroot Chemical Compound Co., and is described in US Patent Application Publication No. 2023 / 0041563. Flusulfinam is effective in controlling weeds commonly found around rice crops (such as indica rice, japonica rice), gramineous weed (such as rice barnyardgrass, Qianjinjin, barnyard grass, horse tang, Setaria), broad-leaved weeds (such as gazania, velvetleaf, amaranth, chickweed), and sedge weeds (such as sedge, fireflies). Icafolin, the ISO name for (2RS,4RS)-4-({[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4,5- dihydroisoxazol-5-yl]carbonyl}amino)tetrahydrofuran-2-carboxylic acid (including combinations of the (2S,4S), (2R,4R) isomers), is an isoxazole herbicide from Bayer AG (CAS Reg. No. 2749998-21-6) and is a broad-spectrum herbicide for the control of mono dicotyledonous annual weeds, such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Polygonum convolvulus, Setaria viridis, Veronica persica. Icafolin esters and salts activities are disclosed in International PCT Application Publication Nos. WO2018228985 and WO2018228986. Icafolin can be applied pre-emergence or post-emergence to control various weeds, such as butilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Echinochloca crus, during preemergence treatment. gallium, Hordeum murinum, Lolium rigidum, Pharitis purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica and Viola tricolor. Iptriazopyrid, the ISO name for 3-[[(1-methylethyl)sulfonyl]methyl]-N-(5-methyl- 1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyridine-8-carboxamide, is an amide herbicide from Nissan Chemical Corp. (CAS Reg. No. 1994348-72-9) and is disclosed in Attorney Docket: 212168-WO-SEC-1 International PCT Application Publication Nos. WO2014192936 and WO2020189576 (polymorphic crystal forms of Iptriazopyrid may be used as an herbicide for paddy fields in any ofthe treatment methods of soil treatment and foliage treatment under flooding. In someembodiments, can be preferably used in a treatment method by foliar treatment when in mixtures of the disclosed compounds. For example, iptriazopyrid may also be used with crops such as corn, rice, wheat, barley, lime tree, embaku, sorghum, cotton, soybean, peanut, buckwheat, tensai, rapeseed, sunflower, sugar cane, tobacco and the like. Metproxybicyclone, the ISO name for the racemic mixture (1RS,5SR)-3-[2-methoxy-4- (prop-1-yn-1-yl)phenyl]-4-oxobicyclo[3.2.1]oct-2-en-2-yl methyl carbonate, available from Syngenta Crop Protection (CAS Reg. No. 1848207-89-5) and is described in International PCT Application Publication No. WO2015197468. Flufenauxirim, the ISO name for the compound 6-amino-2-[2-fluoro-3-methoxy-4- (trifluoromethyl)phenyl]-5-methoxy-4-pyrimidinecarboxylic acid, is an auxinic herbicide available from Qingdao KingAgroot Chemical Compound Co. (CAS Reg. No.3054208-46-4), and is described in International PCT Application Publication No. WO 2024 / 169666. The metotyl ester, flufenauxirim-metotyl, may also be used as an auxinic herbicide. Flufenauxirim may be used as a herbicide to control grass and broadleaf weeds. Flufenauxirim may be selective for lawn grasses such as Zoysia, Bermuda, tall fescue, and bluegrass, and it may be used with crops such as sugarcane, soybean, cotton, sunflower, potatoes, fruit trees, and vegetables. The more recent herbicides described above can be applied to vegetation or an areaadjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetationin an amount sufficient to induce a herbicidal effect. In some aspects, the more recent herbicide isapplied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 0.1 g ai / ha or more, such as 0.125 g ai / ha or more, 0.15 g ai / ha or more, 0.175 g ai / ha or more, 0.20 g ai / ha or more, 0.25 g ai / ha or more, 0.3 g ai / ha or more, 0.4 g ai / ha or more, 0.5 g ai / ha or more, 0.6 g ai / ha or more, 0.7 g ai / ha or more, 0.8g ai / ha or more, 0.9 g ai / ha or more, 1 g ai / ha or more, 1.1 g ai / ha or more, 1.25 g ai / ha or more,1.5 g ai / ha or more, 1.75 g ai / ha or more, 2 g ai / ha or more, 2.25 g ai / ha or more, 2.5 g ai / ha or more, 2.75 g ai / ha or more, 3 g ai / ha or more, 3.25 g ai / ha or more, 3.5 g ai / ha or more, 3.75 g ai / ha or more, 4 g ai / ha or more, 4.25 g ai / ha or more, 4.5 g ai / ha or more, 4.75 g ai / ha or more, 5 g ai / ha or more, 5.25 g ai / ha or more, 5.5 g ai / ha or more, 5.75 g ai / ha or more, 6 g ai / ha or more, 6.25 gai / ha or more, 6.5 g ai / ha or more, 6.75 g ai / ha or more, 7 g ai / ha or more, 7.25 g ai / ha or more, 7.5g ai / ha or more, 8 g ai / ha or more, 8.5 g ai / ha or more, 9 g ai / ha or more, 9.5 g ai / ha, or more, 10 gai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 gai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g Attorney Docket: 212168-WO-SEC-1 ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 175 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 210 g ai / ha or more, 220 g ai / ha or more, 225 g ai / ha or more, 230 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 270 g ai / ha or more, 275 g ai / ha or more, 280 g ai / ha or more, 290 g ai / ha or more, 300 g ai / ha or more, 310 g ai / ha or more, 320 g ai / ha or more, 325 g ai / ha or more, 330 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha or more, 370 g ai / ha or more, 375 g ai / ha or more, 380 g ai / ha or more, 390 g ai / ha or more, 400 g ai / ha or more, 410 g ai / ha or more, 420 g ai / ha or more, 425 g ai / ha or more, 430 g ai / ha or more, 440 g ai / ha or more, 450 g ai / ha or more, 460 g ai / ha or more, 470 g ai / ha or more, 475 g ai / ha or more, 480 g ai / ha or more, 490 g ai / ha or more, 500 g ai / ha or more, 525 g ai / ha or more, 550 g ai / ha or more, 575 g ai / ha or more, 600 g ai / ha or more, 625 g ai / ha or more, 650 g ai / ha or more, 675 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more, 1000 g ai / ha or more, 1050 g ai / ha or more, 1100 g ai / ha or more, 1150 g ai / ha or more, 1200 g ai / ha or more, 1250 g ai / ha or more, 1300 g ai / ha or more, 1350 g ai / ha or more, 1400 g ai / ha or more, 1450 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2100 g ai / ha or more, 2200 g ai / ha or more, 2300 g ai / ha or more, 2400 g ai / ha or more, 2500 g ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3250 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3750 g ai / ha or more, 4000 g ai / ha or more, 4250 g ai / ha or more, 4500 g ai / ha or more, 4750 g ai / ha or more, 5000 g ai / ha or more, 5250 g ai / ha or more, 5500 g ai / ha or more, 5750 g ai / ha or more, 6000 g ai / ha or more, 6500 g ai / ha or more, 7000 g ai / ha or more, 7500 g ai / ha or more, 8000 g ai / ha or more, 8500 g ai / ha or more, 9000 g ai / ha or more, 9500 g ai / ha or more, or 10 kg ai / ha or more; in an amount of 11 kg ai / ha or less, such as 10 kg ai / ha or less, 9500 g ai / ha or less, 9000 g ai / ha or less, 8500 g ai / ha or less, 8000 g ai / ha or less, 7500 g ai / ha or less, 7000 g ai / ha or less, 6500 g ai / ha or less, 6000 g ai / ha or less, 5750 g ai / ha or less, 5500 g ai / ha or less, 5250 g ai / ha or less, 5000 g ai / ha or less, 4750 g ai / ha or less, 4500 g ai / ha or less, 4250 g ai / ha or less, 4000 g ai / ha or less, 3750 g ai / ha or less, 3500 g ai / ha or less, 3400 g ai / ha or less, 3300 g ai / ha or less, 3250 g ai / ha or less, 3200 g ai / ha or less, 3100 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 g ai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 g ai / ha or less, 2400 g ai / ha or less, 2300 g ai / ha or less, 2200 g ai / ha or less, 2100 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1400 g ai / ha or less, 1350 g ai / ha or less, 1300 g ai / ha or less, 1250 g ai / ha or less, 1200 g ai / ha or Attorney Docket: 212168-WO-SEC-1 less, 1150 g ai / ha or less, 1100 g ai / ha or less, 1050 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 675 g ai / ha or less, 650 g ai / ha or less, 625 g ai / ha or less, 600 g ai / ha or less, 575 g ai / ha or less, 550 g ai / ha or less, 525 g ai / ha or less, 500 g ai / ha or less, 490 g ai / ha or less, 480 g ai / ha or less, 475 g ai / ha or less, 470 g ai / ha or less, 460 g ai / ha or less, 450 g ai / ha or less, 440 g ai / ha or less, 430 g ai / ha or less, 425 g ai / ha or less, 420 g ai / ha or less, 410 g ai / ha or less, 400 g ai / ha or less, 390 g ai / ha or less, 380 g ai / ha or less, 375 g ai / ha or less, 370 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 330 g ai / ha or less, 325 g ai / ha or less, 320 g ai / ha or less, 310 g ai / ha or less, 300 g ai / ha or less, 290 g ai / ha or less, 280 g ai / ha or less, 275 g ai / ha or less, 270 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 230 g ai / ha or less, 225 g ai / ha or less, 220 g ai / ha or less, 210 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 175 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, 55 g ai / ha or less, 50 gai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha orless, 20 g ai / ha or less, 15 g ai / ha or less, 10 g ai / ha or less, 9.5 g ai / ha or less, 9 g ai / ha or less, 8.5 g ai / ha or less, 8 g ai / ha or less, 7.5 g ai / ha or less, 7.25 g ai / ha or less, 7 g ai / ha or less, 6.75 g ai / ha or less, 6.5 g ai / ha or less, 6.25 g ai / ha or less, 6 g ai / ha or less, 5.75 g ai / ha or less, 5.5 g ai / ha orless, 5.25 g ai / ha or less, 5 g ai / ha or less, 4.75 g ai / ha or less, 4.5 g ai / ha or less, 4.25 g ai / ha orless, 4 g ai / ha or less, 3.75 g ai / ha or less, 3.5 g ai / ha or less, 3.25 g ai / ha or less, 3 g ai / ha or less, 2.75 g ai / ha or less, 2.5 g ai / ha or less, 2.25 g ai / ha or less, 2 g ai / ha or less, 1.75 g ai / ha or less, 1.5 g ai / ha or less, 1.25 g ai / ha or less, 1.1 g ai / ha or less, 1 g ai / ha or less, 0.9 g ai / ha or less, 0.8 g ai / ha or less, 0.7 g ai / ha or less, 0.6 g ai / ha or less, 0.5 g ai / ha or less, 0.4 g ai / ha or less, 0.3 g ai / ha or less, 0.2 g ai / ha or less, 0.175 g ai / ha or less, 0.15 g ai / ha or less, 0.125 g ai / ha or less, 0.11 g ai / ha or less, or 0.1 g ai / ha or less; or in an amount ranging from any of the minimum valuesdescribed above to any of the maximum values described above, such as 0.10 g – 11 kg ai / ha, 950–6500 g ai / ha, 7–250 g ai / ha, 460–3750 g ai / ha, 600–2500 g ai / ha, 50–5000 g ai / ha, 110–450 g ai / ha,15-160 g ai / ha, 1900–4000 g ai / ha, 1–4 g ai / ha, 750–2200 g ai / ha, 380–5250 g ai / ha, 0.2–17.25 gai / ha, 500–1400 g ai / ha, 3.25–950 g ai / ha, 440–2900 g ai / ha, or 0.5 –250 g ai / ha.5. Physical StatesIn some aspects, the compositions comprising the substituted 5-membered ring moleculeherbicide may be present in suspended, emulsified, dissolved, or solid form. Exemplary compositions include, but are not limited to, aqueous solutions, aqueous suspensions, aqueous dispersions, aqueous emulsions, aqueous microemulsions, aqueous suspo-emulsions, oil solutions, Attorney Docket: 212168-WO-SEC-1 oil suspensions, oil dispersions, oil emulsions, oil microemulsions, oil suspo-emulsions, self- emulsifying formulations, gels, pastes, powders, dusts, granules, and materials for spreading. In some aspects, the substituted 5-membered ring molecule herbicide is in an aqueoussolution that can be diluted before use. In various aspects, the substituted 5-membered ring molecule herbicide 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 higher. In some aspects, the concentrate does not exhibit separation, precipitation, or crystallization of any components at low temperatures. For example, the concentrate remains a clear solution at temperatures below 0 °C (e.g., below -5 °C, below -10 °C, below -15 °C). In some aspects, the concentrate exhibits a viscosity of less than 50 centipoise (50 megapascals), even at temperatures as low as 5 °C. In some aspects, the concentrate does not exhibit separation, precipitation, or crystallization of any components during storage for a period of 2 weeks or greater (e.g., 4 weeks, 6 weeks, 8 weeks, 3 months, 6 months, 9 months, or 12 months or greater). In some aspects, emulsions, gels, pastes, or oil dispersions can be prepared byhomogenizing the substituted 5-membered ring molecule herbicide in water with a wetting agent,tackifier, dispersant, or emulsifier. In some aspects, concentrates suitable for dilution with watercan be prepared, comprising the substituted 5-membered ring molecule herbicide, a wetting agent,a tackifier, and a dispersant or emulsifier. In some aspects, powders, materials for spreading, or dusts can be prepared by mixingor concomitant grinding the substituted 5-membered ring molecule herbicide and optionally otheradditives with a solid carrier. In some aspects, granules (e.g., coated granules, impregnated granules and homogeneousgranules) can be prepared by binding the substituted 5-membered ring molecule herbicide to solidcarriers. In some aspects, the compositions comprise, by total weight of the composition, fromabout 0.01% to about 99% of the substituted 5-membered ring molecule herbicide, including about0.025%, 0.05%, 0.075%, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 7.5%, 8%, 9%, 10%, 12.5%, 15%, 17.5%, 20%, 22.5%, 25%, 27.5%, 30%, 32.5%, 35%, 37.5%, 40%, 42.5%, 45%, 47.5%, 50%, 52.5%, 55%, 57.5%, 60%, 62.5%, 65%, 67.5%, 70%, 72.5%, 75%, 77.5%, 80%, 82.5%, 85%, 87.5%, 90%, 92.5%, 95%, 97.5%, or 98%of the substituted 5-membered ring molecule herbicide by total weight of the composition, or Attorney Docket: 212168-WO-SEC-1 within any range defined between any two of the forgoing values, such as between about 1% to about 97%, between about 10% to about 90%, between about 20% to about 45%, and about 25% to about 50% based on the total weight of the composition. Concentrates can be diluted with an inert carrier, such as water, prior to application. The diluted compositions applied to undesirable vegetation or the locus of undesirable vegetation can contain from 0.0006 to 8.0 weight percent (wt %) of the total amount of the substituted 5-membered ring molecule herbicide (e.g., from 0.001to 5.0 wt %), based on the total weight of the diluted composition.5. Methods of UseThe substituted 5-membered ring molecules disclosed herein can be formulated intocompositions and 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. In some aspects, a method of controlling undesirable vegetation which 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 compositions is disclosed herein. The compositions containing a substituted 5-membered ring molecule disclosed hereincan be applied pre-emergence (before the emergence of undesirable vegetation) or post-emergence (e.g., during and / or after emergence of the undesirable vegetation). In some aspects, the composition is applied postemergence to the undesirable vegetation. When the compositions are used in crops, the compositions can be applied after seeding and before or after the emergence of the crop plants. In some aspects, the compositions disclosed herein show good crop tolerance even when the crop has already emerged and can be applied duringor after the emergence of the crop plants. In some aspects, when the compositions are used in crops, the compositions can be applied before seeding of the crop plants. In some aspects, the compositions 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 compositions 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 compositions disclosed herein are less well Attorney Docket: 212168-WO-SEC-1 tolerated by certain crop plants, the compositions 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 plantswhile 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 compositions disclosed herein can be applied as dry compositions (e.g., granules, powders, or dusts). In some aspects, wherein the undesirable vegetation is treated post-emergence, the compositions 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. The compositions and methods disclosed herein can be used to control undesirable vegetation in a variety of applications. The compositions 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, canola, pulses, sunflower, sugar beet, sorghum, rice, millet,sugarcane, and range land (e.g., pasture grasses). In some aspects, the compositions and methodsdisclosed herein can be used for controlling undesirable vegetation in maize, soy, canola, cotton,pulses, sunflower, sugar beet, wheat, barley, rice, sorghum, millet, oats, or combinations thereof.In some aspects, the compositions 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 compositions 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 compositions 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 compositions and methods disclosed herein can be used on lawns (e.g., residential, industrial, and institutional), golf courses, parks, cemeteries, athletic fields, and sod farms. Attorney Docket: 212168-WO-SEC-1 The compositions and methods disclosed herein can also be used in crop plants that areresistant to, for instance, herbicides, insecticides, fungicides, pathogens, insects, or combinationsthereof. 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 resistantto 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 plantsthat, owing to introduction of the gene for Bacillus thuringiensis (or Bt) toxin by geneticmodification, 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, or combinations 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 (includingbut not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture). The compounds and compositions described herein may be used to control plant species described, but not limited to, weeds species found in Randall, R.P. (2017). A Global Compendiumof Weeds. 3rd Edition. Perth, Western Australia. In some aspects, the compositions disclosed Attorney Docket: 212168-WO-SEC-1 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, Aperaspecies, Amaranthus species, Avena species, Brachiaria species, Bromus species, Chenopodiumspecies, 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 speciesPolygonum species, Prosopis species, Rumex species, Setaria species, Sida species, Sisymbriumspecies, Solanum species, Sorghum species, Trifolium species, Xanthium species, Veronica species,and Viola species. In some aspects, the undesired vegetation includes blackgrass (Alopecurusmyosuroides Huds.), wild oat (Avena fatua), barnyard grass (Echinochloa crus-galli) commonchickweed (Stellaria media), velvetleaf (Abutilon theophrasti), hemp sesbania (Sesbania exaltataCory), Anoda cristata, Bidens pilosa, Brassica kaber, shepherd’s purse (Capsella bursa-pastoris),cornflower (Centaurea cyanus or Cyanus segetum), hempnettle (Galeopsis tetrahit), cleavers(Galium aparine), common sunflower (Helianthus annuus), Desmodium tortuosum, Italianryegrass (Lolium multiflorum), kochia (Kochia scoparia), Medicago arabica, Mercurialis annua,Myosotis arvensis, common poppy (Papaver rhoeas), Raphanus raphanistrum, broad-leaf dock(Rumex obtusifolius), Russian thistle (Salsola kali), wild mustard (Sinapis arvensis), Sonchusarvensis, Thlaspi arvense, Tagetes minuta, Richardia brasiliensis, Plantago major, Plantagolanceolata, bird’seye speedwell (Veronica persica), pigweed (Amaranthus retroflexus), winterrape (Brassica napus), lambsquarters (Chenopodium album), Canadian thistle (Cirsium arvense),nutsedge (Cyperus esculentus), poinsettia (Euphorbia heterophylla), prickly lettuce (Lactucaserriola), 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 (Sorghumvulgare), wild pansy (Viola tricolor), or combinations thereof. 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 tocontrol herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, butare not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, Attorney Docket: 212168-WO-SEC-1 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, triazolocarboxamides), 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).6. ExamplesBy 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. The details of the compositions and the crops tested are specified in the following Examples. Method 1: Pre-emergence Application Methods for Herbicide Evaluations Seeds of the desired test plant species were planted into 12.7 cm diameter round plastic pots containing a silt loam mineral soil. Compositions of each exemplified molecule were dissolvedin 0.67 mL 97:3 v / v mixture of acetone and DMSO, then further diluted with 2.05 mL of solvent containing 78% D.I. H2O, 20% isopropanol, 2% AgriDex crop oil concentrate and 0.02% Tergitol Attorney Docket: 212168-WO-SEC-1 15S-7 surfactant. Samples were mixed vigorously (vortexed) and sonicated if needed to bring the compound into solution. Solution was mixed with 15 mL of D.I. H2O and poured evenly over the soil containing potted seeds. The vial was rinsed with an additional 15 mL of D.I. H2O which wasagain poured over the soil. Treated pots are moved to a greenhouse with an approximate 16-hour (h) photoperiodand maintained at 23 °C during the day and 22 °C during the night. Pots were kept moist through over-the-top irrigation. After 14 days, the condition of the test plants was compared with that ofthe control plants by visual assessment and the herbicidal effects of the test compounds wereevaluated based on a scoring scale of 0 to 100 percent where 0 corresponds to no injury and 100corresponds to complete plant death. Visual assessments of herbicidal effect were made based ongrowth reduction, discoloration, leaf deformity and necrosis. Results are presented in Table 2 below.Table 2. Herbicidal Effect (%) 14 Days After Pre-emergent ApplicationCompd Rate No.(gai / ha) ALOMY AVEFA AVESA ECHCG SETFA HELAN IPOHE Attorney Docket: 212168-WO-SEC-1 Compd Rate No.(gai / ha)ALOMY AVEFA AVESA ECHCG SETFA HELAN IPOHE Attorney Docket: 212168-WO-SEC-1 Compd Rate No.(gai / ha)ALOMY AVEFA AVESA ECHCG SETFA HELAN IPOHE Attorney Docket: 212168-WO-SEC-1 Compd Rate No.(gai / ha) ALOMY AVEFA AVESA ECHCG SETFA HELAN IPOHE ECHCG = Echinochloa crus-galli (barnyardgrass)SETFA = Setaria faberi (giant foxtail) HELAN = Helianthus annuus (common sunflower)IPOHE = Ipomoea hederacea (ivyleaf morningglory)g ai / ha = grams active ingredient per hectare NT = not tested Method 2: Postemergence Application Methods for Herbicide Evaluations Seeds of the desired test plant species were planted in plastic pot with 64 squarecentimeter (cm2) surface area filled with soil-less media planting mix containing PRO-MIX®BX (Premier Tech Horticulture, Quakertown, PA, USA) and PROFILE® GREENS GRADE™ (ProfileProducts LLC, Buffalo Grove, IL, USA) at pH of 5.2 to 6.2 and a minimum of 50% organic matter content. Echinochloa crus-galli (ECHCG, barnyard grass) and Setaria faberi (SETFA, giantfoxtail) were planted together 11 days prior to application. In a separate pot Alopecurus myosuroides (ALOMY, blackgrass) and Avena fatua (AVEFA, wild oat) or Avena sativa (AVESA,common oat) were planted together and propagated 11 and 8 days prior to application, respectively.Ipomea hederacea (IPOHE, ivyleaf morningglory) and Helianthus annuus (HELAN, sunflower)were planted together in a separate pot, 8 days prior to application. Plants were grown in agreenhouse set to 23 °C day and 22 °C night temperature regimen with a 16 hour photoperiod for the propagation period and returned to the same conditions after treatment. Plants were sub-irrigated as needed with water containing Jack’s Professional 15-5-154 Ca 2Mg fertilizer. Compositions of each exemplified molecule were dissolved in 2.75 mL of formulation solvent containing by volume (59% deionized water, 24% acetone, 15% isopropanol, 0.75%DMSO, 1.5% crop oil concentrate, 0.02% Tergitol 15S-7) to deliver a spray rate of 4000 grams ofactive ingredient per hectare (g ai / h). Samples were vortexed and sonicated if needed to dissolve the compound into solution. Formulated compounds were applied to all six species in 3 pots using a DeVilbiss® compressed air sprayer at 2–4 pounds per square inch (psi), allowed to dry then returned to the Attorney Docket: 212168-WO-SEC-1 greenhouse. After 10 days, the condition of the test plants was compared with that of the control plants by visual assessment and the herbicidal effects of the test compounds were evaluated based on a scoring scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete plant death. Visual assessments of herbicidal effect were made based on growth reduction, discoloration, leaf deformity and necrosis. Results are presented in Table 3 below. Table 3. Herbicidal Effect (%) 14 Days After Post-emergent Application Compd Rate No.(gai / ha)ALOMY AVEFA AVESA ECHCG SETFA HELAN IPOHE Attorney Docket: 212168-WO-SEC-1 Compd Rate No.(gai / ha)ALOMY AVEFA AVESA ECHCG SETFA HELAN IPOHE Attorney Docket: 212168-WO-SEC-1 Compd Rate No.(gai / ha)ALOMY AVEFA AVESA ECHCG SETFA HELAN IPOHE AVESA = Avena sativa (common oat) ECHCG = Echinochloa crus-galli (barnyardgrass) Attorney Docket: 212168-WO-SEC-1 SETFA = Setaria faberi (giant foxtail) HELAN = Helianthus annuus (common sunflower)IPOHE = Ipomoea hederacea (ivyleaf morningglory)g ai / ha = grams active ingredient per hectare NT = not tested Method 3: Postemergence Application Methods for Herbicide Evaluations Seeds of the desired test plant species were planted in plastic pot with 64 squarecentimeter (cm2) surface area filled with soil-less media planting mix containing PRO-MIX® BX(Premier Tech Horticulture, Quakertown, PA, USA) and PROFILE® GREENS GRADE™ (ProfileProducts LLC, Buffalo Grove, IL, USA) at pH of 5.2 to 6.2 and a minimum of 50% organic matter content. In some aspects or embodiments, to help ensure good germination and healthy plants, afungicide treatment and / or other chemical or physical treatment was applied. Some plants were propagated in growth chambers for 4–13 days (d) with a 16-hour (h) photoperiod which was maintained at either 28 °C during the day and 24 °C during the night, or 25 °C during the day and 22 °C during the night, dependent on species. Some plants were grown and maintained for 15 days (d) in a greenhouse with an approximate 14-hour (h) photoperiod which was maintained at about 27 °C during the day and 24 °C during the night. Plants were sub-irrigated as needed with water containing Jack’s Professional 15-5-15 4 Ca 2Mg fertilizer. Supplemental lighting was providedas necessary. The plants were employed for testing when they reached the second or third true leaf stage. Compositions of each exemplified molecule was weighed to a known amount, determined by the highest rate to be tested, by placing in a 25 mL glass vial and was dissolved in 4 mL of a 97:3 v / v mixture of acetone and DMSO to obtain concentrated stock solutions. If the test compound did not dissolve readily, the mixture was warmed and / or sonicated. The concentrated stock solutions obtained were diluted with 20 mL of an aqueous mixture containing acetone, water, isopropyl alcohol, DMSO, AgriDex crop oil concentrate, and Tergitol 15S-7 surfactant in a 48.5:39:10:1.5:1.0:0.02 v / v ratio to obtain spray solutions at the application rate. Compoundrequirements are based upon a 12 mL application volume at a rate of 187 liters per hectare (L / ha). The spray solutions were applied to the plant material with an overhead DeVries tracksprayer equipped with 8002E nozzles calibrated to deliver 187 L / ha over an application area of 0.503 square meters (m2) at a spray height of 18 inches (43 centimeters (cm)) above the average plant canopy. Control or non-treated plants were sprayed in the same manner with the solvent blank or not treated. All herbicide application rates are given as grams acid equivalent per hectare(g ae / h) or grams active ingredient per hectare (g ai / h).The treated plants and control plants were placed in a greenhouse as described above and watered by subirrigation to prevent removal of the test compound. After 13-15 days, the Attorney Docket: 212168-WO-SEC-1 condition of the test plants was compared with that of the control plants by visual assessment, and the herbicidal effects of the test compounds were evaluated based on a scoring scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete plant death. Visual assessments of herbicidal effect were made based on growth reduction, discoloration, leaf deformity and necrosis. Results are presented in Tables 4A – 4C below. Table 4A. Herbicidal Effect (%) 14 Days After Application – Monocot Weeds Compd No.Rate (gai / ha) AVEFA AVESA ALOMY DIGSA SETFA ECHCG1 3125 85 NT 35 5 60 0 Attorney Docket: 212168-WO-SEC-1 Compd No.Rate (gai / ha) AVEFA AVESA ALOMY DIGSA SETFA ECHCG125 85 NT 60 80 90 30 Attorney Docket: 212168-WO-SEC-1 Compd No.Rate (gai / ha) AVEFA AVESA ALOMY DIGSA SETFA ECHCG500 NT 85 75 65 100 30 Attorney Docket: 212168-WO-SEC-1 Compd No.Rate (gai / ha) AVEFA AVESA ALOMY DIGSA SETFA ECHCG500 NT 40 35 0 0 5 Attorney Docket: 212168-WO-SEC-1 Compd No.Rate (gai / ha) AVEFA AVESA ALOMY DIGSA SETFA ECHCG58 31.25 40 NT 40 5 60 5 = opecu us yosu o es ac g ass DIGSA = Digitaria sanguinalis (large crabgrass) SETFA = Setaria faberi (giant foxtail) ECHCG = Echinochloa crus-galli (barnyardgrass) g ai / ha = grams active ingredient per hectare NT = not tested Table 4B. Herbicidal Effect (%) 14 Days After Application – Dicot Weeds Compd No. Rate (gai / ha) IPOHE CHEAL AMARE 1 3125 0 0 0 Attorney Docket: 212168-WO-SEC-1 Compd No. Rate (gai / ha) IPOHE CHEAL AMARE 6 31.25 0 0 0 Attorney Docket: 212168-WO-SEC-1 Compd No. Rate (gai / ha) IPOHE CHEAL AMARE 500 0 0 0 Attorney Docket: 212168-WO-SEC-1 Compd No. Rate (gai / ha) IPOHE CHEAL AMARE 38 31.25 0 0 0 Attorney Docket: 212168-WO-SEC-1 Compd No. Rate (gai / ha) IPOHE CHEAL AMARE 125 0 5 5 AMARE = Amaranthus retroflexus (pigweed) g ai / ha = grams active ingredient per hectare NT = not tested Table 4C. Herbicidal Effect (%) 14 Days After Application – Crops Compd NRate (gai / ha) BRSNW GLXMA TRZAS ORYSK ZEAMX Attorney Docket: 212168-WO-SEC-1 Compd No.Rate (gai / ha) BRSNW GLXMA TRZAS ORYSK ZEAMX500 0 0 100 75 0 Attorney Docket: 212168-WO-SEC-1 Compd No.Rate (gai / ha) BRSNW GLXMA TRZAS ORYSK ZEAMX16 31.25 0 0 80 20 0 Attorney Docket: 212168-WO-SEC-1 Compd No.Rate (gai / ha) BRSNW GLXMA TRZAS ORYSK ZEAMX33 31.25 0 0 75 10 0 Attorney Docket: 212168-WO-SEC-1 Compd No.Rate (gai / ha) BRSNW GLXMA TRZAS ORYSK ZEAMX47 31.25 0 0 50 20 0 Attorney Docket: 212168-WO-SEC-1 Compd No. Rate (gai / ha) BRSNW GLXMA TRZAS ORYSK ZEAMX125 5 0 80 0 5 ORYSK = Oryza sativa (common rice)ZEAMX = Zea mays (maize)g ai / ha = grams active ingredient per hectare NT = not tested As can be seen from the data contained in Tables 2-3, the substituted 5-membered ringmolecules typically have herbicidal activity and address the aforementioned need for newherbicides and methods to control the growth of undesirable vegetation in various locations. Ascan be seen from the data in Tables 4A and 4B, the substituted 5-membered ring molecules aretypically effective in controlling monocot (grass) weeds at low application rates, though they are typically ineffective against dicot (broadleaf) weeds at the same application rates. The data inTable 4C demonstrates that the substituted 5-member ring molecules may be safe to use with thecrops winter canola, soybean, and maize, typically causing minimal or no damage, but these 5- membered ring molecules may cause significant damage to wheat and rice crops without theadditional application of safeners to these crops.The substituted 5-membered ring molecules, compositions and methods of the appendedclaims are not limited in scope by the specific compositions and methods described herein, whichare intended as illustrations of a few aspects of the claims and any compositions and methods that are functionally equivalent are intended to fall within the scope of the claims. Variousmodifications of the substituted 5-membered ring molecules, compositions, and methods inaddition to those shown and described herein are intended to fall within the scope of the appendedclaims. Further, while only certain representative substituted 5-membered ring molecules,compositions and method steps disclosed herein are specifically described, other combinations of the compositions 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 terms Attorney Docket: 212168-WO-SEC-1 “including” and “containing” and variations thereof, and are open, non-limiting terms. Although the terms “comprising,” “including,” and “containing” have been used herein to describe various aspects, the terms “consisting essentially of” and “consisting of” can be used in place of “comprising,” “including,” or “containing” to provide for more specific aspects 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
Attorney Docket: 212168-WO-SEC-1 WHAT IS CLAIMED IS:
1. A substituted 5-membered ring molecule of Formula (I):wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R4is selected from the group consisting of methyl and cyclopropyl; R5is selected from the group consisting of H, methyl, and methoxy; R6is selected from the group consisting of H, hydroxy, (C1-C8)-alkyl, (C3-C8)-alkenyl, (C3- C8)-alkynyl, (C3-C8)-cycloalkyl, (C4-C10)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C5-C12)-aryl, (C6-C18)-alkylaryl, (C1-C12)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C8)-alkoxy, (C5-C16)-arylalkoxy, (C1-C6)-alkylcyano, (C1- C8)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C6)-alkylthio-(C1-C6)-alkyl, (C0-C6)-alkyl- sulfonyl-R74, NR72R73, SiR75R76R77, (C1-C6)-alkyl-SiR75R76R77, R78R79C=N, (C1-C10)-alkyl- C(=O)QR70, aryl-(C1-C6)-alkyl-C(=O)QR70, heteroaryl-(C1-C6)-alkyl-C(=O)QR70, (C3-C10)- cycloalkyl-(C0-C6)-alkyl-C(=O)QR70, R70QC(=O)-(C1-C6)-alkyl-C(=O)QR71, R70QC(=O)Q-(C1-C6)- alkyl-C(=O)QR71, hydroxy-(C1-C6)-alkyl-C(=O)QR70, (C1-C6)-alkylthio-(C1-C6)-alkyl-C(=O)QR70, and salts thereof; Q is selected from the group consisting of O, S, and NR72, R70, R71, R72, R73, and R74are independently selected from the group consisting of H, (C1- C16)-alkyl, (C4-C16)-aryl, (C1-C16)-heteroaryl, (C5-C16)-alkylaryl,(C1-C16)-haloalkyl, (C1-C16)- arylalkoxy, NR78R79, and R72and R73together may form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; andAttorney Docket: 212168-WO-SEC-1 R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (I).
2. The substituted 5-membered ring molecule of claim 1, comprising a molecule of Formula (II):wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring;Attorney Docket: 212168-WO-SEC-1 or an agriculturally-acceptable salt of the molecule of Formula (II).
3. The substituted 5-membered ring molecule of claim 1, comprising a molecule of Formula (III):wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (III).Attorney Docket: 212168-WO-SEC-1 4. The substituted 5-membered ring molecules of claim 1, comprising molecules of Formula (IV):wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (IV).
5. The substituted 5-membered ring molecule of any one of claims 1-4, wherein X1and X2are O and Y is O.Attorney Docket: 212168-WO-SEC-1 6. The substituted 5-membered ring molecule of any one of claims 1-5, wherein R6is selected from the group consisting of H, (C1-C16)-alkyl, (C1-C10)-alkyl-aryl, and aryl.
7. The substituted 5-membered ring molecule of any one of claims 1-6, wherein R1is F and R2is Cl.
8. A herbicidal composition comprising a. a 5-member ring-based of Formula (I):wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R4is selected from the group consisting of methyl, methoxy, and cyclopropyl; R5is selected from the group consisting of H, methyl, and methoxy; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; andAttorney Docket: 212168-WO-SEC-1 R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (I); and b. a carrier.
9. The herbicidal composition of claim 8, comprising a molecule of Formula (II):wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring.Attorney Docket: 212168-WO-SEC-1 10. The herbicidal composition of claim 8, comprising a molecule of Formula (III)wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (II).Attorney Docket: 212168-WO-SEC-1 11. The herbicidal composition of claim 8, comprising molecules of Formula (IV):wherein: X1and X2are independently selected from the group consisting of O and S; Y is selected from the group consisting of O, NH, and S; R1, R2, and R3are independently selected from the group consisting of H, Cl, and F, with the proviso that when R1is F, R2is not F, and when R2is F, R1is not F; R6is selected from the group consisting of H, (C1-C16)-alkyl, (C3-C10)-cycloalkyl, (C3-C16)- alkenyl, (C3-C16)-alkynyl, (C4-C16)-alkylcycloalkyl, (C5-C16)-polycycloalkyl, (C6-C16)- alkylpolycycloalkyl, (C3-C10)-heterocycloalkyl, (C4-C16)-aryl, (C5-C18)-alkylaryl, (C1-C16)- heteroaryl, (C4-C16)-alkylheteroaryl, (C1-C16)-alkoxy, (C4-C16)-arylalkoxy, (C1-C10)-alkylcyano, (C1- C16)-haloalkyl, (C1-C10)-alkoxy-(C1-C10)-alkyl, (C1-C10)-alkylthio-(C1-C10)-alkyl, (C1-C10)-alkyl- sulfonyl-(C1-C10)-alkyl, R72R73N, SiR75R76R77, (C1-C10)-alkyl-SiR75R76R77, R78R79C=N, and salts thereof; R72and R73are independently selected from the group consisting of H, (C1-C16)-alkyl, aryl, heteroaryl, (C1-C16)-alkyl-aryl, and (C1-C16)-haloalkyl, or R72and R73together form a substituted or unsubstituted ring; R75, R76, and R77are independently selected from the group consisting of (C1-C16)-alkyl and aryl; and R78and R79are independently selected from the group consisting of (C1-C16)-alkyl, (C1-C16)- alkyl-aryl, (C1-C16)-haloalkyl, aryl, and heteroaryl, or R78and R79together form a substituted or unsubstituted ring; or an agriculturally-acceptable salt of the molecule of Formula (IV).
12. The herbicidal composition of any one of claims 8-11, wherein X1and X2are O and Y is O.
13. The herbicidal composition of any one of claims 8-12, wherein R6is selected from the group consisting of H, (C1-C16)-alkyl, (C1-C10)-alkyl-aryl, and aryl.Attorney Docket: 212168-WO-SEC-1 14. The herbicidal composition of any one of claims 8-13, wherein R1is F and R2is Cl.
15. The herbicidal composition of any one of claims 8-14, comprising an adjuvant.
16. The herbicidal composition of any one of claims 8-15, comprising a safener.
17. The herbicidal composition of any one of claims 8-16, comprising an additional herbicide.
18. The herbicidal composition of any one of claims 8-17, wherein the composition is selected from the group consisting of aqueous solutions, aqueous suspensions, aqueous dispersions, aqueous emulsions, aqueous microemulsions, aqueous suspo-emulsions, oil solutions, oil suspensions, oil dispersions, oil emulsions, oil microemulsions, oil suspo-emulsions, self-emulsifying formulations, gels, pastes, powders, dusts, granules, and materials for spreading.
19. A method of controlling undesirable vegetation, comprising the steps of applying the substitute 5-membered ring molecule of any one of claims 1-7 or the herbicidal composition of any one of claims 8-19 to deliver the substituted 5-membered ring molecule or the herbicidal composition, directly to the targeted undesirable vegetation or to the locus thereof or to the area where control of undesirable vegetation is desired.
Citation Information
Patent Citations
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