(2,4-Dichlorophenoxy)acetic acid analogues

Abstract

The present disclosure includes pesticidal compounds, compositions, and related agricultural methods.

Description

[Technical Field]

[0001] Aspects of the present disclosure include pesticide compositions and agricultural methods, including herbicidal compositions useful in controlling unwanted plants. The herbicides disclosed herein may be used alone in various formulations or in combination with other herbicides to control weeds in various crops.

[0002] The present disclosure includes (2,4-dichlorophenoxy)acetic acid analogs. More specifically, the present disclosure relates to (2,4-dichlorophenoxy)acetic acid analogs such as esters, amides, aminooxys, linkers, and carbon groups. [Background technology]

[0003] Protecting crops from unwanted vegetation that adversely affects crop growth is a constant problem in agriculture.To address this problem, researchers in the field of synthetic chemistry have produced a variety of chemicals and chemical formulations that are effective in controlling the growth of such unwanted plants.Many types of chemical pesticides have been disclosed in the literature, and many are commercially used.However, there remains a need for compositions and methods that are effective in controlling unwanted vegetation and that exhibit other physicochemical characteristics that make them easy to formulate and apply under various regional conditions.

[0004] (2,4-Dichlorophenoxy)acetic acid, also known as 2,4-D, is a known herbicide. 2,4-D is often used as a herbicide and defoliant. 2,4-D is often used as a herbicide in cereal crops, pastures, and orchards.

[0005] However, the various forms of 2,4-D often suffer from adverse properties such as volatility, spray drift, vapor drift, pungent odor, limited stability, limited tank mixability with other pesticide actives, and / or limited formulation flexibility.

[0006] Attempts to solve the volatility problem, including the preparation of water-soluble salts such as the dimethylamine salt of 2,4-D, have been entirely unsatisfactory because, upon volatilization of the amine, the herbicide reverts to its initial acid form, which itself is sufficiently volatile to cause damage to susceptible crops under certain unfavorable conditions.

[0007] Conventional 2,4-D ester or 2,4-D dimethylamine formulations applied during the warm summer months can cause vapor drift from evaporation of the herbicide from sprayed surfaces and subsequent damage to highly susceptible crops such as tomatoes, cotton, soybeans, sunflowers, and grapes. This can occur within hours of herbicide application.

[0008] Additionally, conventional 2,4-D ester or conventional 2,4-D dimethylamine formulations may suffer from formulation limitations such as their ability to be mixed, including tank-mixed, with other actives such as glyphosate.

[0009] Therefore, there is a need for alternative forms of 2,4-D that have reduced volatility, reduced spray drift, reduced volatile drift, reduced odor, improved tank mixability with other pesticide actives, or improved formulation flexibility. Summary of the Invention

[0010] Various compounds according to various details or embodiments are disclosed herein. Such compounds include compounds according to Formula I: [ka] (Wherein X is [ka] where: R1 is independently hydrogen, C1 to C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C10 Aryl, C5-C 10 Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; R2 is independently hydrogen, C1 to C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R3 is independently hydrogen, C1 to C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R1 and R2 together form a substituted double bond, a 3-membered ring, a 4-membered ring, a 5-membered ring, a 6-membered ring, or a 7-membered ring; A is independently O, Si, NR, and S(O) m and; A2 is independently O, N, S(O) m , substituted alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl; Y is independently O, N, or S; Z is independently O, N, or S(O) m , substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R4R5; R4 and R5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, or heteroaryl; n is 1, 2, or 3; and m is 0, 1, or 2; The compound may contain 2,4-D isooctyl esters that exhibit pesticidal activity, provided that the compound is not 2,4-D isooctyl esters.

[0011] For example, various compounds may include those described above, where X is: [ka] and R1 is independently hydrogen, C1 to C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; and R2 is independently hydrogen, C1 to C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C10 Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl.

[0012] As yet another example, various compounds may be prepared from compounds according to Formula I, where X is [ka] and R3 is independently hydrogen, C1 to C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; A is independently O, Si, NR, and S(O) m , substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R4R5; R4 and R5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, heteroaryl; and m may be 0, 1, or 2).

[0013] Further examples include compounds according to formula I, wherein X is [ka] and R2 is independently hydrogen, C1 to C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl).

[0014] Also, compounds according to formula I, wherein X is [ka] wherein A, R2, Y, Z, and A2 are as previously described.

[0015] Further examples include compounds of the formula: [ka] (In the formula, R1 is independently hydrogen, C1 to C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; R2 is independently hydrogen, C1-C16 alkyl, C1-C16 heteroalkyl, C5-C10 aryl, C5-C10 heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R3 is independently hydrogen, C1-C16 alkyl, C1-C16 heteroalkyl, C5-C10 aryl, C5-C10 heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R1 and R2 together form a substituted double bond, a 3-membered ring, a 5-membered ring, or a 7-membered ring; A is independently O, Si, NR, and S(O)m; A2 is independently O, N, S(O) m , substituted alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl; Y is independently O, N, or S; Z is independently O, N, S(O)m, substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R4R5; R4 and R5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, or heteroaryl; n is 1, 2, or 3; and m is 0, 1, or 2).

[0016] Various compositions may include any of the foregoing compounds, with the concentration of the active ingredient in the composition being 0.001 to 98 percent by weight.

[0017] Such previously described compounds may exhibit a variety of pesticidal activities, including herbicidal activity.

[0018] Also included herein is a method for controlling undesirable vegetation comprising contacting the vegetation or its locus with a herbicidally effective amount of the compound described above, or applying a herbicidally effective amount of the compound described above to the soil to prevent emergence of the vegetation.

[0019] Methods for controlling undesirable vegetation include methods in which the disclosed compounds are applied in an amount of from about 200 grams to about 2,000 grams acid equivalent per hectare (g ae / ha), such as from about 800 g ae / ha to about 1,200 g ae / ha.

[0020] Also included is a method for controlling undesirable vegetation in crops that have been made tolerant or resistant to 2,4-dichlorophenoxyacetic acid, comprising contacting the vegetation or its locus with a herbicidally effective amount of a compound according to any one of the compounds disclosed herein or applying a herbicidally effective amount of a compound according to any one of the compounds disclosed herein to the soil to prevent emergence of the vegetation. DETAILED DESCRIPTION OF THE INVENTION

[0021] The embodiments disclosed below are not intended to be exhaustive or to limit the disclosure to the precise forms disclosed in the following detailed description. Rather, the embodiments were chosen and described so that one skilled in the art may utilize its teachings.

[0022] While the various concepts of the present disclosure have been illustrated and described in detail in the drawings and description herein, the results in the drawings and their description should be considered as exemplary and not limiting in character; it being understood that merely exemplary embodiments have been shown and described, and that all changes and modifications that come within the spirit of the present disclosure are desired to be protected.

[0023] definition Unless otherwise defined, scientific and technical nomenclature has the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains.

[0024] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "about" refers to a range of values of plus or minus 10 percent, e.g., about 1.0 encompasses values from 0.9 to 1.1.

[0025] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "agriculturally active" compound includes any compound that, alone or in combination with other compounds, may be agriculturally beneficial, including compounds that inhibit plant growth that is considered undesirable in a given agricultural situation.

[0026] The examples provided in this definition are generally non-exhaustive and should not be construed as limiting the invention(s) disclosed in this document. It is understood that substituents must comply with chemical bonding rules and steric compatibility constraints with respect to the molecule to which they are attached.

[0027] As used herein, the term "alkane" may be understood to include straight-chain, branched, or cyclic, substituted or unsubstituted hydrocarbons containing one or more carbon-carbon bonds. Elements and groups that may be used to substitute the alkane include, but are not limited to, oxygen, nitrogen, sulfur, halogens, or metal-containing groups, and the bond between the hydrocarbon and the substituent may be through a carbon-carbon bond or an element other than carbon, including, but not limited to, oxygen, nitrogen, and sulfur.

[0028] As used herein, the term "alkene" may be understood to refer to a straight-chain, branched, or cyclic substituted or unsubstituted hydrocarbon containing at least one carbon-carbon double bond. Elements and groups that may be used to substitute the alkene include, but are not limited to, oxygen, nitrogen, sulfur, halogens, or metal-containing groups, and the bond between the hydrocarbon and the substituent may be through a carbon-carbon bond or an element other than carbon, including, but not limited to, oxygen, nitrogen, and sulfur.

[0029] As used herein, the term "alkyne" may be understood to include reference to a straight-chain, branched, or cyclic, substituted, or unsubstituted hydrocarbon containing at least one carbon-carbon triple bond. Elements and groups that may be used to substitute the alkyne include, but are not limited to, oxygen, nitrogen, sulfur, halogens, or metal-containing groups, and the bond between the hydrocarbon and the substituent may be through a carbon-carbon bond or an element other than carbon, including, but not limited to, oxygen, nitrogen, and sulfur.

[0030] As used herein, the term "halo" may be understood to refer to one or more of the following elements: fluoro, chloro, bromo, and iodo.

[0031] As used herein, the term "aryl" may be understood to refer to any group containing at least one aromatic ring. The aromatic ring itself may or may not be substituted. Elements and groups that may be used to substitute an aryl include, but are not limited to, groups containing oxygen, nitrogen, sulfur, halogens, or metals, and the bond between the hydrocarbon and the substituent may be via a carbon-carbon bond or an element other than carbon, including, but not limited to, oxygen, nitrogen, and sulfur.

[0032] As used herein, the term "heteroaryl" may be understood to include two aromatic rings that contain elements other than carbon in the ring structure (such elements include, but are not limited to, oxygen, nitrogen, sulfur, etc.). A heteroaryl may contain more than one ring structure. A heteroaryl may be substituted or unsubstituted, and the substituents include, but are not limited to, elements and / or groups that include oxygen, nitrogen, sulfur, halogens, or metals, and the bond between the hydrocarbon and the substituent may be through a carbon-carbon bond or an element other than carbon, including, but not limited to, oxygen, nitrogen, and sulfur.

[0033] Exemplary heteroaryls include, but are not limited to, benzofuranyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, benzothienyl, benzothiazolyl, cinnolinyl, furanyl, imidazolyl, indazolyl, indolyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxadiazolyl, oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl, thienyl, triazinyl, and triazolyl.

[0034] A saturated heterocycle is a ring structure that contains one or more elements other than carbon, including, but not limited to, oxygen, nitrogen, sulfur, etc. Exemplary saturated heterocycles include, but are not limited to, piperazinyl, piperidinyl, morpholinyl, pyrrolidinyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, and tetrahydropyranyl.

[0035] Examples of partially unsaturated heterocycles include, but are not limited to, 1,2,3,4-tetrahydroquinolinyl, 4,5-dihydro-oxazolyl, 4,5-dihydro-1H-pyrazolyl, 4,5-dihydro-isoxazolyl, and 2,3-dihydro-1,3,4-oxadiazolyl.

[0036] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "alkyl" refers to any of the following: alkane, alkene, or alkyne, and may be straight-chained, branched, or cyclic, substituted or unsubstituted; the substituents may include, but are not limited to, halogen, amino, imino, sulfone, sulfoxide, aryl, heteroaryl, ester, ketone, aldehyde, alcohol, acid, and / or ester. Unless expressly stated otherwise, any compound capable of existing as isomers, stereoisomers, or tautomers may be used in any of its herbicidally active isoforms, configurations, or tautomers.

[0037] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "AMATA" refers to Amaranthus rudis (common waterhemp).

[0038] As used herein, unless expressly stated or clearly implied otherwise, the term "AMBEL" refers to Ambrosia artemisiifolia (ragweed).

[0039] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "ABUTH" refers to Abutilon theophrasti (velvet leaf).

[0040] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "ERICA" refers to glyphosate-resistant Conyza canadensis (L.) (mulberry).

[0041] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "GLXMA" refers to Glycine max (L.) Merr., (soybean).

[0042] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "DCM" refers to dichloromethane.

[0043] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "EtOAC" refers to ethyl acetate.

[0044] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "DMF" refers to dimethylformamide.

[0045] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "K2CO3" refers to potassium carbonate.

[0046] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "EDC" refers to 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.

[0047] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "DMAP" refers to 4-dimethylaminopyridine.

[0048] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "DIPEA" refers to N,N-diisopropylethylamine.

[0049] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "Et3N" refers to triethylamine.

[0050] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "HPLC" refers to high performance liquid chromatography.

[0051] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "LC-MS" refers to liquid chromatography coupled with mass spectrometry.

[0052] As used herein, the modifier "about" used in connection with a quantity is inclusive of the stated value and has the meaning dictated by the context (e.g., it includes at least the degree of error associated with measurement of the particular quantity). When used in the context of a range, the modifier "about" should also be considered as disclosing the range defined by the absolute values of the two endpoints. For example, the range "about 2 to about 4" also discloses the range "2 to 4."

[0053] As previously described, the present disclosure includes (2,4-dichlorophenoxy)acetic acid analogs. More specifically, the present disclosure relates to (2,4-dichlorophenoxy)acetic acid analogs ("2,4-D analogs") such as esters, amides, aminooxys, linkers, and carbon groups.

[0054] Without being limited by any theory, it is believed that various 2,4-D analogs may have improved properties before or during application. Then, in the soil or within the plant, the 2,4-D analogs may be broken down into the active form of 2,4-D acid. Thus, the various 2,4-D analogs disclosed herein may benefit from the improved properties described above and yet have an acceptable pesticide profile.

[0055] Disclosed herein are 2,4-D analogs that can be converted to 2,4-D during or after application. For example, disclosed herein are 2,4-D analogs of the following formula (I): [ka] Disclosed are pesticide compositions of the formula: where X is any group that can be converted to a carboxylic acid in the soil or in a plant during or after application. For example, in some embodiments, X can be an aminooxy, an amide, a carbon chain, an ester, or a linker group.

[0056] For example, in some embodiments, X is [ka] (In the formula, R1, R2, R3, Y, Z, A, A2, and n can be as follows:

[0057] For example, in some embodiments, when X is an aminooxy group, the aminooxy group has the following exemplary formula: [ka] (In the formula, R1 is independently hydrogen, C1 to C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; R2 is independently hydrogen, C1 to C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; and R1 and R2 together may contain some of the substituted double bonds, 3-membered, 5-membered, or 7-membered rings.

[0058] For example, in some embodiments, when X is a linker group, the linker group may be, for example, a group of formula B: [ka] (Wherein A2 is independently O, N, S(O) m , substituted alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl; Y is independently O, N, or S; Z is independently O, N, or S(O) m(m=0, 1, or 2), substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R4R5; R4 and R5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, or heteroaryl; n is 1, 2, or 3; and Two or more 2,4-D molecules can be linked in one analog as follows:

[0059] An exemplary linker group is represented by the following exemplary formula B: [ka] wherein A2 is as previously described.

[0060] In some embodiments, when X is a carbon group, the carbon group has the following exemplary formula C: [ka] wherein R2 is as previously described.

[0061] In various embodiments, when X is an amide group, the amide group has the following exemplary formula D: [ka] wherein R1 and R2 are as previously described.

[0062] Some exemplary compounds within the disclosure of Formula D include the following exemplary compounds: [ka] (wherein A, R1, R2, and R3 are as previously described).

[0063] In some embodiments, when X forms an ester, the ester group has the following exemplary formula E: [ka] wherein R2 is as previously described.

[0064] As used herein, herbicide means a compound, e.g., active ingredient, that kills, controls, or otherwise adversely affects the survival, growth, and / or reproduction of plants.

[0065] As used herein, a herbicidally effective amount or vegetation controlling amount is that amount of active ingredient that causes a detrimental modifying effect on vegetation, e.g., causing deviation from natural occurrence, killing, effecting regulation, causing drying, retardation, etc.

[0066] As used herein, controlling undesirable vegetation means preventing, reducing, killing, or otherwise adversely altering the development of plants and vegetation. This specification describes a method for controlling undesirable vegetation through the application of certain herbicide combinations or compositions. Application methods include, but are not limited to, application to vegetation or its location, for example, application to the area adjacent to vegetation, as well as pre-emergence, post-emergence, foliar (spray, directed, band, local, mechanical, overgrowth, or rescue) application, and flood application (floating or submerged vegetation, spray, local, mechanical, water injection, granular spray, granular local, shake bottle, or stream spray) through manual, backpack, machine, tractor, or air (airplane and helicopter) application methods.

[0067] As used herein, plants and vegetation include, but are not limited to, germinated seeds, emerging seedlings, plants emerging from growing propagules, immature vegetation, and native vegetation.

[0068] As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity or that are or can be converted to the referenced herbicide in plants, water, or soil. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted to the corresponding carboxylic acid, which can be in a dissociated or undissociated form, for example, in plants, water, or soil, depending on the pH.

[0069] Exemplary salts include those derived from alkali or alkaline earth metals, as well as those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium, and ammonium cations of the formula:

[0070] Herbicidal activity is exhibited by the compounds when applied directly to plants or plant loci at any stage of growth. The observed effect depends on the plant species to be controlled, the plant's growth stage, application parameters such as dilution and spray droplet size, particle size of the solid component, environmental conditions at the time of use, the specific compound used, the specific adjuvant and carrier used, soil type, etc., and the amount of chemical applied. These and other factors can be adjusted to promote non-selective or selective herbicidal action. In some embodiments, the compositions described herein are applied as post-emergence applications, pre-emergence applications, or flood applications to flooded water bodies or water bodies (e.g., ponds, lakes, and rivers) to relatively immature undesirable vegetation to achieve maximum weed control.

[0071] In some aspects, the compositions and methods provided herein are utilized to control weeds in crops, including, but not limited to, direct-seeded, flood-seeded, and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn / maize, sugarcane, sunflower, rapeseed, canola, sugar beet, soybean, cotton, pineapple, pasture, grassland, rangeland, fallow, turf, tree and vine orchards, aquatic plants, plantation crops, vegetables, industrial vegetation management (IVM), and right-of-way (ROW).

[0072] Regarding this method, in certain embodiments, the method includes contacting or applying to soil or water a composition described herein with undesirable vegetation or a locus thereof to prevent the emergence or growth of the vegetation. In some embodiments, the composition is applied at a rate sufficient to control, inhibit, or promote the growth of at least one plant. In some embodiments, the compound is applied based on the total amount of active ingredient in the composition in at least one of the following ranges: from about 200 grams to about 2,000 grams acid equivalent per hectare (g ae / ha); in some embodiments, the composition is applied at a rate of from about 400 grams to about 1,500 grams; in some embodiments, the composition is applied at a rate of from about 560 grams to about 1,200 grams g ae / ha; or the composition is applied at a rate of from about 800 grams to about 1,120 grams g ae / h. In some embodiments, the method comprises contacting or applying to soil or water undesirable vegetation or a locus thereof to prevent the emergence or growth of the vegetation.

[0073] The compositions and methods provided herein are used to control undesirable vegetation, including, but not limited to, undesirable vegetation occurring in rice, cereals, wheat, barley, oats, rye, pasture, grassland, rangeland, fallow, row crops (e.g., corn / maize, sugarcane, sunflower, rapeseed, canola, sugar beet, soybean, cotton), turf, tree and vine orchards, plantation crops, vegetables, ornamentals, aquatic or non-crop situations (e.g., right-of-way, industrial vegetation management).

[0074] In some embodiments, the methods provided herein are utilized to control undesirable vegetation in rice. In certain embodiments, the undesirable vegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) RD Webster (broadleaf signalgrass, BRAPP), Digitalia sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa spp. (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa crus-pavonis (Echinochloa crus-pavonis (Kunth) Schult. (Gulf cocksprout, ECHCV), Echinochloa colonum (L.) LINK (Echinochloa colonum (L.) LINK) (Echinochloa sieboldii, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (Echinochloa oryzoides (Ard.) Fritsch) (Echinochloa sieboldii, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (Echinochloa oryzicola (Vasinger) Vasinger) (Echinochloa oryzicola, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (Echinochloa sieboldii, ECHPH), Echinochloa polystacure (Echinochloa polystachya) (Kunth) Hitchc. (Creeping Rivergrass, ECHPO), Taiwan Eye-grass (Ischaemum rugosum Salisb.) (Salamoragrass, ISCRU), Leptochloa chinensis (L.) Nees (Leptochloa chinensis (L.) Nees) (Lazegrass, LEFCH), Leptochloa fascicularis (Lam.) Gray (Leptochloa fascicularis (Lam.)) Gray) (Beared Sprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon Sprangletop, LEFPA), Oryza species (Red rice and Weedy rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (Sprangletop, PANDI), Paspalum dilatatum Poir. (Dall's grass, PASDI), Rottboellia cochinchinensis (Lour.) WDClayton (Sprangletop, ROOEX), Cyperus species (CYPSS), Cyperus difformis L.) (Cyperus peregrinus, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (Cyperus esculentus, CYPES), Cyperus iria L. (Cyperus peregrinus, CYPIR), Cyperus rotundus L. (Cyperus peregrinus, CYPRO), Cyperus serotinus Rottb. / CB Clarke (Cyperus serotinus, CYPSE), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (Fimmi), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb.) (bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla) or Schoenoplectus maritimus L. Lye (bulrush, SCPMA), Schoenoplectus mucronatus L.(Seaweed, SCPMU), Aeschynomene species (Aeschynomene, AESSS), Alternanthan philoxeroides (Mart.) Griseb. (Alternanthera philoxeroides, ALPH), Alisma plantago-aquatica L. (Arrowhead, ALSPA), Amaranthus species (Pigweed and Amaranth, AMASS), Ammannia coccinea Rottb. (Little-leaved Lythrum, AMMCO), Commelina benghalensis L. (Commelina, COMBE), Eclipta alba (L.) Hassk.) (American Eucalyptus, ECLAL), Heteranthera limosa (SW.) Willd. / Vahl (American Monarch, HETLI), Heteranthera reniformis R.&P. (Monochorhynchus, HETRE), Ipomoea spp. (Morning Glories, IPOSS), Ipomoea hederacea (L.) Jacq. (American Morning Glories, IPOHE), Lindernia dubia (L.) Pennell) (LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (Southeastern lime rose-willow, LUDLI), Ludwigia octovalvis (Jacq.) Raven (LUDOC), Monochoria korsakowii Regel & Maack (MOOKA), Monochoria vaginalis (Burm.F.) C.Presl ex Kuhth, (MOOVA), Murdannia nudiflora (L.) Brenan) Brenan) (dabweed, MUDNU), Polygonum pensylvanicum L. (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica (Wild.) Koehne (rotin), Sagittaria species (arrowweed, SAGSS), Sesbania exaltata (Raf.) Cory / Rydb.ExHill (Sesbania exaltata (Raf.) Cory / Rydb.ExHill) Hill) (Sebex), or Sphenoclea zeylanica Gaertn. (Sphenoclea zeylanica Gaertn.) (Splitweed, SPDZE).

[0075] In some aspects, the methods provided herein are utilized to control undesirable vegetation in cereals. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (black foxglove, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (oat, AVEFA), Bromus tectorum L. (browngrass, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. Retz.) (Dwarf canary grass, PHAMI), Poa annua L. (Annual bluegrass, POANN), Setaria pumila (Poir.) Roemer & JASchultes) (Yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (Green foxtail, SETVI), Amaranthus retroflexus L. (Amaranthus retroflexus, AMARE), Brassica species (BRSSS), Chenopodium album L. (Chenopodium album, CHEAL), Cirsium arvense (L.) Scop. (Siberian foxtail, CIRAR), Galium aparine L. Kochia scoparia (L.) Schrad. (Kochia, KCHSC), Lamium purpureum L. (Lampu), Matricaria recutita L.) (Wild Chamomile, MATCH), Matricaria matricarioides (Less.) Porter (Matricaria matricarioides (Less.) Porter) (Matricaria daisy, MATMT), Papaver rhoeas L. (Corne poppy, PAPRH), Polygonum convolvulus L. (Bindweed, POLCO), Salsola tragus L. (Wild fuscifer, SASKR), Sinapis species (SINSS), Sinapis arvensis L. (Wild mustard, SINAR), Stellaria media (L.) Vill. (Chickweed, STEME), Veronica persica Veronica persica Poir. (Veronica persica Poir.) (Verpe), Viola arvensis Murr. (Field violet, VIOAR), or Viola tricolor L. (Wild violet, VIOTR).

[0076] In some aspects, the methods provided herein are utilized to control undesirable vegetation in ranges, pastures, fallows, IVM, and ROW.In certain embodiments, the undesirable vegetation is selected from the group consisting of Ambrosia artemisiifolia L. (ragweed, AMBEL), Cassia obtusifolia (snake weed, CASOB), Centaurea maculosa auct.non Lam. (cornflower, CENMA), Cirsium arvense(L.)Scop. (marsh thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (cornflower, CENMA), and the like. L. (Ephesus gracilis, EPHES), Lactuca serriola L. / Torn. (Lettuce, LACSE), Plantago lanceolate L. (PLALA), Rumex obtusifolius L. (Rumex obtusifolius, RUMOB), Sida spinosa L. (Sida spinosa, SIDSP), Sinapis arvensis L. (Wild mustard, SINAR), Sonchus arvensis L. L. (Taiwan goldenrod, SONAR), Solidago spp. (Goldenrod, SOOSS), Taraxacum officinale GHWeber ex Wiggers (Common dandelion, TAROF), Trifolium repens L. (White clover, TRFRE), or Urtica dioica L. (Common nettle, URTDI).

[0077] In some aspects, the methods provided herein are utilized to control undesirable vegetation found in row crops, tree and vine crops, and perennial crops. In certain aspects, the undesirable vegetation is Alopecurus myosuroides Huds. (black foxtail, ALOMY), Avena fatua L. (oat, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) RD Webster (Surinam grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) RD (beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash) or Urochloa platyphylla (Nash) RD Webster (Urochloa platyphylla, BRAPP), Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) RD Webster (Alexandergrass, BRAPL), Cenchrus echinatus L. (CENEC), Digitaria horizontalis Willd. (Digitaria digitata, DIGHO), Digitaria insularis (L.) Mez ex Ekman (Sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv.) (Echinochloa colonum (L.) Link) (Echinochloa grass, ECHCO), Eleusine indica (L.) Gaertn.) (Eleusine citrina, ELEIN), Lolium multiflorum Lam.) (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (Land millet, PANDI), Panicum miliaceum L. (Wild millet, PANMI), Setaria faberi Herrm. (Setaria faberi, SETFA), Setaria viridis (L.) Beauv. (Setaria viridis (L.) Beauv.) (green foxtail, SETVI), Sorghum halepense (L.) Pers. (sorghum, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (sorghum, SORVU), Cyperus esculentus L. (nutmeg, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilon theophrasti Medik. Medik.) (velvet leaf, ABUTH), Amaranthus species (pigweed and amaranth, AMASS), Ambrosia artemisiifolia L. (ragweed, AMBEL), Ambrosia psilostachya DC. (false ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Anoda cristata (L.) Schlecht.(Avoneal mallow, ANVCR), Asclepias syriaca L. (Milkweed, ASCSY), Bidens pilosa L. (Bidens pilosa, BIDPI), Borrelia species (BOISS), Borrelia alata (Aubl.) DC. or Spermacocealata Aubl. (Broadleaf buttonweed, BOILF), Spermacose latifolia (Broadleaf buttonweed, BOILF), Chenopodium album L. (Chenopodium album, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L.) (Combine, COMBE), Datura stramonium L. (Datura stramonium, DATST), Daucus carota L. (Daucus carota, DAUCA), Euphorbia heterophylla L. (Dawn, EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (Euphorbia dentata Michx.) (Tooth spurge, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq.) (ragweed, ERIBO), mugwort (Erigeron canadensis L.) (mugwort, ERICA), giant ragweed (Conyza sumatrensis (Retz.) EH Walker) (large ragweed, ERIFL), sunflower (Helianthus annuus L.) (sunflower, HELAN), morning glory (Jacquemontia tamnifolia (L.) Griseb.) (smallflower morningglory, IAQTA), Ipomoea hederacea (L.) Jacq. (American morningglory, IPOHE), Ipomoea lacunosa L. (white morningglory, IPOLA), Lactuca serriola L. / Torn. (spiny lettuce, LACSE), Portulaca oleracea L. (purslane, POROL), Richardia spp. (pusley, RCHSS), Sida spp. (fern, SIDSS), Sida spinosa L. L. (Siberian Shrike, SIDSP), Sinapis arvensis L. (Wild Mustard, SINAR), Solanum ptychanthum Dunal (Eastern Black Nightshade, SOLPT), Tridax procumbens L. (Little Black Nightshade, TRQPR), or Xanthium strumarium L. (Coxbur, XANST).

[0078] In some embodiments, the methods provided herein are utilized to control undesirable vegetation in turfgrass. In certain embodiments, the undesirable vegetation is selected from the group consisting of Bellis perennis L. (Daisy, BELPE), Cyperus esculentus L. (Yellow Nutsedge, CYPES), Cyperus spp. (CYPSS), Digitaria sanguinalis (L.) Scop. (Big Crabgrass, DIGSA), Diodia virginiana L. (Diodia virginiana, DIQVI), Euphorbia spp. (Spurge, EPHSS), Glechoma hederacea L. (Shrimp, GLEHE), Hydrocotyle umbellata (Hydrocotyle umbellata), and others. umbellata L. (dollarweed, HYDUM), Kyllinga spp. (kylinga, KYLSS), Lamium amplexicaule L. (laminar weed, LAMAM), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Oxalis spp. (wood sorrel, OXASS), Plantago major L. (plantago major, PLAMA), Plantago lanceolata L. (buckhorn plantain / narrowleaf plantain, PLALA), Phyllanthus urinaria Phyllanthus (PYLTE), Rumex obtusifolius L. (Rumex obtusifolius L.) (Rumex obtusifolius L.), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (Stellaria media L.) (STEME), Taraxacum officinale GHWeber ex Wiggers (dandelion, TAROF), white clover (Trifolium repens L.) (white clover, TRFRE), or Viola species (wild violet, VIOSS).

[0079] In some aspects, the compositions and methods provided herein are utilized to control undesirable vegetation, including grass, broadleaf, and sedge weeds. In certain aspects, the compositions and methods provided herein are utilized to control undesirable vegetation, including, but not limited to, Alopecurus, Avena, Centaurea, Cyperus, Digitaria, Echinochloa, Ipomoea, Leptochloa, and Sonchus.

[0080] In some embodiments, the compounds of formula (I) or combinations thereof may be used to control Abutilon theophrasti Medik. (velvet leaf, ABUTH), Amaranthus rudis Sauer (common waterhemp, AMATA), Chenopodium album L. (chenopodium, CHEAL), Polygonum convolvulus L. (nail weed, POLCO), and Sinapis arvensis L. (field mustard, SINAR).

[0081] The compounds of formula (I) or agriculturally acceptable formulations thereof can be used to control herbicide-resistant or tolerant weeds. Exemplary resistant or tolerant weeds include herbicide inhibitors such as acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, and sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylate (ACC), and the like. ase inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins (e.g., benzoic acid, phenoxycarboxylic acids, pyridinecarboxylic acids, quinolinecarboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors (e.g., bipyridyl), 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthase inhibitors (e.g., glufosinate, bialafos acetonitriles), microtubule assembly inhibitors (e.g., benzamides, benzoic acid, dinitroanilines, phosphoramidates, pyridines), mitotic 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, benzofurans, chlorocarboxylic acids), protoporphyrinogen oxidase (PPO) inhibitors (e.g., diphenyl ether, N-phenylphthalic acid, amides, oxadiazoles, oxazolidinedione, phenylpyrazole, pyrimidinediones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS) inhibitors (e.g., amides, anilidex, furanones, phenoxybutanamides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (e.g., callistemone, isoxazoles, pyrazoles, triketones),Biotypes that are resistant or tolerant to cellulose biosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes of action such as quinclorac, and unclassified herbicides such as arylaminopropionic acid, difenzoquat, endosar, and organic arsenic compounds, include, but are not limited to, biotypes that are resistant or tolerant to multiple herbicides, biotypes that are resistant or tolerant to multiple chemical classes, biotypes that are resistant or tolerant to multiple herbicide modes of action, and biotypes with multiple resistance or tolerance mechanisms (e.g., target-site resistance or metabolic resistance).

[0082] With respect to methods for treating agricultural land to reduce or eliminate unwanted plant growth, these methods can include contacting the undesired vegetation or its locus with or applying the compositions described herein to the soil or water to prevent vegetation emergence or growth. In some embodiments, the compositions are applied at a rate of about 1 gram acid equivalent per hectare (g ae / ha) to about 400 grams active ingredient per hectare (g ai / ha), based on the total amount of active ingredient in the composition. In certain embodiments, the compositions are applied at a rate of about 4 grams acid equivalent per hectare (g ae / ha) to about 400 g ae / ha, based on the total amount of active ingredient in the composition.

[0083] Regarding this method, in certain embodiments, the method includes contacting or applying to soil or water a composition described herein with undesirable vegetation or a locus thereof to prevent the emergence or growth of the vegetation. In some embodiments, the composition is applied at a rate sufficient to control, inhibit, or promote the growth of at least one plant. In some embodiments, the compound is applied based on the total amount of active ingredient in the composition in at least one of the following ranges: from about 1 gram to about 1,000 grams of acid equivalent per hectare (g ae / ha); in some embodiments, the composition is applied at a rate of from about 1 gram to about 500 grams of acid equivalent per hectare (g ae / ha); in some embodiments, the composition is applied at a rate of from about 1 gram to about 250 grams of acid equivalent per hectare (g ae / ha); the composition is applied at a rate of from about 1 gram to about 140 grams of acid equivalent per hour (g ae / h); in some embodiments, the composition is applied at a rate of from about 1 gram to about 70 grams of acid equivalent per hectare (g ae / ha). In some embodiments, the method comprises contacting or applying to soil or water undesirable vegetation or a locus thereof to prevent the emergence or growth of the vegetation.

[0084] In some embodiments, the concentration of the active ingredient in the compositions described herein is about 0.0005 to 98 weight percent. In some embodiments, the concentration is about 0.0006 to 90 weight percent. In compositions designed to be used as concentrates, the active ingredient is present in a concentration of about 0.1 to 98 weight percent, and in certain embodiments, about 0.5 to 90 weight percent. In certain embodiments, such compositions are diluted with an inert carrier, such as water, before application. Diluted compositions typically applied to weeds or the locus of weeds contain, in certain embodiments, about 0.0006 to 3.0 weight percent, and in certain embodiments, about 0.01 to 1.0 weight percent, of the active ingredient.

[0085] The compositions can be applied to weeds or their locus by almost any conventional means of application, including, but not limited to, the use of gas dispensers, sprayers, and granular applicators. In some circumstances, these compounds and formulations thereof may be added to irrigation or paddy water and subsequently used to treat plants, soil, and other surfaces.

[0086] The described embodiments and the following examples are for illustrative purposes only and are not intended to limit the scope of the claims. Other modifications, uses, or combinations of the compositions described herein that do not depart from the spirit and scope of the claimed subject matter will be apparent to those skilled in the art.

[0087] Exemplary molecules within the foregoing formula according to various embodiments can include any of the compounds illustrated in Table 1 below.

[0088] [Table 1]

[0089] [Table 2]

[0090] [Table 3]

[0091] [Table 4]

[0092] [Table 5]

[0093] [Table 6]

[0094] [Table 7]

[0095] [Table 8]

[0096] [Table 9]

[0097] [Table 10]

[0098] [Table 11]

[0099] [Table 12]

[0100] [Table 13] [Example]

[0101] The following exemplary organic synthetic routes may be used to make some of the various compounds disclosed herein. While those of skill in the art will understand these exemplary organic synthetic routes, it is within the knowledge of those of skill in the art, with the benefit of this disclosure, to utilize these routes to affect other organic synthetic routes, whether or not explicitly described herein. Accordingly, the present disclosure is not to be considered limiting to those of skill in the art, and after reading this specification, it may be apparent to one of ordinary skill in the relevant art how to synthesize the various compounds described herein via alternative organic synthetic routes.

[0102] Additionally, many of the inputs for the synthetic pathways are commercially available, and therefore, in some instances, CAS numbers are included for selected inputs upstream of intermediates, e.g., when commercially available.

[0103] Scheme 1 [ka]

[0104] Example S1-1 Benzyl 2-(2,4-dichlorophenoxy)acetate [ka] (Bromomethyl)benzene (0.46 g, 2.71 mmol) in DMF (5 mL) was added to a mixture of K2CO3 in DMF (10 mL) at room temperature and stirred for 10 minutes. The mixture was cooled to 0 °C, and then 2,4-dichlorophenoxyacetic acid (0.5 g, 2.26 mmol) was added under an argon atmosphere and stirred at room temperature for 16 hours. Upon completion of the reaction, water (50 mL) was added, and the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–30% EtOAc:hexanes) afforded the title compound E4 (0.33 g, 47%) as an off-white solid.1 H NMR (400MHz, CDCl3): δ 7.38(d,J=2.5Hz,1H),7.29(m,5H),7.11(dd,J=8.8,2.5Hz,1H),6.73(d,J=8.8Hz,1H),5.23(s,2H),4.72(s,2H). . LCMS: m / z=333.0.1 [M+Na] + .

[0105] Scheme 2 [ka]

[0106] Example S2-1 - Compound 3: 2-(2,4-dichlorophenoxy)acetyl chloride [ka] 2,4-Dichlorophenoxyacetic acid (100 g, 0.452 mol) was dissolved in SOCl (340 mL) and the reaction mixture was heated at 80° C. for 4 h. Completion of the reaction was monitored by HPLC. Upon completion of the reaction, excess SOCl was removed in vacuo to give the title compound 3 (98.5 g, 90%) as a pale yellow oil. 1 H NMR (400 MHz, CDCl): δ 7.42 (d, J = 2.5 Hz, 1H), 7.20 (dd, J = 8.8, 2.5 Hz, 1H), 6.82 (d, J = 8.8 Hz, 1H), 4.99 (s, 2H). LCMS: No molecular ion detected.

[0107] Example S2-2 Benzoic acid (2-(2,4-dichlorophenoxy)acetoxy)methyl [ka] To a solution of 2,4-dichlorophenoxyacetic acid (1 g, 4.52 mmol) in toluene (25 mL) was added AgCO (3.74 g, 13.56 mmol) and chloromethyl benzoate (2.31 g, 13.56 mmol) at room temperature. The mixture was stirred at room temperature for 10 minutes and then heated to 80 °C for 5 hours. Upon completion of the reaction, the mixture was concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc:hexanes) afforded the title compound E7 (1 g, 63%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 7.95(m,2H),7.68(m,1H),7.53(m,3H),7.29(dd,J=8.9,2.6Hz,1H),7.14(d,J=8.9Hz,1H),6.05(s,2H),5.08(s,2H).LCMS:m / z=376.97[M+Na] + .

[0108] Example S2-3 Bis(2-(2,4-dichlorophenoxy)acetic acid)methylene [ka] To a solution of 2,4-dichlorophenoxyacetic acid (0.44 g, 2 mmol) in 1:1 DMSO:DCM (14 mL) was added KCO (0.28 g, 4 mmol), and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was then sealed and heated to 130 °C for 5 hours. Upon completion of the reaction, water (50 mL) was added; the resulting solid was collected by filtration under suction and dried by suction to give the title compound B15 (1 g, 33%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 7.62(dd,J=2.6,1.2Hz,1H),7.35(dd,J=8.8,2.6Hz,1H),7.14(d,J=9.0Hz,1H),5.86(s,1H),5.04(s,2H).LCMS:m / z=476.89[M+Na] + .

[0109] Example S2-4 Bis(2-(2,4-dichlorophenoxy)acetic acid) 1,4-phenylenebis(methylene) [ka] To a solution of 2,4-dichlorophenoxyacetic acid (1 g, 4.52 mmol) in DMF (7 mL) was added K2CO3 (0.9 g, 6.78 mmol), and the mixture was stirred at room temperature for 10 minutes. The mixture was cooled to 0 °C, and then a,a'-dibromo-p-xylene (0.6 g, 2.26 mmol) was added under an argon atmosphere and stirred at room temperature for 16 hours. Upon completion of the reaction, water (100 mL) was added, and the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded the title compound B1 (0.5 g, 42%) as a white solid. 1 H NMR (400 MHz, DMSO-d): δ 7.60 (d, J = 2.6 Hz, 2H), 7.35 (d, J = 15.0 Hz, 6H), 7.13 (d, J = 8.9 Hz, 2H), 5.21 (s, 4H), 5.03 (s, 4H). LCMS: No molecular ion detected.

[0110] Scheme 3 [ka]

[0111] Example S3-1 2-(2-(2,4-dichlorophenoxy)acetoxy)-N,N,N-trimethylethanaminium chloride [ka] To a solution of 2-hydroxy-N,N,N-trimethylethanaminium chloride (1.46 g, 10.44 mmol) in CHCl3 (20 mL) was added a solution of 2,4-dichlorophenoxyacetic acid 2,4-dichlorophenoxyacetyl chloride 3 (2.5 g, 10.44 mmol) in CHCl3 (5 mL). The reaction mixture was heated at 45 °C for 16 h. Upon completion of the reaction, the RM was concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc:hexanes) afforded the title compound E3 (0.7 g, 37%) as a white solid. 1 H NMR (400 MHz, DMSO-d): δ 7.62 (d, J = 2.6 Hz, 1H), 7.34 (m, 1H), 7.23 (d, J = 9.0 Hz, 1H), 5.01 (s, 2H), 4.58 (s, 2H), 3.69 (m, 2H), 3.16 (s, 9H). LCMS: No molecular ion detected.

[0112] Example S3-2 Oxybis(2-(2,4-dichlorophenoxy)acetic acid)oxybis(ethane-2,1-diyl) [ka] To a solution of 2,2'-oxydiethanol (0.24 g, 2.26 mmol), 2,4-dichlorophenoxyacetic acid (1 g, 4.52 mmol), and TEA (2.2 mL, 15.84 mmol) in DCM (15 mL) was added HATU (6.02 g, 15.84 mmol), and the resulting mixture was stirred at room temperature for 16 h. Upon completion of the reaction, the RM was concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-15% EtOAc:hexanes) afforded the title compound B2 (0.4 g, 35%) as an orange oil. 1 H NMR (400 MHz, DMSO-d): δ 7.59 (d, J = 2.6 Hz, 1H), 7.34 (dd, J = 8.9, 2.6 Hz, 1H), 7.10 (d, J = 8.9 Hz, 1H), 4.97 (s, 2H), 4.12 (m, 2H), 3.48 (m, 2H). LCMS: No molecular ion detected.

[0113] Scheme 4 [ka]

[0114] Example S4-1 Acetophenone O-(2-(2,4-dichlorophenoxy)acetyl)oxime [ka] To a solution of acetophenone oxime (1 g, 7.40 mmol) in CHCl (20 mL) was added NMM (2.25 g, 22.2 mmol), and the resulting mixture was stirred at room temperature for 10 min. The mixture was cooled to 0 °C, and then 2,4-dichlorophenoxyacetyl chloride 3 (2.66 g, 11.1 mmol) was added under an argon atmosphere and stirred at room temperature for 16 h. Upon completion of the reaction, water (50 mL) was added, and the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–20% EtOAc:hexanes) afforded the title compound A1 (0.3 g, 11%) as a white solid. 1 H NMR(400MHz,CDCl3):δ 7.66(m,2H),7.33(m,4H),7.17(dd,J=8.8,2.6Hz,1H),6.88(d,J=8.8Hz,1H),4.97(s,2H),2.35(s,3H).LCMS:m / z=359.67[M+Na] + .

[0115] Example S4-2 Benzaldehyde O-(2-(2,4-dichlorophenoxy)acetyl)oxime [ka]

[0116] Synthesis of intermediate A2 To a solution of benzaldehyde (2 g, 18.8 mmol) in EtOH:HO (57 mL:19 mL) was added KOAc (9.23 g, 94 mmol) and NHOH.HCl (4.71 g, 56.4 mmol), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was heated to reflux for 5 hours. Upon completion of the reaction, the RM was cooled to 0 °C, and the resulting solid was filtered and dried in vacuo to give Intermediate A2 (1.1 g, 11%) as a white crystalline solid. [ka]

[0117] Example A2 (E)-Benzaldehyde O-(2-(2,4-dichlorophenoxy)acetyl)oxime To a solution of intermediate A2 (1 g, 8.26 mmol) in CHCl3 (20 mL) was added NMM (2.51 g, 24.78 mmol), and the resulting mixture was stirred at room temperature for 10 min. The mixture was cooled to 0 °C, and then 2,4-dichlorophenoxyacetyl chloride 3 (2.97 g, 12.39 mmol) was added under an argon atmosphere, and the mixture was stirred at room temperature for 16 h. Upon completion of the reaction, water (100 mL) was added, and the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded the title compound A2 (0.3 g, 12%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 8.76(s,1H),7.70(m,2H),7.46(m,4H),7.39(dd,J=8.9,2.6Hz,1H),7.23(d,J=8.9Hz,1H),5.24(s,2H).LCMS:m / z=345.88[M+Na] + .

[0118] Example S4-3 N'-(2-(2,4-dichlorophenoxy)acetoxy)benzimidamide [ka] To a solution of N'-hydroxybenzimidamide (1 g, 0.73 mmol) in THF (20 mL) was added DIPEA (3.8 mL, 2.20 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.93 g, 0.80 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–60% EtOAc:hexanes) afforded the title compound A3 (0.44 g, 18%) as a light brown solid. 1 H NMR(400MHz,DMSO-d6):δ 7.77-7.68(m,2H),7.62(d,J=2.6Hz,1H),7.57-7.33(m,4H),7.17(d,J=8.9Hz,1H),6.99(s,2H),5.16(s,2H).LCMS:m / z=338.88[M+H] + .

[0119] Example S4-4 N'-(2-(2,4-dichlorophenoxy)acetoxy)nicotinimidamide [ka] To a solution of N'-hydroxynicotinimidamide (1 g, 0.73 mmol) in THF (20 mL) was added DIPEA (3.8 mL, 2.20 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.92 g, 0.80 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–60% EtOAc:hexanes) afforded the title compound A4 (1.18 g, 46%) as a light brown solid. 1 H NMR(400MHz,DMSO-d6):δ 8.94-8.87(m,1H),8.74-8.66(m,1H),8.14-8.05(m,1H),7.62(d,J=2.6Hz,1H),7.55-7.47( m,1H),7.40(dd,J=8.9,2.6Hz,1H),7.25-7.08(m,3H),5.18(s,2H).LCMS:m / z=339.96[M+1] + .

[0120] Example S4-5 N'-(2-(2,4-dichlorophenoxy)acetoxy)acetimidamide [ka] To a solution of N'-hydroxyacetimidamide (1 g, 1.34 mmol) in THF (20 mL) was added DIPEA (7.04 mL, 4.04 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (3.56 g, 1.48 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added, and the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–25% EtOAc:hexanes) afforded the title compound A12 (0.77 g, 21%) as a pale yellow solid. 1 H NMR(400MHz,DMSO-d6):δ 7.60(d,J=2.6Hz,1H),7.37(dd,J=8.9,2.6Hz,1H),7.10(d,J=8.9Hz,1H),6.51(s,2H),5.03(s,2H),1.77(s,3H).LCMS:m / z=276.93[M+H] + .

[0121] Example S4-6 N'-(2-(2,4-dichlorophenoxy)acetoxy)-2-phenylacetimidamide [ka] To a solution of N'-hydroxy-2-phenylethanimidamide (0.94 g, 6.26 mmol) in anhydrous THF (20 mL) was added NMM (1.27 g, 12.53 mmol), and the mixture was stirred at room temperature for 10 min. The mixture was cooled to 0 °C, and then 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) was added under an argon atmosphere and stirred at room temperature for 16 h. Upon completion of the reaction, water (50 mL) was added; the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexane) afforded the title compound A17 (0.33 g, 22%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 7.61(d,J=2.6Hz,1H),7.28(m,5H),7.11(d,J=9.0Hz,1H),6.60(s,2H),5.04(s,2H),3.39(s,2H).LCMS:m / z=374.66[M+Na] + .

[0122] Example S4-7 N'-(2-(2,4-dichlorophenoxy)acetoxy)benzimidamide [ka]

[0123] Synthesis of intermediate A5 To a solution of furan-2-carbonitrile (1 g, 1.07 mmol) and NHOH.HCl (1.5 g, 2.14 mmol) in water (10 mL) was carefully added a solution of NaCO (2.3 g, 2.14 mmol) in water (5 mL) at room temperature. The mixture was heated to reflux for 16 hours. Upon completion of the reaction, brine (50 mL) was added; the mixture was extracted with EtOAc (4 × 50 mL). The combined organic extracts were dried over NaSO, filtered, and concentrated in vacuo to give Intermediate A5 (1.2 g) as a colorless liquid. [ka]

[0124] Synthesis of A5 To a solution of intermediate A5 (0.6 g, 0.47 mmol) in THF (10 mL) was added DIPEA (2.5 mL, 1.42 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.26 g, 0.52 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–10% EtOAc:hexanes) afforded the title compound A5 (0.46 g, 30%) as a brown solid. 1 H NMR(400MHz,DMSO-d6):δ 7.85(d,J=1.0Hz,1H),7.62(d,J=2.6Hz,1H),7.42-7.35(m,1H),7.15(d,J=9.0Hz,1H),7 .09-7.02(m,1H),6.98(s,2H),6.66-6.60(m,1H),5.13(s,2H).LCMS:m / z=350.72[M+Na] + .

[0125] Example S4-8 3-((2-(2,4-dichlorophenoxy)acetoxy)imino)butan-2-one [ka] To a solution of 2,4-butanedione oxime (0.9 g, 8.39 mmol) in acetone (20 mL), potassium carbonate (3.68 g, 26.67 mmol) was added and stirred at room temperature for 10 min. The mixture was cooled to 0 °C, followed by the addition of 2,4-dichlorophenoxyacetyl chloride 3 (2.13 g, 8.39 mmol) under an argon atmosphere and stirring at room temperature for 16 h. Upon completion of the reaction, water (100 mL) was added; the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexane) afforded the title compound A8 (0.35 g, 13%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 7.64(d,J=2.6Hz,1H),7.39(dd,J=8.9,2.6Hz,1H),7.23(d,J=8.9Hz,1H),5.31(s,2H),2.41(s,3H),2.00(s,3H).LCMS:m / z=277.86[M+Na] + .

[0126] Example S4-9 N-2-(2,4-dichlorophenoxy)acetoxypropionimidate ethyl ester [ka] To a solution of ethyl N-hydroxyacetimidate (0.6 g, 6.26 mmol) in dry THF (20 mL) was added NMM (1.26 g, 12.53 mmol) and stirred at room temperature for 10 min. The mixture was cooled to 0 °C, and then 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) was added under an argon atmosphere and stirred at room temperature for 16 h. Upon completion of the reaction, water (100 mL) was added; the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded the title compound A9 (0.8 g, 64%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 7.62(d,J=2.6Hz,1H),7.38(dd,J=8.9,2.6Hz,1H),7.17(d,J=8.9Hz,1H),5.13(s,2H) ),4.11(q,J=7.0Hz,2H),2.00(s,3H),1.27(t,J=7.1Hz,3H).LCMS:m / z=305.94[M+H] + .

[0127] Example S4-10 N-2-(2,4-dichlorophenoxy)acetoxyethanimidothioic acid methyl ester [ka]

[0128] Synthesis of intermediate A10-1 A solution of acetaldehyde oxime (10 g, 169 mmol) in DMF (250 mL) was stirred at room temperature for 10 minutes. The mixture was cooled to 0 °C, and then N-chlorosuccinimide (22.6 g, 169 mmol) was added in four portions over 30 minutes; the resulting mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, an ice water:brine mixture (200 mL:200 mL) was added and stirred for 10 minutes. The mixture was extracted with EtOAc (2 × 150 mL); the combined organic extracts were washed with brine, dried over Na SO , filtered, and concentrated in vacuo to give intermediate A10-1 (0.35 g, 13%) as a white solid.

[0129] Synthesis of intermediate A10-2 To a solution of acetyl oxime chloride intermediate A10-1 (9.5 g, 101.6 mmol) in MeOH (100 mL) was added a solution of sodium thiomethoxide (16.84 g, 240.5 mmol) in MeOH (150 mL) at 0 °C. The RM was stirred at room temperature for 16 h. Upon completion of the reaction, EtOAc (300 mL) was added and the RM was filtered to remove solids. The filtrate was dried over Na2SO4, filtered, and concentrated in vacuo to give intermediate A10-2 (5.2 g) as a yellow solid.

[0130] Synthesis of A10 [ka] To a solution of intermediate A10-2 (500 mg, 3.907 mmol) in CHCl (20 mL), NMM (1.29 mL, 11.7 mmol) was added, and the mixture was stirred at room temperature for 10 min. The mixture was cooled to 0 °C, and then 2,4-dichlorophenoxyacetyl chloride 3 (1.4 g, 5.86 mmol) was added under an argon atmosphere, and the mixture was stirred at room temperature for 16 h. Upon completion of the reaction, water (100 mL) was added, and the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded the title compound A10 (0.39 g, 12%) as a white solid. 1 H NMR(400MHz,CDCl3):δ 7.39(d,J=2.6Hz,1H),7.17(dd,J=8.8,2.6Hz,1H),6.86(d,J=8.8Hz,1H),4.84(s,2H),2.39(s,3H),2.29(s,3H).LCMS:m / z=329.73[M+Na] + .

[0131] Example S4-11 N-(2-(2,4-dichlorophenoxy)acetoxy)benzimidoyl cyanide [ka] To a solution of N-hydroxybenzimidoyl cyanide (1 g, 0.68 mmol) in THF (20 mL) was added DIPEA (3.6 mL, 2.05 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.8 g, 0.75 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–20% EtOAc:hexanes) afforded the title compound A6 (0.52 g, 22%) as a light brown solid. 1 H NMR (400 MHz, DMSO-d): δ 7.95-7.89 (m, 2H), 7.76-7.69 (m, 1H), 7.68-7.60 (m, 3H), 7.41-7.36 (m, 1H), 7.34-7.29 (m, 1H), 5.41 (s, 2H). LCMS: No molecular ion detected.

[0132] Example S4-12 Diethyl 2-((2-(2,4-dichlorophenoxy)acetoxy)imino)malonate [ka] To a solution of diethyl 2-(hydroxyimino)malonate (1 g, 0.52 mmol) in DCM (20 mL) was added TEA (1.2 mL, 0.89 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (2.2 g, 0.89 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 3 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–20% EtOAc:hexanes), followed by recrystallization from hexanes:MTBE, afforded the title compound A7 (0.32 g, 16%) as a white solid. 1 H NMR (400 MHz, DMSO-d): δ 7.63 (d, J = 2.5 Hz, 1H), 7.38 (dd, J = 8.9, 2.5 Hz, 1H), 7.23 (d, J = 9.0 Hz, 1H), 5.26 (s, 2H), 4.50-4.18 (m, 4H), 1.41-1.13 (m, 6H). LCMS: No molecular ion detected.

[0133] Example S4-13 (1,1')-4-(-((2-(2,4-dichlorophenoxy)acetoxy)imino)methyl)benzaldehyde-O-(2-(2,4-dichlorophenoxy)acetyl)oxime [ka] To a solution of 4-((hydroxyimino)methyl)benzaldehyde oxime (1 g, 0.60 mmol) in THF (40 mL) was added NMM (4.5 mL, 4.08 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (8.7 g, 3.65 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–60% EtOAc:hexanes), followed by trituration with MeOH, afforded the title compound B3 (0.75 g, 22%) as an off-white solid. 1 H NMR (400 MHz, DMSO-d): δ 8.83 (s, 2H), 7.94 (s, 4H), 7.63 (d, J = 2.4 Hz, 2H), 7.43-7.34 (m, 2H), 7.24 (d, J = 8.9 Hz, 2H), 5.26 (s, 4H). LCMS: No molecular ion detected.

[0134] Example S4-14 (2,4)-Pentane-2,4-dione O,O-di(2-(2,4-dichlorophenoxy)acetyl)dioxime [ka] To a solution of 2,4-pentanedione dioxime (0.82 g, 6.27 mmol) in dry THF (20 mL) was added NMM (1.27 g, 12.53 mmol) and stirred at room temperature for 10 minutes. The mixture was cooled to 0 °C, and then 2,4-dichlorophenoxyacetyl chloride (1 g, 4.17 mmol) was added under an argon atmosphere and stirred at room temperature for 16 hours. Upon completion of the reaction, water (100 mL) was added; the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded the title compound B6 (0.35 g, 11%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 7.62(d,J=2.5Hz,2H),7.37(dd,J=8.9,2.6Hz,2H),7.15(m,2H),5.15(s,4H),3.46(s,2H),1.98(s,6H).LCMS:m / z=558.32[M+Na] + .

[0135] Scheme 5 [ka]

[0136] Example S5-1 (1,4)-N' 1 ,N' 4 -Bis(2-(2,4-dichlorophenoxy)acetoxy)terephthalimidamide [ka]

[0137] Synthesis of intermediate B5 To a solution of 1,4-cyanobenzene (2.5 g, 19.51 mmol) in ethanol (45 mL) was added hydroxylamine (50 wt%) in water (3.75 mL) and heated to reflux at room temperature for 16 hours. Upon completion of the reaction, the solid was collected by filtration to give Intermediate B5 (1 g) as a white solid. [ka]

[0138] Synthesis of B5 To a solution of intermediate B5 (0.95 g, 4.89 mmol) in anhydrous THF (200 mL) was added DIPEA (25.7 mL, 48.9 mmol), and the resulting mixture was stirred at room temperature for 10 minutes. The mixture was cooled to 0 °C, and then 2,4-dichlorophenoxyacetyl chloride 3 (6.8 g, 36.67 mmol) was added under an argon atmosphere, and the reaction mixture was stirred for 16 hours. Upon completion of the reaction, the resulting solid was collected by filtration to give the title compound B5 (0.5 g, 17%) as an off-white solid. 1 H NMR (400 MHz, DMSO-d): δ 7.82 (d, J = 7.1 Hz, 4H), 7.62 (d, J = 2.6 Hz, 2H), 7.40 (dd, J = 8.9, 2.6 Hz, 2H), 7.17 (d, J = 9.0 Hz, 2H), 7.09 (s, 4H), 5.17 (s, 4H). LCMS: No molecular ion detected.

[0139] Scheme 6 [ka]

[0140] Example S6-1 N-(2-(2,4-dichlorophenoxy)acetoxy)benzamide [ka] To a solution of N-hydroxybenzamide (0.62 g, 4.52 mmol), 2,4-dichlorophenoxyacetic acid (1 g, 4.52 mmol), and TEA (2.2 mL, 15.84 mmol) in DCM (15 mL) was added HATU (2.58 g, 6.78 mmol), and the reaction mixture was stirred at room temperature for 16 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with DCM (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–20% EtOAc:hexanes) afforded the title compound A40 (0.35 g, 23%) as a white solid. 1 H NMR (400 MHz, DMSO-d): δ 10.16 (s, 1H), 7.57 (m, 3H), 7.28 (m, 3H), 7.05 (m, 2H), 4.86 (s, 2H). LCMS: No molecular ion detected.

[0141] Example S6-2 N-(2-(2,4-dichlorophenoxy)acetoxy)-N-methylbenzamide [ka]

[0142] Synthesis of intermediate A16 To a solution of N-methylhydroxylamine hydrochloride (1.62 g, 19.4 mmol) and DMAP (0.16 g, 1.29 mmol) in DCM (10 mL) was added triethylamine (3.92 g, 38.7 mmol) at room temperature and stirred for 10 min. The reaction mixture was cooled to 0 °C, followed by the dropwise addition of benzoyl chloride (1.81 g, 12.9 mmol), and the RM was stirred at room temperature for 16 h. Upon completion of the reaction, water (50 mL) was added; the mixture was extracted with DCM (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded Intermediate A16 (1 g) as a white solid. [ka]

[0143] Synthesis of A16 To a solution of intermediate A16 (0.63 g, 4.17 mmol) in THF (20 mL) was added DIPEA (2.2 mL, 12.52 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.00 g, 4.17 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 3 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–15% EtOAc:hexanes) afforded the title compound A16 (0.45 g, 31%) as an off-white solid. 1 H NMR(400MHz,DMSO-d6):δ 7.41(m,6H),7.20(dd,J=8.9,2.6Hz,1H),6.63(d,J=8.9Hz,1H),5.07(s,2H),3.42(s,3H).LCMS:m / z=375.66[M+Na] + .

[0144] Example S6-3 N-(2-(2,4-dichlorophenoxy)acetoxy)-2-phenylacetamide [ka]

[0145] Synthesis of intermediate A13-1 Hydroxylamine hydrochloride (9 g, 129.37 mmol) was added to a biphasic mixture of KCO (18 g, 129.37 mmol) in a 2:1 mixture of EtOAc (200 mL) and HO (100 mL). The resulting solution was cooled to 0 °C, and then phenylacetyl chloride (10 g, 64.68 mmol) dissolved in a minimum amount of EtOAc was added dropwise. The reaction was stirred for 2 h while warming to room temperature. The phases were separated, and the aqueous phase was extracted with EtOAc (2 × 100 mL). The combined organic extracts were dried over NaSO, filtered, and concentrated in vacuo to give intermediate A13-1 (8 g) as a white solid. [ka]

[0146] Synthesis of A13 To a solution of 2,4-dichlorophenoxyacetic acid (0.28 g, 1.26 mmol) in DCM (7 mL), DMAP (0.31 g, 2.52 mmol), intermediate A13-1 (0.2 g, 1.32 mmol), and EDC·HCl (0.48 g, 2.52 mmol) were added and stirred at room temperature for 16 h. Upon completion of the reaction, water (100 mL) was added; the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–25% EtOAc:hexanes) afforded the title compound A13 (1 g, 43%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 12.21(s,1H),7.62(d,J=2.6Hz,1H),7.38(dd,J=8.9,2.6Hz,1H),7.21(m,5H ),7.16(d,J=8.9Hz,1H),5.21(s,2H),3.51(s,2H).LCMS:m / z=375.88[M+Na] + .

[0147] Example S6-4 N 1 ,N 4 -Bis(2-(2,6-dichlorophenoxy)acetoxy)terephthalamide [ka]

[0148] Synthesis of intermediate B4-1 To a solution of terephthaloyl dichloride (2.00 g, 10 mmol) in THF:HO (15 mL:1.5 mL), NaHCO (3.7 g, 44 mmol) was added, followed by NHOH HCl (1.53 g, 22 mmol) and stirred in an ice bath for 1 h. The phases were then separated, and the aqueous phase was extracted with EtOAc (2 × 100 mL). The combined organic extracts were dried over NaSO, filtered, and concentrated in vacuo to give Intermediate B4-1 (2 g) as a white solid.

[0149] Synthesis of intermediate B4-2 To a solution of intermediate B4-1 (2 g, 10.2 mmol) in MeOH (50 mL) was added NaOH (0.8 g, 20 mmol), and the mixture was stirred at room temperature for 2 hours. The resulting solid was filtered and dried in vacuo to give intermediate B4-2 (2 g) as a white solid. [ka]

[0150] Synthesis of B4 To a solution of intermediate B4-2 (0.5 g, 2.08 mmol) in 1,4-dioxane (6 mL), 2,4-dichlorophenoxyacetyl chloride 3 (1.7 g, 4.58 mmol) was added and stirred at room temperature for 16 h. Upon completion of the reaction, water (100 mL) was added, and the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded the title compound B4 (0.4 g, 26%) as a white solid. 1H NMR(400MHz,DMSO-d6):δ 12.85(s,2H),7.96(s,4H),7.64(d,J=2.6Hz,2H),7.43(dd,J=8.9,2.5Hz,2H),7.23(d,J=8.9Hz,2H),5.33(s,4H).LCMS:m / z=601.80[M+H] + .

[0151] Example S6-5 2-(2,4-dichlorophenoxy)piperidin-1-yl acetate [ka] To a solution of N-hydroxypiperidine (1 g, 9.89 mmol) in DMF (10 mL) was added K2CO3 (4.1 g, 29.67 mmol) at 0 °C. The mixture was stirred for 10 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (2.84 g, 11.86 mmol) in DMF (3 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 4 h. Upon completion of the reaction, water (40 mL) was added, and the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–30% EtOAc:hexanes) afforded the title compound A11 (0.3 g, 5%) as a white solid. 1 H NMR(400MHz,CDCl3):δ 7.39(d,J=2.5Hz,1H),7.16(dd,J=8.8,2.5Hz,1H),6.82(d,J=8.8Hz,1H),4.70(s,2H),3 .36(s,2H),2.65(s,2H),1.70(m,4H),1.61(s,1H),1.23(s,1H).LCMS:m / z=303.86[M+H] + .

[0152] Example S6-6 N,N-Dibenzyl-O-(2-(2,4-dichlorophenoxy)acetyl)hydroxylamine [ka] To a solution of N,N-dibenzylhydroxylamine (1 g, 4.68 mmol) in THF (20 mL) was added DIPEA (2.45 mL, 14.04 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.00 g, 5.15 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 1 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–0.7% EtOAc:hexanes) afforded the title compound A14 (0.7 g, 37%) as a white solid. 1 H NMR (400 MHz, CDCl): δ 7.30 (m, 10H), 7.28 (d, J = 2.3 Hz, 1H), 6.83 (dd, J = 8.8 Hz, 2.3 Hz, 1H), 5.68 (d, J = 8.8 Hz, 1H), 4.32 (s, 2H), 4.10 (s, 4H). LCMS: No molecular ion detected.

[0153] Example S6-7 2-(2,4-dichlorophenoxy)acetic acid 1,3-dioxoisoindolin-2-yl [ka] To a solution of 2-hydroxyisoindoline-1,3-dione (1 g, 6.13 mmol) in THF (20 mL) was added DIPEA (3.2 mL, 18.39 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.62 g, 6.74 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 1 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–0.7% EtOAc:hexanes) afforded the title compound A15 (1 g, 45%) as an off-white solid. 1 H NMR (400 MHz, CDCl): δ 7.86 (m, 2H), 7.74 (m, 2H), 7.41 (d, J = 2.5 Hz, 1H), 7.21 (m, 1H), 6.96 (d, J = 8.8 Hz, 1H), 5.10 (s, 2H). LCMS: No molecular ion detected.

[0154] Scheme 7 [ka]

[0155] Example 7-1 2-(2,4-dichlorophenoxy)-N-tosylacetamide [ka] To a solution of 2,4-dichlorophenoxyacetic acid (5 g, 22.62 mmol) in DCM (130 mL) were added DMAP (5.54 g, 45.24 mmol), p-toluoylsulfonamide (4.07 g, 23.75 mmol), and EDC·HCl (8.67 g, 45.24 mmol), and the resulting mixture was stirred at room temperature for 4 h. Upon completion of the reaction, water (100 mL) was added; the mixture was extracted with EtOAc (2 × 100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–25% EtOAc:hexanes) afforded the title compound D32 (0.80 g, 9%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 12.44(s,1H),7.81(d,J=8.2Hz,2H),7.56(d,J=2.5Hz,1H),7.43(d,J=8.1Hz,2H),7.28(dd, J=8.9,2.6Hz,1H),6.87(d,J=8.9Hz,1H),4.79(s,2H),2.40(s,3H).LCMS:m / z=374.09[M+H] + .

[0156] Scheme 8 [ka]

[0157] Example S8-1 N-(4-chlorophenyl)-2-(2,4-dichlorophenoxy)acetamide [ka] To a solution of 4-chloroaniline (0.5 g, 3.92 mmol) in dry DCM (20 mL) was added TEA (1.1 g, 11.75 mmol) at 0 °C. The mixture was stirred for 10 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (0.93 g, 3.90 mmol) in DCM (3 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 16 h. Upon completion of the reaction, water (50 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded the title compound D6 (0.37 g, 29%) as an off-white solid. 1 H NMR(400MHz,DMSO-d6):δ 10.31(s,1H),7.49(m,3H),7.24(m,3H),7.11(d,J=8.9Hz,1H),4.87(s,2H).LCMS:m / z=331.72[M+H] + .

[0158] Example S8-2 2-(2,4-dichlorophenoxy)-N-(pyridin-4-yl)acetamide [ka] To a solution of 4-aminopyridine (1.0 g, 10.63 mol) in dry DCM (30 mL) was added TEA (3.23 g, 31.89 mmol) at 0 °C. The mixture was stirred for 10 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (2.54 g, 10.63 mmol) in DCM (3 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 16 h. Upon completion of the reaction, water (50 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded the title compound D1 (0.95 g, 30%) as an off-white solid. 1H NMR(DMSO-d6):δ 10.58(s,1H),8.45(d,J=5.9Hz,2H),7.73-7.49(m,3H),7.47-7.21(m,1H),7.12(d,J=8.9Hz,1H),4.92(s,2H).LCMS:m / z=296.84[M+H] + .

[0159] Example S8-3 2-(2,4-dichlorophenoxy)-N-(isoxazol-3-yl)acetamide [ka] To a solution of 3-aminoisoxazole (1.0 g, 11.89 mol) in dry DCM (30 mL) was added TEA (3.6 g, 35.67 mmol) at 0 °C. The mixture was stirred for 10 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (2.8 g, 11.89 mmol) in DCM (3 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 16 h. Upon completion of the reaction, water (50 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded the title compound D2 (1 g, 30%) as an off-white solid. 1 H NMR(400MHz,DMSO-d6):δ 11.33(s,1H),8.83(d,J=1.7Hz,1H),7.61(d,J=2.5Hz,1H),7.37(dd,J=8.9,2.6Hz,1 H),7.09(d,J=8.9Hz,1H),6.91(d,J=1.7Hz,1H),4.95(s,2H).LCMS:m / z=286.78[M+H] + .

[0160] Scheme 9 [ka]

[0161] Example S9-1 4-chlorophenyl 2-(2,4-dichlorophenoxy)acetate [ka] To a solution of 4-chlorophenol (1 g, 7.77 mmol) in THF (20 mL) was added DIPEA (4.1 mL, 23.31 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (2.04 g, 8.55 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–10% EtOAc:hexanes) afforded the title compound E5 (0.36 g, 14%) as a brown solid. 1 H NMR (400 MHz, DMSO-d): δ 7.63 (d, J = 2.5 Hz, 1H), 7.55-7.49 (m, 2H), 7.42-7.37 (m, 1H), 7.33-7.28 (m, 1H), 7.28-7.22 (m, 2H), 5.25 (s, 2H). LCMS: No molecular ion detected.

[0162] Example S9-2 2-(2,4-dichlorophenoxy)pyrimidin-5-yl acetate [ka] To a solution of pyrimidin-5-ol (0.5 g, 5.20 mmol) in THF (20 mL) was added a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.25 g, 5.20 mmol) in THF (5 mL). The reaction was further stirred at room temperature for 3 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–45% EtOAc:hexanes) afforded the title compound E14 (0.36 g, 24%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 9.15(s,1H),8.83(s,2H),7.64(d,J=2.4Hz,1H),7.31(m,2H),5.32(s,2H).LCMS:m / z=298.73[M+H] + .

[0163] Example S9-3 1,3-dimethyl-1H-pyrazol-5-yl 2-(2,4-dichlorophenoxy)acetate [ka] To a solution of 1,3-dimethyl-1H-pyrazol-5-ol (2 g, 17.8 mmol), 2,4-dichlorophenoxyacetyl chloride 3 (3.94 g, 17.84 mmol), and TEA (8.5 mL, 62.44 mmol) in DMF (50 mL) was added HATU (17 g, 35.68 mmol), and the reaction mixture was stirred at room temperature for 3 h. Upon completion of the reaction, ice-cold water (100 mL) was added; the resulting solid was filtered and dried in vacuo to give the title compound E6 (0.36 g, 24%) as a white solid. 1 H NMR (400 MHz, DMSO-d): δ 7.64 (d, J = 2.5 Hz, 1H), 7.40 (dd, J = 8.9, 2.5 Hz, 1H), 7.34-7.19 (m, 1H), 5.91 (s, 1H), 5.34 (s, 2H), 3.56 (s, 3H), 2.11 (s, 3H). LCMS: No molecular ion detected.

[0164] Example S9-4 2-(2,4-dichlorophenoxy)-1-(2-hydroxy-1-methyl-1H-indol-3-yl)ethanone [ka] To a solution of 1-methyl-1H-indol-2-ol (0.5 g, 2.03 mmol) and 2,4-dichlorophenoxyacetyl chloride 3 (0.54 g, 2.24 mmol) in dioxane (10 mL) was added KOtBu (0.7 g, 6.11 mmol). The reaction mixture was then heated at 80 °C for 6 h. Upon completion of the reaction, water (40 mL) was added, and the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–30% EtOAc:hexanes) afforded the title compound C1 (0.14 g, 20%) as a brown solid. 1 H NMR (400 MHz, DMSO-d6): δ 12.31 (s, 1H), 7.74 (d, J = 6.4 Hz, 1H), 7.62 (d, J = 2.6 Hz, 1H), 7.36 (m, 1H), 7.30 (d, J = 8.9 Hz, 1H), 7.16 (m, 1H), 6.92 (m, 2H), 5.52 (s, 2H), 3.20 (s, 3H). LCMS: No molecular ion detected.

[0165] Scheme 10 [ka]

[0166] Example S10-1 2-(2,4-dichlorophenoxy)-N-phenoxyacetamide [ka] To a solution of O-phenylhydroxylamine (0.5 g, 4.17 mmol) in DCM (10 mL) was added TEA (0.9 mL, 6.25 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) in THF (5 mL) was added. The reaction was then allowed to warm to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–30% EtOAc:hexanes) afforded the title compound D7 (0.75 g, 52%) as a pale yellow solid. 1 H NMR(400MHz,DMSO-d6):δ 12.21(s,1H),7.62(d,J=2.0Hz,1H),7.43(d,J=7.7Hz,1H),7.34(t,J=7.6Hz,2H), 7.18(d,J=8.6Hz,1H),7.04(d,J=6.5Hz,3H),4.84(s,2H)LCMS:m / z=333.98[M+Na] + .

[0167] Example S10-2 N-(benzyloxy)-2-(2,4-dichlorophenoxy)acetamide [ka] To a solution of O-benzylhydroxylamine (0.5 g, 4.17 mmol) in DCM (10 mL) was added TEA (0.9 mL, 6.25 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) in DCM (5 mL) was added. The reaction mixture was warmed to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added, and the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–30% EtOAc:hexanes) afforded the title compound D8 (0.5 g, 37%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 11.41(s,1H),7.60(s,1H),7.39(d,J=6.3Hz,6H),7.04(d,J=8.9Hz,1H),4.83(s,2H),4.60(s,2H).LCMS:m / z=347.83[M+Na] + .

[0168] Example S10-3 2-(2,4-dichlorophenoxy)-N'-methyl-N'-phenylacetohydrazide [ka] To a solution of 1-methyl-1-phenylhydrazine (0.5 g, 4.17 mmol) in DCM (10 mL) was added TEA (1.75 mL, 12.5 mmol) at 0 °C. The mixture was stirred for 30 min, followed by the addition of a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) in DCM (5 mL). The reaction mixture was warmed to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–25% EtOAc:hexanes) afforded the title compound D11 (0.3 g, 37%) as a brown solid. 1 H NMR(400MHz,DMSO-d6):δ 10.21(s,1H),7.62(d,J=2.6Hz,1H),7.43(dd,J=8.9,2.6Hz,1H),7.24-7.11 (m,3H),6.83-6.73(m,3H),4.79(s,2H),3.09(s,3H).LCMS:m / z=324.76[M+H] + .

[0169] Example S10-4 N'-(2-(2,4-dichlorophenoxy)acetyl)-N-methylbenzohydrazide [ka] To a solution of N-methylbenzohydrazide (0.69 g, 4.17 mmol) in DCM (10 mL) was added TEA (0.9 mL, 6.25 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) in DCM (5 mL) was added. The reaction mixture was warmed to room temperature and stirred for 15 h. Upon completion of the reaction, water (40 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–30% EtOAc:hexanes) afforded the title compound D9 (0.3 g, 20%) as a white solid. 1 H NMR(400MHz,DMSO-d6):δ 10.79(s,1H),7.55(s,1H),7.52-7.41(m,3H),7.38(d,J=7.1Hz,2H),7.10(d,J=7. 4Hz,1H),6.38(d,J=7.9Hz,1H),4.54(s,2H),3.13(s,3H).LCMS:m / z=352.84[M+H] + .

[0170] Scheme 11 [ka]

[0171] Example S11-1 2-(2,4-dichlorophenoxy)-1-(1H-indazol-1-yl)ethanone [ka] To a solution of 1H-indazole (0.5 g, 4.23 mmol) in dry DCM (10 mL) was added TEA (0.85 g, 8.46 mmol) at 0 °C. The mixture was stirred for 10 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.5 g, 6.34 mmol) in DCM (3 mL) was added. The reaction was allowed to warm to room temperature and stirred for 16 h. Upon completion of the reaction, water (50 mL) was added; the mixture was extracted with EtOAc (2 × 50 mL). The combined organic extracts were washed with brine, dried over NaSO, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (silica gel; gradient elution 0–50% EtOAc:hexanes) afforded the title compound D3 (0.31 g, 23%) as a light brown solid. 1 H NMR(400MHz,DMSO-d6):δ 8.60(d,J=0.8Hz,1H),8.28(dq,J=8.4,0.9Hz,1H),7.97(dt,J=8.0,1.0Hz,1H),7.60(m, 2H),7.48(ddd,J=8.0,7.1,0.9Hz,1H),7.23(m,2H),5.81(s,2H).LCMS:m / z=320.73[M+H] + .

[0172] Example S11-2 1-(1H-benzo[d]imidazol-1-yl)-2-(2,4-dichlorophenoxy)ethanone [ka] To a solution of 1H-benzo[d]imidazole (2.67 g, 22.62 mmol), 2,4-dichlorophenoxy)acetic acid (5 g, 22.62 mmol), and TEA (7.7 mL, 56.56 mmol) in DMF (50 mL) was added HATU (12.9 g, 33.93 mmol). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, water (40 mL) was added; the precipitated solid was collected by filtration under suction and dried by suction to give the crude product. Purification by trituration with hexane:MTBE afforded the title compound D4 (2.5 g, 34%) as an off-white solid. 1H NMR (400 MHz, DMSO-d): δ 8.94 (s, 1H), 8.08 (m, 1H), 7.75 (m, 1H), 7.65 (d, J = 2.3 Hz, 1H), 7.28 (m, 4H), 5.80 (s, 2H). LCMS: No molecular ion detected.

[0173] Evaluation of pesticide activity As previously discussed, the compounds disclosed herein exhibit various pesticidal activities. For example, pesticidal activity can include herbicidal activity. Selected herbicidal activities of some compounds against various weeds and crops are illustrated in Table 3 below.

[0174] Table 2 below lists the plant growth stage at the time of application for the results illustrated in Table 3.

[0175] [Table 14]

[0176] The following examples were applied: 2,4-D choline was applied as technical grade, with the control 2,4-D isooctyl ester (CAS 25168-26-7), commercially available from Corteva Agriscience LLC under the trade name ENLIST ONE®. The technical grade material was first dissolved in 3 ml of a solvent mixture of 97.3% acetone:dimethyl sulfoxide (DMSO) and subsequently diluted with 17 ml of a solvent mixture of acetone, water, isopropyl alcohol, DMSO, Agri-Dex® crop oil concentrate (heavy range, paraffinic petroleum and nonionic emulsifier commercially available from Rosecare), and nonionic Tergitol 1557 in a 40.3:45.3:11.9:1.3:1.0:0.2 v / v ratio. All mixture sizes were 20 ml.

[0177] Postemergence application methods for herbicide evaluation. Plants were grown in a soil medium composed of 90% by volume Promix BX (Premier Tech Horticulture, Quakertown, PA) and 10% Profile Greens Grade (Profile Products LLC, Buffalo Grove, IL). Promix BX contains approximately 83% sphagnum peat moss, 13% perlite, 5% vermiculite, and specific amounts of limestone, starter fertilizer, and wetting agent. Profile Greens Grade is a sand-sized granule formed from lightly burned illite and montmorillonite clay. Several seeds of each species were planted in 10 cm square pots and watered overhead twice daily. Plant material was propagated at Corteva Global Headquarters (Indianapolis, Indiana, USA) in a greenhouse with temperatures ranging from 25 to 28°C and relative humidity of 50 to 60%. Natural light was provided at 500 μE m -2 s -1 The plants were supplemented with 1000 watt metal halide overhead lamps with an average intensity of photosynthetically active irradiance for 16 consecutive hours per day. Plants were watered overhead before herbicide application and below after herbicide application.

[0178] The appropriate amount of test material was weighed into glass vials in their technical form to deliver either 280 or 560 g acid equivalents (ae) / ha. Samples were dissolved in 3 ml of Solvent 1. Solvent 1 was 97% acetone and 3% dimethyl sulfoxide, which served as a general purpose solvent (GPS) for dissolving technical materials. If the sample did not dissolve readily, the sample bottle was placed in warm water and sonicated for 20 minutes. This usually resulted in sufficiently dissolved test material. The samples were then diluted to their final concentration using 17 ml of Solvent 2 for a total of 20 ml of spray solution. Solvent 2 contained acetone, water, isopropyl alcohol, DMSO, Agri-Dex® crop oil concentrate (heavy range, paraffinic petroleum and nonionic emulsifier commercially available from Rosecare), and nonionic Tergitol 1557 in a 40.3:45.3:11.9:1.3:1.0:0.2 v / v ratio. All percentages are listed by volume. 2,4-D choline was applied from 2,4-D choline commercially available from Corteva Agriscience LLC under the trade name ENLIST ONE® and diluted with solvent 2 for comparison with all materials in the same spray solution.

[0179] Herbicide applications were made to two replicates of each plant species at the 4- to 8-leaf stage, depending on the species. Treatments were applied with a research track sprayer (Generation III Research Sprayer manufactured by DeVries Manufacturing in Hollandale, MN, USA) calibrated to deliver a spray volume of 187 L / ha. The track sprayer was equipped with an 8003E nozzle from Spray Systems Company (North Avenue and Schmale Road, PO Box 7900, Wheaton, IL 60187) and used a spray pressure of 276 kPa and a speed of 3.1 km / h. The nozzle height was 46 cm above the plant canopy. The experimental design used for the test was a randomized complete block with two replicates per treatment. After application, the plants were placed on carts according to randomization and returned to the greenhouse. Plants were either underwatered after treatment with Indianapolis city water or fertilized three times weekly with a commercial fertilizer solution (Jack's Professional 15-5-15 4 Ca 2 Mg fertilizer (manufactured by JR PETERS INC., 6656 Grant Way, Allentown, PA 18106; www.jrpeters.com)). Visual percent control ratings were made on a 0 to 100% scale (0 being no control and 100 being complete plant death) 7, 14, and 21 days after treatment.

[0180] Determining the effects of selected experimental compounds on the growth of narrow-leaf waterfowl (Amaranthus rudis). Following the method outlined above in the postemergence application method for herbicide evaluation, the effects of representative experimental compounds on the growth of narrow-leaved waterweed (Amaranthus rudis) (AMATA) (common name tallwater hemp) were determined at two different levels of the experimental active tested (280 and 560 g acid equivalent (ae) / ha, respectively). Plants were treated with one of the compounds, and control plants were untreated. 21 days after treatment, plants were measured. Data are presented as the percent reduction in plant size compared to untreated controls. Referring to Table 3, several of the compounds tested demonstrated significant effects on the growth of this common weed species.

[0181] Determining the effects of selected experimental compounds on the growth of common ragweed (Ambrosia artemisiifolia). Following the method outlined above in the postemergence application method for herbicide evaluation, the effects of representative experimental compounds on the growth of Ambrosia artemisiifolia (AMBEL) (ragweed) were determined at two different levels of experimental active tested (280 and 560 g acid equivalent (ae) / ha, respectively). Plants were treated with one of the compounds, and control plants were untreated. 21 days after treatment, the plants were measured. Data are presented as the percent reduction in plant size compared to the untreated control. Referring to Table 4, several of the compounds tested demonstrated significant effects on the growth of this common weed species.

[0182] Determining the effects of representative experimental compounds on the growth of velvetleaf (Abutilon theophrasti) Following the method outlined above in the postemergence application method for herbicide evaluation, the effect of representative experimental compounds on the growth of Abutilon theophrasti (ABUTH) (common name velvet leaf) was determined at two different levels of experimental active tested (280 and 560 g acid equivalent (ae) / ha, respectively). Plants were treated with one of the compounds, and control plants were untreated. 21 days after treatment, the plants were measured. Data are presented as the percent reduction in plant size compared to the untreated control. Referring to Table 3, several of the compounds tested demonstrated significant effects on the growth of this common weed species.

[0183] Determining the effects of selected experimental compounds on the growth of Chenopodium album. Following the method outlined above in the postemergence application method for herbicide evaluation, the effect of representative experimental compounds on the growth of Chenopodium album (CHEAL) (common name: Chenopodium album) was determined at two different levels of experimental active tested (280 and 560 g acid equivalent (ae) / ha, respectively). Plants were treated with one of the compounds, and control plants were untreated. 21 days after treatment, the plants were measured. Data are presented as the percent reduction in plant size compared to the untreated control. Referring to Table 3, several of the compounds tested demonstrated significant effects on the growth of this common weed species.

[0184] Determining the effects of representative experimental compounds on the growth of Conyza canadensis (L.) Following the method outlined above in the postemergence application method for herbicide evaluation, the effects of representative experimental compounds on the growth of Conyza canadensis (L.), (ERICA) (common name: Conyza canadensis) were determined at two different levels of experimental active tested (280 and 560 g acid equivalent (ae) / ha, respectively). Plants were treated with one of the compounds, and control plants were untreated. 21 days after treatment, plants were measured. Data are presented as the percent reduction in plant size compared to untreated controls. Referring to Table 3, several of the compounds tested demonstrated significant effects on the growth of this common weed species.

[0185] Determining the effects of selected experimental compounds on soybean (Glycine max) growth. Following the method outlined above in the postemergence application method for herbicide evaluation, the effect of representative experimental compounds on the growth of soybean (Glycine max) (Enlist E3® trait soybeans commercially available from Corteva Agriscience®) was determined at two different levels of experimental active tested (280 and 560 g acid equivalent (ae) / ha, respectively). Plants were treated with one of the compounds, and control plants were untreated. 21 days after treatment, the plants were measured. Data are presented as the percent reduction in plant size compared to untreated controls.

[0186] [Table 15]

[0187] [Table 16]

[0188] [Table 17]

[0189]

Table 18

[0190]

Table 19

[0191] Table 20

[0192] Table 21

[0193] Table 22

[0194] Table 23

[0195] Table 24

[0196] Table 25

[0197] Table 26

[0198] Table 27

[0199] Table 28

[0200] Volatility of compounds measured by thermogravimetric analysis (TGA) Briefly, the rate of weight loss, measured in μg / min, can be used to determine the vapor pressure as shown by the simplified formula:

number

[0201] See Figure 2. A graph of weight loss as a function of time for a solid sample produces a linear curve; the slope of the curve is the rate of weight loss. When using this method to measure the volatility of an aqueous salt concentrate or liquid concentrate, the water or acetone present in the sample volatilizes before the sample of interest. The first linear decrease region of the curve is the loss of water or acetone, and the second linear region is specific to the sample of interest.

[0202] To illustrate the difference in volatility between some of the compounds disclosed herein and the commonly used 2,4-D, data from both 2,4-D choline and exemplary compounds of the present disclosure are presented in Table 4 below.

[0203] [Table 29]

[0204] Composition with reduced phytotoxicity The safened compositions comprising compounds according to Formula I may be mixed with or applied in combination with (b) an azole carboxylate safener or an agriculturally acceptable salt or ester thereof.

[0205] In some embodiments, (a) and (b) are used in an amount sufficient to induce unexpectedly enhanced herbicidal efficacy (e.g., increased damage or damage to undesirable vegetation) while still exhibiting good crop compatibility (e.g., no increased damage to the crop or minimal increased damage or damage to the crop) when compared to application of herbicidal compound (a) or (b) separately. In some embodiments, damage or damage to undesirable vegetation caused by the reduced phytotoxicity compositions and methods disclosed herein, when compared to untreated control vegetation, is rated using a scale of 0% to 100%, with 0% indicating no damage to the undesirable vegetation and 100% indicating complete destruction of the undesirable vegetation. Similarly, in some embodiments, damage or damage to crops caused by the reduced phytotoxicity compositions and methods disclosed herein, when compared to control crops treated with only herbicide or safener, is rated using a scale of 0% to 100%, with 0% indicating no damage to the crop and 100% indicating complete destruction of the crop.

[0206] In some embodiments, the synergistic effect of (a) a compound according to Formula I and (b) an azole carboxylate safener, or an agriculturally acceptable salt or ester thereof, provides unexpectedly enhanced herbicidal efficacy against undesirable vegetation, even at application rates below those typically used for herbicidal efficacy of the herbicide alone. In some embodiments, the compositions and methods disclosed herein can be used at lower application rates, based on the individual components, to achieve herbicidal efficacy comparable to that produced by the individual components at conventional application rates. In some embodiments, the synergistic effect of (a) a compound according to Formula I and (b) an azole carboxylate safener, or an agriculturally acceptable salt or ester thereof, provides unexpected protection for desired crops from damage to the crop that can be caused by the herbicide alone.

[0207] In some embodiments, the weight ratio of (a) the compound according to Formula I (g ae / ha) to (b) the azole carboxylate safener or agriculturally acceptable salt or ester thereof (g ai / ha) is 1:4.75 or more, 1:4.5 or more, 1:4.25 or more, 1:4 or more, 1:3.75 or more, 1:3.5 or 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, or the weight ratio of (a) to (b) may be 1:5 or greater, such as 1.4:1 or greater, 1.5:1 or greater, 1.6:1 or greater, 1.7:1 or greater, 1.8:1 or greater, 1.9:1 or greater, 2:1 or greater, 2.25:1 or greater, 2.5:1 or greater, 2.75:1 or greater, 3:1 or greater, 3.25:1 or greater, 3.5:1 or greater, 3.75:1 or greater, 4:1 or greater, 4.25:1 or greater, 4.5:1 or greater, 4.75:1 or greater, or 5:1 or greater; or the weight ratio of (a) to (b) may be 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 the weight ratio of (a) to (b) may vary from any of the minimum ratios to any of the maximum ratios provided above, such as 1:5 to 5:1, 1:2 to 5:1, 1:1 to 3:1, 1:3 to 4:1, or 1:1.5 to 3.5:1.

[0208] In some embodiments, (a) and (b) may be independently utilized at a purity of 90% to 100% (e.g., 95% to 100%) according to nuclear magnetic resonance (NMR) spectroscopy.

[0209] Azole carboxylate safeners In addition to the compound according to Formula I, the compositions and methods of the present disclosure may include an azole carboxylate safener or its agriculturally acceptable salt or ester. Herbicide safeners are molecules used in combination with herbicides to make them "safer" - that is, to reduce the herbicidal effect of the herbicide on crops and to improve the selectivity between the crop and the undesirable vegetation targeted by the herbicide. Herbicide safeners can be used to pretreat crop seeds before planting. Herbicide safeners can also be sprayed on plants as a mixture with herbicides or separately and sequentially with herbicides.

[0210] Azoles are a class of five-membered nitrogen heterocyclic ring compounds containing at least one additional heteroatom (e.g., nitrogen, sulfur, or oxygen) in the heterocyclic ring. Examples of azoles include, for example, pyrazoles, imidazoles, thiazoles, oxazoles, isoxazoles, and triazoles.

[0211] Azole carboxylate safeners are a class of safeners based on a carboxylate-substituted azole moiety. Examples of azole carboxylate safeners include pyrazole carboxylate safeners, imidazole carboxylate safeners, thiazole carboxylate safeners, oxazole carboxylate safeners, isoxazole carboxylate safeners, and triazole carboxylate safeners. In some embodiments, the composition may include an azole carboxylate safener selected from the group consisting of fenchlorazole, flurazole, furilazole, isoxadifen, mefenpyr, agriculturally acceptable salts or esters thereof, or combinations thereof. In some embodiments, the azole carboxylate safener may include fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, or combinations thereof.

[0212] In some embodiments, the azole carboxylate safener can include fenchlorazole, as shown below, or an agriculturally acceptable salt or ester thereof. The safening activity of fenchlorazole is described in The Pesticide Manual, Eighteenth Edition, 2016. [ka]

[0213] In some embodiments, fenchlorazole is provided as an agriculturally acceptable salt or ester. An exemplary agriculturally acceptable ester of fenchlorazole is fenchlorazole-ethyl, shown below. [ka]

[0214] In some embodiments, the azole carboxylate safener can include flurazole, shown below, or an agriculturally acceptable salt or ester thereof. The safening activity of flurazole is described in The Pesticide Manual, Eighteenth Edition, 2016. [ka]

[0215] In some embodiments, the azole carboxylate safener can include furilazole, shown below, or an agriculturally acceptable salt or ester thereof. The safening activity of furilazole is described in The Pesticide Manual, Eighteenth Edition, 2016. [ka]

[0216] In some embodiments, the azole carboxylate safener can include isoxadifen, as shown below, or an agriculturally acceptable salt or ester thereof. The safening activity of isoxadifen is described in The Pesticide Manual, Eighteenth Edition, 2016. [ka]

[0217] In some embodiments, isoxadifen is provided as an agriculturally acceptable salt or ester. An exemplary agriculturally acceptable ester of isoxadifen is isoxadifen-ethyl, shown below. [ka]

[0218] In some embodiments, the azole carboxylate safener can include mefenpyr, as shown below, or an agriculturally acceptable salt or ester thereof. The safening activity of mefenpyr is described in The Pesticide Manual, Eighteenth Edition, 2016. [ka]

[0219] In some embodiments, mefenpyr is provided as an agriculturally acceptable salt or ester. An exemplary agriculturally acceptable ester of mefenpyr is mefenpyr-diethyl, shown below. [ka]

[0220] Azole carboxylate safeners include, for example, isoxadifen and its agriculturally acceptable salts and esters. Isoxadifen has the following chemical structure: [ka] This form of isoxadifen may also be referred to as "isoxadifen-acid."

[0221] In some embodiments, the safener may comprise an isoxadifen-acid, an agriculturally acceptable salt of isoxadifen, an agriculturally acceptable ester of isoxadifen, or a mixture thereof. An exemplary agriculturally acceptable ester of isoxadifen is isoxadifen-ethyl, shown below. [ka]

[0222] In some embodiments, the azole carboxylate safener can be provided as an agriculturally acceptable ester. Suitable esters include, but are not limited to, methyl, ethyl, isopropyl, butyl, hexyl, heptyl, isoheptyl, mexyl, isooctyl, 2-ethylhexyl, and butoxyethyl esters, and aryl esters such as benzyl. Exemplary agriculturally acceptable esters of the azole carboxylate safeners described herein include methyl, ethyl, and diethyl esters.

[0223] In some embodiments, the azole carboxylate safener can include an agriculturally acceptable salt of the azole carboxylate safener, including, for example, sodium, potassium, ammonium, monoethanolammonium, diethanolammonium, triethanolammonium, monoisopropanolammonium, diisopropanolammonium, triisopropanolammonium, choline, N,N-dimethylethanolammonium, diethylammonium, dimethylammonium, trimethylammonium, triethylammonium, and isopropylammonium salts of the azole carboxylate safener.

[0224] Azole carboxylate safeners can be used to reduce phytotoxicity in crops such as wheat, barley, triticale, rye, teff, oats, corn, sorghum, foxtail millet, rice, millet, canola / rapeseed, flax, soybean, sunflower, sugar beet, cotton, sugarcane, and grasses when applied in combination with herbicides.

[0225] The azole carboxylate safener or an agriculturally acceptable salt or ester thereof may be used in an amount sufficient to elicit a safening effect. In some embodiments, the azole carboxylate safener is selected from the group consisting of fenchlorazole, fenclorim, flurazole, furilazole, isoxadifen, mefenpyr, an agriculturally acceptable salt or ester thereof, or a combination thereof, and is at least 2 g ai / ha, at least 3 g ai / ha, at least 4 g ai / ha, at least 5 g ai / ha, at least 6 g ai / ha, at least 7 g ai / ha, at least 8 g ai / ha, at least 9 g ai / ha, at least 10 g ai / ha, at least 11 g ai / ha, at least 12 g ai / ha, at least 13 g ai / ha, at least 14 g ai / ha, at least 15 g ai / ha, at least 16 g ai / ha, at least 17 g ai / ha, at least 18 g ai / ha, at least 19 g ai / ha, at least 20 g ai / ha, at least 22 g ai / ha, at least 24 g ai / ha, at least 25 g ai / ha, ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 35g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42.5g ai / ha or more, 45g ai / ha or more, 47.5g ai / ha or more, 50g ai / ha or more, 52.5g ai / ha or more, 55g ai / ha or more, 57.An amount of active ingredient per hectare (ai / ha) of 1 g ai / ha or more, such as 5 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 or more, 260 g ai / ha or more, 270 g ai / ha or more, 280 g ai / ha or more, or 290 g ai / ha or more; 290 g ai / ha or less, 280 g ai / ha or less, 270 g ai / ha or less, 260 g a / 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, 57.5 g ai / ha or less, 55 g ai / ha or less, 52.5 g ai / ha or less, 50 g ai / ha or less, 47.5 g ai / ha or less, 45 g ai / ha or less, 42.5g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 35g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 25g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g or applied to vegetation or areas adjacent to vegetation, or to soil or water, in an amount of 300g ai / ha or less, such as 1g ai / ha or less, 5g ai / ha or less, 4g ai / ha or less, 3g ai / ha or less, or 2g ai / ha or less; or in an amount within any range defined between any pair of preceding values, such as 1g ai / ha to 300g ai / ha, 5g ai / ha to 150g ai / ha, 10g ai / ha to 200g ai / ha, 20g ai / ha to 75g ai / ha, or 40g ai / ha to 100g ai / ha.

[0226] compound The present disclosure also includes formulations and methods of the compositions disclosed herein.

[0227] additives The compositions and methods disclosed herein can also be mixed with or applied with additives. In some embodiments, the additives are added sequentially. In some embodiments, the additives are added simultaneously. In some embodiments, the additive is premixed with the compound according to Formula I. In some embodiments, the additive is premixed with the azole carboxylate safener or an agriculturally acceptable salt or ester thereof.

[0228] Other pesticides Some embodiments of the disclosed reduced phytotoxicity compositions include adding one or more additional pesticidally active ingredients to the reduced phytotoxicity composition, which may include one or more herbicides, insecticides, fungicides, nematicides, miticides, arthropodicides, bactericides, plant growth regulators, or combinations thereof that are compatible with the disclosed compositions.

[0229] In some embodiments, the additive is an additional herbicide.For example, the composition described herein can be applied in combination with one or more additional herbicides to control undesirable vegetation.The composition can be formulated with one or more additional herbicides, can be tank-mixed with one or more additional herbicides, or can be applied sequentially with one or more additional herbicides, such as the following exemplary herbicides:

[0230] ALS inhibitors In addition to the compound according to Formula I, the composition may include an acetolactate synthase (ALS) inhibitor. The ALS inhibitor disrupts the production of amino acids in plants, ultimately resulting in the inhibition of DNA synthesis. Examples of ALS inhibitors include sulfonylureas, imidazolinones, triazolopyrimidine sulfonamides, pyrimidinyloxybenzoates, and sulfonylaminocarbonyltriazolinones. In some embodiments, the ALS inhibitor may include a triazolopyrimidine sulfonamide herbicide. In some embodiments, the ALS inhibitor may include an imidazolinone herbicide. In some embodiments, the ALS inhibitor may include a pyrimidinyloxybenzoate herbicide. In some embodiments, the ALS inhibitor may include a sulfonylaminocarbonyltriazolinone herbicide. In some embodiments, the ALS inhibitor may include a sulfonylurea herbicide.

[0231] In some embodiments, the composition may comprise an ALS inhibitor selected from the group consisting of imidazolinones, triazolopyrimidine sulfonamides, pyrimidinyloxybenzoates, sulfonylaminocarbonyltriazolinones, sulfonylureas, and combinations thereof. In some cases, the composition may comprise an ALS inhibitor selected from the group consisting of amidosulfuron, azimsulfuron, bispyribac, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cloransulam, cyclosulfamuron, diclosulam, ethametsurfuron, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucetosulfuron, flumetsulam, flupyrsulfuron, foramsulfuron, halosulfuron, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron. The active ingredient may include thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, triiso ...

[0232] The ALS inhibitor or an agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent to the vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of the vegetation. In some embodiments, the ALS inhibitor or agriculturally acceptable salt or ester thereof is 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, 2.5g ai / ha or more, 3g ai / ha or more, 3.5g ai / ha or more, 4g ai / ha or more, 4.5g ai / ha or more, 5g ai / ha or more, 6g ai / ha or more, 7g ai / ha or more, 8g ai / ha or more, 9g ai / ha or more, 10g ai / ha or more, 15g ai / ha or more, 20g ai / ha or more, 25g ai / ha or more, 30g ai / ha or more, 35g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 55g ai / ha or more, 60g ai / ha or more, 65g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 85g ai / ha or more, 90g ai / ha or more, 95g ai / ha or more, 100g ai / ha or more, 110g ai / ha or more, 120g ai / ha or more, 130g ai / ha or more, 140g ai / ha or more, 150g ai / ha or more, 160g ai / ha or more, 170g ai / ha or more, 180g ai / ha or more, 190g ai / ha or more, 200g ai / ha or more, 220g ai / ha or more, 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more, 280g ai / ha or more, 300g ai / ha or more, 320g ai / ha or more, 340g ai / ha or more, 350g ai / ha or more, 360g ai / ha or more, 380g ai / ha or more, 400g ai / ha or more, 420g ai / ha or more, 440g ai / ha or more, 460g ai / ha or more, 480g ai / ha or more, 500g ai / ha or more, 520g ai / ha or more, 540g ai / ha or more, 560gai / ha or more, 580g ai / ha or more, 600g ai / ha or more, 625g ai / ha or more, 650g ai / ha or more, 675g ai / ha or more, 700g ai / ha or more, 725g ai / ha or more, 750g ai / ha or more, 775g ai / ha or more, 800g ai / ha or more, 825g ai / ha or more, 850g ai / ha or more, 875g ai / ha or more, 900g ai / ha or more, 925g ai / ha or more, 950g ai / ha or more, 975g ai / ha or more, 1000g ai / ha or more, 1050g ai / ha or more, 1100g ai / ha or more, 1150g ai / ha or more, 1200g ai / ha or more, 1250g ai / ha and above, 1300g ai / ha and above, 1350g ai / ha and above, 1400g ai / ha and above, 1450g ai / ha and above, 1500g ai / ha and above, 1550g ai / ha and above, 1600g ai / ha and above, 1650g ai / ha and above, 1675g ai / ha and above, 1680g ai / ha or more, and the amount of active ingredients (ai / ha) or more is 1690g ai / ha or more; 1690g ai / ha or less, 1680g ai / ha or less, 1675g ai / ha or less, 1650g ai / ha or less, 1600g ai / ha or less, 1550g ai / ha or less, 1500g ai / ha or less, 1450g ai / ha or less, 1400g ai / ha or less, 1350g ai / ha or less, 1300g ai / ha or less, 1250g ai / ha or less, 1200g ai / ha or less, 1150g ai / ha or less, 1100g ai / ha or less, 1050g ai / ha or less, 1000g ai / ha or less, 975g ai / ha or less, 950g ai / ha or less, 925g ai / ha or less, 900g ai / ha or less, 875g ai / ha or less, 850g ai / ha or less, 825g ai / ha or less, 800g ai / ha or less, 775g ai / ha or less, 750g ai / ha or less, 725g ai / ha or less, 700g ai / ha or less, 675g ai / ha or less, 650g ai / ha or less, 625g ai / ha or less, 600g ai / ha or less, 580g ai / ha or less, 560g ai / ha or less, 540g ai / ha or less, 520g500 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 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, 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, 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 an amount of 1700 g ai / ha or less such as 0.3 g ai / ha or less; or 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 gIt is applied to vegetation or an area adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values above to any of the maximum values above, such as 10-560g ai / ha, 10-1600g ai / ha, 20-500g ai / ha, 25-140g ai / ha, 30-480g ai / ha, 40-400g ai / ha, 50-320g ai / ha, 60-300g ai / ha, 70-1250g ai / ha, 100-140g ai / ha, 140-520g ai / ha, or 250-1700g ai / ha.

[0233] Triazolopyrimidine sulfonamide herbicides In some embodiments, the composition contains a herbicidally effective amount of a compound according to Formula I and (b) florasulam, cloransulam, diclosulam, flumetsulam, metosulam, penoxulam, or piroxulam, or an agriculturally acceptable salt or ester thereof.

[0234] Floraslam The compositions and methods of the present disclosure may include florasulam or its agriculturally acceptable salts or esters. Florasulam, shown below, is a triazolopyrimidine sulfonamide that provides broad-spectrum control of many broadleaf weeds in cereals and corn. Florasulam and methods for preparing florasulam are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012. [ka]

[0235] Florasulam can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to vegetation or to soil or water to prevent the germination or growth of vegetation. In some embodiments, florasulam is present in an amount of 0.25 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, 1.1 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 / ha or more, 8.5 g ai / ha or more, 9 g ai / ha or more, or 9.5 g ai / ha or more; 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.An amount of 10g ai / ha or less, such as 25g ai / ha or less, 1g ai / ha or less, 0.9g ai / ha or less, 0.8g ai / ha or less, 0.7g ai / ha or less, 0.6g ai / ha or less, 0.5g ai / ha or less, 0.4g ai / ha or less, or 0.3g ai / ha; or 0.25 to 10g ai / ha, 0.25~7g ai / ha, 0.4~6.5g ai / ha, 0.5~6g ai / ha, 0.6~9g ai / ha, 0.7~8.5g ai / ha, 0.8~4.5g ai / ha, 1~4g ai / ha, 1.1~7.5g ai / ha, 1.5~5.75g ai / ha, 2~7.25g ai / ha, 2.25~10g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values listed above to one of the maximum values listed above, such as 3 to 8.5 g ai / ha, 3 to 8.5 g ai / ha, or 3.5 to 9.5 g ai / ha.

[0236] Clorans Rum The compositions and methods of the present disclosure may include cloransulam or its agriculturally acceptable salts or esters. Cloransulam and methods for preparing cloransulam are known in the art. In some embodiments, cloransulam may be provided as an agriculturally acceptable ester of cloransulam. Cloransulam-methyl, shown below, is [ka] It is a triazolopyrimidine sulfonamide that provides broad-spectrum control of many broadleaf weeds in soybean and other broadleaf crops. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.

[0237] Chloransulam can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to the vegetation or to soil or water in order to prevent the germination or growth of vegetation. In some embodiments, chloransulam is in an amount of 2.18 g ai / ha or more, such as 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, 4.5 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, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 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, 36 g ai / ha or more, 38 g ai / ha or more, 40 g ai / ha or more, 42 g ai / ha or more, 44 g ai / ha or more, 46 g ai / ha or more, 48 g ai / ha or more, 50 g ai / ha or more, 51 g ai / ha or more, 52 g ai / ha or more, 53 g ai / ha or more, 54 g ai / ha or more, 55 g ai / ha or more, 56 g ai / ha or more, 57 g ai / ha or more, 58 g ai / ha or more, or 59 g ai / ha or more; 60 g ai / ha or less, 59 g ai / ha or less, 58 g ai / ha or less, 57 g ai / ha or less, 56 g ai / ha or less, 55 g ai / ha or less, 54 g ai / ha or less, 53 g ai / ha or less, 52 g ai / ha or less, 51 g ai / ha or less, 50 g ai / ha or less, 48 g ai / ha or less, 46 g ai / ha or less, 44 g ai / ha or less, 42 g ai / ha or less, 40 g ai / ha or less, 38 g ai / ha or less, 36 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, 18 g ai / ha or less, 16 g ai / ha or less, 14 g ai / ha or less, 12 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.An amount of 61g ai / ha or less, such as 5g ai / ha or less, 4g ai / ha or less, 3.75g ai / ha or less, 3.5g ai / ha or less, 3.25g ai / ha or less, 3g ai / ha or less, 2.75g ai / ha or less, 2.5g ai / ha or less, or 2.25g ai / ha or less; or 2.18 to 61g ai / ha, 2.5~60g ai / ha, 2.75~44g ai / ha, 3~59g ai / ha, 3.25~60g ai / ha, 3.5~40g ai / ha, 3.75~18g ai / ha, 3.75~50g ai / ha, 4~60g ai / ha, 4~52g ai / ha, 4.25~30g ai / ha, 4.25~55g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values listed above, such as 4.5 to 51 g ai / ha, or 5 to 38 g ai / ha, to one of the maximum values listed above.

[0238] Diclosulam The compositions and methods of the present disclosure may include diclosulam or its agriculturally acceptable salts or esters. Diclosulam, shown below, is a triazolopyrimidine sulfonamide that provides broad-spectrum control of many broadleaf weeds in soybeans and peanuts. Diclosulam and methods for preparing diclosulam are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0239] Diclosulam can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to the vegetation, or to soil or water, to prevent the germination or growth of the vegetation. In some embodiments, diclosulam is in an amount of 2.18 g ai / ha or more, such as 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, 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, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 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, 31.5 g ai / ha or more, 32 g ai / ha or more, 32.5 g ai / ha or more, 33 g ai / ha or more, 33.5 g ai / ha or more, 34 g ai / ha or more, 34.5 g ai / ha or more, or 34.75 g ai / ha or more; 35 g ai / ha or less, such as 34.5 g ai / ha or less, 34 g ai / ha or less, 33.5 g ai / ha or less, 33 g ai / ha or less, 32.5 g ai / ha or less, 32 g ai / ha or less, 31.5 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, 24 g ai / ha or less, 22 g ai / ha or less, 20 g ai / ha or less, 18 g ai / ha or less, 16 g ai / ha or less, 14 g ai / ha or less, 12 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, 2.75 g ai / ha or less, 2.5 g ai / ha or less, 2.25 g ai / ha or less; or 2.18 - 35 g ai / ha, 2.5 - 34 g ai / ha, 2.It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent vegetation emergence or growth at a rate ranging from one of the minimums listed above to one of the maximums listed above, such as 75-22 g ai / ha, 3-29 g ai / ha, 3.25-34 g ai / ha, 3.25-32 g ai / ha, 3.5-30 g ai / ha, 3.75-27 g ai / ha, 4-35 g ai / ha, 4-30 g ai / ha, 4.5-18 g ai / ha, 4.5-33.5 g ai / ha, 5-32 g ai / ha, or 6-33 g ai / ha.

[0240] Flumetsulam The compositions and methods of the present disclosure may include flumetsulam or an agriculturally acceptable salt or ester thereof. Flumetsulam, shown below, is a triazolopyrimidine sulfonamide that provides broadleaf weed and foliar control in soybeans, snow peas, and corn. Flumetsulam and methods for preparing flumetsulam are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0241] Full metolachlor can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to vegetation, or to soil or water, in order to prevent the germination or growth of vegetation. In some embodiments, full metolachlor is in an amount of 2.18 g ai / ha or more, such as 2.5 g ai / ha or more, 2.75 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, 7 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, 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, 44 g ai / ha or more, 46 g ai / ha or more, 48 g ai / ha or more, 50 g ai / ha or more, 52 g ai / ha or more, 54 g ai / ha or more, 56 g ai / ha or more, 58 g ai / ha or more, 60 g ai / ha or more, 62 g ai / ha or more, 64 g ai / ha or more, 66 g ai / ha or more, 68 g ai / ha or more, 70 g ai / ha or more, 72 g ai / ha or more, 74 g ai / ha or more, or 77 g ai / ha or more; 77 g ai / ha or less, 75 g ai / ha or less, 74 g ai / ha or less, 72 g ai / ha or less, 70 g ai / ha or less, 68 g ai / ha or less, 66 g ai / ha or less, 64 g ai / ha or less, 62 g ai / ha or less, 60 g ai / ha or less, 58 g ai / ha or less, 56 g ai / ha or less, 54 g ai / ha or less, 52 g ai / ha or less, 50 g ai / ha or less, 48 g ai / ha or less, 46 g ai / ha or less, 44 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, 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, 7 g ai / ha or less, 5 g ai / ha or less, 4.5g ai / ha or less, 4g ai / ha or less, 3.5g ai / ha or less, 3g ai / ha or less, 2.75g ai / ha or less, 2.5g ai / ha or less; or 2.18-78g ai / ha, 2.5-75g ai / ha, 2.75-54g ai / ha, 3-46g ai / ha, 3~78g ai / ha, 3.5~39g ai / ha, 3.5~72g ai / ha, 4~60g ai / ha, 4~75g ai / ha, 4.5~25g ai / ha, 4.5~66g ai / ha, 5~58g ai / ha, or 9~62g It is applied to vegetation or areas adjacent to vegetation, or to soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values above, such as ai / ha, to one of the maximum values above.

[0242] Penox Slam The compositions and methods of the present disclosure may include penoxlam or an agriculturally acceptable salt or ester thereof. Penoxlam, shown below, is a triazolopyrimidine sulfonamide that provides control of Echinochloa spp. and many broadleaf, sedge, and aquatic weeds in rice. Penoxlam and methods for preparing penoxlam are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0243] Penoxulam can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to vegetation or to soil or water in order to prevent the germination or growth of vegetation. In some embodiments, Penoxulam is applied in an amount of 2.5 g ai / ha or more, such as 2.75 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, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more, 36 g ai / ha or more, 38 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, 46 g ai / ha or more, 47 g ai / ha or more, 48 g ai / ha or more, or 49 g ai / ha or more; in an amount of 50 g ai / ha or less, such as 49 g ai / ha or less, 48 g ai / ha or less, 47 g ai / ha or less, 46 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, 38 g ai / ha or less, 36 g ai / ha or less, 34 g ai / ha or less, 32 g ai / ha or less, 30 g ai / ha or less, 28 g ai / ha or less, 26 g ai / ha or less, 24 g ai / ha or less, 22 g ai / ha or less, 20 g ai / ha or less, 18 g ai / ha or less, 16 g ai / ha or less, 14 g ai / ha or less, 12 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, 4.75 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, 3.5 g ai / ha or less, 3 g ai / ha or less, or 2.75 g ai / ha or less; or 2.It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation at an amount ranging from one of the minimum values listed above to one of the maximum values listed above, such as 5-50g ai / ha, 3-28g ai / ha, 3.5-40g ai / ha, 4-34g ai / ha, 4.25-50g ai / ha, 4.5-47g ai / ha, 5-45g ai / ha, 6-36g ai / ha, 8-22g ai / ha, or 10-49g ai / ha.

[0244] Pyroxslam The compositions and methods of the present disclosure may include pyroxulam or an agriculturally acceptable salt or ester thereof. Pyroxulam, shown below, is a triazolopyrimidine sulfonamide that provides broad-spectrum post-emergence control of annual grass weeds and broadleaf weeds in cereals. Pyroxulam and methods for preparing pyroxulam are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0245] Piroxulam can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to the vegetation, or to soil or water, in order to prevent the germination or growth of the vegetation. In some embodiments, piroxulam is in an amount of 1.9 g ai / ha or more, such as 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, 4.5 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, 9.5 g ai / ha or more, 10 g ai / ha or more, 10.5 g ai / ha or more, 11 g ai / ha or more, 11.5 g ai / ha or more, 12 g ai / ha or more, 12.5 g ai / ha or more, 13 g ai / ha or more, 13.5 g ai / ha or more, 14 g ai / ha or more, 14.5 g ai / ha or more, 15 g ai / ha or more, 15.25 g ai / ha or more, 15.5 g ai / ha or more, 15.75 g ai / ha or more, 16 g ai / ha or more, 16.25 g ai / ha or more, 16.5 g ai / ha or more, 16.75 g ai / ha or more, 17 g ai / ha or more, 17.25 g ai / ha or more, 17.5 g ai / ha or more, 17.75 g ai / ha or more, 18 g ai / ha or more, 18.25 g ai / ha or more, or 18.5 g ai / ha or more; 18.5 g ai / ha or less, 18.25 g ai / ha or less, 18 g ai / ha or less, 17.75 g ai / ha or less, 17.5 g ai / ha or less, 17.25 g ai / ha or less, 17 g ai / ha or less, 16.75 g ai / ha or less, 16.5 g ai / ha or less, 16.25 g ai / ha or less, 16 g ai / ha or less, 15.75 g ai / ha or less, 15.5 g ai / ha or less, 15.25 g ai / ha or less, 15 g ai / ha or less, 14.5 g ai / ha or less, 14 g ai / ha or less, 13.5 g ai / ha or less, 13 g ai / ha or less, 12.5 g ai / ha or less, 12 g ai / ha or less, 11.5 g ai / ha or less, 11 g ai / ha or less, 10.5 g ai / ha or less, 10 g ai / ha or less, 9.5g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4.5g ai / ha or less, 4g ai / ha or less, 3.5g ai / ha or less, 3.25g ai / ha or less, 3g ai / ha or less, 2.75g ai / ha or less, 2.5g less than or equal to 18.75g ai / ha, such as less than or equal to 2.25g ai / ha; or less than or equal to 1.9~18.75g ai / ha, 2.25~18g ai / ha, 2.5~14.5g ai / ha, 2.75~12.5g ai / ha, 2.75~18.5g ai / ha, 3~13g ai / ha, 3.25~10.5g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from one of the minimum values listed above to one of the maximum values listed above, such as 3.5-16g ai / ha, 4-15.25g ai / ha, 5-18g ai / ha, 6-17.75g ai / ha, 8-16g ai / ha, 9-18g ai / ha, or 10-14.5g ai / ha.

[0246] Imidazolinone Herbicides In some embodiments, the compositions contain a herbicidally effective amount of a compound according to Formula I and (b) imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, or an agriculturally acceptable salt or ester thereof, or a combination thereof.

[0247] Imazamethabenz The compositions and methods of the present disclosure may include imazamethabenz or its agriculturally acceptable salts or esters. Imazamethabenz, shown below, is a mixture of isomers and imidazolinones that provides post-emergence control of Avena species, Alopecurus myosuroides, Apera spica-venti, and dicotyledonous weeds in wheat, barley, rye, and sunflower. Imazamethabenz and methods for preparing imazamethabenz are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0248] Imazamethabenz may be applied to vegetation or areas adjacent to vegetation, or to the soil or water to prevent the emergence or growth of vegetation, in an amount sufficient to induce a herbicidal effect. In some embodiments, imazamethabenz is at least 55g ai / ha, at least 60g ai / ha, at least 65g ai / ha, at least 70g ai / ha, at least 75g ai / ha, at least 80g ai / ha, at least 90g ai / ha, at least 95g ai / ha, at least 100g ai / ha, at least 110g ai / ha, at least 120g ai / ha, at least 130g ai / ha, at least 140g ai / ha, at least 150g ai / ha, at least 160g ai / ha, at least 170g ai / ha, at least 180g ai / ha, at least 190g ai / ha, at least 200g ai / ha, at least 220g ai / ha, at least 240g ai / ha, at least 260g ai / ha, at least 280g ai / ha, at least 300g ai / ha, amounts of 50g ai / ha or more, such as ai / ha or more, 320g ai / ha or more, 340g ai / ha or more, 360g ai / ha or more, 380g ai / ha or more, 400g ai / ha or more, 420g ai / ha or more, 440g ai / ha or more, 460g ai / ha or more, 480g ai / ha or more, 500g ai / ha or more, 520g ai / ha or more, 540g ai / ha or more, 560g ai / ha or more, 580g ai / ha or more, 600g ai / ha or more, 620g ai / ha or more, 640g ai / ha or more, 650g ai / ha or more, 660g ai / ha or more, 670g ai / ha or more, 680g ai / ha or more, or 690g ai / ha or more;690g ai / ha or less, 680g ai / ha or less, 670g ai / ha or less, 660g ai / ha or less, 650g ai / ha or less, 640g ai / ha or less, 620g ai / ha or less, 600g ai / ha or less, 580g ai / ha or less, 560g ai / ha or less, 540g ai / ha or less, 520g ai / ha or less, 500g ai / ha or less, 480g ai / ha or less, 460g ai / ha or less, 440g ai / ha or less, 420g ai / ha or less, 400g ai / ha or less, 380g ai / ha or less, 360g ai / ha or less, 340g ai / ha or less, 320g ai / ha or less, 300g less than ai / ha, 280g less than ai / ha, 260g ai / ha or less, 240g ai / ha or less, 220g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 120g 700g such as less than 110g ai / ha, less than 100g ai / ha, less than 95g ai / ha, less than 90g ai / ha, less than 85g ai / ha, less than 80g ai / ha, less than 75g ai / ha, less than 70g ai / ha, less than 65g ai / ha, less than 60g ai / ha, or less than 55g ai / ha Amount below ai / ha; or 50~700g applied to vegetation or areas adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation in an amount ranging from one of the minimums above to one of the maximums above, such as 55-400g ai / ha, 60-650g ai / ha, 75-520g ai / ha, 80-400g ai / ha, 85-500g ai / ha, 90-220g ai / ha, 100-700g ai / ha, 100-500g ai / ha, 110-640g ai / ha, 120-420g ai / ha, 120-500g ai / ha, 140-670g ai / ha, or 150-580g ai / ha;

[0249] Imazamox The compositions and methods of the present disclosure may include imazamox or its agriculturally acceptable salts or esters. Imazamox, shown below, is an imidazolinone that provides pre- and post-emergence control of broadleaf and grass weeds in, for example, rice, corn, rapeseed, alfalfa, pea, and bean. Imazamox and methods for preparing imazamox are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0250] Imazamox may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, imazamox is 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 ai / ha or more, 18g ai / ha or more, 19g ai / ha or more, 20g ai / ha or more, 21g ai / ha or more, 22g ai / ha or more, 23g ai / ha or more, 24g ai / ha or more, 25g ai / ha or more, 26g ai / ha or more, 27g ai / ha or more, 28g ai / ha or more, 29g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g amounts of 5g ai / ha or more, such as 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, or 58g ai / ha or more;58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less, 29g ai / ha or less, 28g ai / ha or less, 27g ai / ha or less, 26g ai / ha or less, 25g ai / ha or less, 24g ai / ha or less, 23g ai / ha or less, 22g ai / ha or less, 21g ai / ha or less, 20g ai / ha or less, 19g less than ai / ha, 18g 60g such as less than 17g ai / ha, less than 16g ai / ha, less than 15g ai / ha, less than 14g ai / ha, less than 13g ai / ha, less than 12g ai / ha, less than 11g ai / ha, less than 10g ai / ha, less than 9g ai / ha, less than 8g ai / ha, less than 7g ai / ha, or less than 6g ai / ha or less than 5-60g ai / ha, 5-52g ai / ha, 6-46g ai / ha, 6-54g ai / ha, 7-38g ai / ha, 7-50g ai / ha, 8-48g ai / ha, 9-45g ai / ha, 10-40g ai / ha, 10-58g ai / ha, 11-36g ai / ha, 12~54g applied to vegetation or areas adjacent to vegetation, or to soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values listed above to one of the maximum values listed above, such as 1000 g ai / ha, 13-60 g ai / ha, or 15-48 g ai / ha;

[0251] Imazapic The compositions and methods of the present disclosure may include imazapic or its agriculturally acceptable salt or ester. Imazapic, shown below, is an imidazolinone that provides pre-emergence and post-emergence control of a wide range of annual and perennial weeds in pastures, rangelands, and non-crop areas. Imazapic and methods for preparing imazapic are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0252] Imazapic may be applied to vegetation or areas adjacent to vegetation, or to the soil or water to prevent the emergence or growth of vegetation, in an amount sufficient to elicit a herbicidal effect. In some embodiments, imazapic is at least 18g ai / ha, at least 19g ai / ha, at least 20g ai / ha, at least 22g ai / ha, at least 24g ai / ha, at least 26g ai / ha, at least 28g ai / ha, at least 30g ai / ha, at least 35g ai / ha, at least 40g ai / ha, at least 45g ai / ha, at least 50g ai / ha, at least 45g ai / ha, at least 50g ai / ha, at least 60g ai / ha, at least 70g ai / ha, at least 80g ai / ha, at least 90g ai / ha, at least 100g ai / ha, at least 110g ai / ha, at least 120g ai / ha, at least 130g ai / ha, at least 140g ai / ha, at least 150g ai / ha, at least 155g ai / ha, at least 160g ai / ha, at least 170g ai / ha, at least 180g ai / ha, at least 190g ai / ha, at least 20g ai / ha, at least 22g ai / ha, at least 24g ai / ha, at least 26g ai / ha, at least 28g ai / ha, at least 30g ai / ha, at least 35g ai / ha, at least 40g ai / ha, at least 45g ai / ha, at least 50g ai / ha, at least 60g ai / ha, at least 70g ai / ha, at least 80g ai / ha, at least 90g ai / ha, at least 100g ai / ha, at least 110 ai / ha or more, 165g ai / ha or more, 170g ai / ha or more, 175g ai / ha or more, 180g ai / ha or more, 185g ai / ha or more, 190g ai / ha or more, 195g ai / ha or more, 200g ai / ha or more, 205g ai / ha or more, 210g ai / ha or more, or 215g 17. such as more than ai / ha.5g ai / ha or more; 215g ai / ha or less, 210g ai / ha or less, 205g ai / ha or less, 200g ai / ha or less, 195g ai / ha or less, 190g ai / ha or less, 185g ai / ha or less, 180g ai / ha or less, 175g ai / ha or less, 170g ai / ha or less, 165g ai / ha or less, 160g ai / ha or less, 155g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 120g ai / ha or less, 110g ai / ha or less, 100g ai / ha or less, 90g ai / ha or less, 80g ai / ha or less, 70g ai / ha or less, 60g less than ai / ha, 50g 220g such as less than 45g ai / ha, less than 40g ai / ha, less than 35g ai / ha, less than 30g ai / ha, less than 28g ai / ha, less than 26g ai / ha, less than 24g ai / ha, less than 22g ai / ha, less than 20g ai / ha, less than 19g ai / ha, or less than 18g ai / ha ai / ha or less; or 17.5~220g ai / ha, 17.5~210g ai / ha, 18~200g ai / ha, 19~120g ai / ha, 20~210g ai / ha, 20~170g ai / ha, 22~190g ai / ha, 24~175g ai / ha, 26~210g ai / ha, 26~160g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation in an amount ranging from one of the minimum values listed above to one of the maximum values listed above, such as 30-190g ai / ha, 30-140g ai / ha, 35-220g ai / ha, or 45-215g ai / ha.

[0253] Imazapyr The compositions and methods of the present disclosure may include imazapyr or its agriculturally acceptable salts or esters. Imazapyr, shown below, is an imidazolinone that provides pre-emergence and post-emergence control of annual and perennial grasses, broadleaf weeds, scrub, and trees. Imazapyr and methods for preparing imazapyr are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0254] Imazapyr can be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, imazapyr is administered at a concentration of at least 120g ai / ha, at least 125g ai / ha, at least 130g ai / ha, at least 140g ai / ha, at least 150g ai / ha, at least 160g ai / ha, at least 170g ai / ha, at least 180g ai / ha, at least 190g ai / ha, at least 200g ai / ha, at least 225g ai / ha, at least 250g ai / ha, at least 275g ai / ha, at least 300g ai / ha, at least 325g ai / ha, at least 350g ai / ha, at least 375g ai / ha, at least 400g ai / ha, at least 425g ai / ha, at least 450g ai / ha, at least 475g ai / ha, at least 500g ai / ha, at least 600g ai / ha, at least 700g ai / ha, at least 800g ai / ha, at least 900g ai / ha, at least 1000g ai / ha, at least 1100g ai / ha, at least 1200g ai / ha, at least 1300g ai / ha, at least 1400g ai / ha, at least 1500g ai / ha, at least 1600g ai / ha, at least 170g ai / ha, at least 180g ai / ha, at least 190g ai / ha, at least 200g ai / ha, at least 225g ai / ha, at least 250g ai / ha, at least 275g ai / ha, at least 300g ai / amounts of 100g ai / ha or more, such as ai / ha or more, 800g ai / ha or more, 900g ai / ha or more, 1000g ai / ha or more, 1050g ai / ha or more, 1100g ai / ha or more, 1150g ai / ha or more, 1200g ai / ha or more, 1250g ai / ha or more, 1300g ai / ha or more, 1350g ai / ha or more, 1400g ai / ha or more, 1450g ai / ha or more, 1500g ai / ha or more, 1550g ai / ha or more, 1600g ai / ha or more, 1620g ai / ha or more, 1640g ai / ha or more, 1660g ai / ha or more, or 1680g ai / ha or more;1700g ai / ha or less (for example, 1680g ai / ha or less, 1660g ai / ha or less, 1640g ai / ha or less, 1620g ai / ha or less, 1600g ai / ha or less, 1550g ai / ha or less, 1500g ai / ha or less, 1450g ai / ha or less, 1400g ai / ha or less, 1350g ai / ha or less, 1300g ai / ha or less, 1250g ai / ha or less, 1200g ai / ha or less, 1150g ai / ha or less, 1100g ai / ha or less, 1050g ai / ha or less, 1000g ai / ha or less, 900g ai / ha or less, 800g ai / ha or less, 700g less than ai / ha, 600g less than ai / ha, 500g ai / ha or less, 475g ai / ha or less, 450g ai / ha or less, 425g ai / ha or less, 400g ai / ha or less, 375g ai / ha or less, 350g ai / ha or less, 325g ai / ha or less, 300g ai / ha or less, 275g ai / ha or less, 250g ai / ha or less, 225g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 125g ai / ha or less, 120g ai / ha or less, or 110g ai / ha); or 100~1700g ai / ha, 125-850g ai / ha, 130-700g ai / ha, 150-1000g ai / ha, 160-475g ai / ha, 170-1660g ai / ha, 180-1500g ai / ha, 190-1050g ai / ha, 200-700g ai / ha, 250-1500g ai / ha, 325-1200g ai / ha, 450-1500g ai / ha, 500-900g ai / ha, or 110-1000g ai / ha, applied to vegetation or areas adjacent to vegetation, or to soil or water, to inhibit the emergence or growth of vegetation in an amount ranging from one of the minimum values above to one of the maximum values above;

[0255] Imazethapyr The compositions and methods of the present disclosure may include imazethapyr or its agriculturally acceptable salts or esters. Imazethapyr, shown below, is an imidazolinone that controls many major annual and perennial grass and broadleaf weeds in most major crops. Imazethapyr and methods for preparing imazethapyr are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0256] Imazethapyr can be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, imazethapyr is 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, 18 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 60g ai / ha or more, 70g ai / ha or more, 80g ai / ha or more, 90g ai / ha or more, 100g ai / ha or more, 120g ai / ha or more, 130g ai / ha or more, 140g ai / ha or more, 150g ai / ha or more, 160g ai / ha or more, 170g ai / ha or more, 180g ai / ha or more, 190g ai / ha or more, 200g ai / ha or more, 210g ai / ha or more, 220g ai / ha or more, 230g ai / ha or more, 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more, 270g 8. such as 272g ai / ha or more, 274g ai / ha or more, 276g ai / ha or more, or 278g ai / ha or more.75g ai / ha or more; 278g ai / ha or less, 276g ai / ha or less, 274g ai / ha or less, 272g ai / ha or less, 270g ai / ha or less, 260g ai / ha or less, 250g ai / ha or less, 240g ai / ha or less, 230g ai / ha or less, 220g ai / ha or less, 210g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 120g ai / ha or less, 110g ai / ha or less, 100g less than ai / ha, 90g less than ai / ha, 80g less than 70g ai / ha, less than 60g ai / ha, less than 50g ai / ha, less than 45g ai / ha, less than 40g ai / ha, less than 35g ai / ha, less than 30g ai / ha, less than 25g ai / ha, less than 20g ai / ha, less than 18g ai / ha, less than 16g ai / ha, less than 15g ai / ha, 14g 280g ai / ha or less, such as less than 13g ai / ha, less than 12g ai / ha, less than 11g ai / ha, less than 10g ai / ha, or less than 9g ai / ha; or 8.75~280g ai / ha, 8.75~170g ai / ha, 9~220g ai / ha, 10~260g ai / ha, 10~150g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from one of the minimum values above to one of the maximum values above, such as 11-220g ai / ha, 12-200g ai / ha, 13-274g ai / ha, 15-230g ai / ha, 16-160g ai / ha, 18-280g ai / ha, 20-210g ai / ha, 20-190g ai / ha, or 25-272g ai / ha.

[0257] Pyrimidinyloxybenzoate herbicides In some embodiments, the compositions contain a herbicidally effective amount of a compound according to Formula I and (b) bispyribac, pyribenzoxim, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, or an agriculturally acceptable salt or ester thereof, or a combination thereof.

[0258] Bispyribac The compositions and methods of the present disclosure may include bispyribac or an agriculturally acceptable salt or ester thereof. Bispyribac-sodium, shown below, is a pyrimidinyloxybenzoate that provides grass, sedge, and broadleaf weed control in, for example, direct-seeded and flooded rice and turf. Bispyribac-sodium and methods for preparing bispyribac-sodium are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0259] Bispyribac may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, Bispyribac is at least 7.5g ai / ha, at least 10g ai / ha, at least 12.5g ai / ha, at least 15g ai / ha, at least 17.5g ai / ha, at least 20g ai / ha, at least 22.5g ai / ha, at least 25g ai / ha, at least 27.5g ai / ha, at least 30g ai / ha, at least 32.5g ai / ha, at least 35g ai / ha, at least 37.5g ai / ha, at least 40g ai / ha, at least 42.5g ai / ha, at least 45g ai / ha, at least 47.5g ai / ha, at least 50g ai / ha, at least 52.5g ai / ha, at least 55g ai / ha, at least 57.5g ai / ha, at least 60g ai / ha, at least 62.5g ai / ha, at least 65g ai / ha, ai / ha or more, 67.5g ai / ha or more, 70g ai / ha or more, 72.5g ai / ha or more, 75g ai / ha or more, 77.5g ai / ha or more, 80g ai / ha or more, 82.5g ai / ha or more, 85g ai / ha or more, 87.5g ai / ha or more, 90g ai / ha or more, 92.5g More than 97.5g ai / ha, less than 95g ai / ha, less than 92.5g ai / ha, less than 90g ai / ha, less than 87.5g ai / ha, less than 85g ai / ha, less than 82.5g ai / ha, 80g less than ai / ha, 77.5g less than ai / ha, 75g ai / ha or less, 72.5g ai / ha or less, 70g ai / ha or less, 67.5g ai / ha or less, 65g ai / ha or less, 62.5g ai / ha or less, 60g ai / ha or less, 57.5g ai / ha or less, 55g ai / ha or less, 52.5g ai / ha or less, 50g ai / ha or less, 47.5g ai / ha or less, 45g ai / ha or less, 42.5g ai / ha or less, 40g ai / ha or less, 37.5g ai / ha or less, 35g ai / ha or less, 32.5g ai / ha or less, 30g ai / ha or less, 27.5g ai / ha or less, 25g ai / ha or less, 22.Amounts below 100g ai / ha, such as below 5g ai / ha, below 20g ai / ha, below 17.5g ai / ha, below 15g ai / ha, below 12.5g ai / ha, below 10g ai / ha, or below 7.5g ai / ha; or between 5 and 100g ai / ha, between 5 and 90g ai / ha, between 7.5 and 45g ai / ha, 10~55g ai / ha, 15~90g ai / ha, 20~50g ai / ha, 22.5~90g ai / ha, 25~52.5g ai / ha, 25~80g ai / ha, 25~65g ai / ha, 27.5~60g ai / ha, 27.5~47.5g ai / ha, 30~85g ai / ha, or 40~95g It is applied to vegetation or areas adjacent to vegetation, or to soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values above, such as ai / ha, to one of the maximum values above.

[0260] Pyribenzoxim The compositions and methods of the present disclosure may include pyribenzoxim or an agriculturally acceptable salt or ester thereof. Pyribenzoxim, shown below, is a pyrimidinyloxybenzoate that provides post-emergence control of barnyardgrass, black-grass grass, and Polygonum species in rice, wheat, and lawngrass. Pyribenzoxim and methods for preparing pyribenzoxim are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0261] Pyribenzoxim may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, the pyribenzoxime is at least 8g ai / ha, at least 9g ai / ha, at least 10g ai / ha, at least 11g ai / ha, at least 12g ai / ha, at least 13g ai / ha, at least 14g ai / ha, at least 15g ai / ha, at least 16g ai / ha, at least 17g ai / ha, at least 18g ai / ha, at least 19g ai / ha ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, or 69g ai / ha or more.5g ai / ha or more; 69g ai / ha or less, 68g ai / ha or less, 66g ai / ha or less, 64g ai / ha or less, 62g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g less than 46g ai / ha, less than 44g ai / ha, less than 42g ai / ha, less than 40g ai / ha, less than 38g ai / ha, less than 36g ai / ha, less than 34g ai / ha, less than 32g ai / ha, less than 30g ai / ha, less than 28g ai / ha, less than 26g ai / ha, less than 24g ai / ha, 22g less than ai / ha, 20g 70g such as less than 19g ai / ha, less than 18g ai / ha, less than 17g ai / ha, less than 16g ai / ha, less than 15g ai / ha, less than 14g ai / ha, less than 13g ai / ha, less than 12g ai / ha, less than 11g ai / ha, less than 10g ai / ha, less than 9g ai / ha, or less than 8g ai / ha ai / ha or less; or 7.5-70g ai / ha, 7.5-68g ai / ha, 7.5-52g ai / ha, 8-60g ai / ha, 9-38g ai / ha, 9-64g ai / ha, 10-66g ai / ha, 10-44g ai / ha, 10-40g ai / ha, 11-62g ai / ha, 12~46g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values listed above to one of the maximum values listed above, such as 1000 g ai / ha, 13-70 g ai / ha, 15-54 g ai / ha, or 20-64 g ai / ha.

[0262] Piriftalid The compositions and methods of the present disclosure may include pyriftalid or an agriculturally acceptable salt or ester thereof. Piriftalid, shown below, is a pyrimidinyloxybenzoate that provides grass weed control in rice. Piriftalid, and [ka] Methods for preparing pyriftalid are known in the art, and its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.

[0263] Pyriftalid may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, pyriftalid is at least 22g ai / ha, at least 25g ai / ha, at least 30g ai / ha, at least 35g ai / ha, at least 40g ai / ha, at least 45g ai / ha, at least 50g ai / ha, at least 55g ai / ha, at least 60g ai / ha, at least 70g ai / ha, at least 80g ai / ha, at least 90g ai / ha, at least 100g ai / ha, at least 120g ai / ha, at least 130g ai / ha, at least 140g ai / ha, at least 150g ai / ha, at least 160g ai / ha, at least 170g ai / ha, at least 180g ai / ha, at least 190g ai / ha, at least 200g ai / ha, at least 210g ai / ha, at least 220g ai / ha, at least 230g ai / ha, amounts of 20g ai / ha or more, such as 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more, 270g ai / ha or more, 280g ai / ha or more, 290g ai / ha or more, 300g ai / ha or more, 310g ai / ha or more, 320g ai / ha or more, 330g ai / ha or more, 340g ai / ha or more, or 345g ai / ha or more;345g ai / ha or less, 340g ai / ha or less, 330g ai / ha or less, 320g ai / ha or less, 310g ai / ha or less, 300g ai / ha or less, 290g ai / ha or less, 280g ai / ha or less, 270g ai / ha or less, 260g ai / ha or less, 250g ai / ha or less, 240g ai / ha or less, 230g ai / ha or less, 220g ai / ha or less, 210g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 120g ai / ha or less, 110g ai / ha or less, 100g ai / ha or less, 90g ai / ha or less, 80g ai / ha or less, 70g ai / ha or less, 60g ai / ha or less, 55g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g less than 350g ai / ha, such as less than 22g ai / ha; or 20~350g ai / ha, 55~170g ai / ha, 22~220g ai / ha, 70~260g ai / ha, 30~250g ai / ha, 45~220g ai / ha, 80~200g ai / ha, 130~270g ai / ha, 150~330g applied to vegetation or areas adjacent to vegetation or to soil or water to inhibit the emergence or growth of vegetation in an amount ranging from any of the minimum values listed above to any of the maximum values listed above, such as 60-160g ai / ha, 180-345g ai / ha, 210-310g ai / ha, 90-190g ai / ha, or 22-340g ai / ha;

[0264] Piriminovac The compositions and methods of the present disclosure may include pyriminobac or an agriculturally acceptable salt or ester thereof. Pyriminobac, shown below, is a pyrimidinyloxybenzoate that provides post-emergence control of Echinochloa spp. in water-logged rice. Pyriminobac and methods for preparing pyriminobac are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0265] Pyriminobac may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, PiriminoBac is administered at an amount of 20g ai / ha or more, such as at least 22g ai / ha, at least 25g ai / ha, at least 30g ai / ha, at least 35g ai / ha, at least 40g ai / ha, at least 45g ai / ha, at least 50g ai / ha, at least 60g ai / ha, at least 70g ai / ha, at least 80g ai / ha, at least 90g ai / ha, at least 100g ai / ha, at least 120g ai / ha, at least 130g ai / ha, at least 140g ai / ha, at least 150g ai / ha, at least 160g ai / ha, or at least 170g ai / ha; at most 170g ai / ha, at most 160g ai / ha, at most 150g ai / ha, at most 140g ai / ha, at most 130g ai / ha, at most 120g ai / ha, ai / ha or less, 110g ai / ha or less, 100g ai / ha or less, 90g ai / ha or less, 80g ai / ha or less, 70g ai / ha or less, 60g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g less than 175g ai / ha, such as less than 22g ai / ha; or 20~175g ai / ha, 22~170g ai / ha, 35~120g ai / ha, 100~160g ai / ha, 40~150g ai / ha, 80~120g ai / ha, 25~110g ai / ha, 90~150g ai / ha, 45~130g It is applied to vegetation or areas adjacent to vegetation or to the soil or water to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values listed above to any of the maximum values listed above, such as 100g ai / ha, 60-160g ai / ha, 30-120g ai / ha, 20-160g ai / ha, or 22-100g ai / ha.

[0266] Sulfonylaminocarbonyltriazolinone herbicides In some embodiments, the compositions contain a herbicidally effective amount of a compound according to Formula I, and (b) flucarbazone, propoxycarbazone, thiecarbazone, or agriculturally acceptable salts or esters thereof, or combinations thereof.

[0267] Flucarbazone The compositions and methods of the present disclosure may include flucarbazone or an agriculturally acceptable salt or ester thereof. Flucarbazone, shown below, is a sulfonylamino-carbonyltriazolinone that provides post-emergence control of annual grass weeds and some perennial grass weeds and some broadleaf weeds. Flucarbazone and methods for preparing flucarbazone are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0268] Full carbazone can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to the vegetation or to soil or water in order to prevent the germination or growth of the vegetation. In some embodiments, full carbazone is at least 3.75 g ai / ha, such as at least 4 g ai / ha, at least 4.25 g ai / ha, at least 4.5 g ai / ha, at least 4.75 g ai / ha, at least 5 g ai / ha, at least 5.25 g ai / ha, at least 5.5 g ai / ha, at least 5.75 g ai / ha, at least 6 g ai / ha, at least 7 g ai / ha, at least 7.5 g ai / ha, at least 8 g ai / ha, at least 9 g ai / ha, at least 10 g ai / ha, at least 11 g ai / ha, at least 12 g ai / ha, at least 13 g ai / ha, at least 14 g ai / ha, at least 15 g ai / ha, at least 16 g ai / ha, at least 17 g ai / ha, at least 18 g ai / ha, at least 19 g ai / ha, at least 20 g ai / ha, at least 21 g ai / ha, at least 22 g ai / ha, at least 23 g ai / ha, at least 24 g ai / ha, at least 25 g ai / ha, at least 25.5 g ai / ha, at least 26 g ai / ha, at least 26.5 g ai / ha, at least 27 g ai / ha, at least 27.5 g ai / ha, at least 28 g ai / ha, at least 28.5 g ai / ha, at least 29 g ai / ha, at least 29.25 g ai / ha, at least 29.5 g ai / ha, or at least 29.75 g ai / ha; and up to 29.75 g ai / ha, up to 29.5 g ai / ha, up to 29.25 g ai / ha, up to 29 g ai / ha, up to 28.5 g ai / ha, up to 28 g ai / ha, up to 27.5 g ai / ha, up to 27 g ai / ha, up to 26.5 g ai / ha, up to 26 g ai / ha, up to 25 g ai / ha, up to 24 g ai / ha, up to 23 g ai / ha, up to 22 g ai / ha, up to 21 g ai / ha, up to 20 g ai / ha, up to 19 g ai / ha, up to 18 g ai / ha, up to 17 g ai / ha, up to 16 g ai / ha, up to 15 g ai / ha, up to 14 g ai / ha, up to 13 g ai / ha, up to 12 g ai / ha, up to 11 g ai / ha, up to 10 g ai / ha, up to 9 g ai / ha, up to 8 g ai / ha, up to 7.5 g ai / ha, up to 7 g ai / ha, up to 6 g ai / ha, up to 5.Amounts below 30g ai / ha, such as below 75g ai / ha, below 5.5g ai / ha, below 5.25g ai / ha, below 5g ai / ha, below 4.75g ai / ha, below 4.5g ai / ha, below 4.25g ai / ha, or below 4g ai / ha; or between 3.75 and 30g ai / ha, between 3.75 and 27g ai / ha, 4~28g ai / ha, 4~20g ai / ha, 5~29.5g ai / ha, 5~21g ai / ha, 5.5~28g ai / ha, 6~26g ai / ha, 7~25g ai / ha, 7.5~30g ai / ha, 7.5~21g ai / ha, 8~25g ai / ha, 9~19g ai / ha or 10~28.5g It is applied to vegetation or areas adjacent to vegetation, or to soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values above, such as ai / ha, to one of the maximum values above.

[0269] Propoxycarbazone The compositions and methods of the present disclosure may include propoxycarbazone or an agriculturally acceptable salt or ester thereof. Propoxycarbazone, shown below, is a sulfonylaminocarbonyltriazolinone that provides post-emergence control of grass weeds and some broadleaf weeds. Propoxycarbazone and methods for preparing propoxycarbazone are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0270] Propoxycarbazone may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, the propoxycarbazone is at least 4g ai / ha, at least 4.25g ai / ha, at least 4.5g ai / ha, at least 4.75g ai / ha, at least 5g ai / ha, at least 6g ai / ha, at least 7g ai / ha, at least 8g ai / ha, at least 9g ai / ha, at least 10g ai / ha, at least 12g ai / ha, at least 14g ai / ha ai / ha or more, 16g ai / ha or more, 18g ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 61g ai / ha or more, 62g ai / ha or more, 63g ai / ha or more, 64g 3. such as 65g ai / ha or more, 66g ai / ha or more, 67g ai / ha or more, 68g ai / ha or more, or 69g ai / ha or more.75g ai / ha or more; 69g ai / ha or less, 68g ai / ha or less, 67g ai / ha or less, 66g ai / ha or less, 65g ai / ha or less, 64g ai / ha or less, 63g ai / ha or less, 62g ai / ha or less, 61g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g less than ai / ha, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 28g ai / ha or less, 16g ai / ha or less, 14g ai / ha or less, 12g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g 70g ai / ha or less, such as less than 5g ai / ha, less than 5g ai / ha, less than 4.75g ai / ha, less than 4.5g ai / ha, less than 4.25g ai / ha, or less than 4g ai / ha; or 3.75-70g ai / ha, 4-68g ai / ha, 4.25-56g ai / ha, 4.5-28g ai / ha, 5~62g ai / ha, 5~38g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from one of the minimum values listed above to one of the maximum values listed above, such as 7-70g ai / ha, 8-52g ai / ha, 9-40g ai / ha, 10-70g ai / ha, 10-24g ai / ha, 12-69g ai / ha, 14-65g ai / ha, or 20-58g ai / ha.

[0271] Thiencarbazone The compositions and methods of the present disclosure may include thiencarbazone or an agriculturally acceptable salt or ester thereof. Thiencarbazone-methyl, shown below, is a sulfonylaminocarbonyltriazolinone that provides post-emergence control of grass weeds and some broadleaf weeds. Thiencarbazone and methods for preparing thiencarbazone are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0272] Thiencarbazon can be applied in an amount sufficient to induce a herbicidal effect in vegetation or in an area adjacent to the vegetation or in soil or water to prevent the germination or growth of vegetation. In some embodiments, thiencarbazon is applied in an amount of 2.5 g ai / ha or more, such as 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, 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, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 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, or 44 g ai / ha or more; 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, 28 g ai / ha or less, 26 g ai / ha or less, 24 g ai / ha or less, 22 g ai / ha or less, 20 g ai / ha or less, 18 g ai / ha or less, 16 g ai / ha or less, 14 g ai / ha or less, 12 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, 4.75 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, 3.45g ai / ha or less, such as 75g ai / ha or less, 3.5g ai / ha or less, 3.25g ai / ha or less, 3g ai / ha or 2.75g ai / ha; or 2.5-45g ai / ha, 2.5-41g ai / ha, 2.75-39g ai / ha, 2.75-37g ai / ha, 3~40g ai / ha, 3~33g ai / ha, 3.25~28g ai / ha, 3.5~45g ai / ha, 3.75~45g ai / ha, 4~39g ai / ha, 4.5~31g ai / ha, 5~45g ai / ha, 5~37g ai / ha, or 8~36g It is applied to vegetation or areas adjacent to vegetation, or to soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values above, such as ai / ha, to one of the maximum values above.

[0273] sulfonylurea herbicides In some embodiments, the composition comprises a herbicidally effective amount of a compound according to Formula I, and (b) amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron, metasulfuron, methas ... Contains zosulfuron, metsulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, propyrisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, triasulfuron, tribenuron, thifensulfuron, trifloxysulfuron, triflusulfuron, tritosulfuron, or an agriculturally acceptable salt or ester thereof, or a combination thereof.

[0274] Amidosulfuron The compositions and methods of the present disclosure may include amidosulfuron or an agriculturally acceptable salt or ester thereof. Amidosulfuron, shown below, is a sulfonylurea that provides post-emergence control of a wide range of broadleaf weeds, such as cleaver, in winter wheat, durum wheat, barley, rye, triticale, and oats. [ka] Methods for preparing amidosulfuron are known in the art, and its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.

[0275] Amidosulfuron may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, the amidosulfuron is 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, 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, 13g ai / ha or more, 14g ai / ha or more, 15g ai / ha or more, 16g ai / ha or more, 17g ai / ha or more, 18g ai / ha or more, 19g ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 51g ai / ha or more, 52g ai / ha or more, 53g ai / ha or more, 54g ai / ha or more, 55g 3. such as 56g ai / ha or more, 57g ai / ha or more, 58g ai / ha or more, or 59g ai / ha or more.75g ai / ha or more; 59g ai / ha or less, 58g ai / ha or less, 57g ai / ha or less, 56g ai / ha or less, 55g ai / ha or less, 54g ai / ha or less, 53g ai / ha or less, 52g ai / ha or less, 51g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g less than 44g ai / ha, less than 42g ai / ha, less than 40g ai / ha, less than 38g ai / ha, less than 36g ai / ha, less than 34g ai / ha, less than 32g ai / ha, less than 30g ai / ha, less than 28g ai / ha, less than 26g ai / ha, less than 24g ai / ha, less than 22g ai / ha, 20g less than ai / ha, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g 60g ai / ha or less, such as 5g ai / ha or less, 4.75g ai / ha or less, 4.5g ai / ha, or 4.25g ai / ha, or 4g ai / ha or less; or 3.75-60g ai / ha, 4-58g ai / ha, 4.5-51g ai / ha, 5-57g ai / ha, 5~30g ai / ha, 6~42g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation in an amount ranging from one of the minimum values listed above to one of the maximum values listed above, such as 1000 g ai / ha, 8-50 g ai / ha, 9-32 g ai / ha, 10-53 g ai / ha, 12-30 g ai / ha, or 13-40 g ai / ha.

[0276] Azimsulfuron The compositions and methods of the present disclosure may include azimsulfuron or an agriculturally acceptable salt or ester thereof. Azimsulfuron, shown below, is a sulfonylurea that provides post-emergence control of annual and perennial broadleaf and sedge weeds, for example, in rice. Azimsulfuron and methods for preparing azimsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0277] Azimsulfuron can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to vegetation or to soil or water in order to prevent the germination or growth of vegetation. In some embodiments, azimsulfuron is an amount of 3.125 g ai / ha or more, such as 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, 5.5 g ai / ha or more, 6 g ai / ha or more, 6.5 g ai / ha or more, 7 g ai / ha or more, 7.5 g 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 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, 20.5 g ai / ha or more, 21 g ai / ha or more, 21.5 g ai / ha or more, 22 g ai / ha or more, 22.5 g ai / ha or more, 22.75 g ai / ha or more, 23 g ai / ha or more, 23.25 g ai / ha or more, 23.5 g ai / ha or more, 23.75 g ai / ha or more, 24 g ai / ha or more, 24.25 g ai / ha or more, 24.5 g ai / ha or more, or 24.75 g ai / ha or more; 24.75 g ai / ha or less, 24.5 g ai / ha or less, 24.25 g ai / ha or less, 24 g ai / ha or less, 23.75 g ai / ha or less, 23.5 g ai / ha or less, 23.25 g ai / ha or less, 23 g ai / ha or less, 22.75 g ai / ha or less, 22.5 g ai / ha or less, 22 g ai / ha or less, 21.5 g ai / ha or less, 21 g ai / ha or less, 20.5 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 g 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, 9.5g ai / ha or less, 9g ai / ha or less, 8.5g ai / ha or less, 8g ai / ha or less, 7.5g ai / ha or less, 7g ai / ha or less, 6.5g ai / ha or less, 6g ai / ha or less, 5.5g ai / ha or less, 5g ai / ha or less, 4.75g ai / ha or less, 4.5g ai / ha or less, 4.25g 25g ai / ha or less, such as less than or equal to 4g ai / ha, less than or equal to 3.75g ai / ha, less than or equal to 3.5g ai / ha, or less than or equal to 3.25g ai / ha; ai / ha, 3.5~24.5g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from one of the minimum values listed above to one of the maximum values listed above, such as 3.5-19g ai / ha, 3.75-22g ai / ha, 4-25g ai / ha, 4-23.25g ai / ha, 4.25-20g ai / ha, 4.5-18g ai / ha, 4.75-22.75g ai / ha, or 5-24g ai / ha.

[0278] Bensulfuron The compositions and methods of the present disclosure may include bensulfuron or its agriculturally acceptable salts or esters. Bensulfuron-methyl, shown below, is a sulfonylurea that provides pre- and post-emergence control of annual and perennial broadleaf weeds and sedges, for example, in rice. Bensulfuron and methods for preparing bensulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0279] Bensulfuron may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, bensulfuron is 9g ai / ha or more, 10g ai / ha or more, 11g ai / ha or more, 12g ai / ha or more, 13g ai / ha or more, 14g ai / ha or more, 15g ai / ha or more, 16g ai / ha or more, 17g ai / ha or more, 18g ai / ha or more, 19g ai / ha or more, 20g ai / ha or more ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, or 69g ai / ha or more.75g ai / ha or more; 69g ai / ha or less, 68g ai / ha or less, 66g ai / ha or less, 64g ai / ha or less, 62g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g less than 46g ai / ha, less than 44g ai / ha, less than 42g ai / ha, less than 40g ai / ha, less than 38g ai / ha, less than 36g ai / ha, less than 34g ai / ha, less than 32g ai / ha, less than 30g ai / ha, less than 28g ai / ha, less than 26g ai / ha, less than 24g ai / ha, 22g less than ai / ha, 20g 70g such as less than 19g ai / ha, less than 18g ai / ha, less than 17g ai / ha, less than 16g ai / ha, less than 15g ai / ha, less than 14g ai / ha, less than 13g ai / ha, less than 12g ai / ha, less than 11g ai / ha, less than 10g ai / ha, or less than 9g ai / ha ai / ha or less; or 8.75-70g ai / ha, 9-60g ai / ha, 10-65g ai / ha, 10-40g ai / ha, 10-28g ai / ha, 11-68g ai / ha, 11-54g ai / ha, 12-60g ai / ha, 12-42g ai / ha, 13-69g ai / ha, 14~56g ai / ha, 15~40g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values listed above, such as 20-46 g ai / ha, or 20-69 g ai / ha, to one of the maximum values listed above.

[0280] Chlorsulfuron The compositions and methods of the present disclosure may include chlorsulfuron or its agriculturally acceptable salts or esters. Chlorsulfuron, shown below, is a sulfonylurea that provides broadleaf weed and annual grass control in, for example, wheat, barley, oats, rye, triticale, and flax, and on non-crop land. Chlorsulfuron and methods for preparing chlorsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0281] Chlorsulfuron may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, the chlorsulfuron is 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, 3.75g ai / ha or more, 4g ai / ha or more, 4.25g ai / ha or more, 4.5g ai / ha or more, 4.75g ai / ha or more, 5g ai / ha or more, 6g ai / ha or more, 7g ai / ha or more, 8g ai / ha or more, 9g ai / ha or more, 10g ai / ha or more, 11g ai / ha or more, 12g ai / ha or more, 13g ai / ha or more, 14g ai / ha or more, 15g ai / ha or more, 16g ai / ha or more, 17g ai / ha or more, 18g ai / ha or more, 19g ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 47g ai / ha or more, 48g ai / ha or more, 49g ai / ha or more, 50g ai / ha or more, 51g ai / ha or more, or 51.5g 1.1g such as ai / ha or more ai / ha or more;51.An amount of 52 g ai / ha or less, such as 5 g ai / ha or less, 51 g ai / ha or less, 50 g ai / ha or less, 49 g ai / ha or less, 48 g ai / ha or less, 47 g ai / ha or less, 46 g ai / ha or less, 44 g ai / ha or less, 42 g ai / ha or less, 40 g ai / ha or less, 38 g ai / ha or less, 36 g ai / ha or less, 34 g ai / ha or less, 32 g ai / ha or less, 30 g ai / ha or less, 28 g ai / ha or less, 26 g ai / ha or less, 24 g ai / ha or less, 22 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 g 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, 4.75 g ai / ha or less, 4.5 g ai / ha or less, or 4.25 g ai / ha or less; or an amount in the range from any of the above minimum values to any of the above maximum values, such as 1.1 - 52 g ai / ha, 1.25 - 51.5 g ai / ha, 1.5 - 30 g ai / ha, 1.75 - 47 g ai / ha, 2 - 26 g ai / ha, 3 - 50 g ai / ha, 4 - 38 g ai / ha, 4.5 - 42 g ai / ha, 5 - 51 g ai / ha, 7 - 49 g ai / ha, 9 - 32 g ai / ha, 10 - 45 g ai / ha, 12 - 52 g ai / ha, or 15 - 48 g ai / ha, is applied to vegetation or an area adjacent to the vegetation or to soil or water to prevent the germination or growth of the vegetation.

[0282] Ethoxysulfuron The compositions and methods of the present disclosure may include ethoxysulfuron or its agriculturally acceptable salts or esters. Ethoxysulfuron, shown below, is a sulfonylurea that provides broadleaf and sedge weed control in, for example, cereals, rice, and sugarcane. Ethoxysulfuron and methods for preparing ethoxysulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0283] Ethoxysulfuron may be applied to vegetation or areas adjacent to vegetation, or to the soil or water to prevent the emergence or growth of vegetation, in an amount sufficient to induce a herbicidal effect. In some embodiments, the ethoxysulfuron is at least 6 g ai / ha, at least 7 g ai / ha, at least 8 g ai / ha, at least 9 g ai / ha, at least 10 g ai / ha, at least 11 g ai / ha, at least 12 g ai / ha, at least 13 g ai / ha, at least 14 g ai / ha, at least 15 g ai / ha, at least 16 g ai / ha, at least 17 g ai / ha ai / ha or more, 18g ai / ha or more, 19g ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 55g ai / ha or more, 60g ai / ha or more, 65g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 85g ai / ha or more, 90g ai / ha or more, 95g ai / ha or more, 100g ai / ha or more, 101g ai / ha or more, 102g ai / ha or more, 103g ai / ha or more, 104g ai / ha or more, 105g ai / ha or more, 106g ai / ha or more, 107g ai / ha or more, 108g ai / ha or more, 109g ai / ha or more, 110g ai / ha or more, 111g ai / ha or more, 112g ai / ha or more, 113g ai / ha or more, 114g ai / ha or more, 115g amounts of 5g ai / ha or more, such as 116g ai / ha or more, 117g ai / ha or more, 118g ai / ha or more, or 119g ai / ha or more;An amount of 120 g ai / ha or less, such as 119 g ai / ha or less, 118 g ai / ha or less, 117 g ai / ha or less, 116 g ai / ha or less, 115 g ai / ha or less, 114 g ai / ha or less, 113 g ai / ha or less, 112 g ai / ha or less, 111 g ai / ha or less, 110 g ai / ha or less, 109 g ai / ha or less, 108 g ai / ha or less, 107 g ai / ha or less, 106 g ai / ha or less, 105 g ai / ha or less, 104 g ai / ha or less, 103 g ai / ha or less, 102 g ai / ha or less, 101 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, 38 g ai / ha or less, 36 g ai / ha or less, 34 g ai / ha or less, 32 g ai / ha or less, 30 g ai / ha or less, 28 g ai / ha or less, 26 g ai / ha or less, 24 g ai / ha or less, 22 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 g 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, or 6 g ai / ha or less; or an amount in the range from any of the above minimum values to any of the above maximum values, such as 5 - 120 g ai / ha, 5 - 90 g ai / ha, 5 - 75 g ai / ha, 6 - 114 g ai / ha, 8 - 108 g ai / ha, 9 - 113 g ai / ha, 10 - 80 g ai / ha, 10 - 55 g ai / ha, 12 - 112 g ai / ha, 13 - 85 g ai / ha, 15 - 106 g ai / ha, 20 - 100 g ai / ha, 24 - 105 g ai / ha, or 28 - 115 g ai / ha, is applied to vegetation or an area adjacent to the vegetation or to soil or water in order to prevent the germination or growth of the vegetation.;

[0284] Flupyrsulfuron The compositions and methods of the present disclosure may include flupyrsulfuron or an agriculturally acceptable salt or ester thereof. Flupyrsulfuron-methyl sodium, shown below, is a sulfonylurea used, for example, for post-emergence control of grass and broadleaf weeds in cereals. [ka] Flupyrsulfuron and methods for preparing flupyrsulfuron are known in the art, and its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.

[0285] Full pyrithiobac can be applied in an amount sufficient to induce a herbicidal effect in vegetation or an area adjacent to the vegetation, or in soil or water, to prevent the germination or growth of the vegetation. In some embodiments, the full pyrithiobac is in an amount of 2.5 g ai / ha or more, such as 2.6 g ai / ha or more, 2.7 g ai / ha or more, 2.8 g ai / ha or more, 2.9 g ai / ha or more, 3.0 g ai / ha or more, 3.2 g ai / ha or more, 3.4 g ai / ha or more, 3.6 g ai / ha or more, 3.8 g ai / ha or more, 4 g ai / ha or more, 4.2 g ai / ha or more, 4.4 g ai / ha or more, 4.6 g ai / ha or more, 4.8 g ai / ha or more, 5 g ai / ha or more, 5.2 g ai / ha or more, 5.4 g ai / ha or more, 5.6 g ai / ha or more, 5.8 g ai / ha or more, 6 g ai / ha or more, 6.2 g ai / ha or more, 6.4 g ai / ha or more, 6.6 g ai / ha or more, 6.8 g ai / ha or more, 7 g ai / ha or more, 7.2 ai / ha or more, 7.4 g ai / ha or more, 7.6 g ai / ha or more, 8 g ai / ha or more, 8.2 g ai / ha or more, 8.4 ai / ha or more, 8.6 g ai / ha or more, 8.8 g ai / ha or more, 9 g ai / ha or more, 9.1 g ai / ha or more, 9.2 g ai / ha or more, 9.3 g ai / ha or more, 9.4 g ai / ha or more, 9.5 g ai / ha or more, 9.6 g ai / ha or more, 9.7 g ai / ha or more, 9.8 g ai / ha or more, or 9.9 g ai / ha or more; 9.9 g ai / ha or less, 9.8 g ai / ha or less, 9.7 g ai / ha or less, 9.6 g ai / ha or less, 9.5 g ai / ha or less, 9.4 g ai / ha or less, 9.3 g ai / ha or less, 9.2 g ai / ha or less, 9.1 g ai / ha or less, 9 g ai / ha or less, 8.8 g ai / ha or less, 8.6 g ai / ha or less, 8.4 g ai / ha or less, 8.2 g ai / ha or less, 8 g ai / ha or less, 7.8 g ai / ha or less, 7.6 g ai / ha or less, 7.4 g ai / ha or less, 7.2 g ai / ha or less, 7 g ai / ha or less, 6.8 g ai / ha or less, 6.6 g ai / ha or less, 6.4 g ai / ha or less, 6.2 g ai / ha or less, 6 g ai / ha or less, 5.8 g ai / ha or less, 5.6g ai / ha or less, 5.4g ai / ha or less, 5.2g ai / ha or less, 5g ai / ha or less, 4.8g ai / ha or less, 4.6g ai / ha or less, 4.4g ai / ha or less, 4.2g ai / ha or less, 4g ai / ha or less, 3.8g ai / ha or less, 3.6g ai / ha or less, 3.4g Amounts below 10g ai / ha, such as below 3.2g ai / ha, below 3g ai / ha, below 2.9g ai / ha, below 2.8g ai / ha, below 2.7g ai / ha, or below 2.6g ai / ha; or between 2.5 and 10g ai / ha, between 2.5 and 9.4g ai / ha, between 2.6 and 9g ai / ha, 2.7~10g ai / ha, 2.8~9.4g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from one of the minimum values listed above to one of the maximum values listed above, such as 0.01 ai / ha, 3-8.8g ai / ha, 3.2-7.2g ai / ha, 3.4-8.6g ai / ha, 3.6-10g ai / ha, 3.8-9.5g ai / ha, 4-8.8g ai / ha, 4.4-7g ai / ha, 4.6-6.8g ai / ha, or 5-9.5g ai / ha.

[0286] Foramsulfuron The compositions and methods of the present disclosure may include foramsulfuron or an agriculturally acceptable salt or ester thereof. Foramsulfuron, shown below, is a sulfonylurea that provides post-emergence control of grass and broadleaf weeds in corn, for example. Foramsulfuron and methods for preparing foramsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0287] Foramsulfuron may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, foramsulfuron is 22.5 g ai / ha or more, such as at least 23 g ai / ha, at least 24 g ai / ha, at least 25 g ai / ha, at least 26 g ai / ha, at least 28 g ai / ha, at least 30 g ai / ha, at least 32 g ai / ha, at least 34 g ai / ha, at least 35 g ai / ha, at least 36 g ai / ha, at least 38 g ai / ha, at least 40 g ai / ha, at least 42 g ai / ha, at least 44 g ai / ha, at least 46 g ai / ha, at least 48 g ai / ha, at least 50 g ai / ha, at least 51 g ai / ha, at least 52 g ai / ha, at least 53 g ai / ha, at least 54 g ai / ha, at least 55 g ai / ha, at least 56 g ai / ha, at least 57 g ai / ha, or at least 58 g ai / ha. Amount above ai / ha; 58g ai / ha or less, 57g ai / ha or less, 56g ai / ha or less, 55g ai / ha or less, 54g ai / ha or less, 53g ai / ha or less, 52g ai / ha or less, 51g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g less than 34g ai / ha, less than 32g ai / ha, less than 30g ai / ha, less than 28g ai / ha, less than 26g ai / ha, less than 25g ai / ha, less than 24g ai / ha, or less than 23g 59g such as less than ai / ha ai / ha or less; or applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from any of the above minimums to any of the above maximums, such as 22.5 to 59 g ai / ha, 23 to 51 g ai / ha, 25 to 38 g ai / ha, 26 to 57 g ai / ha, 28 to 48 g ai / ha, 30 to 58 g ai / ha, 30 to 50 g ai / ha, 32 to 55 g ai / ha, 34 to 57 g ai / ha, or 35 to 58 g ai / ha.

[0288] Halosulfuron The compositions and methods of the present disclosure may include halosulfuron or its agriculturally acceptable salt or ester. Halosulfuron-methyl, shown below, is a sulfonylurea that has demonstrated activity for controlling annual broadleaf weeds and nutsedge species in corn, sugarcane, rice, sorghum, nut crops, and turf. Halosulfuron and methods for preparing halosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0289] Halosulfuron may be applied to vegetation or areas adjacent to vegetation, or to the soil or water to prevent the emergence or growth of vegetation, in an amount sufficient to induce a herbicidal effect. In some embodiments, the halosulfuron is 4.75 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, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 55g ai / ha or more, 60g ai / ha or more, 65g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 85g ai / ha or more, 90g ai / ha or more, 95g ai / ha or more, 100g ai / ha or more, 105g ai / ha or more, 110g ai / ha or more, 115g ai / ha or more, 120g ai / ha or more, 122g ai / ha or more, 124g ai / ha or more, 126g ai / ha or more, 128g ai / ha or more, 130g ai / ha or more, 131g ai / ha or more, 132g ai / ha or more, 133g 4. such as 134g ai / ha or more, 135g ai / ha or more, 136g ai / ha or more, 137g ai / ha or more, 138g ai / ha or more, or 139g ai / ha or more.375g ai / ha or more; 138g ai / ha or less, 137g ai / ha or less, 136g ai / ha or less, 135g ai / ha or less, 134g ai / ha or less, 133g ai / ha or less, 132g ai / ha or less, 131g ai / ha or less, 130g ai / ha or less, 129g ai / ha or less, 128g ai / ha or less, 126g ai / ha or less, 124g ai / ha or less, 122g ai / ha or less, 120g ai / ha or less, 115g ai / ha or less, 110g ai / ha or less, 105g ai / ha or less, 100g ai / ha or less, 95g ai / ha or less, 90g ai / ha or less, 85g ai / ha or less, 80g less than ai / ha, 75g less than 70g ai / ha, less than 65g ai / ha, less than 60g ai / ha, less than 55g ai / ha, less than 50g ai / ha, less than 45g ai / ha, less than 40g ai / ha, less than 35g ai / ha, less than 30g ai / ha, less than 25g ai / ha, less than 20g ai / ha, less than 15g ai / ha, 10g An amount of 139g ai / ha or less, such as 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4.75g ai / ha or less, or 4.5g ai / ha or less; or 4.375~140g ai / ha, 4.5~120g ai / ha, 4.75~100g ai / ha, 5~95g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from one of the minimum values above to one of the maximum values above, such as 0.01 ai / ha, 5-131g ai / ha, 6-80g ai / ha, 7-130g ai / ha, 8-122g ai / ha, 9-75g ai / ha, 10-139g ai / ha, 15-90g ai / ha, 20-124g ai / ha, 25-110g ai / ha, or 25-75g ai / ha.

[0290] Iodosulfuron The compositions and methods of the present disclosure may include iodosulfuron or its agriculturally acceptable salts or esters. Iodosulfuron-methyl-sodium, shown below, is a sulfonylurea that provides post-emergence control of grass and broadleaf weeds in, for example, winter, spring, and durum wheat, triticale, rye, and spring barley. Iodosulfuron and methods for preparing iodosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0291] Iodosulfuron can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to the vegetation or to soil or water in order to prevent the emergence or growth of the vegetation. In some embodiments, iodosulfuron is at least 0.2 g ai / ha, at least 0.3 g ai / ha, at least 0.4 g ai / ha, at least 0.5 g ai / ha, at least 0.6 g ai / ha, at least 0.7 g ai / ha, at least 0.8 g ai / ha, at least 0.9 g ai / ha, at least 1 g ai / ha, at least 1.1 g ai / ha, at least 1.2 g ai / ha, at least 1.3 g ai / ha, at least 1.4 g ai / ha, at least 1.5 g ai / ha, at least 1.6 g ai / ha, at least 1.7 g ai / ha, at least 1.8 g ai / ha, at least 1.9 g ai / ha, at least 2.0 g ai / ha, at least 2.1 g ai / ha, at least 2.2 g ai / ha, at least 2.3 g ai / ha, at least 2.3 g ai / ha, at least 2.4 g ai / ha, at least 2.5 g ai / ha, at least 2.6 g ai / ha, at least 2.7 g ai / ha, at least 2.8 g ai / ha, at least 2.9 g ai / ha, at least 3.0 g ai / ha, at least 3.2 g ai / ha, at least 3.4 g ai / ha, at least 3.6 g ai / ha, at least 3.8 g ai / ha, at least 4 g ai / ha, at least 4.2 g ai / ha, at least 4.4 g ai / ha, at least 4.6 g ai / ha, at least 4.8 g ai / ha, at least 5 g ai / ha, at least 5.2 g ai / ha, at least 5.4 g ai / ha, at least 5.6 g ai / ha, at least 5.8 g ai / ha, at least 6 g ai / ha, at least 6.2 g ai / ha, at least 6.4 g ai / ha, at least 6.6 g ai / ha, at least 6.8 g ai / ha, at least 7 g ai / ha, at least 7.2 ai / ha, at least 7.4 g ai / ha, at least 7.6 g ai / ha, at least 8 g ai / ha, at least 8.2 g ai / ha, at least 8.4 ai / ha, at least 8.6 g ai / ha, at least 8.8 g ai / ha, at least 9 g ai / ha, at least 9.1 g ai / ha, at least 9.2 g ai / ha, at least 9.3 g ai / ha, at least 9.4 g ai / ha, at least 9.5 g ai / ha, at least 9.6 g ai / ha, at least 9.7 g ai / ha, at least 9.8 g ai / ha, or at least 9.9 g ai / ha, i.e., an amount of at least 0.1 g ai / ha; up to 9.9 g ai / ha, 9.An amount of 10 g ai / ha or less, such as 8 g ai / ha or less, 9.7 g ai / ha or less, 9.6 g ai / ha or less, 9.5 g ai / ha or less, 9.4 g ai / ha or less, 9.3 g ai / ha or less, 9.2 g ai / ha or less, 9.1 g ai / ha or less, 9 g ai / ha or less, 8.8 g ai / ha or less, 8.6 g ai / ha or less, 8.4 g ai / ha or less, 8.2 g ai / ha or less, 8 g ai / ha or less, 7.8 g ai / ha or less, 7.6 g ai / ha or less, 7.4 g ai / ha or less, 7.2 g ai / ha or less, 7 g ai / ha or less, 6.8 g ai / ha or less, 6.6 g ai / ha or less, 6.4 g ai / ha or less, 6.2 g ai / ha or less, 6 g ai / ha or less, 5.8 g ai / ha or less, 5.6 g ai / ha or less, 5.4 g ai / ha or less, 5.2 g ai / ha or less, 5 g ai / ha or less, 4.8 g ai / ha or less, 4.6 g ai / ha or less, 4.4 g ai / ha or less, 4.2 g ai / ha or less, 4 g ai / ha or less, 3.8 g ai / ha or less, 3.6 g ai / ha or less, 3.4 g ai / ha or less, 3.2 g ai / ha or less, 3 g ai / ha or less, 2.9 g ai / ha or less, 2.8 g ai / ha or less, 2.7 g ai / ha or less, 2.6 g ai / ha or less, 2.5 g ai / ha or less, 2.4 g ai / ha or less, 2.3 g ai / ha or less, 2.2 g ai / ha or less, 2.1 g ai / ha or less, 2.0 g ai / ha or less, 1.9 g ai / ha or less, 1.8 g ai / ha or less, 1.7 g ai / ha or less, 1.6 g ai / ha or less, 1.5 g ai / ha or less, 1.4 g ai / ha or less, 1.3 g ai / ha or less, 1.2 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, or 0.2 g ai / ha or less; or 0.1 - 10 g ai / ha, 0.4 - 8.8 g ai / ha, 1.1 - 6.2 g ai / ha, 1.7 - 7.5 g ai / ha, 1.8 - 9.2 g ai / ha, 1.9 - 9 g ai / ha, 2 - 6.8 g ai / ha, 2.2 - 9.5 g ai / ha, 2.It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation at a rate ranging from one of the minimum values listed above to one of the maximum values listed above, such as 5-10 g ai / ha, 2.8-7.6 g ai / ha, 3-9.4 g ai / ha, 3.2-7.2 g ai / ha, 3.4-10 g ai / ha, or 3.6-8 g ai / ha.

[0292] Mesosulfuron The compositions and methods of the present disclosure can include mesosulfuron or its agriculturally acceptable salts or esters. Mesosulfuron-methyl, shown below, is a sulfonylurea that provides early-to-mid-emergence control of grasses and some broadleaf weeds in, for example, winter, spring, and durum wheat, triticale, and rye. Mesosulfuron and methods for preparing mesosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0293] Mesosulfuron may be applied to vegetation or areas adjacent to vegetation, or to the soil or water to prevent the emergence or growth of vegetation, in an amount sufficient to induce a herbicidal effect. In some embodiments, the mesosulfuron is 1.6 g ai / ha or more, 1.7 g ai / ha or more, 1.8 g ai / ha or more, 1.9 g ai / ha or more, 2 g ai / ha or more, 2.1 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, 3.25g ai / ha or more, 3.5g ai / ha or more, 3.75g ai / ha or more, 4g ai / ha or more, 4.25g ai / ha or more, 4.5g ai / ha or more, 4.75g ai / ha or more, 5g ai / ha or more, 6g ai / ha or more, 7g ai / ha or more, 8g ai / ha or more, 9g ai / ha or more, 10g ai / ha or more, 12g ai / ha or more, 14g ai / ha or more, 16g ai / ha or more, 18g ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 31g ai / ha or more, 32g ai / ha or more, 33g ai / ha or more, 34g ai / ha or more, 35g ai / ha or more, 36g ai / ha or more, 37g ai / ha or more, 38g ai / ha or more, 39g ai / ha or more, 40g ai / ha or more, 41g ai / ha or more, 42g ai / ha or more, 43g ai / ha or more, or 44g ai / ha or more.An amount of 5 g ai / ha or more; amounts of 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, 28 g ai / ha or less, 26 g ai / ha or less, 24 g ai / ha or less, 22 g ai / ha or less, 20 g ai / ha or less, 18 g ai / ha or less, 16 g ai / ha or less, 14 g ai / ha or less, 12 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, 4.75 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, 2.1 g ai / ha or less, 2 g ai / ha or less, 1.9 g ai / ha or less, 1.8 g ai / ha or less, 1.7 g ai / ha or less, 1.6 g ai / ha or less, etc., i.e., amounts of 45 g ai / ha or less; or amounts in the range from any of the above minimum values to any of the above maximum values, such as 1.5 - 45 g ai / ha, 1.6 - 42 g ai / ha, 1.5 - 40 g ai / ha, 1.7 - 43 g ai / ha, 1.8 - 35 g ai / ha, 2 - 37 g ai / ha, 2.25 - 41 g ai / ha, 2.5 - 32 g ai / ha, 2.75 - 45 g ai / ha, 3 - 40 g ai / ha, 3 - 33 g ai / ha, 3 - 24 g ai / ha, 3.5 - 45 g ai / ha, or 4 - 39 g ai / ha, are applied to vegetation or an area adjacent to the vegetation or to the soil or water to prevent the germination or growth of the vegetation.

[0294] Metsulfuron The compositions and methods of the present disclosure may include metsulfuron or its agriculturally acceptable salts or esters. Metsulfuron-methyl, shown below, is a sulfonylurea that controls grass and broadleaf weeds in, for example, wheat, barley, rice, oats, and triticale. Metsulfuron and methods for preparing metsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0295] Metsulfuron can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to the vegetation or to soil or water in order to prevent the germination or growth of the vegetation. In some embodiments, the metsulfuron is at least 1.1 g ai / ha, at least 1.2 g ai / ha, at least 1.25 g ai / ha, at least 1.3 g ai / ha, at least 1.4 g ai / ha, at least 1.5 g ai / ha, at least 1.6 g ai / ha, at least 1.7 g ai / ha, at least 1.8 g ai / ha, at least 1.9 g ai / ha, at least 2 g ai / ha, at least 2.1 g ai / ha, at least 2.2 g ai / ha, at least 2.3 g ai / ha, at least 2.3 g ai / ha, at least 2.4 g ai / ha, at least 2.5 g ai / ha, at least 2.6 g ai / ha, at least 2.7 g ai / ha, at least 2.8 g ai / ha, at least 2.9 g ai / ha, at least 3 g ai / ha, at least 3.2 g ai / ha, at least 3.4 g ai / ha, at least 3.6 g ai / ha, at least 3.8 g ai / ha, at least 4 g ai / ha, at least 4.2 g ai / ha, at least 4.4 g ai / ha, at least 4.6 g ai / ha, at least 4.8 g ai / ha, at least 5 g ai / ha, at least 5.2 g ai / ha, at least 5.4 g ai / ha, at least 5.6 g ai / ha, at least 5.8 g ai / ha, at least 6 g ai / ha, at least 6.2 g ai / ha, at least 6.4 g ai / ha, at least 6.6 g ai / ha, at least 6.8 g ai / ha, at least 7 g ai / ha, at least 7.2 ai / ha, at least 7.4 g ai / ha, at least 7.6 g ai / ha, at least 7.8 g ai / ha, at least 8 g ai / ha, at least 8.2 g ai / ha, at least 8.4 ai / ha, at least 8.6 g ai / ha, at least 8.8 g ai / ha, at least 9 g ai / ha, at least 9.2 g ai / ha, at least 9.4 g ai / ha, at least 9.6 g ai / ha, at least 9.8 g ai / ha, at least 10 g ai / ha, at least 10.2 g ai / ha, at least 10.4 g ai / ha, at least 10.6 g ai / ha, at least 10.8 g ai / ha, at least 11 g ai / ha, at least 11.1 g ai / ha, at least 11.2 g ai / ha, at least 11.3 g ai / ha, at least 11.4 g ai / ha, at least 11.5 g ai / ha, at least 11.6 g ai / ha, at least 11.7 g ai / ha, at least 11.An amount of 1 g ai / ha or more, such as 8 g ai / ha or more, or 11.9 g ai / ha or more; 11.9 g ai / ha or less, 11.8 g ai / ha or less, 11.7 g ai / ha or less, 11.6 g ai / ha or less, 11.5 g ai / ha or less, 11.4 g ai / ha or less, 11.3 g ai / ha or less, 11.2 g ai / ha or less, 11.1 g ai / ha or less, 11 g ai / ha or less, 10.8 g ai / ha or less, 10.6 g ai / ha or less, 10.4 g ai / ha or less, 10.2 g ai / ha or less, 10 g ai / ha or less, 9.8 g ai / ha or less, 9.6 g ai / ha or less, 9.4 g ai / ha or less, 9.2 g ai / ha or less, 9 g ai / ha or less, 8.8 g ai / ha or less, 8.6 g ai / ha or less, 8.4 g ai / ha or less, 8.2 g ai / ha or less, 8 g ai / ha or less, 7.8 g ai / ha or less, 7.6 g ai / ha or less, 7.4 g ai / ha or less, 7.2 g ai / ha or less, 7 g ai / ha or less, 6.8 g ai / ha or less, 6.6 g ai / ha or less, 6.4 g ai / ha or less, 6.2 g ai / ha or less, 6 g ai / ha or less, 5.8 g ai / ha or less, 5.6 g ai / ha or less, 5.4 g ai / ha or less, 5.2 g ai / ha or less, 5 g ai / ha or less, 4.8 g ai / ha or less, 4.6 g ai / ha or less, 4.4 g ai / ha or less, 4.2 g ai / ha or less, 4 g ai / ha or less, 3.8 g ai / ha or less, 3.6 g ai / ha or less, 3.4 g ai / ha or less, 3.2 g ai / ha or less, 3 g ai / ha or less, 2.9 g ai / ha or less, 2.8 g ai / ha or less, 2.7 g ai / ha or less, 2.6 g ai / ha or less, 2.5 g ai / ha or less, 2.4 g ai / ha or less, 2.3 g ai / ha or less, 2.2 g ai / ha or less, 2.1 g ai / ha or less, 2 g ai / ha or less, 1.9 g ai / ha or less, 1.8 g ai / ha, 1.7 g ai / ha or less, 1.6 g ai / ha or less, 1.5 g ai / ha or less, 1.4 g ai / ha or less, 1.3 g ai / ha or less, 1.25 g ai / ha or less, 1.2 g ai / ha or less, or 1.1 g ai / ha or less, etc., an amount of 12 g ai / ha or less; or 1 - 12 g ai / ha, 1 - 10 g ai / ha, 1.1 - 9.It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent vegetation emergence or growth at a rate ranging from one of the minimums listed above to one of the maximums listed above, such as 4 g ai / ha, 1.25-8.2 g ai / ha, 1.25-11 g ai / ha, 1.3-7 g ai / ha, 1.4-5.8 g ai / ha, 1.5-12 g ai / ha, 1.5-10.4 g ai / ha, 1.5-8.8 g ai / ha, 2-11.7 g ai / ha, 2.2-6.4 g ai / ha, 2.5-7.6 g ai / ha, 2.8-12 g ai / ha, or 3-8 g ai / ha.

[0296] Nicosulfuron The compositions and methods of the present disclosure may contain nicosulfuron or its agriculturally acceptable salt or ester. Nicosulfuron, shown below, is a sulfonylurea that provides selective post-emergence control of annual grass weeds, including Setaria, Echinochloa, Digitaria, Panicum, Lolium, and Avena species, broadleaf weeds, including Amaranthus species and Cruciferae, and perennial plants, such as Sorghum halepense and Agropyron repens, in corn, for example. Nicosulfuron and methods for preparing nicosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0297] Nicosulfuron may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, nicosulfuron is 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, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, or 69g ai / ha or more.75g ai / ha or more; 69g ai / ha or less, 68g ai / ha or less, 66g ai / ha or less, 64g ai / ha or less, 62g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g less than ai / ha, 20g 70g such as less than 19g ai / ha, less than 18g ai / ha, less than 17g ai / ha, less than 16g ai / ha, less than 15g ai / ha, less than 14g ai / ha, less than 13g ai / ha, less than 12g ai / ha, less than 11g ai / ha, less than 10g ai / ha, or less than 9g ai / ha ai / ha or less; or 8.75-70g ai / ha, 9-68g ai / ha, 10-50g ai / ha, 12-66g ai / ha, 14-44g ai / ha, 15-58g ai / ha, 18-65g ai / ha, 20-45g ai / ha, 22-60g ai / ha, 26-56g ai / ha or 30~70g It is applied to vegetation or areas adjacent to vegetation, or to soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values above, such as ai / ha, to one of the maximum values above.

[0298] Orthosulfamuron The compositions and methods of the present disclosure may include orthosulfamuron or an agriculturally acceptable salt or ester thereof. Orthosulfamuron, shown below, is a sulfonylurea that provides early post-emergence control of annual and perennial broadleaf weeds and sedges in, for example, rice, cereals, pastures, and sugarcane. [ka] Methods for preparing orthosulfamuron are known in the art, and its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.

[0299] Orthosulfamuron may be applied to vegetation or areas adjacent to vegetation, or to the soil or water to prevent the emergence or growth of vegetation, in an amount sufficient to induce a herbicidal effect. In some embodiments, orthosulfamuron is at least 8g ai / ha, at least 9g ai / ha, at least 10g ai / ha, at least 11g ai / ha, at least 12g ai / ha, at least 13g ai / ha, at least 14g ai / ha, at least 15g ai / ha, at least 16g ai / ha, at least 17g ai / ha, at least 18g ai / ha, at least 19g ai / ha ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, 70g ai / ha or more, 71g 7. such as 72g ai / ha or more, 73g ai / ha or more, or 74g ai / ha or more.5g ai / ha or more; 74g ai / ha or less, 72g ai / ha or less, 70g ai / ha or less, 68g ai / ha or less, 66g ai / ha or less, 64g ai / ha or less, 62g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g less than ai / ha, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9g less than or equal to 75g ai / ha, such as less than or equal to 8g ai / ha; or less than or equal to 7.5-75g ai / ha, 7.5-60g ai / ha, 8-58g ai / ha, 9-42g ai / ha, 10-70g ai / ha, 10-56g ai / ha, 11-40g ai / ha, 13-64g ai / ha, 15~75g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation in an amount ranging from one of the minimum values listed above to one of the maximum values listed above, such as 17-46g ai / ha, 20-65g ai / ha, 20-52g ai / ha, 22-48g ai / ha, or 24-74g ai / ha.

[0300] Rimsulfuron The compositions and methods of the present disclosure may include rimsulfuron or an agriculturally acceptable salt or ester thereof. Rimsulfuron, shown below, is a sulfonylurea that provides post-emergence control of most annual and perennial grass weeds and some broadleaf weeds in corn, tomato, and potato at 15 g / ha. Rimsulfuron and methods for preparing rimsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0301] Rimsulfuron can be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, rimsulfuron is applied at a rate of 5.5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 7.An amount of 5 g ai / ha or more, such as 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 27 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more, 36 g ai / ha or more, 38 g ai / ha or more, 40 g ai / ha or more, 42 g ai / ha or more, 44 g ai / ha or more, 46 g ai / ha or more, 48 g ai / ha or more, 50 g ai / ha or more, 52 g ai / ha or more, 54 g ai / ha or more, 56 g ai / ha or more, 58 g ai / ha or more, 60 g ai / ha or more, 62 g ai / ha or more, 64 g ai / ha or more, 66 g ai / ha or more, 68 g ai / ha or more, 69 g ai / ha or more, 70 g ai / ha or more, 71 g ai / ha or more, 72 g ai / ha or more, 73 g ai / ha or more, or 74 g ai / ha or more; 74 g ai / ha or less, 73 g ai / ha or less, 72 g ai / ha or less, 71 g ai / ha or less, 70 g ai / ha or less, 69 g ai / ha or less, 68 g ai / ha or less, 66 g ai / ha or less, 64 g ai / ha or less, 62 g ai / ha or less, 60 g ai / ha or less, 58 g ai / ha or less, 56 g ai / ha or less, 54 g ai / ha or less, 52 g ai / ha or less, 50 g ai / ha or less, 48 g ai / ha or less, 46 g ai / ha or less, 44 g ai / ha or less, 42 g ai / ha or less, 40 g ai / ha or less, 38 g ai / ha or less, 36 g ai / ha or less, 34 g ai / ha or less, 32 g ai / ha or less, 30 g ai / ha or less, 28 g ai / ha or less, 27 g ai / ha or less, 26 g ai / ha or less, 24 g ai / ha or less, 22 g ai / ha or less, 20 g ai / ha or less, 18 g ai / ha or less, 16 g ai / ha or less, 14 g ai / ha or less, 12 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, 8 g ai / ha or less, 7.5 g ai / ha or less, 7 g ai / ha or less, 6 g ai / ha or less, 5.or applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation at a rate of 5g ai / ha or less, or 75g ai / ha or less, such as 5g ai / ha or less; or at a rate ranging from one of the above minimums to one of the above maximums, such as 5-75g ai / ha, 7.5-70g ai / ha, 9-64g ai / ha, 18-69g ai / ha, 27-36g ai / ha, 5.5-66g ai / ha, 14-18g ai / ha, 27-69g ai / ha, 7-38g ai / ha, 12-52g ai / ha, 9-44g ai / ha, 10-38g ai / ha, 16-75g ai / ha, or 20-48g ai / ha.

[0302] Sulfosulfuron The compositions and methods of the present disclosure may include sulfosulfuron or an agriculturally acceptable salt or ester thereof. Sulfosulfuron, shown below, is a sulfonylurea that provides control of annual broadleaf weeds and grass weeds, for example, in cereals. Sulfosulfuron and methods for preparing sulfosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0303] Sulfosulfuron may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, the sulfosulfuronate is 4.75 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, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, 70g ai / ha or more, 71g ai / ha or more, 72g ai / ha or more, 73g 4. such as more than ai / ha or more than 74g ai / ha.375g ai / ha or more; 74g ai / ha or less, 73g ai / ha or less, 72g ai / ha or less, 71g ai / ha or less, 70g ai / ha or less, 68g ai / ha or less, 66g ai / ha or less, 64g ai / ha or less, 62g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g less than ai / ha, 28g less than 26g ai / ha, less than 24g ai / ha, less than 22g ai / ha, less than 20g ai / ha, less than 18g ai / ha, less than 16g ai / ha, less than 14g ai / ha, less than 12g ai / ha, less than 10g ai / ha, less than 9g ai / ha, less than 8g ai / ha, less than 7g ai / ha, 6g 75g ai / ha or less, such as less than or equal to 5g ai / ha, or less than or equal to 4.75g ai / ha, or less than or equal to 4.5g ai / ha; ai / ha, 5~40g ai / ha, 6~75g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation in an amount ranging from one of the minimum values listed above to one of the maximum values listed above, such as 7-68g ai / ha, 7-52g ai / ha, 9-44g ai / ha, 10-50g ai / ha, 16-75g ai / ha, or 20-60g ai / ha.

[0304] Thifensulfuron The compositions and methods of the present disclosure may include thifensulfuron or its agriculturally acceptable salts or esters. Thifensulfuron-methyl, shown below, is a sulfonylurea that provides annual weed control in, for example, cereals, corn, and pastures. Thifensulfuron and methods for preparing thifensulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0305] Tefensulfuron can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to vegetation or to soil or water to prevent the emergence or growth of vegetation. In some embodiments, tefensulfuron is in an amount of 4.4 g ai / ha or more, such as 4.5 g ai / ha or more, 4.6 g ai / ha or more, 4.7 g ai / ha or more, 4.8 g ai / ha or more, 4.9 g ai / ha or more, 5 g ai / ha or more, 5.2 g ai / ha or more, 5.4 g ai / ha or more, 5.6 g ai / ha or more, 5.8 g ai / ha or more, 6 g ai / ha or more, 6.2 g ai / ha or more, 6.4 g ai / ha or more, 6.6 g ai / ha or more, 6.8 g ai / ha or more, 7 g ai / ha or more, 7.2 g ai / ha or more, 7.4 g ai / ha or more, 7.6 g ai / ha or more, 7.8 g ai / ha or more, 8 g ai / ha or more, 8.2 g ai / ha or more, 8.4 g ai / ha or more, 8.6 g ai / ha or more, 8.8 g ai / ha or more, 9 g ai / ha or more, 9.2 g ai / ha or more, 9.4 g ai / ha or more, 9.6 g ai / ha or more, 9.8 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, 16.2 g ai / ha or more, 16.4 g ai / ha or more, 16.6 g ai / ha or more, 16.8 g ai / ha or more, 17 g ai / ha or more, 17.1 g ai / ha or more, 17.2 g ai / ha or more, 17.3 g ai / ha or more, or 17.4 g ai / ha or more; 17.4 g ai / ha or less, 17.3 g ai / ha or less, 17.2 g ai / ha or less, 17.1 g ai / ha or less, 17 g ai / ha or less, 16.8 g ai / ha or less, 16.6 g ai / ha or less, 16.4 g ai / ha or less, 16.2 g ai / ha or less, 16 g 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, 9.8 g ai / ha or less, 9.6 g ai / ha or less, 9.4 g ai / ha or less, 9.2 g ai / ha or less, 9 g ai / ha or less, 8.8 g ai / ha or less, 8.6g ai / ha or less, 8.4g ai / ha or less, 8.2g ai / ha or less, 8g ai / ha or less, 7.8g ai / ha or less, 7.6g ai / ha or less, 7.4g ai / ha or less, 7.2g ai / ha or less, 7g ai / ha or less, 6.8g ai / ha or less, 6.6g ai / ha or less, 6.4g ai / ha or less, 6.2g ai / ha or less, 6g ai / ha or less, 5.8g ai / ha or less, 5.6g ai / ha or less, 5.4g ai / ha or less, 5.2g ai / ha or less, 5g ai / ha or less, 4.9g ai / ha or less, 4.8g ai / ha or less, 4.7g ai / ha or less, 4.6g ai / ha or less, 4.5g less than ai / ha or 4.4g or applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation at a rate of 17.5g ai / ha or less, such as 4.4-17.5g ai / ha, 4.5-16g ai / ha, 4.8-11g ai / ha, 5-17.3g ai / ha, 5-16.2g ai / ha, 5.4-13g ai / ha, 5.8-10g ai / ha, 6-12g ai / ha, 6-16g ai / ha, 7.4-16.4g ai / ha, 7.8-15g ai / ha, 8-15g ai / ha, or 8-17.1g ai / ha.

[0306] tribenuron The compositions and methods of the present disclosure may include tribenuron or an agriculturally acceptable salt or ester thereof. Tribenuron-methyl, shown below, is a sulfonylurea that provides post-emergence control of broadleaf weeds in cereal crops, including, for example, wheat, barley, oats, rye, and triticale. Tribenuron and methods for preparing tribenuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0307] Tribenuron can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to vegetation or to soil or water to prevent the germination or growth of vegetation. In some embodiments, tribenuron is at least 3.75 g ai / ha, such as at least 4 g ai / ha, at least 4.25 g ai / ha, at least 4.5 g ai / ha, at least 4.75 g ai / ha, at least 5 g ai / ha, at least 5.25 g ai / ha, at least 5.5 g ai / ha, at least 5.75 g ai / ha, at least 6 g ai / ha, at least 7 g ai / ha, at least 7.5 g ai / ha, at least 8 g ai / ha, at least 9 g ai / ha, at least 10 g ai / ha, at least 11 g ai / ha, at least 12 g ai / ha, at least 13 g ai / ha, at least 14 g ai / ha, at least 15 g ai / ha, at least 16 g ai / ha, at least 17 g ai / ha, at least 18 g ai / ha, at least 19 g ai / ha, at least 20 g ai / ha, at least 21 g ai / ha, at least 22 g ai / ha, at least 23 g ai / ha, at least 24 g ai / ha, at least 25 g ai / ha, at least 25.5 g ai / ha, at least 26 g ai / ha, at least 26.5 g ai / ha, at least 27 g ai / ha, at least 27.5 g ai / ha, at least 28 g ai / ha, at least 28.5 g ai / ha, at least 29 g ai / ha, at least 29.25 g ai / ha, at least 29.5 g ai / ha, or at least 29.75 g ai / ha; and up to 29.75 g ai / ha, up to 29.5 g ai / ha, up to 29.25 g ai / ha, up to 29 g ai / ha, up to 28.5 g ai / ha, up to 28 g ai / ha, up to 27.5 g ai / ha, up to 27 g ai / ha, up to 26.5 g ai / ha, up to 26 g ai / ha, up to 25 g ai / ha, up to 24 g ai / ha, up to 23 g ai / ha, up to 22 g ai / ha, up to 21 g ai / ha, up to 20 g ai / ha, up to 19 g ai / ha, up to 18 g ai / ha, up to 17 g ai / ha, up to 16 g ai / ha, up to 15 g ai / ha, up to 14 g ai / ha, up to 13 g ai / ha, up to 12 g ai / ha, up to 11 g ai / ha, up to 10 g ai / ha, up to 9 g ai / ha, up to 8 g ai / ha, up to 7.5 g ai / ha, up to 7 g ai / ha, up to 6 g ai / ha, up to 5.Amounts below 30g ai / ha, such as below 75g ai / ha, below 5.5g ai / ha, below 5.25g ai / ha, below 5g ai / ha, below 4.75g ai / ha, below 4.5g ai / ha, below 4.25g ai / ha, or below 4g ai / ha; or between 3.75 and 30g ai / ha, between 4 and 27.5g ai / ha, 4.25~23g ai / ha, 4.5~17g ai / ha, 5~25g ai / ha, 6~29.5g ai / ha, 7~28g ai / ha, 7.5~23g ai / ha, 7.5~20g ai / ha, 9~30g ai / ha, 10~19g ai / ha, or 10~27.5g It is applied to vegetation or areas adjacent to vegetation, or to soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from one of the minimum values above, such as ai / ha, to one of the maximum values above.

[0308] Synthetic auxin herbicides In addition to the compound according to formula I, the composition can contain synthetic auxin herbicides.Synthetic auxin herbicides can mimic natural plant hormones and inhibit cell division and growth.Synthetic auxin herbicides include phenoxy herbicides, benzoic acid herbicides, arylpicolinate herbicides, compounds according to formula Is, quinoline carboxylic acid herbicides, pyrimidine carboxylic acid herbicides, and benzothiazole herbicides, as well as their agriculturally acceptable salts and esters.

[0309] In some embodiments, the compositions may comprise a synthetic auxin herbicide selected from the group consisting of 2,4-D; 2,4-DB; 2,3,6-TBA, 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), indoloxypyr (such as indoloxypyr-cyanomethyl), mecoprop, mecoprop-P, MCPA, MCPA-thioethyl, MCPB, picloram, quinclorac, quinmerac, triclopyr, agriculturally acceptable salts and esters thereof, and combinations thereof. In some embodiments, synthetic auxin herbicides can include 2,4-D, MCPA, aminopyralid, clopyralid, dicamba, florpyrauxifen, fluroxypyr, halaxifen, quinclorac, agriculturally acceptable salts and esters thereof, and combinations thereof.

[0310] The synthetic auxin herbicide or an agriculturally acceptable salt or ester thereof may be applied to vegetation or an area adjacent to the vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of the vegetation. In some embodiments, the synthetic auxin herbicide or agriculturally acceptable salt or ester thereof has an ai of 1.5g ai or more, 2g ai or more, 2.5g ai or more, 3g ai or more, 3.5g ai or more, 4g ai or more, 4.5g ai or more, 5g ai or more, 6g ai or more, 7g ai or more, 8g ai or more, 9g ai or more, 10g ai or more, 15g ai or more, 20g ai or more, 25g ai or more, 30g ai or more, 35g ai or more, 40g ai or more, 45g ai or more, 50g ai or more, 55g ai or more, 60g ai or more, 65g ai or more, 70g ai or more, 75g ai or more, 80g ai or more, 85g ai or more, 90g ai or more, 95g ai or more, 100g ai or more, 110g ai or more, more than ai, more than 120g ai, more than 130g ai, more than 140g ai, more than 150g ai, more than 160g ai, more than 170g ai, more than 180g ai, more than 190g ai, more than 200g ai, more than 220g ai, more than 240g ai, more than 250g ai, more than 260g ai, 280g more than AI, more than 300g ai, more than 320g ai, more than 340g ai, more than 350g ai, more than 360g ai, more than 380g ai, more than 400g ai, more than 450g ai, more than 500g ai, more than 550g ai, more than 600g ai, more than 650g ai, more than 700g ai, 750g AI or above, 800g AI or above, 850g more than AI, more than 900g AI, more than 950g AI, more than 1000g AI, more than 1050g AI, more than 1100g AI, more than 1150g AI, more than 1200g AI, more than 1250g AI, more than 1300g AI, more than 1350g AI, more than 1400g AI, more than 1450g AI, 1500g more than AI, more than 1600g AI, more than 1700g AI, more than 1800g AI, more than 1900g AI, more than 2000g AI, more than 2050g AI, more than 2100g AI, more than 2150g AI, more than 2200g AI, more than 2240g AI, more than 2250g AI, 2300gai or above, 2350g ai or above, 2400g ai or above, 2450g ai or above, 2500g ai or above, 2600g ai or above, 2700g ai or above, 2750g ai or above, 2800g ai or above, 2900g ai or above, 3000g ai or above, 3050g ai or above, 3100g ai or above, 3150g ai or above, 3200g ai or above, 3250g ai or above, 3300g ai or above, 3350g ai or above, 3400g ai or above, 3450g ai or above, 3500g ai or above, 3600g ai or above, 3700g ai or above, 3750g ai or above, 3800g ai or above, 3900g ai or above, and 3950g ai or above Amount of acid equivalent (g ai) or more; 3950g ai or less, 3900g ai or less, 3800g ai or less, 3750g ai or less, 3700g ai or less, 3600g Below ai, below 3500g ai, below 3450g ai, below 3400g ai, below 3350g ai, below 3300g ai, below 3250g ai, below 3200g ai, below 3150g ai, below 3100g ai, below 3050g ai, below 3000g ai, below 2900g ai, 2800g ai below, 2750g ai below, 2700g ai below, 2600g ai or less, 2500g ai or less, 2450g ai or less, 2400g ai or less, 2350g ai or less, 2300g ai or less, 2250g ai or less, 2240g ai or less, 2200g ai or less, 2150g ai or less, 2100g ai or less, 2050g ai or less, 2000g ai or less, 1900g ai or less, 1800g ai or less, 1750g ai or less, 1700g ai or less, 1600g ai or less, 1500g ai or less, 1450g ai or less, 1400g ai or less, 1350g ai or less, 1300g ai or less, 1250g ai or less, 1240g ai or less, 1200g ai or less, 1150g ai or less, 1100g ai or less, 1050g ai or less, 1000g ai or less, 950g ai or less, 900g ai or less, 850g ai or less, 800g ai or less, 750g ai or less, 700g ai or less, 650g ai or less, 600g ai or less, 550g ai or less, 500g ai or less, 450g ai or less, 400gless than ai, less than 380g ai, less than 360g ai, less than 350g ai, less than 340g ai, less than 320g ai, less than 300g ai, less than 280g ai, less than 260g ai, less than 250g ai, less than 240g ai, less than 220g ai, less than 200g ai, less than 190g ai, 180g less than ai, less than 170g ai, less than 160g ai, less than 150g ai, less than 140g ai, less than 130g ai, less than 120g ai, less than 110g ai, less than 100g ai, less than 95g ai, less than 90g ai, less than 85g ai, less than 80g ai, less than 75g ai, less than 70g ai, 65g less than ai, 60g less than ai, 55g less than ai, 50g less than ai, less than 45g ai, less than 40g ai, less than 35g ai, less than 30g ai, less than 25g ai, 4000g such as less than 20g ai, less than 15g ai, less than 10g ai, less than 9g ai, less than 8g ai, less than 7g ai, less than 6g ai, less than 5g ai, less than 4.5g ai, less than 4g ai, less than 3.5g ai, less than 3g ai, less than 2.5g ai, less than 2g ai, less than 1.5g ai, or less than 1g ai Amount below ai; or 1~4000g ai, 1~2240g ai, 1~150g ai, 1.5~3150g ai, 2~900g ai, 2.5~3200g ai, 3~1250g ai, 5~260g ai, 6~750g ai, 7~2100g ai, 10~2240g ai, 20~3600g It is applied to vegetation or areas adjacent to vegetation or to soil or water to inhibit the emergence or growth of vegetation in an amount ranging from any of the minimum values listed above to any of the maximum values listed above, such as 40-3950g ai, 50-400g ai, 70-1250g ai, 100-1400g ai, or 250-1700g ai.

[0311] Phenoxycarboxylic acid In some embodiments, the composition comprises a compound according to Formula I and (b) 2,4-D, 2,4-DB2, clomeprop, dichlorprop, mecoprop, MCPA, MCPB, or an agriculturally acceptable salt or ester thereof.

[0312] 2,4-D In some embodiments, synthetic auxin herbicides can include 2,4-D or its agriculturally acceptable salts or esters. 2,4-D, as shown below, is a phenoxycarboxylic acid herbicide that provides broad-spectrum control of many annual, biennial, and perennial broadleaf weeds and aquatic broadleaf weeds in cereals, corn, sorghum, grassland, established turfgrass, grass seed crops, fruit trees (pome and stone fruits), cranberry, asparagus, sugarcane, rice, forests, and non-crop land (including areas adjacent to water). 2,4-D and methods for preparing 2,4-D are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0313] In some embodiments, 2,4-D can be provided as an agriculturally acceptable salt or ester of 2,4-D. Exemplary agriculturally acceptable salts and esters of 2,4-D include 2,4-D-ammonium, 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-choline, 2,4-D-diethylammonium, 2,4-D-dimethylammonium (2,4-D DMA), 2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-D-ethyl, 2,4-D-2-ethylhexyl (2,4-D DMA), and 2,4-D-dimethylammonium (2,4-D DMA). Examples of 2,4-D-containing ammonium salts include, but are not limited to, 2,4-D-heptylammonium, 2,4-D-isobutylammonium, 2,4-D-isooctylammonium, 2,4-D-isopropylammonium, 2,4-D-isopropylammonium, 2,4-D-lithium, 2,4-D-meptylammonium, 2,4-D-methylammonium, 2,4-D-octylammonium, 2,4-D-pentylammonium, 2,4-D-propylammonium, 2,4-D-sodiumammonium, 2,4-D-tefurylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-trolamine, and Clasiphos. In some embodiments, 2,4-D can be provided as 2,4-D-2-ethylhexylammonium (2,4-D EHE), as shown below. [ka]

[0314] In some embodiments, the 2,4-D can be provided as 2,4-D DMA, shown below. [ka]

[0315] In some embodiments, 2,4-D can be provided as 2,4-D choline, shown below. [ka]

[0316] In some embodiments, 2,4-D can be provided as 2,4-D triethanolamine (2,4-D-trolamine), shown below. [ka]

[0317] Exemplary uses of 2,4-D-choline include, but are not limited to, controlling annual and perennial broadleaf weeds, including but not limited to glyphosate-resistant broadleaf weeds.2,4-D-choline can be used in crops that are made to be 2,4-D tolerant, including but not limited to 2,4-D-resistant soybeans, corn, and cotton.2,4-D-choline is generally applied after emergence, but this is not necessary.2,4-D-choline can also be used to control weeds in non-crop and perennial cropping systems.

[0318] 2,4-D may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, 2,4-D is at least 2g ai / ha, at least 3g ai / ha, at least 4g ai / ha, at least 5g ai / ha, at least 6g ai / ha, at least 7g ai / ha, at least 8g ai / ha, at least 9g ai / ha, at least 10g ai / ha, at least 15g ai / ha, at least 20g ai / ha, at least 25g ai / ha, at least 30g ai / ha ai / ha or more, 35g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 60g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 90g ai / ha or more, 100g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more, 1000g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g ai / ha or more, 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2100g ai / ha or more, 2200g ai / ha or more, 2240g ai / ha or more, 2250g ai / ha or more, 2300g ai / ha or more, 2400g ai / ha or more, 2500g ai / ha or more, 2600g ai / ha or more, 2700g ai / ha or more, 2800g ai / ha or more, 2900g ai / ha or more, 3000g ai / ha or more, 3100g ai / ha or more, 3200gan amount of active ingredient per hectare (g ai / ha) of 1 gram or more, such as 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, 3850 g ai / ha or more, 3900 g ai / ha or more, or 3950 g ai / ha or more; 3950 g ai / ha or less, 3900 g ai / ha or less, 3850 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, 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, 2250 g ai / ha or less, 2240 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, 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, 375 g ai / ha or less, 350 g ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 gai / ha or less, 80g ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 60g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g ai / ha or less, 20g ai / ha or less, 15g ai / ha or less, 10g 4000g ai / ha or less, such as less than 9g ai / ha, less than 8g ai / ha, less than 7g ai / ha, less than 6g ai / ha, less than 5g ai / ha, less than 4g ai / ha, less than 3g ai / ha, or less than 2g ai / ha; or 1~4000g ai / ha, 1~150g ai / ha, 2~3100g ai / ha, 2~900g It is applied to vegetation or an area adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values above to any of the maximum values above, such as 3-2600g ai / ha, 3-1200g ai / ha, 5-275g ai / ha, 6-750g ai / ha, 7-2100g ai / ha, 10-2240g ai / ha, 20-3300g ai / ha, 40-3950g ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700g ai / ha.

[0319] 2,4-DB In some embodiments, the synthetic auxin herbicide may include 2,4-DB, a phenoxycarboxylic acid herbicide that provides post-emergence control of many annual and perennial broadleaf weeds in alfalfa, clover, cereals, grasslands, forage, legumes, soybeans, and peanuts. 2,4-DB and methods for producing 2,4-DB are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0320] In some embodiments, 2,4-DB can be provided as an agriculturally acceptable salt or ester of 2,4-DB. Exemplary agriculturally acceptable salts and esters of 2,4-DB include, but are not limited to, 2,4-DB-butyl, 2,4-DB-dimethylammonium (2,4-DB DMA), 2,4-DB-isoctyl, 2,4-DB-potassium, and 2,4-DB-sodium.

[0321] 2,4-DB can be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, the 2,4-DB is 2g ai / ha or more, 3g ai / ha or more, 4g ai / ha or more, 5g ai / ha or more, 6g ai / ha or more, 7g ai / ha or more, 8g ai / ha or more, 9g ai / ha or more, 10g ai / ha or more, 15g ai / ha or more, 20g ai / ha or more, 25g ai / ha or more, 30g ai / ha or more ai / ha or more, 35g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 60g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 90g ai / ha or more, 100g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more, 1000g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g ai / ha or more, 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2100g ai / ha or more, 2200g ai / ha or more, 2240g ai / ha or more, 2250g ai / ha or more, 2300g ai / ha or more, 2400g ai / ha or more, 2500g ai / ha or more, 2600g ai / ha or more, 2700g ai / ha or more, 2800g ai / ha or more, 2900g ai / ha or more, 3000g ai / ha or more, 3100gamounts of 1 g ai / ha or more, such as 3,100 g ai / ha or more, 3,200 g ai / ha or more, 3,300 g ai / ha or more, 3,400 g ai / ha or more, 3,500 g ai / ha or more, 3,600 g ai / ha or more, 3,700 g ai / ha or more, 3,750 g ai / ha or more, 3,800 g ai / ha or more, 3,850 g ai / ha or more, 3,900 g ai / ha or more, or 3,950 g ai / ha or more; 3,950 g ai / ha or less, 3,900 g ai / ha or less, 3,850 g ai / ha or less, 3,800 g ai / ha or less, 3,750 g ai / ha or less, 3,700 g ai / ha or less, 3,600 g ai / ha or less, 3,500 g ai / ha or less, 3,400 g ai / ha or less, 3,300 g ai / ha or less, 3,200 g ai / ha or less, 3,100 g ai / ha or less, 3,000 g ai / ha or less, 2,900 g ai / ha or less, 2,800 g ai / ha or less, 2,700 g ai / ha or less, 2,600 g ai / ha or less, 2,500 g ai / ha or less, 2,400 g ai / ha or less, 2,300 g ai / ha or less, 2,250 g ai / ha or less, 2,240 g ai / ha or less, 2,200 g ai / ha or less, 2,100 g ai / ha or less, 2,000 g ai / ha or less, 1,900 g ai / ha or less, 1,800 g ai / ha or less, 1,700 g ai / ha or less, 1,600 g ai / ha or less, 1,500 g ai / ha or less, 1,400 g ai / ha or less, 1,300 g ai / ha or less, 1,200 g ai / ha or less, 1,100 g ai / ha or less, 1,000 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, 375 g ai / ha or less, 350 g ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 gless than 75g ai / ha, less than 70g ai / ha, less than 60g ai / ha, less than 50g ai / ha, less than 45g ai / ha, less than 40g ai / ha, less than 35g ai / ha, less than 30g ai / ha, less than 25g ai / ha, less than 20g ai / ha, less than 15g ai / ha, less than 10g ai / ha, 9g Amount below 4000g ai / ha, such as below 8g ai / ha, below 7g ai / ha, below 6g ai / ha, below 5g ai / ha, below 4g ai / ha, below 3g ai / ha, or below 2g ai / ha; or 1~4000g ai / ha, 1~150g ai / ha, 2~3100g ai / ha, 2~900g ai / ha, 3~2600g It is applied to vegetation or an area adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values above to any of the maximum values above, such as 0.01 ai / ha, 3-1200g ai / ha, 5-275g ai / ha, 6-750g ai / ha, 7-2100g ai / ha, 10-2240g ai / ha, 20-3300g ai / ha, 40-3950g ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700g ai / ha.

[0322] Clomeprop In some embodiments, the synthetic auxin herbicide may include clomeprop or an agriculturally acceptable salt or ester thereof. Clomeprop, shown below, is a phenoxycarboxylic acid herbicide that provides pre-emergence to early post-emergence control of broadleaf and sedge weeds in paddy rice. Clomeprop and methods for preparing clomeprop are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0323] Dichlorprop In some embodiments, the synthetic auxin herbicide can include dichlorprop or its agriculturally acceptable salt or ester. Dichlorprop, as shown below, is a phenoxycarboxylic acid herbicide that provides broad-spectrum control of annual and perennial broadleaf weeds in cereals and grasslands; scrub control in non-agricultural lands; broadleaf aquatic weed control; and bank and roadside maintenance. Dichlorprop and methods for producing dichlorprop are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0324] In some embodiments, dichlorprop may be provided as an agriculturally acceptable salt or ester of dichlorprop. Exemplary agriculturally acceptable salts and esters of dichlorprop include, but are not limited to, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-ethylammonium, dichlorprop-2-ethylhexyl, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-2-ethylhexyl, dichlorprop-P-potassium, and dichlorprop-P-sodium. In some embodiments, dichlorprop may be provided as the stereoisomer dichlorprop-P shown below. [ka]

[0325] Dichlorprop may be applied to vegetation or areas adjacent to vegetation, or to the soil or water to prevent the emergence or growth of vegetation, in an amount sufficient to induce a herbicidal effect. In some embodiments, dichlorprop is 2g ai / ha or more, 3g ai / ha or more, 4g ai / ha or more, 5g ai / ha or more, 6g ai / ha or more, 7g ai / ha or more, 8g ai / ha or more, 9g ai / ha or more, 10g ai / ha or more, 15g ai / ha or more, 20g ai / ha or more, 25g ai / ha or more, 30g ai / ha or more, 35g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 60g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 90g ai / ha or more, 100g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more, 1000g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g ai / ha or more, 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2100g ai / ha or more, 2200g ai / ha or more, 2240g ai / ha or more, 2250g ai / ha or more, 2300g ai / ha or more, 2400g ai / ha or more, 2500g ai / ha or more, 2600g ai / ha or more, 2700g ai / ha or more, 2800g ai / ha or more, 2900g ai / ha or more, 3000g ai / ha or more, 3100gan amount of 1 g ai / ha or more, such as 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, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3850 g ai / ha or more, 3900 g ai / ha or more, or 3950 g ai / ha or more; 3950 g ai / ha or less, 3900 g ai / ha or less, 3850 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, 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, 2250 g ai / ha or less, 2240 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, 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, 375 g ai / ha or less, 350 g ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 gless than 75g ai / ha, less than 70g ai / ha, less than 60g ai / ha, less than 50g ai / ha, less than 45g ai / ha, less than 40g ai / ha, less than 35g ai / ha, less than 30g ai / ha, less than 25g ai / ha, less than 20g ai / ha, less than 15g ai / ha, less than 10g ai / ha, 9g Amount below 4000g ai / ha, such as below 8g ai / ha, below 7g ai / ha, below 6g ai / ha, below 5g ai / ha, below 4g ai / ha, below 3g ai / ha, or below 2g ai / ha; or 1~4000g ai / ha, 1~150g ai / ha, 2~3100g ai / ha, 2~900g ai / ha, 3~2600g It is applied to vegetation or an area adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values above to any of the maximum values above, such as 0.01 ai / ha, 3-1200g ai / ha, 5-275g ai / ha, 6-750g ai / ha, 7-2100g ai / ha, 10-2240g ai / ha, 20-3300g ai / ha, 40-3950g ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700g ai / ha.

[0326] Mecoprop In some embodiments, the synthetic auxin herbicide can include mecoprop or an agriculturally acceptable salt or ester thereof. Mecoprop, shown below, is a phenoxycarboxylic acid herbicide that provides broad-spectrum control of broadleaf weeds in wheat, barley, oats, herbaceous seed crops, grasslands, and fruit trees and vines. Mecoprop also provides control of dock (Rumex spp.) in grasslands and pastures. Mecoprop and methods for producing mecoprop are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0327] In some embodiments, mecoprop may be provided as an agriculturally acceptable salt or ester of mecoprop. Exemplary agriculturally acceptable salts and esters of mecoprop include, but are not limited to, mecoprop-butotyl, mecoprop-potassium, mecoprop-sodium, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-trolamine, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-ethylhexyl, and mecoprop-P-potassium. In some embodiments, mecoprop may be provided as the stereoisomer mecoprop-P, shown below. [ka]

[0328] Mecoprop may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some aspects, the mecoprop is 2g ai / ha or more, 3g ai / ha or more, 4g ai / ha or more, 5g ai / ha or more, 6g ai / ha or more, 7g ai / ha or more, 8g ai / ha or more, 9g ai / ha or more, 10g ai / ha or more, 15g ai / ha or more, 20g ai / ha or more, 25g ai / ha or more, 30g ai / ha or more, 35g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 60g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 90g ai / ha or more, 100g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more, 1000g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g ai / ha or more, 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2100g ai / ha or more, 2200g ai / ha or more, 2240g ai / ha or more, 2250g ai / ha or more, 2300g ai / ha or more, 2400g ai / ha or more, 2500g ai / ha or more, 2600g ai / ha or more, 2700g ai / ha or more, 2800g ai / ha or more, 2900g ai / ha or more, 3000g ai / ha or more, 3100gan amount of 1 g ai / ha or more, such as 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, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3850 g ai / ha or more, 3900 g ai / ha or more, or 3950 g ai / ha or more; 3950 g ai / ha or less, 3900 g ai / ha or less, 3850 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, 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, 2250 g ai / ha or less, 2240 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, 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, 375 g ai / ha or less, 350 g ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 gless than 75g ai / ha, less than 70g ai / ha, less than 60g ai / ha, less than 50g ai / ha, less than 45g ai / ha, less than 40g ai / ha, less than 35g ai / ha, less than 30g ai / ha, less than 25g ai / ha, less than 20g ai / ha, less than 15g ai / ha, less than 10g ai / ha, 9g Amount below 4000g ai / ha, such as below 8g ai / ha, below 7g ai / ha, below 6g ai / ha, below 5g ai / ha, below 4g ai / ha, below 3g ai / ha, or below 2g ai / ha; or 1~4000g ai / ha, 1~150g ai / ha, 2~3100g ai / ha, 2~900g ai / ha, 3~2600g It is applied to vegetation or an area adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values above to any of the maximum values above, such as 0.01 ai / ha, 3-1200g ai / ha, 5-275g ai / ha, 6-750g ai / ha, 7-2100g ai / ha, 10-2240g ai / ha, 20-3300g ai / ha, 40-3950g ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700g ai / ha.

[0329] MCPA In some embodiments, synthetic auxin herbicide can include MCPA or its agriculturally acceptable salt or ester.MCPA shown below is a phenoxycarboxylic acid herbicide that provides broad-spectrum control of many annual, biennial and perennial broadleaf weeds, woody weeds and aquatic broadleaf weeds in cereals, herbaceous seed crops, flax, rice, vines, peas, potatoes, asparagus, grasslands, turf, under fruit trees, forests, and on roadsides and banks.MCPA and the method for preparing MCPA are known in the art.Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0330] In some embodiments, MCPA can be provided as an agriculturally acceptable salt or ester of MCPA. Exemplary agriculturally acceptable salts of MCPA include, but are not limited to, MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium (MCPA-DMA), MCPA-diolamine, MCPA-ethyl, MCPA-2-ethylhexyl (MCPA EHE), MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, and MCPA-trolamine. In some embodiments, MCPA can be provided as MCPA-2-ethylhexyl (MCPA EHE), as shown below. [ka]

[0331] In some embodiments, MCPA can be provided as MCPA-dimethylammonium (MCPA-DMA), shown below. [ka]

[0332] MCPA may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of the vegetation. In some embodiments, the MCPA is 2 g ai / ha or more, 3 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, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more ai / ha or more, 35g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 60g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 90g ai / ha or more, 100g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more, 1000g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g ai / ha or more, 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2100g ai / ha or more, 2200g ai / ha or more, 2240g ai / ha or more, 2250g ai / ha or more, 2300g ai / ha or more, 2400g ai / ha or more, 2500g ai / ha or more, 2600g ai / ha or more, 2700g ai / ha or more, 2800g ai / ha or more, 2900g ai / ha or more, 3000g ai / ha or more, 3100g ai / ha or more, 3200gan amount of 1 g ai / ha or more, such as 3,200 g ai / ha or more, 3,300 g ai / ha or more, 3,400 g ai / ha or more, 3,500 g ai / ha or more, 3,600 g ai / ha or more, 3,700 g ai / ha or more, 3,750 g ai / ha or more, 3,800 g ai / ha or more, 3,850 g ai / ha or more, 3,900 g ai / ha or more, or 3,950 g ai / ha or more; 3,950 g ai / ha or less, 3,900 g ai / ha or less, 3,850 g ai / ha or less, 3,800 g ai / ha or less, 3,750 g ai / ha or less, 3,700 g ai / ha or less, 3,600 g ai / ha or less, 3,500 g ai / ha or less, 3,400 g ai / ha or less, 3,300 g ai / ha or less, 3,200 g ai / ha or less, 3,100 g ai / ha or less, 3,000 g ai / ha or less, 2,900 g ai / ha or less, 2,800 g ai / ha or less, 2,700 g ai / ha or less, 2,600 g ai / ha or less, 2,500 g ai / ha or less, 2,400 g ai / ha or less, 2,300 g ai / ha or less, 2,250 g ai / ha or less, 2,240 g ai / ha or less, 2,200 g ai / ha or less, 2,100 g ai / ha or less, 2,000 g ai / ha or less, 1,900 g ai / ha or less, 1,800 g ai / ha or less, 1,700 g ai / ha or less, 1,600 g ai / ha or less, 1,500 g ai / ha or less, 1,400 g ai / ha or less, 1,300 g ai / ha or less, 1,200 g ai / ha or less, 1,100 g ai / ha or less, 1,000 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, 375 g ai / ha or less, 350 g ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 75 gless than 70g ai / ha, less than 60g ai / ha, less than 50g ai / ha, less than 45g ai / ha, less than 40g ai / ha, less than 35g ai / ha, less than 30g ai / ha, less than 25g ai / ha, less than 20g ai / ha, less than 15g ai / ha, less than 10g ai / ha, less than 9g ai / ha, 8g Amounts below 4000g ai / ha, such as below 7g ai / ha, below 6g ai / ha, below 5g ai / ha, below 4g ai / ha, below 3g ai / ha, or below 2g ai / ha; or 1-4000g ai / ha, 1-150g ai / ha, 2-3100g ai / ha, 2-900g ai / ha, 3~2600g It is applied to vegetation or an area adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values above to any of the maximum values above, such as 0.01 ai / ha, 3-1200g ai / ha, 5-275g ai / ha, 6-750g ai / ha, 7-2100g ai / ha, 10-2240g ai / ha, 20-3300g ai / ha, 40-3950g ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700g ai / ha.

[0333] MCPB In some embodiments, the synthetic auxin herbicide may include MCPB or its agriculturally acceptable salt or ester. MCPB, shown below, is a phenoxycarboxylic acid herbicide that provides broad-spectrum control of many broadleaf weeds, woody weeds, and aquatic broadleaf weeds in rice, cereals, clover, sainfoin, pea, peanut, grassland, turf, and forest. MCPB and methods for preparing MCPB are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0334] In some embodiments, MCPB can be provided as an agriculturally acceptable salt or ester of MCPB. Exemplary agriculturally acceptable salts of MCPB include, but are not limited to, MCPB-ethyl, MCPB-potassium, and MCPB-sodium.

[0335] MCPB may be applied to vegetation or areas adjacent to vegetation, or to the soil or water to prevent the emergence or growth of vegetation, in an amount sufficient to induce a herbicidal effect. In some embodiments, the MCPB is 2 g ai / ha or more, 3 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, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more ai / ha or more, 35g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 60g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 90g ai / ha or more, 100g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more, 1000g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g ai / ha or more, 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2100g ai / ha or more, 2200g ai / ha or more, 2240g ai / ha or more, 2250g ai / ha or more, 2300g ai / ha or more, 2400g ai / ha or more, 2500g ai / ha or more, 2600g ai / ha or more, 2700g ai / ha or more, 2800g ai / ha or more, 2900g ai / ha or more, 3000g ai / ha or more, 3100g ai / ha or more, 3200gan amount of 1 g ai / ha or more, such as 3,200 g ai / ha or more, 3,300 g ai / ha or more, 3,400 g ai / ha or more, 3,500 g ai / ha or more, 3,600 g ai / ha or more, 3,700 g ai / ha or more, 3,750 g ai / ha or more, 3,800 g ai / ha or more, 3,850 g ai / ha or more, 3,900 g ai / ha or more, or 3,950 g ai / ha or more; 3,950 g ai / ha or less, 3,900 g ai / ha or less, 3,850 g ai / ha or less, 3,800 g ai / ha or less, 3,750 g ai / ha or less, 3,700 g ai / ha or less, 3,600 g ai / ha or less, 3,500 g ai / ha or less, 3,400 g ai / ha or less, 3,300 g ai / ha or less, 3,200 g ai / ha or less, 3,100 g ai / ha or less, 3,000 g ai / ha or less, 2,900 g ai / ha or less, 2,800 g ai / ha or less, 2,700 g ai / ha or less, 2,600 g ai / ha or less, 2,500 g ai / ha or less, 2,400 g ai / ha or less, 2,300 g ai / ha or less, 2,250 g ai / ha or less, 2,240 g ai / ha or less, 2,200 g ai / ha or less, 2,100 g ai / ha or less, 2,000 g ai / ha or less, 1,900 g ai / ha or less, 1,800 g ai / ha or less, 1,700 g ai / ha or less, 1,600 g ai / ha or less, 1,500 g ai / ha or less, 1,400 g ai / ha or less, 1,300 g ai / ha or less, 1,200 g ai / ha or less, 1,100 g ai / ha or less, 1,000 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, 375 g ai / ha or less, 350 g ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 75 gless than 70g ai / ha, less than 60g ai / ha, less than 50g ai / ha, less than 45g ai / ha, less than 40g ai / ha, less than 35g ai / ha, less than 30g ai / ha, less than 25g ai / ha, less than 20g ai / ha, less than 15g ai / ha, less than 10g ai / ha, less than 9g ai / ha, 8g Amounts below 4000g ai / ha, such as below 7g ai / ha, below 6g ai / ha, below 5g ai / ha, below 4g ai / ha, below 3g ai / ha, or below 2g ai / ha; or 1-4000g ai / ha, 1-150g ai / ha, 2-3100g ai / ha, 2-900g ai / ha, 3~2600g It is applied to vegetation or an area adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values above to any of the maximum values above, such as 0.01 ai / ha, 3-1200g ai / ha, 5-275g ai / ha, 6-750g ai / ha, 7-2100g ai / ha, 10-2240g ai / ha, 20-3300g ai / ha, 40-3950g ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700g ai / ha.

[0336] benzoic acid In some embodiments, the composition comprises a compound according to Formula I and (b) chloramben, dicamba, TBA, or an agriculturally acceptable salt or ester thereof.

[0337] Chloramben In some embodiments, the synthetic auxin herbicide may include chloramben or its agriculturally acceptable salt or ester. Chloramben, shown below, is a benzoic acid herbicide that provides pre-plant and pre-emergence control of grasses and broadleaf weeds in asparagus, white beans, peanuts, corn, sweet potato, pumpkin, soybean, squash, sunflower, and certain ornamental plants. Chloramben and methods for preparing chloramben are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0338] Dicamba In some embodiments, the synthetic auxin herbicide may include dicamba or its agriculturally acceptable salt or ester. Dicamba, shown below, is a benzoic acid herbicide that provides broad-spectrum control of annual and perennial broadleaf weeds and woody species in cereals, corn, sorghum, sugarcane, asparagus, perennial grasses, turfgrass, pastures, rangelands, and non-croplands. Dicamba and methods for producing dicamba are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0339] In some aspects, the dicamba can be provided as an agriculturally acceptable salt or ester of dicamba. Exemplary agriculturally acceptable salts and esters of dicamba include, but are not limited to, dicamba-diglycolammonium, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-methyl, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-trolamine, and camphendichlor.

[0340] In some embodiments, the dicamba can be provided as dicamba-diglycolammonium, shown below. [ka]

[0341] Dicamba can be applied to vegetation or areas adjacent to vegetation, or to the soil or water to prevent the emergence or growth of vegetation, in an amount sufficient to induce a herbicidal effect. In some embodiments, dicamba is at least 55g ai / ha, at least 60g ai / ha, at least 65g ai / ha, at least 70g ai / ha, at least 75g ai / ha, at least 80g ai / ha, at least 85g ai / ha, at least 90g ai / ha, at least 95g ai / ha, at least 100g ai / ha, at least 110g ai / ha, at least 120g ai / ha, at least 125g ai / ha, at least 130g ai / ha, at least 140g ai / ha, at least 150g ai / ha, at least 160g ai / ha, at least 170g ai / ha, at least 175g ai / ha, at least 180g ai / ha, at least 190g ai / ha, at least 200g ai / ha, at least 210g ai / ha, at least 220g ai / ha, at least 225g ai / ha, ai / ha or more, 230g ai / ha or more, 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more, 270g ai / ha or more, 275g ai / ha or more, 280g ai / ha or more, 290g ai / ha or more, 300g ai / ha or more, 310g ai / ha or more, 320g ai / ha or more, 325g ai / ha or more, 330g ai / ha or more, 340g ai / ha or more, 350g ai / ha or more, 360g ai / ha or more, 370g ai / ha or more, 375g ai / ha or more, 380g ai / ha or more, 390g ai / ha or more, 400g ai / ha or more, 425g ai / ha or more, 450g ai / ha or more, 475g amounts of 50g ai / ha or more, such as 500g ai / ha or more, 525g ai / ha or more, 550g ai / ha or more, 560g ai / ha or more, 570g ai / ha or more, 575g ai / ha or more, 580g ai / ha or more, 590g ai / ha or more, or 600g ai / ha or more;590g ai / ha or less, 580g ai / ha or less, 575g ai / ha or less, 570g ai / ha or less, 560g ai / ha or less, 550g ai / ha or less, 525g ai / ha or less, 500g ai / ha or less, 475g ai / ha or less, 450g ai / ha or less, 425g ai / ha or less, 400g ai / ha or less, 390g ai / ha or less, 380g ai / ha or less, 375g ai / ha or less, 370g ai / ha or less, 360g ai / ha or less, 350g ai / ha or less, 340g ai / ha or less, 330g ai / ha or less, 325g ai / ha or less, 320g ai / ha or less, 310g ai / ha or less, 300g ai / ha or less, 290g ai / ha or less, 280g ai / ha or less, 275g ai / ha or less, 270g ai / ha or less, 260g ai / ha or less, 250g ai / ha or less, 240g ai / ha or less, 230g ai / ha or less, 225g ai / ha or less, 220g ai / ha or less, 210g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 175g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 125g ai / ha or less, 120g ai / ha or less, 110g less than ai / ha, 100g less than ai / ha, 95g Amounts below 600g ai / ha, such as below 90g ai / ha, below 85g ai / ha, below 80g ai / ha, below 75g ai / ha, below 70g ai / ha, below 65g ai / ha, below 60g ai / ha, or below 55g ai / ha; or between 50 and 600g ai / ha, between 55 and 150g ai / ha, 60~310g ai / ha, 65~190g ai / ha, 80~560g ai / ha, 85~300g ai / ha, 100~275g ai / ha, 120~475g ai / ha, 140~390g ai / ha, 150~250g ai / ha, or 250~400g It is applied to vegetation or areas adjacent to vegetation, or to soil or water, to prevent the emergence or growth of vegetation at a rate ranging from any of the minimum values above, such as ai / ha, to any of the maximum values above;

[0342] 2,3,6-TBA In some embodiments, the synthetic auxin herbicide may include 2,3,6-TBA or its agriculturally acceptable salt or ester. 2,3,6-TBA, shown below, is a benzoic acid herbicide that provides post-emergence control of certain broadleaf annual and perennial weeds in cereals and grass seed crops. 2,3,6-TBA and methods for preparing 2,3,6-TBA are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0343] C. Arylpicolinates In some embodiments, the composition comprises a compound according to Formula I and (b) florpilauxifen, halauxifen, or an agriculturally acceptable salt or ester thereof.

[0344] Florpilauxiphen In some embodiments, the synthetic auxin herbicide can include florpilauxifen or an agriculturally acceptable salt or ester thereof. Florpilauxifen is an aryl picolinic acid described in U.S. Patent No. 7,314,849 B2. Exemplary uses of florpilauxifen include the control of undesirable vegetation, including grass, broadleaf, and sedge weeds, in several non-agricultural and cropping situations. [ka]

[0345] In some aspects, florpilauxifen may be provided as an agriculturally acceptable salt or ester of florpilauxifen. Exemplary agriculturally acceptable salts and esters of florpilauxifen include, but are not limited to, florpilauxifen-benzyl, as shown below. [ka]

[0346] Florpilauxifen may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, the florpyrauxifen is 2 g ai / ha or more, 3 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, 12.5 g ai / ha or more, 15 g ai / ha or more, 17.5 g ai / ha or more, 20g ai / ha or more, 25g ai / ha or more, 30g ai / ha or more, 35g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 60g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 90g ai / ha or more, 100g ai / ha or more, 110g Amount of 1g ai / ha or more, such as 120g ai / ha or more, 125g ai / ha or more, 130g ai / ha or more, 140g ai / ha or more, 142.5g ai / ha or more, 145g ai / ha or more, 147.5g ai / ha or more, or 149g ai / ha or more; 149g ai / ha or less, 147.5g ai / ha or less, 145g ai / ha or less, 142.5g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 125g ai / ha or less, 120g ai / ha or less, 110g ai / ha or less, 100g ai / ha or less, 90g ai / ha or less, 80g ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 60g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g ai / ha or less, 20g ai / ha or less, 17.5g ai / ha or less, 15g ai / ha or less, 12.Amounts below 150g ai / ha, such as below 5g ai / ha, below 10g ai / ha, below 9g ai / ha, below 8g ai / ha, below 7g ai / ha, below 6g ai / ha, below 5g ai / ha, below 4g ai / ha, below 3g ai / ha, or below 2g ai / ha; or between 1 and 150g ai / ha, between 2 and 130g ai / ha, 2~45g ai / ha, 3~70g ai / ha, 4~147.5g ai / ha, 5~100g ai / ha, 6~75g ai / ha, 7~50g ai / ha, 10~149g ai / ha, 20~120g ai / ha, 25~90g ai / ha, 30~60g ai / ha, 50~150g ai / ha, 60~130g It is applied to vegetation or areas adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation at a rate ranging from any of the minimum values listed above, such as 100 to 145 g ai / ha, to any of the maximum values listed above.

[0347] Halaxifene In some aspects, the synthetic auxin herbicide can include halauxifen or an agriculturally acceptable salt or ester thereof. Halauxifen, shown below, is an aryl picolinic acid herbicide that provides broad-spectrum control of broadleaf weeds in cereal crops. [ka]

[0348] In some aspects, halauxifene can be provided as an agriculturally acceptable salt or ester of halauxifene. Exemplary agriculturally acceptable salts and esters of halauxifene include, but are not limited to, halauxifene-methyl. In some aspects, halauxifene is provided as halauxifene-methyl, as shown below: [ka]

[0349] Halauxifen can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to the vegetation or to soil or water in order to prevent the emergence or growth of vegetation. In some embodiments, halauxifen is in an amount of 1 g ai / ha or more, such as 2 g ai / ha or more, 2.5 g ai / ha or more, 3 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, 12.5 g ai / ha or more, 15 g ai / ha or more, 17.5 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, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 90 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, 142.5 g ai / ha or more, 145 g ai / ha or more, 147.5 g ai / ha or more, or 149 g ai / ha or more; 149 g ai / ha or less, 147.5 g ai / ha or less, 145 g ai / ha or less, 142.5 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, 90 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 60 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, 17.5 g ai / ha or less, 15 g ai / ha or less, 12.5 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 g ai / ha or less, 2.or applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation at a rate of 150g ai / ha or less, such as 5g ai / ha or less, or 2g ai / ha or less; or at a rate ranging from any of the above minimums to any of the above maximums, such as 1-150g ai / ha, 2-130g ai / ha, 2.5-45g ai / ha, 3-70g ai / ha, 4-147.5g ai / ha, 5-100g ai / ha, 6-75g ai / ha, 7-50g ai / ha, 10-149g ai / ha, 20-120g ai / ha, 25-90g ai / ha, 30-60g ai / ha, 50-150g ai / ha, 60-130g ai / ha, or 100-145g ai / ha.

[0350] Pyridine carboxylate In some embodiments, the composition comprises a compound according to Formula I and (b) aminopyralid, clopyralid, fluroxypyr, picloram, triclopyr, or an agriculturally acceptable salt or ester thereof.

[0351] Aminopyralid In some embodiments, the synthetic auxin herbicide may include aminopyralid or an agriculturally acceptable salt or ester thereof. Aminopyralid is a compound according to Formula I that provides pre-emergence and post-emergence control of certain annual and perennial broadleaf weeds in grasslands. Aminopyralid and methods for producing aminopyralid are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0352] In some embodiments, aminopyralid can be provided as an agriculturally acceptable salt or ester of aminopyralid. Exemplary agriculturally acceptable salts and esters of aminopyralid include, but are not limited to, aminopyralid-triisopropanolammonium (TIPA), shown below. [ka]

[0353] Aminopyralid can be applied in an amount sufficient to induce a herbicidal effect to vegetation or an area adjacent to vegetation or to soil or water in order to prevent the germination or growth of vegetation. In some embodiments, aminopyralid is an amount of 1 g ai / ha or more, such as 2 g ai / ha or more, 2.5 g ai / ha or more, 3 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, 12.5 g ai / ha or more, 15 g ai / ha or more, 17.5 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, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 90 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, 142.5 g ai / ha or more, 145 g ai / ha or more, 147.5 g ai / ha or more, or 149 g ai / ha or more; 149 g ai / ha or less, 147.5 g ai / ha or less, 145 g ai / ha or less, 142.5 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, 90 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 60 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, 17.5 g ai / ha or less, 15 g ai / ha or less, 12.5 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 g ai / ha or less, 2.or applied to vegetation or areas adjacent to vegetation, or to the soil or water, to prevent the emergence or growth of vegetation at a rate of 150g ai / ha or less, such as 5g ai / ha or less, or 2g ai / ha or less; or at a rate ranging from any of the above minimums to any of the above maximums, such as 1-150g ai / ha, 2-130g ai / ha, 2.5-45g ai / ha, 3-70g ai / ha, 4-147.5g ai / ha, 5-100g ai / ha, 6-75g ai / ha, 7-50g ai / ha, 10-149g ai / ha, 20-120g ai / ha, 25-90g ai / ha, 30-60g ai / ha, 50-150g ai / ha, 60-130g ai / ha, or 100-145g ai / ha.

[0354] Clopyralid In some embodiments, the synthetic auxin herbicide may include clopyralid or an agriculturally acceptable salt or ester thereof. Clopyralid, shown below, is a compound according to Formula I that provides post-emergence control of many annual and perennial broadleaf weeds in sugar beet, fodder beet, rapeseed, corn, cereals, brassicas, onion, chive, strawberry, flax, grassland, and non-cropland. Clopyralid and methods for producing clopyralid are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0355] In some embodiments, clopyralid may be provided as an agriculturally acceptable salt or ester of clopyralid. Exemplary agriculturally acceptable salts and esters of clopyralid include, but are not limited to, clopyralid-methyl, clopyralid-potassium, clopyralid-tris(2-hydroxypropyl)ammonium, and clopyralid-olamine, as shown below. [ka]

[0356] Clopyralid may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, clopyralid is at least 30g ai / ha, at least 35g ai / ha, at least 40g ai / ha, at least 45g ai / ha, at least 50g ai / ha, at least 55g ai / ha, at least 60g ai / ha, at least 65g ai / ha, at least 70g ai / ha, at least 75g ai / ha, at least 80g ai / ha, at least 85g ai / ha, at least 90g ai / ha, at least 95g ai / ha, at least 100g ai / ha, at least 110g ai / ha, at least 120g ai / ha, at least 125g ai / ha, at least 130g ai / ha, at least 140g ai / ha, at least 150g ai / ha, at least 160g ai / ha, at least 170g ai / ha, at least 175g ai / ha, at least 180g ai / ha, at least 190g ai / ha, at least 200g ai / ha, at least 210g ai / ha, at least 220g ai / ha, at least 230g ai / ha, at least 240g ai / ha, at least 250g ai / ha, at least 260g ai / ha, at least 270g ai / ha, at least 280g ai / ha, at least 290g ai / ha, at least 300g ai / ha, at least 310g ai / ha, at least 320g ai / ha, at least 330g ai / ha, at least 340g ai / ha, at least 350g ai / ha, at least 360g ai / ha ai / ha or more, 190g ai / ha or more, 200g ai / ha or more, 210g ai / ha or more, 220g ai / ha or more, 225g ai / ha or more, 230g ai / ha or more, 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more, 270g ai / ha or more, 275g ai / ha or more, 280g ai / ha or more, 290g ai / ha or more, 300g ai / ha or more, 310g ai / ha or more, 320g ai / ha or more, 325g ai / ha or more, 330g ai / ha or more, 340g ai / ha or more, 350g ai / ha or more, 360g ai / ha or more, 370g ai / ha or more, 375g ai / ha or more, 380g ai / ha or more, or at a rate of 25g ai / ha or more, such as 390g ai / ha or more;390g ai / ha or less, 380g ai / ha or less, 375g ai / ha or less, 370g ai / ha or less, 360g ai / ha or less, 350g ai / ha or less, 340g ai / ha or less, 330g ai / ha or less, 325g ai / ha or less, 320g ai / ha or less, 310g ai / ha or less, 300g ai / ha or less, 290g ai / ha or less, 280g ai / ha or less, 275g ai / ha or less, 270g ai / ha or less, 260g ai / ha or less, 250g ai / ha or less, 240g ai / ha or less, 230g ai / ha or less, 225g ai / ha or less, 220g ai / ha or less, 210g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 175g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 125g ai / ha or less, 120g ai / ha or less, 110g ai / ha or less, 100g less than 95g ai / ha, less than 90g ai / ha, less than 85g ai / ha, less than 80g ai / ha, less than 75g ai / ha, less than 70g ai / ha, less than 65g ai / ha, less than 60g ai / ha, or less than 55g ai / ha, less than 50g ai / ha, less than 45g ai / ha, less than 40g ai / ha, 35g less than ai / ha or 30g or applied to vegetation or an area adjacent to vegetation, or to the soil or water, to inhibit the emergence or growth of vegetation in an amount ranging from any of the above minimums to any of the above maximums, such as 25-400g ai / ha, 55-150g ai / ha, 60-310g ai / ha, 65-190g ai / ha, 80-260g ai / ha, 85-300g ai / ha, 100-275g ai / ha, 120-330g ai / ha, 140-390g ai / ha, 150-250g ai / ha, or 30-400g ai / ha;

[0357] Fluroxypyr In some embodiments, the synthetic auxin herbicide may comprise fluroxypyr or its agriculturally acceptable salt or ester.Fluroxypyr, as shown below, is a compound according to Formula I that provides post-emergence control of certain broadleaf weeds in small grain crops, pastures, grasslands, orchards, plantation crops, corn, and forests.Fluroxypyr and methods for producing fluroxypyr are known in the art.Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0358] In some embodiments, fluroxypyr can be provided as an agriculturally acceptable salt or ester of fluroxypyr. Exemplary agriculturally acceptable salts and esters of fluroxypyr include, but are not limited to, fluroxypyr-2-butoxy-1-methylethyl (fluroxypyr-butometyl) and fluroxypyr-meptyl (fluroxypyr-MHE). In some embodiments, fluroxypyr can be provided as fluroxypyr-meptyl (fluroxypyr-MHE), as shown below: [ka]

[0359] Fluroxypyr may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, fluroxypyr is at least 40g ai / ha, at least 45g ai / ha, at least 50g ai / ha, at least 55g ai / ha, at least 60g ai / ha, at least 65g ai / ha, at least 70g ai / ha, at least 75g ai / ha, at least 80g ai / ha, at least 85g ai / ha, at least 90g ai / ha, at least 95g ai / ha, at least 100g ai / ha, at least 110g ai / ha, at least 120g ai / ha, at least 125g ai / ha, at least 130g ai / ha, at least 140g ai / ha, at least 150g ai / ha, at least 160g ai / ha, at least 170g ai / ha, at least 175g ai / ha, at least 180g ai / ha, at least 190g ai / ha, at least 200g ai / ha, ai / ha or more, 210g ai / ha or more, 220g ai / ha or more, 225g ai / ha or more, 230g ai / ha or more, 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more, 270g ai / ha or more, 275g ai / ha or more, 280g ai / ha or more, 290g ai / ha or more, 300g ai / ha or more, 310g ai / ha or more, 320g ai / ha or more, 325g ai / ha or more, 330g ai / ha or more, 340g ai / ha or more, 350g ai / ha or more, 360g ai / ha or more, 370g ai / ha or more, 375g ai / ha or more, 380g 35g such as more than ai / ha or more than 390g ai / ha amounts greater than or equal to ai / ha;390g ai / ha or less, 380g ai / ha or less, 375g ai / ha or less, 370g ai / ha or less, 360g ai / ha or less, 350g ai / ha or less, 340g ai / ha or less, 330g ai / ha or less, 325g ai / ha or less, 320g ai / ha or less, 310g ai / ha or less, 300g ai / ha or less, 290g ai / ha or less, 280g ai / ha or less, 275g ai / ha or less, 270g ai / ha or less, 260g ai / ha or less, 250g ai / ha or less, 240g ai / ha or less, 230g ai / ha or less, 225g ai / ha or less, 220g ai / ha or less, 210g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 175g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 125g ai / ha or less, 120g ai / ha or less, 110g ai / ha or less, 100g ai / ha or less, 95g ai / ha or less, 90g ai / ha or less, 85g ai / ha or less, 80g ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 65g ai / ha or less, 60g ai / ha or less, 55g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, or 35g 400g such as less than ai / ha or applied to vegetation or areas adjacent to vegetation, or to soil or water, to prevent the emergence or growth of vegetation at a rate of 35-400g ai / ha, 55-150g ai / ha, 60-310g ai / ha, 45-190g ai / ha, 80-260g ai / ha, 85-300g ai / ha, 100-275g ai / ha, 120-330g ai / ha, 140-390g ai / ha, 150-250g ai / ha, or 250-400g ai / ha;

[0360] Picloram In some embodiments, the synthetic auxin herbicide may include picloram or an agriculturally acceptable salt or ester thereof. Picloram is a compound according to Formula I that provides undesirable vegetation control in rangelands, grasses, forests, and non-cropland and land use. Picloram and methods for producing picloram are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. [ka]

[0361] In some embodiments, picloram can be provided as an agriculturally acceptable salt or ester of picloram. Exemplary agriculturally acceptable salts and esters of picloram include, but are not limited to, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram-triethylammonium, picloram-triisopropanolammonium (TIPA), picloram-triisopropylammonium, and picloram-trolamine (triethanolammonium). In some embodiments, picloram can be provided as picloram-potassium, as shown below: [ka]

[0362] In some embodiments, picloram can be provided as picloram-TIPA, shown below. [ka]

[0363] Picloram may be applied to vegetation or areas adjacent to vegetation, or to the soil or water, in an amount sufficient to induce a herbicidal effect, to prevent the emergence or growth of vegetation. In some embodiments, picloram is at least 12g ai / ha, at least 14g ai / ha, at least 15g ai / ha, at least 16g ai / ha, at least 18g ai / ha, at least 20g ai / ha, at least 25g ai / ha, at least 30g ai / ha, at least 35g ai / ha, at least 40g ai / ha, at least 45g ai / ha, at least 50g ai / ha, at least 60g ai / ha, at least 70g ai / ha, at least 75g ai / ha, at least 80g ai / ha, at least 90g ai / ha, at least 100g ai / ha, at least 125g ai / ha, at least 150g ai / ha, at least 175g ai / ha, at least 200g ai / ha, at least 225g ai / ha, at least 250g ai / ha, at least 275g ai / ha, at least 300g ai / ha, ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more, 1000g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g amounts of 10g ai / ha or more, such as 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2050g ai / ha or more, 2100g ai / ha or more, 2150g ai / ha or more, 2200g ai / ha or more, or 2220g ai / ha or more;An amount of 22,400 g ai / ha or less, such as 2,220 g ai / ha or less, 2,200 g ai / ha or less, 2,150 g ai / ha or less, 2,100 g ai / ha or less, 2,050 g ai / ha or less, 2,000 g ai / ha or less, 1,900 g ai / ha or less, 1,800 g ai / ha or less, 1,700 g ai / ha or less, 1,600 g ai / ha or less, 1,500 g ai / ha or less, 1,400 g ai / ha or less, 1,300 g ai / ha or less, 1,200 g ai / ha or less, 1,100 g ai / ha or less, 1,000 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...

Claims

1. Compounds according to formula I: 【Chemical 1】 (Wherein X is 【Chemistry 2】 where: R １ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; R ２ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R ３ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R １ and R ２ together to form a substituted double bond, a 3-membered ring, a 4-membered ring, a 5-membered ring, a 6-membered ring, or a 7-membered ring; A is independently O, Si, NR, and S(O) ｍ and A ２ are independently O, N, S(O) ｍ , substituted alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl; Y is independently O, N, or S; Z is independently O, N, S(O) ｍ , substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R ４ R ５ and R ４ and R ５ is independently a substituted amino, alkoxy, alkyl, heteroalkyl, aryl, or heteroaryl; n is 1, 2, or 3; and m is 0, 1, or 2; The compounds exhibit pesticidal activity, provided that the compounds are not 2,4-D isooctyl esters.

2. X is, 【Chemistry 3】 (In the formula, R １ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; and R ２ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ The compound of claim 1, wherein the aryl is heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl.

3. X is, 【Chemistry 4】 (In the formula, R ３ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; A is independently O, Si, NR, and S(O) ｍ , substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R ４ R ５ and R ４ and R ５ is independently a substituted amino, alkoxy, alkyl, heteroalkyl, aryl, heteroaryl; and and m is 0, 1, or 2.

4. X is, 【Chemistry 5】 (In the formula, R ２ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ The compound of claim 1, wherein the aryl is heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl.

5. X is, 【Chemistry 6】 2. The compound of claim 1, wherein:

6. X is, 【Chemistry 7】 (In the formula, A ２ are independently O, N, S(O) ｍ , substituted alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl; Y is independently O, N, or S; Z is independently O, N, S(O) ｍ , substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R ４ R ５ and R ４ and R ５ is independently a substituted amino, alkoxy, alkyl, heteroalkyl, aryl, or heteroaryl; n is 1, 2, or 3; and and m is 0, 1, or 2.

7. The compound has the following formula A1: 【Chemistry 8】 (In the formula, R １ and R ２ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ 3. The compound of claim 2, wherein the aryl group is heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, mono- or di-substituted alkylamino, mono- or di-substituted arylamino, mono- or di-substituted heteroarylamino, alkoxy, arylalkoxy, heteroarylalkoxy, alkylthio, arylthio, or hetearylthio.

8. The compound has the following formula A2: 【Chemistry 9】 (In the formula, R １ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; and R ２ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ The compound according to claim 2, wherein the compound is selected from the group consisting of: heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, and heteroarylthiocarbonyl.

9. The compound has the following formula A3: 【Chemistry 10】 (In the formula, R １ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; and R ２ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ The compound according to claim 2, wherein the compound is selected from the group consisting of: heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, and heteroarylthiocarbonyl.

10. The compound has the following formula A4: 【Chemistry 11】 (In the formula, R １ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl).

11. 3. The compound of claim 2, wherein the compound is selected from the group consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, and A41.

12. The compound has the following formula B1: 【Chemistry 12】 The compound according to claim 6,

13. 7. The compound of claim 6, selected from the group consisting of compounds B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14, and B15.

14. The compound is 【Chemistry 13】 14. The compound of claim 13 selected from the group consisting of:

15. The compound has the following formula C: 【Chemistry 14】 (In the formula, A is independently C; R ２ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ The compound according to claim 5, wherein the compound is selected from the group consisting of: heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, and heteroarylthiocarbonyl.

16. The compound has the following formula D: 【Chemistry 15】 (In the formula, R １ and R ２ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ The compound according to claim 2, wherein the aryl group is heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, alkoxysulfonyl, alkylaminosulfonyl, arylaminosulfonyl, or heteroarylaminosulfonyl.

17. The compound is 【Chemistry 16】 (In the formula, R ３ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ Heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; and A is independently O, Si, or NR １ , S(O)n (n=0, 1, 2), and R ３ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ The compound according to claim 3, wherein the aryl is heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl.

18. The compound is 【Chemistry 17】 (In the formula, R ２ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ The compound of claim 2, wherein the aryl is heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, alkoxysulfonyl, alkylaminosulfonyl, arylaminosulfonyl, or heteroarylaminosulfonyl.

19. The compound is 【Chemistry 18】 17. The compound of claim 16, wherein:

20. 2. The compound of claim 1, wherein the compound is selected from the group consisting of D1, D2, D3, D4, D5, D6, D7, D8, D9, D10, D11, D12, D13, D14, D15, D16, D17, D18, D19, D20, D21, D22, D23, D24, D25, D26, D27, D28, D29, D30, D31, D32, and D33.

21. The compound has the following formula E: 【Chemistry 19】 (In the formula, R ２ are independently hydrogen, C １ ~C １６ Alkyl, C １ ~C １６ Heteroalkyl, C ５ ~C １０ Aryl, C ５ ~C １０ The compound according to claim 4, wherein the compound is selected from the group consisting of: heteroaryl; alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, and heteroarylthiocarbonyl.

22. The compound is 【Chemistry 20】 19. The compound of claim 18 selected from the group consisting of:

23. 10. The compound of claim 1, wherein the compound is a compound listed in Table 1: Pesticidal Compounds.

24. The compound according to any one of claims 1 to 23, wherein the pesticidal activity is a herbicidal activity.

25. 1. A composition comprising: a first herbicide, wherein the first herbicide is a compound according to any one of claims 1 to 24; and A composition comprising a second herbicide.

26. 26. The composition of claim 25, wherein the second herbicide is selected from the group consisting of acetolactate synthase (ALS), acetohydroxyacid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl-CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, glutamine synthase inhibitors, microtubule assembly inhibitors, mitosis inhibitors, very long chain fatty acid (VLCFA) inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, phytoene desaturase (PDS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes of action, and unclassified herbicides.

27. The first herbicide is 【Chemical Formula 21】 26. The composition of claim 25, selected from the group consisting of:

28. 28. The composition of claim 25 or 27, wherein the second herbicide is a protoporphyrinogen oxidase (PPO) inhibitor.

29. 29. The composition of claim 28, wherein the second herbicide is a protoporphyrinogen oxidase (PPO) inhibitor selected from the group consisting of acifluorfen, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, clomethoxyfen, cinidon, fluazolate, flufenpyr, flumiclorac, flumioxazin, fluoroglycofen, fluthiacet, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, saflufenacil, sulfentrazone, thidiazimine, thiafenacil, trifludimoxadine, an agriculturally acceptable salt thereof, or a combination thereof.

30. 28. The composition of claim 25 or 27, wherein the second herbicide is a 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitor selected from the group consisting of benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxaclortol, isoxaflutole, lancotrione, mesotrione, pyraquinate, pyrasulfotole, pyrazolinate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, or an agriculturally acceptable salt or ester thereof, and combinations thereof.

31. 28. The composition of claim 25 or 27, wherein the second herbicide is a synthetic auxin or auxin transport inhibitor selected from the group consisting of synthetic auxin herbicides selected from the group consisting of 2,4-D; 2,4-DB; 2,3,6-TBA, aminocyclopyrachlor, aminopyralid, benazolin-ethyl, chloramben, clomeprop, clopyralid, dichlorprop, dichlorprop-P, dicamba, florpyrauxifen, fluchloraminopyr, fluroxypyr, fluroxypyr-MHE, halauxifen, indoloxypyr, mecoprop, mecoprop-P, MCPA, MCPA-thioethyl, MCPB, picloram, quinclorac, quinmerac, triclopyr, agriculturally acceptable salts and esters thereof, and combinations thereof.

32. 28. The composition of claim 25 or 27, wherein the second herbicide is glyphosate or an agriculturally acceptable salt or ester thereof.

33. 28. The composition of claim 25 or 27, wherein the second herbicide is glufosinate or an agriculturally acceptable salt or ester thereof.

34. 28. The composition of claim 25 or 27, wherein the second herbicide is selected from the group consisting of brocorozone, fluchloraminopyr, flufenoximacil, flusulfinam, icaforin, iptriazopyride, metoproxibicyclon, pyraquinate, and pyriflubenzoxim.

35. The composition of any one of claims 25 to 34, further comprising a safener.

36. 36. The composition of claim 35, wherein the safener is an azole safener.

37. 37. The composition of claim 36, wherein the safener is selected from the group consisting of fenchlorazole, flurazole, furilazole, isoxadifen, mefenpyr, agriculturally acceptable salts or esters thereof, or combinations thereof. In some aspects, azole carboxylate safeners may include fenchlorazole-ethyl, isoxadifen-ethyl, and mefenpyr-diethyl.

38. 38. The composition of any one of claims 1 to 37, wherein the concentration of the active ingredient in the composition is from 0.001 to 98 percent by weight.

39. 40. A method for controlling undesirable vegetation, comprising contacting the vegetation or the locus thereof with a herbicidally effective amount of a compound of any one of claims 1 to 38, or applying a herbicidally effective amount of a compound of any one of the preceding claims to the soil to prevent emergence of the vegetation.

40. 40. The method for controlling undesirable vegetation of claim 39, wherein said compound is applied in an amount of from about 200 grams to about 2,000 grams acid equivalent per hectare (g ae / ha).

41. 41. The method of controlling undesirable vegetation of claim 40, wherein said amount is from about 800 g ae / ha to about 1,200 g ae / ha.

42. 42. A method for controlling undesirable vegetation in crops that have been made tolerant or resistant to 2,4-dichlorophenoxyacetic acid, the method comprising contacting the vegetation or the locus thereof with a herbicidally effective amount of a compound of any one of claims 1 to 41 or applying a herbicidally effective amount of a compound of any one of claims 1 to 41 to the soil to prevent emergence of the vegetation.

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