Herbicidal compositions

Abstract

A herbicidal composition comprising a 2,4-D analogue of formula I and a second compound selected from the group consisting of halauxifen, diclosulam, glyphosate, glufosinate, mesotrione, saflufenacil, sulfentrazone and trifludimoxazin and an agriculturally acceptable salt or ester thereof. A method of controlling undesired vegetation using the composition.

Description

HERBICIDAL COMPOSITIONSFIELD

[0001] Aspects herein include herbicidal compositions and agricultural methods, including herbicidal compositions that are useful in controlling unwanted plants. The herbicides disclosed herein may be used alone, in various formulations, or together with other agriculturally active compounds including other herbicides to control weeds in various crops.

[0002] This disclosure includes (2,4-Dichlorophenoxy)acetic acid analogs. More specifically, this disclosure relates to (2,4-Dichlorophenoxy)acetic acid analogs, such as esters, amides, alkoxyamides, aminooxy esters, linkers, and carbon groups.BACKGROUND

[0003] Protecting crops from undesirable vegetation which adversely affect crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced a variety of chemicals and chemical formulations effective in the control of such unwanted plant growth. Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use. However, there remains a need for compositions and methods that are effective in controlling undesirable vegetation, and which demonstrate other physiochemical characteristics that make them easy to formulate and to apply under varying field conditions.

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

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

[0006] Efforts to solve the volatility problem, including preparation of water-soluble salts such as the dimethylamine salt of 2,4-D, have not been totally satisfactory because, upon volatilization of the amine, the herbicide reverts back to its initial acid form, which, in itself under certain unfavorable conditions, has sufficient volatility to cause damage to sensitive crops.

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

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

[0009] A need therefore exists for alternate forms of 2,4-D that have reduced volatility, reduced spray drift, reduced volatility drift, reduced odor, improved tank-mixability with other pesticidal actives, or improved formulation flexibility.SUMMARY

[0010] Disclosed herein are various compounds according to various details or aspects. Such compounds may include compounds according to Formula I:Formula I

[0011] wherein X is Ci-Cs alkyl.

[0012] Various compositions may include any of the aforementioned compounds, where the concentration of active ingredients in the composition is from 0.001 to 98 percent by weight.

[0013] Such previously described compounds may exhibit a variety of pesticidal activity, such as herbicidal activity.

[0014] Also included herein are methods of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with a herbicidally effective amount of the previously described compounds, or applying to the soil to prevent the emergence of vegetation a herbicidally effective amount of the previously described compounds.

[0015] Methods of controlling undesirable vegetation include methods where disclosed compounds are applied at a rate of between about 200 grams to about 3,000 grams of acid equivalent per hectare (g ae / ha), such as between about 800 g ae / ha to about 1,600 g ae / ha.

[0016] Also included are methods of controlling undesirable vegetation in a crop that has been made tolerant or resistant to 2,4-dichlorophenoxyacetic acid, which comprises contacting the vegetation or the locus thereof with or applying to the soil to prevent the emergence of vegetation, a herbicidally effective amount of a compound according to any one of the compounds disclosed herein.DETAILED DESCRIPTION

[0017] The aspect disclosed below is not intended to be exhaustive or limit the disclosure to the precise form disclosed in the following detailed description. Rather, the aspects are chosen and described so that others skilled in the art may utilize its teachings.

[0018] While various concepts of the present disclosure are illustrated and described in detail in the figures and the description herein, results in the figures and their description are to be considered as exemplary and not restrictive in character; it being understood that only the illustrative aspects are shown and described and that all changes and modifications that come within the spirit of the disclosure are desired to be protected.DEFINITIONS

[0019] Unless defined otherwise, the scientific and technological nomenclatures have the same meaning as commonly understood by a person of ordinary skill in the art pertaining to this disclosure.

[0020] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “about” refers to a range of values plus or minus 10 percent, e.g., about 1.0 encompasses values from 0.9 to 1.1.

[0021] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “agriculturally active” compound includes any compound that may be of benefit to agriculture, including compounds that either alone or in combination with other compounds inhibit the growth of plants deemed undesirable in a given agricultural setting.

[0022] The examples given in the definitions are generally non-exhaustive and must not be construed as limiting the invention disclosed in this document. It is understood that a substituent should comply with chemical bonding rules and steric compatibility constraints in relation to the molecule to which it is attached.

[0023] As used herein, the term “alkanes” may be understood to include straight chain, branched, or cyclic, substituted, or unsubstituted hydrocarbons, which comprise one or more carbon-carbon bonds. Elements and groups that can be used to substitute alkanes include, but are not limited to, groups which include oxygen, nitrogen, sulfur, halogen, or metals, the linkage between the hydrocarbon and the substituent may be via a carbon-carbon bond or through an element other than carbon including, but not limited to, oxygen, nitrogen, and sulfur.

[0024] As used herein, the term “alkenes” may be understood to refer to straight chain, branched, or cyclic substituted or unsubstituted hydrocarbons, which include at least one carboncarbon double bond. Elements and groups that can be used to substitute alkenes include, but arenot limited to, groups which include oxygen, nitrogen, sulfur, halogen, or metals, the linkage between the hydrocarbon and the substituent may be via a carbon-carbon bond or through an element other than carbon including, but not limited to, oxygen, nitrogen, and sulfur.

[0025] As used herein, the term “alkynes” may be understood to include reference to straight chain or branched or cyclic, substituted, or unsubstituted hydrocarbon, which include at least one carbon-carbon triple bond. Elements and groups that can be used to substitute alkynes include, but are not limited to, groups which include oxygen, nitrogen, sulfur, halogen, or metals, the linkage between the hydrocarbon and the substituent may be via a carbon-carbon bond or through an element other than carbon including, but not limited to, oxygen, nitrogen, and sulfur.

[0026] As used herein, the term “halo” may be understood to refer to one or more of the following elements: fluoro, chloro, bromo, and iodo.

[0027] As used herein, the term “aryl” may be understood to refer to any group comprising at least one aromatic ring. The aromatic ring itself may be substituted or unsubstituted.Elements and groups that can be used to substitute aryls include, but are not limited to, groups which include oxygen, nitrogen, sulfur, halogen, or metals. The linkage between the hydrocarbon and the substituent may be via a carbon-carbon bond or through an element other than carbon including, but not limited to, oxygen, nitrogen, and sulfur.

[0028] As used herein, the term “heteroaryl” may be understood to include two aromatic rings which include in the cyclic structure elements other than carbon, such other elements include, but are not limited to, oxygen, nitrogen, sulfur, and the like. Heteroaryl may include more than one ring structure. Heteroaryls may be substituted or unsubstituted, substituents include, but are not limited to, elements and / or groups which include oxygen, nitrogen, sulfur, halogen, or metals, the linkage between the hydrocarbon and the substituent may be via a carbon-carbon bond or through an element other than carbon including, but not limited to, oxygen, nitrogen, and sulfur.

[0029] Exemplary heteroaryls include, but are not limited to, benzofuranyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, benzothienyl, benzothiazolyl, cinnolinyl, furanyl, imidazolyl, indazolyl, indolyl, isoindolyl, isoquinolinyl, isothiaz olyl, isoxazolyl, oxadiazolyl, oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolylpyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl, thienyl, triazinyl, and triazolyl.

[0030] Saturated heterocycles are ring structures which include one or more elements other than carbon, these elements include, but are not limited to, oxygen, nitrogen, sulfur, and the like.Exemplary saturated heterocycles include, but are not limited to, piperazinyl, piperidinyl, morpholinyl, pyrrolidinyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl and tetrahydropyranyl.

[0031] Examples of partially unsaturated hetero cycles include, but are not limited to, 1,2,3,4-tetrahydro quinolinyl, 4.5-dihydro-oxazolyl. 4,5-dihydro-lH-pyrazolyl, 4,5-dihydro- isoxazolyl, and 2,3-dihydro-l,3,4-oxadiazolyl.

[0032] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “alkyl” refers to any of the following: alkanes, alkenes, or alkynes, which are straight chained, branched, or cyclic, substituted, or unsubstituted; substituents may include, but are not limited to, halogens, aminos, iminos, sulfones, sulfoxides, aryls, heteroaryl, esters, ketones, aldehydes, alcohols, acids, and / or esters. Unless explicitly stated otherwise, any compound capable of existing as an isomer, a stereoisomer, or a tautomer may be used in any of its herbicidally active isoforms, configurations, or tautomers.

[0033] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “AMATA” refers to Amaranthus rudis (common waterhemp).

[0034] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “AMBEL” refers to Ambrosia artemisiifolia (common ragweed).

[0035] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “ABUTH” refers to Abutilon theophrasti (velvetleaf).

[0036] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “ERICA” refers to glyphosate resistant Conyza canadensis (L.) (horseweed).

[0037] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “GLXMA” refers to Glycine max (L.) Merr., (soybean).

[0038] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “DCM” refers to dichloromethane.

[0039] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “EtOAC” refers to ethyl acetate.

[0040] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “DMF” refers to dimethyl formamide.

[0041] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “K2CO3” refers to potassium carbonate.

[0042] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “EDC” refers to l-ethyl-3 -(3 -dimethylaminopropyl) carbodiimide.

[0043] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “DMAP” refers to 4-dimethylaminopyridine.

[0044] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “DIPEA” refers to A A-diisopropylethylamine.

[0045] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “EtsN” refers to triethylamine.

[0046] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “HPLC” refers to high-performance liquid chromatography.

[0047] As used herein, unless explicitly stated otherwise or clearly implied otherwise, the term “LC-MS” refers to liquid chromatography coupled with mass spectrometry.

[0048] 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 (for example, it includes at least the degree of error associated with the 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 “from about 2 to about 4” also discloses the range “from 2 to 4.”

[0049] As used herein, the terms “pesticide”, “pesticidal”, and “pesticidal activity” refer to substances, compounds, agents, and activities that control pests, such as unwanted or harmful insects, vegetation, fungi, bacteria, micro-organisms, nematodes, mites, arthropods, and the like.

[0050] As previously stated, this disclosure includes (2,4-Dichlorophenoxy)acetic acid analogs. More specifically, this disclosure relates to (2,4-Dichlorophenoxy)acetic acid analogs (“2,4-D analogs”), such as esters, linkers, and carbon groups.

[0051] Without being limited to any theory, it is believed that various 2,4-D analogs can have improved properties prior to or during application. Then, in the soil or in-planta, the 2,4-D analog can be broken into the active form of 2,4-D acid. Thus, various 2,4-D analogs disclosed herein can benefit from the aforementioned improved properties and yet have an acceptable pesticidal profile.

[0052] Disclosed herein are 2,4-D analogs that can be converted into 2,4-D during or after application. For example, disclosed herein are pesticidal compositions of Formula (I):Formula I

[0053] wherein X is Ci-Cs alkyl.

[0054] Aspects may include Compound 1 :Compound 1

[0055] Aspects may include Compound 2:Compound 2

[0056] Aspects may include Compound 3 :Compound 3

[0057] As used herein, herbicide means a compound, e.g., an active ingredient, that kills, controls, or otherwise adversely affects the survival, growth and / or reproduction of plants.

[0058] As used herein, a herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect to the vegetation e.g., causing deviations from natural development, killing, effecting regulation, causing desiccation, causing retardation, and the like.

[0059] As used herein, controlling undesirable vegetation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and vegetation. Described herein are methods of controlling undesirable vegetation through the application of certain herbicide combinations or compositions. Methods of application include, but are not limited to,applications to the vegetation or locus thereof, e.g., application to the area adjacent to the vegetation, as well as preemergence, postemergence, foliar (broadcast, directed, banded, spot, mechanical, over-the-top, or rescue), and in-water applications (emerged and submerged vegetation, broadcast, spot, mechanical, water-injected, granular broadcast, granular spot, shaker bottle, or stream spray) via hand, backpack, machine, tractor, or aerial (airplane and helicopter) application methods.

[0060] As used herein, plants and vegetation include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.

[0061] As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted in plants, water, or soil to the referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.

[0062] Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium, and ammonium cations of the formula:

[0063] Herbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the locus of the plant at any stage of growth. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted to promote nonselective or selective herbicidal action. In some aspects, the compositions described herein are applied as a post-emergence application, pre-emergence application, or in-water application to flooded paddy rice or water bodies (e.g., ponds, lakes, and streams), to relatively immature undesirable vegetation to achieve the maximum control of weeds.

[0064] In some aspects, the compositions and methods provided herein are utilized to control weeds in crops, including but not limited to direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn / maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallow-land, turf,tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (JVM) and rights of way (ROW).

[0065] With respect to the methods, in certain aspects, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation or a composition described herein. In some aspects, the composition is applied at an application rate sufficient to control, inhibit, or promote the growth of at least one plant. In some aspects the compound is applied, based on the total amount of active ingredients in the composition, in at least one of the following ranges: of from about 200 grams to about 2,000 grams of acid equivalent per hectare (g ae / ha); in some aspects the composition is applied at an application rate of between about 400 grams to about 1,500 grams g ae / ha; in some aspects composition is applied at an application rate of between about 560 grams to about 1,200 grams g ae / ha; composition is applied at an application rate of between about 800 gram to about 1,120 grams g ae / h. In some aspects, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation.

[0066] In some aspects, the compositions and methods provided herein control undesirable vegetation while also reducing problems associated with auxin herbicides such as 2,4-D.Compounds and compositions of Formula I can exhibit reduced spray drift, lower volatility, and improved crop safety compared to 2,4-D. Because the physical properties of compounds of Formula I differ from for example, 2,4-D acid, compositions with superior leaf and stem adhesion, leaf and stem penetration, internal plant translocation, and plant metabolism can be developed. Compounds and compositions of Formula I can also exhibit improved soil adhesion, soil translocation, and soil degradation properties compared to auxin herbicides such as 2,4-D.

[0067] The compositions and methods provided herein are utilized to control undesirable vegetation. Undesirable vegetation includes, but is not limited to, undesirable vegetation that occurs in rice, cereals, wheat, barley, oats, rye, pastures, grasslands, rangelands, fallow-land, row crops (e.g., com / maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton), turf, trees and vine orchards, plantation crops, vegetables, ornamental species, aquatic or noncrop settings (e.g., rights-of-way, industrial vegetation management).

[0068] In some aspects, the methods provided herein are utilized to control undesirable vegetation in rice. In certain aspects, the undesirable vegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Echinochloa species (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (bamyardgrass, ECHCG), Echinochloa crus-pavonis(Kunth) Schult, (gulf cockspur, ECHCV), Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice barnyardgrass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon sprangletop, LEFPA), Oryza species (red and weedy rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (itchgrass, ROOEX), Cyperus species (CYPSS), Cyperus difformis L. (smallflower flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Cyperus serotinus Rottb. / C.B. Clarke (tidalmarsh flatsedge, CYPSE), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb. (Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA), Schoenoplectus mucronatus L. (ricefield bulrush, SCPMU), Aeschynomene species, (jointvetch, AESSS), Alternanthera philoxeroides (Mart.) Griseb.(alligatorweed, ALRPH), Alisma plantago-aquatica L. (common waterplantain, ALSPA), Amaranthus species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelina benghalensis L. (Benghal dayflower, COMBE), Eclipta alba (L.) Hassk. (American false daisy, ECLAL), Heteranthera limosa (SW.) Willd. / Vahl (ducksalad, HETLI), Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE), Ipomoea species (momingglories, IPOSS), Ipomoea hederacea (L.) Jacq. (ivy leaf morningglory, IPOHE), Lindemia dubia (L.) Pennell (low false pimpernel, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastern primrose-willow, LUDLI), Ludwigia octovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC), Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria, MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb, POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf.)Cory / Ry db. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).

[0069] In some aspects, the methods provided herein are utilized to control undesirable vegetation in cereals. In certain aspects, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila (Poir.) Roemer & J. A. Schultes (yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthus retroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureum L. (purple deadnettle , LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT), Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Sinapis species (SINSS), Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L.) Vill. (common chickweed, STEME), Veronica persica Poir. (Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).

[0070] In some aspects, the methods provided herein are utilized to control undesirable vegetation in range and pasture, fallow land, IVM, and ROW. In certain aspects, the undesirable vegetation is Ambrosia artemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L. / Tom. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhorn plantain, PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).

[0071] 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, theundesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (Surinam grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R.D. (beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southern sandbur, CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (bamyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Eleusine indica (L.) Gaertn. (goosegrass, ELEIN), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild-proso millet, PANMI), Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilon theophrasti Medik.(velvetleaf, ABUTH), Amaranthus species (pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL), Ambrosia psilostachya DC. (western ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Anoda cristata (L.) Schlecht. (spurred anoda, ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidens pilosa L. (hairy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (broadleaf buttonweed, BOILF), Spermacose latifolia (broadleaved button weed, BOILF), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE), Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge, EPHHI), Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy fleabane, ERIBO), Erigeron canadensis L. (Canadian fleabane, ERICA), Conyza sumatrensis (Retz.) E. H. Walker (tall fleabane, ERIFL), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (smallflower momingglory, IAQTA), Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (white morningglory, IPOLA), Lactuca serriola L. / Tom. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia species (pusley, RCHSS), Sidaspecies (sida, SIDSS), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridax procumbens L. (coat buttons, TRQPR) or Xanthium strumarium L. (common cocklebur, XANST).

[0072] In some aspects, the methods provided herein are utilized to control undesirable vegetation in turf. In certain aspects, the undesirable vegetation is Bellis perennis L. (English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Diodia virginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata L. (dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamium amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L. (broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhorn / narrowleaf plantain, PLALA), Phyllanthus urinaria L. (chamberbitter, PYLTE), Rumex obtusifolius L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Viola species (wild violet, VIOSS).

[0073] 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.

[0074] In some aspects, the combination of a compound of Formula (I) or formulation hereof may be used to control Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus rudis Sauer, (common waterhemp, AMATA), Chenopodium album L. (common lambsquarters, CHEAL), Polygonum convolvulus L. (wild buckwheat, POLCO) and Sinapis arvensis L. (wild mustard, SINAR).

[0075] The compounds of Formula (I) or agriculturally acceptable formulation of the same may be used to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, and sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase(ACCase) inhibitors, (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins (e.g., benzoic acids, phenoxy carboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors (e.g., bipyridyliums), 5 -enolpyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, bialafos), microtubule assembly inhibitors (e.g., benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (e.g., carbamates), very long chain fatty acid (VLCFA) inhibitors (e.g., acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid synthesis inhibitors (e.g., phosphorodithioates, thiocarbamates, benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (e.g., diphenylethers, N- phenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS) inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (e.g., calli stem ones, isoxazoles, pyrazoles, triketones), cellulose biosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes-of-action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endothall, and organoarsenicals. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple herbicide modes-of-action, and biotypes with multiple resistance or tolerance mechanisms (e.g., target site resistance or metabolic resistance).

[0076] With respect to the methods for treating crop fields to reduce or eliminate the growth of unwanted plants, these methods may comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation or a composition described herein. In some aspects, the composition is applied at an application rate of from about 1 gram of acid equivalent per hectare (g ae / ha) to about 3000 grams active ingredient per hectare (gai / ha) based on the total amount of active ingredients in the composition. In certain aspects, the composition is applied at an application rate of from about 4 grams acid equivalent per hectare (g ae / ha) to about 400 g ae / ha based on the total amount of active ingredients in the composition.

[0077] With respect to the methods, in certain aspects, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergenceor growth of vegetation or a composition described herein. In some aspects, the composition is applied at an application rate sufficient to control, inhibit, or promote the growth of at least one plant. In some aspects the compound is applied, based on the total amount of active ingredients in the composition, in at least one of the following ranges: of from: about 1 gram to about 3,000 grams of acid equivalent per hectare (g ae / ha); in some aspects the composition is applied at an application rate of between about 1 gram to about 2000 grams g ae / ha; in some aspects the composition is applied at an application rate of between about 1 gram to about 1000 grams g ae / ha; in some aspects the composition is applied at an application rate of between about 1 gram to about 500 grams g ae / ha; in some aspects composition is applied at an application rate of between about 1 gram to about 250 grams g ae / ha; composition is applied at an application rate of between about 1 gram to about 140 grams g ae / h; in some aspects the composition is applied at an application rate of between about 1 gram to about 70 grams g ae / ha. In some aspects, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation.

[0078] In some aspects, the concentration of the active ingredients in the compositions described herein is from about 0.0005 to 98 percent by weight. In some aspects, the concentration is from about 0.0006 to 90 percent by weight. In compositions designed to be employed as concentrates, the active ingredients, in certain aspects, are present in a concentration from about 0.1 to 98 weight percent, and in certain aspects about 0.5 to 90 weight percent. Such compositions are, in certain aspects, diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds contain, in certain aspects, about 0.0006 to 3.0 weight percent active ingredient and in certain aspects contain about 0.01 to 1.0 weight percent.

[0079] The present compositions can be applied to weeds or their locus by almost any conventional means of application, including but not limited to the use of aerial dusters, sprayers, and granule applicators. Under some circumstances these compounds and formulations thereof may be added to irrigation or paddy water, which is then used to treat plants, soil, and other surfaces.

[0080] The described aspects and following examples are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations with respect to the compositions described herein will be apparent to a person of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.

[0081] Exemplary molecules within the aforementioned formulas according to various aspects may include any of the compounds exemplified herein.EXAMPLES

[0082] The following exemplary organic synthesis routes may be used to create some of the various compounds disclosed herein. While a person of ordinary skill will appreciate these exemplary organic synthesis routes, it is within the knowledge of one skilled in the art — with the benefit of the present disclosure — to utilize these routes as well as affect other organic synthesis routes whether or not explicitly described herein. Thus, the present disclosure would not be seen as limiting to one of ordinary skill and, after reading the present description, it may be apparent to one skilled in the relevant art(s) how synthesize various compounds described herein with alternate organic synthesis routes.

[0083] Furthermore, many of the inputs for the synthesis routes are commercially available. Thus, in some examples, the CAS Number is included for select inputs above the intermediate, for example, sometimes when commercially available.SCHEME 1EXAMPLE 1 Benzyl 2-(2,4-dichlorophenoxy)acetate

[0084] (Bromomethyl)benzene (0.46 g, 2.71 mmol) in DMF (5 mL) was added to a mixture of K2CO3 in DMF (10 mL) at RT and stirred for 10 min. The mixture was cooled to 0 °C, then 2,4-dichlorophenoxyacetic acid (0.5 g, 2.26 mmol) was added under an argon atmosphere and stirred at room temperature for 16 h. Upon completion of the reaction, water (50mL) was added and the mixture extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo which gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc: hexane) gave the title compound as an off-white solid (0.33 g, 47 %). 'H NMR(400MHz, CDC13): 8 7.38 (d, J = 2.5 Hz, 1H), 7.29 (m, 5H), 7.11 (dd, J = 8.8, 2.5 Hz, 1H), 6.73 (d, J = 8.8 Hz, 1H), 5.23 (s, 2H), 4.72 (s, 2H). LCMS: m / z= 333.0.1 [M+Na]+.SCHEME 2EXAMPLE 2 - Compound 3: 2-(2,4-Dichlorophenoxy)acetyl chloride

[0085] 2, 4-Di chlorophenoxyacetic acid (100 g, 0.452 mol) was dissolved in SOCh (340 mL), and the reaction mixture was heated at 80 °C for 4h. Completion of reaction was monitored by HPLC. Upon completion of the reaction, excess SOCh was removed in vacuo which gave the title compound as a pale-yellow oil (98.5 g, 90 %). 'H NMR (400 MHz, CDCI3): 6 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.EXAMPLE 3 (2-(2,4-Dichlorophenoxy)acetoxy)methyl benzoate

[0086] To a solution of 2,4-dichlorophenoxyacetic acid (1 g, 4.52mmol) in toluene (25 mL) was added Ag2CC>3 (3.74g, 13.56 mmol) and chloromethyl benzoate (2.31 g, 13.56 mmol) at RT. The mixture was stirred for 10 min at RT and was then heated to 80 °C for 5 h. Upon completion of the reaction, the mixture was concentrated in vacuo which gave the crude product.Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc: hexane) gave the title compound as a white solid (1 g, 63 %).1H NMR (400MHz, DMSO-d6): 6 7.95 (m, 2H), 7.68 (m, 1H), 7.53 (m, 3H), 7.29 (dd, J = 8.9, 2.6 Hz, 1H), 7.14 (d, J = 8.9 Hz, 1H), 6.05 (s, 2H), 5.08 (s, 2H). LCMS: m / z= 376.97 [M+Na]+.EXAMPLE 4 Methylene bis(2-(2,4-dichlorophenoxy)acetate)

[0087] To a solution of 2,4-dichlorophenoxyacetic acid (0.44 g, 2 mmol) in 1 : 1 DMSO: DCM (14 mL) was added K2CO3 (0.28 g, 4 mmol) and the mixture stirred for 15 min at RT. The reaction mixture was then sealed and heated to 130 °C for 5 h. Upon completion of the reaction, water (50mL) was added; the solid obtained was collected by filtration under suction and pulled dry which gave the title compound as a white solid (1 g, 33 %).1H NMR (400 MHz, DMSO-d6): 5 7.62 (dd, J = 2.6, 1.2 Hz, 1H), 7.35 (dd, J = 8.8, 2.6 Hz, 1H), 7.14 (d, J = 9.0 Hz, 1H), 5.86 (s, 1H), 5.04 (s, 2H). LCMS: m / z= 476.89 [M+Na]+.EXAMPLE 5 1,4-Phenylenebis(methylene) bis(2-(2,4-dichlorophenoxy)acetate)

[0088] 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 stirred for 10 min at RT. The mixture was cooled to 0 °C, then a,a’-dibromo-p-xylene (0.6 g, 2.26 mmol) was added under an argon atmosphere and stirred at RT for 16 h. Upon completion of the reaction, water (100 mL) was added, and the mixture extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with brine, dried over ISfeSCU, filtered and concentrated in vacuo which gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc: hexane) gave the title compound as a white solid (0.5 g, 42 %).JH NMR (400 MHz, DMSO-d6): 5 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.SCHEME 3EXAMPLE 62-(2-(2,4-Dichlorophenoxy)acetoxy)-A, N, A-trimethylethanaminium chloride

[0089] To a solution of 2-hydroxy-A, N, A-trimethylethanaminium chloride (1.46 g, 10.44 mmol) in CHCh (20 mL) was added a solution of 2,4-dichlorophenoxyacetic 2,4- di chlorophenoxyacetyl chloride 3 (2.5 g, 10.44 mmol) in CHCI3 (5 mL). The reaction mixture was heated at 45 °C for 16 h. Upon completion of the reaction, the RM was concentrated in vacuo which gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc: hexane) gave the title compound as a white solid (0.7 g, 37 %). ‘H NMR (400MHz, DMSO-d6): 5 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.EXAMPLE 7 Oxybis(ethane-2,l-diyl) bis(2-(2,4-dichlorophenoxy)acetate)

[0090] 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 g, 15.84 mmol) in DCM (15 mL) was added HATU (6.02 g, 15.84 mmol) and the resultant mixture stirred at RT for 16 h. Upon completion of the reaction, the RM was concentrated in vacuo which gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-15% EtOAc: hexane) gave the title compound as an orange oil (0.4 g, 35 %). *HNMR (400MHz, DMSO-d6): 5 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.Example 8 - Pentane-l,5-diyl bis(2-(2,4-dichlorophenoxy)acetate)

[0091] To a solution of 2-(2,4-dichlorophenoxy)acetic acid (166.6 g, 754 mmol), DMAP (92.0 g, 754 mmol) and pentane-l,5-diol (39.3 g, 377 mmol) in DCM (2 L) was added EDCI (144.8 g, 754 mmol) portion wise at 25 °C while stirring, the reaction mixture was stirred at RT for 24 h. The mixture was quenched with water, washed with 5% citric acid (1000 mL) for 3 times, then the organic layers were washed with brine and filtered, dried with Na2SO4, and concentrated to get a residue. The crude residue was purified by column chromatography (PE: EA = 3 :2) to obtain the title compound (107 g, 56 %) as a white solid.JH NMR (400 MHz, CDC13) 8 7.39 (d, J= 2.5 Hz, 2H), 7.17 (dd, J= 8.8, 2.5 Hz, 2H), 6.78 (d, J= 8.8 Hz, 2H), 4.69 (s, 4H), 4.19 (t, J= 6.5 Hz, 4H), 1.71 - 1.61 (m, 4H), 1.40 - 1.30 (m, 2H).13C NMR (101 MHz, CDCI3) 6 168.14, 152.40, 130.37, 127.57, 127.14, 124.28, 114.70, 66.41, 65.20, 28.05, 22.22. ESIMS m / z 533 ([M+Na]+). Mp, 54-55 °C.EVALUATION OF PESTICIDAL ACTIVITY

[0092] As previously discussed, the compounds and mixtures disclosed herein exhibit varying pesticidal activity. For example, pesticidal activity may include herbicidal activity. Exemplified below in Tables 2 - 8 is select herbicidal activity for some compounds and mixtures on various weeds and crops.

[0093] The following examples applied were technical grades, including control 2,4-D Isooctyl ester (CAS 25168-26-7), except for the 2,4-D choline, which was applied as the commercially available 2,4-D choline from Corteva Agriscience LLC under the tradename ENLIST ONE®. The technical grade materials were dissolved first in a 3 ml solvent mixture of 97.3% acetone: dimethyl sulfoxide (DMSO) and then diluted with a 17 ml solvent mixture of acetone, water, isopropyl alcohol, DMSO, Agri-Dex® crop oil concentrate (a heavy range, paraffin-based petroleum oil and nonionic emulsifiers 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 mix sizes were 20 ml.POSTEMERGENCE APPLICATION METHODS FOR HERBICIDE EVALUATIONS

[0094] Plants were grown in a soil media 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 proprietary amounts of limestone, starter fertilizer, and wetting agent. Profile Greens Grade is a sand-sized granule formed from calcining illite and montmorillonite clay. Several seeds of each species were planted in 10 cm square pots and top watered twice daily. Plant material was propagated in a warm greenhouse with temperature ranging from 25 to 28° C and 50 to 60% relative humidity at the Corteva Global Headquarters (Indianapolis, Indiana, USA). Natural light was supplemented with 1000-watt metal halide overhead lamps with an average illumination of 500 pE nr2s'1photosynthetic active radiation for 16 consecutive hours each day. Plants were top-watered prior to herbicide application and sub-watered after herbicide application.

[0095] Appropriate amounts of test materials were weighed out into glass vials in their technical form to deliver either 280, 375, 560, or 1120 g acid equivalent (ae) / ha. The samples were dissolved in 3 ml of Solvent 1. Solvent 1 is 97% acetone and 3% dimethyl sulfoxide and serves as a general-purpose solvent (GPS) for dissolving technical materials. If samples did not readily dissolve, the sample bottles were placed in hot water and sonicated for 20 minutes. This typically resulted in the test material being thoroughly dissolved. 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 contains acetone, water, isopropyl alcohol, DMSO, Agri-Dex® crop oil concentrate (a heavy range, paraffin-based petroleum oil and nonionic emulsifiers 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 on a volume basis. 2,4-D choline as applied from the commercially available 2,4-D choline from Corteva Agriscience LLC under the tradename ENLIST ONE® and diluted with solvent 2 to compare all materials in the same spray solution.

[0096] Herbicide applications were made to 2 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 fitted with an 8003E nozzle from Spray Systems Company (North Avenue and Schmale Road, P.O. Box 7900, Wheaton, IL 60187), and used a spray pressure of 276 kPa pressure and a speed of 3.1 km / h. The nozzle height was 46 cm above the plant canopy. The experimental design used for the trials was a randomized complete block with 2 replications per treatment. After application, plants were placed on carts according to the randomization and returned to the greenhouse. Plants were sub-watered after treatment with Indianapolis city water or fertilized three times aweek with a commercial fertilizer solution (Jack’s Professional 15-5-15 4 Ca 2Mg fertilizer (manufactured by JR PETERS INC., 6656 Grant Way, Allentown, PA 18106; www.jrpeters.com). Percent visual control assessments were made on a scale of 0 to 100% (where 0 was no control and 100 was complete plant death) at 7, 14, and 21 days after treatment. Measuring the effect of representative experimental compounds on the growth of Amaranthus rudis.

[0097] In conformity with the methods outlined above in Postemergence Application Methods for Herbicide Evaluations, the effect of representative experimental compounds on the growth of Amaranthus rudis (A ATA), common name tall water hemp, was determined at 2 different levels (respectively, 375, 560, and 1120 g acid equivalent (ae) / ha) of the experimental actives tested. Plants were treated with one of the compounds, a control plant was not treated. Twenty-one days after treatment, the plants were measured. The data is present as a percent reduction in plant size relative to the untreated control. Referring now to Tables 2 - 8, some of the compounds and mixtures tested demonstrated a significant effect on the growth of this common species of weed.Measuring the effect of representative experimental compounds on the growth of Ambrosia artemisiifolia

[0098] In conformity with the methods outlined above in Postemergence Application Methods for Herbicide Evaluations, the effect of representative experimental compounds on the growth of Ambrosia artemisiifolia (AMBEL), (common ragweed), was determined at 2 different levels (respectively, 375, 560, and 1120 g acid equivalent (ae) / ha) of the experimental actives tested. Plants were treated with one of the compounds, a control plant was not treated. Twenty- one days after treatment, the plants were measured. The data is present as a percent reduction in plant size relative to the untreated control. Referring now to Tables 2 - 8, some of the compounds tested demonstrated a significant effect on the growth of this common species of weed.Measuring the effect of representative experimental compounds on the growth of Abutilon theophrasti

[0099] In conformity with the methods outlined above in Postemergence Application Methods for Herbicide Evaluations, the effect of representative experimental compounds on the growth of Abutilon theophrasti (ABUTH), common name velvetleaf, was determined at 2 different levels (respectively, 375, 560, and 1120 g acid equivalent (ae) / ha) of the experimental actives tested. Plants were treated with one of the compounds, a control plant was not treated.Twenty-one days after treatment, the plants were measured. The data is present as a percent reduction in plant size relative to the untreated control. Referring now to Tables 2 - 8, some of the compounds tested demonstrated a significant effect on the growth of this common species of weed.Measuring the effect of representative experimental compounds on the growth of Chenopodium album

[0100] In conformity with the methods outlined above in Postemergence Application Methods for Herbicide Evaluations, the effect of representative experimental compounds on the growth of Chenopodium album (CHEAL), common name, common lambsquarters, was determined at 2 different levels (respectively, 375, 560, and 1120 g acid equivalent (ae) / ha) of the experimental actives tested. Plants were treated with one of the compounds, a control plant was not treated. Twenty-one days after treatment, the plants were measured. The data is present as a percent reduction in plant size relative to the untreated control. Referring now to Tables 2 - 8, some of the compounds tested demonstrated a significant effect on the growth of this common species of weed.Measuring the effect of representative experimental compounds on the growth of Conyza canadensis (L.)

[0101] In conformity with the methods outlined above in Postemergence Application Methods for Herbicide Evaluations, the effect of representative experimental compounds on the growth of Conyza canadensis (L.), (ERICA), common name, Horseweed, was determined at 2 different levels (respectively, 375, 560, and 1120 g acid equivalent (ae) / ha) of the experimental actives tested. Plants were treated with one of the compounds, a control plant was not treated. Twenty-one days after treatment, the plants were measured. The data is present as a percent reduction in plant size relative to the untreated control. Referring now to Tables 2 - 8, some of the compounds tested demonstrated a significant effect on the growth of this common species of weed.Measuring the effect of representative experimental compounds on the growth of Glycine max

[0102] In conformity with the methods outlined above in Postemergence Application Methods for Herbicide Evaluations, the effect of representative experimental compounds on the growth of Glycine max (Enlist E3® traited soybeans commercially available from Corteva Agriscience®) was determined at different levels (respectively, 375, 560, and 1120 g acid equivalent (ae) / ha) of the experimental actives tested. Plants were treated with one of thecompounds, a control plant was not treated. Twenty-one days after treatment, the plants were measured. The data is present as a percent reduction in plant size relative to the untreated control.FORMULATIONS

[0103] The present disclosure also includes formulations of the compositions and methods disclosed herein.Additives

[0104] The compositions and methods disclosed herein can also be mixed with or applied with an additive. In some aspects, the additive is added sequentially. In some aspects, the additive is added simultaneously. In some aspects, the additive is premixed with the compounds according to Formula I. In some aspects, the additive is premixed with a safener or agriculturally acceptable salt or ester thereof.OTHER PESTICIDES

[0105] Some aspects of the disclosed safened compositions disclosed include adding one or more additional pesticide active ingredients to the safened compositions. These pesticide active ingredients may include one or more of an herbicide, an insecticide, a fungicide, a nematocide, a miticide, a arthropodicide, a bactericide, a plant growth regulator, or combinations thereof that are compatible with the compositions of the present disclosure.

[0106] In some aspects, the additive is an additional herbicide. For example, the compositions described herein can be applied in conjunction with one or more additional herbicides to control undesirable vegetation. The composition can be formulated with one or more additional herbicides, tank mixed with the one or more additional herbicides, or applied sequentially with the one or more additional herbicides, such as the exemplary herbicides described below.Triazolopyrimidine Sulfonamide Herbicides

[0107] In some aspects, the composition contains a herbicidally effective amount of compounds according to Formula I , and (b) florasulam, cloransulam, diclosulam, flumetsulam, metosulam, penoxsulam, or pyroxsulam, or agriculturally acceptable salts or esters thereof.Diclosulam

[0108] Compositions and methods of the present disclosure can include diclosulam or an agriculturally acceptable salt or ester thereof. Diclosulam, shown below, is a triazolopyrimidine sulfonamide that provides broad-spectrum control of many broadleaf weeds in soybeans and peanuts. Diclosulam, as well as methods of preparing diclosulam, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.

[0109] Diclosulam can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, diclosulam is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2.18 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, 31g 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; in an amount of 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 in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 2.18-35 g ai / ha, 2.5-34 g ai / ha, 2.75-22 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.ARYL PICOLINATES

[0110] In some aspects, the composition contains compounds according to Formula I, and (b) florpyrauxifen, halauxifen, or agriculturally acceptable salts or esters thereof.Halauxifen

[0111] In some aspects, the synthetic auxin herbicide can comprise halauxifen or an agriculturally acceptable salt or ester thereof. Halauxifen, shown below, is an aryl picolinic acid herbicide that provides broad-spectrum control of broad-leaved weeds in cereal crops.

[0112] In some aspects, halauxifen can be provided as an agriculturally acceptable salt or ester of halauxifen. Exemplary agriculturally acceptable salts and esters of halauxifen include, but are not limited to, halauxifen-methyl. In some aspects, the halauxifen is provided as

[0113] Halauxifen can be applied to vegetation or an area adj acent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, halauxifen is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai / ha or more, such as 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 / haor more, 145 g ai / ha or more, 147.5 g ai / ha or more, or 149 g ai / ha or more; in an amount of 150 g ai / ha or less, such as 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, 2.5 g ai / ha or less, or 2 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 1-150 g ai / ha, 2-130 g ai / ha, 2.5-45 g ai / ha, 3-70 g ai / ha, 4-147.5 g ai / ha, 5-100 g ai / ha, 6-75 g ai / ha, 7-50 g ai / ha, 10-149 g ai / ha, 20-120 g ai / ha, 25-90 g ai / ha, 30-60 g ai / ha, 50-150 g ai / ha, 60-130 g ai / ha, or 100-145 g ai / ha.Saflufenacil

[0114] Compositions and methods of the present disclosure can include saflufenacil or an agriculturally acceptable salt or ester thereof. Saflufenacil, as well as methods of preparing saflufenacil, are known in the art. Saflufenacil, shown below, is 2-chloro-5-[3,6-dihydro-3- methyl-2,6-dioxo-4-(trifluoromethyl)-l(2J7)-pyrimidinyl]-4-fluoro-7V-[[methyl(l -methylethyl)- amino] sulfonyl]benzamide. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of saflufenacil include: pre-emergence control of broadleaf weeds in maize and sorghum; pre-plant foliar burn-down in soybeans, cereals, cotton, and legumes; and post-directed foliar bum-down in tree fruit and nuts.

[0115] Saflufenacil can be applied to the foliage or roots of undesirable vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, saflufenacil is applied to the foliage or roots of undesirable vegetation in an amount of 0.5 g ai / ha or more, such as 0.6 g ai / ha or more, 0.8 g ai / ha or more, 1 g ai / ha or more, 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, 20 g ai / ha or more, 22.5 g ai / ha or more, 25g ai / ha or more, 27.5 g ai / ha or more, 30 g ai / ha or more, 32.5 g ai / ha or more, 35 g ai / ha or more, 37.5 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, or 75 g ai / ha or more; in an amount of 80g ai / ha or less, such as 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, 37.5 g ai / ha or less, 35 g ai / ha or less, 32.5 g ai / ha or less, 30 g ai / ha or less, 27.5 g ai / ha or less, 25 g ai / ha or less, 22.5 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 g ai / ha or less, 1 g ai / ha or less, 0.8 g ai / ha or less, or 0.6 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 0.5-80 g ai / ha, 30-75 g ai / ha, 6-70 g ai / ha, 10-65 g ai / ha, 20-50 g ai / ha, 15-80 g ai / ha, 3-45 g ai / ha, 12.5-37.5 g ai / ha, 7-35 g ai / ha, 9-32.5 g ai / ha, 1-25 g ai / ha, 8-65 g ai / ha, 4-22.5 g ai / ha, 0.5-20 g ai / ha, 0.8-17.5 g ai / ha, 22.5-55 g ai / ha, 10-40 g ai / ha, 0.5-5 g ai / ha, or 0.6-75 g ai / ha.Sulfentrazone

[0116] Compositions and methods of the present disclosure can include sulfentrazone or an agriculturally acceptable salt or ester thereof. Sulfentrazone, as well as methods of preparing sulfentrazone, are known in the art. Sulfentrazone, shown below, is 7V-[2,4-dichloro-5-[4- (difluoromethyl)-4,5-dihydro-3-methyl-5-oxo- 177-1, 2, 4-tri azol- l-yl]phenyl]-methane- sulfonamide. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of sulfentrazone include its use for pre-plant incorporated or pre-emergence control of annual broadleaf weeds, some grass weeds, and Cyperus spp. in soybeans, sugar cane, and tobacco.

[0117] Sulfentrazone can be applied to the foliage and roots of undesirable vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, sulfentrazone is applied to the foliage and roots of undesirable vegetation in an amount of 100 g ai / ha or more, such as 110 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 175 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 210 g ai / ha or more, 220 g ai / ha or more, 225 g ai / ha or more, 230 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 270 g ai / ha or more, 275 g ai / ha or more, 280 g ai / ha or more, 290 g ai / ha or more, 300 g ai / ha or more, 320 g ai / ha or more, 340 g ai / ha or more, 350g ai / ha or more, 360 g ai / ha or more, 380 g ai / ha or more, 400 g ai / ha or more, 425 g ai / ha or more, 450 g ai / ha or more, or 475 g ai / ha ormore; in an amount of 500 g ai / ha or less, such as 475 g ai / ha or less, 450 g ai / ha or less, 425 g ai / ha or less, 400 g ai / ha or less, 380 g ai / ha or less, 375 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 325 g ai / ha or less, 320 g ai / ha or less, 300 g ai / ha or less, 290 g ai / ha or less, 280 g ai / ha or less, 275 g ai / ha or less, 270 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 230 g ai / ha or less, 225 g ai / ha or less, 220 g ai / ha or less, 210 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 175 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, or 100 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 100-500 g ai / ha, 250-400 g ai / ha, 120-210 g ai / ha, 375-500 g ai / ha, 200-475 g ai / ha, 360-450 g ai / ha, 120-250 g ai / ha, 110-380 g ai / ha, 125-375 g ai / ha, 170-350 g ai / ha, 220-425 g ai / ha, 150-300 g ai / ha, 120-275 g ai / ha, 160-250 g ai / ha, 280-450 g ai / ha, 130-280 g ai / ha, 110-170 g ai / ha, 120-450 g ai / ha, 100-140 g ai / ha, or 110-475 g ai / ha.Trifludimoxazin

[0118] Compositions and methods of the present disclosure can include mixtures of the compounds of Formula I and trifludimoxazin, a PPO inhibitor. Exemplary uses of trifludimoxazin can include pre- and / or post-emergent control of broadleaf and grass weeds. It can be applied by aircraft on citrus fruits, pome fruits, cereal grain (except rice), tree nuts, peanuts, and foliage of legume vegetables. Non-agri cultural use sites include tree plantations, industrial landscaping, native grass openings, and conifer and hardwood plantations.

[0119] In some aspects, trifludimoxazin is applied to the foliage and roots of undesirable vegetation in an amount of 8 g ai / ha or more, such as 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, 50 g ai / ha or more, 60 g ai / ha or more, or 75 g ai / ha or more, 100 g ai / ha or more, 125 g ai / ha or more, 150 g ai / ha or more, 175 g ai / ha or more, 200 g ai / ha or more, 225 g ai / ha or more, 250 g ai / ha or more, or 275 g ai / ha or more; in an amount of 300 g ai / ha or less, such as 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, 75 g ai / ha or less, 60 g ai / ha or less, 50 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, or 12.5 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 8-300 g ai / ha, 12.5-50 g ai / ha, 12.5-100 g ai / ha, 40- 250 g ai / ha, 275-300 g ai / ha, 10-250 g ai / ha, 50-150 g ai / ha, 175-250 g ai / ha, 17.5-225 g ai / ha,75-200 g ai / ha, 150-250 g ai / ha, 20-175 g ai / ha, 40-150 g ai / ha, 125-150 g ai / ha, 30-200 g ai / ha, 40-125 g ai / ha, 25-100 g ai / ha, 35-275 g ai / ha, 60-150 g ai / ha, 8-75 g ai / ha, 15-70 g ai / ha, 150-225 g ai / ha, or 12.5-275 g ai / ha.GLYPHOSATE AND GLUFOSINATE

[0120] In addition to the compounds according to Formula I, the compositions can include glyphosate, glufosinate, an agriculturally acceptable salt thereof, or mixtures thereof.Glyphosate

[0121] In some aspects, compositions and methods of the present disclosure can include glyphosate or an agriculturally acceptable salt thereof. Glyphosate, as well as methods of preparing glyphosate, are known in the art. Glyphosate, shown below, is N- (phosphonomethyl)glycine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of glyphosate include its use for control of annual and perennial grasses and broadleaf weeds, particularly in crops that have been genetically modified to be tolerant of glyphosate.

[0122] Exemplary chemical forms of glyphosate include, but are not limited to, for example, glyphosate potassium salt, glyphosate sodium salt, glyphosate monoammonium salt, glyphosate diammonium salt, glyphosate isopropylamine (IP A) salt, glyphosate monoethanolamine (MEA) salt, glyphosate monomethylamine (MMA) salt, and glyphosate dimethylamine (DMA) salt. As used herein, glyphosate salt or salt of glyphosate generally refers to the reaction product of glyphosate with a moiety that can act as a base. Typically, the reaction is an acid-base reaction.

[0123] Glyphosate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, glyphosate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g ai / ha or more, such as 30 g ai / ha or more, 50 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, 105 g ai / ha or more, 110 g ai / ha or more, 115 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 135 g ai / ha or more, 140 g ai / ha or more, 145 g ai / ha or more, 150 g ai / ha or more, 155 g ai / ha or more, 160 g ai / ha or more, 165 g ai / ha or more, 170 g ai / ha or more, 175 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 210 g ai / ha or more, 220 g ai / ha ormore, 225 g ai / ha or more, 230 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 270 g ai / ha or more, 275 g ai / ha or more, 280 g ai / ha or more, 290 g ai / ha or more, 300 g ai / ha or more, 310 g ai / ha or more, 320 g ai / ha or more, 325 g ai / ha or more, 330 g ai / ha or more, 340 g ai / ha or more, 350 g ai / ha or more, 360 g ai / ha or more, 370 g ai / ha or more, 375 g ai / ha or more, 380 g ai / ha or more, 390 g ai / ha or more, 400 g ai / ha or more, 500 g ai / ha or more, 600 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 900 g ai / ha or more, 1000 g ai / ha or more, 1100 g ai / ha or more, 1200 g ai / ha or more, 1300 g ai / ha or more, 1400 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2100 g ai / ha or more, 2200 g ai / ha or more, 2300 g ai / ha or more, 2400 g ai / ha or more, 2500 g ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3800 g ai / ha or more, 3900 g ai / ha or more, 4000 g ai / ha or more, 4100 g ai / ha or more, 4200 g ai / ha or more, or 4250 g ai / ha or more, in an amount of 4300 g ai / ha or less, such as 4250 g ai / ha or less, 4200 g ai / ha or less, 4100 g ai / ha or less, 4000 g ai / ha or less, 3900 g ai / ha or less, 3800 g ai / ha or less, 3700 g ai / ha or less, 3600 g ai / ha or less, 3500 g ai / ha or less, 3400 g ai / ha or less, 3300 g ai / ha or less, 3200 g ai / ha or less, 3100 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 g ai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 g ai / ha or less, 2400 g ai / ha or less, 2300 g ai / ha or less, 2200 g ai / ha or less, 2100 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1400 g ai / ha or less, 1300 g ai / ha or less, 1200 g ai / ha or less, 1100 g ai / ha or less, 1000 g ai / ha or less, 900 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 600 g ai / ha or less, 500 g ai / ha or less, 400 g ai / ha or less, 390 g ai / ha or less, 380 g ai / ha or less, 375 g ai / ha or less, 370 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 330 g ai / ha or less, 325 g ai / ha or less, 320 g ai / ha or less, 310 g ai / ha or less, 300 g ai / ha or less, 290 g ai / ha or less, 280 g ai / ha or less, 275 g ai / ha or less, 270 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 230 g ai / ha or less, 225 g ai / ha or less, 220 g ai / ha or less, 210 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 175 g ai / ha or less, 170 g ai / ha or less, 165 g ai / ha or less, 160 g ai / ha or less, 155 g ai / ha or less, 150 g ai / ha or less, 145 g ai / ha or less, 140 g ai / ha or less, 135 g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 115 g ai / ha or less, 110 g ai / ha or less, 105 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 / haor less, 50 g ai / ha or less, or 30 g ai / ha or less, in an amount within any range defined between any pair of the preceding values, such as 25-4300 g ai / ha, such as 50-1800 g ai / ha, 60-375 g ai / ha, 125-2500 g ai / ha, 170-1700 g ai / ha, 95-350 g ai / ha, 800-3800 g ai / ha, 185-4000 g ai / ha, 390-3700 g ai / ha, 100-420 g ai / ha, 1200-3300 g ai / ha, or 750-4250 g ai / ha.Glufosinate

[0124] In some aspects, compositions and methods of the present disclosure can include glufosinate or an agriculturally acceptable salt thereof. Glufosinate, shown below, is 2-amino-4- (hydroxy(methyl)phosphinyl)butanoic acid. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of glufosinate include its use for control of annual and perennial grasses and broadleaf weeds, particularly in crops that have been genetically modified to be tolerant of glufosinate.

[0125] An exemplary salt of glufosinate is glufosinate-ammonium, which is also known as 2-amino-4-(hydroxy(methyl)phosphinyl)butanoic acid ammonium salt, and which has the following structure:

[0126] Glufosinate-ammonium is registered for controlling a wide variety of broad-leaved weeds and grasses particularly in glufosinate-tolerant crops like canola, maize, soybean, rice, cotton, and sugar beet. As used herein, glufosinate salt or salt of glufosinate generally refers to the reaction product of glufosinate with a moiety that can act as a base. Typically, the reaction is an acid-base reaction.

[0127] Other chemical forms of glufosinate include bilanafos, also known as bialaphos, which has the following structure:

[0128] Bilanafos also can be used in the salt form such as bilanafos sodium. Exemplary uses are described in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses include its use to control annual and perennial broadleaf weeds and grasses.

[0129] Glufosinate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, glufosinate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g ai / ha or more, such as 50 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more, 112.5 g ai / ha or more, 125 g ai / ha or more, 150 g ai / ha or more, 175 g ai / ha or more, 200 g ai / ha or more, 225 g ai / ha or more, 250 g ai / ha or more, 275 g ai / ha or more, 300 g ai / ha or more, 325 g ai / ha or more, 350 g ai / ha or more, 375 g ai / ha or more, 400 g ai / ha or more, 425 g ai / ha or more, 450 g ai / ha or more, 475 g ai / ha or more, 500 g ai / ha or more, 550 g ai / ha or more, 600 g ai / ha or more, 650 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more, 1000 g ai / ha or more, 1100 g ai / ha or more, 1200 g ai / ha or more, 1300 g ai / ha or more, 1400 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2050 g ai / ha or more, 2100 g ai / ha or more, 2150 g ai / ha or more, or 2200 g ai / ha or more, in an amount of 2250 g ai / ha or less (e.g., 2200 g ai / ha or less, 2150 g ai / ha or less, 2100 g ai / ha or less, 2050 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 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, 475 g ai / ha or less, 450 g ai / ha or less, 425 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, 112.5 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, or 50 g ai / ha or less, or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as in an amount of 25-2250 g ai / ha, such as 50-900 g ai / ha, 70-1800 g ai / ha, 125-475 g ai / ha, 112.5-1600 g ai / ha, 200-1300 g ai / ha, 350-2150 g ai / ha, 275-1900 g ai / ha, 400-1400 g ai / ha, 450-750 g ai / ha, 475-1100 g ai / ha, 500-2200 g ai / ha, or 650-1700 g ai / ha).Mesotrione

[0130] In some aspects, the HPPD inhibitor herbicide can comprise mesotrione or an agriculturally acceptable salt or ester thereof. Mesotrione, shown below, is 2-[4- (methylsulfonyl)-2-nitrobenzoyl]-l,3-cyclohexanedione. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of mesotrione include its use for pre- and postemergence control of broadleaf weeds and some grass weeds in maize.

[0131] Mesotrione can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, mesotrione is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai / ha or more, such as 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 175 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 220 g ai / ha or more, 225 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 275 g ai / ha or more, 280 g ai / ha or more, or 300 g ai / ha or more; in an amount of 301 g ai / ha or less, such as 300 g ai / ha or less, 280 g ai / ha or less, 275 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 225 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, 175 g ai / ha or less, 170 g ai / ha or less,160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 125 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, 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, or 25 g ai / ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 20-300 g ai / ha, 30-275 g ai / ha, 40-140 g ai / ha, 50-250 g ai / ha, 60-300 g ai / ha, 25-280 g ai / ha, 60-125 g ai / ha, 70-250 g ai / ha, 90-225 g ai / ha, 110-220 g ai / ha, 40-175 g ai / ha, 65-160 g ai / ha, 70-200 g ai / ha, 80-180 g ai / ha,90-250 g ai / ha, 140-225 g ai / ha, 110-240 g ai / ha, 120-175 g ai / ha, 110-150 g ai / ha, 25-85 g ai / ha, or 25-300 g ai / ha.Exemplification of Mixture Herbicidal Activity

[0132] The following Table lists the growth stages of the plants at the time of application for the results exemplified in this application:Table 1: Growth Stages of Plants For Results Exemplifiedj

[0133] Formulation Methods

[0134] Compound 1 and trifludimoxazin were applied in their technical form. The appropriate amount of Compound 1 required to spray all treatments was weighed out and dissolved in solvent 1, a mixture of 97:3% acetone: dimethyl sulfoxide (DMSO) to create a stock solution. This sample was placed in hot water and sonicated for 20 minutes. Additionally, the sample was kept in hot water until sprayed. This resulted in the test material being thoroughly dissolved. Aliquots of the stock solution were measured out to provide the quantity needed for each treatment on an acid equivalent basis for Compound 1. The volume of stock solution and amount of any mixing partner was calculated and subtracted from 20. This difference was added to the spray bottle with solvent mixture 2, a mix of acetone, water, isopropyl alcohol, DMSO, Agri-Dex ® crop oil concentrate (a heavy range, paraffin-based petroleum oil and nonionic emulsifiers commercially available from Rosecare) and nonionic Tergitol 15-S-7 in a 40.3:45.3:11.9: 1.3: 1.0:0.2 % v / v ratio. All percentages are listed on a volume basis. Lastly the required amount of mixing partner was added to the spray bottle. Collectively these additions resulted in a mix size of 20 ml.

[0135] The following mixing partners used in this trial were applied in their formulated form: saflufenacil under the tradename SHARPEN® , 341.5 g ai / L suspension concentrate (SC), sulfentrazone under the tradename SPRATAN® 4F, 480 g ai / L suspension concentrate (SC), glyphoste-K salt under the tradename ROUNDUP POWERMAX ® 3, 575 g ae / L soluble liquid (SL), glufosinate under the tradename LIBERTY® 280 SL, 280 g ai / L soluble liquid (SL),diclosulam under the tradename STRONGARM ®, 840 g ai / KG water dispersible granule (WDG), Arylex under the tradename ELEV ORE® , 68.5 g ai / L soluble liquid (SL), mesotrione under the tradename CALLISTO® , 420 g ai / L suspension concentrate (SC). Appropriate amounts of all liquid formulated herbicides were measured out and added directly to the spray bottle. Diclosulam was formulated as a WDG, and the amount required for all treatments in a trial was measured out and dissolved in water to create a stock solution. Aliquots of the stock solution were measured out to provide the quantity needed for each treatment. Plants were grown in a soil media 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 proprietary amounts of limestone, starter fertilizer, and wetting agent. Profile Greens Grade is a sand-sized granule formed from calcining illite and montmorillonite clay.Several seeds of each species were planted in 10 cm square pots and top watered twice daily. Plant material was propagated in a warm greenhouse with temperature ranging from 25 to 28° C and 50 to 60% relative humidity at the Corteva Global Headquarters (Indianapolis, Indiana, USA). Natural light was supplemented with 1000-watt metal halide overhead lamps with an average illumination of 500 pE m "2s photosynthetic active radiation for 16 consecutive hours each day. Plants were top-watered prior to herbicide application and sub-watered after herbicide application. Herbicide applications were made to 2 replicates of each plant species at the 3 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 fitted with an 8003E nozzle from Spray Systems Company (North Avenue and Schmale Road, P.O. Box 7900, Wheaton, IL 60187), and used a spray pressure of 276 kPa pressure and a speed of 3.1 km / h. The nozzle height was 46 cm above the plant canopy. The experimental design used for the trials was a randomized complete block with 2 replications per treatment. After application, plants were placed on carts according to the randomization and returned to the greenhouse. Plants were subwatered after treatment with Indianapolis city water or fertilized three times a week with a commercial fertilizer solution (Jack’s Professional 15-5-15 4 Ca 2Mg fertilizer (manufactured by JR PETERS INC., 6656 Grant Way, Allentown, PA 18106; www.jrpeters.com). Percent visual control assessments were made on a scale of 0 to 100% (where 0 was no control and 100 was complete plant death) at 14 and 21 days after application.Table 2 Percent (%) Weed control for Compound 1 and mixing partner 21 days after application(DAA). Results are the average of 2 reps.Table 3 Percent (%) Weed control for Compound 1 and mixing partner 21 days after application (DAA). Results are the average of 2 reps.Table 4 Percent (%) Weed control for Compound 1 and mixing partner 21 days after application(DAA). Results are the average of 2 reps.Table 5 Percent (%) Weed control for Compound 1 and mixing partner 21 days after application (DAA). Results are the average of 2 reps.Table 6 Percent (%) Weed control for Compound 1 and mixing partner 21 days after application(DAA). Results are the average of 2 reps.Table 7 Percent (%) Weed control for Compound 1 and mixing partner 21 days after application (DAA). Results are the average of 2 reps.Table 8 Percent (%) Weed control for Compound 1 and mixing partner 21 days after application(DAA). Results are the average of 2 reps.Table 9 Percent (%) Weed control for Compound 1 and mixing partner 21 days after application(DAA). Results are the average of 2 reps.Table 10 Percent (%) Weed control for Compound 1 and mixing partner 21 days after application (DAA). Results are the average of 2 reps.Table 11 Percent (%) Weed control for Compound 1 and mixing partner(s) 21 days after application (DAA). Results are the average of 2 reps.Table 12 Percent (%) Weed control for Compound 2 and mixing partner 12 days after application (DAA). Results are the average of 2 reps.

[0136] While this disclosure has been described using exemplary details, the present disclosure may be further modified within the spirit and scope of this disclosure. This application is therefore intended to cover any variations, uses, or adaptations of the disclosure using its general principles. Further, this application is intended to cover such departures from the present disclosure as come within known or customary practice in the art to which this disclosure pertains.

[0137] The benefits, advantages, solutions to problems, and any elements that may cause any benefit, advantage, or solution to occur or become more pronounced are not to be construed as critical, required, or essential features or elements. The scope is accordingly to be limited bynothing other than the appended claims, in which reference to an element in the singular is not intended to mean “one and only one” unless explicitly so stated, but rather “one or more.”

[0138] In the detailed description herein, references to “one aspect,” “an aspect,” “an example aspect,” “detail” etc., indicate that the aspect described may include a particular feature, structure, or characteristic, but every aspect may not necessarily include the particular feature, structure, or characteristic. Moreover, such phrases are not necessarily referring to the same aspect. Further, when a particular feature, structure, or characteristic is described in connection with an aspect, it is submitted that it is within the knowledge of one skilled in the art with the benefit of the present disclosure to affect such feature, structure, or characteristic in connection with other aspects whether or not explicitly described. After reading the description, it will be apparent to one skilled in the relevant art(s) how to implement the disclosure in alternative aspects.

[0139] Furthermore, no element, component, or method step in the present disclosure is intended to be dedicated to the public regardless of whether the element, component, or method step is explicitly recited in the claims.

Claims

CLAIMSWHAT IS CLAIMED IS:

1. A composition comprising a compound according to Formula I:Formula I, wherein X is Ci-Cs alkyl; and a second compound selected from the group consisting of halauxifen, diclosulam, glyphosate, glufosinate, mesotrione, saflufenacil, sulfentrazone, and trifludimoxazin, and an agriculturally acceptable salt or ester thereof.

2. The composition according to claiml, wherein X is C5 -alkyl.

3. The composition according to claim 2, wherein the second compound is halauxifen, or an agriculturally acceptable salt or ester thereof.

4. The composition according to claim 2, wherein the second compound is diclosulam, or an agriculturally acceptable salt or ester thereof.

5. The composition according to claim 2, wherein the second compound is glyphosate, or an agriculturally acceptable salt or ester thereof.

6. The composition according to claim 2, wherein the second compound is glyphosinate, or an agriculturally acceptable salt or ester thereof.

7. The composition according to claim 2, wherein the second compound is mesotrione, or an agriculturally acceptable salt or ester thereof.

8. The composition according to claim 2, wherein the second compound is saflufenicil, or an agriculturally acceptable salt or ester thereof.

9. The composition according to claim 2, wherein the second compound is sulfentrazone, or an agriculturally acceptable salt or ester thereof.

10. The composition according to claim 2, wherein the second compound is trifludimoxazin, or an agriculturally acceptable salt or ester thereof.

11. The composition according to any of the previous claims wherein the weight ratio between a compound of formula I and a second compound from about 40: 1 to about 1 :40 g ae / ha.

12. A method of controlling undesirable vegetation comprising the steps of, wherein the composition of claim 1 is applied at a rate of between about 200 grams to about 3000 grams of acid equivalent per hectare (g ae / ha).

13. A method of controlling undesirable vegetation according to claim 12, wherein the rate is between about 375 g ae / ha to about 1600 g ae / ha.

14. A method of controlling undesirable vegetation in a crop that has been made tolerant or resistant to 2,4-dichlorophenoxyacetic acid, which comprises contacting the vegetation or the locus thereof with or applying to the soil to minimize the emergence of undesirable vegetation, a herbicidally effective amount of a composition according to any one of the previous claims.

Images