OA17870A - Synergistic herbicidal weed control and improved crop tolerance from combinations of 2,4D-Choline and Glufosinate in 2,4-D- and Glufosinate tolerant soybeans, corn, cotton. - Google Patents

Abstract

Provided herein are herbicidal compositions comprising a mixture comprising (a) a choline salt of 2,4-dichlorophenoxyacetic acid (2,4-D-choline) and (b) a salt of 2-amino-4(hydroxymethylphosphinyl) butanoic acid (glufosinate). The compositions provide synergistic weed control of undesirable vegetation and improved crop tolerance in 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton. The compositions also provide synergistic weed control of undesirable vegetation in areas including, but not limited to, non-crop, perennial crop, fruiting crop, and plantation crop areas.

Description

SYNERGISTIC HERBICIDAL WEED CONTROL AND IMPROVED CROP TOLERANCE FROM COMBINATIONS OF 2,4-D-CHOLINE AND GLUFOSINATE IN

2,4-D- AND GLUFOSINATE-TOLERANT SOYBEANS, CORN, COTTON

Cross Reference to Related Applications

This application claims the benefit of U.S. Provisional Patent Application Serial Nos. 61/914,177 and 61/914,195 filed December 10, 2013, the disclosures of which are expressly incorporated herein by reference.

Background

The protection of crops from weeds and other végétation which inhibit crop growth is a recurring problem in agriculture. To help combat this problem, a variety of chemicals and chemical formulations effective in the control of such unwanted végétation hâve been synthesized and evaluated. Different classes of chemical herbicides hâve been disclosed in the literature and a large number are in commercial use. However, there remains a need for improved compositions and methods of use thereof that are effective in controlling undesirable végétation.

Summary

Compositions for controlling undesirable végétation containing a mixture containing synergistic, herbicidally effective amounts of:

(a) a choline sait of 2,4-dichlorophenoxyacetic acid (2,4-D-choline)

and (b) a sait of 2-amino-4-(hydroxymethylphosphinyl)butanoic acid (glufosinate)

are described herein. The compositions may also contain one or more agriculturally acceptable adjuvants and/or carriers.

Additionally, methods of controlling undesirable végétation and improving crop tolérance in 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton including contacting the undesirable végétation and the 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton or the locus thereof, including but not limited to foliage, soil or water, with a composition containing a mixture containing synergistic, herbicidally effective amounts of 2,4-D-choline and glufosinate are described herein. The undesirable végétation may include herbicide résistant or tolérant weeds and the undesirable végétation may be located in non-crop, perennial crop, fruiting crop, or plantation crop areas.

In another embodiment, methods of controlling undesirable végétation in non-crop, perennial crop, fruiting crop, or plantation crop areas including contacting the undesirable végétation or the locus thereof, including but not limited to foliage, soil or water, with a composition containing a mixture containing synergistic, herbicidally effective amounts of

2,4-D-choline and a sait of glufosinate are described herein.

Detailed Description

I. Définitions

As used herein, 2,4-D-choline is the choline sait of 2,4-dichlorophenoxyacetic acid or

2-hydroxy-/V,AI,/V-trimethylethanaminium 2-(2,4-dichlorophenoxy)acetate, which has the following structure:

Exemplary uses of 2,4-D-choline include controlling annual and perennial broad-leaved weeds, including glyphosate-resistant broad-leaved weeds. 2,4-D-choline can be used in crops that hâve been made tolérant to 2,4-D, particularly in 2,4-D-tolerant soybeans, corn, and cotton. 2,4-D-choline is generaliy, but is not required to be, applied post-emergent. 2,4D-choline can also be used for weed control in non-crop and perennial cropping Systems.

As used herein, glufosinate is 2-amino-4-(hydroxymethylphosphinyl)butanoic acid. An exemplary sait of glufosinate is glufosinate-ammonium, which is also known as the ammonium sait of 2-amino-4-(hydroxymethylphosphinyl)butanoic acid or ammonium (3amino-3-carboxypropyl)(methyl)phosphinate, and which has the following structure:

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

The term herbicide, as used herein, means an active ingrédient that kills, controls or otherwise adversely modifies the growth of plants. As used herein, a herbicidally effective or végétation controlling amount is an amount of active ingrédient that causes a “herbicidal effect,” i.e., an adversely modifying effect and includes déviations from natural development, killing, régulation, desiccation, retardation.

As used herein, “plants” and “végétation” include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from végétative propagules, and established végétation.

As used herein, immature végétation refers to small végétative plants prior to reproductive stage, and mature végétation refers to végétative plants during and after reproductive stage.

As used herein, 2,4-D-tolerant soybeans refer to soybeans that are genetically modified to be tolérant to 2,4-D. Examples of 2,4-D tolérant soybeans include soybeans containing the aa.d-12 gene which confers tolérance to 2,4-D (U.S. Patent 8,283,522 B2). As used herein, 2,4-D-tolerant corn refers to corn that is genetically modified to be tolérant to

2,4-D. Examples of 2,4-D tolérant corn include corn containing the aad-1 gene which confers tolérance to 2,4-D (U.S. Patent 7,838,733 B2). As used herein, 2,4-D-tolerant cotton refers to cotton that is genetically modified to be tolérant to 2,4-D. Examples of 2,4-D tolérant cotton include cotton containing the aad-12 gene which confers tolérance to 2,4-D. However, tolérance in each of these crops by the aad-1 or aad-12 genes or with alternative genes providing additional or alternative tolérance to transgenic crops [e.g., aad-13 (U.S. Patent 8,278,505 B2), tfdA (U.S. Patent 6,153,401 A), or 24dt02 (CN103060279)] is considered to be included within the scope of the 2,4-D- and glufosinate-tolerant soybeans, com, or cotton described herein.

As used herein, glufosinate tolérance refers to soybeans, com, or cotton that is genetically modified to be tolérant to glufosinate. Glufosinate tolérance can be provided, for example, by thepat gene (US 5,587,903 A) as shown herein; however, glufosinate tolérance could also be conferred within the scope of the 2,4-D- and glufosinate-tolerant soybeans, com, or cotton described herein by other genes providing transgenic crop tolérance to glufosinate [e.g., bar (U.S. Patent 5,561,236 A) and dsm2 (W02008070845)].

II. Compositions

A. Synergistic combinations

Provided herein are herbicidal compositions containing a mixture containing synergistic, herbicidally effective amounts of:

(a) the choline sait of 2,4-dichlorophenoxyacetic acid (2,4-D-choline)

and (b) a sait of 2-amino-4-(hydroxymethylphosphinyl)butanoic acid (glufosinate)

Agriculturally acceptable salts of glufosinate are anticipated to control undesirable végétation in combination with 2,4-D-choline and a sait of glyphosate. An example of such an agriculturally acceptable sait of glufosinate includes glufosinate-ammonium.

Furthermore, in some embodiments, the combination of 2,4-D-choline and a sait of glufosinate exhibit synergism, i.e., the herbicidal active ingrédients are more effective in combination than when applied individually. Synergism has been defined as “an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response of each factor applied separately.” Shaner, D. L., Ed. Herbicide Handbook, 10^th ed. Lawrence: Weed Science Society of America, 2014. In certain embodiments, the compositions exhibit synergy as determined by Colby’s équation. Colby,

S. R. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 1967,15, 20-22.

Additionally, in some embodiments, the combination of 2,4-D-choline and a sait of glufosinate improves crop tolérance in 2,4-D- and glufosinate-tolerant soybeans, corn and cotton.

Herbicidal activity is exhibited by the compounds when they are applied pre- and post-emergence directly to the plant or to the locus of the plant at any stage of growth. The effect observed dépends upon the plant species to be controlied, 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 spécifie compound employed, the spécifie adjuvants and carriers employed, the soil type, the amount of chemical applied, and the combinations thereof. These and other factors can be adjusted to promote non-selective or sélective herbicidal action. In some embodiments, the compositions described herein are applied as a post-emergence application, to relatively immature and mature undesirable végétation to achieve the maximum control of weeds.

In some embodiments, 2,4-D-choline and a sait of glufosinate are used in combination with other herbicides that are sélective for the soybeans, corn or cotton being treated and which complément the spectrum of weeds controlied by these compounds at the application rate employed. In some embodiments, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation or as a tank mix, at the same time or as sequential applications.

The présent compositions can be applied to weeds or their locus thereof, including but not limited to foliage, soil or water, by the use of conventional ground or aerial dusters, sprayers, and granule applicators and by other conventional means known to those skilled in the art.

In some embodiments, the concentration of the active ingrédients in the compositions described herein is from about 0.0005 to 99 percent by weight. In some embodiments, the concentration is from about 0.006 to 90 percent by weight. In compositions designed to be employed as concentrâtes, the active ingrédients, in certain embodiments, are présent in a concentration from about 0.01 to 98 weight percent, and in certain embodiments about 0.5 to 90 weight percent. Such compositions are, in certain embodiments, 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 embodiments, about 0.003 to 98 weight percent active ingrédient and in certain embodiments contain about 0.007 to 25.0 weight percent active ingrédient.

In certain embodiments of the compositions and methods described herein, 2,4-Dcholine is used in combination with a sait of glufosinate. With regard to the compositions, in some embodiments, the weight ratio of the compound of 2,4-D-choline to a sait of glufosinate is within the range from about 1:48 to about 64:1, from about 1:32 to about 48:1, from about 1:16 to about 16:1, from about 1:10 to about 10:1, from about 1:8 to about 8:1, from about 1:7 to about 7:1, from about 1:6 to about 6:1, from about 1:5 to about 5:1, from about 1:4 to about 4:1, from about 1:3 to about 3:1, from about 2:1 to about 1:4, from about 1:1 to about 1:2, from about 1:16 to about24:l, from about 1:8 to about 16:1, from about 4:1 to about 8:1, from about 2:1 to about 6:1, from about 1.5:1 to about 3:1, from about 1:1 to about 1.5:1, from about 1:1 to about 2.5:1, from about 2.5:1 to about 1:3, from about 3:1 to about 1:4, from about 1:2 to about 4:1 and from about 1:4 to about 7:1. In certain embodiments, the weight ratio of 2,4-D-choline to a sait of glufosinate is within the range from about 1:2 to about 2:1. In other embodiments, the weight ratio of 2,4-D-choline to a sait of glufosinate is within the range fforn about 3:1 to 2:3, from about 2:1 to about 8:1 and from about 1:1 to about 4:1.

With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation with a composition described herein, e.g., sequentially or simultaneously. In some embodiments, the composition is applied at an application rate from about 300 grams acid équivalent per hectare (g ae/ha) to about 11,200 g ae/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 600 g ae/ha to about 7,810 g ae/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 1,120 g ae/ha to about 2,800 g ae/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 1,300 g ae/ha to about 1,700 g ai/ha based on the total amount of active ingrédients in the composition.

The components of the mixtures described herein can be applied either separately, sequentially, tankmixed or as part of a mixture or multipart herbicidal system. In some embodiments, both components may be formulated together (e.g., in the same formulation) or separately (e.g., in separate formulations) and applied simultaneously. In another embodiment, one or more components may be formulated separately and the formulations applied sequentially. The time period between applications can vary, for example 1, 2, 4, 6, 8,10, or 12 hours or longer or 1,2, 3, 4, 5, 6, or 7 days or longer.

In one embodiment, the compositions exhibit synergy against a variety of weed types. In one embodiment, the combination of 2,4-D-choline and a sait of glufosinate in a ratio of about 1:1 to about 4:1 exhibits greater than about 5, 6, 7, 8, 9, 10, 11, 13, 15, 18, 20, 21, 22,

23, 24, or 25% control compared to the Colby predicted value at 6-28 days after application (DAA).

In another embodiment, the compositions exhibit synergy in reducing crop injury. In one embodiment, the combination of 2,4-D-choline and a sait of glufosinate in a ratio of about 1:1 to about 4:1 exhibits réductions of 5, 6, 7, 8, 9,10, 11,13, 15,18, 20, 21, 22, 23,

24, 25, 30 or 35% crop injury compared to the Colby predicted value at 2-15 days after application (DAA).

In another embodiment, the compositions exhibit synergy as defined by the efficacy values defined above against a variety of weed types or crops, including but not limited to, Amaranthus palmeri (Palmer pigweed, ΑΜΑΡΑ), Conyza canadensis (horseweed, ERICA), Salsola trcigus L. (Russian thistle, SASKR), and Sesbania exaltata (hemp sesbania, SEBEX).

In another embodiment, the compositions can be used to control glyphosate-tolerant soybeans (GLXMA) and other crops that hâve single site tolérance to, including but not limited to, glyphosate, acetolactate synthase (ALS) and other herbicide modes-of-action.

B. Other actives

The mixtures described herein can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable végétation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the compositions and methods described herein include, but are not limited to, acid, sait, and ester forms of the following herbicides: 4-CPA, 4-CPB, 4-CPP, 3,4-DA, 2,4-DB, 3,4-DB,

3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuronmethyl, bensulide, bentazon, benthiocarb, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole chlorprocarb, carfentrazone (e.g., carfentrazone-ethyl), CDEA, CEPC, chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlomitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon (e.g., cinidon-ethyl), cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate, clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop (e.g., cyhalofop-butyl), cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMP A, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethbenzamide, ethalfluralin, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, fenoxaprop-P (e.g., fenoxaprop-P-ethyl), fenoxaprop-P-ethyl + isoxadifen-ethyl, fenoxasulfone, fenquinotrione, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P (e.g., fluazifop-P-butyl), fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr (e.g., flufenpyrethyl), flumetsulam, flumezin, flumiclorac (e.g., flumiclorac-pentyl), flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, foryloxyfen, glyphosate, halauxifen, halosafen, halosulfuron (e.g., halosulfuron-methyl), haloxydine, haloxyfop-methyl, haloxyfop-P (e.g., haloxyfop-P-methyl), hexachloroacetone, hexaflurate, hexazinone, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iodosulfuronethyl-sodium, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen, lenacil, linuron, MAA, ΜΑΜΑ, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuronmethyl, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, orTzo-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham (e.g., phenmedipham-ethyl), phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron (e.g., primisulfuron-methyl), procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, prohexadione-calcium, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen (e.g., pyraflufen-ethyl), pyrasulfotole, pyrazogyl, pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P (e.g., quizalofop-P-ethyl), rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron (e.g., tribenuron-methyl), tricamba, triclopyr (e.g, triclopyr choline sait), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, vemolate, xylachlor, benzyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3methoxyphenyl)pyridine-2-carboxylate and salts, choline salts, esters, optically active isomers and mixtures thereof.

C. Safeners

In some embodiments, the compositions described herein are employed in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity. In some embodiments, the safeners are employed in rice, cereal, com, or maize settings. In some embodiments, the safener is cloquintocet or an ester or sait thereof. In certain embodiments, cloquintocet is utilized to antagonize harmful effects of the compositions on rice and cereals. In some embodiments, the safener is cloquintocet (mexyl).

D. Adjuvants/Carriers

In some embodiments, compositions provided herein iurther comprise at least one agriculturally acceptable adjuvant or carrier. Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for sélective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingrédients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrâtes or formulations that are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water-dispersible granules, microcapsules or wettable powders, or liquids, such as, for example, emulsifiable concentrâtes, solutions, émulsions or suspensions. They can also be provided as a pre-mix or tank mixed.

Suitable agricultural adjuvants and carriers include, but are not limited to, crop oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quatemary ammonium sait; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C11 alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C12-C16) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate99.

Liquid carriers that can be employed include water and organic solvents. The organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as minerai oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stéarate, w-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like. Spécifie organic solvents include, but are not limited to toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycérine, 7V-methyl-2-pyrrolidinone, Λζ/V-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. In certain embodiments, water is the carrier for the dilution of concentrâtes.

Suitable solid carriers include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, cellulose, and the like.

In some embodiments, the compositions described herein further comprise one or more surface-active agents. In some embodiments, such surface-active agents are employed in both solid and liquid compositions, and in certain embodiments those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants which may also be used in the présent formulations are described, inter alia, in McCutcheon ’s Détergents and Emulsifiers Annual, MC Publishing Corporation: Ridgewood, NJ, 1998 and in Encyclopedia of Surfactants, Vol. I-III, Chemical Publishing Company: New York, 1980-81. Surface-active agents include, but are not limited to salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide additionproducts, such as nonylphenol-Cig ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-Ci6 ethoxylate; soaps, such as sodium stéarate; alkylnaphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quatemary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stéarate; block copolymers of ethylene oxide and propylene oxide; salts of mono and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseed/canola oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils, and in certain embodiments, methyl esters.

In some embodiments, these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.

Other exemplary additives for use in the compositions provided herein include but are not limited to compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, pénétration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth régulants, fongicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.

III. Methods of use

Methods of controlling undesirable végétation in 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton, comprising contacting the végétation or the locus thereof, including but not limited to foliage, soil or water, with a composition containing a mixture containing synergistic herbicidally effective amounts of (a) 2,4-D-choline and (b) a sait of glufosinate are described herein. In certain embodiments, the methods employ the compositions described herein.

In another embodiment, methods of controlling undesirable végétation in non-crop, perennial crop, fruiting crop, or plantation crop areas, comprising contacting undesirable végétation or the locus thereof, including but not limited to foliage, soil or water, with a composition containing a mixture containing synergistic herbicidally effective amounts of (a)

2,4-D-choline and (b) a sait of glufosinate are described herein. In certain embodiments, the methods employ the compositions described herein.

Agriculturally acceptable salts of glufosinate are anticipated to control undesirable végétation in combination with 2,4-D-choline and a sait of glyphosate. An example of such an agriculturally acceptable sait of glufosinate includes glufosinate-ammonium.

The compositions and methods provided herein are utilized to control undesirable végétation. Undesirable végétation includes, but is not limited to, undesirable végétation that occurs in 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton; non-crop areas, including but not limited to pastures, grasslands, rangelands, fallowland, fencerows, parking areas, tank farms, storage areas, rights-of-way, utility areas, turf, forestry, aquatics, industrial végétation management (IVM) and fallow-bed prior to planting crops; perennial crops where the application contacts the undesirable végétation but does not contact the crop foliage, such as tree and vine orchards, including but not limited to citrus, grapes, almond, apple, apricot, avocado, beechnut, Brazil nut, buttemut, cashew, cherry, chestnut, chinquapin, crab apple, date, feijoa, fig, filbert, hickory nut, kiwi, lemon, lime, loquat, macadamia nut, mandarins, mayhaws, nectarine, olives, oranges, peach, pear, pecan, persimmon, pistachio, plum, pomegranates, pome fruit, prune, stone fruit, tree nuts, quince and walnut; fruiting crops (including, but not limited to, blueberries, guava, papaya, strawberries, taro, blackberries and raspberries) and plantation crops (including, but not limited to, coffee, cacao, rubber and palm oil).

The compositions and methods provided herein are utilized to control undesirable végétation. Undesirable végétation includes, but is not limited to, undesirable végétation that occurs in annual crops such as 2,4-D- and glufosinate-tolerant cereal crops, including but not limited to rice, wheat, barley, oats, rye and sorghum.

In some embodiments, the methods provided herein are utilized to control undesirable végétation found in row crops, tree and vine crops, perennial crops and non-crop areas. In certain embodiments, the undesirable végétation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Amaranthuspalmeri S. Wats. (Palmer amaranth, ΑΜΑΡΑ), 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. (southem 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, ELEUST), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild-proso millet, PANMI), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hemp sesbania, SEBEX), 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, AMAS S), 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. or Spermacoce latifolia (broadleaf buttonweed, 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. or Conyza canadensis (L.) Cronq. (horseweed, ERIC A), 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 momingglory, IPOHE), Ipomoea lacunosa L. (white momingglory, IPOLA), Lactuca serriola L./Tom. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia species (pusley, RCHSS), Salsola tragus L. (Russian thistle, SASKR), Sida species (sida, SIDSS), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis

L. (wild mustard, SINAR), Solanumptychanthum Dunal (eastem black nightshade, SOLPT), Tridaxprocumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (common cocklebur, XANST).

In some embodiments, the methods provided herein are utilized to control undesirable végétation in range and pasture areas. In certain embodiments, the undesirable végétation is Amaranthuspalmeri S. Wats. (Palmer amaranth, ΑΜΑΡΑ), 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), Conyza canadensis (L.) Cronq. (horseweed, ERICA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L./Tom. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhom plantain, PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB), Salsola tragus L. (Russian thistle, SASKR), Sesbanici exaltata (Raf.) Cory/Rydb. Ex Hill (hemp sesbania, SEBEX), 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).

In some embodiments, the combination of 2,4-D-choline and a sait of glufosinate is used to synergistically control Amaranthuspalmeri S. Wats. (Palmer amaranth, ΑΜΑΡΑ), Conyza canadensis (L.) Cronq. (horseweed, ERICA), Salsola tragus L. (Russian thistle, SASKR) and Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hemp sesbania, SEBEX).

2,4-D-choline and a sait of glufosinate may be used to control herbicide résistant or tolérant weeds. The methods employing the combination of 2,4-D-choline and a sait of glufosinate and the compositions described herein may also be employed to control herbicide résistant or tolérant weeds. Exemplary résistant or tolérant weeds include, but are not limited to, biotypes résistant or tolérant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, dimethoxy-pyrimidines, triazolopyrimidine sulfonamides, sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins (e.g., benzoic acids, phenoxycarboxylic acids, pyridine 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, Nphenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidinediones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS) inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulose biosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes-of-action such as quinclorac, and unclassifïed herbicides such as arylaminopropionic acids, difenzoquat, endothall, and organoarsenicals. Exemplary résistant or tolérant weeds include, but are not limited to, biotypes with résistance or tolérance to single or multiple herbicides, biotypes with résistance or tolérance to single or multiple chemical classes, biotypes with résistance or tolérance to single or multiple herbicide modes-of-action, and biotypes with single or multiple résistance or tolérance mechanisms (e.g., target site résistance or metabolic résistance).

The compositions and methods described herein are used to control undesirable végétation in 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton which may also be combined with traits providing glyphosate tolérance (e.g., résistant plant or bacterial EPSPS, GOX), dicamba-tolerance (e.g., DM0), pyridyloxy auxin-tolerance (e.g., aad-12, aad-13), auxin-tolerance, auxin transport inhibitor-tolerance, acetyl CoA carboxylase (ACCase) inhibitor-herbicide tolérance [e.g., aryloxyphenoxypropionate, cyclohexanedione, and phenylpyrazoline chemistries (e.g.,various ACCase genes and aad-1 gene)], acetolactate synthase (ALS)-inhibiting herbicide tolérance (e.g., imidazolinone, sulfonylurea, triazolopyrimidine sulfonanilide, pyrmidinylthiobenzoates, and other chemistries = AHAS, Csrl, SurA), 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-tolerance, phytoene desaturase (PDS) inhibitor-tolerance (e.g., pds, CYP1A1, CYP2B6, CYP2C19), carotenoid biosynthesis inhibitor-tolerance, protoporphyrinogen oxidase (PPO) inhibitor-tolerance, cellulose biosynthesis inhibitor-tolerance (e.g., ixr2-l, CYP1A1), mitosis inhibitor-tolerance, microtubule inhibitor-tolerance, very long chain fatty acid inhibitor-tolerance (e.g., CYP1A1, CYP2B6, CYP2C19), fatty acid and lipid biosynthesis inhibitor-tolerance (e.g., CYP 1 Al), photosystem I inhibitor-tolerance (e.g., SOD), photosystem II inhibitor (triazine, nitrile, and phenylurea chemistries) tolérance (e.g., psbA, CYP1A1, CYP2B6, CYP2C19, and Bxri), (such as, but not limited to, soybean, corn, cotton, canola/oilseed râpe, rice, cereals, sorghum, sunflower, sugar beet, sugarcane, and turf), for example, in conjunction with glyphosate, EPSP synthase inhibitors, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACCase inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, dimethoxypyrimidines, triazolopyrimidine sulfonamides, sulfonylaminocarbonyltriazolinones, ALS or acetohydroxy acid synthase (AHAS) inhibitors, HPPD inhibitors, PDS inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil. The compositions and methods may be used in controlling undesirable végétation in soybeans, corn, or cotton possessing single and multiple or stacked traits conferring tolérance to single or multiple chemistries and/or inhibitors of multiple modes of action.

The described embodiments 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 &om the spirit and scope of the claimed subject matter.

Examples

Example 1. Evaluation of Herbicidal Activity of Mixtures under Field Conditions

Methodology

These trials were conducted under field conditions in multiple states in the United States, including but not limited to Arkansas, Illinois, Indiana, Minnesota, Mississippi,

Nebraska, Ohio, Oklahoma, Texas, South Carolina and South Dakota. Trials were established as RCB (randomized complété block) design, with typically 3-4 replicates per treatment, and plot sizes varying from 6-15 feet (fit) wide by 10-25 fi long. Treatments were applied with small plot backpack sprayers, using pressurized air or carbon dioxide (CO₂) as propellant. Pressure varied from 22-50 pounds per square inch (psi), with spray tips typically of a Fiat Fan type applying water diluent at 15 gallons per acre (GPA). Boom sizes varied from 6.3-10 ft in width. Treatments were applied to soybean, cotton, corn or fallow crop land. Weed sizes varied, but ail treatments were applied as post-emergence treatments to weeds from 2 leaf to 2 tiller growth stages varying from 2 to 15 inches in height. The weed spectrum included, but was not limited to, Amaranthuspalmeri S. Wats. (Palmer amaranth, ΑΜΑΡΑ), Conyza canadensis (L.) Cronq. (horseweed, ERICA), Salsola tragus L. (Russian thistle, SASKR) and Sesbania exaltata (hemp sesbania, SEBEX).

2,4-D- and glufosinate-tolerant soybeans, corn and cotton and optionally a glyphosate trait in a breeding (CP 4 EPSPS) or a molecular stack (2mEPSPS) were used in ail tolérance trials.

Evaluation

Commercially available product of glufosinate-ammonium (Ignite® 280SL (Soluble Concentrate), containing 256 grams acid équivalent per liter (g ae/L)) was utilized in ail trials, either applied alone or tank-mixed with ammonium sulfate liquid (2.5% volume per volume (vol/vol)). The 2,4-D-choline sait formulation was a 456 g ae/L SL. If ammonium sulfate was mixed with glufosinate-ammonium, then ammonium sulfate was also mixed with the 2,4-D-choline sait + glufosinate-ammonium mixture. Ail treatments were mixed in water at appropriate formulated product rates to achieve the desired rates as shown based on a unit area of application (hectare). Treatments were rated at 2 to 28 days after application (DAA) as compared to the untreated control plants. The trial sites had naturally occurring populations of weeds. The treated plots and control plots were rated blind at various intervals after application. Ratings were based on a Percent (%) Visual basis, where 0 corresponds to no visual effect as seen as exemplified by weed control or crop injury and 100 corresponds to complété kill of the target weeds or complété crop injury.

Data were collected for ail trials and analyzed using various statistical methods.

Colby’s équation was used to détermine the herbicidal effects expected from the mixtures (Colby, S. R. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 1967,15, 20-22). A t-test (alpha=0.05) between Colby prédictions and observed combinations was used to test for significant différences indicating synergy or antagonism using replicate data. The results presented in Tables 1-5 were significant according to the described criteria.

The following équation was used to calculate the expected activity of mixtures containing two active ingrédients, A and B:

Expected = A + B - (A x B/100)

A = observed efficacy of active ingrédient A at the same concentration as used in the mixture;

B = observed efficacy of active ingrédient B at the same concentration as used in the mixture.

The results are summarized in Tables 1-7.

Table 1. Synergistic Herbicidal Weed Control (%Visual Control) from Combinations of 2,4D-Choline Sait + Glufosinate-ammonium in Multiple Field Trials at 7 to 28DAA.

	2,4-D-Choline sait	Glufosinateammonium	Combination
Weed Bayer Code	Evaluation Interval	g ae/ha	Mean% weed control	g ae/ha	Mean % weed control	Measured mean % weed control	Colby predicted mean % weed control
ΑΜΑΡΑ	7DAA	800	47.5	542	80.0	95.5	89.6
ΑΜΑΡΑ	10DAA	1065	55.0	542	54.3	90.8	79.5
ΑΜΑΡΑ	13DAA	1065	45.0	542	75.0	93.8	86.3
ΑΜΑΡΑ	16DAA	800	62.5	542	65.0	95.3	86.9
ΑΜΑΡΑ	21DAA	1065	38.8	542	51.3	92.5	70.3
ΑΜΑΡΑ	22DAA	800	48.8	542	56.3	91.5	77.3
ERICA	7DAA	1065	40.0	542	75.0	90.0	85.0
ERICA	13DAA	1065	40.0	542	85.0	95.0	91.0
ERICA	22DAA	1065	40.0	542	80.0	98.0	88.0
ERICA	28DAA	1065	30.0	542	98.0	100.0	98.6
SASKR	14DAA	1065	67.5	542	12.5	91.3	71.4
SASKR	21DAA	1065	65.0	542	6.3	91.3	67.2
SEBEX	8DAA	800	32.5	542	73.8	97.0	81.4
SEBEX	16DAA	800	42.5	542	78.8	98.3	88.1
SEBEX	23DAA	800	38.8	542	65.0	96.5	79.1

Table 2. Improved AAD12 Soybean (GLXMA) Crop Tolérance Results (%Visual Injury) from Combinations of 2,4-D-Choline Sait + Glufosinate-ammonium in Multiple Field Trials at 2 to 7DAA.

	2,4-D-Choline sait	Glufosinateammonium	Combination
Crop Bayer Code	Evaluation Interval	g ae/ha	Mean% crop injury	g ae/ha	Mean % crop injury	Measured mean % crop injury	Colby predicted mean % crop injury
GLXMA	2DAA	2130	5.0	1084	16.7	11.7	20.8
GLXMA	2DAA	2130	3.5	1084	1.5	1.5	4.9
GLXMA	3DAA	2130	0.3	1084	13.8	8.3	14.0
GLXMA	3DAA	1065	0.3	542	5.0	3.3	5.2
GLXMA	4DAA	2130	1.0	1084	23.3	16.7	24.1
GLXMA	4DAA	1065	0.0	542	16.7	6.0	16.7
GLXMA	4DAA	1065	0.0	542	9.3	3.0	9.3
GLXMA	6DAA	2130	4.0	1084	15.0	11.3	18.4
GLXMA	6DAA	1065	4.0	542	10.0	7.7	13.6
GLXMA	7DAA	2130	4.0	1084	28.3	16.0	31.2
GLXMA	7DAA	2130	13.3	822	15.0	20.0	26.3

Table 3. Improved AAD12 Soybean (GLXMA) Crop Tolérance Results (%Visual Injury) from Combinations of 2,4-D-Choline Sait + Glufosinate-ammonium in Multiple Field Trials at 9 to 15DAA.

	2,4-D-Choline sait	Glufosinateammonium	Combination
Crop Bayer Code	Evaluation Interval	g ae/ha	Mean % crop injury	g ae/ha	Mean % crop injury	Measured mean % crop injury	Colby predicted mean % crop injury
GLXMA	9DAA	2130	0.0	1084	15.0	10.0	15.0
GLXMA	9DAA	1065	0.0	542	10.5	3.8	10.5
GLXMA	13DAA	2130	3.3	1084	10.7	6.3	13.6
GLXMA	13DAA	1065	2.0	542	6.3	3.3	8.2
GLXMA	14DAA	1065	3.0	542	3.5	4.5	6.4
GLXMA	14DAA	1065	0.0	542	2.5	1.3	2.5
GLXMA	14DAA	2130	2.3	1084	25.0	8.3	26.8
GLXMA	15DAA	2130	0.0	1084	8.3	1.5	8.3

Table 4. Improved AAD12 Soybean (GLXMA) Crop Tolérance Results (%Visual Chlorosis) from Combinations of 2,4-D-Choline Sait + Glufosinate-ammonium in Multiple Field Trials at 2 to 4DAA.

	2,4-D-Choline sait	Glufosinateammonium	Combination
Crop Bayer Code	Evaluation Interval	g ae/ha	Mean % crop chlorosis	g ae/ha	Mean % crop chlorosis	Measured mean % crop chlorosis	Colby predicted mean % crop chlorosis
GLXMA	2DAA	2130	2.3	1084	12.8	9.3	14.7
GLXMA	2DAA	2130	0.0	1084	18.3	6.0	18.3
GLXMA	2DAA	2130	0.0	1084	9.3	4.5	9.3
GLXMA	3DAA	2130	0.0	1084	13.8	5.5	13.8
GLXMA	3DAA	2130	0.0	1084	15.0	3.8	15.0
GLXMA	3DAA	2130	1.3	1084	23.8	7.5	24.8
GLXMA	3DAA	2130	0.0	1084	12.8	7.3	12.8
GLXMA	3DAA	1065	0.0	542	6.8	3.5	6.8
GLXMA	3DAA	2130	0.8	1084	7.0	0.8	7.7
GLXMA	3DAA	2130	0.0	1084	10.5	6.3	10.5
GLXMA	3DAA	2130	0.5	1084	5.3	1.8	5.8
GLXMA	4DAA	2130	0.0	1084	25.0	6.0	25.0
GLXMA	4DAA	1065	0.0	542	10.7	3.0	10.7
GLXMA	4DAA	2130	0.0	1084	20.0	11.3	20.0
GLXMA	4DAA	1065	0.0	542	13.8	5.5	13.8
GLXMA	4DAA	2130	0.7	822	5.7	3.7	6.3
GLXMA	4DAA	2130	0.0	1084	15.3	9.0	15.3
GLXMA	4DAA	1065	0.0	542	7.0	5.0	7.0

Table 5. Improved AAD12 Soybean (GLXMA) Crop Tolérance Results (%Visual Chlorosis) from Combinations of 2,4-D-Choline Sait + Glufosinate-ammonium in Multiple Field Trials at 7 to 9DAA.

	2,4-D-Choline sait	Glufosinateammonium	Combination
Crop Bayer Code	Evaluation Interval	g ae/ha	Mean % crop chlorosis	g ae/ha	Mean % crop chlorosis	Measured mean % crop chlorosis	Colby predicted mean % crop chlorosis
GLXMA	7DAA	2130	0.0	1084	10.0	0.0	10.0
GLXMA	7DAA	2130	0.0	822	4.3	0.0	4.3
GLXMA	7DAA	2130	0.0	1084	8.5	3.5	8.5
GLXMA	7DAA	1065	0.0	542	4.0	0.8	4.0
GLXMA	7DAA	2130	1.7	1084	28.3	7.7	29.6
GLXMA	7DAA	1065	0.0	542	11.7	3.7	11.7
GLXMA	7DAA	2130	0.0	822	8.3	0.0	8.3
GLXMA	7DAA	2130	1.3	822	18.3	11.7	19.4
GLXMA	7DAA	2130	3.0	822	18.3	11.7	20.8
GLXMA	8DAA	2130	0.0	1084	6.3	3.3	6.3
GLXMA	8DAA	2130	0.0	1084	11.0	5.0	11.0
GLXMA	8DAA	1065	0.0	542	4.5	2.5	4.5
GLXMA	8DAA	2130	0.0	1084	15.0	9.8	15.0
GLXMA	8DAA	1065	0.0	542	6.0	3.8	6.0
GLXMA	9DAA	2130	0.0	1084	20.0	11.3	20.0
GLXMA	9DAA	1065	0.0	542	15.0	5.8	15.0

Table 6. Improved AAD12 Soybean (GLXMA) Crop Tolérance Results (%Visual Chlorosis) from Combinations of 2,4-D-Choline Sait + Glufosinate-ammonium in Multiple Field Trials at 13 to 15DAA.

	2,4-D-Choline sait	Glufosinateammonium	Combination
Crop Bayer Code	Evaluation Interval	g ae/ha	Mean % crop chlorosis	g ae/ha	Mean % crop chlorosis	Measured mean % crop chlorosis	Colby predicted mean % crop chlorosis
GLXMA	13DAA	2130	0.0	1084	1.3	0.3	1.3
GLXMA	13DAA	2130	0.0	1084	10.7	5.0	10.7
GLXMA	13DAA	1065	0.0	542	6.3	1.7	6.3
GLXMA	14DAA	2130	0.0	1084	1.5	0.0	1.5
GLXMA	14DAA	2130	0.0	822	1.7	0.0	1.7
GLXMA	14DAA	2130	0.0	1084	6.0	2.8	6.0
GLXMA	14DAA	2130	0.8	1084	9.0	4.5	9.7
GLXMA	14DAA	1065	0.0	542	1.8	0.8	1.8
GLXMA	14DAA	2130	1.3	1084	14.0	3.7	15.2
GLXMA	15DAA	2130	0.0	1084	7.0	0.0	7.0
GLXMA	15DAA	2130	0.0	1084	8.8	0.0	8.8

Table 7. Improved AAD12 Soybean (GLXMA) Crop Tolérance Results (%Growth Inhibition) from Combinations of 2,4-D-Choline Sait + Glufosinate-ammonium in Multiple Field Trials at 7 to 15DAA.

	2,4-D-Choline sait	Glufosinateammonium	Combination
Crop Bayer Code	Evaluation Interval	g ae/ha	Mean % crop growth inhibition	g ae/ha	Mean% crop growth inhibition	Measured mean % crop chlorosis	Colby predicted mean % crop growth inhibition
GLXMA	7DAA	2130	1	1084	14.0	6.7	14.9
GLXMA	14DAA	2130	0	1084	23.3	0.0	23.3
GLXMA	14DAA	2130	0	1084	3.0	0.0	3.0
GLXMA	15DAA	2130	0	1084	9.8	0.0	9.8

The following abbreviations are used in the tables above:

2,4-D-choline = choline sait of 2,4-dichlorophenoxyacetic acid glufosinate-ammonium = ammonium sait of 2-amino-4-(hydroxymethylphosphinyl)butanoic acid

ΑΜΑΡΑ = Amaranthuspalmeri S. Wats. (Palmer amaranth)

ERICA = Conyza canadensis (L.) Cronq. (horseweed)

SASKR = Salsolci tragus L. (Russian thistle) SEBEX = Sesbania exaltata (Raf.) Cory/Rydb, Ex Hill (hemp sesbania) GLXMA = Glycine max L. (soybean) g ae/ha = grains acid équivalent per hectare

DAA = Days After Application

The compositions and methods of the appended claims are not limited in scope by the spécifie compositions and methods described herein, which are intended as illustrations of a few aspects of the claims and any compositions and methods that are functionally équivalent are intended to fall within the scope of the claims. Various modifications of the compositions and methods in addition to those shown and described herein are intended to fall within the scope of the appended claims. Further, while only certain représentative composition materials and method steps disclosed herein are specifically described, other combinations of the composition materials and method steps also are intended to fall within the scope of the appended claims, even if not specifically recited. Thus, a combination of steps, éléments, components, or constituents may be explicitly mentioned herein; however, other combinations of steps, éléments, components, and constituents are included, even though not explicitly stated. The term “comprising” and variations thereof as used herein is used synonymously with the term “including” and variations thereof and are open, non-limiting terms. Although the terms “comprising” and “including” hâve been used herein to describe various embodiments, the terms “consisting essentially of ’ and “consisting of ’ can be used in place of “comprising” and “including” to provide for more spécifie embodiments of the invention and are also disclosed.

Claims (16)

1. A method of controlling undesirable végétation and improving crop tolérance in 2,4D- and glufosinate-tolerant soybeans, corn, or cotton, comprising contacting undesirable végétation and/or 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton or the locus thereof, or foliage, water or soil, with a composition comprising a mixture comprising a synergistic, herbicidally effective amount of:

(a) a choline sait of 2,4-dichlorophenoxyacetic acid (2,4-D-choline) and (b) a sait of 2-amino-4-(hydroxymethylphosphinyl)butanoic acid (glufosinate)

2. The method of claim 1, wherein the 2,4-D-choline and a sait of glufosinate are applied post-emergence to the undesirable végétation in the 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton.

3. The method of claim Error! Reference source not found., wherein the 2,4-Dcholine and a sait of glufosinate are applied pre-emergence to the undesirable végétation in the 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton.

4. The method of claim 1, wherein the undesirable végétation is contacted prior to planting the 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton.

5. The method of claim 1, wherein the sait of glufosinate is the ammonium sait.

6. The method of any of claims 1-5, wherein the weight ratio of (a) to (b) is from about 1:48 to about 64:1, from about 1:16 to about 24:1, from about 1:4 to about 4:1, or from about 1:2 to about 2:1.

7. The method of any of claims 1-6, wherein the 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton possess single or multiple or stacked traits conferring tolérance to single or multiple herbicides or inhibitors of single or multiple modes-of-action.

8. A method of any of claims 1-7, wherein improving crop tolérance comprises reducing injury in the 2,4-D- and glufosinate-tolerant soybeans, corn, or cotton.

9. The method of any of claims 1-8, wherein (a) and (b) are applied simultaneously.

10. The method of any of claims 1-8, wherein (a) and (b) are applied sequentially.

11. The method of any of claims 1-10 wherein synergy is determined by the Colby équation.

12. The method of any of claims 1-Error! Reference source not found., wherein the undesirable végétation comprises a herbicide résistant or tolérant weed.

13. The method of claim 12, wherein the résistant or tolérant weed is a biotype with résistance or tolérance to single or multiple herbicides or single or multiple chemical classes, or inhibitors of single or multiple herbicide modes-of-action.

14. The method of claim 12 or claim 13, wherein the résistant or tolérant weed is a biotype résistant or tolérant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, photosystem I inhibitors, 5-enolpyruvyl-shikimate-3-phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall or organoarsenicals.

15. The method of any of claims 1-14, further comprising contacting the undesirable végétation and the 2,4-D- and glufosinate-tolerant soybeans, com and cotton or the locus thereof, or foliage, water or soil, with a herbicidally effective amount of an additional herbicide.

16. The method of any of claims 1-15, further comprising contacting the undesirable végétation and the 2,4-D- and glufosinate-tolerant soybeans, com and cotton or the locus thereof with a herbicide safener.