Background of the Invention Glyphosate, also known as N- (phosphonomethyl) glycine, is commonly used as a broad spectrum post-emergent herbicide. The herbicide is applied to the foliage of an unde- sired plant, whereupon it is absorbed by the foliar tissue and transported throughout the plant. Once glyphosate is absorbed in the plant, it inhibits amino acid synthesis in a biochemical pathway that is common to almost all plants, but is absent in animals.

Various salts of glyphosate, methods for preparing salts of glyphosate, formulations of glyphosate or its salts, and methods of use of glyphosate or its salts are disclosed in U. S. Patent No. 5,998, 332 to Sato et al. ; U. S. Patent No. 5, 468, 718 to Burval et al. ; U. S. Patent No. 4,405, 531 to Franz; and"Glyphosate : A Unique Global Herbicide, " ACS Monograph 189, p. 27-64 (1997); all of which are incorporated herein in their entireties for all purposes.

Although glyphosate is widely used as an herbicide, visual symptoms of its effective- ness appear at a relatively late stage. Some herbicidal compositions remedy this prob- lem by combining the glyphosate with another herbicide such as a diphenyl ether, often used to control annual broad-leaf weeds and grasses. Although such a combination accelerates the appearance of visual symptoms of herbicide's action, solubility prob- lems are associated with combining glyphosate and diphenyl ether herbicides. As such, these herbicides are typically combined in low dosage form and/or are formulated as emulsions to avoid the solubility problems. For example, U. S. Patent No. 5,565, 409 to Sato et al. described microemulsions that include glyphosate and diphenyl ether.

Similarly, homoalaninylmethylphosphinate, also known as glufosinate, is subject to solubility problems when combined with diphenyl ether herbicides.

Therefore, there is a need for herbicidal compositions that include diphenyl ether and glyphosate or glufosinate as a solution.

Summary of the Invention As embodied and broadly described herein, this invention, in one aspect, relates to herbicidal compositions that include a) a N-phosphonomethylglycine or homoalaninyl- methylphosphinate herbicide or a salt or acid thereof; b) a diphenyl ether herbicide or a salt or ester thereof; c) a glycol ; d) an amine source; and e) a carrier. The present compositions are formulated as solutions. Also included is the product of mixing the components a), b), c), d) and e).

Moreover, the invention relates to a method of inhibiting the growth of an undesired plant that includes contacting the plant with a herbicidally effective amount of the above-described herbicidal composition.

Furthermore, the present invention describes method of making such compositions by mixing together the above-described compositions components to form a solution.

Advantages of the invention will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the-inven- tion. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, as claimed.

Detailed Description The present invention may be understood more readily by reference to the following detailed description of exemplary embodiments of the invention and the examples included therein.

Before the present compounds, compositions, and methods are disclosed and de- scribed, it is to be understood that this invention is not limited to specific synthetic methods of making that may of course vary. It is also to be understood that the termi- nology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting.

In this specification and in the claims that follow, reference will be made to a number of terms that shall be defined to have the following meanings: The term"alkene"as used herein intends a branched or unbranched unsaturated hydrocarbon group containing at least one double bond, such as ethylene, propylene,

1-butene, 2-butene, and the like. The alkene group may have one or more hydrogen atoms replaced with a functional group, such as a hydroxyl, halogen, alkoxy, and/or aryl group.

The term"alkyl"as used herein refers to a branched or unbranched saturated hydro- carbon group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like. The alkyl group may have one or more hydrogen atoms replaced with a func- tional group, such as a hydroxyl, halogen, alkoxy, and/or aryl group.

The term"alkyne"as used herein refers to a branched or unbranched unsaturated hydrocarbon group containing at least one triple bond, such as acetylene, propyne, 1-butyne, 2-butyne, and the like. The alkyne group may have one or more hydrogen atoms replaced with a functional group, such as a hydroxyl, halogen, alkoxy, and/or aryl group.

As used throughout, the term"contacting"is used to mean at least an instance of ex- posure of at least one plant cell to the present composition by applying the herbicide using any method known in the art.

In general,"herbicidally effective amount"means the amount needed to achieve an observable herbicidal effect on plant growth, including the effects of plant necrosis, plant death, growth inhibition, reproduction inhibition, inhibition of proliferation, and removal, destruction, or otherwise diminishing the occurrence and activity of a plant.

One of ordinary skill in the art will recognize that the potency and, therefore, a"herbi- cidally effective amount, "can vary for the various compositions used in the invention.

The term"plant"as used herein means terrestrial plants and aquatic plants. Inclusive of terrestrial plants are germinating seeds, emerging seedlings and herbaceous vegeta- tion including the roots and above-ground portions, as well as established woody plants. Inclusive of aquatic plants are algae, vegetative organisms free-floating and immersed species that are normally rooted in soil. A non-exhaustive list of plants in- cludes the following genera without restriction: Abutilon, Amaranthus, Artemisia, Ascle- pias, Avena, Axonopus, Borreria, Brachiaria, Brassica, Bromus, Chenopodium, Cir- sium, Commelina, Convolvulus, Cynodon, Cyperus, Digitaria, Echinochloa, Eleusine, Elymus, Equisetum, Erodium, Helianthus,-imperata, Ipomoea, Kochia, Lolium, Malva, Oryza, Ottochloa, Panicum, Paspalum, Phalaris, Phragmites, Polygonum, Portulaca, Pteridium, Pueraria, Rubus, Salsola, Setaria, Sida, Sinapis, Sorghum, Triticum, Typha, Ulex, Xanthium and Zea.

Broadleaf species are exemplified without limitation by the following : velvetleaf (Abuti- Ion theophrasti), pigweed (Amaranthus spp. ), mugwort (Artemisia spp.), milkweed (Asclepias spp. ), buttonweed (Borreria spp.), oilseed rape, canola, indian mustard, etc.

(Brassica spp.), canada thistle (Cirsium arvense), commelina (Commelina spp. ), field bindweed (Convolvulus arvensis), filaree (Erodium spp. ), sunflower (Helianthus spp. ), morning glory (Ipomoea spp. ), kochia (Kochia scoparia), mallow (Malva spp. ), wild buckwheat, smartweed, etc. (Polygonum spp. ), purslane (Portulaca spp. ), kudzu (Pu- eraria spp. ), russian thistle (Salsola spp. ), sida (Sida spp.), wild mustard (Sinapis ar- vensis) and cocklebur (Xanthium spp.).

Narrowleaf species are exemplified without limitation by the following : wild oat (Avena fatua), carpetgrass (Axonopus spp. ), brachiaria (Brachiaria spp. ), downy brome (Bro- mus tectorum), bermuda grass (Cynodon dactylon), yellow nutsedge (Cyperus escu- lentus), purple nutsedge (C. rotundus), crabgrass (Digitaria spp. ), barnyard grass (Echinochloa crus-galli), goosegrass (Eleusine indica), quackgrass (Elymus repens), lalang (Imperata cylindrica), annual ryegrass (Lolium multiflorum), perennial ryegrass (Lolium perenne), rice (Oryza sativa), ottochloa (Ottochloa nodosa), guineagrass (Panicum maximum), dallisgrass (Paspalum dilatatum), bahiagrass (Paspalum no- tatum), canarygrass (Phalaris spp. ), reed (Phragmites spp.), foxtail (Setaria spp.), johnsongrass (Sorghum halepense), wheat (Triticum aestivum), cattail (Typha spp.), and corn (Zea mays).

Other plant species are exemplified without limitation by the following : horsetail (Equi- setum spp. ), bracken (Pteridium aquilinum), blackberry (Rubus spp. ) and gorse (Ulex europaeus).

"Salt"as used herein includes salts that can form with, for example, amines, alkali metal bases and alkaline earth metal bases or quaternary ammonium bases, including zwitterions. Suitable alkali metal and alkaline earth metal hydroxides as salt formers include the hydroxides of lithium, sodium, potassium, magnesium or calcium. Illustra- tive examples of amines suitable for forming ammonium cations are ammonia as well as primary, secondary and tertiary C1-C18 alkylamines, C1-C4 hydroxyalkylamines and C2-C4 alkoxyalkylamines typically methylamine, ethylamine, n-propylamine, iso- propylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl ethylamine, methyl isopropylamine, methyl hexylamine, methyl nonylamine, methyl pentadecylamine, methyl octadecylamine, ethyl butylamine, ethyl heptylamine, ethyl octylamine, hexyl heptylamine, hexyl octyl- amine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butyl- amine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine,

ethanolamine, n-propanolamine, isopropanolamine, N, N-diethanolamine, N-ethyl- propanolamine, N-butylethanolamine, allylamine, n-but-2-enylamine, n-pent-2-enyl- amine, 2, 3-dimethylbut-2-enylamine, dibut-2-enylamine, n-hex-2-enylamine, propyl- enediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n- butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine ; heterocyclic amines such as pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines such as anilines, methoxyanilines, ethoxyanilines, o-, m-and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines.

Herbicidal compositions of the present invention include a) a N-phosphonomethyl- glycine or homoalaninyl methylphosphinate herbicide or a salt or acid thereof; b) a diphenyl ether herbicide or a salt or ester thereof; c) a glycol ; d) an amine source; and e) a carrier; wherein the composition is formulated as a solution.

The N-phosphonomethyglycine herbicide is preferably glyphosate of the formula (I) : wherein Z is COOH, COSH, COCI, COBr, COF, COI, or COR3 ; RI, R2, and R3 are each . I independently OH or OR4; and R4 is an ether amine salt-forming cation of the formula (ll) : H4N-R5 6 wherein R5 and R6 are each independently Ci-Ce alkyl, C2-C6 alkene, or C2-C6 alkyne ; wherein the glyphosate is in acid or salt form.

In one embodiment, Z is COOH and R, and R2 are OH. Preferably, the glyphosate is present as an isopropylamine salt. Other embodiments include trimesium, trimethylsul- fonium and sodium sesqui-salts of glyphosate. Moreover, the acid glyphosate may be combined with a suitable acid acceptor, including, but not limited to ammonium, am- monium acetate, sodium acetate, potassium acetate, ammonium carbonate, sodium carbonate, and the like.

The homoalaninylmethylphosphinate herbicide is preferably glufosinate of the formula (ll) : wherein Z is COOH, COSH, COCI, COBr, COF, COI, or COR3 ; Ri, and R3 are each independently OH or OR4; and R4 is an ether amine salt-forming cation of the formula (ll) : H4N-R5 O-R6 (I) wherein R5 and R6 are each independently Ci-C6 alkyl, C2-C6 alkene, or C2-C6 alkyne ; wherein the glufosinate is in acid or salt form.

Diphenyl ether herbicides include not only the herbicides, but also, the metabolites, salts and esters thereof. In general, diphenyl ether herbicides are known by skilled workers to have two generally substituted phenyl rings linked by an oxygen atom.

These herbicides are typically substituted on the phenyl ring at positions 2 and 4 ; 3; 3 and 5; or 2,4, and 6. Specific exemplary diphenyl ether herbicides include acifluorfen, acifluorfen-sodium, acifluorfen-potassium, fomesafen, 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitroacetophenone oxime-o- (acetic acid), and 5- [2-chloro-4- (trifluoromethyl) phenoxy]-2-nitro-a-methoxyacetophenone oxime-o- (acetic acid). In one embodiment, the diphenyl ether herbicide is acifluorfen or fomesafen.

The acid/salt characteristics of the herbicide components of the present compositions may change as the components are in solution. For example, upon mixing isopropyl- amine glyphosate and sodium acifluorfen, the isopropylamine associated with the glyphosate may become associated with acifluorfen, thereby producing isopropylamine acifluorfen. The resulting combinations are within the scope of the present invention as they are mere derivatives of the herbicidal components.

Glycols useful in the present invention may be any compatible glycol, polyhydric alco- hols, or polyglycol. Exemplary suitable glycols include ethylene glycol, propylene gly- col, 1. 3-propanediol, 1, 2-butanediol, diethylene glycol, dipropylene glycol, hexylene glycol, glycerol, low molecular weight polyethylene glycol and low molecular weight polypropylene glycol. Moreover, glycol ethers that exhibit water solubility such as ethyl- ene glycol monomethyl ether, ethylene glycol dimethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol monobutyi ether, monoisobutyl ether, dipropylene glycol monoether are within the scope of the present invention.

Surfactants may be used, such as block copolymers of ethylene oxide and propylene oxide.

The present compositions include an amine source, which may be any compatible amine. Suitable amines may include alkyl amines such as monomethylamine, dimethyl- amine, trimethylamine, diethylamine, triethylamine,-propylamine, di-n-propanolamine, n-butylamine, n-dibutylamine, n-tributylamine, isobutylamine, didisobutylamine, sec- butylamine, mono-n-butylamine, n-amylamine, diamylamine, triamylamine, hexylamine, 2-ethylbutylamine, n-heptylamine, 2-ethyhexylamine, di-2-ethylbutylamine, n-heptyl- amine, 2-ethylbutylamine, n-heptylamine, 2-ethylhexylamine, 2-ethylhexylamine, di-2- ethylhexylamine, cyclohexylamine. Also alkanol amines such as monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, triiso- propanolamine, diglycol amine, 2-amino-2methyl-1-propanol, 2-amino-2 methyl-1, 3 propanol"2-amino-2 ethyl-1, 3 propanol, tris (hydroxymethyl) aminomethane. Suitable amides may include formanide.

The molar ratio of N-phosphonomethylglycine herbicide to diphenyl ether herbicide can vary widely. For example, N-phosphonomethylglycine herbicide to diphenyl ether her- bicide may be from about a 1: 1 molar ratio to about a 10: 0.5 molar ratio. In one em- bodiment, N-phosphonomethylglycine herbicide to diphenyl ether herbicide is present from about a 2: 1 molar ratio to about a 4: 0.5 molar ratio.

The present compositions preferably comprise a carrier. Any suitable carrier may be employed including water, aqueous solutions, N-methylpyrrolidone, methanol, ethanol, isopropyl alcohol, acetone, butyl cellosolve, 2-ethyl-1 hexanol, cyclohexanone, hydro- carbons and other water-immiscible ethers, esters and ketones, and combinations thereof.

In general, conventional glyphosate salts compositions contain one or more surfactants to increase the biological effectiveness of the active ingredient. A surfactant is not needed to form the present herbicidal compositions as solutions. However, the pres- ence of a surfactant in an aqueous composition has many beneficial effects : (1) surfac- tants can alter the size distribution of spray droplets to increase the number of small- sized droplets which are less likely to rebound from the plant surface; (2) surfactants increase adhesiveness of the spray droplets to decrease run-off of the composition from the plant surface; and (3) surfactants may enhance the penetration of the plant surface.

Advantageously, the carrier and/or salt-forming cation of the present invention may be selected to increase the biological activity of the active ingredient; thereby eliminating

the need for a surfactant. However, one or more surface active ingredients may be added to the composition, if desired. Suitable surface active ingredients include surfac- tants, emulsifying agents, and wetting agents.

A wide range of surfactants is available and can be selected readily by those skilled in the art from"The Handbook of Industrial Surfactants, "2nd Edition, Gower (1997), which is incorporated herein by reference in its entirety for all purposes. There is no restriction on the type or chemical class of surfactant that can be used. Nonionic, ani- onic, cationic and amphoteric types, or combinations of more than one of these types, are all useful in particular situations.

Among nonionic surfactants, exemplary classes include polyoxyethylene alkyl, alkyne, alkynyl or alkylaryl ethers, such as polyoxyethylene primary or secondary alcohols, alkylphenols or acetylenic diols ; polyoxyethylene alkyl or alkyne esters, such as ethoxy- lated fatty acids; sorbitan alkylesters, whether ethoxylated or not; glyceryl alkylesters ; sucrose esters; and alkyl polyglycosides. Exemplary anionic surfactant classes include fatty acids, sulfates, sulfonates, and phosphate mono-and diesters of alcohols, alkyl- phenols, polyoxyethylene alcohols and polyoxyethylene alkylphenols, and carboxylates of polyoxyethylene alcohols and polyoxyethylene alkylphenols. These can be used in their acid form but are more typically used as salts, for example sodium, potassium or ammonium salts.

Cationic surfactants classes include polyoxyethylene tertiary alkylamines or alkenyl- amines, such as ethoxylated fatty amines, quaternary ammonium surfactants and polyoxyethylene alkyletheramines. Representative specific examples of such cationic surfactants include polyoxyethylene (5) cocoamine, polyoxyethylene (15) tallowamine, distearyldimethylammonium chloride, N-dodecylpyridine chloride and polyoxypropylene (8) ethoxytrimethylammonium chloride. Many cationic quaternary ammonium surfac- tants of diverse structures are known in the art to be useful in combination with gly- phosate and can be used in compositions contemplated herein.

Compositions of this invention may also contain other active ingredients, for example multiple N-phosphonomethylglycine herbicides and/or diphenyl ether herbicides; ferti- lizers such as ammonium nitrate, urea, potash, and superphosphate; phytotoxicants and plant growth regulators; and pesticides. These additional ingredients may be used sequentially or in combination with the above-described compositions. For example, the plant (s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.

Other optional components may be admixed with the present compositions to facilitate the application and/or effectiveness of the active ingredient. To this end, optional com- ponents that may be added include antifoaming agents including silicone based anti- foaming agents; thickening agents such as fumed silica ; antimicrobial agents; antioxi- dants; buffers; dyes; perfumes; stabilizing agents; and antifreezing agents. Exemplary antifreezing agents include but are not limited to, glycols such as propylene glycol and ethylene glycol, N-methylpyrrolidone, cyclohexanone, and alcohols such as ethanol and methanol.

The solutions of the present invention may be liquid concentrated and diluted solutions.

In general, concentrated solutions are sold commercially and may be mixed with water by the end user, thereby creating a clear solution. The concentrated solutions are also translucent such that the active ingredients do not precipitate out of solution and are not in an emulsion.

In one exemplary embodiment, the composition comprises from about 2 wt. % to about 20 wt. % of one or more N-phosphono-methylglycine herbicides; from about 1 wt. % to about 30 wt. % of one or more diphenyl ether herbicides; from about 10 wt. % to about 50 wt. % of one or more glycols ; from about 10 wt. % to about 50 wt. % of one or more amines; with the remainder being a carrier, such as N-methylpyrrolidone and/or water.

In another exemplary embodiment, the N-phosphonomethylglycine herbicide concen- tration in the solution is from about 1. 0 Ib/gal to about 1.5 Ib/gal.

When operating in accordance with the present invention, the growth of an undesired plant may be inhibited by contacting the plant with an herbicidally effective amount of the composition of the present invention. The application of such herbicidal composi- tions to terrestrial plants can be carried out by conventional methods, e. g. boom and hand sprayers and spray dusters. The compositions can also be applied from airplanes as a spray because of their effectiveness at low dosages. The application of herbicidal compositions to aquatic plants is usually carried out by spraying the compositions on the aquatic plants in the area where control of the aquatic plants is desired.

The application of an herbicidally effective amount of the compositions of this invention to the target plant is dependent upon the response desired in the plant as well as such other factors as the plant species and stage of development thereof, the amount of rainfall, and the specific glyphosate salt employed. In foliar treatment for the control of terrestrial plants, the active ingredients are desirably applied in amounts from about 0.01 to about 20 or more pounds per acre or more preferably 0.2 to about 5 or more pounds per acre. In applications for the control of emerged aquatic plants the active

ingredients are applied to the plants at a typical rate of 0.2 to about 5 or more pounds per acre.

The compositions of this invention are also useful as harvesting aids in many crops.

Thus, for example, the crop could be sprayed with the compositions of this invention to reduce the bulk of unwanted material and make the harvesting of the crops easier.

Such crops are for example, peanuts, soybeans, and root crops such as potatoes, sugar beets, red beets, and the like.

The compositions of this invention are useful in planting seeds in a vegetated area without plowing or otherwise mechanically preparing a seed bed. The crop seed can be drill planted or otherwise seeded in combination with a prior or subsequent application of a composition of this invention to kill undesired growing vegetation provided that the composition is applied before the emergence of the crop plant. As the sprayed plants wither and die, they act as a mulch and moisture retaining layer in which the seeds can germinate or to keep the soil warm and moist.

The compositions of this invention provide a wide spectrum of weed control and are also extremely useful as general herbicides as well as in controlling unwantedplants in orchards, tree farms and various crops. For example, it has been found that by direct- ing a spray of the compositions of this invention at the unwanted plants while essen- tially preventing such spray from contacting the leaves of trees, that such unwanted plants are controlled while there is no apparent injury to the trees. In such directed spraying, the spray can fall on the woody portion of the fruit tree or other tree without any apparent effect. Thus, the directed spray method of control is useful with crops such as plantation crops, i. e. rubber, coffee, bananas, tea, etc. and in orchards such as citrus fruits, apples, peaches, pears, nuts, olive, in vineyards and in bramble crops and in nursery crops to control the undesired plants and in crops such as cotton, soybeans, sugarcane and the like. The directed spraying can be done with or without a protective device to prevent contact of the spray with the leaves of such crop plants.

The compounds of the present compositions may be readily synthesized using tech- niques generally known to synthetic organic chemists. The compositions may be pro- duced by mixing a) at least one N-phosphonomethylglycine or homoalaninylmethyl- phosphinate herbicide or a salt or acid thereof; b) at least one diphenyl ether herbicide or a salt or ester thereof; c) at least one glycol ; d) at least one amine source; and e) at least one carrier to form a solution.

Experimental The following examples are put forth so as to provide those of ordinary skill in the art with a complete disclosure and description of how the compounds, compositions, articles, devices, and/or methods claimed herein are made and evaluated, and are intended to be purely exemplary of the invention and are not intended to limit the scope of what the inventors regard as their invention. Efforts have been made to ensure accuracy with respect to numbers (e. g. , amounts, temperature, etc. ) but some errors and deviations should be accounted for. Unless indicated otherwise, percent is percent by weight given the component and the total weight of the composition, temperature is in °C or is at ambient temperature, and pressure is at or near atmospheric.

Example 1 Mixtures of the isopropylamine salt of glyphosate, sodium acifluorfen and water were created to determine the solubility and stability of the mixtures. The results are shown in Table 1.

Table 1: Isopropylamine Salt of Glyphosate and Sodium Acifluorfen Mixtures Active Ingredient (s) (molar ratios) Total Active, Physical Ingredient Conc Observations/ (g/l) Stability Isopropylamine salt of glyphosate (IPA 540 Clear solution glyphosate) (100%) Sodium Salt of acifluorfen (sodium 530 Clear solution acifluorfen) (100%) IPA glyphosate + sodium aciflourfen (3: 1) 432 White precipitate IPA glyphosate + sodium aciflourfen (3: 1) 240 White precipitate IPA glyphosate + sodium aciflourfen (3: 1) 120 White precipitate IPA glyphosate + sodium aciflourfen (3: 1) 50 White precipitate IPA glyphosate + sodium aciflourfen (3: 1) 43 Clear solution Example 2 Mixtures of the isopropylamine salt of glyphosate, sodium acifluorfen and water were created to determine the interactions of the mixtures. The mixtures were filtered with a 0.45 micron membrane and the amount of sodium acifluorfen was measured in th filtered solution. The results are shown in Table 2.

Table 2 : Isopropylamine Salt of Glyphosate and Sodium Acifluorfen Mixtures Variable Mixture 1 Mixture 2 Mixture 3 Glyphosate : Acifluorfen Mole Ratios 2: 1 1: 1 1: 2 Sodium acifluorfen (wt. %) 5. 00 5. 00 5. 00 Sodium glyphosate (wt. %) 4. 67 2. 33 1. 16 Sodium acifluorfen in filtered solution (wt. %) 5.16 5.14 5.07 Physical solution observations Clear Hazy Hazy solution Physical filtrate observation Clear Hazy-Hazy- solution colloid colloid

Example 3 Mixtures of the isopropylamine salt of glyphosate, sodium acifluorfen, co-solvent and water were created to observe the solutions. The amounts of the components are shown in Table 3a and the specfic co-solvent and resulting solutions are shown in Table 3b.

Table 3a: Mixture Components for Example 3 Component Content (wt. %) Sodium acifluorfen TGAI (44% At) 16.3 IPA glyphosate (45.72% Al) 43.3 Co-solvent (from table 3b) 4. 5 Carrier (water) 45.1 Total 100. 0 Table 3b: Co-solvents and Solution Evaluations Co-solvent Chemical Classification Physical Observation Ethylene glycol Polyhydric alcohol Initial solution, crystals in 24 hours Propylene glycol Initial solution, crystals in 24 hours Hexylen glycol Initial solution, phase separation in 24 hours Pluracol E-400 Polyethylene glycol 2-phase gel on container bottom- Pluracol E-300 2-phase gel on container bottom Iconol TDA-3 Alkylphenol ethoxylate 2-phase gel on container bottom Tetronic 90R4 2-phase gel on container bottom Tetronic 150R1 Block copolymer 2-phase gel on container bottom Tetronic 701 surfactant 2-phase gel on container bottom Tetronic 704 2-phase gel on container bottom Tetronic 901 2-phase gel on container bottom Pluronic L62 Block copolymer 2-phase gel on container bottom Pluronic L92 surfactant 2-phase gel on container bottom APG 2067 Alkyl glucoside 2-phase gel on container bottom Tween 20 Sorbitan surfactant 2-phase gel on container bottom Tween 80 2-phase gel on container bottom

Example 4 Mixtures of the isopropylamine salt of glyphosate, sodium acifluorfen, ethylene glycol, amine source and water were created to observe the solutions. The amounts of the components are shown in Table 4a and the specific amine source and resulting solu- tions are shown in Table 4b.

Table 4a: Mixture Components for Example 4

Component Content (wt. %) Sodium acifluorfen TGAI (44% Al) 11.21 IPA glyphosate (76% Al) 17.93 Amine source (from Table 4b) 20. 0 Ethylene glycol 40.0 Carrier (water) 10.86 Total 100. 0 Table 4b: Amine Sources and Solution Evaluations Amine Source Physical Observation Isopropyl amine Crystals Monoisopropanol amine Clear solution Diisopropanol amine Clear solution Triisopropanol amine Clear solution Diglycol amine Two phase separation Ethyl ethanolamine Clear solution Ethyl Diethanolamine Clear solution Diethanol amine Clear solution Triethanol amine Clear solution Dithylethanolamine Two phase separation

Example 5 Mixtures of glyphosate, acifluorfen, co-solvent system and water were created to ob- serve the solubility of acifluorfen. The resulting solubility is shown in Table 5.

Table 5: Acifluorfen Solubility in Various Co-solvents Co-solvent Sys-Glyphosate Sodium/Amine Acifluorfen Solubility at 20°C (mix- tem Concentration ture % w/w) (Acid basis) Ethylene Glycol/Water Ratio 0. 0 0. 5 1. 0 2. 0 Isopropyl amine 0 % >44. 0 % * >29. 2%* >23. 0%* >17.8% with ethylene 6 % 0. 0 % 0. 0 % 1. 4 % 9. 7 % glycol 12% 0.0% 0.0% 0.0% 9.7% 18% 0. 0% 0.0% 0.0% 0.0% Diisopropanol 0% >44. 0 % * >29. 2% * >23. 4%* >17.8%* amine with 6 % 0. 0% 0. 1 % 9. 2% 9. 8 % ethylene glycol 12 % 0. 0% 0. 0% 0. 24 % 9. 8 % 18% 0. 0% 0.0% 0. 0% 0. 9% Maximum value limited by TGAl concentration

Example 6 Mixtures of glyphosate, acifluorfen, co-solvent system and water were created to ob- serve the effect of storage on the solution. The solutions were created and stored for one month, with the results as shown in Tables 6a and 6b.

Table 6a: Physical Testing results for Various Storage Conditions Composition Acifluorfen : glyphosate Ratio 1 : 2 1 : 3 1 : 4 1 : 6 1 : 8 Sodium acifluorfen (40.5%) 13. 46 8. 97 6. 73 4. 49 3. 36 Diisopropanol amine (99%) 10. 67 10. 67 10. 67 10. 67 10. 67 Glyphosate acid (0.76%) 14. 34 14. 34 14. 34 14. 34 14. 34 Water 26. 53 31. 02 33. 26 35. 50 36. 62 Ethylene glycol 35. 00 35. 00 35. 00 35. 00 35. 00 Total 100. 00 100. 00 100. 00 100. 00 100. 00 Physical Storage Conditions Physical Observations after 1 month Freeze/Thaw 5 cycles solution solution solution solution solution 5°C solution solution solution solution Solution 25°C solution solution solution solution solution 50°C solution solution solution solution solution Solution = sample remained clear with the acifluorfen in solution.

Table 6b: Physical Testing results for Various Storage Conditions Composition Acifluorfen : glyphosate Ratio 1 : 2 1 : 3 1 : 4 Sodium acifluorfen (40. 5%) 13. 46 8. 97 6. 73 Diisopropanol amine (99%) 10. 67 10. 67 10. 67 Glyphosate acid (0.76%) 14. 34 14. 34 14. 34 Water 26. 53 31. 02 33. 26 Ethylene glycol 35. 00 35. 00 35. 00 Total 100. 00 100. 00 100. 00 Physical Storage Conditions Physical Observations after 1 month Freeze/Thaw 5 cycles solution solution solution 5°C solution solution solution 25°C solution solution solution 50°C solution solution solution

Example 7 Mixtures of glufosinate, fomesafen, acifluorfen and water were created to determine the interactions of the mixtures. The results are shown in Table 7.

Table 7: Glufosinate, Fomesafen and Acifluorfen Mixtures Ingredient Fomesafen Acofluorfen Mixture (wt %) Mixture (wt %) Glufosinate 16. 5 16. 5 Sodium acifluorfen 0.0 4.1 Fomesafen 4.1 0.0 Water 79. 4 79. 4 Total 100. 0 100. 0 Physical observation Clear solution Clear Solution

Example 8 Mixtures of the glyphosate-trimesium, sodium acifluorfen, fomesafen, amine, glycol and water were created to determine the interactions of the mixtures. The results are shown in Table 8.

Table 8 : Glyphosate-trimesium, Sodium Acifluorfen, and Fomesafen Mixtures Ingredient Fomesafen Formulation Acifluorfen Formulation (wt. %) (wt. %) Glyphosate-trimesium 16. 5 16. 5 16. 5 16. 5 Sodium acifluorfen 0. 0 0. 0 4. 1 4. 1 Fomesafen 4. 1 4.1 0.0 0.0 Diisopropanol amine 0. 0 10. 0 0. 0 10. 0 Ethylene glycol 0. 0 40. 0 0. 0 40. 0 Water 79. 4 29. 4 79. 4 29. 4 Total 100. 0 100. 0 100. 0 100. 0 Physical observation Crystals Clear Solution Crystals Clear Solution

Throughout this application, various publications are referenced. The disclosures of these publications in their entireties are hereby incorporated by reference into this.. application for all purposes.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the scope or spirit of the

invention. Other embodiments of the invention will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the invention being indicated by the following claims.