Patent Publication Number: US-2020296961-A1

Title: High concentrate fomesafen herbicide formulations

Description:
RELATED APPLICATION 
     This application is a continuation-in-part of U.S. application Ser. No. 15/262,683 filed Sep. 12, 2016, which is a continuation of U.S. application Ser. No. 15/237,035 filed Aug. 15, 2016, which claims benefit to U.S. Provisional application Ser. No. 62/207,110 filed Aug. 19, 2015, which all are incorporated by reference in its entirety. 
    
    
     BACKGROUND OF THE INVENTION 
     Fluorine containing diphenyl ether derivatives with applications as herbicides were first disclosed in European Patent 3416 and U.S. Pat. No. 4,384,135 by Cartwright et. al. which are both incorporated by reference in their entirety for all useful purposes. One of the more useful compounds that came out of this discovery is 5-[2-chloro-4-(trifluoromethyl) phenoxy]-N-methylsulfonyl-2-nitrobenzamide, which carries the common name fomesafen. Fomesafen is used in a number of commercially available products either alone or in combinations with other herbicides. Fomesafen has the following chemical formula: 
     
       
         
         
             
             
         
       
     
     Recently there has been renewed research and additional applications for fomesafen due to its usefulness as a tool for managing weeds that have developed resistance to other herbicides. Enhancing the weed control efficacy and ease of application of fomesafen are desirable goals for this herbicide and are met with a number of difficulties and limitations. One difficulty that must be overcome is the poor water solubility of fomesafen. Fomesafen has a water solubility of only 50 mg/liter. This makes the preparation of concentrated water solutions that can be further diluted by the end user impractical. Fomesafen exhibits significantly greater solubility in organic solvents such as acetone, xylene, methylene chloride, and methanol. However, the flammability and/or toxicity of these solvents make them unsuitable for the preparation of concentrates. The most cost efficient way to address this limitation is to convert the fomesafen into a water soluble salt by reacting it with either sodium hydroxide or potassium hydroxide. This makes possible the preparation of water based formulations of the salt form of fomesafen up to 22.8% (21.7% fomesafen acid equivalent). While it is possible to increase the concentration of fomesafen salt in water to levels higher than 22.8%, such formulations become unstable in colder temperatures and are not practical for commercial use. In addition, pH of these compositions must be maintained at levels of 7.5 or higher. These alkaline pH ranges can have a negative impact on the weed control performance of both the fomesafen and other herbicides that are jointly applied with it. It is also established that the current commercial salt formulations of fomesafen have physical compatibility problems with other herbicides and fertilizers that are mixed with it. 
     Nevill et al. (US 2002/0004457) (Nevill) which is incorporated by reference in its entirety, discloses a very broad disclosure of surfactants in paragraphs [0077]-[0079] and as follows:
         Suitable surface-active compounds are, depending on the nature of the active compounds under a) and b) to be formulated, nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.   Examples of suitable anionic, nonionic and cationic surfactants are listed, for example, in WO 97134485, on pages 7 and 8.   The surfactants conventionally used in the art of formulation and which can also be used in the preparation of the herbicidal compositions according to the invention are described, inter alia, in “McCutcheon&#39;s Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood, N.J., 1981, Stache, H., “Tensid-Taschenbuch” [Surfactant Handbook], Carl Hanser Verlag, Münich/Vienna, 1981 and M. and J. Ash. “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81.   Suitable surface-active compounds are, depending on the nature of the active compounds under a) and b) to be formulated, nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties. Examples of suitable anionic, nonionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8. The surfactants conventionally used in the art of formulation and which can also be used in the preparation of the herbicidal compositions according to the invention are described, inter alia, in ‘Mc Cutcheon&#39;s Detergents and Emulsifiers Annual” MC publishing Corp., Ridgewood, N.J., 1981, Stache, H., “Tensid-Taschenbuch” [Surfactant Handbook], Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical publishing Co., New York, 1980-81.       

     Nevill does recognize the criticality of selecting the surfactant. 
     SUMMARY OF THE INVENTION 
     We have surprisingly discovered that it is now possible to prepare concentrated solutions of fomesafen in the non-salt form mixed with a surfactant selected from the group consisting of fatty amine, alkanolamine, fatty amine alkoxylate and alkoxylated quaternary ammonium compounds. The selection of the surfactant is critical. This water solubilized fomesafen may in turn be used to produce novel herbicide formulations that address the limitations of conventional fomesafen salt formulations that are now used commercially. Cold temperature stable concentrates of fomesafen up to about 65% by weight can be produced by this invention. This means that it is now possible to produce fomesafen formulations that deliver significantly more active ingredient than the current commercial products. This in turn provides consumers the advantages of reduced application rates, storage, handling, and costs. 
     We have also found that the formulations resulting from this invention provide superior compatibility and weed control with mixed and applied jointly with other herbicide products such as glyphosate and paraquat. These advantages may reduce or eliminate the need to add other components to the spray application (such as, but not limited to, adjuvants) for this purpose. The mild pH ranges possible for this composition (pH 6.0-7.5) also reduce the potential for eye irritation. Additional applications for this invention include novel formulations in combination with other herbicides such as, but not limited to, glyphosate, metolachlor, S-metolachlor, and acetochlor. 
     The composition according to the invention can also contain fertilizers, herbicides, fungicides, insecticides, plant regulators, plant nutritional products, macronutrients, micronutrients, humectants, acids, such as inorganic acids and/or organic acids. 
     Another object is to apply the agriculture composition according to the invention in a band or (starter) application, broadcast application or strip placement application. A band or starter application is the placement of the agricultural formation in the same area as the seed. A broadcast application is the general distribution of the agricultural composition over the entire soil surface. A strip placement is the placement of the agricultural composition in narrow strips. Crops will differ with placement and spacing. For example, spacing in sugarcane is 60″ and with multiple applications could be placed about 2″ to about 12″ at plant in the drill or placed on the soil surface with supplement applications after cane has been planted. 
     The articles “a” and “an” are used herein to refer to one or to more than one (i.e., to at least one) of the grammatical object of the article. By way of example, “an element” means one element or more than one element. 
     When ranges are used, all the numbers included in the range are covered. For example, if the range is from 1 to 5, would include 1, 2, 3, 4, 5 and decimals, such as 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9 etc. 
     As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. “About” as used herein when referring to a measurable value such as an amount, a temporal duration, and the like, indicates that the calculation or the measurement allows some slight imprecision in the value (with some approach to exactness in the value; approximately or reasonably close to the value; nearly). If, for some reason, the imprecision provided by “about” is not otherwise understood in the art with this ordinary meaning, then “about” as used herein indicates at least variations that may arise from ordinary methods of measuring or using such parameters. 
     The above summary of the present invention is not intended to describe each disclosed embodiment or every implementation of the preset invention. The detailed description that follows more particularly exemplifies illustrative embodiments. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     The preparation of concentrated non-salt formulations of fomesafen is accomplished by solubilizing this herbicide in specific surfactants rather than in solvents or water. The specific surfactants are selected from the group consisting of fatty amine, alkanolamine, fatty amine alkoxylate and alkoxylated quaternary ammonium compounds. 
     The following primary surfactants work as solubilizing surfactants for non-salt fomesafen, individually and in combination. 
     Fatty amines including, but not limited to:
         Cocoamine and oleylamine;       

     Alkanolamines including, but not limited to:
         Diethanolamine and triethanolamine;       

     Alkoxylated amines including, but not limited to:
         Fatty amine alkoxylates such as tallow amine alkoxylates;       

     Alkoxylated quaternary ammonium compounds. 
     The following secondary surfactants can be included to enhance beneficial properties such as compatibility and efficacy, but do not work as solubilizing surfactants for non-salt fomesafen. 
     Alcohol alkoxylates including, but limited to:
         Branched or linear;   Those containing ethylene oxide or propylene oxide;       

     Alcohol alkoxylate sulfates; 
     Alkylphenol alkoxylates, including, but not limited to:
         Nonylphenol and octylphenol such as octylphenol polyglycol ether;   Those containing ethylene oxide or propylene oxide;       

     Alkylaryl sulfonates, including but not limited to:
         Docecylbenzenesulfonates;       

     Amine oxides; 
     Betaine derivatives; 
     Carboxylated alcohols; 
     Ethoxylated fatty acids; 
     Ethoxylated fatty esters, ethers and oils, including but not limited to:
         Castor oil polyglycol ether;       

     Fatty esters; 
     Glycerol esters; 
     Phosphate ester surfactants including, but not limited to:
         Phosphate esters of alcohol alkoxylates;   Phosphate esters of alkylphenol alkoxylates;       

     Sarcosine derivatives; 
     Silicone-based surfactants; 
     Sorbitan derivatives including, but not limited to:
         Sorbitan esters;   Alkoxylated sorbitan esters;       

     Sucrose and glucose derivatives including, but not limited to:
         Alkylpolyglucosides;       

     Sulfates and sulfonates of alkoxylated alkylphenols; 
     Sulfates of alcohols; 
     Tristyrylphenol alkoxylates; 
     Polyethoxylated aliphatic phenols; 
     Polymers of ethylene or propylene oxides; or 
     Ethoxylated triglycerides and ethoxylated seed oils. 
     It is noted that non-ionic surfactants, anionic surfactants, amphoteric surfactants and certain cationic surfactants do not work. The invention can be practiced without any these surfactants. The surfactants disclosed by Nevill are very generic see paragraph nos. [0078] and [0079]:
         Examples of suitable anionic, nonionic and cationic surfactants are listed, for example, in WO 97/34485, on pages 7 and 8.   The surfactants conventionally used in the art of formulation and which can also be used in the preparation of the herbicidal compositions according to the invention are described, inter alia, in “McCutcheon&#39;s Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood, N.J., 1981, Stache, H., “Tensid-Taschenbuch” [Surfactant Handbook], Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81.       

     The following surfactants listed in Nevill do not work and are excluded from the invention: 
     Ca dodecylbenzenesulfonate, 
     Castor oil polyglycol ether and 
     Octylphenyl polyglycol ether. 
     The disclosed composition required to practice this invention comprise of 1-65% preferably 10-40% and more preferably 20-30% of the herbicide fomesafen in the non-salt form solubilized with 1-70% and preferably 20-50% by weight and most preferably 30-40% by weight with surfactants. Once solubilized, water may be added as diluent. 
     The pH of this composition should be in the range of 2.0-7.5 with the preferred range being 6.5-7.0. Acidic compounds may be used to lower the pH into the preferred range. These include, but are not limited to: acetic acid, lactic acid, maleic acid, succinic acid, sulfuric acid, hydrochloric acid, phosphoric acid, or nitric acid. Alkaline compounds may be used to raise the pH into the preferred range. These include, but are not limited to: sodium hydroxide, potassium hydroxide, ammonium hydroxide, calcium hydroxide, magnesium hydroxide, or sodium bicarbonate. 
     The composition(s) disclosed may be used in the range of 0.05-10.0% and preferably 0.125-5.00% and most preferably 0.25-2.50% by weight in a water and/or fertilizer based spray mixtures. These spray mixtures may also contain other herbicides as well as fungicides, insecticides, plant growth regulators, or plant nutritional products such as, macronutrients, and micronutrients, humectants, acids, such as inorganic acids and/or organic acids and fertilizer products. 
     The following is a list of herbicides, fungicides, insecticides, plant regulators, plant nutritional products that can be used according to the invention include, but are not limited to: 
     Accord Concentrate, 
     Accord XRT II, 
     Authority First DF, 
     Authority XL, 
     Avaris, 
     Axilo BZM, 
     Axilo Mix 5, 
     Axilo Mn, 
     Cadet, 
     Classic, 
     Cobalt, 
     Cobra, 
     CoRoN 10-0-10 B, 
     CoRoN Full Bor, 
     CoRoN 25-0-0-0.5B, 
     Durango DMA, 
     ENC, 
     First Rate, 
     Fusilade DX, 
     Gly Star Gold, 
     Glyfos Original, 
     Glyfos Xtra, 
     Glystar Plus, 
     Glytrel MnP, 
     Gramoxone, 
     Halex GT, 
     Headline AMP, 
     Headline EC, 
     Headline SC, 
     Honcho Plus, 
     Hoss Ultra, 
     Kickstand MN, 
     K-Leaf, 
     Leverage 2.7, 
     Leverage 360, 
     Liberty 280 SL, 
     Marvel, 
     Megafol, 
     Nucleus 0-0-15, 
     Paraquat Firestorm, 
     Pendimethalin, 
     Powermax, 
     Prowl H2O, 
     Quadris Top, 
     Quilt Xcel, 
     Resource, 
     Rodeo, 
     Select Max, 
     Showdown, 
     Stratego YLD, 
     TapOut, 
     Tempest, 
     Touchdown CT2, 
     Touchdown Total SL, 
     Traxion SL, 
     Utilize, or 
     Viathon. 
     
       
         
           
               
               
               
               
               
             
               
                   
               
               
                   
                   
                 Active 
                   
                   
               
               
                 Product 
                 Type 
                 Ingredient(s) 
                 Fomesafen specific language 
                 Broad herbicide tank mix language 
               
               
                   
               
             
            
               
                 Accord 
                 herbicide 
                 glyphosate 
                 none 
                 This product may be used in tank mix 
               
               
                 Concentrate 
                   
                   
                   
                 combination with other herbicide 
               
               
                   
                   
                   
                   
                 products to broaden the spectrum of 
               
               
                   
                   
                   
                   
                 vegetation controlled. 
               
               
                 Accord XRT II 
                 herbicide 
                 glyphosate 
                 none 
                 For residual weed control or to 
               
               
                   
                   
                   
                   
                 broaden the weed control spectrum, 
               
               
                   
                   
                   
                   
                 tank mix this product with other 
               
               
                   
                   
                   
                   
                 herbicides. 
               
               
                 Authority First 
                 herbicide 
                 cloransulam- 
                 none 
                 Authority First DF Herbicide may be 
               
               
                 DF 
                   
                 methyl, 
                   
                 applied alone or in tank mix 
               
               
                   
                   
                 sulfentrazone 
                   
                 combination with other herbicides 
               
               
                   
                   
                   
                   
                 registered for . . . application to 
               
               
                   
                   
                   
                   
                 soybeans. 
               
               
                 Authority XL 
                 herbicide 
                 clorimuron ethyl, 
                 none 
                 Authority XL may be applied alone 
               
               
                   
                   
                 sulfentrazone 
                   
                 or in tank mix combinations with 
               
               
                   
                   
                   
                   
                 other registered soybean herbicides. 
               
               
                 Avaris 
                 fungicide 
                 azoxystrobin, 
                 none 
                 Avaris may be applied as a foliar 
               
               
                   
                   
                 propiconazole 
                   
                 spray in alternating spray programs 
               
               
                   
                   
                   
                   
                 or in tank mixes with other crop 
               
               
                   
                   
                   
                   
                 protection products. 
               
               
                 Axilo BZM 
                 nutritional 
                 Mn, Zn, B, Mo 
                 none 
                 Axilo BZM is compatible with a 
               
               
                   
                   
                   
                   
                 wide range of fertilizers and 
               
               
                   
                   
                   
                   
                 pesticides . . . Can form a stable mixture 
               
               
                   
                   
                   
                   
                 with glyphosate, other pesticides and 
               
               
                   
                   
                   
                   
                 foliar fertilizers. 
               
               
                 Axilo Mix 5 
                 nutritional 
                 Fe, Mn, Mg, Cu, 
                 none 
                 Axilo Mix 5 is compatible with a 
               
               
                   
                   
                 Zn, B, Mo 
                   
                 wide range of fertilizers and 
               
               
                   
                   
                   
                   
                 pesticides . . . 
               
               
                 Axilo Mn 
                 nutritional 
                 Mn 
                 none 
                 Axilo Mn is compatible with a wide 
               
               
                   
                   
                   
                   
                 range of fertilizers and pesticides . . . 
               
               
                 Cadet 
                 herbicide 
                 fluthiacet-methyl 
                 none 
                 Cadet is compatible with most 
               
               
                   
                   
                   
                   
                 commonly used herbicides, 
               
               
                   
                   
                   
                   
                 insecticides, fungicides, and spray 
               
               
                   
                   
                   
                   
                 adjuvants. 
               
               
                 Classic 
                 herbicide 
                 mcpa, 2,4-D, 
                 CLASSIC ® may be tank mixed 
               
               
                   
                   
                 Dicamba 
                 with: 0.75-1.25 pt/acre “Flexstar” 
               
               
                   
                   
                   
                 0.75-1.5 pt/acre “Reflex” . . . 
               
               
                 Cobalt 
                 insecticide 
                 chlorpyrifos, 
                 none 
                 Cobalt Advanced is compatible with 
               
               
                   
                   
                 gamma, 
                   
                 insecticides, herbicides, miticides, 
               
               
                   
                   
                 cyhalothrin 
                   
                 and fungicides and non-pressure 
               
               
                   
                   
                   
                   
                 fertilizer solutions commonly used 
               
               
                   
                   
                   
                   
                 except for alkaline materials . . . 
               
               
                 Cobra 
                 herbicide 
                 lactofen 
                 TO DELAY HERBICIDE 
               
               
                   
                   
                   
                 RESISTANCE Avoid the use of 
               
               
                   
                   
                   
                 herbicides that have a similar target 
               
               
                   
                   
                   
                 site mode of action in consecutive 
               
               
                   
                   
                   
                 years. Other Group 14 herbicides 
               
               
                   
                   
                   
                 (PPO inhibitors) include acifluorfen 
               
               
                   
                   
                   
                 (Ultra Blazer ®) and fomesafen 
               
               
                   
                   
                   
                 (Flexstar ®, Reflex ®). 
               
               
                 CoRoN 10-0-10B 
                 nutritional 
                 Cl, N, Potash, B 
                 none 
                 none 
               
               
                 CoRoN Full Bor 
                 nutritional 
                 N, B 
                 none 
                 Coron Full Bor is compatible with 
               
               
                   
                   
                   
                   
                 most pesticides and other 
               
               
                   
                   
                   
                   
                 fertilizers . . . 
               
               
                 CoRoN 25-0-0- 
                 nutritional 
                 N, B 
                 none 
                 none 
               
               
                 0.5B 
               
               
                 Durango DMA 
                 herbicide 
                 glyphosate 
                 To control emerged weeds as a 
               
               
                   
                   
                   
                 postemergence application, apply 
               
               
                   
                   
                   
                 this product in a tank mix 
               
               
                   
                   
                   
                 with . . . fomesafen (Flexstar) 
               
               
                   
                   
                   
                 to control emerged  Amaranthys   
               
               
                   
                   
                   
                 spp . . . To control emerged 
               
               
                   
                   
                   
                 ragweed species, apply this product 
               
               
                   
                   
                   
                 in a tank mix with . . . fomesafen 
               
               
                   
                   
                   
                 (Flexstar). 
               
               
                 ENC 
                 nutritional 
                 Potash, Phosphate, 
                 none 
                 Ele-Max Nutriend Concentrate is 
               
               
                   
                   
                 N, Cl, Fe, Cu, Mn, 
                   
                 compatible with most fungicides, 
               
               
                   
                   
                 Zn, B, Mo, Co 
                   
                 insecticides and herbicides . . . 
               
               
                 First Rate 
                 herbicide 
                 cloransulam- 
                 Tank Mix Options: For weeds not 
               
               
                   
                   
                 methyl 
                 listed for postemergence control 
               
               
                   
                   
                   
                 with FirstRate, the herbicides listed 
               
               
                   
                   
                   
                 below may be used per label 
               
               
                   
                   
                   
                 instructions: Flexstar, Reflex 
               
               
                 Fusilade DX 
                 herbicide 
                 fluazifop-p-butyl 
                 Tank Mix Options: For weeds not 
               
               
                   
                   
                   
                 listed for postemergence control 
               
               
                   
                   
                   
                 with FirstRate, the herbicides listed 
               
               
                   
                   
                   
                 below may be used per label 
               
               
                   
                   
                   
                 instructions: Flexstar, Reflex 
               
               
                 Gly Star Gold 
                 herbicide 
                 glyphosate 
                 Soybeans Refer to table below for 
               
               
                   
                   
                   
                 tank mixtures that may be applied 
               
               
                   
                   
                   
                 before, during or after planting in 
               
               
                   
                   
                   
                 conventional tillage systems, into a 
               
               
                   
                   
                   
                 cover crop, established sod or in 
               
               
                   
                   
                   
                 previous crop residue. TANK 
               
               
                   
                   
                   
                 MIXES: Flexstar, Reflex 
               
               
                 Glyfos Original 
                 herbicide 
                 glyphosate 
                 none 
                 none 
               
               
                 Glyfos Xtra 
                 herbicide 
                 glyphosate 
                 none 
                 none 
               
               
                 Glystar Plus 
                 herbicide 
                 glyphosate 
                 Soybeans Refer to table below for 
               
               
                   
                   
                   
                 tank mixtures that may be applied 
               
               
                   
                   
                   
                 before, during or after planting in 
               
               
                   
                   
                   
                 conventional tillage systems, into a 
               
               
                   
                   
                   
                 cover crop, established sod or in 
               
               
                   
                   
                   
                 previous crop residue. TANK 
               
               
                   
                   
                   
                 MIXES: Flexstar, Reflex 
               
               
                 Glytrel MnP 
                 nutritional 
                 Mn, phosphate 
                 none 
                 none 
               
               
                 Gramoxone 
                 herbicide 
                 paraquat 
                 Gramoxone SL may be tank 
               
               
                   
                   
                   
                 mixed with the following 
               
               
                   
                   
                   
                 herbicides: . . . Flexstar. 
               
               
                 Halex GT 
                 herbicide 
                 s-matolachlor, 
                 none 
                 none 
               
               
                   
                   
                 glyphosate, 
               
               
                   
                   
                 mesotrione 
               
               
                 Headline AMP 
                 fungicide 
                 metconazole, 
                 none 
                 none 
               
               
                   
                   
                 pyraclostrobin 
               
               
                 Headline EC 
                 fungicide 
                 pyraclostrobin 
                 none 
                 Headline fungicide can be tank mixed 
               
               
                   
                   
                   
                   
                 with most recommended fungicides, 
               
               
                   
                   
                   
                   
                 insecticides, herbicides, liquid 
               
               
                   
                   
                   
                   
                 fertilizers, biological control 
               
               
                   
                   
                   
                   
                 products, adjuvants, and additives as 
               
               
                   
                   
                   
                   
                 specified in table 2. 
               
               
                 Headline SC 
                 fungicide 
                 pyraclostrobin 
                 none 
                 Headline SC fungicide can be tank 
               
               
                   
                   
                   
                   
                 mixed with most recommended 
               
               
                   
                   
                   
                   
                 fungicides, insecticides, herbicides, 
               
               
                   
                   
                   
                   
                 liquid fertilizers, biological control 
               
               
                   
                   
                   
                   
                 products, adjuvants, and additives as 
               
               
                   
                   
                   
                   
                 specified in table 2. 
               
               
                 Honcho Plus 
                 herbicide 
                 glyphosate 
                 This product may also be tank- 
               
               
                   
                   
                   
                 mixed with the following 
               
               
                   
                   
                   
                 products . . . Flexstar, Reflex 
               
               
                 Hoss Ultra 
                 herbicide 
                 glyphosate 
                 none 
                 none 
               
               
                 Kickstand MN 
                 nutritional 
                 Mn 
                 none 
                 none 
               
               
                 K-Leaf 
                 nutritional 
                 Potash 
                 none 
                 none 
               
               
                 Leverage 2.7 
                 insecticide 
                 imidacloprid, 
                 none 
                 Leverage 2.7 may be combined with 
               
               
                   
                   
                 cyfluthrin 
                   
                 foliar-applied fungicides, herbicides 
               
               
                   
                   
                   
                   
                 and insecticides/miticides. 
               
               
                 Leverage 360 
                 insecticide 
                 imidacloprid, 
                 none 
                 Leverage 360 Insecticide may be 
               
               
                   
                   
                 cyfluthrin 
                   
                 combined with foliar-applied 
               
               
                   
                   
                   
                   
                 fungicides, herbicides and 
               
               
                   
                   
                   
                   
                 insecticides/miticides. 
               
               
                 Liberty 280 SL 
                 herbicide 
                 glufosinate 
                 TANKMIX PARTNER FOR 
               
               
                   
                   
                   
                 LIBERTY 280 SL HERBICIDE IN 
               
               
                   
                   
                   
                 LIBERTYLINK SOYBEANS 
               
               
                   
                   
                   
                 Flexstar, Reflex 
               
               
                 Marvel 
                 herbicide 
                 fomesafen, 
                 none 
                 Marvel Herbicide is compatible with 
               
               
                   
                   
                 fluthiacet-methyl 
                   
                 most commonly used herbicides, 
               
               
                   
                   
                   
                   
                 insecticides, fungicides, and spray 
               
               
                   
                   
                   
                   
                 adjuvants. 
               
               
                 Megafol 
                 nutritional 
                 Potash, N 
                 none 
                 Megafol can be tank mixed with 
               
               
                   
                   
                   
                   
                 pesticides, fertilizers or other 
               
               
                   
                   
                   
                   
                 chemicals. 
               
               
                 Nucleus 0-0-15 
                 nutritional 
                 Potash, Cl 
                 none 
                 none 
               
               
                 Paraquat 
                 herbicide 
                 paraquat 
                 Improved Control of Perennial and 
               
               
                 Firestorm 
                   
                   
                 Annual Broadleaf Weeds Tank 
               
               
                   
                   
                   
                 mixing with . . . Reflex Herbicide 
               
               
                   
                   
                   
                 will help improve control when 
               
               
                   
                   
                   
                 perennial broadleaf weeds such as 
               
               
                   
                   
                   
                 Canada thistle, bindweed, 
               
               
                   
                   
                   
                 dandelion, etc., or difficult to 
               
               
                   
                   
                   
                 control annual broadleaf weeds 
               
               
                   
                   
                   
                 such as giant ragweed or 
               
               
                   
                   
                   
                 morningglory are present. 
               
               
                 Pendimethalin 
                 herbicide 
                 pendimethalin 
                 none 
                 Helena Pendimethalin should be 
               
               
                   
                   
                   
                   
                 tank mixed or followed by a 
               
               
                   
                   
                   
                   
                 postemergence herbicide application. 
               
               
                 Powermax 
                 herbicide 
                 glyphosate 
                 This product may also be tank- 
               
               
                   
                   
                   
                 mixed with the following 
               
               
                   
                   
                   
                 products . . . Flexstar, Reflex, 
               
               
                   
                   
                   
                 fomesafen 
               
               
                 Prowl H2O 
                 herbicide 
                 pendimethalin 
                 none 
                 Prowl H2O should be tank mixed or 
               
               
                   
                   
                   
                   
                 followed by a postemergence 
               
               
                   
                   
                   
                   
                 herbicide application. 
               
               
                 Quadris Top 
                 fungicide 
                 azoxystrobin, 
                 none 
                 none 
               
               
                   
                   
                 difenconazole 
               
               
                 Quilt Xcel 
                 fungicide 
                 azoxystrobin, 
                 none 
                 Quilt Xcel may be applied as a foliar 
               
               
                   
                   
                 propiconazole 
                   
                 spray in alternating spray programs 
               
               
                   
                   
                   
                   
                 or in tank mixes with other crop 
               
               
                   
                   
                   
                   
                 protection products. 
               
               
                 Resource 
                 herbicide 
                 flumicloracm 
                 Approved tank mixes are indicated 
               
               
                   
                   
                 pentyl ester 
                 in Table 5 . . . Flexstar 
               
               
                 Rodeo 
                 herbicide 
                 glyphosate 
                 none 
                 For residual weed control or an 
               
               
                   
                   
                   
                   
                 alternate mode of action, tank mix 
               
               
                   
                   
                   
                   
                 this product with other herbicides. 
               
               
                 Select Max 
                 herbicide 
                 clethodim 
                 Table 10. SELECT MAX TANK 
               
               
                   
                   
                   
                 MIXES WITH BROADLEAF 
               
               
                   
                   
                   
                 HERBICIDES . . . Flexstar HL . . . 
               
               
                 Showdown 
                 herbicide 
                 glyphosate 
                 none 
                 Showdown may be applied in 
               
               
                   
                   
                   
                   
                 combination with any herbicide 
               
               
                   
                   
                   
                   
                 registered for the same site, timing, 
               
               
                   
                   
                   
                   
                 and method of application. 
               
               
                 Stratego YLD 
                 fungicide 
                 trifloxystrobin, 
                 none 
                 none 
               
               
                   
                   
                 prothioconazole 
               
               
                 TapOut 
                 herbicide 
                 clethodim 
                 Table 10. TAPOUT TANK MIXES 
               
               
                   
                   
                   
                 WITH BROADLEAF 
               
               
                   
                   
                   
                 HERBICIDES . . . Flexstar HL . . . 
               
               
                 Tempest 
                 insecticide 
                 bifenthrin, 
                 none 
                 Tempest Dual-Action Insecticide 
               
               
                   
                   
                 imidacloprid 
                   
                 may be applied in tank mixtures with 
               
               
                   
                   
                   
                   
                 other products approved for use on 
               
               
                   
                   
                   
                   
                 registered crops. 
               
               
                 Touchdown CT2 
                 herbicide 
                 glyphosate 
                 Touchdown CT2 can be tank mixed 
               
               
                   
                   
                   
                 with the following 
               
               
                   
                   
                   
                 products: . . . Flexstar, Reflex 
               
               
                 Touchdown Total 
                 herbicide 
                 glyphosate 
                 Touchdown Total can be tank 
               
               
                 SL 
                   
                   
                 mixed with the following 
               
               
                   
                   
                   
                 products: . . . Flexstar, Reflex 
               
               
                 Traxion SL 
                 herbicide 
                 glyphosate 
                 Traxion can be tank mixed with the 
               
               
                   
                   
                   
                 following products: . . . Flexstar, 
               
               
                   
                   
                   
                 Reflex 
               
               
                 Utilize 
                 nutritional 
                 N 
                 none 
                 none 
               
               
                 Viathon 
                 fungicide 
                 Potassium 
                 none 
                 none 
               
               
                   
                   
                 phosphite, 
               
               
                   
                   
                 tebuconazole 
               
               
                   
               
            
           
         
       
     
     The invention is applicable to all non-salt based fomesafen herbicides used in both agricultural and non-agricultural applications. Non-agricultural applications would include use in forestry, vegetation management, aquatics, ornamentals, turf, and home pest control. 
     The composition according to the invention can also contain 
     Macronutrients, 
     Micronutrients, 
     Humectants, 
     Inorganic acids, 
     Organic acids, 
     Various elements, which are normally drawn from the soil, are known to be essential to plant nutrition. These elements include: nitrogen (N), phosphorus (P), potassium (K), sulfur (S), calcium (Ca), magnesium (Mg), iron (Fe), manganese (Mn), copper (Cu), cobalt (Co), zinc (Zn), boron (B), nickel (Ni), molybdenum (Mo), and chlorine (Cl). Of these elements, nitrogen, phosphorus, potassium, sulfur, calcium, and magnesium are needed by plants in relatively large quantities and are therefore called macronutrients. The remaining members of the group (iron, manganese, copper, cobalt, zinc, boron, nickel, molybdenum, and chlorine) are known as micronutrients since they are required in very small amounts for plant growth. 
     Fertilizers can include macronutrients and micronutrients. 
     Supplying a plant&#39;s major nutrient needs (nitrogen, phosphorus, potassium-N—P—K) is most effective and economical via soil application. However, foliar application has proven to be an excellent method of supplying plant requirements for secondary macronutrients (sulfur, calcium, magnesium) and micronutrients (carbon (C), hydrogen (H), and oxygen (O), nitrogen (N), phosphorus (P) and potassium (K), while supplementing N—P—K needs for short and/or critical growth stage periods. Additionally, the so called micronutrients, also commonly provided by mineral fertilizers are: boron (B), chlorine (Cl), copper (Cu), iron (Fe), manganese (Mn), zinc (Zn) and molybdenum (Mo). Foliar application refers to the application of plant nutrients to above-ground plant parts. Foliar fertilization programs prolong the fertilizing application period, providing a continuous supply of nutrients when crop demand is at a maximum, and can be an economical way to boost yield. 
     In fertilization programs, sulfate metal salts (e.g., zinc sulfate, manganese sulfate, and copper sulfate) are an economical source affording both sulfur and micronutrients. 
     Humectants have also been used to help retain water within the soil and plant tissue. These features make the incorporation of a humectant into a foliar fertilizer potentially beneficial to the needs of the plant. Inorganic acids, include mineral acids selected from the group consisting of nitric acid, phosphoric acid, sulfuric acid, and mixtures thereof; and phosphorous acid or ammonia or a mixture thereof or phosphorous acid and/or ammonia can also be used in combination with the mineral acids. 
     Organic acids are preferably fulvic acid, humic acid, citric acid and carboxylic acid, preferably C 1  to C 20  carboxylic acid. 
     The composition(s) disclosed may be used in the range of 0.05-5.0% of water based spray. 
     EXAMPLES 
       
     
       
         
           
               
             
               
                 TABLE 1 
               
             
            
               
                   
               
               
                 Fomesafen % active at low and high range 
               
            
           
           
               
               
               
               
               
               
               
               
               
            
               
                   
                 Ex1 
                 Ex2 
                 Ex3 
                 Ex4 
                 Ex5 
                 Ex6 
                 Ex7 
                 Ex8 
               
               
                 Ingredient 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
               
               
                   
               
               
                 Fomesafen, non-salt form 
                 10.0 
                 10.0 
                 30.0 
                 30.0 
                 50.0 
                 50.0 
                 60.0 
                 70.0 
               
               
                 Fatty amine alkoxylate surfactants 
                 30.0 
                 70.0 
                 70.0 
                 — 
                 20.0 
                 30.0 
                 — 
                 — 
               
               
                 Alkanolamine surfactants 
                 — 
                 — 
                 — 
                 70.0 
                 30.0 
                 20.0 
                 40.0 
                 30.0 
               
               
                 Water balance 
                 60.0 
                 20.0 
                 — 
                 — 
                 — 
                 — 
                 — 
                 — 
               
               
                 Total 
                 100.0  
                 100.0  
                 100.0  
                 100.0  
                 100.0  
                 100.0  
                 100.0  
                 100.0  
               
               
                 Physical observations 
                 clear 
                 clear 
                 hazy 
                 clear 
                 clear 
                 clear 
                 clear 
                 lumpy 
               
               
                   
                 amber 
                 amber 
                 amber 
                 yellow 
                 amber 
                 amber 
                 amber 
                 yellow 
               
               
                   
                 liquid 
                 liquid 
                 liquid 
                 liquid 
                 liquid 
                 liquid 
                 liquid 
                 solids 
               
               
                 Soluble liquid 
                 yes 
                 yes 
                 yes 
                 yes 
                 yes 
                 yes 
                 yes 
                 no 
               
               
                   
               
            
           
         
       
     
     
       
         
           
               
             
               
                 TABLE 2 
               
             
            
               
                   
               
               
                 Single and combination surfactants 
               
            
           
           
               
               
               
               
               
               
               
               
               
               
            
               
                   
                 Ex9 
                 Ex10 
                 Ex11 
                 Ex12 
                 Ex13 
                 Ex14 
                 Ex15 
                 Ex16 
                 Ex17 
               
               
                 Ingredient 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
               
               
                   
               
               
                 Fomesafen, non-salt form 
                 10.0 
                 10.0 
                 30.0 
                 30.0 
                 30.0 
                 30.0 
                 30.0 
                 50.0 
                 50.0 
               
               
                 Alcohol alkoxylate 
                 — 
                 — 
                 20.0 
                 — 
                 — 
                 — 
                 — 
                 — 
                 — 
               
               
                 surfactants 
               
               
                 Alkanolamine surfactants 
                 — 
                 — 
                 20.0 
                 70.0 
                 — 
                 — 
                 — 
                 30.0 
                 20.0 
               
               
                 Fatty amine surfactants 
                 — 
                 — 
                 — 
                 — 
                 70.0 
                 — 
                 — 
                 — 
                 — 
               
               
                 Fatty amine alkoxylate 
                 20.0 
                 70.0 
                 30.0 
                 — 
                 — 
                 70.0 
                 — 
                 20.0 
                 30.0 
               
               
                 surfactants 
               
               
                 Alkoxylated quaternary 
                 — 
                 — 
                 — 
                 — 
                 — 
                 — 
                 70.0 
                 — 
                 — 
               
               
                 ammonium surfactants 
               
               
                 Water balance 
                 70.0 
                 20.0 
                 — 
                 — 
                 — 
                 — 
                 — 
                 — 
                 — 
               
               
                 Total 
                 100.0  
                 100.0  
                 100.0  
                 100.0  
                 100.0  
                 100.0  
                 100.0  
                 100.0  
                 100.0  
               
               
                 Physical observations 
                 clear 
                 clear 
                 clear 
                 clear 
                 hazy 
                 hazy 
                 clear 
                 clear 
                 clear 
               
               
                   
                 amber 
                 amber 
                 amber 
                 yellow 
                 amber 
                 amber 
                 amber 
                 amber 
                 amber 
               
               
                   
                 liquid 
                 liquid 
                 liquid 
                 liquid 
                 liquid 
                 liquid 
                 liquid 
                 liquid 
                 liquid 
               
               
                 Soluble liquid 
                 yes 
                 yes 
                 yes 
                 yes 
                 yes 
                 yes 
                 yes 
                 yes 
                 yes 
               
               
                   
               
            
           
         
       
     
     
       
         
           
               
             
               
                 TABLE 3 
               
             
            
               
                   
               
               
                 Preferred embodiment comparisons 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Ex18 
                 Ex19 
                 Ex20 
                 Ex21 
               
               
                 Ingredient 
                 wt % 
                 wt % 
                 wt % 
                 wt % 
               
               
                   
               
            
           
           
               
               
               
               
               
            
               
                 Fomesafen, non-salt 
                 29.00 
                 29.00 
                 29.00 
                 29.00 
               
               
                 form 
               
               
                 Fatty amine alkoxylate 
                 20.00 
                 — 
                 — 
                 — 
               
               
                 surfactants 
               
               
                 Alkanolamine 
                 11.75 
                 11.75 
                 11.75 
                 — 
               
               
                 surfactants 
               
               
                 Secondary surfactants 
                 12.65 
                 12.65 
                 — 
                 — 
               
               
                 Glycol &amp; water 
                 26.60 
                 46.60 
                 59.25 
                 71.00 
               
               
                 balance 
                   
               
               
                 Total 
                 100.00 
                 100.00  
                 100.00  
                 100.00  
               
               
                 Physical observations 
                 clear 
                 clear 
                 clear 
                 white foamy solids 
               
               
                   
                 amber 
                 amber 
                 yellow 
                 suspended in clear 
               
               
                   
                 liquid 
                 liquid 
                 liquid 
                 liquid above thick 
               
               
                   
                   
                   
                   
                 white sediment 
               
               
                 Soluble liquid 
                 yes 
                 yes 
                 yes 
                 no 
               
               
                   
               
            
           
         
       
     
     CONCLUSION 
     The data above clearly showed the criticality of selecting the correct surfactant so that the fomesafen can be soluble. It is demonstrated above that the surfactants being alkoxylated fatty amines (see examples 1-3, 5, 6, 9-11, 14, and 16-18 above), alkanolamines (examples 4-8, 11-12, and 16-20 above) and alkoxylated quaternary ammonium compounds (example 15) were unexpectedly superior with respect to being soluble and clear liquids. In addition, it is demonstrated above that the surfactants being fatty amines (example 13) produce a soluble but hazy liquid. Table 1 shows the use of different amounts of the active from 10 to 70%. It is noted that example 8 with 70% fomesafen did not work. Table 2 shows formulas with single and  0 combinations of different surfactants. Without the use of these surfactants the fomesafen would not solubilize. The above data shows that the use of certain surfactants with fomesafen produces a clear soluble liquid. Examples 3, 13 and 14 worked but were not quite as good, being hazy but still soluble. Table 3 shows that the use of surfactants is critical, comparing an example with no surfactants (example 21) to examples with mixtures of surfactants (examples 18-20). 
     All the references described above are incorporated by reference in their entirety.