US20140128264A1 - Low volatility herbicidal compositions - Google Patents

Low volatility herbicidal compositions Download PDF

Info

Publication number
US20140128264A1
US20140128264A1 US14/071,927 US201314071927A US2014128264A1 US 20140128264 A1 US20140128264 A1 US 20140128264A1 US 201314071927 A US201314071927 A US 201314071927A US 2014128264 A1 US2014128264 A1 US 2014128264A1
Authority
US
United States
Prior art keywords
monocarboxylate
auxin herbicide
acceptable salt
agriculturally acceptable
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US14/071,927
Other languages
English (en)
Inventor
John W. Hemminghaus
Alison MacInnes
Daniel R. Wright
Junhua Zhang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Technology LLC
Original Assignee
Monsanto Technology LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Monsanto Technology LLC filed Critical Monsanto Technology LLC
Priority to US14/071,927 priority Critical patent/US20140128264A1/en
Publication of US20140128264A1 publication Critical patent/US20140128264A1/en
Assigned to MONSANTO TECHNOLOGY LLC reassignment MONSANTO TECHNOLOGY LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEMMINGHAUS, JOHN W., MACINNES, Alison, ZHANG, ZUNHUA, WRIGHT, DANIEL R.
Priority to US16/518,310 priority patent/US20200113179A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A01N37/04Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02Aryloxy-carboxylic acids; Derivatives thereof
    • A01N39/04Aryloxy-acetic acids; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • GPHYSICS
    • G09EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09BEDUCATIONAL OR DEMONSTRATION APPLIANCES; APPLIANCES FOR TEACHING, OR COMMUNICATING WITH, THE BLIND, DEAF OR MUTE; MODELS; PLANETARIA; GLOBES; MAPS; DIAGRAMS
    • G09B19/00Teaching not covered by other main groups of this subclass

Definitions

  • the present invention relates generally to low volatility herbicidal compositions comprising at least one auxin herbicide and at least one monocarboxylic acid, or monocarboxylate thereof.
  • the invention further relates generally to methods for preparing and using such low volatility herbicidal compositions, including methods for controlling auxin-susceptible plant growth on agricultural and non-agricultural lands.
  • auxin herbicides such as dicamba (3,6-dichloro-2-methoxybenzoic acid) and 2,4-D (2,4-dichlorophenoxyacetic acid), are commonly used to control auxin-susceptible plant growth on both agricultural and non-agricultural lands. Volatility and drift, however, are problems frequently associated with these herbicides. Volatile auxin herbicides can, under certain application conditions, vaporize into the surrounding atmosphere and migrate from the application site to adjacent crop plants, such as soybeans and cotton, where contact damage to sensitive plants can occur. Spray drift can be attributed to both volatility and the physical movement of small particles from the target site to adjacent crop plants.
  • auxin herbicide volatility has focused on encapsulation, for example, absorbing the auxin herbicide into solid phase natural or synthetic polymer, or microencapsulating the auxin herbicide in a polymer shell. Due to technological challenges and other factors, however, commercial encapsulation products that satisfactorily reduce auxin herbicide volatility have not been developed.
  • auxin herbicide compositions having reduced volatility relative to currently available compositions would be desirable, particularly reduced-volatility compositions that exhibit no significant reduction in herbicidal effectiveness relative to currently available compositions.
  • the present invention provides herbicidal compositions comprising at least one auxin herbicide; at least one monocarboxylic acid, or agriculturally acceptable monocarboxylate thereof; and, optionally, a non-auxin herbicide; wherein the compositions exhibit reduced volatility relative to an otherwise identical composition lacking the monocarboxylic acid or monocarboxylate thereof.
  • the auxin herbicide is selected from dicamba, or a agriculturally acceptable salt or ester thereof, and 2,4-D, or an agriculturally acceptable salt of ester thereof.
  • the composition comprises an acetate salt.
  • the non-auxin herbicide is glyphosate, or an agriculturally acceptable salt thereof.
  • the invention provides a herbicidal adjuvant composition
  • a herbicidal adjuvant composition comprising a monocarboxylic acid, or monocarboxylate thereof, and, optionally, an alkali metal phosphate, that can serve as the source of monocarboxylic acid, or a monocarboxylate thereof, used in the preparation of the herbicidal compositions of the present invention.
  • the invention provides methods of reducing the volatility of an auxin herbicide, wherein the methods comprise the step of contacting an auxin herbicide with a volatility-lowering effective amount of a monocarboxylic acid, or a monocarboxylate thereof, thereby reducing the volatility of the auxin herbicide.
  • the invention provides methods of controlling the growth of auxin-susceptible plants, wherein the methods comprise applying to the auxin-susceptible plants a herbicidal composition application mixture comprising at least one auxin herbicide; at least one monocarboxylic acid, or monocarboxylate thereof; and, optionally, a non-auxin herbicide; wherein the application mixture exhibits reduced auxin herbicide volatility relative to an otherwise identical application mixture lacking the monocarboxylic acid, or monocarboxylate thereof.
  • the invention provides methods of controlling off-site movement of an auxin herbicide, wherein the methods comprise contacting the auxin herbicide with a volatility-lowering effective amount of a monocarboxylic acid, or a monocarboxylate thereof, prior to application of the auxin herbicide.
  • the invention provides methods of counseling an individual regarding the preparation and/or application of an auxin herbicide.
  • the present invention provides herbicidal compositions comprising an auxin herbicide wherein the compositions exhibit reduced volatility and/or vapor drift upon application with respect to the auxin herbicide.
  • the compositions comprise, in addition to the auxin herbicide, at least one monocarboxylic acid, or monocarboxylate thereof, in an amount sufficient to reduce the volatility of the auxin herbicide relative to an otherwise identical composition lacking the monocarboxylic acid, or monocarboxylate thereof.
  • a sufficient amount of a monocarboxylic acid, or a monocarboxylate thereof (particularly a non-ammoniated monocarboxylate salt), to a herbicidal composition concentrate or a herbicidal composition application mixture results in a significant reduction in the level of volatile auxin herbicide detected.
  • the amount of volatile auxin herbicide present is actually below the detection level of sophisticated analytical methods such as liquid chromatography-mass spectrometry (LC/MS).
  • LC/MS liquid chromatography-mass spectrometry
  • the compositions of the present invention provide enhanced protection from off-target crop injury while maintaining comparable herbicidal efficacy on auxin-susceptible plants located in the target area.
  • the present invention is additionally directed to methods for controlling the growth of auxin-susceptible plants, comprising applying the herbicidal compositions of the present invention to such plants in accordance with the guidance provided below.
  • auxin herbicide refers to a herbicide that functions as a mimic of an auxin plant growth hormone, thereby affecting plant growth regulation.
  • auxin herbicides that are suitable for use in the herbicidal compositions of the present invention include, without limitation, benzoic acid herbicides, phenoxy herbicides, pyridine carboxylic acid herbicides, pyridine oxy herbicides, pyrimidine carboxy herbicides, quinoline carboxylic acid herbicides, and benzothiazole herbicides.
  • auxin herbicides include:
  • the herbicidal composition comprises dicamba, or an agriculturally acceptable salt or ester thereof.
  • suitable dicamba salts include the N,N-bisdaminopropylimethylamine, monoethanolamine, dimethylamine (e.g., BANVEL®, ORACLE®, etc.), isopropylamine, diglycolamine (e.g., CLARITY®, VANQUISH®, etc.), potassium, and sodium salts, and combinations thereof.
  • Commercially available sources of dicamba, and its agriculturally acceptable salts include those products sold under the trade names BANVEL®, CLARITY®, DIABLO®, DISTINCT, ORACLE®, VANQUISH®, and VISION®.
  • the herbicidal composition comprises an agriculturally acceptable dicamba salt, wherein the salt is selected from the group consisting of N,N-bis-[aminopropyl]methylamine, monoethanolamine, dimethylamine, isopropylamine, diglycolamine, potassium, and sodium salts, and combinations thereof.
  • the herbicidal composition comprises 2,4-D, or an agriculturally acceptable salt or ester thereof.
  • suitable 2,4-D salts include the choline, dimethylamine, and isopropylamine salts, and combinations thereof.
  • suitable 2,4-D esters include the methyl, ethyl, propyl, butyl (2,4-DB), and isooctyl esters, and combinations thereof.
  • Commercially available sources of 2,4-D, and its agriculturally acceptable salts and esters include those products sold under the trade names BARRAGE®, FORMULA 40®, OPT-AMINE®, and WEEDAR 64®.
  • the herbicidal composition comprises an agriculturally acceptable 2,4-D salt, wherein the salt is selected from the group consisting of choline, dimethylamine, and isopropylamine salts, and combinations thereof.
  • the herbicidal composition comprises an agriculturally acceptable 2,4-D ester, wherein the ester is selected from the group consisting of butyl (i.e., 2,4-DB) and isooctyl esters, and combinations thereof.
  • the ester is selected from the group consisting of butyl (i.e., 2,4-DB) and isooctyl esters, and combinations thereof.
  • the herbicidal composition comprises at least two auxin herbicides, for example, dicamba, or an agriculturally acceptable salt or ester thereof, and 2,4-D, or an agriculturally acceptable salt or ester thereof.
  • “Monocarboxylic acid” refers to a hydrocarbon or substituted hydrocarbon containing only one carboxy functional group (i.e., R 1 —C(O)OH).
  • “Monocarboxylate” refers to a salt (i.e., R 1 —C(O)OM wherein M is an agriculturally acceptable cation) or ester (i.e., R 1 —C(O)OR 2 wherein R 2 is hydrocarbon or substituted hydrocarbon) of a monocarboxylic acid.
  • the composition comprises at least one monocarboxylate salt, which in aqueous compositions may be present, in whole or in part, in dissociated form as a monocarboxylate anion and the corresponding cation.
  • Representative monocarboxylic acids and monocarboxylates generally comprise a hydrocarbon or unsubstituted hydrocarbon selected from, for example, unsubstituted or substituted, straight or branched chain alkyl (e.g., C 1 -C 20 alkyl such as methyl, ethyl, n-propyl, isopropyl, etc.); unsubstituted or substituted, straight or branched chain alkenyl (e.g., C 2 -C 20 alkyl such as ethenyl, n-propenyl, isopropenyl, etc.); unsubstituted or substituted aryl (e.g., phenyl, hydroxyphenyl, etc.); or unsubstituted or substituted arylalkyl (e.g., benzyl).
  • straight or branched chain alkyl e.g., C 1 -C 20 alkyl such as methyl, ethyl,
  • the herbicidal composition comprises a monocarboxylate salt having the formula R 1 —C(O)OM, wherein R 1 is unsubstituted or substituted C 1 -C 10 alkyl and M is a non-ammoniated, agriculturally acceptable cation.
  • the herbicidal composition comprises a monocarboxylate salt having the formula R 1 —C(O)OM, wherein R 1 is unsubstituted C 1 -C 6 alkyl and M is an alkali metal salt.
  • the herbicidal composition comprises a monocarboxylate salt having the formula R 1 —C(O)OM, wherein R 1 is unsubstituted C 1 -C 3 alkyl and M is an alkali metal salt selected from sodium and potassium.
  • the monocarboxylate salt is potassium acetate.
  • the monocarboxylate salt is sodium acetate.
  • agriculturally acceptable salt refers to a salt comprising a cation that is known and accepted in the art for the formation of salts for agricultural or horticultural use.
  • the salt is a water-soluble salt.
  • the herbicidal compositions of the present invention optionally may further comprise an alkali metal phosphate such as dipotassium phosphate.
  • Dipotassium phosphate for example, can provide additional buffering and/or water-conditioning for aqueous herbicidal compositions of the present invention.
  • Dipotassium phosphate is particularly effective as a replacement for ammonium sulfate in herbicidal composition application mixtures prepared using hard water.
  • the herbicidal compositions of the present invention optionally may further comprise an alkali metal carbonate, such as potassium carbonate, to provide additional buffering and/or water-conditioning for aqueous herbicidal compositions of the present invention.
  • an alkali metal carbonate such as potassium carbonate
  • the herbicidal compositions of the present invention comprise an alkali metal phosphate. In other embodiments, the herbicidal compositions comprise an alkali metal carbonate. In still other embodiments, the herbicidal compositions comprise an alkali metal phosphate and an alkali metal carbonate.
  • the herbicidal compositions of the present invention optionally may further comprise conventional additives such as surfactants, drift reduction agents, safeners, solubility enhancing agents, thickening agents, flow enhancers, foam-moderating agents, freeze protectants, UV protectants, preservatives, antimicrobials, and/or other additives that are necessary or desirable to improve the performance, crop safety, or handling of the composition.
  • conventional additives such as surfactants, drift reduction agents, safeners, solubility enhancing agents, thickening agents, flow enhancers, foam-moderating agents, freeze protectants, UV protectants, preservatives, antimicrobials, and/or other additives that are necessary or desirable to improve the performance, crop safety, or handling of the composition.
  • the herbicidal composition comprises less than about 10 ppm of ammonium sulfate. In another embodiment, the herbicidal composition does not comprise ammonium sulfate.
  • the herbicidal composition does not comprise an acid that is a non-monocarboxylic acid.
  • the herbicidal compositions of the present invention optionally may further comprise at least one non-auxin herbicide.
  • non-auxin herbicide refers to a herbicide having a primary mode of action other than as an auxin herbicide.
  • Representative examples of non-auxin herbicides include acetyl CoA carboxylase (ACCase) inhibitors, acetolactate synthase (ALS) inhibitors, acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, photosystem I inhibitors, protoporphyrinogen oxidase (PPO or Protox) inhibitors, carotenoid biosynthesis inhibitors, enolpyruvyl shikimate-3-phosphate (EPSP) synthase inhibitor, glutamine synthetase inhibitor, dihydropteroate synthetase inhibitor, mitosis inhibitors, and nucleic acid inhibitors; salts and esters thereof; racemic mixtures and resolved isomers thereof; and combinations thereof.
  • ACCase inhibitors include clethodim, clodinafop, fenoxaprop-P, fluazifop-P, quizalofop-P, and sethoxydim.
  • ALS or AHAS inhibitors include flumetsulam, imazamethabenz-m, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, metsulfuron, prosulfuron, and sulfosulfuron.
  • photosystem I inhibitors include diquat and paraquat.
  • photosystem II inhibitors include atrazine, cyanazine, diuron, and metibuzin.
  • PPO inhibitors include acifluorofen, butafenacil, carfentrazone-ethyl, flufenpyr-ethyl, fluthiacet, flumiclorac, flumioxazin, fomesafen, lactofen, oxadiazon, oxyfluorofen, and sulfentrazone.
  • carotenoid biosynthesis inhibitors include aclonifen, amitrole, diflufenican, mesotrione, and sulcotrione.
  • EPSP inhibitor N-phosphonomethyl glycine (glyphosate).
  • a representative example of a glutamine synthetase inhibitor is glufosinate.
  • a representative example of a dihydropteroate synthetase inhibitor is asulam.
  • mitosis inhibitors include acetochlor, alachlor, dithiopyr, S-metolachlor, and thiazopyr.
  • nucleic acid inhibitors include difenzoquat, fosamine, metham, and pelargonic acid.
  • the herbicidal compositions of the present invention further comprise a non-auxin herbicide selected from the group consisting of acetochlor, glyphosate, glufosinate, flumioxazin, fomesafen, and agriculturally acceptable salts thereof.
  • a non-auxin herbicide selected from the group consisting of acetochlor, glyphosate, glufosinate, flumioxazin, fomesafen, and agriculturally acceptable salts thereof.
  • the herbicidal compositions of the present invention further comprise glyphosate, or an agriculturally acceptable salt thereof.
  • Suitable glyphosate salts include, for example, the ammonium, diammonium, dimethylammonium, monoethanolamine, isopropylamine, and potassium salts, and combinations thereof.
  • the glyphosate salts are selected from the group consisting of monoethanolamine, isopropylamine, and potassium salts, and combinations thereof.
  • the herbicidal compositions of the present invention comprise dicamba, or an agriculturally acceptable salt or ester thereof, and glyphosate, or an agriculturally acceptable salt thereof.
  • the herbicidal compositions of the present invention comprise dicamba, or an agriculturally acceptable salt thereof; glyphosate, or an agriculturally acceptable salt thereof; and a non-ammoniated, agriculturally acceptable acetate salt.
  • Commercially available sources of glyphosate, and its agriculturally acceptable salts include those products sold under the trade names DURANGO® DMA®, HONCHO PLUS®, ROUNDUP POWERMAX®, ROUNDUP WEATHERMAX®, TRAXION®, and TOUCHDOWN®.
  • the herbicidal compositions of the present invention comprise 2,4-D, or an agriculturally acceptable salt or ester thereof, and glyphosate, or an agriculturally acceptable salt thereof.
  • the herbicidal compositions of the present invention comprise 2,4-D, or an agriculturally acceptable salt or ester thereof; glyphosate, or an agriculturally acceptable salt thereof; and a non-ammoniated, agriculturally acceptable acetate salt.
  • Suitable amounts, concentrations, and/or molar ratios of the auxin herbicide, monocarboxylic acid, or monocarboxylate thereof, and optional non-auxin herbicide and non-herbicide additive components of the herbicidal compositions of the present invention will depend to some extent upon whether the composition is a ready-to-use composition, a concentrate to be diluted with water prior to application (e.g., a “premix”), or a herbicidal composition prepared by combining two or more herbicide components, water, and, optionally, other non-herbicide components (e.g., a “tank mix”).
  • Concentrated herbicidal compositions of the present invention typically comprise on an acid equivalent basis (a.e.), for example, from about 120 to about 600 g a.e./L, from about 300 to about 600 g a.e./L, from about 350 to about 600 g a.e./L, from about 400 to about 600 g a.e./L, from about 450 to about 600 g a.e./L, or from about 500 to about 600 g a.e./L total herbicide loading.
  • a.e. acid equivalent basis
  • Additional examples of representative total herbicide loading include 120, 150, 200, 250, 300, 350, 400, 450, 500, 550, and 600 g a.e./L, and ranges thereof (i.e., from about 120 to about 150 g a.e./L, from about 150 to about 200 g a.e./L, from about 200 to about 250 g a.e./L, from about 250 to about 300 g a.e./L, from about 300 to about 350 g a.e./L, from about 350 to about 400 g a.e./L from about 400 to about 450 g a.e./L, from about 450 to about 500 g a.e./L, from about 500 to about 550 g a.e./L, from about 550 to about 600 g a.e./L total herbicide loading).
  • Ready-to-use herbicidal compositions and other herbicidal compositions of the present invention requiring no further processing prior to application typically will comprise on an acid equivalent basis (a.e.) from about 0.1 g a.e./L to about 50 g a.e./L total herbicide loading.
  • the weight ratio on an acid equivalent basis of the auxin herbicide to the non-auxin herbicide is typically no greater than about 50:1, for example, about 50:1, 25:1, 10:1, 5:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:5, about 1:10, or ranges thereof such as from about 50:1 to about 1:10, from about 50:1 to about 1:5, from about 50:1 to about 1:1, from about 50:1 to about 3:1, from about 50:1 to about 5:1, from about 50:1 to about 10:1, from about 25:1 to about 1:1, or from about 25:1 to about 3:1.
  • auxin herbicide For any given auxin herbicide, one skilled in the art can readily determine using routine experimentation a minimum concentration of auxin herbicide and a minimum ratio of auxin herbicide to any additional auxin herbicides and/or non-auxin herbicides contained in the herbicidal composition that is desirable for the intended application.
  • the concentration of volatilized auxin herbicide in the vapor phase surrounding a herbicidal composition comprising an auxin herbicide and a monocarboxylic acid, or monocarboxylate thereof, is less than the concentration of volatilized auxin herbicide in the vapor phase surrounding a reference composition lacking the monocarboxylic acid or monocarboxylate, but otherwise having the same composition.
  • the concentration of volatilized auxin herbicide in the vapor phase surrounding a herbicidal composition comprising an auxin herbicide and a monocarboxylic acid, or monocarboxylate thereof, is less than 90%, 80%, 70%, 60%, 50%, 40%, 30%, 20%, 10%, or 5% of the concentration of volatilized auxin herbicide in the vapor phase surrounding the reference composition lacking the monocarboxylate.
  • the herbicidal compositions of the present invention may comprise a single monocarboxylic acid, or monocarboxylate thereof, or a mixture of two or more monocarboxylic acids, or monocarboxylates thereof.
  • the monocarboxylic acid or monocarboxylate loading of the herbicidal composition generally will depend upon the auxin herbicide loading of the herbicidal composition, the salt form of the auxin herbicide, and the properties of any other components of the herbicidal composition, and will be an amount sufficient to reduce the volatility of the auxin herbicide relative to a reference composition lacking the monocarboxylic acid or monocarboxylate, but otherwise having the same composition.
  • the monoethanolamine and diethanolamine salts of dicamba are less volatile than the dimethylamine and isopropylamine salts of dicamba and the loading required for the less volatile salts may be less than the loading required for the more volatile salts.
  • the loading of the monocarboxylic acid, or monocarboxylate thereof can vary with the specific combination of auxin herbicide, optional non-auxin herbicide, and monocarboxylic acid, or monocarboxylate thereof.
  • the molar ratio of the auxin herbicide to the monocarboxylic acid, or monocarboxylate thereof is typically no less than about 1:10 and no greater than about 10:1.
  • Representative molar ratios of auxin herbicide acid equivalent (a.e.) to total monocarboxylic acid, or monocarboxylate thereof are, for example, from 1:10 to about 10:1, from about 1:5 to about 5:1, and from about 3:1 to about 1:3.
  • the molar ratio of auxin herbicide to monocarboxylic acid, or monocarboxylate thereof is about 1:1.
  • the molar ratio of the alkali metal phosphate to the monocarboxylic acid, or monocarboxylate thereof can range, for example, from about 1:5 to about 5:1, from about 3:1 to about 1:3, or from about 2:1 to about 1:2. In one embodiment, the molar ratio of alkali metal phosphate to monocarboxylic acid, or monocarboxylate thereof, is about 1:1.
  • the molar ratio of the alkali metal carbonate to the monocarboxylic acid, or monocarboxylate thereof can range, for example, from about 1:5 to about 5:1, from about 3:1 to about 1:3, or from about 2:1 to about 1:2. In one embodiment, the molar ratio of alkali metal carbonate to monocarboxylic acid, or monocarboxylate thereof, is about 1:1.
  • the herbicidal compositions can be presented in various forms depending upon the intended use and handling properties desired.
  • the herbicidal compositions of the present invention can be prepared in dry powder form or in liquid form, particularly aqueous solutions or dispersions.
  • aqueous as used in this application, however, is not intended to exclude the presence of non-aqueous (i.e., organic) solvents as long as water is present. Water is the predominant component of the ready-to-use compositions and tank mix compositions disclosed in this application.
  • composition presentations of the invention are the following:
  • a herbicidal composition concentrate that is diluted with water, and optionally combined with other herbicide and non-herbicide materials, prior to application (including, e.g., dry mixes and premixes);
  • a herbicidal composition application mixture prepared by diluting a herbicidal composition concentrate with water to form the herbicidal composition application mixture which then can be applied to auxin-susceptible plants;
  • a herbicidal composition application mixture prepared by combining two or more separate components with water (e.g., a tank mix) to form the herbicidal composition application mixture which then can be applied to auxin-susceptible plants;
  • a herbicidal composition application mixture prepared by introducing separate feed streams to a spraying or application system so that the feed streams are co-mixed to form the herbicidal composition application mixture immediately prior to use.
  • the herbicidal compositions (ready-to-use, liquid concentrate, tank mix, etc.) have a pH that is equal to or higher than the acid dissociation constant (pKa) of the monocarboxylic acid present in the composition.
  • the herbicidal compositions comprise acetic acid (which has a pKa of about 4.8) and have a pH equal to or greater than about 4.8.
  • dicamba volatility generally decreases as composition pH increases with dicamba volatility reaching substantially non-detectable levels at a composition pH of about 5.2 as measured in a plant response study.
  • the molar ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 10:1;
  • the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 5:1;
  • the concentrate contains an amount of the monocarboxylic acid, or
  • the concentration of the monocarboxylic acid, or monocarboxylate thereof is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L;
  • the concentrate comprises an amount of the monocarboxylic acid, or monocarboxylate thereof, sufficient to reduce the concentration of volatilized auxin herbicide in the vapor phase surrounding the concentrate by at least 10% relative to the concentration of volatilized auxin herbicide in the vapor phase surrounding an otherwise identical concentrate lacking the monocarboxylic acid, or monocarboxylate thereof.
  • the herbicidal composition concentrate comprises at least one auxin herbicide selected from the group consisting of dicamba, or an agriculturally acceptable salt or ester thereof, and 2,4-D, or an agriculturally acceptable salt or ester thereof.
  • the herbicidal composition concentrate comprises dicamba, or an agriculturally acceptable salt or ester thereof.
  • the concentrate comprises a dicamba salt selected from the group consisting of N,N-bis-[aminopropyl]methylamine, monoethanolamine, dimethylamine, isopropylamine, diglycolamine, potassium, and sodium salts, and combinations thereof.
  • the herbicidal composition concentrate comprises 2,4-D, or an agriculturally acceptable salt or ester thereof.
  • the concentrate comprises a 2,4-D salt selected from the group consisting of choline, dimethylamine, and isopropylamine salts, and combinations thereof.
  • the concentrate comprises a 2,4-D ester selected from the group consisting of butyl (i.e., 2,4-DB) and isooctyl esters, and combinations thereof.
  • the herbicidal composition concentrate comprises a monocarboxylate salt.
  • the herbicidal composition concentrate comprises a C 1 -C 6 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate comprises a C 1 -C 5 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate comprises a C 1 -C 4 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate comprises a C 1 -C 3 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate comprises acetic acid, or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate comprises formic acid, or an agriculturally acceptable salt thereof.
  • the monocarboxylate salt or acetate salt is a non-ammoniated salt.
  • the monocarboxylate salt or acetate salt is an alkali metal salt.
  • the monocarboxylate salt or acetate salt is a potassium salt.
  • the monocarboxylate salt or acetate salt is a sodium salt.
  • the herbicidal composition concentrate further comprises a buffer.
  • the herbicidal composition concentrate further comprises an alkali metal phosphate, such as dipotassium phosphate.
  • the herbicidal composition concentrate is a dry powder herbicidal composition.
  • the herbicidal composition concentrate is an aqueous herbicidal composition.
  • the herbicidal composition concentrate further comprises a non-auxin herbicide.
  • the non-auxin herbicide is selected from the group consisting of acetochlor, glyphosate, glufosinate, flumioxazin, fomesafen, and agriculturally acceptable salts thereof.
  • the non-auxin herbicide is glyphosate, or an agriculturally acceptable salt thereof.
  • the concentrate comprises a glyphosate salt selected from the group consisting of ammonium, diammonium, dimethylammonium, monoethanolamine, isopropylamine, and potassium salts, and combinations thereof.
  • the concentrate comprising a non-auxin herbicide satisfies one or more of the following conditions:
  • the sum of the concentration of Auxin herbicide and the concentration of non-auxin herbicide is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L;
  • the acid equivalent weight ratio of auxin herbicide to non-auxin herbicide is from about 1:5 to about 2:1;
  • the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 5:1.
  • composition satisfies one or more of the following conditions:
  • the molar ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 10:1;
  • the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 5:1;
  • the composition contains an amount of the monocarboxylic acid, or monocarboxylate thereof, from about 0.1% to about 25% by weight of the composition;
  • the concentration of the monocarboxylic acid, or monocarboxylate thereof is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L;
  • the composition comprises an amount of the monocarboxylic acid, or monocarboxylate thereof, sufficient to reduce the concentration of volatilized auxin herbicide in the vapor phase surrounding the composition by at least 10% relative to the concentration of volatilized auxin herbicide in the vapor phase surrounding an otherwise identical composition lacking the monocarboxylic acid, or monocarboxylate thereof.
  • the composition comprises at least one auxin herbicide selected from the group consisting of dicamba, or an agriculturally acceptable salt or ester thereof, and 2,4-D, or an agriculturally acceptable salt or ester thereof.
  • the composition comprises dicamba, or an agriculturally acceptable salt or ester thereof.
  • the composition comprises a dicamba salt selected from the group consisting of N,N-bis-[aminopropyl]methylamine, monoethanolamine, dimethylamine, isopropylamine, diglycolamine, potassium, and sodium salts, and combinations thereof.
  • the composition comprises 2,4-D, or an agriculturally acceptable salt or ester thereof.
  • the composition comprises a 2,4-D salt selected from the group consisting of choline, dimethylamine, and isopropylamine salts, and combinations thereof.
  • the composition comprises a 2,4-D ester such as 2,4-DB.
  • the composition comprises a monocarboxylate salt.
  • the herbicidal composition concentrate comprises a C 1 -C 6 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate comprises a C 1 -C 5 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate comprises a C 1 -C 4 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate comprises a C 1 -C 3 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate comprises acetic acid, or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate comprises formic acid, or an agriculturally acceptable salt thereof.
  • the monocarboxylate salt or acetate salt is a non-ammoniated salt.
  • the monocarboxylate salt or acetate salt is an alkali metal salt.
  • the monocarboxylate salt or acetate salt is a potassium salt.
  • the monocarboxylate salt or acetate salt is a sodium salt.
  • composition further comprises a buffer.
  • the herbicidal composition concentrate further comprises an alkali metal phosphate, such as dipotassium phosphate.
  • the composition is an aqueous herbicidal composition.
  • the composition further comprises a non-auxin herbicide.
  • the non-auxin herbicide is selected from the group consisting of acetochlor, glyphosate, glufosinate, flumioxazin, fomesafen, and agriculturally acceptable salts thereof.
  • the non-auxin herbicide is glyphosate, or an agriculturally acceptable salt thereof.
  • the concentrate comprises a glyphosate salt selected from the group consisting of ammonium, diammonium, dimethylammonium, monoethanolamine, isopropylamine, and potassium salts, and combinations thereof.
  • the concentrate comprising a non-auxin herbicide satisfies one or more of the following conditions:
  • the sum of the concentration of auxin herbicide and the concentration of non-auxin herbicide is from about 1 gram (acid equivalent weight)/L to about 50 grams (acid equivalent weight)/L;
  • the acid equivalent weight ratio of auxin herbicide to non-auxin herbicide is from about 1:5 to about 2:1; and the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 5:1.
  • compositions of particular interest include herbicidal compositions comprising dicamba, or an agriculturally acceptable salt or ester thereof; acetic acid, or an agriculturally acceptable salt thereof; and, optionally, glyphosate, or an agriculturally acceptable salt thereof.
  • molar ratio of acetic acid, or agriculturally acceptable salt thereof, to dicamba, or agriculturally acceptable salt or ester thereof is from about 1:10 to about 10:1.
  • the herbicidal composition concentrate comprises:
  • the acid equivalent weight ratio of acetic acid, or agriculturally acceptable salt thereof, to dicamba, or agriculturally acceptable salt or ester thereof is from about 1:10 to about 5:1.
  • the herbicidal composition concentrate comprises:
  • the concentrate contains an amount of the acetic acid, or agriculturally acceptable salt thereof, from about 0.25% to about 25% by weight of the concentrate.
  • the herbicidal composition concentrate comprises:
  • concentration of the acetic acid, or agriculturally acceptable salt thereof is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L.
  • the herbicidal composition concentrate comprises:
  • concentration of dicamba, or an agriculturally acceptable salt or ester thereof is from about 120 grams (acid equivalent weight)/L to about 600 grams
  • the herbicidal composition concentrate comprises:
  • concentration of dicamba, or an agriculturally acceptable salt or ester thereof is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L;
  • the acid equivalent weight ratio of acetic acid, or agriculturally acceptable salt thereof, to dicamba, or agriculturally acceptable salt or ester thereof is from about 1:10 to about 5:1.
  • the herbicidal composition concentrate comprises:
  • the concentrate comprises an amount of the acetic acid, or agriculturally acceptable salt thereof, sufficient to reduce the concentration of volatilized dicamba, or agriculturally acceptable salt or ester thereof, in the vapor phase surrounding the concentrate by at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 95% relative to the concentration of volatilized dicamba, or agriculturally acceptable salt or ester thereof, in the vapor phase surrounding an otherwise identical concentrate lacking the acetic acid, or agriculturally acceptable salt thereof.
  • the herbicidal composition concentrate comprises a dicamba salt selected from the group consisting of N,N-bis-[aminopropyl]methylamine, monoethanolamine, dimethylamine, isopropylamine, diglycolamine, potassium, and sodium salts, and combinations thereof.
  • a dicamba salt selected from the group consisting of N,N-bis-[aminopropyl]methylamine, monoethanolamine, dimethylamine, isopropylamine, diglycolamine, potassium, and sodium salts, and combinations thereof.
  • the herbicidal composition concentrate comprises an acetate salt.
  • the acetate salt is an alkali metal salt.
  • the acetate salt is a potassium salt.
  • the acetate salt is a sodium salt.
  • the herbicidal composition concentrate further comprises a buffer.
  • the herbicidal composition concentrate further comprises an alkali metal phosphate, such as dipotassium phosphate.
  • the herbicidal composition concentrate is a dry powder herbicidal composition.
  • the herbicidal composition concentrate is an aqueous herbicidal composition.
  • the herbicidal composition concentrate further comprises a non-auxin herbicide.
  • the non-auxin herbicide is selected from the group consisting of acetochlor, glyphosate, glufosinate, flumioxazin, fomesafen, and agriculturally acceptable salts thereof.
  • the concentrate comprising a non-auxin herbicide satisfies one or more of the following conditions:
  • the sum of the concentration of auxin herbicide and the concentration of non-auxin herbicide is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L;
  • the acid equivalent weight ratio of auxin herbicide to non-auxin herbicide is from about 1:5 to about 2:1;
  • the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 5:1.
  • molar ratio of acetic acid, or agriculturally acceptable salt thereof, to dicamba, or agriculturally acceptable salt or ester thereof is from about 1:10 to about 10:1.
  • the herbicidal composition concentrate comprises:
  • the acid equivalent weight ratio of acetic acid, or agriculturally acceptable salt thereof, to dicamba, or agriculturally acceptable salt or ester thereof is from about 1:10 to about 5:1.
  • the herbicidal composition concentrate comprises:
  • the concentrate contains an amount of the acetic acid, or agriculturally acceptable salt thereof, from about 0.25% to about 25% by weight of the concentrate.
  • the herbicidal composition concentrate comprises:
  • concentration of the acetic acid, or agriculturally acceptable salt thereof is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L.
  • the herbicidal composition concentrate comprises:
  • the sum of the concentration of dicamba, or an agriculturally acceptable salt or ester thereof, and the concentration of glyphosate, or an agriculturally acceptable salt thereof is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L.
  • the sum of the concentration of dicamba, or an agriculturally acceptable salt or ester thereof, and the concentration of glyphosate, or an agriculturally acceptable salt thereof is from about 360 grams (acid equivalent weight)/L to about 480 grams (acid equivalent weight)/L.
  • the herbicidal composition concentrate comprises:
  • the sum of the concentration of dicamba, or an agriculturally acceptable salt or ester thereof, and the concentration of glyphosate, or an agriculturally acceptable salt thereof is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L;
  • the acid equivalent weight ratio of dicamba, or an agriculturally acceptable salt or ester thereof, to glyphosate, or an agriculturally acceptable salt thereof is from about 1:5 to about 2:1.
  • the herbicidal composition concentrate comprises:
  • the sum of the concentration of dicamba, or an agriculturally acceptable salt or ester thereof, and the concentration of glyphosate, or an agriculturally acceptable salt thereof is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L;
  • the acid equivalent weight ratio of dicamba, or an agriculturally acceptable salt or ester thereof, to glyphosate, or an agriculturally acceptable salt thereof is from about 1:5 to about 2:1;
  • the acid equivalent weight ratio of acetic acid, or agriculturally acceptable salt thereof, to dicamba, or agriculturally acceptable salt or ester thereof is from about 1:10 to about 5:1.
  • the herbicidal composition concentrate comprises:
  • the concentrate comprises an amount of the acetic acid, or agriculturally acceptable salt thereof, sufficient to reduce the concentration of volatilized dicamba, or agriculturally acceptable salt or ester thereof, in the vapor phase surrounding the concentrate by at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 95% relative to the concentration of volatilized dicamba, or agriculturally acceptable salt or ester thereof, in the vapor phase surrounding an otherwise identical concentrate lacking the acetic acid, or agriculturally acceptable salt thereof.
  • the herbicidal composition concentrate comprises a dicamba salt selected from the group consisting of N,N-bis-[aminopropyl]methylamine, monoethanolamine, dimethylamine, isopropylamine, diglycolamine, potassium, and sodium salts, and combinations thereof.
  • a dicamba salt selected from the group consisting of N,N-bis-[aminopropyl]methylamine, monoethanolamine, dimethylamine, isopropylamine, diglycolamine, potassium, and sodium salts, and combinations thereof.
  • the herbicidal composition concentrate comprises an acetate salt.
  • the acetate salt is an alkali metal salt.
  • the acetate salt is a potassium salt.
  • the acetate salt is a sodium salt.
  • the herbicidal composition concentrate further comprises a buffer.
  • the herbicidal composition concentrate further comprises an alkali metal phosphate, such as dipotassium phosphate.
  • the herbicidal composition concentrate is a dry powder herbicidal composition.
  • the herbicidal composition concentrate is an aqueous herbicidal composition.
  • the concentrate comprises a glyphosate salt selected from the group consisting of ammonium, diammonium, dimethylammonium, monoethanolamine, isopropylamine, and potassium salts, and combinations thereof.
  • the concentrate satisfies one or more of the following conditions:
  • the sum of the concentration of dicamba, or agriculturally acceptable salt thereof, and the concentration of glyphosate, or agriculturally acceptable salt thereof, is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L;
  • the acid equivalent weight ratio of dicamba, or agriculturally acceptable salt thereof, to glyphosate, or agriculturally acceptable salt thereof is from about 1:5 to about 2:1;
  • the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to dicamba, or agriculturally acceptable salt thereof is from about 1:10 to about 5:1.
  • the herbicidal compositions correspond to the compositions described above in the “Illustrative Composition Embodiment (Application Mixture)” section wherein the auxin herbicide is dicamba, or an agriculturally acceptable salt or ester thereof.
  • the herbicidal compositions correspond to the compositions described above in the “Illustrative Composition Embodiment (Application Mixture)” section wherein the auxin herbicide is dicamba, or an agriculturally acceptable salt or ester thereof, and the compositions further comprise glyphosate, or an agriculturally acceptable salt or ester thereof.
  • compositions of particular interest also include herbicidal compositions comprising 2,4-D, or an agriculturally acceptable salt or ester thereof; acetic acid, or an agriculturally acceptable salt thereof; and, optionally, glyphosate, or an agriculturally acceptable salt thereof.
  • the herbicidal compositions correspond to the compositions described above in the “Illustrative Composition Embodiment (Dicamba Concentrate),” “Illustrative Composition Embodiment (Dicamba/Glyphosate Concentrate),” “Illustrative Composition Embodiment (Dicamba Application Mixture),” and “Illustrative Composition Embodiment (Dicamba/Glyphosate Application Mixture)” sections except that the dicamba, or agriculturally acceptable salt or ester thereof, is replaced with 2,4-D, or an agriculturally acceptable salt or ester thereof.
  • the methods of controlling the growth of auxin-susceptible plants involve the preparation of an application mixture by combining a source of auxin herbicide (e.g., CLARITY®); a source of monocarboxylic acid, or a monocarboxylate thereof; an optional source of non-auxin herbicide (e.g., DURANGO® or POWERMAX®); and water.
  • a source of auxin herbicide e.g., CLARITY®
  • a source of monocarboxylic acid, or a monocarboxylate thereof e.g., DURANGO® or POWERMAX®
  • non-auxin herbicide e.g., DURANGO® or POWERMAX®
  • Another embodiment of the present invention is directed to a herbicidal adjuvant composition
  • a herbicidal adjuvant composition comprising a monocarboxylic acid, or monocarboxylate thereof, and, optionally, an alkali metal phosphate, that can serve as the source of monocarboxylic acid, or a monocarboxylate thereof, used in the preparation of the application mixture.
  • the adjuvant composition for use in the preparation of the herbicidal composition application mixture comprises:
  • molar ratio of monocarboxylic acid, or monocarboxylate thereof, to alkali metal phosphate is from about 1:5 to about 5:1.
  • the adjuvant composition comprises a C 1 -C 6 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the adjuvant composition comprises a C 1 -C 5 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the adjuvant composition comprises a C 1 -C 4 alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the adjuvant composition comprises a C 1 -C 3 -alkanoic acid, or an agriculturally acceptable salt thereof. In other embodiments, the adjuvant composition comprises acetic acid, or an agriculturally acceptable salt thereof. In other embodiments, the adjuvant composition comprises formic acid, or an agriculturally acceptable salt thereof.
  • the adjuvant composition for use in the preparation of the herbicidal composition application mixture comprises:
  • composition contains an amount of the monocarboxylic acid, or monocarboxylate thereof, from about 2% to about 40% by weight of the composition.
  • the adjuvant composition for use in the preparation of the aqueous herbicidal application mixture comprises:
  • molar ratio of acetic acid, or agriculturally acceptable salt thereof, to alkali metal phosphate is from about 1:5 to about 5:1.
  • the adjuvant composition for use in the preparation of the aqueous herbicidal application mixture comprises:
  • molar ratio of acetic acid, or agriculturally acceptable salt thereof, to alkali metal phosphate is from about 1:5 to about 5:1;
  • composition contains an amount of the acetic acid, or agriculturally acceptable salt thereof, from about 2% to about 40% by weight of the composition.
  • the composition is a dry powder composition.
  • the composition is a liquid composition, particularly an aqueous composition.
  • the composition comprises a non-ammoniated monocarboxylate or acetate salt.
  • the salt is an alkali metal salt, such as an alkali metal salt.
  • the salt is a potassium salt or a sodium salt, such as potassium acetate and sodium acetate.
  • the alkali metal phosphate is dipotassium phosphate.
  • the composition comprises potassium acetate and dipotassium phosphate.
  • Another embodiment of the present invention is directed to a method of reducing the volatility of an auxin herbicide.
  • the method generally comprises the step of contacting an auxin herbicide with a volatility-lowering effective amount of a monocarboxylic acid, or a monocarboxylate thereof, thereby reducing the volatility of the auxin herbicide.
  • the contacting step satisfies at least one of the following conditions:
  • the molar ratio of the monocarboxylic acid, or monocarboxylate thereof, contacted with the auxin herbicide is from about 1:10 to about 10:1;
  • the acid equivalent weight ratio of the monocarboxylic acid, or monocarboxylate thereof, contacted with the auxin herbicide is from about 1:10 to about 5:1;
  • the amount of the monocarboxylic acid, or monocarboxylate thereof, contacted with the auxin herbicide is sufficient to reduce the concentration of volatilized auxin herbicide in the vapor phase by at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 95% relative to the concentration of volatilized auxin herbicide in the vapor phase for an auxin herbicide in the absence of the monocarboxylic acid, or monocarboxylate thereof.
  • Volatilization can be measured by conventional means known to those skilled in the art.
  • a gas stream is passed over an auxin herbicide composition and the auxin herbicide volatilizes from the composition into the gas stream which is then quantitatively analyzed for auxin herbicide content by methods known in the art.
  • an auxin herbicide composition is distilled and the distillation condensate and/or distilled composition is analyzed for auxin herbicide content.
  • auxin herbicide volatilization is qualitatively assessed in a plant response study on a chosen sensitive species which will be clear to one of skill in the art.
  • auxin herbicide effectiveness is observed for a herbicidal composition of the present invention relative to a reference composition lacking the monocarboxylic acid, or monocarboxylate thereof, but otherwise having the same composition.
  • the auxin herbicide effectiveness of a herbicidal composition of the present invention is at least about 80%, 85%, 90%, 95%, or 99% of the auxin herbicide effectiveness of a reference composition lacking the monocarboxylic acid, or monocarboxylate thereof, but otherwise having the same composition.
  • a reduced rate of crop injury is observed for a herbicidal composition of the present invention relative to a reference composition lacking the monocarboxylic acid, or monocarboxylate thereof, but otherwise having the same composition.
  • the rate of crop injury associated with a herbicidal composition of the present invention is less than about 90%, 80%, 70%, 60%, or 50% of the crop injury associated with a reference composition lacking the monocarboxylic acid, or monocarboxylate thereof, but otherwise having the same composition.
  • a reduction in the rate of crop injury and no reduction in auxin herbicide effectiveness are observed for the herbicidal compositions of the present invention relative to a reference composition lacking the monocarboxylic acid, or monocarboxylate thereof, but otherwise having the same composition.
  • the herbicidal composition loading of the monocarboxylic acid, or monocarboxylate thereof is sufficient to provide both commercially acceptable weed control and a commercially acceptable rate of crop injury.
  • a “commercially acceptable rate of weed control” varies with the weed species, degree of infestation, environmental conditions, and the associated crop plant. Typically, commercially effective weed control is defined as least about 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or even greater than 95%. Although it is generally preferable from a commercial viewpoint that 80-85% or more of the weeds be destroyed, commercially significant weed control can occur at much lower levels, particularly with some very noxious, herbicide-resistant plants.
  • “Weed control,” as used herein, refers to any observable measure of control of plant growth, which can include one or more of the actions of (1) killing, (2) inhibiting growth, reproduction or proliferation, and (3) removing, destroying, or otherwise diminishing the occurrence and activity of plants.
  • Weed control can be measured by any of the various methods known in the art. For example, weed control can be determined as a percentage as compared to untreated plants following a standard procedure wherein a visual assessment of plant mortality and growth reduction is made by one skilled in the art specially trained to make such assessments. In another control measurement method, control is defined as an average plant weight reduction percentage between treated and untreated plants. Preferably, commercial weed control is achieved at no greater than 30 days after treatment (DAT), such as from 18 to 30 DAT.
  • DAT days after treatment
  • a “commercially acceptable rate of crop injury” for the present invention likewise varies with the crop plant species. Typically, a commercially acceptable rate of crop injury is defined less than about 20%, 15%, 10% or even less than about 5%.
  • Crop damage can be measured by any means known in the art, such as those describe above for weed control determination. Preferably, crop damage appears no more than from 10% to 20% at no greater than 30 DAT, such as from 3 to 21 or from 3 to 30 DAT.
  • Another embodiment of the present invention is directed to methods of controlling the growth of auxin-susceptible plants, particularly those growing in and/or adjacent to a field of crop plants.
  • the methods generally comprise applying to the auxin-susceptible plants an aqueous herbicidal composition mixture comprising at least one auxin herbicide; at least one monocarboxylic acid, or monocarboxylate thereof; and, optionally, a non-auxin herbicide; wherein the application mixture exhibits reduced auxin herbicide volatility relative to an otherwise identical application mixture lacking the monocarboxylic acid, or monocarboxylate thereof.
  • the aqueous herbicidal composition mixture applied to the auxin-susceptible plants can be provided, for example, in the following manner:
  • herbicidal composition application mixture prepared by combining two or more separate components with water (e.g., a tank mix);
  • auxin-susceptible plants a herbicidal composition
  • a herbicidal composition comprising the auxin herbicide in admixture with the monocarboxylic acid, or monocarboxylate thereof.
  • the methods of controlling the growth of auxin-susceptible plants comprise the steps of:
  • the preparing step does not comprise separately introducing a pH-lowering agent (e.g., an acidifying agent) with the concentrate and water during the preparation of the application mixture; wherein the pH-lowering agent is one that is capable of lowering the pH of the application mixture in the absence of any buffering provided by other components of the application mixture.
  • a pH-lowering agent e.g., an acidifying agent
  • the methods of controlling the growth of auxin-susceptible plants comprise the steps of:
  • the molar ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 10:1;
  • the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 5:1;
  • composition contains an amount of the monocarboxylic acid, or
  • monocarboxylate thereof from about 0.1% to about 25% by weight of the composition
  • the concentration of the monocarboxylic acid, or monocarboxylate thereof is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L;
  • the application mixture comprises an amount of the monocarboxylic acid, or monocarboxylate thereof, sufficient to reduce the concentration of volatilized auxin herbicide in the vapor phase surrounding the application mixture by at least 10% relative to the concentration of volatilized auxin herbicide in the vapor phase surrounding an otherwise identical application mixture lacking the monocarboxylic acid, or monocarboxylate thereof.
  • the methods of controlling the growth of auxin-susceptible plants comprise the steps of:
  • the molar ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 10:1;
  • the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 5:1;
  • composition contains an amount of the monocarboxylic acid, or
  • monocarboxylate thereof from about 0.1% to about 25% by weight of the composition
  • the concentration of the monocarboxylic acid, or monocarboxylate thereof is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L;
  • the application mixture comprises an amount of the monocarboxylic acid, or monocarboxylate thereof, sufficient to reduce the concentration of volatilized auxin herbicide in the vapor phase surrounding the application mixture by at least 10% relative to the concentration of volatilized auxin herbicide in the vapor phase surrounding an otherwise identical application mixture lacking the monocarboxylic acid, or monocarboxylate thereof.
  • the application mixture generally satisfies one or more of the following conditions:
  • the sum of the concentration of auxin herbicide and the concentration of non-auxin herbicide is from about 1 gram (acid equivalent weight)/L to about 50 grams (acid equivalent weight)/L;
  • the acid equivalent weight ratio of auxin herbicide to non-auxin herbicide is from about 1:5 to about 2:1;
  • the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 5:1.
  • the application mixture comprises a non-auxin herbicide is selected from the group consisting of acetochlor, glyphosate, glufosinate, flumioxazin, fomesafen, and agriculturally acceptable salts thereof.
  • the application mixture comprises glyphosate, or an agriculturally acceptable salt thereof.
  • the auxin herbicide is selected from the group consisting of dicamba, or an agriculturally acceptable salt or ester thereof, and 2,4-D, or an agriculturally acceptable salt or ester thereof.
  • the auxin herbicide is dicamba, or an agriculturally acceptable salt or ester thereof.
  • the auxin herbicide is 2,4-D, or an agriculturally acceptable salt or ester thereof.
  • the application mixture comprises a monocarboxylate salt.
  • the application mixture comprises acetic acid, or an agriculturally acceptable salt thereof.
  • the monocarboxylate or acetate salt is a non-ammoniated salt.
  • the salt is an alkali metal salt.
  • the salt is a potassium salt.
  • the salt is a sodium salt.
  • the application mixture further comprises a buffer.
  • the application mixture further comprises an alkali metal phosphate, such as dipotassium phosphate.
  • the combining step does not comprise separately introducing a pH-lowering agent with the source of auxin herbicide; the source of monocarboxylic acid, or monocarboxylate thereof; and water during the preparation of the application mixture; wherein the pH-lowering agent is one that is capable of lowering the pH of the application mixture in the absence of any buffering provided by other components of the application mixture.
  • the combining step does not comprise separately introducing a pH-lowering agent with the source of auxin herbicide; the source of non-auxin herbicide; the source of monocarboxylic acid, or monocarboxylate thereof; and water during the preparation of the application mixture; wherein the pH-lowering agent is one that is capable of lowering the pH of the application mixture in the absence of any buffering provided by other components of the application mixture.
  • the application mixture is applied to the auxin-susceptible plants at an application rate sufficient to give a commercially acceptable rate of weed control.
  • the appropriate application rate for the application mixture can be readily determined by one of skill in the art and is usually expressed as amount of auxin herbicide per unit area treated, e.g., grams acid equivalent per hectare (g a.e./ha).
  • the period of time required to achieve a commercially acceptable rate of weed control can be as short as a week or as long as three weeks, four weeks, or one month. Typically, a period of about two to three weeks is needed for the auxin herbicide to exert its full effect.
  • the timing of application can vary.
  • the application mixture can be applied, for example, pre-planting of the crop plant, such as from about two to about three weeks before planting auxin-susceptible crop plants or crop plants not having a auxin herbicide-resistant trait. Crop plants that are not susceptible to certain auxin herbicides (such as corn or plants having an auxin herbicide-resistant trait), however, generally have no pre-planting restriction and the application mixture can be applied immediately before planting such crops.
  • the auxin-susceptible plants can be weeds or crop plants.
  • Crop plants include, for example, vegetable crops, grain crops, flowers, and root crops. Crop plants further encompass hybrids, inbreds, and transgenic or genetically modified plants.
  • the crop plants are auxin tolerant species that are not susceptible to auxin herbicides or are a transgenic species that contain an auxin (e.g., dicamba) resistant trait.
  • auxin e.g., dicamba resistant corn, cotton or soybean.
  • Dicamba resistant crops can further comprise one or more additional traits including, without limitation: herbicide resistance (e.g., resistance to other auxin herbicides (e.g., 2,4-D or fluoroxypyr), glyphosate, glufosinate, acetolactate synthase inhibitor herbicides (e.g., imazamox, imazethapyr, imazaquin and imazapic), acetyl CoA carboxylase inhibitors (e.g., sethoxydim and clethodim), etc.); insect resistance such as Bacillus thuringiensis (Bt); high oil; high lysine; high starch; nutritional density; and/or drought resistance.
  • Bt Bacillus thuringiens
  • the weeds and/or crop plants are glyphosate tolerant or contain a glyphosate resistant trait. Examples include glyphosate resistant corn, cotton or soybean.
  • the crop plants comprise stacked traits such as dicamba and glyphosate resistance; dicamba and glufosinate resistance; dicamba and acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) resistance; dicamba, glyphosate and glufosinate resistance; dicamba, glyphosate and ALS or AHAS resistance; dicamba, glufosinate and ALS or AHAS resistance; or dicamba, glyphosate, glufosinate and ALS or AHAS resistance.
  • stacked traits such as dicamba and glyphosate resistance; dicamba and glufosinate resistance; dicamba and acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) resistance; dicamba, glyphosate and glufosinate resistance; dicamba, glyphosate and ALS or AHAS resistance; or dicamba, glyphosate,
  • the plants can additionally include other herbicide, insect and disease resistance traits, as well as combinations of those traits.
  • the plants can have dicamba, 2,4-D, or fluoroxypyr resistant traits.
  • Another embodiment of the present invention is directed to a method of controlling off-site movement of an auxin herbicide by contacting the auxin herbicide with a volatility-lowering effective amount of a monocarboxylic acid, or a monocarboxylate thereof, prior to application of the auxin herbicide.
  • the method comprises the steps of:
  • the molar ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 10:1;
  • the acid equivalent weight ratio of monocarboxylic acid, or monocarboxylate thereof, to auxin herbicide is from about 1:10 to about 5:1;
  • the composition contains an amount of the monocarboxylic acid, or monocarboxylate thereof, from about 0.1% to about 25% by weight of the composition;
  • the concentration of the monocarboxylic acid, or monocarboxylate thereof is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L;
  • the application mixture comprises an amount of the monocarboxylic acid, or monocarboxylate thereof, sufficient to reduce the concentration of volatilized auxin herbicide in the vapor phase surrounding the application mixture by at least 10% relative to the concentration of volatilized auxin herbicide in the vapor phase surrounding an otherwise identical application mixture lacking the monocarboxylic acid, or monocarboxylate thereof.
  • Another embodiment of the present invention is directed to methods of counseling an individual regarding the preparation and/or application of an auxin herbicide.
  • the invention is directed to a method of counseling an individual on the application of an auxin herbicide to auxin-susceptible plants, the method comprising:
  • the invention is directed to a method of counseling an individual on the application of an auxin herbicide to auxin-susceptible plants, the method comprising:
  • the source of monocarboxylic acid, or a monocarboxylate thereof can be, for example, a single source such as the herbicidal composition adjuvant previously discussed, or even a source that provides for in situ formation of the monocarboxylic acid, or monocarboxylate thereof, in the herbicidal composition application mixture.
  • the herbicidal tank mix compositions listed in the tables below were prepared using CLARITY® (DGA dicamba from BASF), ROUNDUP POWERMAX® (potassium glyphosate from Monsanto), BANVEL® (DMA dicamba from BASF), DURANGO® DMA® (DMA glyphosate'e from Dow AgroSciences) and/or 2,4-D amine (Albaugh) by successively adding each specified herbicide to water and mixing.
  • CLARITY® DGA dicamba from BASF
  • ROUNDUP POWERMAX® potassium glyphosate from Monsanto
  • BANVEL® DMA dicamba from BASF
  • DURANGO® DMA® DMA glyphosate'e from Dow AgroSciences
  • 2,4-D amine Albaugh
  • tank mix formulations containing additional tank mix adjuvants such as potassium acetate (Sigma), dipotassium phosphate (ICL), and/or ammonium sulfate (Sigma) were typically prepared by adding aqueous stock solutions of the adjuvants to the herbicide mixture.
  • additional tank mix adjuvants such as potassium acetate (Sigma), dipotassium phosphate (ICL), and/or ammonium sulfate (Sigma) were typically prepared by adding aqueous stock solutions of the adjuvants to the herbicide mixture.
  • Herbicide salts not purchased from a commercial vendor such as IPA glyphosate and MEA dicamba, typically were prepared by mixing the herbicide acid with the desired amine.
  • the herbicide acid to amine ratio typically is about 1:1.
  • a slight excess of amine is desired.
  • DGA refers to diglycolamine
  • DMA refers to dimethylamine
  • IPA refers to isopropylamine
  • MEA refers to monoethanolamine.
  • Herbicidal tank mix compositions prepared by the method described above are listed in Tables 1-1 through 1-15 below:
  • composition 854-B INGREDIENT WT (g) WT % % ACTIVE DGA dicamba (CLARITY ®) 30.00 3.00% 1.20% ae ROUNDUP POWERMAX ® 60.60 6.06% 2.40% ae water 909.78
  • composition 751-E INGREDIENT WT (g) WT % % ACTIVE DGA dicamba (CLARITY ®) 7.51 3.00% 1.20% ae ROUNDUP POWERMAX ® 15.16 6.06% 2.40% ae ammonium sulfate (AMS) 7.35 2.94% 1.00% water 220.07
  • composition 751-D INGREDIENT WT (g) WT % % ACTIVE DGA dicamba (CLARITY ®) 7.49 3.00% 1.20% ae ROUNDUP POWERMAX ® 15.10 6.06% 2.40% ae potassium acetate (50%) 10.00 4.00% 2.00% ammonium sulfate (34%) 7.34 2.94% 1.00% water 210.07
  • composition 870-A INGREDIENT WT (g) WT % % ACTIVE DMA glyphosate (DURANGO ® 15.04 6.02% 2.40% ae DMA ®) 2,4-D amine 15.50 6.20% 2.40% ae water 219.54
  • composition 870-B INGREDIENT WT (g) WT % % ACTIVE DMA glyphosate (DURANGO ® 15.04 6.02% 2.40% ae DMA ®) 2,4-D amine 15.43 6.17% 2.40% ae potassium acetate (50%) 10.02 4.00% 2.00% water 209.57
  • composition 870-D INGREDIENT WT (g) WT % % ACTIVE IPA glyphosate (30.8%) 19.54 7.82 2.40% ae 2,4-D amine 15.42 6.17 2.40% ae water 215.04
  • the monocarboxylic acid salt e.g., potassium acetate
  • the compositions were prepared by mixing the herbicide(s) with water followed by addition of the monocarboxylic acid followed by addition of the neutralizing base.
  • the neutralizing base (potassium hydroxide in the compositions below) was added as a 45% w/w aqueous solution.
  • composition 854-A INGREDIENT WT (g) WT % % ACTIVE CLARITY ® 30.0 3.0 1.2% ae water
  • the potassium acetate used in the compositions in Tables 1-29 through Table 1-32 was prepared by adding the desired amount of glacial acetic acid to the desired amount of potassium hydroxide (45% w/w solution) in an ice bath without allowing the temperature of the solution to rise above 60° C. The pre-formed potassium acetate was then added to the solution containing the herbicide(s).
  • the ratio indicated in the tables below is on a molar basis. For example, “50/50 AcOH/KOH” means a 1:1 M ratio of acetic acid to potassium hydroxide.
  • the compositions in the tables below were prepared by adding the desired amount of each ingredient and stirring for about 20 minutes.
  • the monocarboxylic acid salt can be prepared by adding the monocarboxylic acid to the solution containing the herbicide(s) followed by addition of a neutralizing base.
  • a specific order of addition of the ingredients is not required to prepare the final composition, the order of addition described above can be advantageous to reduce the heat generation resulting when the ingredients are combined.
  • Herbicidal compositions containing DGA dicamba and MEA glyphosate were prepared by mixing CLARITY® with MEA glyphosate with water. After stirring the mixture for 5 minutes, surfactants AGM550 and Agnique PG8107-G were added followed by ferric citrate (for mitigating necrosis in certain crops) and anti-foaming agent SAG 1572, and the mixture stirred for an additional 30 minutes. Premix compositions which also contain additional adjuvants, such as potassium acetate, were prepared as described above with the modification of replacing the water with the desired amount of aqueous adjuvant.
  • additional adjuvants such as potassium acetate
  • the MEA glyphosate salt used in the preparation of the compositions was prepared by mixing glyphosate acid and 1.35 molar equivalents of MEA with water.
  • the list of ingredients of the dicamba/glyphosate premix composition is set forth in Table 2-1.
  • Dicamba/glyphosate premixes containing additional adjuvants typically were prepared by adding the desired amount of an aqueous solution of the adjuvant to the premix prepared as described in Tables 2-2 and 2-3 below.
  • the potassium acetate used in the formulations in Tables 2-5 through Table 2-13 was prepared by adding the desired amount of glacial acetic acid to the desired amount of potassium hydroxide (45% w/w solution) in an ice bath without allowing the temperature of the solution to rise above 60° C.
  • the ratio indicated in the tables below is on a molar basis.
  • 50/50 AcOH/KOH means a 1:1 M ratio of acetic acid to potassium hydroxide.
  • the compositions in the tables below were prepared by adding the desired amount of each ingredient and stirring for about 20 minutes.
  • the monocarboxylic acid salt can be prepared by adding the monocarboxylic acid to the solution containing the herbicide(s) followed by addition of a neutralizing base.
  • the Fe dopant in Tables 2-8 through 2-13 was prepared by mixing ferric sulfate and citric acid.
  • Humidomes obtained from Hummert International (Part Nos 14-3850-2 for humidomes and 11-3050-1 for 1020 flat tray) were modified by cutting a 2.2 cm diameter hole on one end approximately 5 cm from the top to allow for insertion of a glass air sampling tube (22 mm OD) containing a polyurethane foam (PUF) filter.
  • the sampling tube was secured with a VITON o-ring on each side of the humidome wall.
  • the air sampling tube external to the humidome was fitted with tubing that was connected to a vacuum manifold immediately prior to sampling.
  • the flat tray beneath the humidome was filled with 1 liter of sifted dry or wet 50/50 soil (50% Redi-Earth and 50% US 10 Field Soil) to a depth of about 1 cm.
  • the flat tray bottom containing the dicamba formulation on soil was covered with the humidome lid and the lid was secured with clamps.
  • the assembled humidomes were placed in a temperature and humidity controlled environment and connected to a vacuum manifold through the air sampling line. Air was drawn through the humidome and PUF at a rate of 2 liters per minute (LPM) for 24 hours at which point the air sampling was stopped.
  • the humidomes were then removed from the controlled environment and the PUF filter was removed.
  • the PUF filter was extracted with 20 mL of methanol and the solution was analyzed for dicamba concentration using LC-MS methods known in the art.
  • compositions were prepared to contain 1.2% a.e. dicamba which is equivalent to an application rate of 1.0 lb/A a.e. at 10 gallons per acre (GPA).
  • glyphosate was added or was part of the formulation, glyphosate was present at a concentration of 2.4% a.e. or 2.0 lb/A a.e.
  • 2,4-D was added or was part of the formulation, 2,4-D was present at 2.4% ae or 2.0 lb/A ae at 10 gallons per acre (GPA).
  • the growth chambers were set at 35° C. and 40% relative humidity (RH).
  • Table(s) 3-1 to 3-7 below provide the mean concentration of dicamba in air for each formulation. Where concentrations of dicamba were below the limits of detection, “nd” is indicated in the tables below.
  • Herbicidal compositions were sprayed onto eight 90 mm diameter glass Petri dishes.
  • the eight Petri dishes were placed immediately on a plastic tray along with two Roundup Ready soybean plants at V1-V1.5 development stage as indicators.
  • the plastic trays were then covered with plastic domes, sealed with clamps around edges, and placed in the growth chamber, at a set temperature and relative humidity (85° F. day (16 h light), 70° F. night (8 h dark) and 40% RH) for 24 hours. After 24 hours, the plants were removed from the domes and transferred to a greenhouse.
  • the indicator plants were evaluated for visual symptoms typically at 5, 7 and 14 days after treatment.
  • herbicidal effectiveness of the compositions of the present invention can be assessed through conventional greenhouse tests and/or field tests.
  • Herbicidal effectiveness can be measured as a percentage “inhibition” following a standard procedure in the art which reflects a visual assessment of plant mortality and growth reduction by comparison with untreated plants, made by technicians specially trained to make and record such observations. In all cases, a single technician makes all assessments of percent inhibition within any one experiment or trial. Such measurements are relied upon and regularly reported by Monsanto Technology LLC in the course of its herbicide business.
  • auxin herbicides are biologically effective for a specific auxin herbicide.
  • Useful application rates for the auxin herbicides employed can depend upon all of the above conditions. With respect to the use of the method of this invention, much information is known about appropriate auxin application rates, and a weed control practitioner can select auxin application rates that are herbicidally effective on particular species at particular growth stages in particular environmental conditions.
  • compositions of the present invention can be applied to plants by spraying, using any conventional means for spraying liquids, such as spray nozzles, atomizers, or the like.
  • Compositions of the present invention can be used in precision farming techniques, in which apparatus is employed to vary the amount of exogenous chemical applied to different parts of a field, depending on variables such as the particular plant species present, soil composition, and the like.
  • a global positioning system operated with the spraying apparatus can be used to apply the desired amount of the composition to different parts of a field.
  • composition at the time of application to plants, is preferably dilute enough to be readily sprayed using standard agricultural spray equipment.
  • Preferred application rates for the present invention vary depending upon a number of factors, including the type and concentration of active ingredient and the plant species involved.
  • Useful rates for applying an aqueous composition to a field of foliage can range from about 25 to about 1,000 liters per hectare (1/ha) by spray application.
  • the preferred application rates for aqueous solutions are in the range from about 50 to about 3001/ha.
  • exogenous chemicals including auxin herbicides
  • auxin herbicides must be taken up by living tissues of the plant and translocated within the plant in order to produce the desired biological (e.g., herbicidal) effect.
  • an herbicidal formulation not be applied in such a manner as to excessively injure and interrupt the normal functioning of the local tissue of the plant so quickly that translocation is reduced.
  • some limited degree of local injury can be insignificant, or even beneficial, in its impact on the biological effectiveness of certain exogenous chemicals.
  • the herbicidal tank mix compositions listed in the tables below were prepared using CLARITY® (DGA dicamba from BASF) and ROUNDUP POWERMAX® (potassium glyphosate from Monsanto) by successively adding each specified herbicide to water and mixing.
  • the tank mixtures containing potassium acetate were prepared as described in Example 1.
  • compositions were applied to the plants with a track sprayer generally using a Teejet 9501E flat fan nozzle or similar nozzle with air pressure set at a minimum of 24 pounds per square inch.
  • the spray nozzle was 16 inches above the top of the plants and a spray volume rate of approximately 10 gallons per acre (93 L per hectare) was applied.
  • Each composition was applied at three application rates and herbicide injury rating was made 21 days post treatment.
  • Herbicidal premix compositions listed in the tables below were prepared as previously described in Example 2.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Business, Economics & Management (AREA)
  • Entrepreneurship & Innovation (AREA)
  • Physics & Mathematics (AREA)
  • Educational Administration (AREA)
  • Educational Technology (AREA)
  • General Physics & Mathematics (AREA)
  • Theoretical Computer Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Toxicology (AREA)
US14/071,927 2012-11-05 2013-11-05 Low volatility herbicidal compositions Abandoned US20140128264A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US14/071,927 US20140128264A1 (en) 2012-11-05 2013-11-05 Low volatility herbicidal compositions
US16/518,310 US20200113179A1 (en) 2012-11-05 2019-07-22 Low volatility herbicidal compositions

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261722700P 2012-11-05 2012-11-05
US201361794769P 2013-03-15 2013-03-15
US14/071,927 US20140128264A1 (en) 2012-11-05 2013-11-05 Low volatility herbicidal compositions

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US16/518,310 Continuation US20200113179A1 (en) 2012-11-05 2019-07-22 Low volatility herbicidal compositions

Publications (1)

Publication Number Publication Date
US20140128264A1 true US20140128264A1 (en) 2014-05-08

Family

ID=49620302

Family Applications (6)

Application Number Title Priority Date Filing Date
US14/440,789 Active US9743664B2 (en) 2012-11-05 2013-11-05 Low volatility herbicidal compositions
US14/071,927 Abandoned US20140128264A1 (en) 2012-11-05 2013-11-05 Low volatility herbicidal compositions
US15/653,772 Active US10212933B2 (en) 2012-11-05 2017-07-19 Low volatility herbicidal compositions
US16/226,856 Active US11297834B2 (en) 2012-11-05 2018-12-20 Low volatility herbicidal compositions
US16/518,310 Pending US20200113179A1 (en) 2012-11-05 2019-07-22 Low volatility herbicidal compositions
US17/685,506 Pending US20220192192A1 (en) 2012-11-05 2022-03-03 Low volatility herbicidal compositions

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US14/440,789 Active US9743664B2 (en) 2012-11-05 2013-11-05 Low volatility herbicidal compositions

Family Applications After (4)

Application Number Title Priority Date Filing Date
US15/653,772 Active US10212933B2 (en) 2012-11-05 2017-07-19 Low volatility herbicidal compositions
US16/226,856 Active US11297834B2 (en) 2012-11-05 2018-12-20 Low volatility herbicidal compositions
US16/518,310 Pending US20200113179A1 (en) 2012-11-05 2019-07-22 Low volatility herbicidal compositions
US17/685,506 Pending US20220192192A1 (en) 2012-11-05 2022-03-03 Low volatility herbicidal compositions

Country Status (17)

Country Link
US (6) US9743664B2 (es)
EP (1) EP2914109A2 (es)
CN (2) CN108770849B (es)
AR (1) AR093356A1 (es)
AU (5) AU2013337293B2 (es)
BR (1) BR112015010067B1 (es)
CA (2) CA2889666C (es)
CL (3) CL2015001164A1 (es)
CR (1) CR20150231A (es)
HK (1) HK1214474A1 (es)
MX (2) MX352990B (es)
PH (2) PH12015500953A1 (es)
RU (1) RU2662779C2 (es)
UA (4) UA117002C2 (es)
UY (3) UY35114A (es)
WO (1) WO2014071374A2 (es)
ZA (2) ZA201502793B (es)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016112116A2 (en) 2015-01-06 2016-07-14 Monsanto Technology Llc Modulation of release rate from microencapsulated pesticides
WO2016124467A1 (en) * 2015-02-06 2016-08-11 Lamberti Spa Aqueous adjuvant concentrates with improved spray drift properties
WO2016124468A1 (en) * 2015-02-06 2016-08-11 Lamberti Spa Agrochemical adjuvant concentrate for herbicides
EP3092899A1 (en) * 2015-05-13 2016-11-16 multiBIND biotec GmbH Synergistic composition conatining herbicide, organic acid and surfactant
WO2018031610A1 (en) * 2016-08-09 2018-02-15 Monsanto Technology Llc Solid herbicidal concentrate compositions
WO2018162618A1 (en) 2017-03-08 2018-09-13 Rhodia Operations Low volatility herbicidal compositions
WO2018162621A1 (en) 2017-03-08 2018-09-13 Rhodia Operations Low volatility herbicidal compositions
WO2019143455A1 (en) * 2018-01-17 2019-07-25 Monsanto Technology Llc Herbicidal compositions
WO2019158601A1 (en) 2018-02-16 2019-08-22 Rhodia Operations Low volatility herbicidal compositions
EP3731635A4 (en) * 2017-12-22 2021-08-25 Monsanto Technology LLC HERBICIDE MIXTURES
US11419331B2 (en) 2019-01-30 2022-08-23 Monsanto Technology Llc Microencapsulated acetamide herbicides
EP4165989A1 (en) 2021-10-13 2023-04-19 Bayer CropScience LP Kit for preparing herbicidal application mixtures
EP4087398A4 (en) * 2020-01-10 2024-04-03 Monsanto Technology LLC HERBICIDAL COMPOSITIONS INCLUDING DRIFT INHIBITORS AND METHODS OF MANUFACTURING THE SAME
US12022827B2 (en) 2019-12-02 2024-07-02 The Board Of Trustees Of The University Of Arkansas Compositions and methods to reduce dicamba volatility and provide plant essential nutrients
EP4171224A4 (en) * 2020-06-29 2024-07-31 Monsanto Technology Llc AUXIN HERBICIDE AND L-GLUFOSINATE MIXTURES

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2889666C (en) * 2012-11-05 2021-07-20 Monsanto Technology Llc Low volatility herbicidal compositions comprising an auxin herbicide and a monocarboxylic acid or monocarboxylate thereof
IT201900006852A1 (it) 2019-05-15 2020-11-15 Torino Politecnico Formulazione ecocompatibile per ridurre volatilità e dilavamento di pesticidi
UY39009A (es) 2020-01-10 2021-08-31 Monsanto Technology Llc Composiciones herbicidas que incluyen agentes retardantes de la deriva y métodos de preparación de las mismas
US20230021295A1 (en) * 2021-06-30 2023-01-19 Ethox Chemicals, Llc Synergistic Combinations for Reducing Volatility of Auxin Herbicides
AU2023274686A1 (en) * 2022-05-25 2024-07-18 Sumitomo Chemical Company, Limited Liquid agrochemical composition

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020160916A1 (en) * 2001-02-20 2002-10-31 Greg Volgas Agricultural formulation
US20100248963A1 (en) * 2009-02-13 2010-09-30 Monsanto Technology Llc Encapsulation of Herbicides to Reduce Crop Injury

Family Cites Families (64)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE632909A (es) 1962-05-29
CN1010941B (zh) * 1984-11-26 1990-12-26 山道士有限公司 含有麦草畏新盐的除草剂产品及其制备方法
US5035738A (en) 1988-12-23 1991-07-30 Sandoz Ltd. Aminopropylmorpholine salts, compositions and uses thereof
NZ231897A (en) * 1988-12-30 1992-09-25 Monsanto Co Dry water-soluble granular composition comprising glyphosate and a liquid surfactant
US5683959A (en) 1991-01-08 1997-11-04 Mycogen Corporation Process and composition for controlling weeds
CA2100339A1 (en) * 1991-01-24 1992-07-25 Erhard John Prill Glyphosate formulations
CA2148840A1 (en) 1992-11-06 1994-05-26 Jim F. Stewart Dry water-dispersible glyphosate phytoactive formulation
US5389598A (en) 1993-12-17 1995-02-14 Monsanto Company Aqueous concentrate formulations having reduced eye irritancy
JPH0930908A (ja) * 1995-07-19 1997-02-04 Sumitomo Chem Co Ltd 除草剤組成物
US6586367B2 (en) * 1996-09-05 2003-07-01 Syngenta Crop Protection, Inc. Process for the control of weeds
CN1064035C (zh) * 1996-09-17 2001-04-04 裴圣镐 多元复合钛微肥
TW453855B (en) 1996-11-07 2001-09-11 Sankyo Co Plant growth regulator
US5877112A (en) 1997-08-27 1999-03-02 Helena Chemical Company Agricultural formulation
CN1191071A (zh) * 1998-03-23 1998-08-26 农业部全国农业技术推广服务中心江苏省农药研究所新沂农化实验基地 二氯喹啉酸悬浮剂
DE19815820A1 (de) 1998-04-08 1999-10-14 Hoechst Schering Agrevo Gmbh Synergistische herbizide Mittel auf Basis von phosphorhaltigen Blattherbiziden, Imidazolinonen und Wuchsstoffherbiziden
DE19836737A1 (de) * 1998-08-13 2000-02-17 Hoechst Schering Agrevo Gmbh Herbizide Mittel für tolerante oder resistente Maiskulturen
CA2872408C (en) 1998-08-13 2017-02-28 Bayer Cropscience Ag Herbicidal compositions comprising glyphosate for tolerant or resistant maize crops
US6432878B1 (en) 1999-01-15 2002-08-13 Cognis Corporation Adjuvant composition
WO2001026463A1 (en) 1999-10-13 2001-04-19 Nufarm Limited Adjuvant for a herbicidal composition
EP1457431A3 (en) * 1999-11-17 2007-07-04 Aquasol Limited Injection moulded water-soluble container
US6939555B2 (en) * 2000-01-21 2005-09-06 Helena Holding Company Manufacture and use of an deposition aid
US6541424B2 (en) 2000-08-07 2003-04-01 Helena Chemical Company Manufacture and use of a herbicide formulation
BR0207826A (pt) 2001-03-02 2004-06-22 Monsanto Technology Llc Composições pesticidas contendo ácido oxálico
ATE362314T1 (de) 2001-09-26 2007-06-15 Platte Chemical Co Herbizidzusammensetzungen umfassend imidazolinonsäure
US8138120B2 (en) 2003-03-11 2012-03-20 Cognis Ip Management Gmbh Microemulsions as adjuvants for agricultural chemicals
WO2005087007A1 (en) 2004-03-10 2005-09-22 Monsanto Technology Llc Herbicidal compositions containing n-phosphonomethyl glycine and an auxin herbicide
US8268749B2 (en) * 2004-09-17 2012-09-18 Monsanto Technology Llc Fast symptom glyphosate formulations
US8426341B2 (en) 2005-05-27 2013-04-23 Helena Holding Company Herbicide formulation
EP1844653B1 (en) 2006-03-30 2017-07-26 GAT Microencapsulation GmbH Novel agrochemical formulations containing microcapsules
CN101500421B (zh) * 2006-06-06 2015-04-15 孟山都技术有限公司 用于控制杂草的方法
NZ578197A (en) 2006-12-22 2012-05-25 Opal Australasia Pty Ltd Adjuvant composition containing ammonium sulfate and a surfactant
GB0703394D0 (en) * 2007-02-22 2007-03-28 Ciba Sc Holding Ag Process for Preparing and Applying Pesticide or Herbicide Formulation
CA2677979A1 (en) * 2007-02-26 2008-09-04 Dow Agrosciences Llc Ionic liquids derived from herbicidal carboxylic acids and certain trialkylamines or heteroarylamines
CN101932236A (zh) * 2007-11-07 2010-12-29 罗地亚管理公司 包含氨基磷酸盐或氨基膦酸盐和粘度降低剂的除草组合物
WO2009112836A2 (en) * 2008-03-12 2009-09-17 Syngenta Limited. Pickering emulsion formulations
AU2009289322C1 (en) 2008-09-04 2015-09-24 Akzo Nobel Chemicals International B.V. Viscoelastic system for drift reduction
PL2341778T3 (pl) * 2008-11-06 2014-06-30 Sn Biotech Tech Sp Z O O Sp K Ciekła, homogeniczna kompozycja herbicydowa, sposób zwalczania chwastów, sposób wytwarzania ciekłej, homogenicznej kompozycji herbicydu i zastosowanie ciekłej, homogenicznej kompozycji herbicydowej do zwalczania chwastów
US9192158B2 (en) * 2008-12-11 2015-11-24 Monsanto Technology Llc Herbicide formulations containing an etheramine and alkylamine alkoxylate surfactant system
JP5584452B2 (ja) 2008-12-11 2014-09-03 石原産業株式会社 ベンゾイルピラゾール系化合物を含有する除草性組成物
BRPI1011963A2 (pt) 2009-04-28 2015-12-01 Basf Corp composição praguicida espumável, método para controlar pragas, aplicador de praguicida
CN101564044B (zh) * 2009-05-19 2012-07-25 美丰农化有限公司 一种草甘膦铵盐可溶性粒剂及制备方法
JP2011001290A (ja) * 2009-06-18 2011-01-06 Sumitomo Chemical Co Ltd 雑草の防除方法
CN102480936B (zh) 2009-06-25 2015-03-25 陶氏益农公司 含有草甘膦盐和麦草畏盐的除草浓缩组合物
WO2011019652A2 (en) 2009-08-10 2011-02-17 Monsanto Technology Llc Low volatility auxin herbicide formulations
MX2012002726A (es) 2009-09-30 2012-04-11 Basf Se Sales de amina poco volatiles de pesticidas anionicos.
AU2010317610B2 (en) 2009-11-16 2015-05-14 Imtrade Australia Pty Ltd High load glyphosate formulations
US20130109572A1 (en) 2010-07-06 2013-05-02 The Board Of Trustees Of The University Of Alabama Herbicidal compositions and methods of use
CN102453631A (zh) * 2010-11-02 2012-05-16 郑州大学 医用液体多酶洗涤剂
EP2460404A1 (en) 2010-12-01 2012-06-06 Basf Se Compositions containing identical polyamine salts of mixed anionic pesticides
US20120238451A1 (en) * 2011-03-17 2012-09-20 Monsanto Technology Llc Herbicide and adjuvant compositions and method of use thereof
US8551533B2 (en) 2011-05-09 2013-10-08 Momentive Performance Materials Inc. Adjuvant composition and agrochemical formulation containing same
GB201115564D0 (en) * 2011-09-08 2011-10-26 Syngenta Ltd Herbicidal composition
US20130079228A1 (en) 2011-09-23 2013-03-28 Brian E. Freed Agricultural spray solution compositions and methods
BR102012027914A2 (pt) 2011-11-01 2016-01-26 Dow Agrosciences Llc grânulos com propriedades de dispersão aperfeiçoadas
JP6182165B2 (ja) 2012-03-05 2017-08-16 アーチャー−ダニエルズ−ミッドランド カンパニー マイクロエマルジョンおよび送達系としてのその使用
BR112014024517B8 (pt) 2012-04-02 2022-08-23 Dow Agrosciences Llc Composição de concentrado herbicida aquoso, e método para reduzir desvio de pulverização durante a aplicação de uma mistura de pulverização herbicida aquosa
CN103371160A (zh) * 2012-04-27 2013-10-30 龙灯农业化工国际有限公司 一种降低药物残留的农药组合物
GB201217281D0 (en) * 2012-09-27 2012-11-14 Microbe Secure Ltd Disinfectant formulation - MS71
CA2889666C (en) * 2012-11-05 2021-07-20 Monsanto Technology Llc Low volatility herbicidal compositions comprising an auxin herbicide and a monocarboxylic acid or monocarboxylate thereof
MX355884B (es) 2012-11-05 2018-05-02 Monsanto Technology Llc Mezclas herbicidas que contienen auxinas.
UY37356A (es) * 2016-08-09 2018-03-23 Monsanto Technology Llc Composiciones de concentrados herbicidas sólidos
EP3917319A4 (en) * 2019-01-30 2022-11-23 Monsanto Technology LLC MICROENCAPSULATED ACETAMIDE HERBICIDES
UY39009A (es) * 2020-01-10 2021-08-31 Monsanto Technology Llc Composiciones herbicidas que incluyen agentes retardantes de la deriva y métodos de preparación de las mismas
UY39010A (es) * 2020-01-10 2021-08-31 Monsanto Technology Llc Composiciones de herbicidas de auxina que incluyen agentes retardantes de la deriva y métodos de preparacion de las mismas

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020160916A1 (en) * 2001-02-20 2002-10-31 Greg Volgas Agricultural formulation
US20100248963A1 (en) * 2009-02-13 2010-09-30 Monsanto Technology Llc Encapsulation of Herbicides to Reduce Crop Injury

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11122798B2 (en) 2015-01-06 2021-09-21 Monsanto Technology Llc Modulation of release rate from microencapsulated pesticides
WO2016112116A2 (en) 2015-01-06 2016-07-14 Monsanto Technology Llc Modulation of release rate from microencapsulated pesticides
EP3666071A1 (en) 2015-01-06 2020-06-17 Monsanto Technology LLC Modulation of release rate from microencapsulated pesticides
US10638751B2 (en) 2015-01-06 2020-05-05 Monsanto Technology Llc Modulation of release rate from microencapsulated pesticides
WO2016124467A1 (en) * 2015-02-06 2016-08-11 Lamberti Spa Aqueous adjuvant concentrates with improved spray drift properties
WO2016124468A1 (en) * 2015-02-06 2016-08-11 Lamberti Spa Agrochemical adjuvant concentrate for herbicides
EP3092899A1 (en) * 2015-05-13 2016-11-16 multiBIND biotec GmbH Synergistic composition conatining herbicide, organic acid and surfactant
WO2016180857A1 (en) * 2015-05-13 2016-11-17 Multibind Biotec Gmbh Synergistic composition conatining herbicide, organic acid and surfactant
US11129388B2 (en) 2016-08-09 2021-09-28 Monsanto Technology Llc Solid herbicidal concentrate compositions
WO2018031610A1 (en) * 2016-08-09 2018-02-15 Monsanto Technology Llc Solid herbicidal concentrate compositions
WO2018162621A1 (en) 2017-03-08 2018-09-13 Rhodia Operations Low volatility herbicidal compositions
WO2018162618A1 (en) 2017-03-08 2018-09-13 Rhodia Operations Low volatility herbicidal compositions
US12070035B2 (en) * 2017-12-22 2024-08-27 Monsanto Technology Llc Herbicidal mixtures
EP3731635A4 (en) * 2017-12-22 2021-08-25 Monsanto Technology LLC HERBICIDE MIXTURES
CN111757671A (zh) * 2018-01-17 2020-10-09 孟山都技术有限公司 除草组合物
EP3740069A4 (en) * 2018-01-17 2022-01-19 Monsanto Technology LLC HERBICIDE COMPOSITIONS
WO2019143455A1 (en) * 2018-01-17 2019-07-25 Monsanto Technology Llc Herbicidal compositions
US12108760B2 (en) 2018-01-17 2024-10-08 Monsanto Technology Llc Herbicidal compositions
WO2019158601A1 (en) 2018-02-16 2019-08-22 Rhodia Operations Low volatility herbicidal compositions
US11419331B2 (en) 2019-01-30 2022-08-23 Monsanto Technology Llc Microencapsulated acetamide herbicides
US12022827B2 (en) 2019-12-02 2024-07-02 The Board Of Trustees Of The University Of Arkansas Compositions and methods to reduce dicamba volatility and provide plant essential nutrients
EP4087398A4 (en) * 2020-01-10 2024-04-03 Monsanto Technology LLC HERBICIDAL COMPOSITIONS INCLUDING DRIFT INHIBITORS AND METHODS OF MANUFACTURING THE SAME
EP4171224A4 (en) * 2020-06-29 2024-07-31 Monsanto Technology Llc AUXIN HERBICIDE AND L-GLUFOSINATE MIXTURES
EP4165989A1 (en) 2021-10-13 2023-04-19 Bayer CropScience LP Kit for preparing herbicidal application mixtures

Also Published As

Publication number Publication date
CA2889666A1 (en) 2014-05-08
RU2018126473A3 (es) 2022-04-06
EP2914109A2 (en) 2015-09-09
US11297834B2 (en) 2022-04-12
BR112015010067A2 (pt) 2017-07-11
AU2021200271B2 (en) 2023-03-02
US10212933B2 (en) 2019-02-26
CA3120042A1 (en) 2014-05-08
AU2023200861A1 (en) 2023-03-16
CL2018003223A1 (es) 2018-12-28
AR093356A1 (es) 2015-06-03
UA127001C2 (uk) 2023-03-01
CN104902746A (zh) 2015-09-09
ZA201502793B (en) 2021-08-25
US9743664B2 (en) 2017-08-29
CA2889666C (en) 2021-07-20
WO2014071374A3 (en) 2014-06-26
CN108770849A (zh) 2018-11-09
UY35114A (es) 2014-06-30
US20190191697A1 (en) 2019-06-27
AU2017219151B2 (en) 2019-01-17
US20170311593A1 (en) 2017-11-02
PH12015500953B1 (en) 2015-07-06
MX2015005650A (es) 2015-08-20
CA3120042C (en) 2024-02-27
BR112015010067B1 (pt) 2020-11-10
AU2019202005A1 (en) 2019-04-18
RU2018126473A (ru) 2018-10-02
AU2013337293B2 (en) 2017-06-15
UA125689C2 (uk) 2022-05-18
HK1214474A1 (zh) 2016-07-29
UY39816A (es) 2022-07-29
WO2014071374A2 (en) 2014-05-08
AU2017219151A1 (en) 2017-09-21
CL2015001164A1 (es) 2015-06-26
AU2021200271A1 (en) 2021-03-18
RU2662779C2 (ru) 2018-07-30
UY39817A (es) 2022-07-29
US20220192192A1 (en) 2022-06-23
RU2015121351A (ru) 2016-12-20
UA117002C2 (uk) 2018-06-11
ZA202101713B (en) 2022-07-27
CN108770849B (zh) 2022-07-08
UA118715C2 (uk) 2019-02-25
US20150264924A1 (en) 2015-09-24
US20200113179A1 (en) 2020-04-16
AU2013337293A1 (en) 2015-05-14
MX352990B (es) 2017-12-14
AU2019202005B2 (en) 2020-11-05
MX2020002546A (es) 2020-07-20
CR20150231A (es) 2015-05-29
CL2020000577A1 (es) 2020-09-11
CN104902746B (zh) 2018-09-21
PH12015500953A1 (en) 2015-07-06
PH12021551050A1 (en) 2022-02-21

Similar Documents

Publication Publication Date Title
US11297834B2 (en) Low volatility herbicidal compositions
AU2012328638B2 (en) Salts of carboxylic acid herbicides
US11452290B2 (en) Auxin herbicidal mixtures
US20240164377A1 (en) Low volatility promoting water conditioning adjuvants
RU2812197C1 (ru) Гербицидные композиции с низкой летучестью
RU2782274C2 (ru) Гербицидные композиции с низкой летучестью

Legal Events

Date Code Title Description
AS Assignment

Owner name: MONSANTO TECHNOLOGY LLC, MISSOURI

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HEMMINGHAUS, JOHN W.;MACINNES, ALISON;WRIGHT, DANIEL R.;AND OTHERS;SIGNING DATES FROM 20140903 TO 20140904;REEL/FRAME:033764/0763

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: FINAL REJECTION MAILED

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION