RU2812197C1 - Low volatility herbicide compositions - Google Patents

Abstract

FIELD: agriculture.

SUBSTANCE: invention relates to low volatility plant treatments. A combination package for preparing a herbicidal composition includes a first container containing dicamba or an agriculturally acceptable salt or ester thereof, and a second container containing acetic acid or an agriculturally acceptable salt thereof. The combination package further contains a third container containing glyphosate or an agriculturally acceptable salt thereof or glufosinate or an agriculturally acceptable salt thereof.

EFFECT: proposed combination package containing dicamba or an agriculturally acceptable salt or ester thereof and acetic acid or an agriculturally acceptable salt thereof provides a low volatility herbicidal composition without compromising the effectiveness of the herbicide.

9 cl, 100 tbl, 12 ex

Description

Cross reference to related applications

This application claims the benefit of US Provisional Application Serial No. 61/722700, filed November 5, 2012, and US Provisional Application Serial No. 61/794 7 6 9, filed March 15, 2013. The full text of said provisional applications is incorporated by reference in this application.

Field of technology to which the invention relates

The present invention relates generally to low volatility herbicidal compositions containing 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 inhibiting the growth of auxin-sensitive plants in agricultural and non-agricultural fields.

State of the art

Auxin herbicides such as dicamba (3,6-dichloro-2-methoxybenzoic acid) and 2,4-D (2,4-dichlorophenoxyacetic acid) are commonly used to suppress the growth of auxin-sensitive plants in both agricultural and non-agricultural fields . However, volatility and wind drift are problems often associated with these herbicides. Volatile auxin herbicides can, under certain application conditions, evaporate into the surrounding atmosphere and migrate from the site of application to adjacent crops such as soybeans and cotton, which can result in contact damage to sensitive plants. Spray drift can be attributed to both volatility and the physical movement of small particles from the target location to adjacent crop plants.

Previous approaches to reducing herbicide volatility have involved efforts to identify herbicide salts and formulations that have lower volatility. For example, dicamba diglycolamine salt has lower volatility than dicamba dimethylamine salt. Although lower volatility auxin herbicide salts and formulations have been described, it is still desirable to further reduce the volatility and movement of auxin herbicides away from the target.

Another approach to reducing the volatility of auxin herbicides has focused on encapsulation, such as absorption of the auxin herbicide into a solid phase natural or synthetic polymer, or microencapsulation of the auxin herbicide in a polymer shell. However, due to process requirements and other factors, commercial encapsulation products that satisfactorily reduce auxin herbicide volatility have not been developed.

Accordingly, auxin herbicide compositions that exhibit reduced volatility relative to currently available compositions, especially reduced volatility compositions that do not exhibit a significant reduction in herbicidal effectiveness relative to currently available compositions, may be desirable.

Brief description of the invention

In one aspect, the present invention relates to herbicidal compositions containing at least one auxin herbicide; at least one monocarboxylic acid or an agriculturally acceptable monocarboxylate thereof, and optionally a non-auxic herbicide, the compositions having reduced volatility relative to other identical compositions not containing the monocarboxylic acid or its monocarboxylate. In one embodiment, the auxin herbicide is selected from dicamba or an agriculturally acceptable salt or ester thereof and 2,4-D or an agriculturally acceptable salt or ester thereof. In one embodiment, the composition contains an acetate salt. In another embodiment, the non-auxin herbicide is glyphosate or an agriculturally acceptable salt thereof.

In another aspect, the invention provides a herbicidal adjuvant composition containing a monocarboxylic acid or a monocarboxylate thereof and optionally an alkali metal phosphate, which can serve as a source of the monocarboxylic acid or a monocarboxylate thereof used in the preparation of the herbicidal compositions of the present invention.

In another aspect, the invention provides methods for reducing the volatility of an auxin herbicide, wherein the methods include the step of contacting the auxin herbicide with a volatility-reducing amount of a monocarboxylic acid or a monocarboxylate thereof, thereby reducing the volatility of the auxin herbicide.

In another aspect, the invention relates to methods for inhibiting the growth of auxin-susceptible plants, wherein the methods include applying to the auxin-susceptible plants a mixture to apply a herbicidal composition containing at least one auxin herbicide; at least one monocarboxylic acid or a monocarboxylate thereof; and optionally a non-auxic herbicide, wherein the application mixture has reduced auxinic herbicide volatility compared to an identical application mixture not containing the monocarboxylic acid or its monocarboxylate.

In another aspect, the invention provides methods for controlling the movement of an auxinic herbicide from an application site, the methods comprising contacting the auxinic herbicide with a volatility-reducing effective amount of a monocarboxylic acid or a monocarboxylate thereof prior to application of the auxinic herbicide.

In another aspect, the invention relates to methods of advising an individual regarding the preparation and/or application of an auxin herbicide.

The following advantages of the present invention will be apparent to one skilled in the art upon reading this application. The embodiments described in the following paragraphs are intended to illustrate the invention, but should not be construed as limiting the scope of the invention.

Detailed Description of the Invention

The present invention relates to herbicidal compositions containing an auxinic herbicide, wherein the compositions have reduced volatility and/or reduced vapor displacement of the auxinic herbicide upon application. In particular, the compositions contain, in addition to the auxin herbicide, at least one monocarboxylic acid or its monocarboxylate in an amount sufficient to reduce the volatility of the auxin herbicide relative to an identical composition not containing the monocarboxylic acid or its monocarboxylate.

It has been found that adding a sufficient amount of a monocarboxylic acid or a monocarboxylate thereof (particularly a non-ammoniated monocarboxylate salt) to a herbicidal composition concentrate (e.g., a "premix") or a herbicidal composition application mixture (e.g., a "tank mix") results in a significant reduction in level of detected volatile auxin herbicide. For some compositions, the amount of volatile auxin herbicide present is actually below the level of detection by advanced analytical techniques such as liquid chromatography-mass spectrometry (LC-MS). Compared to auxin compositions known in the art, the compositions of the present invention are believed to provide increased protection against damage to target crops while maintaining comparable herbicidal effectiveness against auxin-sensitive plants located in the target area.

The present invention further provides methods for inhibiting the growth of auxin-sensitive plants, comprising applying the herbicidal compositions of the present invention to such plants according to the guidelines provided below.

As used throughout this application, the term "agriculturally acceptable salt" refers to a salt containing a cation that is known and acceptable in the art of preparing salts for agricultural or horticultural use. In one embodiment, the salt is a water-soluble salt.

A. Auxin herbicide component

The term "auxin herbicide" refers to a herbicide that functions as a plant growth hormone auxin mimic, thereby affecting plant growth regulation. Examples of auxin herbicides that are suitable for use in the herbicidal compositions of the present invention include, but are not limited to, benzoic acid type herbicides, phenoxy herbicides, pyridine carboxylic acid type herbicides, pyridine oxy herbicides, pyrimidine carboxylic acid herbicides, quinoline carboxylic acid type herbicides and benzothiazole type herbicides.

Specific examples of auxin herbicides include

Dicamba (3,6-dichloro-2-methoxybenzoic acid);

2,4-D (2,4-dichlorophenoxyacetic acid);

2,4-DB (4-(2,4-dichlorophenoxy(buntanoic acid);

Dichlorprop (2-(2,4-dichlorophenoxy)propanoic acid);

MCPA ((4-chloro-2-methylphenoxy)acetic acid);

MSPB (4-(4-chloro-2-methylphenoxy)butanoic acid);

Aminopyralide (4-amino-3,6-dichloro-2-pyridinecarboxylic acid);

Chloropyralide (3,6-dichloro-2-pyridinecarboxylic acid);

Fluoroxypyr ([(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acetic acid);

Triclopyr ([(3,5,b-trichloro-2-pyridinyl)oxy]acetic acid);

Diclopyr;

Mecoprop (2-(4-chloro-2-methylphenoxy)propanoic acid);

Mecoprop-R;

Picloram (4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid);

Hinklorac (3,7-dichloro-8-quinolinecarboxylic acid) and

Aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid);

including their salts and esters, racemic mixtures and separated (individual) isomers and combinations thereof.

In one embodiment, the herbicidal composition contains dicamba or an agriculturally acceptable salt or ester thereof. Examples of suitable dicamba salts include N,N-bis-[aminopropyl]methylamine, monoethanolamine, dimethylamine (e.g., BANVEL®, ORACLE®, etc.), isopropylamine, diglycolamine (e.g., CLARITY®, VANQUISH®, etc. ), their potassium and sodium salts and combinations. Commercially available sources of dicamba and its agriculturally acceptable salts include products sold under the trade names BANVEL®, CLARITY®, DIABLO®, DISTINCT, ORACLE®, VANQUISH® and VISION®.

In another embodiment, the herbicidal composition contains 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.

Throughout the remainder of the specification, in which reference is made to dicamba or its agriculturally acceptable salt or ester, it will be apparent to one skilled in the art that, in general, the principles of the present invention apply to auxin herbicides, including the herbicides described above, and that the present invention is not limited to herbicidal compositions containing dicamba or its agriculturally acceptable salt or ester.

In another embodiment, the herbicidal composition contains 2,4-D or an agriculturally acceptable salt or ester thereof. Examples of suitable 2,4-D salts include choline, dimethylamine and isopropylamine salts, and combinations thereof. Examples of suitable 2,4-D esters include 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 or esters include products sold under the trade names BARRAGE®, FORMULA 40®, OPT-AMINE® and WEEDAR 64®.

In another embodiment, the herbicidal composition contains 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.

In another embodiment, the herbicidal composition comprises an agriculturally acceptable 2,4-D ester, wherein the ester is selected from the group consisting of butyl (ie, 2,4-DB) and isooctyl esters and combinations thereof.

In another embodiment, the herbicidal composition contains 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.

In another embodiment, the herbicidal composition contains an agriculturally acceptable auxin herbicide salt (such as a dicamba salt, a 2,4-D salt, and/or a 2,4-DB salt), which is an ionic liquid described in published application US 2013/0109572 , i.e. a salt that is liquid at a temperature of approximately 150°C or lower. The full text of US 2013/0109572 is incorporated by reference into this application.

B. Monocarboxylic acid/monocarboxylate component

"Monocarboxylic acid" refers to a hydrocarbon or substituted hydrocarbon containing only one carboxyl functional group (ie R ¹ -C(O)OH). "Monocarboxylate" refers to a salt (i.e. R ¹ -C(O)OM, where M is an agriculturally acceptable cation) or ester (i.e. R ¹ -C(O)OR ² , where R ² is a hydrocarbon or substituted hydrocarbon radical) of a monocarboxylic acid. In one embodiment, the composition contains at least one monocarboxylate salt, which in aqueous compositions may be present wholly or partially in dissociated form as the monocarboxylate anion and the corresponding cation.

Said monocarboxylic acids and monocarboxylates typically contain a hydrocarbon or substituted hydrocarbon radical selected, for example, from unsubstituted or substituted straight or branched chain alkyl (for example, C ₁ -C ₂₀ alkyl, such as methyl, ethyl, n-propyl, isopropyl, etc. .d.); unsubstituted or substituted straight or branched chain alkenyl (eg C ₂ -C ₂₀ alkenyl such as ethenyl, n-propenyl, isopropenyl, etc.); unsubstituted or substituted aryl (eg phenyl, hydroxyphenyl, etc.) or unsubstituted or substituted arylalkyl (eg benzyl). In one embodiment, the monocarboxylic acid is selected from the group consisting of formic acid, acetic acid, propionic acid and benzoic acid. In another embodiment, the monocarboxylate salt is selected from the group consisting of formate salts, acetate salts, propionate salts and benzoate salts.

In one embodiment, the herbicidal composition contains a monocarboxylate salt having the formula R ¹ -C(O)OM, where R ¹ is an unsubstituted or substituted C ₁ -C ₁₀ alkyl and M is a non-ammoniated, agriculturally acceptable cation. In another embodiment, the herbicidal composition contains a monocarboxylate salt having the formula R ¹ -C(O)OM, where R ¹ represents an unsubstituted C ₁ -C ₆ alkyl and M represents an alkali metal cation. In another embodiment, the herbicidal composition contains a monocarboxylate salt having the formula R ¹ -C(O)OM, where R ¹ is an unsubstituted C ₁ -C ₃ alkyl and M is an alkali metal cation selected from sodium and potassium. In another embodiment, the monocarboxylate salt is potassium acetate. In another embodiment, the monocarboxylate salt is sodium acetate.

C. Alkali metal phosphate/alkali metal carbonate

The herbicidal compositions of the present invention may optionally further contain an alkali metal phosphate, such as potassium monohydrogen phosphate. Potassium monohydrogen phosphate, for example, may provide additional buffering and/or water-conditioning effect for the aqueous herbicidal compositions of the present invention. Potassium monohydrogen phosphate is particularly effective as a substitute for ammonium sulfate in herbicide application mixtures prepared using hard water.

Likewise, the herbicidal compositions of the present invention may optionally further contain an alkali metal carbonate, such as potassium carbonate, to provide additional buffering and/or water-conditioning effect to the aqueous herbicidal compositions of the present invention.

In some embodiments, the herbicidal compositions of the present invention contain an alkali metal phosphate. In other embodiments, the herbicidal compositions contain an alkali metal carbonate. In further other embodiments, the herbicidal compositions comprise an alkali metal phosphate and an alkali metal carbonate.

D. Non-herbicidal additives

The herbicidal compositions of the present invention may further contain conventional additives such as surfactants, herbicide drift reducing agents, safety agents, solubility enhancing agents, thickening agents, flow enhancing agents, floatation agents, antifreeze agents , UV protective agents, preservatives, antimicrobial agents and/or other additives that are necessary or desirable to improve processing performance, crop protection or handling of the composition.

In one embodiment, the herbicidal composition contains less than about 10 ppm ammonium sulfate. In another embodiment, the herbicidal composition does not contain ammonium sulfate.

In one embodiment, the herbicidal composition does not contain an acid other than a monocarboxylic acid.

E. Non-auxin herbicide components

The herbicidal compositions of the present invention may optionally further contain at least one non-auxin herbicide. The term "non-auxinic herbicide" refers to a herbicide having a primary mode of action other than an auxinic herbicide. Representative examples of non-auxin herbicides include acetyl-CoA carboxylase (ACCase) inhibitors, acetolactate synthase (ALS) inhibitors, synthase inhibitors

acetohydroxy acids (AHAS), photosystem II inhibitors, photosystem I inhibitors, protoporphyrinogen oxidase (PPO or Protox) inhibitors, carotenoid biosynthesis inhibitors, enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor, glutamine synthetase inhibitor, dihydropteroate synthetase inhibitor, mitosis inhibitors and nucleic acid inhibitors; their salts and esters; racemic mixtures and separated isomers, and combinations thereof.

Representative examples of ACCase inhibitors include clethodim, clodinafop, fenoxaprop-R, fluazifop-R, chisalofop-R and sethoxydim.

Representative examples of ALS or AHAS inhibitors include flumetsulam, imazamethabenz-m, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, metsulfuron, prosulfuron and sulfosulfuron.

Representative examples of photosystem I inhibitors include diquat and paraquat.

Representative examples of photosystem II inhibitors include atrazine, cyanazine, diuron and methibuzine.

Representative examples of PPO inhibitors include acifluorofen, butafenacil, carfentrazone-ethyl, flufenpyr-ethyl, flutiacet, flumiclorac, flumioxazin, fomezafen, lactofen, oxadiazone, oxyfluorophene and sulfentrazone.

Representative examples of carotenoid biosynthesis inhibitors include aclonifen, amitrol, diflufenican, mesotrione and sulcotrione.

A representative example of an EPSP inhibitor is N-phosphonomethylglycine (glyphosate).

A representative example of a glutamine synthetase inhibitor is glufosinate.

Representative example of an inhibitor

Dihydropteroate synthetase is azulam.

Representative examples of mitosis inhibitors include acetochlor, atachlor, dithiopyr, S-metolachlor and thiazopyr.

Representative examples of nucleic acid inhibitors include diphenzoquat, fosamine, metam and pelargonic acid.

In one embodiment, the herbicidal compositions of the present invention further comprise a non-auxinic herbicide selected from the group consisting of acetochlor, glyphosate, glufosinate, flumioxazin, fomesafen and agriculturally acceptable salts thereof.

In one embodiment, the herbicidal compositions of the present invention further contain glyphosate or agriculturally acceptable salts thereof. Suitable glyphosate salts include, for example, ammonium, diammonium, dimethylammonium, monoethanolamine, isopropylamine and potassium salts, and combinations thereof. In one embodiment, glyphosate salts are selected from the group consisting of monoethanolamine, isopropylamine and potassium salts and combinations thereof.

In one embodiment, the herbicidal compositions of the present invention further contain glufosinate or agriculturally acceptable salts thereof.

In one embodiment, the herbicidal compositions of the present invention contain dicamba or an agriculturally acceptable salt or ester thereof, and glyphosate or an agriculturally acceptable salt thereof. In another embodiment, 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 products sold under the trade names DURANGO® DMA®, HONCHO PLUS®, ROUNDUP POWERMAX®, ROUNDUP WEATHERMAX®, TRAXION® and TOUCHDOWN®.

In one embodiment, the herbicidal composition of the present invention contains 2,4-D or an agriculturally acceptable salt or ester thereof and glyphosate or an agriculturally acceptable salt thereof. In another embodiment, the herbicidal composition of the present invention contains 2,4-D or an agriculturally acceptable salt or ester thereof; glyphosate or an agriculturally acceptable salt thereof or a non-ammoniated agriculturally acceptable acetate salt.

In another embodiment, the herbicidal composition contains an agriculturally acceptable salt (such as a glyphosate salt), which is an ionic liquid described in published application US 2013/0109572, i.e. salt, which is liquid at a temperature of approximately 150°C or lower.

F. Loading Components

Suitable amounts, concentrations and/or molar ratios of auxic herbicide, monocarboxylic acid or monocarboxylate thereof and optional non-auxic herbicide and non-herbicidal additional components of the herbicidal compositions of the present invention will depend to some extent on whether the composition is a ready-to-use composition, a concentrate that is diluted with water before use (eg, a "premix"), or a herbicidal composition prepared by mixing two or more herbicidal components, water, and optionally other non-herbicidal components (eg, a "reservoir mixture").

1. Herbicide loading

The concentrated herbicidal compositions of the present invention typically contain, on an acid equivalent (AE) basis, a total herbicide load of, for example, from about 120 to about 600 g AE/L, from about 300 to about 600 g AE/L ./l, from about 350 to about 600 g ae/l, from about 400 to about 600 g ae/l, from about 450 to about 600 g ae/l, or from about 500 to approximately 600 g ae/l. Additional examples of total herbicide loading include about 120, 150, 200, 250, 300, 350, 400, 450, 500, 550 and 600 g ae/L and ranges thereof (e.g., from about 120 to about 150 g ae/L). e./l, from about 150 to about 200 g ae/l, from about 200 to about 250 g ae/l, from about 250 to about 300 g ae/l, from about 300 to about 350 g ae/L, from about 350 to about 400 g ae/L, from about 400 to about 450 g ae/L, from about 450 to about 500 g ae. /L, from about 500 to about 550 g ae/L, from about 550 to about 600 g ae/L total herbicide load).

In some embodiments, the herbicidal composition is a liquid concentrate containing, for example, a total amount (acid equivalent weight) of the herbicide from about 5% to about 75% by weight. % concentrate. In one aspect, the amount of herbicide is from about 10% to about 60% by weight. % concentrate. In another aspect, the amount of herbicide is from about 15% to about 50 wt. % concentrate. In another aspect, the amount of herbicide is from about 20% to about 40% by weight. % concentrate. In another aspect, the amount of herbicide is from about 25 to about 35 wt. % concentrate. In another aspect, the amount of herbicide is approximately 30 wt. % concentrate.

In some embodiments, the herbicidal composition is a dry concentrate (e.g., powder or granules) containing, for example, a total amount (acid equivalent weight) of the herbicide from about 40% to about 90% by weight. % concentrate. In one aspect, the amount of herbicide is from about 50% to about 80% by weight. % concentrate. In another aspect, the amount of herbicide is from about 60% to about 75% by weight. % concentrate. In another aspect, the amount of herbicide is from about 65% to about 70% by weight. % concentrate.

Ready-to-use herbicidal compositions and other herbicidal compositions of the present invention that do not require further processing prior to use (e.g., diluted concentrates, tank mixes, etc.) will generally contain, on an acid equivalent basis (e.g., ), total herbicide loading from about 0.1 g ae/L to about 50 g ae/L. Additional examples of total herbicide loadings for such compositions include 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45 and 50 g ae/L and ranges thereof (e.g., from about 0.5 to about 5 g ae/L, from about 5 to about 10 g ae/L, from about 10 to about 15 g ae. e./l, from about 15 to about 20 g ae/l, from about 20 to about 25 g ae/l, from about 25 to about 30 g ae/l, from about 30 to about 35 g ae/l, from about 35 to about 4 0 g ae/l, from about 4 0 to about 45 g ae/l, from about 45 to about 50 g ae. e./l of total herbicide load).

In the herbicidal compositions of the present invention containing an auxinic herbicide and a non-auxinic herbicide, the weight ratio of auxinic herbicide to non-auxinic herbicide on an acid equivalent basis is typically no more than 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, about 50:1 to about 1:1, about 50:1 to about 3:1, about 50:1 to about 5:1, about 50:1 to about 10 :1, from about 25:1 to about 1:1, or from about 25:1 to about 3:1.

For any given auxin herbicide, one skilled in the art can readily determine, using routine experimentation, the minimum concentration of auxin herbicide and the minimum ratio of auxin herbicide to any additional auxin herbicides and/or non-auxin herbicides contained in the herbicide composition that is desired for the intended application.

2. Monocarboxylic acid/monocarboxylate loading

As stated previously, the concentration of volatile auxin herbicide in the vapor phase surrounding a herbicidal composition containing an auxin herbicide and a monocarboxylic acid or monocarboxylate has been found to be less than the concentration of volatile auxin herbicide in the vapor phase surrounding a control composition containing no monocarboxylic acid or monocarboxylate , but otherwise having the same composition. In various embodiments, the concentration of the volatile auxin herbicide in the vapor phase surrounding the herbicidal composition comprising the auxin herbicide and a monocarboxylic acid or monocarboxylate thereof is less than about 90%, 80%, 70%, 60%, 50%, 40%, 30% , 20%, 10%, or 5% concentration of the volatile auxin herbicide in the vapor phase surrounding the control composition containing no monocarboxylate.

The herbicidal compositions of the present invention may contain one monocarboxylic acid or a monocarboxylate thereof, or a mixture of two or more monocarboxylic acids or monocarboxylates thereof.

The amount of monocarboxylic acid or monocarboxylate of the herbicidal composition will generally depend on the amount of auxinic herbicide included in the herbicide composition, the salt form of the auxinic herbicide and the properties of any other components of the herbicidal composition and will be an amount sufficient to reduce the volatility of the auxinic herbicide relative to a control composition not containing the monocarboxylic acid. or monocarboxylate, but otherwise having the same composition. For example, dicamba monoethanolamine and diethanolamine salts are less volatile than dicamba dimethylamine and isopropylamine salts, and the amount required for the less volatile salts may be less than the amount required for the more volatile salts. In addition, the amount of the monocarboxylic acid or its monocarboxylate may vary depending on the particular combination of the auxic herbicide, the optional non-auxic herbicide and the monocarboxylic acid or its monocarboxylate.

In the herbicidal compositions of the present invention, the molar ratio of auxin herbicide to monocarboxylic acid or monocarboxylate thereof is typically no less than about 1:10 and no more than about 10:1. Representative molar ratios of auxin herbicide acid equivalent (AE) to total monocarboxylic acid or monocarboxylate thereof are, for example, 1:10 to about 10:1, about 1:5 to about 5:1, and approximately 3:1 to approximately 1:3. In one aspect, the molar ratio of auxin herbicide to monocarboxylic acid or monocarboxylate thereof is from about 2:1 to about 1:2. In another aspect, the molar ratio of auxin herbicide to monocarboxylic acid or monocarboxylate thereof is approximately 1:1.

In some embodiments, the concentrates of the herbicidal compositions of the present invention contain a monocarboxylic acid or monocarboxylate thereof in an amount (acid equivalent weight) of from about 0.25% to about 25% by weight. % concentrate. In one aspect, the amount is from about 1% to about 20 wt. % concentrate. In another aspect, the amount is from about 2% to about 15 wt. % concentrate. In another aspect, the concentrate is a liquid concentrate and the amount

(acid equivalent weight) ranges from about 2% to about 10 wt. % concentrate. In another aspect, the concentrate is a dry concentrate and an amount

(acid equivalent weight) ranges from about 5% to about 15 wt. % concentrate. In another aspect, the monocarboxylic acid or monocarboxylate thereof is acetic acid or an agriculturally acceptable salt thereof.

In some embodiments, the reservoir mixtures of the herbicidal composition of the present invention contain a monocarboxylic acid or carboxylate thereof in an amount (acid equivalent weight) of from about 0.01% to about 25% by weight. % tank mixture. In one aspect, the amount is from about 0.01% to about 20 wt. % tank mixture. In another aspect, the amount is from about 0.05% to about 15 wt. % tank mixture. In another aspect, the amount is from about 0.05% to about 10 wt. % tank mixture. In another aspect, the amount is from about 0.05% to about 5 wt. % tank mixture. In another aspect, the amount is from about 0.1% to about 2 wt. % tank mixture. In another aspect, the amount is from about 0.1% to about 1 wt. % tank mixture. In another aspect, the monocarboxylic acid or monocarboxylate thereof is acetic acid or an agriculturally acceptable salt thereof.

3. Loading alkali metal phosphate/alkali metal carbonate

When the herbicidal composition contains an alkali metal phosphate, such as potassium monohydrogen phosphate, the molar ratio of alkali metal phosphate to monocarboxylic acid or monocarboxylate thereof may 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 approximately 1:1.

When the herbicidal composition contains an alkali metal carbonate, such as potassium carbonate, the molar ratio of alkali metal carbonate to monocarboxylic acid or monocarboxylate thereof may 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 approximately 1:1.

G. Embodiments of the Herbicidal Composition

Herbicidal compositions can be presented in various forms, depending on the intended use and required handling. For example, the herbicidal compositions of the present invention can be prepared in dry form (eg, powders, granules, etc.) or liquid form (eg, aqueous solutions, dispersions, etc.). The term "aqueous" as used herein, however, does not imply the exclusion of the presence of non-aqueous (ie, organic) solvents, provided that water is present. Water is the predominant component of the ready-to-use compositions and reservoir mixture compositions described herein.

Among the representations of the various compositions of the invention are the following compositions:

(a) a ready-to-use aqueous herbicidal composition that can be applied to unwanted plants without the need for additional dilution with water or other preparation;

(b) a concentrate of the herbicidal composition, which is diluted with water and optionally mixed with other herbicidal and non-herbicidal substances before use (including, for example, dry mixtures and premixes);

(c) a herbicidal composition application mixture prepared by diluting a concentrate of the herbicidal composition with water to obtain a herbicidal composition application mixture that can then be applied to auxin-susceptible plants;

(d) a herbicidal composition application mixture prepared by mixing two or more separate components with water (eg, a reservoir mixture) to form a herbicidal composition application mixture that can then be applied to auxin-sensitive plants; And

(e) a herbicidal composition application mixture prepared by introducing separate feed streams into a spray or application system such that the feed streams are mixed to form a herbicidal composition application mixture immediately prior to use.

In various embodiments, the herbicidal compositions (ready-to-use composition, liquid concentrate, reservoir mixture, etc.) have a pH value that is equal to or greater than the acid dissociation constant (pKa) of the monocarboxylic acid present in the composition. In some embodiments, for example, the herbicidal compositions contain acetic acid (which has a pKa of about 4.8) and have a pH value that is equal to or greater than about 4.8. In the case of herbicidal compositions containing dicamba and an effective amount of acetic acid, the volatility of dicamba generally decreases as the pH of the composition is increased, with dicamba volatility reaching substantially undetectable levels at a pH of approximately 5.2 as measured in plant response studies.

1. Illustrative embodiments of compositions (auxin herbicide concentrates)

One embodiment of the invention relates to a herbicidal composition concentrate containing

at least one auxin herbicide and

at least one monocarboxylic acid or monocarboxylate thereof;

where the concentrate 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 weight ratio of the monocarboxylic acid or monocarboxylate thereof, on an acid equivalent basis, to the auxinic herbicide is from about 1:10 to about 5:1;

the concentrate contains a monocarboxylic acid or its monocarboxylate in an amount (acid equivalent weight) of from about 0.25% to about 25% by weight. % concentrate;

the concentration of the monocarboxylic acid or its monocarboxylate is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L and

the concentrate contains a monocarboxylic acid or a monocarboxylate thereof in an amount sufficient to reduce the concentration of a volatile auxin herbicide in the vapor phase surrounding the concentrate by at least about 10% relative to the concentration of a volatile auxin herbicide in the vapor phase surrounding an identical concentrate not containing the monocarboxylic acid or its monocarboxylate.

In further embodiments, 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.

In further embodiments, the herbicidal composition concentrate contains dicamba or an agriculturally acceptable salt or ester thereof. In another embodiment, the concentrate contains a decamba salt selected from the group consisting of N,N-bis[aminopropyl]methylamine, monoethanolamine, dimethylamine, isopropylamine, glycolamine, potassium and sodium salts, and combinations thereof.

In other embodiments, the herbicidal composition concentrate contains 2,4-D or an agriculturally acceptable salt or ester thereof. In other embodiments, the concentrate contains a 2,4-D salt selected from the group consisting of choline, dimethylamine and isopropylamine salts and combinations thereof. In another embodiment, the concentrate contains a 2,4-D ester selected from the group consisting of butyl (ie, 2,4-DB) and isooctyl esters and combinations thereof.

In further embodiments, the herbicidal composition concentrate contains a monocarboxylate salt.

In further embodiments, the herbicidal composition concentrate contains a C ₁ -C ₆ alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate contains a C ₁ -C ₅ alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate contains a C ₁ -C ₄ alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate contains a C ₁ -C ₃ alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate contains acetic acid or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate contains formic acid or an agriculturally acceptable salt thereof.

In further embodiments, the monocarboxylate salt or acetate salt is a non-ammoniated salt. In another embodiment, the monocarboxylate salt or acetate salt is an alkali metal salt. In another embodiment, the monocarboxylate salt or acetate salt is a potassium salt. In another embodiment, the monocarboxylate salt or acetate salt is a sodium salt.

In further embodiments, the herbicidal composition concentrate contains a buffer.

In further embodiments, the herbicidal composition concentrate further comprises an alkali metal phosphate, such as potassium monohydrogen phosphate.

In further embodiments, the herbicidal composition concentrate is a dry powder herbicidal composition.

In further embodiments, the herbicidal composition concentrate is an aqueous herbicidal composition.

In further embodiments, the herbicidal composition concentrate further comprises a non-auxin herbicide. In another embodiment, the non-auxinic herbicide is selected from the group consisting of acetochlor, glyphosate, glufosinate, fumioxazine, fomesafen, and agriculturally acceptable salts thereof. In another embodiment, the non-auxin herbicide is glyphosate or an agriculturally acceptable salt thereof. In another embodiment, the concentrate contains a glyphosate salt selected from the group consisting of ammonium, diammonium, dimethylammonium, monoethanolamine, isopropylamine and potassium salts, and combinations thereof. In another embodiment, the non-auxin herbicide-containing concentrate satisfies one or more of the following conditions:

the weight ratio of auxinic herbicide to non-auxinic herbicide on an acid equivalent basis is from about 1:5 to about 2:1 and

the weight ratio of the monocarboxylic acid or monocarboxylate thereof, based on acid equivalent, to the auxinic herbicide is from about 1:10 to about 5:1.

In further embodiments, the herbicidal composition concentrate has a pH value equal to or greater than the pKa value _{of the} monocarboxylic acid selected for the composition.

2. Illustrative embodiments of the compositions (mixtures for the application of auxin herbicides)

One embodiment of the invention relates to a herbicidal composition containing

at least one auxin herbicide and

at least one monocarboxylic acid or monocarboxylate thereof;

where the 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 weight ratio of the monocarboxylic acid or monocarboxylate thereof, on an acid equivalent basis, to the auxinic herbicide is from about 1:10 to about 5:1;

the composition contains a monocarboxylic acid or its monocarboxylate in an amount (acid equivalent weight) of from about 0.01% to about 25 wt. % composition;

the concentration of the monocarboxylic acid or its monocarboxylate is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L and

the composition contains a monocarboxylic acid or a monocarboxylate thereof in an amount sufficient to reduce the concentration of a volatile auxin herbicide in the vapor phase surrounding the composition by at least about 10% relative to the concentration of a volatile auxin herbicide in the vapor phase surrounding an identical composition not containing the monocarboxylic acid or its monocarboxylate.

In one aspect, the composition contains a monocarboxylic acid or carboxylate thereof in an amount (acid equivalent weight) of from about 0.1% to about 25% by weight. % composition.

In further embodiments, the composition contains 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.

In further embodiments, the composition contains dicamba or an agriculturally acceptable salt or ester thereof. In another embodiment, the composition contains 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.

In further embodiments, the composition contains 2,4-D or an agriculturally acceptable salt or ester thereof. In another embodiment, the composition contains a 2,4-D salt selected from the group consisting of choline, dimethylamine and isopropylamine salts, and combinations thereof. In another embodiment, the composition contains a 2,4-D ester, such as 2,4-DB.

In further embodiments, the composition contains a monocarboxylate salt.

In further embodiments, the herbicidal composition concentrate contains a C ₁ -C ₆ alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate contains a C ₁ -C ₅ alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate contains a C ₁ -C ₄ alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate contains a C ₁ -C ₃ alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate contains acetic acid or an agriculturally acceptable salt thereof. In other embodiments, the herbicidal composition concentrate contains formic acid or an agriculturally acceptable salt thereof.

In further embodiments, the monocarboxylate salt or acetate salt is a non-ammoniated salt. In another embodiment, the monocarboxylate salt or acetate salt is an alkali metal salt. In another embodiment, the monocarboxylate salt or acetate salt is a potassium salt. In another embodiment, the monocarboxylate salt or acetate salt is a sodium salt.

In further embodiments, the composition further comprises a buffer.

In further embodiments, the herbicidal composition concentrate further comprises an alkali metal phosphate, such as potassium monohydrogen phosphate.

In further embodiments, the composition is an aqueous herbicidal composition.

In further embodiments, the composition further comprises a non-auxin herbicide. In another embodiment, the non-auxinic herbicide is selected from the group consisting of acetochlor, glyphosate, glucofosinate, flumioxazin, fomesafen, and agriculturally acceptable salts thereof. In another embodiment, the non-auxin herbicide is glyphosate or an agriculturally acceptable salt thereof. In another embodiment, the concentrate contains a glyphosate salt selected from the group consisting of ammonium, diammonium, dimethylammonium, monoethanolamine, isopropylamine and potassium salts, and combinations thereof. In another embodiment, the non-auxin herbicide-containing concentrate satisfies one or more of the following conditions:

the sum of the auxinic herbicide concentration and the non-auxinic herbicide concentration is from about 1 gram (acid equivalent weight)/L to about 50 grams (acid equivalent weight)/L;

the weight ratio of auxinic herbicide to non-auxinic herbicide on an acid equivalent basis is from about 1:5 to about 2:1 and

the weight ratio of the monocarboxylic acid or monocarboxylate thereof, based on acid equivalent, to the auxinic herbicide is from about 1:10 to about 5:1.

3. Illustrative Embodiments of a Composition (Dicamba Concentrate)

Compositions of particular interest include herbicidal compositions containing 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.

One embodiment of the invention relates to a herbicidal composition concentrate containing

dicamba or its agriculturally acceptable salt or ester and

acetic acid or an agriculturally acceptable salt thereof;

wherein the molar ratio of acetic acid or its agriculturally acceptable salt to dicamba or its agriculturally acceptable salt or ester is from about 1:10 to about 10:1.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester, and

(b) acetic acid or an agriculturally acceptable salt thereof;

wherein the weight ratio of acetic acid or its agriculturally acceptable salt, on an acid equivalent basis, to dicamba or its agriculturally acceptable salt or ester is from about 1:10 to about 5:1.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester, and

(b) acetic acid or an agriculturally acceptable salt thereof;

wherein the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 0.25% to about 25% by weight. % concentrate.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester, and

(b) acetic acid or an agriculturally acceptable salt thereof;

wherein the concentration of acetic acid or an agriculturally acceptable salt thereof is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester, and

(b) acetic acid or an agriculturally acceptable salt thereof;

wherein the concentration of dicamba or its agriculturally acceptable salt or ester is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester, and

(b) acetic acid or an agriculturally acceptable salt thereof;

wherein the concentration of dicamba or its agriculturally acceptable salt or ester is from about 120 grams (acid equivalent weight)/L to about 6000 grams (acid equivalent weight)/L and

wherein the weight ratio of acetic acid or its agriculturally acceptable salt, on an acid equivalent basis, to dicamba or its agriculturally acceptable salt or ester is from about 1:10 to about 5:1.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester, and

(b) acetic acid or an agriculturally acceptable salt thereof;

wherein the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount sufficient to reduce the concentration of volatile dicamba or an agriculturally acceptable salt or ester thereof in the vapor phase surrounding the concentrate by at least about 10%, 20%, 30% , 40%, 50%, 60%, 70%, 80%, 90% or 95% relative to the concentration of volatile dicamba or its agriculturally acceptable salt or ester in the vapor phase surrounding an identical concentrate containing no or agriculturally acceptable acetic acid agriculture salt.

In further embodiments, the herbicidal composition concentrate contains 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.

In further embodiments, the herbicidal composition concentrate contains an acetate salt. In another embodiment, the acetate salt is an alkali metal salt. In another embodiment, the acetate salt is a potassium salt. In another embodiment, the acetate salt is a sodium salt.

In further embodiments, the herbicidal composition concentrate further comprises a buffer.

In further embodiments, the herbicidal composition concentrate further comprises an alkali metal phosphate, such as potassium monohydrogen phosphate.

In other embodiments, the herbicidal composition concentrate is a dry powder herbicidal composition.

In other embodiments, the herbicidal composition concentrate is an aqueous herbicidal composition.

In further embodiments, the herbicidal composition concentrate further comprises a non-auxinic herbicide. In another embodiment, the non-auxinic herbicide is selected from the group consisting of acetochlor, glyphosate, glufosinate, flumioxazine, fomezafen, and agriculturally acceptable salts thereof. In another embodiment, the non-auxin herbicide-containing concentrate satisfies one or more of the following conditions:

the sum of the auxinic herbicide concentration and the non-auxinic herbicide concentration is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L;

the weight ratio of auxinic herbicide to non-auxinic herbicide on an acid equivalent basis is from about 1:5 to about 2:1 and

the weight ratio of the monocarboxylic acid or monocarboxylate thereof, based on acid equivalent, to the auxinic herbicide is from about 1:10 to about 5:1.

In further embodiments, the herbicidal composition concentrate has a pH value equal to or greater than the pKa value _of acetic acid (ie, 4.8).

4. Illustrative Embodiments of Compositions (Dicamba/Glyphosate Concentrate)

One embodiment of the invention relates to a herbicidal composition concentrate containing

(a) dicamba or its agriculturally acceptable salt or ester;

(b) glyphosate or an agriculturally acceptable salt thereof, and

(c) acetic acid or an agriculturally acceptable salt thereof;

wherein the molar ratio of acetic acid or its agriculturally acceptable salt to dicamba or its agriculturally acceptable salt or ester is from about 1:10 to about 10:1.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester;

(b) glyphosate or an agriculturally acceptable salt thereof, and

(c) acetic acid or an agriculturally acceptable salt thereof;

wherein the weight ratio of acetic acid or its agriculturally acceptable salt, on an acid equivalent basis, to dicamba or its agriculturally acceptable salt or ester is from about 1:10 to about 5:1.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester;

(b) glyphosate or an agriculturally acceptable salt thereof, and

(c) acetic acid or an agriculturally acceptable salt thereof;

wherein the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 0.25% to about 25% by weight. % concentrate.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester;

(b) glyphosate or an agriculturally acceptable salt thereof, and

(c) acetic acid or an agriculturally acceptable salt thereof;

wherein the concentration of acetic acid or an agriculturally acceptable salt thereof is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester;

(b) glyphosate or an agriculturally acceptable salt thereof, and

(c) acetic acid or an agriculturally acceptable salt thereof;

wherein the sum of the concentration of dicamba or its agriculturally acceptable salt or ester and the concentration of glyphosate or its agriculturally acceptable salt is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L. In another embodiment, 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 .

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester;

(b) glyphosate or an agriculturally acceptable salt thereof, and

(c) acetic acid or an agriculturally acceptable salt thereof;

wherein the sum of the concentration of dicamba or its agriculturally acceptable salt or ester and the concentration of glyphosate or its agriculturally acceptable salt is from about 120 grams (acid equivalent weight)/L to about 600 grams (acid equivalent weight)/L

and wherein the weight ratio of dicamba or an agriculturally acceptable salt or ester thereof, on an acid equivalent basis, to glyphosate or an agriculturally acceptable salt thereof is from about 1:5 to about 2:1.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester;

(b) glyphosate or an agriculturally acceptable salt thereof, and

(c) acetic acid or an agriculturally acceptable salt thereof;

wherein 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;

wherein the weight ratio of dicamba or an agriculturally acceptable salt or ester thereof, on an acid equivalent basis, to glyphosate or an agriculturally acceptable salt thereof is from about 1:5 to about 2:1 and

wherein the weight ratio of acetic acid or its agriculturally acceptable salt, on an acid equivalent basis, to dicamba or its agriculturally acceptable salt or ester is from about 1:10 to about 5:1.

In another embodiment, the herbicidal composition concentrate contains

(a) dicamba or its agriculturally acceptable salt or ester,

(b) glyphosate or an agriculturally acceptable salt thereof, and

(c) acetic acid or an agriculturally acceptable salt thereof;

wherein the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount sufficient to reduce the concentration of volatile dicamba or an agriculturally acceptable salt or ester thereof in the vapor phase surrounding the concentrate by at least about 10%, 20%, 30% , 40%, 50%, 60%, 70%, 80%, 90% or 95% relative to the concentration of volatile dicamba or its agriculturally acceptable salt or ester in the vapor phase surrounding an identical concentrate containing no or agriculturally acceptable acetic acid agriculture salt.

In further embodiments, the herbicidal composition concentrate contains 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.

In further embodiments, the herbicidal composition concentrate contains an acetate salt. In another embodiment, the acetate salt is an alkali metal salt. In another embodiment, the acetate salt is a potassium salt. In another embodiment, the acetate salt is a sodium salt.

In further embodiments, the herbicidal composition concentrate further comprises a buffer.

In further embodiments, the herbicidal composition concentrate further comprises an alkali metal phosphate, such as potassium monohydrogen phosphate.

In further embodiments, the herbicidal composition concentrate is a dry powder herbicidal composition.

In further embodiments, the herbicidal composition concentrate is an aqueous herbicidal composition.

In another embodiment, the concentrate contains a glyphosate salt selected from the group consisting of ammonium, diammonium, dimethylammonium, monoethanolamine, isopropylamine and potassium salts, and combinations thereof.

In another embodiment, the concentrate satisfies one or more of the following conditions:

the sum of the concentration of dicamba or an agriculturally acceptable salt 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 weight ratio of dicamba or an agriculturally acceptable salt thereof, based on acid equivalent, to glyphosate or an agriculturally acceptable salt thereof is from about 1:5 to about 2:1 and

the weight ratio of the monocarboxylic acid or monocarboxylate thereof, on an acid equivalent basis, to dicamba or an agriculturally acceptable salt thereof is from about 1:10 to about 5:1.

In further embodiments, the herbicidal composition concentrate has a pH value equal to or greater than the pKa value _of acetic acid (ie, 4.8).

5. Illustrative embodiments of the compositions (mixture for dicamba administration)

In further embodiments, the herbicidal compositions correspond to the compositions described above under “illustrative embodiment of the composition (auxin herbicide application mixture)”, wherein the auxin herbicide is dicamba or an agriculturally acceptable salt or ester thereof.

6. Illustrative embodiments of the compositions (dicamba/glyphosate application mixture)

In further embodiments, the herbicidal compositions correspond to the compositions described above in the "illustrative embodiment of the composition (auxin herbicide application mixture)" section, wherein the auxin herbicide is dicamba or an agriculturally acceptable salt or ester thereof, and the compositions further comprise glyphosate or agriculturally acceptable salt or ether.

7. Exemplary Composition Embodiments (Dicamba/Glufosinate Administration Blend)

In further embodiments, the herbicidal compositions correspond to the compositions described above in the "illustrative embodiment of the composition (auxin herbicide application mixture)" section, wherein the auxin herbicide is dicamba or an agriculturally acceptable salt or ester thereof, and the compositions further comprise glufosinate or agriculturally acceptable salt or ether.

8. Illustrative embodiments of compositions (2,4-D)

Compositions of particular interest also include herbicidal compositions containing 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.

In further embodiments, the herbicidal compositions correspond to the compositions described above in the sections “Illustrative Embodiment of a Composition (Dicamba Concentrate)”, “Illustrative Embodiment of a Composition (Dicamba/Glyphosate Concentrate)”, “Illustrative Embodiment of a Composition (Dicamba Application Blend)”, “an illustrative embodiment of a composition (dicamba/glyphosate administration mixture)” and “an illustrative embodiment of a composition (dicamba/glufosinate application mixture)”, except that dicamba or its agriculturally acceptable salt or ester replaces the 2,4- D or an agriculturally acceptable salt or ether thereof.

9. Illustrative embodiments of the compositions (liquid dicamba concentrate)

One embodiment of the invention relates to a herbicidal composition which is a liquid concentrate containing

dicamba or its agriculturally acceptable salt or ester and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 1% to about 25% by weight. % concentrate and

the concentrate contains dicamba or its agriculturally acceptable salt or ester in an amount (acid equivalent weight) of from about 10% to about 60% by weight. % concentrate.

In one aspect, the liquid concentrate has a dicamba loading of from about 300 g ae/L to about 400 g ae/L.

In another embodiment, the liquid concentrate contains

dicamba or its agriculturally acceptable salt or ester and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 2% to about 20% by weight. % concentrate and

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 15% to about 50% by weight. % concentrate.

In another embodiment, the liquid concentrate contains

dicamba or an acceptable salt or ester thereof and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 3% to about 15% by weight. % concentrate and

the concentrate contains dicamba or its agriculturally acceptable salt or ester in an amount (acid equivalent weight) of from about 20% to about 40% by weight. % concentrate.

In another embodiment, the liquid concentrate contains

dicamba or its agriculturally acceptable salt or ester and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 3% to about 10% by weight. % concentrate and

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 25% to about 35% by weight. % concentrate.

In further embodiments, the liquid concentrate contains 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. In one aspect, the liquid concentrate contains a dicamba salt formed with diglycolamine.

In further embodiments, the liquid concentrate contains an acetate salt. In another embodiment, the acetate salt is an alkali metal salt. In another embodiment, the acetate salt is a potassium salt. In another embodiment, the acetate salt is a sodium salt.

In further embodiments, the liquid concentrate contains an acetate salt that is formed in situ during production of the liquid concentrate when acetic acid is contacted with a neutralizing base, such as an alkali metal hydroxide. For example, a liquid concentrate can be prepared by mixing dicamba, or an agriculturally acceptable salt or ester thereof, with water, followed by the addition of acetic acid and then the addition of a neutralizing base. Although a specific order of addition of the ingredients is not required to obtain the final composition, the order of addition described above may be beneficial in reducing the heat generated when the ingredients are mixed. In one aspect, the neutralizing base is potassium hydroxide. In another aspect, the neutralizing base is sodium hydroxide.

10. Illustrative embodiments of the composition (dry dicamba concentrate)

One embodiment of the invention relates to a herbicidal composition which is a dry concentrate containing

dicamba or its agriculturally acceptable salt or ester and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 1% to about 40% by weight. % concentrate;

the concentrate contains dicamba or its agriculturally acceptable salt or ester in an amount (acid equivalent weight) of from about 40% to about 90% by weight. % concentrate and

where the sum of the weight percent of acetic acid and the weight percent of dicamba is less than 100% or equal to 100%.

In another embodiment, the dry concentrate contains

dicamba or its agriculturally acceptable salt or ester and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 3% to about 30% by weight. % concentrate;

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 50% to about 80% by weight. % concentrate and

where the sum of the weight percent of acetic acid and the weight percent of dicamba is less than 100% or equal to 100%.

In another embodiment, the dry concentrate contains

dicamba or its agriculturally acceptable salt or ester and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 5% to about 20% by weight. % concentrate and

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 60% to about 75% by weight. % concentrate.

In further embodiments, the dry concentrate contains 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. In one aspect, the liquid concentrate contains a dicamba salt formed with diglycolamine.

In further embodiments, the dry concentrate contains an acetate salt. In another embodiment, the acetate salt is an alkali metal salt. In another embodiment, the acetate salt is a potassium salt. In another embodiment, the acetate salt is a sodium salt.

In further embodiments, the dry concentrate is in the form of a dry powder.

In further embodiments, the dry concentrate is in the form of dry granules.

11. Exemplary Composition Embodiments (Dicamba/Glyphosate Liquid Premix)

One embodiment of the invention relates to a herbicidal composition which is a liquid concentrate containing

dicamba or its agriculturally acceptable salt or ester and

glyphosate or its agriculturally acceptable salt and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 1% to about 25% by weight. % concentrate;

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 2% to about 25% by weight. % concentrate and

the concentrate contains glyphosate or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 4% to about 50% by weight. % concentrate.

In one aspect, the liquid concentrate has a total herbicide load of from about 350 g ae/L to about 500 g ae/L. / l.

In another embodiment, the liquid concentrate contains

dicamba or its agriculturally acceptable salt or ester and

glyphosate or an agriculturally acceptable salt thereof, and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 2% to about 20% by weight. % concentrate;

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 3% to about 20% by weight. % concentrate and

the concentrate contains glyphosate or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 6% to about 40% by weight. % concentrate.

In another embodiment, the liquid concentrate contains

dicamba or its agriculturally acceptable salt or ester and

glyphosate or an agriculturally acceptable salt thereof, and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 3% to about 15% by weight. % concentrate;

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 4% to about 15% by weight. % concentrate and

the concentrate contains glyphosate or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 8% to about 30% by weight. % concentrate.

In another embodiment, the liquid concentrate contains

dicamba or its agriculturally acceptable salt or ester and

glyphosate or an agriculturally acceptable salt thereof, and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 3% to about 10% by weight. % concentrate;

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 5% to about 15% by weight. % concentrate and

the concentrate contains glyphosate or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 10% to about 30% by weight. % concentrate.

In further embodiments, the liquid concentrate contains 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. In one aspect, the liquid concentrate contains a dicamba salt formed by diglycolamine.

In further embodiments, the liquid concentrate contains an acetate salt. In another embodiment, the acetate salt is an alkali metal salt. In another embodiment, the acetate salt is a potassium salt. In another embodiment, the acetate salt is a sodium salt.

In further embodiments, the liquid concentrate contains an acetate salt that is formed in situ during production of the liquid concentrate when acetic acid is contacted with a neutralizing base, such as an alkali metal hydroxide. For example, a liquid concentrate can be prepared by mixing dicamba or its agriculturally acceptable salt or ester with water, followed by the addition of acetic acid and then the addition of a neutralizing base. Although a specific order of addition of the ingredients is not required to obtain the final composition, the order of addition described above may be beneficial in reducing the heat generated when the ingredients are mixed. In one aspect, the neutralizing base is potassium hydroxide. In another aspect, the neutralizing base is sodium hydroxide.

12. Illustrative embodiments of the compositions (dicamba/glyphosate premix)

One embodiment of the invention relates to a herbicidal composition which is a dry concentrate containing

dicamba or its agriculturally acceptable salt or ester and

glyphosate or an agriculturally acceptable salt thereof, and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 1% to about 40% by weight. % concentrate;

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 5% to about 40% by weight. % concentrate;

the concentrate contains glyphosate or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 40% to about 80% by weight. % concentrate and

where the sum of the weight percent of acetic acid, the weight percent of dicamba and the weight percent of glyphosate is less than 100% or equal to 100%.

In another embodiment, the dry concentrate contains

dicamba or its agriculturally acceptable salt or ester and

glyphosate or an agriculturally acceptable salt thereof, and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 3% to about 30% by weight. % concentrate;

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 10% to about 35% by weight. % concentrate and

the concentrate contains glyphosate or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 40% to about 70% by weight. % concentrate and

where the sum of the weight percent of acetic acid, the weight percent of dicamba and the weight percent of glyphosate is less than 100% or equal to 100%.

In another embodiment, the dry concentrate contains

dicamba or its agriculturally acceptable salt or ester and

glyphosate or an agriculturally acceptable salt thereof, and

acetic acid or an agriculturally acceptable salt thereof;

Where

the concentrate contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 5% to about 15% by weight. % concentrate;

the concentrate contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) of from about 20% to about 30% by weight. % concentrate and

the concentrate contains glyphosate or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 45% to about 55% by weight. % concentrate.

In further embodiments, the dry concentrate contains 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. In one aspect, the liquid concentrate contains a dicamba salt formed with diglycolamine.

In further embodiments, the dry concentrate contains an acetate salt. In another embodiment, the acetate salt is an alkali metal salt. In another embodiment, the acetate salt is a potassium salt. In another embodiment, the acetate salt is a sodium salt.

In further embodiments, the dry concentrate is in the form of a dry powder.

In further embodiments, the dry concentrate is in the form of dry granules.

13. Illustrative embodiments of compositions (combination packaging)

One embodiment of the invention relates to a combination package containing a first container containing dicamba or an agriculturally acceptable salt or ester thereof, and a second container containing acetic acid or an agriculturally acceptable salt thereof. In one aspect, the first container contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) that is at least about 20 weight percent. % of the first container. In one aspect, the first container contains a liquid composition containing dicamba or an agriculturally acceptable salt or ester thereof. In one aspect, the first container contains a dry composition containing dicamba or an agriculturally acceptable salt or ester thereof.

In another embodiment, the invention relates to a combination package containing a first container containing dicamba or an agriculturally acceptable salt or ester thereof; a second container containing glyphosate or an agriculturally acceptable salt thereof; and a third container containing acetic acid or an agriculturally acceptable salt thereof. In one aspect, the first container contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) that is at least about 20 weight percent. % of the first container. In one aspect, the first container contains a liquid composition containing dicamba or an agriculturally acceptable salt or ester thereof. In one aspect, the first container contains a dry composition containing dicamba or an agriculturally acceptable salt or ester thereof. In one aspect, the second container contains glyphosate or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) that is at least about 20 weight percent. % of the second container. In one aspect, the second container contains a liquid composition containing glyphosate or an agriculturally acceptable salt thereof. In one aspect, the second container contains a dry composition containing glyphosate or an agriculturally acceptable salt thereof.

In another embodiment, the invention relates to a combination package containing a first container containing dicamba or an agriculturally acceptable salt or ester thereof; a second container containing glufosinate or an agriculturally acceptable salt or ester thereof; and a third container containing acetic acid or an agriculturally acceptable salt thereof. In one aspect, the first container contains dicamba or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) that is at least about 20 weight percent. % of the first container. In one aspect, the first container contains a liquid composition containing dicamba or an agriculturally acceptable salt or ester thereof. In one aspect, the first container contains a dry composition containing dicamba or an agriculturally acceptable salt or ester thereof. In one aspect, the second container contains glufosinate or an agriculturally acceptable salt or ester thereof in an amount (acid equivalent weight) that is at least about 10 weight percent. % of the second container. In one aspect, the second container contains a liquid composition containing glufosinate or an agriculturally acceptable salt or ester thereof. In one aspect, the second container contains a dry composition containing glufosinate or an agriculturally acceptable salt or ester thereof.

In another embodiment, the invention relates to a combination package containing a first container containing glyphosate or an agriculturally acceptable salt thereof, and a second container containing acetic acid or an agriculturally acceptable salt thereof. In one aspect, the first container contains glyphosate or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) that is at least about 20 weight percent. % of the first container. In one aspect, the first container contains a liquid composition containing glyphosate or an agriculturally acceptable salt thereof. In one aspect, the first container contains a dry composition containing glyphosate or an agriculturally acceptable salt thereof.

In another embodiment, the invention relates to a combination package containing a first container containing glufosinate or an agriculturally acceptable salt or ester thereof, and a second container containing acetic acid or an agriculturally acceptable salt thereof. In one aspect, the first container contains glufosinate or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) that is at least about 10 wt. % of the first container. In one aspect, the first container contains a liquid composition containing glufosinate or an agriculturally acceptable salt thereof. In one aspect, the first container contains a dry composition containing glufosinate or an agriculturally acceptable salt thereof.

N. Adjuvant of herbicidal composition

As discussed in more detail below, in some embodiments, methods for inhibiting the growth of auxin-sensitive plants include providing an application mixture by mixing a source of auxin herbicide (eg, CLARITY®); a source of monocarboxylic acid or its monocarboxylate; an optional source of non-auxin herbicide (eg, DURANGO® or POWERMAX®); and water. Another embodiment of the present invention, therefore, relates to a herbicidal adjuvant composition containing a monocarboxylic acid or a monocarboxylate thereof and optionally an alkali metal phosphate, which can serve as a source of the monocarboxylic acid or its monocarboxylate used in preparing the application mixture.

In one embodiment, the adjuvant composition used in preparing the mixture for applying the herbicidal composition contains:

(a) at least one monocarboxylic acid or a monocarboxylate thereof, and

(b) alkali metal phosphate;

wherein the molar ratio of the monocarboxylic acid or its monocarboxylate to the alkali metal phosphate is from about 1:5 to about 5:1.

In various embodiments, the adjuvant composition contains a C ₁ -C ₆ -alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the adjuvant composition contains a C ₁ -C ₅ -alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the adjuvant composition contains a C ₁ -C ₄ -alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the adjuvant composition contains a C ₁ -C ₃ alkanoic acid or an agriculturally acceptable salt thereof. In other embodiments, the adjuvant composition contains a monocarboxylic acid selected from the group consisting of formic acid, acetic acid, propionic acid and benzoic acid. In other embodiments, the adjuvant composition contains acetic acid or an agriculturally acceptable salt thereof. In other embodiments, the adjuvant composition contains formic acid or an agriculturally acceptable salt thereof.

In another embodiment, the adjuvant composition used in preparing the mixture for applying the herbicidal composition contains:

(a) at least one monocarboxylic acid or a monocarboxylate thereof; and

(b) alkali metal phosphate;

wherein the molar ratio of monocarboxylic acid or monocarboxylate thereof to alkali metal phosphate is from about 1:5 to 5:1 and

where the composition contains a monocarboxylic acid or its monocarboxylate in an amount (acid equivalent weight) of approximately 2 wt. % to approximately 40 wt. % composition.

In another embodiment, the adjuvant composition used in preparing the aqueous mixture for applying the herbicidal composition contains

(a) acetic acid or an agriculturally acceptable salt thereof, and

(b) alkali metal phosphate;

wherein the molar ratio of acetic acid or an agriculturally acceptable salt thereof to alkali metal phosphate is from about 1:5 to about 5:1.

In another embodiment, the adjuvant composition used in preparing the mixture for applying the herbicidal composition contains:

(a) acetic acid or an agriculturally acceptable salt thereof, and

(b) alkali metal phosphate;

wherein the molar ratio of acetic acid or an agriculturally acceptable salt thereof to alkali metal phosphate is from about 1:5 to about 5:1 and

where the composition contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of about 2 wt. % up to 40 wt. % composition.

In another embodiment, the invention relates to an adjuvant composition used in preparing a mixture for applying a herbicidal composition, wherein the adjuvant composition contains acetic acid or an agriculturally acceptable salt thereof in an amount (acid equivalent weight) of from about 2% to about 75% by weight. % composition. In one aspect, the amount is from about 10% to about 75 wt. % composition. In another aspect, the amount is from about 20% to about 75 wt. % composition. In another aspect, the amount is from about 30% to about 75 wt. % composition.

In various embodiments of the adjuvant composition, the composition is a dry powder composition.

In various embodiments of the adjuvant composition, the composition is a liquid composition, particularly an aqueous composition.

In various embodiments of the adjuvant composition, the composition contains a non-ammoniated monocarboxylate or acetate salt. In other embodiments, the salt is an alkali metal salt, such as an alkali metal salt. In other embodiments, the salt is a potassium salt or a sodium salt, such as potassium acetate and sodium acetate.

In various embodiments of the adjuvant composition, the alkali metal phosphate is potassium monohydrogen phosphate.

In various embodiments of the adjuvant composition, the composition contains potassium acetate and potassium monohydrogen phosphate.

I. Methods for reducing the volatility of an auxin herbicide

Another embodiment of the present invention relates to a method for reducing the volatility of an auxin herbicide. The method typically includes the step of contacting the auxinic herbicide with a volatility-reducing amount of a monocarboxylic acid or a monocarboxylate thereof, thereby reducing the volatility of the auxinic herbicide.

In one embodiment, the contacting step satisfies at least one of the following conditions:

the molar ratio of the monocarboxylic acid or its monocarboxylate to the auxin herbicide upon contact is from about 1:10 to about 10:1;

the weight ratio of the monocarboxylic acid or monocarboxylate thereof, on an acid equivalent basis, to the auxin herbicide upon contact is from about 1:10 to about 5:1 and

the amount of monocarboxylic acid or monocarboxylate thereof contacting the auxinic herbicide is sufficient to reduce the concentration of the volatile auxinic herbicide in the vapor phase by at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80 %, 90% or 95% relative to the vapor phase concentration of the volatile auxin herbicide for the auxin herbicide in the absence of the monocarboxylic acid or its monocarboxylate.

Evaporation can be measured by conventional methods known to those skilled in the art. In one such method, for example, a gas stream is passed over the auxin herbicide composition and the auxin herbicide is evaporated from the composition into the gas stream, which is then quantitatively analyzed for auxin herbicide content by methods known in the art. In another method, the auxin herbicide composition is distilled and the distillation condensate and/or the distilled composition is analyzed for auxin herbicide content. In yet another method, the volatility of an auxin herbicide is quantitatively analyzed by examining the plant's response to a selected susceptible species, which should be known to one of ordinary skill in the art.

The addition of a monocarboxylic acid or its monocarboxylate at the loading amounts discussed above to the herbicidal compositions of the present invention is believed to effectively reduce auxin herbicide volatility and associated crop damage without significantly reducing the effectiveness of the auxin herbicide.

In one embodiment, no reduction in auxin herbicide effectiveness was observed for the herbicidal composition of the present invention relative to a control composition containing no monocarboxylic acid or monocarboxylate thereof, but otherwise having the same composition.

In another embodiment, the auxin herbicide potency of the herbicidal composition of the present invention is at least about 80%, 85%, 90%, 95%, or 99% of the auxin herbicide potency of a control composition containing no monocarboxylic acid or monocarboxylate thereof, but otherwise having the same compound.

In another embodiment, a reduced degree of crop damage is observed for the herbicidal composition of the present invention relative to a reference composition not containing the monocarboxylic acid or its monocarboxylate but otherwise having the same composition.

In another embodiment, the degree of crop damage associated with the herbicidal composition of the present invention is reduced by about 90%, 80%, 70%. 60% or 50% of the crop damage associated with a control composition containing no monocarboxylic acid or its monocarboxylate but otherwise having the same composition.

In another embodiment, no reduction in crop damage and no reduction in auxin herbicide effectiveness is observed for the herbicidal compositions of the present invention relative to a control composition containing no monocarboxylic acid or monocarboxylate thereof but otherwise having the same composition.

In another embodiment, a herbicidal composition comprising a monocarboxylic acid or a monocarboxylate thereof is sufficient to provide both commercially acceptable weed control and a commercially acceptable degree of crop damage.

The "commercially acceptable degree of weed control" varies with the type of weed, the severity of the weed, the environmental conditions and the associated crop. Commercially effective weed control is generally defined as at least about 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or even greater weed control than 95%. Although 80-85% or more of the weeds are typically commercially preferred, commercially significant weed control can occur at lower levels, especially in the case of some highly toxic, herbicide-resistant plants. The term "weed suppression" as used herein refers to any observable level of inhibition of plant growth, which may include one or more of (1) killing, (2) inhibiting growth, reproduction or proliferation, and (3) eliminating, destroying or same other reduction

distribution and activity of plants. Weed suppression can be measured by any of various methods known in the art. For example, weed suppression can be determined as a percentage compared to untreated plants using a standard procedure in which a visual assessment of plant mortality and reduced growth is performed by a person skilled in the art specially trained to make such assessments. In another method, weed suppression is assessed as the average percentage reduction in plant weight between treated and untreated plants. Commercial weed control is preferably achieved no more than 30 days after application (DAT), for example 18 to 30 DAT.

The "commercially acceptable degree of crop damage" for the present invention similarly varies depending on the crop species. A commercially acceptable degree of crop damage is generally considered to be less than about 20%, 15%, 10%, or even less than about 5%. Crop damage can be measured by any method known in the art, such as the method described above for determining weed suppression. Crop damage is preferably no more than 10-20% after no more than 30 DAT, for example 3 to 21 or 3 to 30 DAT.

J. Methods for inhibiting the growth of auxin-sensitive plants

Another embodiment of the present invention relates to methods for inhibiting the growth of auxin-sensitive plants, especially plants growing in a crop field and/or adjacent to a crop field. The methods typically include applying to auxin-sensitive plants an aqueous mixture of a herbicidal composition containing at least one auxin herbicide; at least one monocarboxylic acid or a monocarboxylate thereof; and optionally a non-auxic herbicide, wherein the application mixture has reduced volatility of the auxinic herbicide compared to an identical application mixture not containing the monocarboxylic acid or its monocarboxylate.

An aqueous mixture of a herbicidal composition applied to plants susceptible to auxin can be represented, for example, in the following form:

(a) in the form of a ready-to-use aqueous herbicidal composition that can be applied without the need for further dilution with water or other preparation;

(b) as a mixture for applying the herbicidal composition obtained by diluting with water any of the concentrates of the herbicidal composition within the scope of the present description;

(c) as a mixture for applying the herbicidal composition obtained by mixing two or more separate components with water (for example, a tank mixture);

(d) in the form of an application mixture of a herbicidal composition prepared by introducing separate feed streams into a spray or application system such that the feed streams are mixed immediately prior to use, or

(e) any other species reasonably adapted for application to auxin-sensitive plants of a herbicidal composition containing an auxin herbicide mixed with a monocarboxylic acid or its carboxylate.

In one embodiment, methods for inhibiting the growth of auxin-sensitive plants include the steps of:

(a) providing an aqueous herbicidal mixture for application by diluting with water a herbicidal composition concentrate of any of the herbicidal composition concentrates described herein, and

(b) applying a herbicidally effective amount of the mixture for application to auxin-sensitive plants.

In another embodiment, the preparation step does not include separately introducing a pH-lowering agent (eg, an acidifying agent) with the concentrate and water during preparation of the application mixture; wherein the pH-lowering agent is an agent 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.

In one embodiment, methods for inhibiting the growth of auxin-sensitive plants include the steps of:

(a) mixing the source of the auxin herbicide; source of monocarboxylic acid or its monocarboxylate and water to obtain an aqueous herbicide mixture for application and

(b) applying a herbicidally effective amount of the mixture for application to auxin-sensitive plants;

wherein the mixture to be applied 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 weight ratio of the monocarboxylic acid or monocarboxylate thereof, on an acid equivalent basis, to the auxinic herbicide is from about 1:10 to about 5:1;

the application mixture contains a monocarboxylic acid or its monocarboxylate in an amount (acid equivalent weight) of from about 0.01% to about 25 wt. % of mixture for application;

the concentration of the monocarboxylic acid or its monocarboxylate is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L and

the application mixture contains a monocarboxylic acid or a monocarboxylate thereof in an amount sufficient to reduce the concentration of a volatile auxin herbicide in the vapor phase surrounding the application mixture by at least about 10% relative to the concentration of a volatile auxin herbicide in the vapor phase surrounding an identical application mixture, not containing monocarboxylic acid or its monocarboxylate.

In one aspect, the application mixture contains a monocarboxylic acid or monocarboxylate thereof in an amount (acid equivalent weight) of from about 0.1% to about 25% by weight. % of mixture to be applied.

In another embodiment, methods for inhibiting the growth of auxin-sensitive plants include the steps of:

(a) mixing the source of the auxin herbicide; a source of non-auxin herbicide or an agriculturally acceptable salt thereof; a source of monocarboxylic acid or its monocarboxylate; and water to obtain an aqueous herbicide mixture for application and

(b) applying a herbicidally effective amount of the mixture for application to auxin-sensitive plants;

wherein the mixture to be applied 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 weight ratio of the monocarboxylic acid or monocarboxylate thereof, on an acid equivalent basis, to the auxinic herbicide is from about 1:10 to about 5:1;

the application mixture contains a monocarboxylic acid or its monocarboxylate in an amount (acid equivalent weight) of from about 0.01% to about 25 wt. % of mixture for application;

the concentration of the monocarboxylic acid or its monocarboxylate is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L and

the application mixture contains a monocarboxylic acid or a monocarboxylate thereof in an amount sufficient to reduce the concentration of a volatile auxin herbicide in the vapor phase surrounding the application mixture by at least about 10% relative to the concentration of a volatile auxin herbicide in the vapor phase surrounding an identical application mixture, not containing monocarboxylic acid or its monocarboxylate.

In one aspect, the application mixture contains a monocarboxylic acid or monocarboxylate thereof in an amount (acid equivalent weight) of from about 0.1% to about 25% by weight. % of mixture to be applied.

When methods of inhibiting the growth of auxin-susceptible plants include the use of an application mixture of a herbicidal composition containing a non-auxin herbicide, the application mixture typically satisfies one or more of the following conditions:

the sum of the auxinic herbicide concentration and the non-auxinic herbicide concentration is from about 1 gram (acid equivalent weight)/L to about 50 grams (acid equivalent weight)/L;

the weight ratio of auxinic herbicide to non-auxinic herbicide on an acid equivalent basis is from about 1:5 to about 2:1 and

the weight ratio of the monocarboxylic acid or carboxylate thereof, calculated as acid equivalent, to the auxinic herbicide is from about 1:10 to about 5:1.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants, the application mixture contains a non-auxin herbicide selected from the group consisting of acetochlor, glyphosate, glufosinate, flumioxazin, fomesafen, and agriculturally acceptable salts thereof. In one embodiment, the application mixture contains glyphosate or an agriculturally acceptable salt thereof. In another embodiment, the application mixture contains glufosinate or an agriculturally acceptable salt thereof.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants, 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.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants, the auxin herbicide is dicamba or an agriculturally acceptable salt or ester thereof.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants, the auxin herbicide is 2,4-D or an agriculturally acceptable salt or ester thereof.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants, the treatment mixture contains a monocarboxylate salt.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants, the treatment mixture contains acetic acid or an agriculturally acceptable salt thereof.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants, the monocarbosylate or acetate salt is a non-ammoniated salt. In still other embodiments, the salt is an alkali metal salt. In yet other embodiments, the salt is a potassium salt. In yet other embodiments, the salt is a sodium salt.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants, the treatment mixture further comprises a buffer.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants, the treatment mixture further comprises an alkali metal phosphate, such as potassium monohydrogen phosphate.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants, the mixing step does not include separately administering the pH-lowering agent with the source of the auxin herbicide; a source of monocarboxylic acid or monocarboxylate thereof and water during preparation of the treatment mixture; wherein the pH-lowering agent is an agent that is capable of lowering the pH of the treatment mixture in the absence of any buffering provided by other components of the treatment mixture.

In various embodiments of the described methods for inhibiting the growth of auxin-sensitive plants in which the treatment mixture contains a non-auxin herbicide, the mixing step does not comprise separately adding the pH-lowering agent to the source of the auxin herbicide; source of non-auxin herbicide; a source of monocarboxylic acid or monocarboxylate thereof, and water during preparation of the treatment mixture; wherein the pH-lowering agent is an agent that is capable of lowering the pH of the treatment mixture in the absence of any buffering provided by other components of the treatment mixture.

In the described methods, the application mixture is applied to auxin-sensitive plants at an application rate sufficient to obtain a commercially acceptable degree of weed control. The appropriate application rate for the mixture used can be easily determined by one skilled in the art and is usually expressed as the amount of auxin herbicide per unit area treated, for example, grams per acid equivalent per hectare (g ae/hectare). Depending on the plant species and growing conditions, the period of time required to achieve a commercially acceptable degree of plant growth inhibition can be as short as a week or as long as three weeks, four weeks or one month. Typically a period of approximately two to three weeks is required for the full effect of the auxin herbicide to occur.

The timing of application can be changed. The application mixture can be applied, for example, before planting a crop plant, for example, about two to about three weeks before planting auxin-susceptible crop plants or crop plants that do not exhibit the auxin herbicide resistance trait. Crop plants that are not susceptible to certain auxin herbicides (such as corn or plants showing signs of auxin herbicide resistance), however, generally do not have a preplant restriction, and the application mixture can be applied immediately before planting such crops.

Plants susceptible to auxin can be weeds or crops. Agricultural crops include, for example, vegetables, cereals, flowering plants and root crops. Crops further include hybrids, inbreds, and transgenic or genetically modified plants.

In some embodiments, the crop is an auxin-tolerant species that is resistant to auxin herbicides, or is a transgenic species that has an auxin resistance trait (eg, dicamba). Examples of crops include dicamba-resistant corn, cotton, or soybeans. Dicamba-resistant crops may also have one or more additional traits, including, but not limited to, herbicide resistance (e.g., resistance to other auxin herbicides (e.g., 2,4-D or fluoroxypyr), glyphosate, glufosinate, herbicides - acetolactate synthase inhibitors (for example, imazamox, imazethapyr, imazaquin and imazapic), acetyl-CoA carboxylase inhibitors (for example, zethoxydim and clethodim), etc.); resistance to insects such as Bacillus thuringiensis (Bt); resistance to high oil content; high lysine content; high starch content, high nutritional value and/or drought resistance.

In some embodiments, the weeds and/or crops are tolerant to glyphosate or have the property of being resistant to glyphosate. Examples of these include glyphosate-resistant corn, cotton or soybeans.

In some embodiments, the crop plants have certain properties in the stacked state, such as resistance to dicamba and glyphosate; resistance to dicamba and glufosinate; resistance to dicamba and acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS); resistance to dicamba, glyphosate and glufosinate; resistance to dicamba, glyphosate and ALS or AHAS; resistance to dicamba, glufosinate and ALS or AHAS; or resistance to dicamba, glyphosate, glufosinate, and ALS or AHAS.

In some embodiments, the plants may additionally have other herbicide, insect, and disease resistance properties, as well as combinations of such properties. For example, plants may have dicamba, 2,4-D, or fluoroxypyr resistance properties.

K. Methods for regulating the movement of herbicide from the application site

Another embodiment of the present invention relates to a method of controlling the movement of an auxin herbicide from an application site by contacting the auxin herbicide with a volatility-reducing effective amount of a monocarboxylic acid or a monocarboxylate thereof prior to application of the auxin herbicide.

In one embodiment, the method includes the steps of:

(a) providing an aqueous mixture for application of a herbicidal composition containing an auxin herbicide; monocarboxylic acid or its monocarboxylate; water and optionally a source of non-auxin herbicide, and

(b) applying a herbicidally effective amount of the mixture for application to auxin-sensitive plants;

wherein the mixture to be applied 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 weight ratio of the monocarboxylic acid or monocarboxylate thereof, on an acid equivalent basis, to the auxinic herbicide is from about 1:10 to about 5:1;

the application mixture contains a monocarboxylic acid or its monocarboxylate in an amount (acid equivalent weight) of from about 0.01% to about 25 wt. % of mixture for application;

the concentration of the monocarboxylic acid or its monocarboxylate is from about 1 gram (acid equivalent weight)/L to about 250 grams (acid equivalent weight)/L and

the application mixture contains a monocarboxylic acid or a monocarboxylate thereof in an amount sufficient to reduce the concentration of a volatile auxin herbicide in the vapor phase surrounding the application mixture by at least about 10% relative to the concentration of a volatile auxin herbicide in the vapor phase surrounding an identical application mixture, not containing monocarboxylic acid or its carboxylate.

In one aspect, the application mixture contains a monocarboxylic acid or monocarboxylate thereof in an amount (acid equivalent weight) of from about 0.1% to about 25% by weight. % of mixture to be applied.

L. Methods of advising on the use of auxin herbicide

Another embodiment of the present invention relates to methods of advising an individual regarding the preparation and/or application of an auxin herbicide.

In one embodiment, the invention relates to a method of advising an individual to apply an auxin herbicide to auxin-susceptible plants, the method comprising:

(a) identification of the source of the auxin herbicide;

(b) instructing the individual to obtain an aqueous mixture for application of the herbicidal composition from a source of auxin herbicide; and

(c) additionally instructing the individual to replenish the application mixture with a monocarboxylic acid or its monocarboxylate before applying the mixture to auxin-sensitive plants.

In another embodiment, the invention relates to a method of advising an individual to apply an auxin herbicide to auxin-susceptible plants, the method comprising:

(a) identification of the source of the auxin herbicide;

(b) identification of the source of the monocarboxylic acid or its monocarboxylate, and

(c) instructing the individual to prepare an aqueous mixture of a herbicidal composition from a source of auxin herbicide and a source of monocarboxylic acid or monocarboxylate thereof for application to auxin-sensitive plants.

The source of the monocarboxylic acid or its monocarboxylate may be, for example, a separate source such as a previously described adjuvant of the herbicidal composition or even a source that provides in situ formation of the monocarboxylic acid or its monocarboxylate in the herbicidal composition application mixture.

From the invention described in detail, it will be apparent that modifications and variations are possible without departing from the scope of the invention as defined in the appended claims.

M. Examples

The following non-limiting examples are presented to further illustrate the present invention. It should be noted that the following example compositions are presented based on the components initially mixed to form the specified reservoir mixture or concentrate. It is contemplated that various embodiments of the present invention include such initial compositions as well as any corresponding compositions resulting from the interaction of the components after they are mixed, such as a composition in which a monocarboxylic acid salt is formed in situ by mixing the monocarboxylic acid with a neutralizing base.

Example 1-A: Mixing Tank Compositions (Dicamba+Glyphosate)

Unless otherwise indicated, the tank-mix herbicidal compositions described in Examples 1-A, 1-B and 1-C were prepared using CLARITY® (dicamba DGA from BASF), ROUNDUP POWERMAX® (potassium glyphosate from Monsanto), BANVEL® (dicamba DMA from BASF), DURANGO® DMA® (glyphosate DMA from Dow AgroSciences), LIBERTY® (glufosinate ammonium from Bayer CropScience), and/or 2,4-D-amine (Albaugh) by sequentially adding each indicated herbicide to water and stirring. These tank mix formulations containing additional tank mix adjuvants such as potassium acetate (Sigma), potassium monohydrogen 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 source, such as glyphosate IPA and dicamba MEA, were typically prepared by mixing the herbicidal acid with the desired amine. The ratio of herbicidal acid to amine is usually approximately 1:1. In some cases a slight excess of amine is desirable. DGA as used in these examples refers to diglycolamine; DMA refers to dimethylamine; IPA refers to isopropylamine and MEA refers to monoethanolamine.

Herbicidal compositions in mixing tanks obtained by the method described above are listed below in Tables 1-1 to 1-15.

For the mixing tank compositions in Tables 1-16 to 1-19, a monocarboxylic acid salt (eg, potassium acetate) was formed in situ by mixing the monocarboxylic acid with a neutralizing base. The compositions were prepared by mixing the herbicide(s) with water, followed by the addition of a monocarboxylic acid and then a neutralizing base. Although a specific order of addition of the ingredients is not required to obtain the final composition, the order of addition described above may be beneficial in reducing the generation of heat resulting from mixing the ingredients. The neutralizing base (potassium hydroxide in the following compositions) was added at 45 w/w. % aqueous solution.

Example 1-B: Mixing Tank Compositions (Dicamba+Glufosinate)

Example 1-C: Mixing Tank Compositions (Dicamba)

The compositions shown above in Tables 1-37, 1-38 and 1-40 (Compositions 364-5, 364-6 and 364-4, respectively) were prepared by mixing an appropriate amount of the composition shown below in Table 2-17 (Composition 871- 5) with additional components and an amount of water sufficient to provide a final dicamba concentration of 1.2% e.e.

Example 1-D: Acetic acid adjuvant

An example of an acetic acid adjuvant used in the tank mixing production of dicamba is described below in Table 1-41.

Example 2-A: Liquid Concentrate Formulations (Dicamba)

Compositions in the form of liquid concentrates are described in examples 2-A, 2-B, 2-C and 2-D.

The potassium acetate used in the compositions in Tables 2A-1-29 to 2A-1-32 was prepared by adding the required amount of glacial acetic acid to the required amount of potassium hydroxide (45 w/w% solution) in an ice bath without allowing the temperature to increase. solution above 60°C. The previously prepared potassium acetate was then added to the solution containing the herbicide(s). The ratio shown in the tables below is the ratio on a molar basis. For example, "50/50 AcOH/KOH" means a molar ratio (M) of 1:1 M acetic acid to potassium hydroxide. The compositions shown in the tables below were prepared by adding the required amount of each ingredient and stirring the mixture for approximately 20 minutes.

Alternatively, the monocarboxylic acid salt can be prepared by adding the monocarboxylic acid to a solution containing the herbicide(s), followed by the addition of a neutralizing base. Although a specific order of addition of the ingredients is not required to obtain the final composition, the order of addition described above may be beneficial in reducing the generation of net heat when mixing the ingredients.

Example 2-B: Liquid Concentrate Formulations (Dicamba+Glyphosate)

Herbicidal compositions containing dicamba DGA and glyphosate MEA were prepared by mixing CLARITY® with glyphosate and water. After stirring the mixture for five minutes, the surfactants AGM550 and Agnique PG8107-G were added, followed by the addition of iron (III) citrate (to reduce necrosis of some crops) and antifoam agent SAG 1572 and the mixture was mixed for an additional 30 minutes. Premix compositions that also contain additional adjuvants such as potassium acetate were prepared as described above with the modification of replacing water with the required amount of aqueous adjuvant. The glyphosate MEA 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 for the dicamba/glyphosate premix composition is shown in Table 2-1.

Dicamba/glyphosate premixes containing additional adjuvants, such as potassium acetate, were typically prepared by adding the required amount of aqueous adjuvant solution to the premix prepared as described below in Tables 2-2 and 2-3.

Potassium acetate, used in the preparations of tables 2-5 to 2-13, was prepared by adding the required amount of glacial acetic acid to the required amount of potassium hydroxide (45 wt./wt.% solution) in an ice bath without the possibility of increasing the temperature of the solution above 60 ° C . The ratio shown in the tables below is the ratio on a molar basis. For example, "50/50 AcOH/KOH" means a 1:1 molar ratio (M) of acetic acid to potassium hydroxide. The compositions shown in the tables below were prepared by adding the required amount of each ingredient and stirring the mixture for approximately 20 minutes. Alternatively, the monocarboxylic acid salt can be prepared by adding the monocarboxylic acid to a solution containing the herbicide(s), followed by the addition of a neutralizing base.

The Fe supplement listed in Tables 2-8 to 2-13 (added to reduce necrosis in some crops) was prepared by mixing iron(III) sulfate and citric acid.

Example 2-C: Liquid Concentrate Formulations (Dicamba)

Example 2-D: compositions in the form of liquid concentrates (dicamba + glyphosate)

Example 2-E: compositions in the form of dry concentrates (dicamba)

Dry granules were prepared having the compositions shown in Table 2-30 and Table 2-31. Dicamba sodium salt and sodium acetate were mixed in a mixer. PEG 8000, antifoam and water were added to the mixer and mixing was continued. The amount of water added was sufficient to obtain a paste suitable for extrusion. The paste was extruded under pressure through 1 mm holes to obtain granules. The granules were extruded a total of three times to obtain granules that were not too dry. The final extruded granules were then dried in a fluid bed dryer at 70° C., resulting in granules having a whitish color.

Example 3: Dicamba Volatility Measurement (Humid)

Humidomes obtained from Hummert international (part number 14-3850 for humidomes and 11-3-50-1 for flat tray 1020) were modified by cutting a 2.2 cm diameter hole at one end approximately 5 cm from the top to allow insertion of a glass air sampling tube (22 mm outer diameter) containing a polyurethane foam (PUF) filter. The sampling tube was secured with a VITON o-ring on each side of the humidome wall. The tube for collecting an air sample, external to the humidome, was equipped with a pipe system that was connected to a vacuum manifold immediately before sampling.

The flat tray under the humidom was filled with 1 liter of sifted dry or wet 50/50 soil (50% red soil and 50% US 10 field soil) to a depth of approximately 1 cm. The bottom of the flat tray containing the dicamba preparation on the soil was covered with the lid of the humidom and the lid was secured with clamps . The collected humidomas were placed in a temperature and humidity controlled environment and connected to a vacuum manifold via an air sampling line. Air was sampled through humid and PUF at a rate of 2 liters per minute (LPM) for 24 hours, at which point air sampling was stopped. The humidomas 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.

To measure the concentration of dicamba in the gas phase (air), which evaporates from the sprayed solutions, compositions were prepared that contained 1.2% ce. dicamba, which is equivalent to an application rate of 0.45359 kg (1.0 lb)/anhydrous ae. at 37.85 L (10 gal) per 0.405 ha (1 acre) (GPA). When glyphosate was added or was part of the formulation, glyphosate was present at a concentration of 2.4% a.e. or 9.0718 kg (2.0 lb)/anhydrous ae. When 2,4-D was added or was part of the formulation, 2,4-D was present at 2.4% a.e. or 9.0718 kg (2.0 lb)/anhydrous ae. at an application rate of 37.85 L (10 gallons) per 0.405 ha (1 acre) (GPA). The growth chambers were set at 35°C and 40% relative humidity (RH). Each composition was used to spray four separate boxes of humidom to have measurements in 4 replicates for each preparation. Tables 3-1 through 3-12 below present the average dicamba air concentrations for the formulations tested. When dicamba concentrations were below detection limits, those concentrations are designated “nd” in the tables below.

The results reported above for the di- and tricarboxylic acids tested (oxalic acid, citric acid and succinic acid) indicate that these acids did not reduce the volatility of dicamba. In addition, malic acid was tested and it also did not reduce the volatility of dicamba.

Example 4: Dicamba Volatility Measurement (Plant Response)

Herbicidal compositions were sprayed onto eight glass Petri dishes with a diameter of 90 mm. Eight Petri dishes were immediately placed on a plastic tray along with two Roundup Ready soybean plants at development stage V1-V1.5 as indicators. The plastic trays were then covered with plastic domes, sealed with clamps around the edges and placed in culture chambers at a set temperature and relative humidity (day 0.56°C (85°F) (16 hours of light)), (night -7.78°C (70°F) (8 hours dark) and 40% relative humidity for 24 hours. After 24 hours, the plants were freed from their domes and transferred to greenhouses. Indicator plants were assessed for visual symptoms usually on days 5, 7 and 14 after treatment.

Plant response results for compositions containing dicamba are listed in Tables 4-1, 4-2 and 4-3.

Example 5: Measuring Herbicide Efficiency

The herbicidal effectiveness of the compositions of the present invention can be assessed through conventional greenhouse and/or field trials. Herbicidal effectiveness can be measured as percentage "inhibition" according to a standard procedure in the art, which reflects a visual assessment of plant death and reduced growth compared to untreated plants, made by technicians specially trained to make and record such observations. In all cases, a single technician performs all percentage inhibition assessments in any one experiment or run. Such measurements are reliable and regularly reported by Monsanto Technology LLC during its herbicide business.

Selecting application rates that are biologically effective for a particular auxin herbicide is within the knowledge of the average agricultural scientist. One skilled in the art will also be aware that the condition of individual plants, weather and growing conditions, and the particular exogenous chemical and formulation thereof selected will influence the effectiveness of weed control and associated crop damage achieved by the practice of the present invention. Suitable application rates for the auxin herbicides used may depend on all of the above conditions. With respect to the application of the method of the present invention, much information is known regarding suitable auxin application rates, and the weed control practitioner can select auxin application rates that are herbicidally effective for a particular weed species at particular growth stages under particular environmental conditions.

Performance in greenhouse tests, typically at application rates of exogenous chemicals that are lower than rates typically effective in the field, is a proven indicator of consistency of performance in the field at normal application rates.

The compositions of the present invention can be applied to plants by spraying using any conventional liquid spray device, such as spray tips, fine mist sprayers, or the like. The compositions of the present invention can be used in precision farming methods that employ a device to vary the amount of exogenous chemical applied to different parts of a field depending on parameters such as the specific plant species present, soil composition, and the like. In one embodiment of such methods, a universal, positionable system operating with a sprinkler mechanism can be used to apply the required amount of composition to different parts of the field.

The composition, when applied to plants, is preferably diluted sufficiently so that it can be easily sprayed using standard agricultural spray equipment. Preferred application rates for the present invention vary depending on a number of factors, including the type and concentration of the active ingredient and the plant species being suppressed. Suitable rates for applying the aqueous composition to a foliage area may range from about 25 to about 1000 liters per hectare (1/ha), where the composition is applied by spraying.

Preferred application rates for aqueous solutions range from about 50 to about 300 L/ha.

Many exogenous chemicals (including auxin herbicides) must be taken up by living plant tissue and translocated within the plant to produce the desired biological (eg, herbicidal) effect. Thus, it is important that the herbicidal formulation is not applied in such a way that excessive damage and interference with the normal functioning of local plant tissue occurs so quickly that movement is reduced. However, some limited degree of local damage may have little or even beneficial effect on the biological effectiveness of some exogenous chemicals.

The results obtained with the application of the composition to hemp sesbania (SETVI), Theophrastus funiculus (ABUTH) and hemp sesbania (SEBEX) are shown in Tables 5-1, 5-2 and 5-3, respectively. In each case, application rates were 280 g ae/ha for dicamba and 560 g ae/ha for glyphosate, the result reported being the average of results obtained from six separate applications.

Example 6: Herbicidal effectiveness on ABUTH (Theophrastus's funiculus) and ELEIN (Eleusina indica)

The tank mix herbicidal compositions listed in the tables below were prepared using CLARITY® (dicamba DGA from BASF) and ROUNDUP POWERMAX® (potassium glyphosate from Monsanto) by sequentially adding each specific herbicide to water and mixing the mixture. Reservoir mixtures containing potassium acetate were prepared as described in Example 1.

Weed seeds were planted in 22.58 cm ² (3.5 sq. in.) plastic pots filled with red soil (Sun Gro, Believue, WA) containing 100 g/2.83 m ³ (100 cu ft.) slow release fertilizer. release of Osmocote 14-14-14. Ten to fifteen seeds were planted at a depth of approximately 1.27 cm (0.5 in) and covered loosely with potting medium. The pots were placed in a controlled environment provided with subsoil irrigation. Growth conditions were 27°C during the day and 21°C at night with fourteen hours of supplemental light (approximately 600 microeinsteins). After germination and emergence from the growing environment, plants were thinned to produce one plant per pot. Pots that contained plants that were similar in appearance, size and vigor were selected for treatment. Plants were typically 10.16–20.32 cm (4–8 in) tall at the time of herbicide treatment. The compositions were applied to the plants by a track sprayer, typically using a Teejet 9501E flat spray nozzle or similar nozzle with a minimum of 165.6 kPa (24 lb) of air pressure per 6.452 cm ² (sq. in.). The spray tip was 16 inches above the top of the plants and a volumetric flow rate of approximately 10 gallons per acre (93 L per hectare) was applied. Each formulation was applied at three application rates and herbicide damage was assessed 21 days after application.

The herbicidal premix compositions listed in the table below were prepared as previously described in Example 2.

This specification uses examples to describe the invention, including the best method, and this description also allows anyone skilled in the art to practice the invention, including the manufacture and use of any devices or systems and the performance of any included methods. The patentable scope of an invention is defined by the claims and may include other examples that come to mind to one skilled in the art. Such other examples are intended to be within the scope of the claims if they have structural elements that do not differ from the verbatim expression of the claims, or if they include equivalent structural elements with minor differences from the verbatim expressions of the claims.

Claims (11)

1. Combination packaging for obtaining a herbicidal composition, where the combination packaging includes a first container containing dicamba or an agriculturally acceptable salt or ester thereof, and a second container containing acetic acid or an agriculturally acceptable salt thereof. 2. The combination package of claim 1, wherein the first container contains a liquid composition containing dicamba or an agriculturally acceptable salt or ester thereof. 3. The combination package of claim 1, wherein the first container contains a dry composition containing dicamba or an agriculturally acceptable salt or ester thereof. 4. Combined according to any one of paragraphs. 1-3, wherein the package further comprises a third container containing glyphosate or an agriculturally acceptable salt thereof. 5. The combination package of claim 4, wherein the third container contains a liquid composition containing glyphosate or an agriculturally acceptable salt thereof. 6. The combination package according to claim 4, where the third container contains a dry composition containing glyphosate or an agriculturally acceptable salt thereof. 7. Combined packaging according to any one of paragraphs. 1-3, wherein the package further comprises a third container containing glufosinate or an agriculturally acceptable salt thereof. 8. The combination package of claim 7, wherein the third container contains a liquid composition containing glufosinate or an agriculturally acceptable salt or ester thereof. 9. The combination package of claim 7, wherein the third container contains a dry composition containing glufosinate or an agriculturally acceptable salt or ester thereof.