# US 11,297,834 B2 · Low volatility herbicidal compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,297,834 B2 - Document ID: US11297834B2 - Status: Granted - Kind: B2 - Application number: 16/226,856 - Filed: 2018-12-20 - Published: 2019-06-27 - Granted: 2022-04-12 - Earliest claimed: 2012-11-05 - Assignees: Monsanto Technology LLC - Applicants: Monsanto Technology LLC - Inventors: John W. Hemminghaus; Alison MacInnes; Daniel R. Wright; Junhua Zhang - Web page: https://patentgrep.com/patent/US11297834B2 ## CPC - A01N 37/04: polybasic - A01N 37/02: Saturated carboxylic acids or thio analogues thereof; Derivatives thereof - A01N 37/40: having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system - A01N 39/04: Aryloxy-acetic acids; Derivatives thereof - A01N 57/20: containing acyclic or cycloaliphatic radicals - G09B 19/00: Teaching not covered by other main groups of this subclass (teaching or practice apparatus for gun-aiming or gun-laying F41G3/26) - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - G09B: EDUCATIONAL OR DEMONSTRATION APPLIANCES; APPLIANCES FOR TEACHING, OR COMMUNICATING WITH, THE BLIND, DEAF OR MUTE; MODELS; PLANETARIA; GLOBES; MAPS; DIAGRAMS (devices for psychotechnics or for testing reaction times A61B5/16; games, sports, amusements A63; projectors, projector screens G03B) ## Abstract The present invention relates generally low volatility herbicidal compositions comprising at least one auxin herbicide and at least one monocarboxylic acid, or monocarboxylate thereof. The invention further relates generally to methods for preparing and using such low volatility herbicidal compositions, including methods for controlling auxin-susceptible plant growth on agricultural and non-agricultural lands. ## Claims ### Claim 1 A method for preparing an herbicidal composition, the method comprising: combining (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) a monocarboxylate, and (iii) water, wherein the auxin herbicide is selected from dicamba, or an agriculturally acceptable salt or ester thereof, 2,4-D, or an agriculturally acceptable salt or ester thereof, and mixtures thereof, and the monocarboxylate is selected from the group consisting of a formate salt, an acetate salt, a propionate salt, a benzoate salt, and combinations thereof; wherein said combining comprises: providing a liquid herbicidal composition concentrate comprising from about 120 to about 600 g a.e./L of auxin herbicide; diluting the herbicidal composition concentrate comprising the auxin herbicide with water, thereby forming an herbicidal composition comprising from about 0.1 g a.e./L to about 50 g a.e./L of auxin herbicide; and adding the monocarboxylate to the herbicidal composition, wherein the herbicidal composition comprises an amount of the monocarboxylate sufficient to provide enhanced protection from off-target crop injury as compared to an otherwise identical herbicidal composition lacking the monocarboxylate while maintaining comparable herbicidal efficacy on auxin-susceptible plants located in the target area. ### Claim 2 (depends on 1) The method of claim 1, wherein the monocarboxylate is an acetate salt. ### Claim 3 (depends on 1) The method of claim 1, the method further comprising combining a non-auxin herbicide with the (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) an acetate salt, and (iii) water, wherein the non-auxin herbicide is selected from glyphosate, or an agriculturally acceptable salt thereof and glufosinate, or an agriculturally acceptable salt thereof. ### Claim 4 (depends on 3) The method of claim 3, wherein said combining comprises: diluting an herbicidal composition concentrate comprising the auxin herbicide and the non-auxin herbicide, with water; and adding the acetate salt to the diluted concentrate. ### Claim 5 (depends on 3) The method of claim 3, wherein said combining comprises: adding the acetate salt to an herbicidal composition concentrate comprising the auxin herbicide and the non-auxin herbicide; and diluting the herbicidal composition concentrate. ### Claim 6 (depends on 3) The method of claim 3, wherein said combining comprises: diluting an herbicidal composition concentrate comprising the auxin herbicide, with water; adding the acetate salt to the diluted concentrate; and adding the non-auxin herbicide to the diluted concentrate. ### Claim 7 (depends on 2) The method of claim 2, wherein said combining comprises: adding the acetate salt to an herbicidal composition concentrate comprising the auxin herbicide; adding the non-auxin herbicide to the herbicidal composition concentrate comprising the auxin herbicide; and diluting the herbicidal composition concentrate. ### Claim 8 (depends on 2) The method of claim 2, wherein the acetate salt is a potassium salt or a sodium salt. ### Claim 9 (depends on 2) The method of claim 2, wherein the herbicidal composition further comprises an additive selected from surfactants, drift reduction agents, safeners, solubility enhancing agents, thickening agents, flow enhancers, foam-moderating agents, freeze protectants, UV protectants, preservatives, and/or antimicrobials. ### Claim 10 (depends on 9) The method of claim 9, wherein the herbicidal composition further comprises a drift reduction agent. ### Claim 11 (depends on 1) The method of claim 1, wherein the auxin herbicide comprises dicamba, or an agriculturally acceptable salt or ester thereof. ### Claim 12 (depends on 1) The method of claim 1, wherein the auxin herbicide comprises 2,4-D, or an agriculturally acceptable salt or ester thereof. ### Claim 13 (depends on 1) The method of claim 1, wherein the herbicidal composition further comprises an additive selected from surfactants, drift reduction agents, safeners, solubility enhancing agents, thickening agents, flow enhancers, foam-moderating agents, freeze protectants, UV protectants, preservatives, and/or antimicrobials. ### Claim 14 (depends on 13) The method of claim 13, wherein the herbicidal composition further comprises a drift reduction agent. ### Claim 15 A method for preparing an herbicidal composition, the method comprising: combining (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) a monocarboxylate, and (iii) water, wherein the auxin herbicide is selected from the group consisting of dicamba, or an agriculturally acceptable salt or ester thereof, 2,4-D, or an agriculturally acceptable salt or ester thereof, and mixtures thereof, and the monocarboxylate is selected from the group consisting of a formate salt, an acetate salt, a propionate salt, a benzoate salt, and combinations thereof, wherein said combining comprises: providing a liquid herbicidal composition concentrate comprising from about 120 to about 600 g a.e./L of auxin herbicide; adding the monocarboxylate to the herbicidal composition concentrate; and diluting the herbicidal composition concentrate comprising the auxin herbicide and monocarboxylate, with water, thereby forming an herbicidal composition comprising from about 0.1 g a.e./L to about 50 g a.e./L of auxin herbicide, wherein the herbicidal composition comprises an amount of the monocarboxylate sufficient to provide enhanced protection from off-target crop injury as compared to an otherwise identical herbicidal composition lacking the monocarboxylate while maintaining comparable herbicidal efficacy on auxin-susceptible plants located in the target area. ### Claim 16 (depends on 15) The method of claim 15, wherein the auxin herbicide comprises dicamba, or an agriculturally acceptable salt or ester thereof. ### Claim 17 (depends on 15) The method of claim 15, wherein the auxin herbicide comprises 2,4-D, or an agriculturally acceptable salt or ester thereof. ### Claim 18 (depends on 15) The method of claim 15, wherein the herbicidal composition further comprises an additive selected from surfactants, drift reduction agents, safeners, solubility enhancing agents, thickening agents, flow enhancers, foam-moderating agents, freeze protectants, UV protectants, preservatives, and/or antimicrobials. ### Claim 19 (depends on 18) The method of claim 18, wherein the herbicidal composition further comprises a drift reduction agent. ### Claim 20 (depends on 15) The method of claim 15, the method further comprising combining a non-auxin herbicide with the (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) an acetate salt, and (iii) water, wherein the non-auxin herbicide is selected from glyphosate, or an agriculturally acceptable salt thereof and glufosinate, or an agriculturally acceptable salt thereof. ### Claim 21 A method for preparing an herbicidal composition, the method comprising: combining (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) a monocarboxylic acid, (iii) a neutralizing base, and (iv) water, wherein the auxin herbicide is selected from the group consisting of dicamba, or an agriculturally acceptable salt or ester thereof, 2,4-D, or an agriculturally acceptable salt or ester thereof, and mixtures thereof, and the monocarboxylic acid is selected from the group consisting of formic acid, acetic acid, propionic acid, benzoic acid, and combinations thereof, wherein said combining comprises: providing a liquid herbicidal composition concentrate comprising from about 20 to about 600 g a.e./L of auxin herbicide; adding the monocarboxylic acid to the herbicidal composition concentrate comprising the auxin herbicide, followed by adding the neutralizing base to the herbicidal composition concentrate; and diluting the herbicidal composition concentrate, thereby forming an herbicidal composition comprising from about 0.1 g a.e./L to about 50 g a.e./L of auxin herbicide, wherein the herbicidal composition comprises an amount of the monocarboxylic acid sufficient to provide enhanced protection from off-target crop injury as compared to an otherwise identical herbicidal composition lacking the monocarboxylic acid while maintaining comparable herbicidal efficacy on auxin-susceptible plants located in the target area. ### Claim 22 (depends on 21) The method of claim 21, the method further comprising combining a non-auxin herbicide with the (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) a monocarboxylic acid, (iii) neutralizing base, and (v) water, wherein the non-auxin herbicide is selected from glyphosate, or an agriculturally acceptable salt thereof and glufosinate, or an agriculturally acceptable salt thereof. ### Claim 23 (depends on 22) The method of claim 22, wherein said combining comprises: adding the monocarboxylic acid to an herbicidal composition concentrate comprising the auxin herbicide and the non-auxin herbicide, followed by adding the neutralizing base to the herbicidal composition concentrate; and diluting the herbicidal composition concentrate. ### Claim 24 (depends on 22) The method of claim 22, wherein said combining comprises: adding the neutralizing base to an herbicidal composition concentrate comprising the auxin herbicide and the non-auxin herbicide, followed by adding the monocarboxylic acid to the herbicidal composition concentrate; and diluting the herbicidal composition. ### Claim 25 (depends on 22) The method of claim 22, wherein said combining comprises: diluting an herbicidal composition concentrate comprising the auxin herbicide and the non-auxin herbicide, with water; and adding the neutralizing base to the diluted concentrate, followed by adding the monocarboxylic acid to the diluted concentrate. ### Claim 26 (depends on 22) The method of claim 22, wherein said combining comprises: diluting an herbicidal composition concentrate comprising the auxin herbicide and the non-auxin herbicide, with water; and adding the monocarboxylic acid to the diluted concentrate, followed by addition of the neutralizing base to the diluted concentrate. ### Claim 27 (depends on 22) The method of claim 22, wherein said combining comprises: adding the monocarboxylic acid to an herbicidal composition concentrate comprising the auxin herbicide, followed by adding the neutralizing base to the herbicidal composition concentrate; adding the non-auxin herbicide to the herbicidal composition concentrate; and diluting the herbicidal composition concentrate. ### Claim 28 (depends on 22) The method of claim 22, wherein said combining comprises: adding the neutralizing base to an herbicidal composition concentrate comprising the auxin herbicide, followed by adding the monocarboxylic acid to the herbicidal composition concentrate; adding the non-auxin herbicide to the herbicidal composition concentrate; and diluting the herbicidal composition concentrate. ### Claim 29 (depends on 22) The method of claim 22, wherein said combining comprises: diluting the herbicidal composition concentrate comprising the auxin herbicide, with water; adding the neutralizing base to the diluted concentrate, followed by adding the monocarboxylic acid to the diluted concentrate; and adding the non-auxin herbicide to the diluted concentrate. ### Claim 30 (depends on 22) The method of claim 22, wherein said combining comprises: diluting the herbicidal composition concentrate comprising the auxin herbicide, with water; adding the monocarboxylic acid to the diluted concentrate, followed by addition of the neutralizing base to the diluted concentrate; and adding the non-auxin herbicide to the diluted concentrate. ### Claim 31 (depends on 21) The method of claim 21, wherein the neutralizing base in an alkali metal hydroxide selected from potassium hydroxide, sodium hydroxide, or a mixture thereof. ### Claim 32 (depends on 21) The method of claim 21, wherein the auxin herbicide is dicamba, or an agriculturally acceptable salt or ester thereof. ### Claim 33 (depends on 21) The method of claim 21, wherein the auxin herbicide is 2,4-D, or an agriculturally acceptable salt or ester thereof. ### Claim 34 (depends on 21) The method as set forth in claim 21, wherein the monocarboxylic acid is acetic acid. ### Claim 35 (depends on 21) The method of claim 21, wherein the herbicidal composition further comprises an additive selected from surfactants, drift reduction agents, safeners, solubility enhancing agents, thickening agents, flow enhancers, foam-moderating agents, freeze protectants, UV protectants, preservatives, and/or antimicrobials. ### Claim 36 (depends on 35) The method of claim 35, wherein the herbicidal composition further comprises a drift reduction agent. ### Claim 37 A method for preparing an herbicidal composition, the method comprising: combining (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) a monocarboxylic acid, (iii) a neutralizing base, and (iv) water, wherein the auxin herbicide is selected from the group consisting of dicamba, or an agriculturally acceptable salt or ester thereof, 2,4-D, or an agriculturally acceptable salt or ester thereof, and mixtures thereof, and the monocarboxylic acid is selected from the group consisting of formic acid, acetic acid, propionic acid, benzoic acid, and combinations thereof, wherein said combining comprises: providing a liquid herbicidal composition concentrate comprising from about 20 to about 600 g a.e./L of auxin herbicide; adding the neutralizing base to the herbicidal composition concentrate comprising the auxin herbicide, followed by adding the monocarboxylic acid to the herbicidal composition concentrate; and diluting the herbicidal composition concentrate, thereby forming an herbicidal composition comprising from about 0.1 g a.e./L to about 50 g a.e./L of auxin herbicide, wherein the herbicidal composition comprises an amount of the monocarboxylic acid sufficient to provide enhanced protection from off-target crop injury as compared to an otherwise identical herbicidal composition lacking the monocarboxylic acid while maintaining comparable herbicidal efficacy on auxin-susceptible plants located in the target area. ### Claim 38 (depends on 37) The method of claim 37, wherein the auxin herbicide comprises dicamba, or an agriculturally acceptable salt or ester thereof. ### Claim 39 (depends on 37) The method of claim 37, wherein the auxin herbicide comprises 2,4-D, or an agriculturally acceptable salt or ester thereof. ### Claim 40 (depends on 37) The method of claim 37, wherein the herbicidal composition further comprises an additive selected from surfactants, drift reduction agents, safeners, solubility enhancing agents, thickening agents, flow enhancers, foam-moderating agents, freeze protectants, UV protectants, preservatives, and/or antimicrobials. ### Claim 41 (depends on 40) The method of claim 40, wherein the herbicidal composition further comprises a drift reduction agent. ### Claim 42 (depends on 37) The method of claim 37, the method further comprising combining a non-auxin herbicide with the (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) a monocarboxylic acid, (iii) neutralizing base, and (v) water, wherein the non-auxin herbicide is selected from glyphosate, or an agriculturally acceptable salt thereof and glufosinate, or an agriculturally acceptable salt thereof. ### Claim 43 A method for preparing an herbicidal composition, the method comprising: combining (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) a monocarboxylic acid, (iii) a neutralizing base, and (iv) water, wherein the auxin herbicide is selected from the group consisting of dicamba, or an agriculturally acceptable salt or ester thereof, 2,4-D, or an agriculturally acceptable salt or ester thereof, and mixtures thereof, and the monocarboxylic acid is selected from the group consisting of formic acid, acetic acid, propionic acid, benzoic acid, and combinations thereof, wherein said combining comprises: providing a liquid herbicidal composition concentrate comprising from about 20 to about 600 g a.e./L of auxin herbicide; diluting the herbicidal composition concentrate comprising the auxin herbicide, with water, thereby forming an herbicidal composition comprising from about 0.1 g a.e./L to about 50 g a.e./L of auxin herbicide; and adding the neutralizing base to the herbicidal composition, followed by adding the monocarboxylic acid to the herbicidal composition, wherein the herbicidal composition comprises an amount of the monocarboxylic acid sufficient to provide enhanced protection from off-target crop injury as compared to an otherwise identical herbicidal composition lacking the monocarboxylic acid while maintaining comparable herbicidal efficacy on auxin-susceptible plants located in the target area. ### Claim 44 (depends on 43) The method of claim 43, wherein the auxin herbicide comprises dicamba, or an agriculturally acceptable salt or ester thereof. ### Claim 45 (depends on 43) The method of claim 43, wherein the auxin herbicide comprises 2,4-D, or an agriculturally acceptable salt or ester thereof. ### Claim 46 (depends on 43) The method of claim 43, wherein the herbicidal composition further comprises an additive selected from surfactants, drift reduction agents, safeners, solubility enhancing agents, thickening agents, flow enhancers, foam-moderating agents, freeze protectants, UV protectants, preservatives, and/or antimicrobials. ### Claim 47 (depends on 46) The method of claim 46, wherein the herbicidal composition further comprises a drift reduction agent. ### Claim 48 (depends on 43) The method of claim 43, the method further comprising combining a non-auxin herbicide with the (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) a monocarboxylic acid, (iii) neutralizing base, and (v) water, wherein the non-auxin herbicide is selected from glyphosate, or an agriculturally acceptable salt thereof and glufosinate, or an agriculturally acceptable salt thereof. ### Claim 49 A method for preparing an herbicidal composition, the method comprising: combining (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) a monocarboxylic acid, (iii) a neutralizing base, and (iv) water, wherein the auxin herbicide is selected from the group consisting of dicamba, or an agriculturally acceptable salt or ester thereof, 2,4-D, or an agriculturally acceptable salt or ester thereof, and mixtures thereof, and the monocarboxylic acid is selected from the group consisting of formic acid, acetic acid, propionic acid, benzoic acid, and combinations thereof, wherein said combining comprises: providing a liquid herbicidal composition concentrate comprising from about 20 to about 600 g a.e./L of auxin herbicide; diluting the herbicidal composition concentrate comprising the auxin herbicide, with water, thereby forming an herbicidal composition comprising from about 0.1 g a.e./L to about 50 g a.e./L of auxin herbicide; and adding the monocarboxylic acid to the herbicidal composition, followed by addition of the neutralizing base to the herbicidal composition, wherein the herbicidal composition comprises an amount of the monocarboxylic acid sufficient to provide enhanced protection from off-target crop injury as compared to an otherwise identical herbicidal composition lacking the monocarboxylic acid while maintaining comparable herbicidal efficacy on auxin-susceptible plants located in the target area. ### Claim 50 (depends on 49) The method of claim 49, wherein the auxin herbicide comprises dicamba, or an agriculturally acceptable salt or ester thereof. ### Claim 51 (depends on 49) The method of claim 49, wherein the auxin herbicide comprises 2,4-D, or an agriculturally acceptable salt or ester thereof. ### Claim 52 (depends on 49) The method of claim 49, wherein the herbicidal composition further comprises an additive selected from surfactants, drift reduction agents, safeners, solubility enhancing agents, thickening agents, flow enhancers, foam-moderating agents, freeze protectants, UV protectants, preservatives, and/or antimicrobials. ### Claim 53 (depends on 52) The method of claim 52, wherein the herbicidal composition further comprises a drift reduction agent. ### Claim 54 (depends on 49) The method of claim 49, the method further comprising combining a non-auxin herbicide with the (i) an auxin herbicide, or an agriculturally acceptable salt or ester thereof, (ii) a monocarboxylic acid, (iii) neutralizing base, and (v) water, wherein the non-auxin herbicide is selected from glyphosate, or an agriculturally acceptable salt thereof and glufosinate, or an agriculturally acceptable salt thereof.