US010212933B2 (12 ) United States Patent (10 ) Patent No. : US 10 ,212 , 933 B2 Hemminghaus et al. ( 45 ) Date of Patent : * Feb . 26 , 2019

( 54 ) LOW VOLATILITY HERBICIDAL 8 ,987 , 167 B2 3 / 2015 Xu et al. 2002/ 0108415 A1 8 / 2002 Volgas et al . COMPOSITIONS 2002/ 0160916 Al 10 / 2002 Volgas et al. 2006 /0270557 A1 11 /2006 Volgas et al . (71 ) Applicant: Monsanto Technology LLC , St. Louis , 2010 /0248963 AL 9 /2010 Becher et al. MO (US ) 2010 / 0331182 Al 12 /2010 Zhang et al. 2011 / 0009269 Al 1 / 2011 Gioia et al. (72 ) Inventors : John W . Hemminghaus, St. Louis , MO 2011 /0034332 A1 2 / 2011 Becher et al. 2011/ 0166235 A1 7 / 2011 Sun (US ) ; Alison MacInnes , St. Louis , MO 2012 / 0142532 Al 6 / 2012 Wright et al . (US ) ; Daniel R . Wright, St. Louis , MO 2012 /0231956 A1 9 / 2012 Rainbird (US ); Junhua Zhang , St. Louis , MO 2012 / 0238451 Al 9 /2012 Feng et al . (US ) 2012 / 0289402 A1 11/ 2012 Brown et al . 2013 /0079228 A1 3 / 2013 Freed Subject to any disclaimer, the term of this 2013 /0109572 A1 5 / 2013 Pernak et al . ( * ) Notice : 2013 /0109725 A1 5 / 2013 Dave et al . patent is extended or adjusted under 35 2013 / 0225405 Al 8 / 2013 Hixson et al . U . S .C . 154 (b ) by 0 days . 2014 / 0013654 A1 1 / 2014 Burke This patent is subject to a terminal dis 2015 / 0057157 Al 2 / 2015 Baseeth et al . claimer . FOREIGN PATENT DOCUMENTS (21 ) Appl. No .: 15 /653 , 772 CN 1176954 A 3 / 1998 CN 101564044 A 10 / 2009 (22 ) Filed : Jul. 19 , 2017 CN 103371160 A 10 / 2013 WO 9007275 7 / 1990 WO 1992012637 8 / 1992 (65 ) Prior Publication Data WO 9410844 5 / 1994 US 2017 /0311593 A1 Nov. 2 , 2017 WO 2000041567 7 / 2000 WO 0126463 4 / 2001 wo 2002011536 2 / 2002 Related U . S . Application Data WO 02069718 9 / 2002 (63 ) Continuation of application No. 14 /440 , 789, filed as WO 2004080177 9 / 2004 application No . PCT/ US2013 /068507 on Nov . 5 , WO 2008077196 7 /2008 2013 , now Pat. No . 9 ,743 ,664 . (Continued ) (60 ) Provisional application No . 61 /794 , 769 , filed on Mar . OTHER PUBLICATIONS 15 , 2013 , provisional application No . 61 /722 , 700 , AGRI STAR® Diacamba DMA Salt Label and Material Safety Data filed on Nov . 5 , 2012 . Sheet , Aug . 2012 , Albaugh , Inc. , Ankeny, Iowa, found at http :/ / (51 ) Int. CI. www .cdms . net / labelsmsds/ LMDefault. aspx ? pd = 4887 & t. (36 pages ) . AOIN 37 /02 BANVEL® Herbicide Label and Material Safety Data Sheet, 1999 , ( 2006 .01 ) Arysta LifeScience North America , LLC , Cary , North Carolina , AOIN 37/ 04 ( 2006 . 01 ) found at http : // www . cdms. net / labelsmsds/ LMDefault . aspx ? pd = 92 A01N 37/ 40 ( 2006 .01 ) & t. ( 29 pages ). AOIN 39 /04 ( 2006 .01 ) BARRAGE HF? Label, 2005 , Helena Chemical Company , Col AOIN 57/ 20 ( 2006 .01 ) lierville , Tennessee , Label found at http :/ /www .helenachemical . com / GO9B 19 / 00 ( 2006 .01 ) specialty /Labels /Barrage % 20HF % 20 ( 5905 - 529 ) .pdf . ( 12 pages) . (52 ) U .S . CI. CLARITY® Herbicide Label, 2010, BASF Corporation , Research CPC ...... A01N 37 /04 (2013 . 01 ); AOIN 37 /02 Triangle Park , North Carolina , found at http : / /www . cdms.net / LDat / Id797012 .pdf . ( 22 pages ) . (2013 .01 ) ; AOIN 37/ 40 ( 2013 .01 ); AOIN DIABLO® Herbicide Label , 2011, Nufarm Americas Inc . , Burr 39 /04 (2013 . 01 ) ; AOIN 57 / 20 ( 2013 .01 ) ; Ridge , Illinois , found at http : // www . cdms.net /labelsmsds / LMDefault . G09B 19 /00 (2013 .01 ) aspx ? pd = 7398 & t. (30 pages) . (58 ) Field of Classification Search None (Continued ) See application file for complete search history . Primary Examiner — Alton N Pryor (74 ) Attorney , Agent, or Firm — Stinson Leonard Street ( 56 ) References Cited LLP ; Erin C . Robert U . S . PATENT DOCUMENTS (57 ) ABSTRACT 5 , 035 , 738 A 7 / 1991 Burns et al . 5 , 389 , 598 A 2 / 1995 Berk et al. The present invention relates generally low volatility herbi 5 , 703 , 014 A 12 / 1997 Caulder et al . cidal compositions comprising at least one auxin herbicide 5 ,877 , 112 A 3 / 1999 Roberts et al . and at least one monocarboxylic acid , or monocarboxylate 6 , 200 , 929 B1 3 / 2001 Horibe et al . thereof. The invention further relates generally to methods 6 , 541 , 424 B2 4 / 2003 Roberts et al. for preparing and using such low volatility herbicidal com 6 , 831, 038 B2 12 / 2004 Volgas et al . 6 , 906 ,004 B26 / 2005 Parrish et al. positions, including methods for controlling auxin - suscep 7 ,012 , 040 B2 3 / 2006 Hacker et al. tible plant growth on agricultural and non -agricultural lands . 8 , 268 ,749 B2 9 / 2012 Wright et al. 8 , 337 , 900 B2 12 / 2012 CasanGiner et al . 45 Claims, No Drawings US 10 ,212 ,933 B2 Page 2

References Cited ORACLE® Dicamba Agricultural Herbicide Label, 2010 , Gharda ( 56 ) Chemicals Limited , Newtown, Pennsylvania , found at http :/ / www . kellysolutions. com /ok /showproductinfo .asp ? Product _ Name= Oracle + FOREIGN PATENT DOCUMENTS Dicamba + Agricultural + Herbicide & EPA _ Id = 33658 - 30 . (33 pages ) . WO 2010053385 5 / 2010 ROUNDUP POWERMAX® Herbicide Label, 2010 , Monsanto WO 2013159731 10 / 2013 Company , St. Louis , Missouri , found at http : / /www . cdms.net / labelsmsds/ LMDefault .aspx ? pd = 8837 & t . ( 54 pages ) . ROUNDUP WEATHERMAX® Herbicide Label , 2007 , Monsanto OTHER PUBLICATIONS Company , St. Louis , Missouri, found at http : // www . cdms.net / DISTINCT® Herbicide Label , Mar . 2012 , BASF Corporation , labelsmsds/ LMDefault .aspx ? pd = 6026 & t. (49 pages) . Research Triangle Park , North Carolina , found at http : // www . cdms. Strachan et al. , “ Vapor Movement of Synthetic Auxin Herbicides : net / labelsmsds/ LMDefault . aspx ? pd = 3700 & t. (21 pages) . Aminocyclopyrachlor, Aminocyclopyrachlor -Methyl Ester , Dicamba, DURANGO® DMA® Herbicide Label, Jun . 2012 , Dow AgroSci and Aminopyralid ” Weed Science, 58 :103 - 108 (2010 ). ences LLC , Indianapolis , Indiana , found at http :/ / www . cdms.net / TOUCHDOWN PRO® Herbicide Label, 2010 , Sygenta Crop Pro labelsmsds/ LMDefault . aspx ? pd = 8831 & t_ ( 36 pages ). tection , Inc ., Greensboro , North Carolina , found at http : / /www .cdms . FORMULA 40® Herbicide Label with EPA Re -Registration Approval dated Sep . 16 , 2008 , Dow AgroSciences, LLC , Indianapolis , Indi net / labelsmsds/ LMDefault .aspx ?pd = 4875 & t. (29 pages) . ana , Label found at http : / /www .cdms . net / labelsmsds/ LMDefault . TRAXION® Herbicide Label , 2011 , Syngenta Crop Protection , aspx ? pd = 8600 & t , and EPA Letter found at http : / / iaspub . epa . gov / Inc . , Greensboro , North Carolina , found at http : / /www . apex / pesticides / f ? p = PPLS : 102 :: :NO :: P102 _ REG _NUM :62719 - 1 . (45 syngentacropprotection . com / labels/ default .aspx . (64 pages ) . pages ) . VANQUISH® Herbicide Label , 2011 , Sygenta Crop Protection , HONCHO PLUS® Herbicide Label, 2010 , Monsanto Company, St. Inc ., Greensboro , North Carolina , found at http : / /tirmsdev .com Louis , Missouri, found at http :/ / www .cdms . net/ labelsmsds/ LMDefault . Syngenta - Professional- Products - Vanquish -Herbicide -p90 . ( 8 pages) . aspx ? pd = 6296 & t. ( 26 pages) . VISION® Herbicide Label, Jul. 25 , 2012 , Helena Chemical Com International Search Report and Written Opinion for International pany, Collierville , Tennessee , found at http :/ / www .cdms . net / Application No . PCT/ US2013 /068507 dated May 12 , 2014 ( 15 pages ) . LabelsMsds/ LMDefault. aspx ? pd = 9280 & t. ( 25 pages ). LIBERTY® 280 SL Herbicide Label , 2011 , Bayer CropScience , WEEDER 64® Broadleaf Herbicide Label with EPA Re Research Triangle Park , North Carolina , found at http : // fs1. agrian . Registration Approval dated Sep . 8 , 2010 , Nufarms Americas Inc . , com / pdfs /Liberty _ 280 _ SL _ Label2 .pdf . ( 21 pages ) . Burr Ridge , Illinois , Label found at http : // www .afpmb . org/ sites / OPTI -AMINE® 2, 4 -D Amine Herbicide Label, Apr. 2012 , Helena default/ files /pubs / standardlists /labels / 6840 -00 - 577 -4194 _ label. pdf, EPA Chemical Company, Collierville , Tennessee , found at http :/ / www . Letter found at http :/ / iaspub . epa . gov / apex / pesticides/ f? p = cdms. net / labelsmsds/ LMDefault .aspx ?pd = 4410 & t . (25 pages) . PPLS : 102: : :NO :P102 _ REG _ NUM :71368 - 1 . (37 pages ) . US 10 , 212 , 933 B2 LOW VOLATILITY HERBICIDAL least one monocarboxylic acid , or agriculturally acceptable COMPOSITIONS monocarboxylate thereof; and , optionally , a non - auxin her bicide; wherein the compositions exhibit reduced volatility CROSS -REFERENCE TO RELATED relative to an otherwise identical composition lacking the APPLICATIONS 5 monocarboxylic acid or monocarboxylate thereof . In one embodiment, the auxin herbicide is selected from dicamba , This is a continuation of U . S . application Ser . No . 14 /440 , or a agriculturally acceptable salt or ester thereof, and 2 ,4 - D , 789 , filed May 5 , 2015 , which is a U .S . national stage or an agriculturally acceptable salt of ester thereof. In one application of International Patent Application No . PCT embodiment, the composition comprises an acetate salt . In US2013 / 068507 , filed Nov . 5 , 2013 , which claims priority to 10 another embodiment, the non - auxin herbicide is glyphosate , U . S . Provisional Application Ser. No . 61/ 794 ,769 filed on or an agriculturally acceptable salt thereof. Mar. 15 . 2013 and U . S . Provisional Application Ser. No. In another aspect , the invention provides a herbicidal 61/ 722 ,700 filed on Nov . 5 , 2012 , the entire disclosures of adjuvant composition comprising a monocarboxylic acid , or which are incorporated herein by reference . monocarboxylate thereof, and , optionally , an alkali metal 15 phosphate , that can serve as the source of monocarboxylic FIELD OF THE INVENTION acid , or a monocarboxylate thereof, used in the preparation of the herbicidal compositions of the present invention . The present invention relates generally to low volatility In another aspect, the invention provides methods of herbicidal compositions comprising at least one auxin her - reducing the volatility of an auxin herbicide , wherein the bicide and at least one monocarboxylic acid , or monocar - 20 methods comprise the step of contacting an auxin herbicide boxylate thereof. The invention further relates generally to with a volatility - lowering effective amount of a monocar methods for preparing and using such low volatility herbi- boxylic acid , or a monocarboxylate thereof, thereby reduc cidal compositions , including methods for controlling auxin - ing the volatility of the auxin herbicide . susceptible plant growth on agricultural and non -agricultural In another aspect, the invention provides methods of lands. 25 controlling the growth of auxin - susceptible plants , wherein the methods comprise applying to the auxin - susceptible BACKGROUND OF THE INVENTION plants a herbicidal composition application mixture com prising at least one auxin herbicide; at least one monocar Auxin herbicides, such as dicamba ( 3 , 6 -dichloro - 2 - boxylic acid , or monocarboxylate thereof; and , optionally , a methoxybenzoic acid ) and 2 , 4 - D ( 2 , 4 - dichlorophenoxy - 30 non - auxin herbicide ; wherein the application mixture exhib acetic acid ), are commonly used to control auxin -susceptible its reduced auxin herbicide volatility relative to an otherwise plant growth on both agricultural and non -agricultural lands . identical application mixture lacking the monocarboxylic Volatility and drift , however, are problems frequently asso - acid , or monocarboxylate thereof. ciated with these herbicides . Volatile auxin herbicides can , In another aspect , the invention provides methods of under certain application conditions, vaporize into the sur - 35 controlling off - site movement of an auxin herbicide , rounding atmosphere and migrate from the application site wherein the methods comprise contacting the auxin herbi to adjacent crop plants , such as soybeans and cotton , where cide with a volatility - lowering effective amount of a mono contact damage to sensitive plants can occur. Spray drift can carboxylic acid , or a monocarboxylate thereof , prior to be attributed to both volatility and the physical movement of application of the auxin herbicide . small particles from the target site to adjacent crop plants . 40 In another aspect, the invention provides methods of Prior approaches to reducing herbicide volatility have counseling an individual regarding the preparation and /or included efforts to identify herbicide salts and formulations application of an auxin herbicide . exhibiting lower volatility. As one example , the digly . Further benefits of the present invention will be apparent colamine salt of dicamba exhibits a lower volatility than the to one skilled in the art from reading this patent application . dimethylamine salt of dicamba . Although lower volatility 45 The embodiments of the invention described in the follow auxin herbicide salts and formulations have been reported , ing paragraphs are intended to illustrate the invention and further reduction in the volatility and off - target movement of should not be deemed to narrow the scope of the invention . auxin herbicides is still desirable . Another approach to reducing auxin herbicide volatility DETAILED DESCRIPTION OF THE has focused on encapsulation , for example , absorbing the 50 INVENTION auxin herbicide into solid phase natural or synthetic poly mer , ormicroencapsulating the auxin herbicide in a polymer The present invention provides herbicidal compositions shell . Due to technological challenges and other factors , comprising an auxin herbicide wherein the compositions however , commercial encapsulation products that satisfac - exhibit reduced volatility and /or vapor drift upon application torily reduce auxin herbicide volatility have not been devel - 55 with respect to the auxin herbicide. Specifically, the com oped . positions comprise , in addition to the auxin herbicide , at Accordingly , auxin herbicide compositions having least one monocarboxylic acid , or monocarboxylate thereof, reduced volatility relative to currently available composi in an amount sufficient to reduce the volatility of the auxin tions would be desirable , particularly reduced - volatility herbicide relative to an otherwise identical composition compositions that exhibit no significant reduction in herbi- 60 lacking the monocarboxylic acid , or monocarboxylate cidal effectiveness relative to currently available composi - thereof. tions . It has been discovered that the addition of a sufficient amount of a monocarboxylic acid , or a monocarboxylate BRIEF DESCRIPTION OF THE INVENTION thereof (particularly a non -ammoniated monocarboxylate 65 salt ) , to a herbicidal composition concentrate ( e . g . , a “ pre In one aspect , the present invention provides herbicidal mix ” ) or a herbicidal composition application mixture ( e . g . , compositions comprising at least one auxin herbicide ; at a “ tank mix ” ) results in a significant reduction in the level of US 10 , 212 , 933 B2 volatile auxin herbicide detected . For some compositions, salt is selected from the group consisting of N , N - bis - [ amino the amount of volatile auxin herbicide present is actually propyl] methylamine , monoethanolamine , dimethylamine, below the detection level of sophisticated analytical methods isopropylamine, diglycolamine , potassium , and sodium such as liquid chromatography -mass spectrometry (LC ) salts , and combinations thereof. MS) . As compared to auxin compositions known in the art, 5 Throughout the remainder of the description of the inven it is believed that the compositions of the present invention tion , where reference is made to dicamba , or an agricultur provide enhanced protection from off - target crop injury ally acceptable salt or ester thereof, one skilled in the art will while maintaining comparable herbicidal efficacy on auxin understand that the principles of the present invention apply susceptible plants located in the target area . to auxin herbicides generally , including those described The present invention is additionally directed to methods 10 above, and that the present invention is not limited to for controlling the growth of auxin - susceptible plants , com herbicidal compositions containing dicamba , or an agricul prising applying the herbicidal compositions of the present turally acceptable salt or ester thereof. invention to such plants in accordance with the guidance In another embodiment, the herbicidal composition com provided below . prises 2 , 4 - D , or an agriculturally acceptable salt or ester As used throughout this application , the term “ agricultur- 15 thereof. Examples of suitable 2 , 4 - D salts include the cho ally acceptable salt ” refers to a salt comprising a cation that line , dimethylamine , and isopropylamine salts , and combi is known and accepted in the art for the formation of salts for nations thereof. Examples of suitable 2 , 4 - D esters include agricultural or horticultural use . In one embodiment, the salt the methyl, ethyl, propyl, butyl ( 2 , 4 -DB ) , and isooctyl is a water - soluble salt . esters, and combinations thereof. Commercially available 20 sources of 2 , 4 - D , and its agriculturally acceptable salts and A . AUXIN HERBICIDE COMPONENT esters , include those products sold under the trade names BARRAGE? , FORMULA 40® , OPT- AMINE® , and WEE The term “ auxin herbicide” refers to a herbicide that DAR 64® . functions as a mimic of an auxin plant growth hormone , In another embodiment, the herbicidal composition com thereby affecting plant growth regulation . Examples of 25 prises an agriculturally acceptable 2 ,4 - D salt, wherein the auxin herbicides that are suitable for use in the herbicidal salt is selected from the group consisting of choline , dim compositions of the present invention include, without limi- ethylamine , and isopropylamine salts , and combinations tation , benzoic acid herbicides , phenoxy herbicides , pyridine thereof . carboxylic acid herbicides , pyridine oxy herbicides, pyrimi- In another embodiment, the herbicidal composition com dine carboxy herbicides , quinoline carboxylic acid herbi- 30 prises an agriculturally acceptable 2 ,4 - D ester , wherein the cides, and benzothiazole herbicides. ester is selected from the group consisting of butyl ( i . e . , Specific examples of auxin herbicides include : 2 , 4 - DB ) and isooctyl esters , and combinations thereof. Dicamba ( 3 ,6 - dichloro - 2 -methoxy benzoic acid ) ; In another embodiment, the herbicidal composition com 2 ,4 - D (2 ,4 -dichlorophenoxyacetic acid ); prises at least two auxin herbicides , for example , dicamba , 2, 4 -DB ( 4 -( 2, 4 -dichlorophenoxy )butanoic acid ) ; 35 or an agriculturally acceptable salt or ester thereof , and Dichloroprop ( 2 - ( 2 , 4 - dichlorophenoxy ) propanoic acid ) ; 2 , 4 - D , or an agriculturally acceptable salt or ester thereof. MCPA ( (4 - chloro -2 -methylphenoxy ) acetic acid ); In another embodiment, the herbicidal composition com MCPB ( 4 -( 4 - chloro -2 -methylphenoxy )butanoic acid ); prises an agriculturally acceptable auxin herbicide salt ( such Aminopyralid (4 -amino - 3 ,6 -dichloro - 2- pyridinecarboxylic as a dicamba salt, a 2 ,4 - D salt, and/ or a 2, 4 -DB salt ) that is acid ); 40 an ionic liquid as described in published application Clopyralid ( 3 , 6 - dichloro - 2 - pyridinecarboxylic acid ) ; US2013 /0109572 , i . e ., a salt that is a liquid at a temperature Fluoroxypyr ([ ( 4 - amino -3 ,5 -dichloro - 6 - fluoro - 2- pyridinyl ) at or below about 150° C . The entire text of US2013 / oxy ]acetic acid ); 0109572 is incorporated by reference into this application . Triclopyr ([ ( 3 , 5 ,6 -trichloro - 2 - pyridinyl) oxy ] acetic acid ) ; Diclopyr ; 45 B . MONOCARBOXYLIC Mecoprop (2 - (4 -chloro - 2 -methylphenoxy )propanoic ic acid ): ; ACID /MONOCARBOXYLATE COMPONENT Mecoprop - P ; Picloram ( 4 - amino - 3 ,5 , 6 - trichloro - 2 -pyridinecarboxylic “ Monocarboxylic acid ” refers to a hydrocarbon or sub acid ); stituted hydrocarbon containing only one carboxy functional Quinclorac ( 3 , 7 -dichloro - 8 - quinolinecarboxylic acid ) ; and 50 group ( i. e ., R ? _ C ( O )OH ) . “ Monocarboxylate ” refers to a Aminocyclopyrachlor ( 6 - am ino - 5 - chloro - 2 - cyclopropyl - 4 - salt ( i. e ., R C ( O ) OM wherein M is an agriculturally pyrimidinecarboxylic acid ) ; acceptable cation ) or ester ( i. e . ,R1 _ C (O )OR ? wherein R² is including salts and esters thereof; racemic mixtures and hydrocarbon or substituted hydrocarbon ) of a monocarbox resolved isomers thereof; and combinations thereof. ylic acid . In one embodiment, the composition comprises at In one embodiment, the herbicidal composition comprises 55 least one monocarboxylate salt, which in aqueous compo dicamba, or an agriculturally acceptable salt or ester thereof. sitions may be present, in whole or in part, in dissociated Examples of suitable dicamba salts include the N , N - bis - form as a monocarboxylate anion and the corresponding [ aminopropyl] methylamine , monoethanolamine, dimethyl- cation . amine ( e . g . , BANVEL® , ORACLE® , etc .) , isopropylam Representative monocarboxylic acids and monocarboxy ine , diglycolamine ( e . g ., CLARITY® , VANQUISH® , etc .) , 60 lates generally comprise a hydrocarbon or unsubstituted potassium , and sodium salts , and combinations thereof . hydrocarbon selected from , for example , unsubstituted or Commercially available sources of dicamba , and its agri substituted , straight or branched chain alkyl ( e. g . , C1- C20 culturally acceptable salts , include those products sold under alkyl such as methyl, ethyl, n -propyl , isopropyl, etc .) ; the trade names BANVEL® , CLARITY® , DIABLO® , unsubstituted or substituted , straight or branched chain DISTINCT, ORACLE® , VANQUISH® , and VISION® . 65 alkenyl ( e. g ., C2 -C20 alkyl such as ethenyl , n - propenyl , In another embodiment, the herbicidal composition com - isopropenyl , etc . ) ; unsubstituted or substituted aryl ( e. g . , prises an agriculturally acceptable dicamba salt, wherein the phenyl , hydroxyphenyl, etc . ) ; or unsubstituted or substituted US 10 , 212 , 933 B2 arylalkyl ( e . g . , benzyl) . In one embodiment , the monocar - bicide having a primary mode of action other than as an boxylic acid is selected from the group consisting of formic auxin herbicide . Representative examples of non - auxin her acid , acetic acid , propionic acid , and benzoic acid . In bicides include acetyl CoA carboxylase (ACCase ) inhibi another embodiment, the monocarboxylate salt is selected tors , acetolactate synthase (ALS ) inhibitors, acetohydroxy from the group consisting of formate salts , acetate salts , 5 acid synthase ( AHAS ) inhibitors , photosystem II inhibitors , propionate salts , and benzoate salts . photosystem I inhibitors , protoporphyrinogen oxidase (PPO In one embodiment, the herbicidal composition comprises or Protox ) inhibitors, carotenoid biosynthesis inhibitors, a monocarboxylate salt having the formula Ri - C (O )OM , enolpyruvyl shikimate - 3 -phosphate (EPSP ) synthase inhibi wherein Rl is unsubstituted or substituted C . - C , alkyl and tor, glutamine synthetase inhibitor, dihydropteroate syn Mis a non - ammoniated , agriculturally acceptable cation . In 10 thetase inhibitor, mitosis inhibitors , and nucleic acid inhibi another embodiment, the herbicidal composition comprises tors ; salts and esters thereof; racemic mixtures and resolved a monocarboxylate salt having the formula R ? = C ( O ) OM , isomers thereof ; and combinations thereof. wherein R is unsubstituted C , -Co alkyl and M is an alkali Representative examples of ACCase inhibitors include metal salt . In another embodiment, the herbicidal composi- clethodim , clodinafop , fenoxaprop - P , fluazifop - P , quizalo tion comprises a monocarboxylate salt having the formula 15 top - P , and sethoxydim . R C ( O )OM , wherein Rl is unsubstituted C - C , alkyl and Representative examples of ALS or AHAS inhibitors M is an alkali metal salt selected from sodium and potas- inchuinclude flumetsulam , imazamethabenz - m , imazamox , sium . In another embodiment, the monocarboxylate salt is imazapic , imazapyr, imazaquin , imazethapyr, metsulfuron , potassium acetate . In another embodiment , the monocar prosulfuron , and sulfosulfuron . 20 Representative examples of photosystem I inhibitors boxylate salt is sodium acetate . include diquat and paraquat. C . ALKALI METAL PHOSPHATE / ALKALI Representative examples of photosystem II inhibitors METAL CARBONATE include atrazine , cyanazine, diuron , and metibuzin . Representative examples of PPO inhibitors include acif The herbicidal compositions of the present invention 25 luorofen , butafenacil, carfentrazone -ethyl , flufenpyr- ethyl , optionally may further comprise an alkali metal phosphate fluthiacet, flumiclorac , flumioxazin , fomesafen , lactofen , such as dipotassium phosphate . Dipotassium phosphate , for oxadiazon , oxyfluorofen , and sulfentrazone . example , can provide additional buffering and / or water - Representative examples of carotenoid biosynthesis conditioning for aqueous herbicidal compositions of the inhibitors include aclonifen , amitrole , diflufenican , mesotri present invention . Dipotassium phosphate is particularly 30 one , and sulcotrione . effective as a replacement for ammonium sulfate in herbi- A representative example of an EPSP inhibitor is cidal composition application mixtures prepared using hard N -phosphonomethyl glycine (glyphosate ) . water. A representative example of a glutamine synthetase Similarly , the herbicidal compositions of the present inhibitor is glufosinate . invention optionally may further comprise an alkali metal 35 A representative example of a dihydropteroate synthetase carbonate , such as potassium carbonate , to provide addi tional buffering and / or water -conditioning for aqueous her Representative examples of mitosis inhibitors include bicidal compositions of the present invention . acetochlor, alachlor, dithiopyr , S -metolachlor , and thiazopyr. In some embodiments , the herbicidal compositions of the Representative examples of nucleic acid inhibitors present invention comprise an alkali metal phosphate . In 40 include difenzoquat, fosamine , metham , and pelargonic other embodiments, the herbicidal compositions comprise acid . an alkali metal carbonate . In still other embodiments , the In one embodiment, the herbicidal compositions of the herbicidal compositions comprise an alkali metal phosphate present invention further comprise a non - auxin herbicide and an alkali metal carbonate . selected from the group consisting of acetochlor, glyphosate , 45 glufosinate , flumioxazin , fomesafen , and agriculturally acceptable salts thereof. D . NON -HERBICIDE ADDITIVES In one embodiment, the herbicidal compositions of the The herbicidal compositions of the present invention present invention further comprise glyphosate , or an agri optionally may further comprise conventional additives such culturally acceptable salt thereof. Suitable glyphosate salts as surfactants , drift reduction agents , safeners , solubility 50 include, for example , the ammonium , diammonium , dim enhancing agents , thickening agents, flow enhancers , foam - ethylammonium , monoethanolamine , isopropylamine , and moderating agents , freeze protectants , UV protectants , pre potassium salts , and combinations thereof. In one embodi servatives , antimicrobials , and / or other additives that are ment, the glyphosate salts are selected from the group necessary or desirable to improve the performance , crop consisting of monoethanolamine , isopropylamine , and safety , or handling of the composition . 55 potassium salts , and combinations thereof. In one embodiment, the herbicidal composition comprises In one embodiment, the herbicidal compositions of the less than about 10 ppm of ammonium sulfate . In another present invention further comprise glufosinate , or an agri embodiment, the herbicidal composition does not comprise culturally acceptable salt thereof. ammonium sulfate . In one embodiment, the herbicidal compositions of the In one embodiment, the herbicidal composition does not 60 present invention comprise dicamba , or an agriculturally comprise an acid other than a monocarboxylic acid . acceptable salt or ester thereof, and glyphosate , or an agriculturally acceptable salt thereof. In another embodi E . NON - AUXIN HERBICIDE COMPONENTS ment, the herbicidal compositions of the present invention comprise dicamba , or an agriculturally acceptable salt The herbicidal compositions of the present invention 65 thereof; glyphosate , or an agriculturally acceptable salt optionally may further comprise at least one non -auxin thereof; and a non -ammoniated , agriculturally acceptable herbicide. The term “ non - auxin herbicide ” refers to a her- acetate salt . Commercially available sources of glyphosate , US 10 , 212 , 933 B2 and its agriculturally acceptable salts , include those products about 80 % by weight of the concentrate . In another aspect , sold under the trade names DURANGO® DMA® , HON the amount is from about60 % to about 75 % by weight of the CHO PLUS® , ROUNDUP POWERMAX? , ROUNDUP concentrate . In another aspect, the amount is from about WEATHERMAX® , TRAXION® , and TOUCHDOWN? . 65 % to about 70 % by weight of the concentrate . In one embodiment, the herbicidal compositions of the 5 Ready - to -use herbicidal compositions and other herbi present invention comprise 2 , 4 - D , or an agriculturally cidal compositions of the present invention requiring no acceptable salt or ester thereof, and glyphosate , or an further processing prior to application ( e . g . , diluted concen agriculturally acceptable salt thereof. In another embodi- trates, tank mixes , etc . ) typically will comprise on an acid ment, the herbicidal compositions of the present invention equivalent basis ( a . e . ) from about 0 . 1 g a . e. / L to about 50 g comprise 2 ,4 - D , or an agriculturally acceptable salt or ester 10 a . e . / L total herbicide loading . Additional examples of rep thereof; glyphosate , or an agriculturally acceptable salt resentative total herbicide loading for such compositions thereof; and a non - ammoniated , agriculturally acceptable include about 0 . 5 , 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 15 , 20 , 25 , 30 , acetate salt . 35 , 40 , 45 , and 50 g a . e ./ L , and ranges thereof ( e . g . , from In another embodiment, the herbicidal composition com about 0 . 5 to about 5 g a . e . / L , from about 5 to about 10 g prises an agriculturally acceptable non - auxin herbicide salt 15 a . e ./ L , from about 10 to about 15 g a . e . / L , from about 15 to ( such as a glyphosate salt ) that is an ionic liquid as described about 20 g a . e . / L , from about 20 to about 25 g a . e ./ L , from in published application US2013/ 0109572 , i. e . , a salt that is about 25 to about 30 g a . e . / L from about 30 to about 35 g a liquid at a temperature at or below about 150° C . a .e ./ L , from about 35 to about 40 g a . e ./ L , from about 40 to about 45 g a . e . / L , from about 45 to about 50 g a . e . / L total F . COMPONENT LOADING 20 herbicide loading ) . In herbicidal compositions of the present invention com Suitable amounts , concentrations, and /or molar ratios of prising an auxin herbicide and a non - auxin herbicide , the the auxin herbicide , monocarboxylic acid , or monocarboxy - weight ratio on an acid equivalent basis of the auxin herbi late thereof , and optional non -auxin herbicide and non - cide to the non - auxin herbicide is typically no greater than herbicide additive components of the herbicidal composi- 25 about 50 : 1, for example , about 50 : 1 , 25 : 1 , 10 : 1 , 5 : 1 , 3 : 1 , 2 : 1 , tions of the present invention will depend to some extent 1 : 1 , 1 : 2 , 1 : 3 , 1 : 5 , about 1 : 10 , or ranges thereof such as from upon whether the composition is a ready - to -use composi about 50 : 1 to about 1 : 10 , from about 50 : 1 to about 1 : 5 , from tion , a concentrate to be diluted with water prior to appli - about 50 : 1 to about 1: 1 , from about 50 : 1 to about 3 : 1 , from cation ( e . g ., a " premix ” ), or a herbicidal composition pre - about 50 : 1 to about 5 : 1 , from about 50 : 1 to about 10 : 1, from pared by combining two or more herbicide components , 30 about 25 : 1 to about 1 : 1 , or from about 25 : 1 to about 3 : 1 . water , and , optionally , other non -herbicide components For any given auxin herbicide , one skilled in the art can ( e . g ., a " tank mix ” ) . readily determine using routine experimentation a minimum 1 . Herbicide Loading : concentration of auxin herbicide and a minimum ratio of Concentrated herbicidal compositions of the present auxin herbicide to any additional auxin herbicides and /or invention typically comprise on an acid equivalent basis 35 non - auxin herbicides contained in the herbicidal composi ( a . e . ) , for example, from about 120 to about 600 g a . e . / L , tion that is desirable for the intended application . from about 300 to about 600 g a . e . / L , from about 350 to 2 . Monocarboxylic Acid /Monocarboxylate Loading : about 600 g a . e . / L , from about 400 to about 600 g a . e . / L , As previously noted , it has been discovered that the from about 450 to about 600 g a . e ./ L , or from about 500 to concentration of volatilized auxin herbicide in the vapor about 600 g a . e ./ L total herbicide loading. Additional 40 phase surrounding a herbicidal composition comprising an examples of representative total herbicide loading include auxin herbicide and a monocarboxylic acid , or monocar about 120 , 150 , 200 , 250 , 300 , 350 , 400 , 450 , 500 , 550 , and boxylate thereof, is less than the concentration of volatilized 600 g a . e ./ L , and ranges thereof ( i. e ., from about 120 to auxin herbicide in the vapor phase surrounding a reference about 150 g a . e . / L , from about 150 to about 200 g a . e . / L , composition lacking the monocarboxylic acid or monocar from about 200 to about 250 g a . e ./ L , from about 250 to 45 boxylate , but otherwise having the same composition . In about 300 g a . e ./ L , from about 300 to about 350 g a . e. / L , various embodiments , the concentration of volatilized auxin from about 350 to about 400 g a . e ./ L from about 400 to about herbicide in the vapor phase surrounding a herbicidal com 450 g a . e. / L , from about 450 to about 500 g a .e ./ L , from position comprising an auxin herbicide and a monocarbox about 500 to about 550 g a . e . / L , from about 550 to about 600 ylic acid , or monocarboxylate thereof , is less than about g a . e ./ L total herbicide loading) . 50 90 % , 80 % , 70 % , 60 % , 50 % , 40 % , 30 % , 20 % , 10 % , or 5 % In certain embodiments, the herbicidal composition is a A of the concentration of volatilized auxin herbicide in the liquid concentrate containing , for example , a total amount vapor phase surrounding the reference composition lacking ( acid equivalent weight ) of herbicide from about 5 % to the monocarboxylate . about 75 % by weight of the concentrate . In one aspect, the The herbicidal compositions of the present invention may amount is from about 10 % to about 60 % by weight of the 55 comprise a single monocarboxylic acid , or monocarboxylate concentrate . In another aspect, the amount is from about thereof, or a mixture of two or more monocarboxylic acids , 15 % to about 50 % by weight of the concentrate . In another or monocarboxylates thereof. aspect, the amount is from about 20 % to about 40 % by The monocarboxylic acid or monocarboxylate loading of weight of the concentrate . In another aspect, the amount is the herbicidal composition generally will depend upon the from about 25 % to about 35 % by weight of the concentrate . 60 auxin herbicide loading of the herbicidal composition , the In another aspect, the amount is about 30 % by weight of the salt form of the auxin herbicide , and the properties of any concentrate . other components of the herbicidal composition , and will be In certain embodiments , the herbicidal composition is a an amount sufficient to reduce the volatility of the auxin dry concentrate ( e . g ., powder or granules ) containing , for herbicide relative to a reference composition lacking the example , a total amount ( acid equivalent weight ) of herbi- 65 monocarboxylic acid or monocarboxylate , but otherwise cide from about 40 % to about 90 % by weight of the having the same composition . For example , the monoetha concentrate . In one aspect, the amount is from about 50 % to nolamine and diethanolamine salts of dicamba are less US 10 ,212 ,933 B2 10 volatile than the dimethylamine and isopropylamine salts of ratio of alkali metal carbonate to monocarboxylic acid , or dicamba and the loading required for the less volatile salts monocarboxylate thereof, is about 1 : 1 . may be less than the loading required for the more volatile salts . In addition , the loading of the monocarboxylic acid , or G . HERBICIDAL COMPOSITION monocarboxylate thereof, can vary with the specific com - 5 EMBODIMENTS bination of auxin herbicide, optional non - auxin herbicide , and monocarboxylic acid , or monocarboxylate thereof. The herbicidal compositions can be presented in various In the herbicidal compositions of the present invention the forms depending upon the intended use and handling prop molar ratio of the auxin herbicide to the monocarboxylic erties desired . For example , the herbicidal compositions of acid , or monocarboxylate thereof, is typically no less than 10 the present invention can be prepared in dry form ( e . g . , about 1 : 10 and no greater than about 10 : 1. Representative powders , granules , etc . ) or in liquid form ( e . g . , aqueous molar ratios of auxin herbicide acid equivalent ( a . e . ) to total solutions, dispersions, etc . ) . The term “ aqueous ” as used in monocarboxylic acid , or monocarboxylate thereof, are , for this application , however, is not intended to exclude the example , from 1 : 10 to about 10 : 1 , from about 1 : 5 to about 1 presence of non -aqueous ( i. e ., organic ) solvents as long as 5 : 1 , and from about 3 : 1 to about 1 : 3 . In one aspect, the molar water is present. Water is the predominant component of the ratio of auxin herbicide to monocarboxylic acid , or mono ready - to -use compositions and tank mix compositions dis carboxylate thereof, is about 2 : 1 to about 1 : 2 . In another closed in this application . aspect , the molar ratio of auxin herbicide to monocarboxylic Among the various composition presentations of the acid , or monocarboxylate thereof, is about 1: 1 . 2020 inventioninven are the following : In certain embodiments , the herbicidal composition con (a ) a ready - to -use aqueous herbicidal composition that centrates of the present invention contain an amount ( acid can be applied to unwanted plants without the need for equivalent weight) of the monocarboxylic acid , or mono - further dilution with water or other preparation ; carboxylate thereof, from about 0 .25 % to about 25 % by ( b ) a herbicidal composition concentrate that is diluted weight of the concentrate . In one aspect , the amount is from 25 with water , and optionally combined with other herbicide about 1 % to about 20 % by weight of the concentrate . In and non -herbicide materials , prior to application (including , another aspect , the amount is from about 2 % to about 15 % e . g. , dry mixes and premixes ) ; by weight of the concentrate . In another aspect, the concen ( c ) a herbicidal composition application mixture prepared trate is a liquid concentrate and the amount (acid equivalent by diluting a herbicidal composition concentrate with water weight ) is from about 2 % to about 10 % by weight of the 30 to form the herbicidal composition application mixture concentrate . In another aspect, the concentrate is a dry which then can be applied to auxin - susceptible plants ; concentrate and the amount (acid equivalent weight) is from ( d ) a herbicidal composition application mixture prepared about 5 % to about 15 % by weight of the concentrate . In another aspect, the monocarboxylic acid , or monocarboxy by combining two or more separate components with water late thereof , is acetic acid , or agriculturally acceptable salt 35 ( e . g . , a tank mix ) to form the herbicidal composition appli thereof. cation mixture which then can be applied to auxin - suscep In certain embodiments, the herbicidal composition tank tible plants ; and mixes of the present invention contain an amount ( acid ( e) a herbicidal composition application mixture prepared equivalent weight) of the monocarboxylic acid , or mono by introducing separate feed streams to a spraying or appli carboxylate thereof. from about 0 .01 % to about 25 % by 40 cation system so that the feed streams are co -mixed to form weight of the tank mix . In one aspect, the amount is from the herbicidal composition application mixture immediately about 0 .01 % to about 20 % by weight of the tank mix . In prior to use . another aspect, the amount is from about 0 .05 % to about In various embodiments , the herbicidal compositions 15 % by weight of the tank mix . In another aspect, the ( ready - to - use , liquid concentrate , tank mix , etc . ) have a pH amount is from about 0 .05 % to about 10 % by weight of the 45 that is equal to or higher than the acid dissociation constant tank mix . In another aspect , the amount is from about 0 . 05 % (pKa ) of the monocarboxylic acid present in the composi to about 5 % by weight of the tank mix . In another aspect, the tion . For example , in certain embodiments , the herbicidal amount is from about 0 . 1 % to about 2 % by weight of the compositions comprise acetic acid (which has a pKa of tank mix . In another aspect, the amount is from about 0 . 1 % about 4 . 8 ) and have a pH equal to or greater than about 4 . 8 . to about 1 % by weight of the tank mix . In another aspect, the 50 In the case of herbicidal compositions comprising dicamba monocarboxylic acid , or monocarboxylate thereof, is acetic and an effective amount of acetic acid , dicamba volatility acid , or agriculturally acceptable salt thereof. generally decreases as composition pH increases with 3 . Alkali Metal Phosphate / Alkali Metal Carbonate Loading dicamba volatility reaching substantially non -detectable lev When the herbicidal composition comprises an alkali els at a composition pH of about 5. 2 as measured in a plant metal phosphate , such as dipotassium phosphate , the molar 55 response study. ratio of the alkali metal phosphate to the monocarboxylic 1 . Illustrative Composition Embodiments ( Auxin Herbicide acid , or monocarboxylate thereof, can range , for example , Concentrates ) from about 1 : 5 to about 5 :1 , from about 3 : 1 to about 1 : 3 , or One embodiment of the invention is directed to a herbi from about 2 : 1 to about 1 : 2 . In one embodiment, the molar cidal composition concentrate comprising : ratio of alkali metal phosphate to monocarboxylic acid , or 60 at least one auxin herbicide ; and monocarboxylate thereof, is about 1 : 1 . at least one monocarboxylic acid , or a monocarboxylate When the herbicidal composition comprises an alkali thereof; metal carbonate , such as potassium carbonate , the molar wherein the concentrate satisfies one or more of the ratio of the alkali metal carbonate to the monocarboxylic following conditions : acid , or monocarboxylate thereof, can range , for example , 65 the molar ratio of monocarboxylic acid , or monocarboxy from about 1 : 5 to about 5 : 1 , from about 3 : 1 to about 1 : 3 , or late thereof, to auxin herbicide is from about 1 : 10 to about from about 2 : 1 to about 1 : 2 . In one embodiment, the molar 10 : 1; US 10 , 212 , 933 B2 11 12 the acid equivalent weight ratio of monocarboxylic acid , In further embodiments , the herbicidal composition con or monocarboxylate thereof, to auxin herbicide is from centrate further comprises an alkalimetal phosphate , such as about 1 : 10 to about 5 : 1 ; dipotassium phosphate . the concentrate contains an amount ( acid equivalent In further embodiments , the herbicidal composition con weight) of the monocarboxylic acid , or monocarboxylate 5 centrate is a dry powder herbicidal composition . thereof, from about 0 .25 % to about 25 % by weight of the In further embodiments , the herbicidal composition con concentrate ; centrate is an aqueous herbicidal composition . the concentration of the monocarboxylic acid , or mono - In further embodiments , the herbicidal composition con carboxylate thereof, is from about 1 gram (acid equivalent centrate further comprises a non - auxin herbicide . In another weight) / L to about 250 grams ( acid equivalent weight )/ L ; " embodiment, the non - auxin herbicide is selected from the and group consisting of acetochlor , glyphosate, glufosinate , flu the concentrate comprises an amount of the monocarbox mioxazin , fomesafen , and agriculturally acceptable salts ylic acid , or monocarboxylate thereof, sufficient to reduce thereof . In another embodiment, the non - auxin herbicide is the concentration of volatilized auxin herbicide in the vapor 15 glyphosate , or an agriculturally acceptable salt thereof. In phase surrounding the concentrate by at least about 10 % another embodiment, the concentrate comprises a glypho relative to the concentration of volatilized auxin herbicide in sate salt selected from the group consisting of ammonium , the vapor phase surrounding an otherwise identical concen - diammonium , dimethylammonium , monoethanolamine , iso trate lacking the monocarboxylic acid , or monocarboxylate propylamine , and potassium salts , and combinations thereof. thereof. 20 In another embodiment, the concentrate comprising a non In further embodiments , the herbicidal composition con - auxin herbicide satisfies one or more of the following centrate comprises at least one auxin herbicide selected from conditions : the group consisting of dicamba , or an agriculturally accept the sum of the concentration of auxin herbicide and the able salt or ester thereof, and 2 ,4 - D , or an agriculturally concentration of non -auxin herbicide is from about 120 acceptable salt or ester thereof. 25 grams (acid equivalent weight )/ L to about600 grams (acid In further embodiments , the herbicidal composition con - equivalent weight) / L ; centrate comprises dicamba , or an agriculturally acceptable the acid equivalent weight ratio of auxin herbicide to salt or ester thereof. In another embodiment, the concentrate non -auxin herbicide herbicide is from about 1 :5 to about 2 : 1 ; comprises a dicamba salt selected from the group consisting and of N , N -bis - ?aminopropyl ]methylamine , monoethanolamine , 30 the acid equivalent weight ratio of monocarboxylic acid , dimethylamine , isopropylamine, diglycolamine , potassium , or monocarboxylate thereof, to auxin herbicide is from and sodium salts , and combinations thereof. about 1: 10 to about 5 : 1 . In further embodiments , the herbicidal composition con - In further embodiments , the herbicidal composition con centrate comprises 2 ,4 - D , or an agriculturally acceptable salt 35 centrate has a pH greater than or equal to the pK? of the or ester thereof. In another embodiment, the concentrate monocarboxylic acid selected for the composition . comprises a 2 , 4 - D salt selected from the group consisting of 2 . Illustrative Composition Embodiments ( Auxin Herbicide choline , dimethylamine , and isopropylamine salts , and com - Application Mixtures) binations thereof. In another embodiment, the concentrate One embodiment of the invention is directed to a herbi comprises a 2 ,4 - D ester selected from the group consisting 40 cidal composition comprising : of butyl ( i. e ., 2 ,4 -DB ) and isooctyl esters , and combinations at least one auxin herbicide; and thereof. at least one monocarboxylic acid , or a monocarboxylate In further embodiments , the herbicidal composition con - thereof; centrate comprises a monocarboxylate salt . wherein the composition satisfies one or more of the In further embodiments, the herbicidal composition con - 45 following conditions : centrate comprises a C , - CG - alkanoic acid , or an agricultur - the molar ratio of monocarboxylic acid , or monocarboxy ally acceptable salt thereof. In other embodiments , the late thereof, to auxin herbicide is from about 1 : 10 to about herbicidal composition concentrate comprises a C -C5 - al- 10 : 1 ; kanoic acid , or an agriculturally acceptable salt thereof. In the acid equivalent weight ratio of monocarboxylic acid , other embodiments , the herbicidal composition concentrate 50 or monocarboxylate thereof, to auxin herbicide is from comprises a C1- C4- alkanoic acid , or an agriculturally about 1 : 10 to about 5 : 1 ; acceptable salt thereof . In other embodiments , the herbicidal the composition contains an amount ( acid equivalent composition concentrate comprises a C , - Cz - alkanoic acid , weight ) of the monocarboxylic acid , or monocarboxylate or an agriculturally acceptable salt thereof. In other embodi- thereof, from about 0 .01 % to about 25 by weight of the ments , the herbicidal composition concentrate comprises 55 composition ; acetic acid , or an agriculturally acceptable salt thereof. In the concentration of the monocarboxylic acid , or mono other embodiments , the herbicidal composition concentrate carboxylate thereof, is from about 1 gram (acid equivalent comprises formic acid , or an agriculturally acceptable salt w eight ) / L to about 250 grams (acid equivalent weight ) / L ; thereof. and In further embodiments , the monocarboxylate salt or 60 the composition comprises an amount of the monocar acetate salt is a non - ammoniated salt . In another embodi- boxylic acid , or monocarboxylate thereof , sufficient to ment, the monocarboxylate salt or acetate salt is an alkali reduce the concentration of volatilized auxin herbicide in the metal salt . In another embodiment, the monocarboxylate salt vapor phase surrounding the composition by at least about or acetate salt is a potassium salt . In another embodiment, 10 % relative to the concentration of volatilized auxin her the monocarboxylate salt or acetate salt is a sodium salt . 65 bicide in the vapor phase surrounding an otherwise identical In further embodiments, the herbicidal composition con - composition lacking the monocarboxylic acid , or monocar centrate further comprises a buffer . boxylate thereof. US 10 ,212 ,933 B2 13 14 In one aspect , the composition contains an amount (acid the sum of the concentration of auxin herbicide and the equivalent weight) of the monocarboxylic acid , or mono concentration of non -auxin herbicide is from about 1 gram carboxylate thereof, from about 0 . 1 % to about 25 % by (acid equivalent weight) / L to about 50 grams (acid equiva weight of the composition . lent weight) / L ; In further embodiments , the composition comprises at 5 the acid equivalent weight ratio of auxin herbicide to least one auxin herbicide selected from the group consisting non - auxin herbicide is from about 1 : 5 to about 2 : 1 ; and of dicamba, or an agriculturally acceptable salt or ester the acid equivalent weight ratio of monocarboxylic acid , thereof , and 2 , 4 - D , or an agriculturally acceptable salt or or monocarboxylate thereof, to auxin herbicide is from ester thereof. about 1: 10 to about 5 : 1 . In further embodiments , the composition comprises 3 . Illustrative Composition Embodiments (Dicamba Con dicamba , or an agriculturally acceptable salt or ester thereof. centrate ) In another embodiment, the composition comprises a Compositions of particular interest include herbicidal dicamba salt selected from the group consisting of N , N - bis compositions comprising dicamba , or an agriculturally [ aminopropyl ]methylamine , monoethanolamine , dimethyl- 16 acceptable salt or ester thereof; acetic acid , or an agricul amine , isopropylamine , diglycolamine , potassium , and turally acceptable salt thereof; and , optionally, glyphosate , sodium salts , and combinations thereof. or an agriculturally acceptable salt thereof. In further embodiments , the composition comprises 2 , 4 - One embodiment of the invention is directed to a herbi D , or an agriculturally acceptable salt or ester thereof. In cidal composition concentrate comprising : another embodiment, the composition comprises a 2 , 4 - D salt 20 dicamba, or an agriculturally acceptable salt or ester selected from the group consisting of choline, dimethylam - thereof ; and ine , and isopropylamine salts , and combinations thereof. In acetic acid , or an agriculturally acceptable salt thereof; another embodiment , the composition comprises a 2 , 4 - D wherein the molar ratio of acetic acid , or agriculturally ester such as 2 , 4 -DB . acceptable salt thereof, to dicamba , or agriculturally accept In further embodiments , the composition comprises a 25 able salt or ester thereof, is from about 1 : 10 to about 10 : 1 . monocarboxylate salt. In another embodiment, the herbicidal composition con In further embodiments , the herbicidal composition con centrate comprises: centrate comprises a C -Cr - alkanoic acid , or an agricultur ( a ) dicamba, or an agriculturally acceptable salt or ester ally acceptable salt thereof. In other embodiments , the herbicidal composition concentrate comprises a C , -Cz - al- 30 thereof; and kanoic acid , or an agriculturally acceptable salt thereof. In (b ) acetic acid , or an agriculturally acceptable salt thereof; other embodiments, the herbicidal composition concentrate wherein the acid equivalent weight ratio of acetic acid , or comprises a C , -C4 - alkanoic acid , or an agriculturally agriculturally acceptable salt thereof, to dicamba , or agri acceptable salt thereof. In other embodiments , the herbicidal culturally acceptable salt or ester thereof, is from about 1 : 10 composition concentrate comprises a C , - Cz- alkanoic acid , 350 or an agriculturally acceptable salt thereof. In otherther embodi In another embodiment , the herbicidal composition con ments, the herbicidal composition concentrate comprises centrate comprises : acetic acid , or an agriculturally acceptable salt thereof. In ( a ) dicamba , or an agriculturally acceptable salt or ester other embodiments , the herbicidal composition concentrate thereof ; and comprises formic acid , or an agriculturally acceptable salt 40 (b ) acetic acid , or an agriculturally acceptable salt thereof; thereof. wherein the concentrate contains an amount ( acid equiva In further embodiments , the monocarboxylate salt or lent weight ) of the acetic acid , or agriculturally acceptable acetate salt is a non -ammoniated salt. In another embodi - salt thereof, from about 0 .25 % to about 25 % by weight of ment, the monocarboxylate salt or acetate salt is an alkali the concentrate . metal salt . In another embodiment, the monocarboxylate salt 45 In another embodiment, the herbicidal composition con or acetate salt is a potassium salt . In another embodiment, centrate comprises : the monocarboxylate salt or acetate salt is a sodium salt. ( a ) dicamba , or an agriculturally acceptable salt or ester In further embodiments , the composition further com - thereof; and prises a buffer. ( b ) acetic acid , or an agriculturally acceptable salt thereof; In further embodiments , the herbicidal composition con - 50 wherein the concentration of the acetic acid , or agricul centrate further comprises an alkali metal phosphate , such as turally acceptable salt thereof, is from about 1 gram ( acid dipotassium phosphate . equivalent weight )/ L to about 250 grams ( acid equivalent In further embodiments , the composition is an aqueous weight )/ L . herbicidal composition . In another embodiment, the herbicidal composition con In further embodiments , the composition further com - 55 centrate comprises : prises a non - auxin herbicide . In another embodiment, the ( a ) dicamba, or an agriculturally acceptable salt or ester non -auxin herbicide is selected from the group consisting of thereof; and acetochlor, glyphosate , glufosinate , flumioxazin , fomesafen , ( b ) acetic acid , or an agriculturally acceptable salt thereof; and agriculturally acceptable salts thereof. In another wherein the concentration of dicamba , or an agriculturally embodiment, the non -auxin herbicide is glyphosate , or an 60 acceptable salt or ester thereof, is from about 120 grams agriculturally acceptable salt thereof. In another embodi- (acid equivalent weight) /L to about 600 grams (acid equiva ment, the concentrate comprises a glyphosate salt selected lent weight) /L . from the group consisting of ammonium , diammonium , In another embodiment, the herbicidal composition con dimethylammonium , monoethanolamine , isopropylamine , centrate comprises : and potassium salts , and combinations thereof. In another 65 ( a ) dicamba , or an agriculturally acceptable salt or ester embodiment, the concentrate comprising a non - auxin her - thereof; and bicide satisfies one or more of the following conditions: (b ) acetic acid , or an agriculturally acceptable salt thereof ; US 10 , 212 ,933 B2 15 wherein the concentration of dicamba , or an agriculturally ( a ) dicamba , or an agriculturally acceptable salt or ester acceptable salt or ester thereof, is from about 120 grams thereof ; ( acid equivalent weight) / L to about 600 grams (acid equiva ( b ) glyphosate , or an agriculturally acceptable salt lent weight ) / L ; and thereof; and wherein the acid equivalent weight ratio of acetic acid , or 5 ( c ) acetic acid , or an agriculturally acceptable salt thereof; agriculturally acceptable salt thereof, to dicamba , or agri - wherein the molar ratio of acetic acid , or agriculturally culturally acceptable salt or ester thereof, is from about 1: 10 acceptable salt thereof, to dicamba, or agriculturally to about 5 : 1 . acceptable salt or ester thereof , is from about 1 : 10 to In another embodiment , the herbicidal composition con about 10 : 1 . centrate comprises : 10 In another embodiment , the herbicidal composition con ( a ) dicamba, or an agriculturally acceptable salt or ester c entrate comprises : thereof; and ( a ) dicamba , or an agriculturally acceptable salt or ester ( b ) acetic acid , or an agriculturally acceptable salt thereof; thereof; wherein the concentrate comprises an amount of the (b ) glyphosate , or an agriculturally acceptable salt acetic acid , or agriculturally acceptable salt thereof, suffi- 15 thereof; and cient to reduce the concentration of volatilized dicamba , or ( c ) acetic acid , or an agriculturally acceptable salt thereof; agriculturally acceptable salt or ester thereof , in the vapor wherein the acid equivalent weight ratio of acetic acid , or phase surrounding the concentrate by at least about 10 % , agriculturally acceptable salt thereof, to dicamba, or 20 % , 30 % , 40 % , 50 % , 60 % , 70 % , 80 % , 90 % , or 95 % A agriculturally acceptable salt or ester thereof, is from relative to the concentration of volatilized dicamba , or 20 about 1 : 10 to about 5 : 1 . agriculturally acceptable salt or ester thereof, in the vapor In another embodiment, the herbicidal composition con phase surrounding an otherwise identical concentrate lack - centrate comprises : ing the acetic acid , or agriculturally acceptable salt thereof. ( a ) dicamba, or an agriculturally acceptable salt or ester In further embodiments , the herbicidal composition con thereof; centrate comprises a dicamba salt selected from the group 25 (b ) glyphosate , or an agriculturally acceptable salt consisting of N , N -bis - ?aminopropyl] methylamine , thereof ; and monoethanolamine , dim ethylamine, isopropylamine , digly ( c ) acetic acid , or an agriculturally acceptable salt thereof; colamine, potassium , and sodium salts , and combinations wherein the concentrate contains an amount (acid equiva thereof. lentweight ) of the acetic acid , or agriculturally accept In further embodiments , the herbicidal composition con - 30 a ble salt thereof, from about 0 .25 % to about 25 % by centrate comprises an acetate salt . In another embodiment, weight of the concentrate. the acetate salt is an alkali metal salt . In another embodi In another embodiment, the herbicidal composition con ment, the acetate salt is a potassium salt. In another embodi- centrate comprises: ment, the acetate salt is a sodium salt. ( a ) dicamba , or an agriculturally acceptable salt or ester In further embodiments, the herbicidal composition con - 35 thereof; centrate further comprises a buffer . ( b ) glyphosate , or an agriculturally acceptable salt In further embodiments , the herbicidal composition con thereof; and centrate further comprises an alkali metal phosphate , such as (c ) acetic acid , or an agriculturally acceptable salt thereof; dipotassium phosphate . wherein the concentration of the acetic acid , or agricul In further embodiments , the herbicidal composition con - 40 turally acceptable salt thereof, is from about 1 gram centrate is a dry powder herbicidal composition . (acid equivalent weight) /L to about 250 grams (acid In further embodiments , the herbicidal composition con equivalent weight )/ L . centrate is an aqueous herbicidal composition . In another embodiment, the herbicidal composition con In further embodiments, the herbicidal composition con - centrate comprises : centrate further comprises a non -auxin herbicide . In another 45 (a ) dicamba , or an agriculturally acceptable salt or ester embodiment, the non -auxin herbicide is selected from the thereof; group consisting of acetochlor , glyphosate , glufosinate , flu ( b ) glyphosate , or an agriculturally acceptable salt mioxazin , fomesafen , and agriculturally acceptable salts thereof; and thereof. In another embodiment, the concentrate comprising ( c ) acetic acid , or an agriculturally acceptable salt thereof; a non - auxin herbicide satisfies one or more of the following 50 wherein the sum of the concentration of dicamba , or an conditions: agriculturally acceptable salt or ester thereof, and the the sum of the concentration of auxin herbicide and the concentration of glyphosate , or an agriculturally concentration of non - auxin herbicide is from about 120 acceptable salt thereof, is from about 120 grams ( acid grams (acid equivalent weight) / L to about 600 grams (acid equivalent weight) / L to about 600 grams (acid equiva equivalent weight ) / L ; 55 lent weight) / L . In another embodiment, the sum of the the acid equivalent weight ratio of auxin herbicide to concentration of dicamba , or an agriculturally accept non - auxin herbicide is from about 1 : 5 to about 2 : 1 ; and able salt or ester thereof, and the concentration of the acid equivalent weight ratio of monocarboxylic acid , glyphosate , or an agriculturally acceptable salt thereof, or monocarboxylate thereof, to auxin herbicide is from is from about 360 grams (acid equivalent weight )/ L to about 1 : 10 to about 5 : 1 . 60 about 480 grams (acid equivalent weight ) / L . In further embodiments , the herbicidal composition con In another embodiment, the herbicidal composition con centrate has a pH greater than or equal to the pK , of acetic centrate comprises : acid ( i . e . , 4 . 8 ) . ( a ) dicamba, or an agriculturally acceptable salt or ester 4 . Illustrative Composition Embodiments (Dicamba / Gly thereof; phosate Concentrate ) 65 (b ) glyphosate , or an agriculturally acceptable salt One embodiment of the invention is directed to a herbi thereof; and cidal composition concentrate comprising : ( c ) acetic acid , or an agriculturally acceptable salt thereof; US 10 , 212 , 933 B2 17 wherein the sum of the concentration of dicamba , or an In further embodiments , the herbicidal composition con agriculturally acceptable salt or ester thereof, and the centrate is an aqueous herbicidal composition . concentration of glyphosate , or an agriculturally I n another embodiment, the concentrate comprises a gly acceptable salt thereof, is from about 120 grams (acid phosate salt selected from the group consisting of ammo equivalent weight) / L to about 600 grams (acid equiva - 5 nium , diammonium , dimethylammonium , monoetha lent weight) / L ; and nolamine, isopropylamine , and potassium salts , and wherein the acid equivalent weight ratio of dicamba , or an combinations thereof. agriculturally acceptable salt or ester thereof, to gly In another embodiment, the concentrate satisfies one or phosate , or an agriculturally acceptable salt thereof, is more of the following conditions: from about 1 : 5 to about 2 : 1 . 10 In another embodiment, the herbicidal composition con the sum of the concentration of dicamba , or agriculturally centrate comprisesbrises : acceptable salt thereof, and the concentration of gly (a ) dicamba, or an agriculturally acceptable salt or ester phosate , or agriculturally acceptable salt thereof, is thereof ; from about 120 grams (acid equivalent weight) / L to ( b ) glyphosate , or an agriculturally acceptable salt 15 about 600 grams (acid equivalent weight) / L ; thereof; and the acid equivalent weight ratio of dicamba, or agricul ( c ) acetic acid , or an agriculturally acceptable salt thereof; turally acceptable salt thereof, to glyphosate , or agri wherein the sum of the concentration of dicamba , or an culturally acceptable salt thereof, is from about 1 : 5 to agriculturally acceptable salt or ester thereof, and the about 2 : 1 ; and concentration of glyphosate , or an agriculturally 20 the acid equivalent weight ratio ofmonocarboxylic acid , acceptable salt thereof, is from about 120 grams ( acid or monocarboxylate thereof, to dicamba , or agricultur equivalent weight) / L to about 600 grams ( acid equiva ally acceptable salt thereof, is from about 1 : 10 to about lent weight )/ L ; 5 : 1 . wherein the acid equivalentweight ratio of dicamba , or an In further embodiments , the herbicidal composition con agriculturally acceptable salt or ester thereof, to gly - 25 centrate has a pH greater than or equal to the pK , of acetic phosate , or an agriculturally acceptable salt thereof , is acid ( i . e ., 4 . 8 ) . from about 1 : 5 to about 2 : 1 ; and 5 . Illustrative Composition Embodiments (Dicamba Appli wherein the acid equivalent weight ratio of acetic acid , or cation Mixture ) agriculturally acceptable salt thereof, to dicamba , or In further embodiments , the herbicidal compositions cor agriculturally acceptable salt or ester thereof, is from 30 respond to the compositions described above in the " Illus about 1 : 10 to about 5 : 1 . In another embodiment, the herbicidal composition con trative Composition Embodiment ( Auxin Herbicide Appli centrate comprises : cation Mixture ) " section wherein the auxin herbicide is (a ) dicamba, or an agriculturally acceptable salt or ester dicamba , or an agriculturally acceptable salt or ester thereof. thereof; 35 6 . Illustrative Composition Embodiments (Dicamba /Gly ( b ) glyphosate , or an agriculturally acceptable salt phosate Application Mixture ) thereof ; and In further embodiments , the herbicidal compositions cor ( c ) acetic acid , or an agriculturally acceptable salt thereof; respond to the compositions described above in the “ Illus wherein the concentrate comprises an amount of the trative Composition Embodiment (Auxin Herbicide Appli acetic acid , or agriculturally acceptable salt thereof, 40 cation Mixture ) ” section wherein the auxin herbicide is sufficient to reduce the concentration of volatilized dicamba , or an agriculturally acceptable salt or ester thereof, dicamba, or agriculturally acceptable salt or ester and the compositions further comprise glyphosate , or an thereof , in the vapor phase surrounding the concentrate agriculturally acceptable salt or ester thereof . by at least about 10 % , 20 % , 30 % , 40 % , 50 % , 60 % , 7 . Illustrative Composition Embodiments (Dicamba /Glufo 70 % , 80 % , 90 % , or 95 % A relative to the concentration 45 sinate Application Mixture ) of volatilized dicamba , or agriculturally acceptable salt In further embodiments , the herbicidal compositions cor or ester thereof, in the vapor phase surrounding an respond to the compositions described above in the “ Illus otherwise identical concentrate lacking the acetic acid , trative Composition Embodiment ( Auxin Herbicide Appli or agriculturally acceptable salt thereof. cation Mixture )” section wherein the auxin herbicide is In further embodiments , the herbicidal composition con - 50 dicamba , or an agriculturally acceptable salt or ester thereof, centrate comprises a dicamba salt selected from the group and the compositions further comprise glufosinate , or an consisting of N , N - bis -?aminopropyl ] methylamine , agriculturally acceptable salt or ester thereof . monoethanolamine , dimethylamine , isopropylamine, digly - 8 . Illustrative Composition Embodiments ( 2 , 4 - D ) colamine , potassium , and sodium salts , and combinations Compositions of particular interest also include herbicidal thereof. 55 compositions comprising 2 , 4 - D , or an agriculturally accept In further embodiments , the herbicidal composition con able salt or ester thereof ; acetic acid , or an agriculturally centrate comprises an acetate salt. In another embodiment, acceptable salt thereof; and , optionally , glyphosate , or an the acetate salt is an alkali metal salt . In another embodi - agriculturally acceptable salt thereof . ment, the acetate salt is a potassium salt. In another embodi- In further embodiments, the herbicidal compositions cor ment, the acetate salt is a sodium salt . 60 respond to the compositions described above in the “ Illus In further embodiments, the herbicidal composition con - trative Composition Embodiment (Dicamba Concentrate ) , " centrate further comprises a buffer . " Illustrative Composition Embodiment (Dicamba /Glypho In further embodiments, the herbicidal composition con - sate Concentrate ), " " Illustrative Composition Embodiment centrate further comprises an alkali metal phosphate , such as (Dicamba Application Mixture ) , " " Illustrative Composition dipotassium phosphate . 65 Embodiment (Dicamba /Glyphosate Application Mixture ) " In further embodiments , the herbicidal composition con - and “ Illustrative Composition Embodiment (Dicamba /Glu centrate is a dry powder herbicidal composition . fosinate Application Mixture ) ” sections except that the US 10 , 212 , 933 B2 19 20 dicamba , or agriculturally acceptable salt or ester thereof, is In further embodiments , the liquid concentrate comprises replaced with 2 ,4 - D , or an agriculturally acceptable salt or an acetate salt. In another embodiment, the acetate salt is an ester thereof. alkali metal salt . In another embodiment , the acetate salt is 9 . Illustrative Composition Embodiments (Dicamba Liquid a potassium salt . In another embodiment, the acetate salt is Concentrate ) 5 a sodium salt. One embodiment of the invention is directed to a herbi- In further embodiments , the liquid concentrate comprises cidal composition that is a liquid concentrate comprising: an acetate salt that is formed in situ during the preparation of the liquid concentrate when acetic acid is contacted with dicamba, or an agriculturally acceptable salt or ester a neutralizing base such as an alkali metal hydroxide . For thereof; and f . 10 example , the liquid concentrate can be prepared by mixing acetic acid , or an agriculturally acceptable salt thereof; the dicamba, or agriculturally acceptable salt or ester wherein : thereof , with water followed by the addition of acetic acid the concentrate contains an amount (acid equivalent followed by the addition of the neutralizing base . Although weight ) of the acetic acid , or agriculturally acceptable a specific order of addition of the ingredients is not required salt thereof, from about 1 % to about- 25 %% byby weight of of 15 to ?prepare the final composition , the order of addition the concentrate ; and described above can be advantageous to reduce the heat the concentrate contains an amount ( acid equivalent generation resulting when the ingredients are combined . In weight) of dicamba , or an agriculturally acceptable salt one aspect, the neutralizing base is potassium hydroxide. In or ester thereof, from about 10 % to about 60 % by another aspect, the neutralizing base is sodium hydroxide . weight of the concentrate. 20 10 . Illustrative Composition Embodiments (Dicamba Dry In one aspect , the liquid concentrate has a dicamba Concentrate ) loading from about 300 g a . e ./ L to about 400 g a . e . / L . One embodiment of the invention is directed to a herbi In another embodiment, the liquid concentrate comprises: cidal composition that is a dry concentrate comprising: dicamba , or an agriculturally acceptable salt or ester dicamba, or an agriculturally acceptable salt or ester thereof; and 25 thereof; and acetic acid , or an agriculturally acceptable salt thereof; acetic acid , or an agriculturally acceptable salt thereof; wherein : wherein : the concentrate contains an amount ( acid equivalent the concentrate contains an amount (acid equivalent weight) of the acetic acid , or agriculturally acceptable weight ) of the acetic acid , or agriculturally acceptable salt thereof, from about 2 % to about 20 % by weight of 30 salt thereof, from about 1 % to about 40 % by weight of the concentrate ; and the concentrate ; the concentrate contains an amount (acid equivalent the concentrate contains an amount (acid equivalent weight) of dicamba , or an agriculturally acceptable salt weight ) of dicamba , or an agriculturally acceptable salt or ester thereof, from about 15 % to about 50 % by or ester thereof, from about 40 % to about 90 % by weight of the concentrate . 35 weight of the concentrate ; and In another embodiment, the liquid concentrate comprises : wherein the sum of the acetic acid weight percent and the dicamba, or an agriculturally acceptable salt or ester dicamba weight percent is less than or equal to 100 % . thereof ; and In another embodiment, the dry concentrate comprises : acetic acid , or an agriculturally acceptable salt thereof; dicamba , or an agriculturally acceptable salt or ester wherein : 40 thereof; and the concentrate contains an amount ( acid equivalent acetic acid , or an agriculturally acceptable salt thereof; weight) of the acetic acid , or agriculturally acceptable wherein : salt thereof, from about 3 % to about 15 % by weight of the concentrate contains an amount (acid equivalent the concentrate ; and weight ) of the acetic acid , or agriculturally acceptable the concentrate contains an amount ( acid equivalent 45 salt thereof, from about 3 % to about 30 % by weight of weight) of dicamba , or an agriculturally acceptable salt the concentrate; or ester thereof, from about 20 % to about 40 % by the concentrate contains an amount (acid equivalent weight of the concentrate . weight) of dicamba , or an agriculturally acceptable salt In another embodiment, the liquid concentrate comprises : or ester thereof, from about 50 % to about 80 % by dicamba , or an agriculturally acceptable salt or ester 50 weight of the concentrate ; and thereof; and wherein the sum of the acetic acid weight percent and the acetic acid , or an agriculturally acceptable salt thereof; dicamba weight percent is less than or equal to 100 % . wherein : In another embodiment, the dry concentrate comprises: the concentrate contains an amount ( acid equivalent dicamba , or an agriculturally acceptable salt or ester weight) of the acetic acid , or agriculturally acceptable 55 thereof ; and salt thereof, from about 3 % to about 10 % by weight of acetic acid , or an agriculturally acceptable salt thereof; the concentrate ; and wherein : the concentrate contains an amount ( acid equivalent the concentrate contains an amount ( acid equivalent weight ) of dicamba , or an agriculturally acceptable salt weight ) of the acetic acid , or agriculturally acceptable or ester thereof, from about 25 % to about 35 % by 60 salt thereof, from about 5 % to about 20 % by weight of weight of the concentrate . the concentrate ; and In further embodiments , the liquid concentrate comprises the concentrate contains an amount (acid equivalent a dicamba salt selected from the group consisting of N , N weight ) of dicamba , or an agriculturally acceptable salt bis - [ aminopropyl] methylamine , monoethanolamine , dim or ester thereof, from about 60 % to about 75 % by ethylamine , isopropylamine , diglycolamine , potassium , and 65 weight of the concentrate . sodium salts , and combinations thereof. In one aspect, the In further embodiments , the dry concentrate comprises a liquid concentrate comprises a dicamba diglycolamine salt. dicamba salt selected from the group consisting of N ,N -bis US 10 ,212 , 933 B2 21 22 . [ aminopropyl ]methylamine , monoethanolamine, dimethyl the concentrate contains an amount (acid equivalent amine , isopropylamine , diglycolamine, potassium , and weight) of dicamba , or an agriculturally acceptable salt sodium salts, and combinations thereof. In one aspect , the or ester thereof, from about 4 % to about 15 % by weight liquid concentrate comprises a dicamba diglycolamine salt . of the concentrate ; and In further embodiments , the dry concentrate comprises an 5 the concentrate contains an amount (acid equivalent acetate salt . In another embodiment, the acetate salt is an weight) of glyphosate , or an agriculturally acceptable alkali metal salt . In another embodiment, the acetate salt is a potassium salt. In another embodiment, the acetate salt is salt thereof, from about 8 % to about 30 % by weight of a sodium salt . the concentrate . In further embodiments , the dry concentrate is in the form 10 In another embodiment, the liquid concentrate comprises: of a dry powder. dicamba , or an agriculturally acceptable salt or ester In further embodiments , the dry concentrate is in the form thereof; and of dry granules. glyphosate , or an agriculturally acceptable salt thereof; 11 . Illustrative Composition Embodiments (Dicamba / Gly and phosate Liquid Premix ) 15 acetic acid , or an agriculturally acceptable salt thereof; One embodiment of the invention is directed to a herbi wherein : cidal composition that is a liquid concentrate comprising: the concentrate contains an amount ( acid equivalent dicamba , or an agriculturally acceptable salt or ester weight ) of the acetic acid , or agriculturally acceptable thereof ; and salt thereof, from about 3 % to about 10 % by weight of glyphosate , or an agriculturally acceptable salt thereof ; 20 the concentrate ; and the concentrate contains an amount ( acid equivalent acetic acid , or an agriculturally acceptable salt thereof; weight ) of dicamba , or an agriculturally acceptable salt wherein : or ester thereof, from about 5 % to about 15 % by weight the concentrate contains an amount ( acid equivalent of the concentrate ; and weight) of the acetic acid , or agriculturally acceptable 25 the concentrate contains an amount (acid equivalent salt thereof, from about 1 % to about 25 % by weight of weight ) of glyphosate, or an agriculturally acceptable the concentrate ; salt thereof, from about 10 % to about 30 % by weight the concentrate contains an amount (acid equivalent of the concentrate . weight ) of dicamba , or an agriculturally acceptable salt In further embodiments , the liquid concentrate comprises or ester thereof, from about 2 % to about 25 % by weight 30 a dicamba salt selected from the group consisting of N , N of the concentrate; and bis - [aminopropyl ) methylamine , monoethanolamine , dim the concentrate contains an amount (acid equivalent ethylamine , isopropylamine, diglycolamine, potassium , and weight ) of glyphosate , or an agriculturally acceptable sodium salts , and combinations thereof. In one aspect, the salt thereof , from about 4 % to about 50 % by weight of liquid concentrate comprises a dicamba diglycolamine salt . the concentrate . 35 In further embodiments , the liquid concentrate comprises In one aspect , the liquid concentrate has a total herbicide an acetate salt . In another embodiment, the acetate salt is an loading from about 350 g a . e ./ L to about 500 g a . e ./ L . alkali metal salt . In another embodiment, the acetate salt is In another embodiment , the liquid concentrate comprises : a potassium salt . In another embodiment, the acetate salt is dicamba , or an agriculturally acceptable salt or ester a sodium salt. thereof; and 40 In further embodiments , the liquid concentrate comprises glyphosate , or an agriculturally acceptable salt thereof; an acetate salt that is formed in situ during the preparation and of the liquid concentrate when acetic acid is contacted with acetic acid , or an agriculturally acceptable salt thereof; a neutralizing base such as an alkali metal hydroxide . For wherein : example , the liquid concentrate can be prepared by mixing the concentrate contains an amount ( acid equivalent 45 the dicamba , or agriculturally acceptable salt or ester weight ) of the acetic acid , or agriculturally acceptable thereof, with water followed by the addition of acetic acid salt thereof, from about 2 % to about 20 % by weight of followed by the addition of the neutralizing base . Although the concentrate ; a specific order of addition of the ingredients is not required the concentrate contains an amount (acid equivalent to prepare the final composition , the order of addition weight) of dicamba , or an agriculturally acceptable salt 50 described above can be advantageous to reduce the heat or ester thereof, from about 3 % to about 20 % by weight generation resulting when the ingredients are combined . In of the concentrate ; and one aspect , the neutralizing base is potassium hydroxide . In the concentrate contains an amount (acid equivalent another aspect , the neutralizing base is sodium hydroxide . weight) of glyphosate , or an agriculturally acceptable 12. Illustrative Composition Embodiments (Dicamba / Gly salt thereof, from about 6 % to about 40 % by weight of 55 phosate Dry Premix ) the concentrate . One embodiment of the invention is directed to a herbi In another embodiment, the liquid concentrate comprises : cidal composition that is a dry concentrate comprising : dicamba , or an agriculturally acceptable salt or ester dicamba , or an agriculturally acceptable salt or ester thereof; and thereof; and glyphosate , or an agriculturally acceptable salt thereof; 60 glyphosate , or an agriculturally acceptable salt thereof; and and acetic acid , or an agriculturally acceptable salt thereof ; acetic acid , or an agriculturally acceptable salt thereof; wherein : wherein : the concentrate contains an amount ( acid equivalent the concentrate contains an amount ( acid equivalent weight) of the acetic acid , or agriculturally acceptable 65 weight) of the acetic acid , or agriculturally acceptable salt thereof, from about 3 % to about 15 % by weight of salt thereof, from about 1 % to about 40 % by weight of the concentrate ; the concentrate ; US 10 ,212 , 933 B2 23 24 the concentrate contains an amount (acid equivalent 13 . Illustrative Composition Embodiments ( Combination weight) of dicamba , or an agriculturally acceptable salt Package ) or ester thereof, from about 5 % to about 40 % by weight One embodiment of the invention is directed to a com of the concentrate; bination package comprising a first container comprising the concentrate contains an amount (acid equivalent 5 dicamba , or an agriculturally acceptable salt or ester thereof; weight) of glyphosate , or an agriculturally acceptable and a second container comprising acetic acid , or an agri salt thereof, from about 40 % to about 80 % by weight culturally acceptable salt thereof. In one aspect , the first of the concentrate ; and container comprises dicamba, or an agriculturally acceptable wherein the sum of the acetic acid weight percent, the salt or ester thereof , in an amount (acid equivalent weight ) dicamba weight percent, and the glyphosate weight 10 that is at least about 20 % by weight of the first container. In percent is less than or equal to 100 % . one aspect, the first container contains a liquid composition In another embodiment, the dry concentrate comprises : comprising dicamba , or an agriculturally acceptable salt or dicamba , or an agriculturally acceptable salt or ester ester thereof. In one aspect , the first container contains a dry thereof; and composition comprising dicamba, or an agriculturally glyphosate , or an agriculturally acceptable salt thereof; 15 acceptable salt or ester thereof. and In another embodiment, the invention is directed to a acetic acid , or an agriculturally acceptable salt thereof; combination package comprising a first container compris wherein : ing dicamba, or an agriculturally acceptable salt or ester the concentrate contains an amount (acid equivalent thereof; a second container comprising glyphosate , or an weight) of the acetic acid , or agriculturally acceptable 20 agriculturally acceptable salt thereof; and a third container salt thereof, from about 3 % to about 30 % by weight of comprising acetic acid , or an agriculturally acceptable salt the concentrate ; thereof . In one aspect, the first container comprises dicamba , the concentrate contains an amount (acid equivalent or an agriculturally acceptable salt or ester thereof, in an weight) of dicamba , or an agriculturally acceptable salt amount (acid equivalentweight ) that is at least about 20 % by or ester thereof, from about 10 % to about 35 % by 25 weight of the first container. In one aspect , the first container weight of the concentrate; and contains a liquid composition comprising dicamba , or an the concentrate contains an amount (acid equivalent agriculturally acceptable salt or ester thereof. In one aspect, weight ) of glyphosate , or an agriculturally acceptable the first container contains a dry composition comprising salt thereof, from about 40 % to about 70 % by weight dicamba , or an agriculturally acceptable salt or ester thereof . of the concentrate ; and 30 In one aspect, the second container comprises glyphosate , or wherein the sum of the acetic acid weight percent, the an agriculturally acceptable salt thereof, in an amount ( acid dicamba weight percent, and the glyphosate weight equivalent weight) that is at least about 20 % by weight of the percent is less than or equal to 100 % . second container. In one aspect, the second container con In another embodiment, the dry concentrate comprises: tains a liquid composition comprising glyphosate , or an dicamba , or an agriculturally acceptable salt or ester 35 agriculturally acceptable salt thereof. In one aspect, the thereof; and second container contains a dry composition comprising glyphosate , or an agriculturally acceptable salt thereof; glyphosate , or an agriculturally acceptable salt thereof. and In another embodiment, the invention is directed to a acetic acid , or an agriculturally acceptable salt thereof; combination package comprising a first container compris wherein : 40 ing dicamba, or an agriculturally acceptable salt or ester the concentrate contains an amount (acid equivalent thereof; a second container comprising glufosinate , or an weight) of the acetic acid , or agriculturally acceptable agriculturally acceptable salt or ester thereof; and a third salt thereof, from about 5 % to about 15 % by weight of container comprising acetic acid , or an agriculturally accept the concentrate ; able salt thereof. In one aspect, the first container comprises the concentrate contains an amount ( acid equivalent 45 dicamba , or an agriculturally acceptable salt or ester thereof, weight) of dicamba , or an agriculturally acceptable salt in an amount ( acid equivalent weight) that is at least about or ester thereof, from about 20 % to about 30 % by 20 % by weight of the first container . In one aspect , the first weight of the concentrate ; and container contains a liquid composition comprising the concentrate contains an amount (acid equivalent dicamba , or an agriculturally acceptable salt or ester thereof. weight ) of glyphosate , or an agriculturally acceptable 50 In one aspect, the first container contains a dry composition salt thereof, from about 45 % to about 55 % by weight comprising dicamba , or an agriculturally acceptable salt or of the concentrate . ester thereof. In one aspect , the second container comprises In further embodiments , the dry concentrate comprises a glufosinate , or an agriculturally acceptable salt or ester dicamba salt selected from the group consisting of N , N -bis thereof, in an amount (acid equivalent weight) that is at least [aminopropyl ] methylamine , monoethanolamine, dimethyl - 55 about 10 % by weight of the second container. In one aspect , amine , isopropylamine , diglycolamine , potassium , and the second container contains a liquid composition compris sodium salts , and combinations thereof. In one aspect , the ing glufosinate , or an agriculturally acceptable salt or ester liquid concentrate comprises a dicamba diglycolamine salt. thereof. In one aspect, the second container contains a dry In further embodiments , the dry concentrate comprises an composition comprising glufosinate , or an agriculturally acetate salt . In another embodiment, the acetate salt is an 60 acceptable salt or ester thereof. alkali metal salt. In another embodiment, the acetate salt is In another embodiment of the invention is directed to a a potassium salt . In another embodiment, the acetate salt is combination package comprising a first container compris a sodium salt . ing glyphosate , or an agriculturally acceptable salt thereof; In further embodiments , the dry concentrate is in the form and a second container comprising acetic acid , or an agri of a dry powder. 65 culturally acceptable salt thereof. In one aspect, the first In further embodiments , the dry concentrate is in the form container comprises glyphosate , or an agriculturally accept of dry granules . able salt thereof, in an amount ( acid equivalent weight ) that US 10 ,212 ,933 B2 25 26 is at least about 20 % by weight of the first container. In one wherein the molar ratio ofmonocarboxylic acid , ormono aspect, the first container contains a liquid composition carboxylate thereof, to alkali metal phosphate is from comprising glyphosate , or an agriculturally acceptable salt about 1 : 5 to about 5 : 1 ; and thereof. In one aspect, the first container contains a dry w herein the composition contains an amount ( acid composition comprising glyphosate , or an agriculturally 5 equivalent weight) of the monocarboxylic acid , or acceptable salt thereof. monocarboxylate thereof , from about 2 % to about 40 % In another embodiment of the invention is directed to a by weight of the composition . combination package comprising a first container compris In another embodiment, the adjuvant composition for use ing glufosinate , or an agriculturally acceptable salt or ester in the preparation of the aqueous herbicidal application thereof; and a second container comprising acetic acid , or an mixture comprises : agriculturally acceptable salt thereof. In one aspect, the first (a ) acetic acid , or an agriculturally acceptable salt thereof; container comprises glufosinate , or an agriculturally accept and able salt thereof , in an amount ( acid equivalent weight) that ( b ) an alkali metal phosphate ; is at least about 10 % by weight of the first container. In one 15 wherein the molar ratio of acetic acid , or agriculturally aspect, the first container contains a liquid composition acceptable salt thereof, to alkali metal phosphate is from comprising glufosinate , or an agriculturally acceptable salt about 1 : 5 to about 5 : 1 . thereof. In one aspect , the first container contains a dry In another embodiment, the adjuvant composition for use composition comprising glufosinate , or an agriculturally in the preparation of the aqueous herbicidal application acceptable salt thereof. 20 mixture comprises: ( a ) acetic acid , or an agriculturally acceptable salt thereof ; H . HERBICIDAL COMPOSITION ADJUVANT and ( b ) an alkali metal phosphateaute ;, As discussed in more detail later, in certain embodiments wherein the molar ratio of acetic acid , or agriculturally the methods of controlling the growth of auxin -susceptible 25 acceptable salt thereof, to alkali metal phosphate is plants involve the preparation of an application mixture by from about 1 : 5 to about 5 : 1 ; and combining a source of auxin herbicide ( e . g ., CLARITY® ) ; wherein the composition contains an amount ( acid a source of monocarboxylic acid , or a monocarboxylate equivalent weight ) of the acetic acid , or agriculturally thereof; an optional source of non -auxin herbicide ( e . g . , acceptable salt thereof, from about 2 % to about 40 % by DURANGO® or POWERMAX® ) ; and water. Another 30 weight of the composition . embodiment of the present invention , therefore , is directed In another embodiment, the invention relates to an adju to a herbicidal adjuvant composition comprising a mono vant composition for use in the preparation of the aqueous carboxylic acid , or monocarboxylate thereof, and , option - herbicidal application mixture , wherein the adjuvant com ally , an alkali metal phosphate , that can serve as the source position comprises acetic acid , or an agriculturally accept of monocarboxylic acid , or a monocarboxylate thereof, used 35 able salt thereof, in an amount (acid equivalent weight) of in the preparation of the application mixture . about 2 % to about 75 % by weight of the composition . In one In one embodiment, the adjuvant composition for use in aspect, the amount is from about 10 % to about 75 % by the preparation of the herbicidal composition application weight of the composition . In another aspect, the amount is mixture comprises: from about 20 % to about 75 % by weight of the composition . ( a ) at least one monocarboxylic acid , or a monocarboxy - 40 In another aspect, the amount is from about 30 % to about late thereof ; and 75 % by weight of the composition . (b ) an alkali metal phosphate ; In various embodiments of the adjuvant composition , the wherein the molar ratio of monocarboxylic acid , or mono - composition is a dry powder composition . carboxylate thereof, to alkali metal phosphate is from In various embodiments of the adjuvant composition , the about 1 : 5 to about 5 : 1 . 45 composition is a liquid composition , particularly an aqueous In various embodiments , the adjuvant composition com - composition . prises a C - Co- alkanoic acid , or an agriculturally acceptable In various embodiments of the adjuvant composition , the salt thereof. In other embodiments, the adjuvant composition composition comprises a non -ammoniated monocarboxylate comprises a C . - C -alkanoic acid , or an agriculturally or acetate salt . In other embodiments , the salt is an alkali acceptable salt thereof. In other embodiments , the adjuvant 50 metal salt , such as an alkali metal salt . In other embodi composition comprises a C , - C4 - alkanoic acid , or an agri - ments , the salt is a potassium salt or a sodium salt , such as culturally acceptable salt thereof. In other embodiments , the potassium acetate and sodium acetate. adjuvant composition comprises a C , -Cz - alkanoic acid , or in various embodiments of the adjuvant composition , the an agriculturally acceptable salt thereof . In other embodi- alkali metal phosphate is dipotassium phosphate . ments , the adjuvant composition comprises a monocarbox - 55 In various embodiments of the adjuvant composition , the ylic acid is selected from the group consisting of formic composition comprises potassium acetate and dipotassium acid , acetic acid , propionic acid , and benzoic acid . In other phosphate . embodiments , the adjuvant composition comprises acetic acid , or an agriculturally acceptable salt thereof. In other I . METHODS OF REDUCING THE VOLATILITY embodiments , the adjuvant composition comprises formic 60 OF AN AUXIN HERBICIDE acid , or an agriculturally acceptable salt thereof. In another embodiment, the adjuvant composition for use Another embodiment of the present invention is directed in the preparation of the herbicidal composition application to a method of reducing the volatility of an auxin herbicide . mixture comprises: The method generally comprises the step of contacting an ( a ) at least one monocarboxylic acid , or a monocarboxy - 65 auxin herbicide with a volatility - lowering effective amount late thereof; and of a monocarboxylic acid , or a monocarboxylate thereof, ( b ) an alkali metal phosphate ; thereby reducing the volatility of the auxin herbicide . US 10 ,212 , 933 B2 27 28 In one embodiment, the contacting step satisfies at least A “ commercially acceptable rate of weed control” varies one of the following conditions: with the weed species , degree of infestation , environmental the molar ratio of the monocarboxylic acid , or monocar conditions , and the associated crop plant. Typically , com boxylate thereof, contacted with the auxin herbicide is mercially effective weed control is defined as least about from about 1: 10 to about 10 :1 ; 60 % , 65 % , 70 % , 75 % , 80 % , 85 % , 90 % , 95 % or even greater the acid equivalent weight ratio of the monocarboxylic than 95 % . Although it is generally preferable from a com acid , or monocarboxylate thereof, contacted with the mercial viewpoint that 80 to 85 % or more of the weeds be auxin herbicide is from about 1 : 10 to about 5 : 1 ; and destroyed , commercially significant weed control can occur the amount of the monocarboxylic acid , or monocarboxy at much lower levels, particularly with some very noxious, late thereof, contacted with the auxin herbicide is 10U herbicide- resistant plants . “ Weed control, ” as used herein , sufficient to reduce the concentration of volatilized auxin herbicide in the vapor phase by at least about refers to any observable measure of control of plant growth , 10 % , 20 % , 30 % , 40 % , 50 % , 60 % , 70 % , 80 % , 90 % , or which can include one or more of the actions of ( 1 ) killing , 95 % relative to the concentration of volatilized auxin ( 2 ) inhibiting growth , reproduction or proliferation , and ( 3 ) herbicide in the vapor phase for an auxin herbicide in 15 removing, destroying , or otherwise diminishing the occur the absence of the monocarboxylic acid , or monocar rence and activity of plants . Weed control can be measured boxylate thereof. by any of the various methods known in the art . For Volatilization can be measured by conventional means example , weed control can be determined as a percentage as known to those skilled in the art . In one such method , for compared to untreated plants following a standard procedure example , a gas stream is passed over an auxin herbicide 20 wherein a visual assessment of plant mortality and growth composition and the auxin herbicide volatilizes from the reduction is made by one skilled in the art specially trained composition into the gas stream which is then quantitatively to make such assessments . In another control measurement analyzed for auxin herbicide content by methods known in method , control is defined as an average plant weight the art. In another method , an auxin herbicide composition reduction percentage between treated and untreated plants . is distilled and the distillation condensate and / or distilled 25 Preferably, commercial weed control is achieved at no composition is analyzed for auxin herbicide content. In still greater than 30 days after treatment (DAT ) , such as from 18 another method , auxin herbicide volatilization is qualita - to 30 DAT . tively assessed in a plant response study on a chosen A “ commercially acceptable rate of crop injury ” for the sensitive species which will be clear to one of skill in the art present invention likewise varies with the crop plant species . It is believed that the addition of the monocarboxylic acid , 30 Typically, a commercially acceptable rate of crop injury is or monocarboxylate thereof, at the loading values discussed defined less than about 20 % , 15 % , 10 % or even less than above to the herbicidal compositions of the present inven - about 5 % . Crop damage can be measured by any means tion effectively reduces auxin herbicide volatility and the known in the art , such as those describe above for weed associated crop injury without significantly reducing auxin control determination . Preferably , crop damage appears no herbicide effectiveness . 35 more than from 10 % to 20 % at no greater than 30 DAT , such In one embodiment, no reduction in auxin herbicide as from 3 to 21 or from 3 to 30 DAT. effectiveness is observed for a herbicidal composition of the present invention relative to a reference composition lacking J. METHODS OF CONTROLLING GROWTH OF the monocarboxylic acid , or monocarboxylate thereof, but AUXIN - SUSCEPTIBLE PLANTS otherwise having the same composition . 40 In another embodiment, the auxin herbicide effectiveness Another embodiment of the present invention is directed of a herbicidal composition of the present invention is at to methods of controlling the growth of auxin - susceptible least about 80 % , 85 % , 90 % , 95 % , or 99 % of the auxin plants , particularly those growing in and / or adjacent to a herbicide effectiveness of a reference composition lacking field of crop plants . The methods generally comprise apply the monocarboxylic acid , or monocarboxylate thereof, but 45 ing to the auxin - susceptible plants an aqueous herbicidal otherwise having the same composition . composition mixture comprising at least one auxin herbi In another embodiment, a reduced rate of crop injury is cide ; at least one monocarboxylic acid , or monocarboxylate observed for a herbicidal composition of the present inven - thereof ; and , optionally , a non - auxin herbicide ; wherein the tion relative to a reference composition lacking the mono application mixture exhibits reduced auxin herbicide vola carboxylic acid , or monocarboxylate thereof, but otherwise 50 tility relative to an otherwise identical application mixture having the same composition . lacking the monocarboxylic acid , or monocarboxylate In another embodiment, the rate of crop injury associated thereof. with a herbicidal composition of the present invention is less The aqueous herbicidal composition mixture applied to than about 90 % , 80 % , 70 % , 60 % , or 50 % of the crop injury the auxin - susceptible plants can be provided , for example , in associated with a reference composition lacking the mono - 55 the following manner: carboxylic acid , or monocarboxylate thereof, but otherwise (a ) as a ready -to - use aqueous herbicidal composition that having the same composition . can be applied without the need for further dilution In another embodiment , a reduction in the rate of crop with water or other preparation ; injury and no reduction in auxin herbicide effectiveness are ( b ) as a herbicidal composition application mixture pre observed for the herbicidal compositions of the present 60 pared by diluting with water any of the herbicidal invention relative to a reference composition lacking the composition concentrates within in the scope of the monocarboxylic acid , or monocarboxylate thereof, but oth present disclosure; erwise having the same composition . ( c ) as a herbicidal composition application mixture pre In another embodiment , the herbicidal composition load pared by combining two or more separate components ing of the monocarboxylic acid , or monocarboxylate thereof, 65 with water ( e . g . , a tank mix ) ; is sufficient to provide both commercially acceptable weed ( d ) as a herbicidal composition application mixture pre control and a commercially acceptable rate of crop injury . pared by introducing separate feed streams to a spray US 10 ,212 ,933 B2 29 30 ing or application system so that the feed streams are wherein the application mixture satisfies one or more of co -mixed immediately prior to use ; or the following conditions : ( e ) in any other manner reasonably adapted to apply to the molar ratio of monocarboxylic acid , or monocarboxy auxin - susceptible plants a herbicidal composition com late thereof, to auxin herbicide is from about 1: 10 to prising the auxin herbicide in admixture with the mono - 5 about 10 :1 ; carboxylic acid , or monocarboxylate thereof. the acid equivalent weight ratio ofmonocarboxylic acid , In one embodiment, the methods of controlling the growth of auxin - susceptible plants comprise the steps of: or monocarboxylate thereof, to auxin herbicide is from ( a ) preparing an aqueous herbicidal application mixture about 1 : 10 to about 5 : 1 ; by diluting with water a herbicidal composition con - 10 the application mixture contains an amount ( acid equiva centrate of any of the herbicidal composition concen lent weight ) of the monocarboxylic acid , or monocar trates disclosed in this application ; and boxylate thereof, from about 0 .01 % to about 25 by (b ) applying a herbicidally effective amount of the appli weight of the application mixture; cation mixture to the auxin -susceptible plants . the concentration of the monocarboxylic acid , or mono In another embodiment, the preparing step does not 15 carboxylate thereof, is from about 1 gram ( acid equiva comprise separately introducing a pH - lowering agent ( e . g . , lent weight) / L to about 250 grams ( acid equivalent an acidifying agent) with the concentrate and water during weight) / L ; and the preparation of the application mixture ; wherein the the application mixture comprises an amount of the pH -lowering agent is one that is capable of lowering the pH monocarboxylic acid , or monocarboxylate thereof, suf of the application mixture in the absence of any buffering 20 ficient to reduce the concentration of volatilized auxin provided by other components of the application mixture . herbicide in the vapor phase surrounding the applica In one embodiment, the methods of controlling the tion mixture by at least about 10 % relative to the growth of auxin - susceptible plants comprise the steps of: concentration of volatilized auxin herbicide in the ( a ) combining a source of auxin herbicide ; a source of vapor phase surrounding an otherwise identical appli monocarboxylic acid , or a monocarboxylate thereof ; 25 cation mixture lacking the monocarboxylic acid , or and water to prepare an aqueous herbicidal application monocarboxylate thereof . mixture ; and In one aspect, the application mixture contains an amount ( b ) applying a herbicidally effective amount of the appli - ( acid equivalent weight) of the monocarboxylic acid , or cation mixture to the auxin -susceptible plants ; monocarboxylate thereof, from about 0 . 1 % to about 25 % , by wherein the application mixture satisfies one or more of 30 weight of the application mixture . the following conditions : When the methods of controlling the growth of auxin themolar ratio of monocarboxylic acid , or monocarboxy - susceptible plants involve the use of a herbicidal composi late thereof, to auxin herbicide is from about 1 : 10 to tion application mixture comprising a non -auxin herbicide , about 10 : 1 ; the application mixture generally satisfies one or more of the the acid equivalent weight ratio of monocarboxylic acid , 35 following conditions: or monocarboxylate thereof, to auxin herbicide is from the sum of the concentration of auxin herbicide and the about 1 : 10 to about 5 : 1 ; concentration of non -auxin herbicide is from about 1 the application mixture contains an amount ( acid equiva gram (acid equivalent weight) / L to about 50 grams lent weight) of the monocarboxylic acid , or monocar ( acid equivalent weight) / L ; boxylate thereof, from about 0 .01 % to about 25 by 40 the acid equivalent weight ratio of auxin herbicide to weight of the application mixture ; non - auxin herbicide is from about 1 : 5 to about 2 : 1 ; and the concentration of the monocarboxylic acid , or mono the acid equivalent weight ratio of monocarboxylic acid , carboxylate thereof, is from about 1 gram (acid equiva or monocarboxylate thereof, to auxin herbicide is from lent weight )/ L to about 250 grams ( acid equivalent about 1 : 10 to about 5 : 1. weight) / L ; and 45 In various embodiments of the described methods of the application mixture comprises an amount of the controlling the growth of auxin - susceptible plants , the appli monocarboxylic acid , or monocarboxylate thereof, suf- cation mixture comprises a non - auxin herbicide is selected ficient to reduce the concentration of volatilized auxin from the group consisting of acetochlor, glyphosate , glufo herbicide in the vapor phase surrounding the applica - sinate , flumioxazin , fomesafen , and agriculturally accept tion mixture by at least about 10 % relative to the 50 able salts thereof. In one embodiment, the application mix concentration of volatilized auxin herbicide in the ture comprises glyphosate , or an agriculturally acceptable vapor phase surrounding an otherwise identical appli salt thereof. In another embodiment, the application mixture cation mixture lacking the monocarboxylic acid , or comprises glufosinate, or an agriculturally acceptable salt monocarboxylate thereof. thereof. In one aspect, the application mixture contains an amount 55 In various embodiments of the described methods of (acid equivalent weight) of the monocarboxylic acid , or controlling the growth of auxin - susceptible plants , the auxin monocarboxylate thereof, from about 0 . 1 % to about 25 % , by herbicide is selected from the group consisting of dicamba , weight of the application mixture . or an agriculturally acceptable salt or ester thereof, and In another embodiment, the methods of controlling the 2 , 4 - D , or an agriculturally acceptable salt or ester thereof. growth of auxin - susceptible plants comprise the steps of: 60 In various embodiments of the described methods of ( a ) combining a source of auxin herbicide ; a source of controlling the growth of auxin - susceptible plants , the auxin non - auxin herbicide , or agriculturally acceptable salt herbicide is dicamba, or an agriculturally acceptable salt or thereof; a source of monocarboxylic acid , or a mono - ester thereof. carboxylate thereof; and water to prepare an aqueous In various embodiments of the described methods of herbicidal application mixture ; and 65 controlling the growth of auxin -susceptible plants , the auxin ( b ) applying a herbicidally effective amount of the appli - herbicide is 2 , 4 - D , or an agriculturally acceptable salt or cation mixture to the auxin -susceptible plants ; ester thereof. US 10 , 212 , 933 B2 31 32 In various embodiments of the described methods of crops , flowers , and root crops. Crop plants further encom controlling the growth of auxin -susceptible plants , the appli - pass hybrids, inbreds , and transgenic or genetically modified cation mixture comprises a monocarboxylate salt . plants. In various embodiments of the described methods of In some embodiments , the crop plants are auxin tolerant controlling the growth of auxin - susceptible plants , the appli - 5 species that are not susceptible to auxin herbicides or are a cation mixture comprises acetic acid , or an agriculturally transgenic species that contain an auxin ( e .g ., dicamba ) acceptable salt thereof. resistant trait . Examples include dicamba resistant corn , In various embodiments of the described methods of cotton or soybean . Dicamba resistant crops can further controlling the growth of auxin - susceptible plants, the comprise one or more additional traits including , without monocarboxylate or acetate salt is a non - ammoniated salt. In limitation : herbicide resistance (e . g. , resistance to other still other embodiments , the salt is an alkali metal salt . In auxin herbicides ( e . g ., 2, 4 - D or fluoroxypyr ), glyphosate , still other embodiments , the salt is a potassium salt . In still glufosinate , acetolactate synthase inhibitor herbicides ( e . g . , other embodiments , the salt is a sodium salt . imazamox , imazethapyr, imazaquin and imazapic ) , acetyl In various embodiments of the described methods of , COA carboxylase inhibitors ( e . g ., sethoxydim and controlling the growth of auxin - susceptible plants , the appli - clethodim ) , etc . ) ; insect resistance such as Bacillus thuringi cation mixture further comprises a buffer. ensis (Bt ) ; high oil ; high lysine ; high starch ; nutritional In various embodiments of the described methods of density ; and / or drought resistance . controlling the growth of auxin -susceptible plants , the appli - In some embodiments , the weeds and /or crop plants are cation mixture further comprises an alkali metal phosphate , 20 glyphosate tolerant or contain a glyphosate resistant trait . such as dipotassium phosphate . Examples include glyphosate resistant corn , cotton or soy In various embodiments of the described methods of bean . controlling the growth of auxin - susceptible plants , the com - In some embodiments , the crop plants comprise stacked bining step does not comprise separately introducing a traits such as dicamba and glyphosate resistance ; dicamba pH - lowering agent with the source of auxin herbicide ; the 25 and glufosinate resistance ; dicamba and acetolactate syn source ofmonocarboxylic acid , or monocarboxylate thereof; thase (ALS ) or acetohydroxy acid synthase (AHAS ) resis and water during the preparation of the application mixture ; tance ; dicamba , glyphosate and glufosinate resistance ; wherein the pH - lowering agent is one that is capable of dicamba , glyphosate and ALS or AHAS resistance ; dicamba , lowering the pH of the application mixture in the absence of glufosinate and ALS or AHAS resistance ; or dicamba , any buffering provided by other components of the appli - 30 glyphosate , glufosinate and ALS or AHAS resistance . cation mixture . In some embodiments , the plants can additionally include In various embodiments of the described methods of other herbicide , insect and disease resistance traits, as well controlling the growth of auxin - susceptible plants wherein as combinations of those traits . For instance, the plants can the application mixture comprises a non -auxin herbicide , the have dicamba , 2, 4 -D , or fluoroxypyr resistant traits . combining step does not comprise separately introducing a 35 pH - lowering agent with the source of auxin herbicide ; the K . METHODS OF CONTROLLING OFF -SITE source of non -auxin herbicide ; the source of monocarbox MOVEMENT ylic acid , or monocarboxylate thereof; and water during the preparation of the application mixture ; wherein the pH Another embodiment of the present invention is directed lowering agent is one that is capable of lowering the pH of 40 to a method of controlling off - site movement of an auxin the application mixture in the absence of any buffering herbicide by contacting the auxin herbicide with a volatility provided by other components of the application mixture . lowering effective amount of a monocarboxylic acid , or a In the described methods, the application mixture is monocarboxylate thereof, prior to application of the auxin applied to the auxin -susceptible plants at an application rate herbicide . sufficient to give a commercially acceptable rate of weed 45 In one embodiment, the method comprises the steps of: control. The appropriate application rate for the application (a ) preparing an aqueous herbicidal application mixture mixture can be readily determined by one of skill in the art comprising an auxin herbicide ; a monocarboxylic acid , and is usually expressed as amount of auxin herbicide per or a monocarboxylate thereof; water ; and , optionally , a unit area treated , e . g . , grams acid equivalent per hectare ( g source of non - auxin herbicide ; and a . e ./ ha ) . Depending on the plant species and growing con - 50 (b ) applying a herbicidally effective amount of the appli ditions , the period of time required to achieve a commer cation mixture to auxin -susceptible plants ; cially acceptable rate of weed control can be as short as a wherein the application mixture satisfies one or more of week or as long as three weeks , four weeks , or one month . the following conditions : Typically , a period of about two to three weeks is needed for the molar ratio of monocarboxylic acid , or monocarboxy the auxin herbicide to exert its full effect. 55 late thereof, to auxin herbicide is from about 1 : 10 to The timing of application can vary . The application mix about 10 : 1 ; ture can be applied , for example , pre- planting of the crop the acid equivalent weight ratio of monocarboxylic acid , plant, such as from about two to about three weeks before or monocarboxylate thereof, to auxin herbicide is from planting auxin - susceptible crop plants or crop plants not about 1 : 10 to about 5 : 1 ; having a auxin herbicide - resistant trait . Crop plants that are 60 the application mixture contains an amount ( acid equiva not susceptible to certain auxin herbicides ( such as corn or lent weight) of the monocarboxylic acid , or monocar plants having an auxin herbicide -resistant trait ) , however , boxylate thereof, from about 0 .01 % to about 25 by generally have no pre - planting restriction and the applica weight of the application mixture ; tion mixture can be applied immediately before planting the concentration of the monocarboxylic acid , or mono such crops . 65 carboxylate thereof, is from about 1 gram ( acid equiva The auxin - susceptible plants can be weeds or crop plants . lent weight) / L to about 250 grams ( acid equivalent Crop plants include, for example , vegetable crops, grain weight) /L ; and US 10 ,212 ,933 B2 33 34 the application mixture comprises an amount of the combined , such as where a monocarboxylic acid salt is monocarboxylic acid , or monocarboxylate thereof, suf- formed in situ by combining a monocarboxylic acid with a ficient to reduce the concentration of volatilized auxin neutralizing base . herbicide in the vapor phase surrounding the applica tion mixture by at least about 10 % relative to the 5 concentration of volatilized auxin herbicide in the Example 1 - A : Tank Mix Compositions vapor phase surrounding an otherwise identical appli (Dicamba + Glyphosate ) cation mixture lacking the monocarboxylic acid , or monocarboxylate thereof. Unless otherwise specified , the herbicidal tank mix com In one aspect, the application mixture contains an amount 10 positions disclosed in Examples 1 - A , 1 - B , and 1 - C were (acid equivalent weight ) of the monocarboxylic acid . or prepared using CLARITY® (DGA dicamba from BASF ) . monocarboxylate thereof, from about 0 . 1 % to about 25 % , by ROUNDUP POWERMAX® (potassium glyphosate from weight of the application mixture . Monsanto ), BANVEL® (DMA dicamba from BASF ), DURANGO® DMAB (DMA glyphosate from Dow Agro L . METHODS OF COUNSELING ON USE OF Sciences ) , LIBERTY® (ammonium glufosinate from Bayer AN AUXIN HERBICIDE CropScience ), and /or 2 , 4 - D amine ( Albaugh ) by succes sively adding each specified herbicide to water and mixing . Another embodiment of the present invention is directed Those tank mix formulations containing additional tank mix to methods of counseling an individual regarding the prepa - 2. adjuvants such as potassium acetate (Sigma ) , dipotassium ration and /or application of an auxin herbicide . phosphate ( ICL ) , and /or ammonium sulfate (Sigma ) were In one embodiment, the invention is directed to a method typically prepared by adding aqueous stock solutions of the of counseling an individual on the application of an auxin adjuvants to the herbicide mixture . herbicide to auxin -susceptible plants , the method compris- Herbicide salts not purchased from a commercial vendor, ing : 25 such as IPA glyphosate and MEA dicamba , typically were (a ) identifying a source of an auxin herbicide; prepared by mixing the herbicide acid with the desired ( b ) instructing the individual to prepare an aqueous her - amine. The herbicide acid to amine ratio typically is about bicidal composition application mixture from the 1 :1 . In certain instances, a slight excess of amine is desired . source of auxin herbicide; and As used in these examples, DGA refers to diglycolamine ; ( c ) additionally instructing the individual to supplement 30 DMA refers to dimethylamine ; IPA refers to isopropylam the application mixture with a monocarboxylic acid , or ine ; and MEA refers to monoethanolamine . monocarboxylate thereof, prior to the application of the application mixture to auxin -susceptible plants . Herbicidal tank mix compositions prepared by themethod In another embodiment , the invention is directed to a described above are listed in Tables 1 - 1 through 1 - 15 below : method of counseling an individual on the application of an 35 auxin herbicide to auxin - susceptible plants , the method TABLE 1 - 1 comprising: ( Composition 854 - B ) ( a ) identifying a source of an auxin herbicide ; ( b ) identifying a source of a monocarboxylic acid , or a 40 INGREDIENT WT (g ) WT % % ACTIVE monocarboxylate thereof; and (c ) instructing the individual to prepare an aqueous her - DGA dicamba (CLARITY ® 30 . 00 3 . 00 % 1. 20 % ae bicidal composition application mixture from the ROUNDUP POWERMAX® 60 .60 6 . 06 % 2 . 40 % ae source of auxin herbicide and the source of monocar water 909. 78 boxylic acid , or monocarboxylate thereof, for applica - 45 — tion to the auxin - susceptible plants . The source of monocarboxylic acid , or a monocarboxy late thereof, can be , for example , a single source such as the TABLE 1 -2 herbicidal composition adjuvant previously discussed , or (Composition 854- C ) even a source that provides for in situ formation of the 50 monocarboxylic acid , or monocarboxylate thereof, in the INGREDIENT WT ( g ) WT % % ACTIVE herbicidal composition application mixture . DGA dicamba (CLARITY ® ) 30 .03 3 .00 % 1 . 20 % ae Having described the invention in detail, it will be appar ROUNDUP POWERMAX ® 60 . 34 6 . 03 % 2 . 40 % ae ent that modifications and variations are possible without dipotassium phosphate (50 % ) 40 .02 4 .00 % 2 . 00 % departing from the scope of the invention defined in the 55 water* 869. 74 appended claims. M . EXAMPLES TABLE 1 - 3 The following non - limiting examples are provided to 60 — (Composition 854 - F ) further illustrate the present invention . It should be noted that the composition examples below are presented on the INGREDIENT WT (g ) WT % % ACTIVE basis of the components initially combined to form the DGA dicamba ( CLARITY ® ) 7 . 50 3 .00 % 1 . 20 % ae ROUNDUP POWERMAX ® 15 . 14 6 .06 % 2 . 40 % ae reported tank mix or concentrate . The various embodiments potassium acetate of the present invention are intended to encompass such 65 Water 5 . 04 2 .01 % 2 .01 % initial compositions as well as any corresponding composi 222 . 42 tions resulting from interaction among the components once US 10 ,212 ,933 B2 35 36 TABLE 1 -4 TABLE 1 - 10 (Composition 751- E ) ( Composition 870 - D ) INGREDIENT WT (g ) WT % % ACTIVE INGREDIENT WT (g ) WT % % ACTIVE 5 IPA glyphosate (30 .8 % ) 19 . 54 7 . 82 2 . 40 % ae DGA dicamba (CLARITY ® ) 7 .51 3 .00 % 1. 20 % ae 2 , 4 - D amine 15 . 42 6 . 17 2 . 40 % ae ROUNDUP POWERMAX ® 15 . 16 6 .06 % 2 . 40 % ae water 215 . 04 ammonium sulfate (AMS ) 7 . 35 2 . 94 % 1 . 00 % water 220 .07 10 TABLE 1 - 11 (Composition 563 - 2) TABLE 1 - 5 INGREDIENT WT (g ) WT % % ACTIVE ( Composition 751 -D ) 15 BANVEL ® 7 . 34 2 . 94 % 1 . 20 % ae INGREDIENT WT (g ) WT % % ACTIVE ROUNDUP POWERMAX ® 15 .00 6 . 00 % 2 . 40 % ae water 227 .66 DGA dicamba ( CLARITY ® ) 7 . 49 3 . 00 % 1 . 20 % ae ROUNDUP POWERMAX ® 15 . 10 6 . 06 % 2 . 40 % ae potassium acetate (50 % ) 10 . 00 4 . 00 % 2 . 00 % ammonium sulfate (34 % ) 7 . 34 2 . 94 % 1 . 00 % 20 water 210 .07 TABLE 1 - 12 (Composition 563 -5 ) INGREDIENT WT (g ) WT % % ACTIVE TABLE 1 - 6 25 BANVEL ® 7 . 34 2 . 94 % 1 . 20 % ae (Composition 210 - D ) ROUNDUP POWERMAX ® 15 .07 6 . 00 % 2 . 40 % ae potassium acetate (50 % ) 10 .05 4 .00 % 2 .00 % INGREDIENT WT (g ) WT % % ACTIVE water 217 .65 DGA dicamba (CLARITY ® ) 7 . 48 3 .00 % 1 . 20 % ae ROUNDUP POWERMAX ® 14 . 99 6 . 00 % 2 . 40 % ae 30 1 : 1 wt/ wt 50 % potassium acetate/ 10 . 00 4 . 00 % 2 .00 % 50 % dipotassium phosphate TABLE 1 - 13 water 217. 42 (Composition 563 - 1 ) 35 INGREDIENT WT ( g ) WT % % ACTIVE TABLE 1 -7 MEA dicamba (62 . 2 % ) 4 . 81 1 . 93 % 1 . 20 % ae ROUNDUP POWERMAX ® 15 . 00 6 . 00 % 2 . 40 % ae (Composition 870 - A ) water 230 . 18 INGREDIENT WT ( g ) WT % % ACTIVE - 40 DMA glyphosate 15 .04 6 . 02 % 2 . 40 % ae ( DURANGO ® DMA ® ) TABLE 1 - 14 2 , 4 - D amine 15 . 50 6 . 20 % 2 . 40 % ae Composition 563 - 4 ) water 219 .54 INGREDIENT WT ( g ) WT % % ACTIVE 45 MEA dicamba (62 . 2 % ) 4 . 85 1 . 93 % 1 . 20 % ae TABLE 1 - 8 ROUNDUP POWERMAX ® 14 . 96 6 . 00 2 . 40 % ae potassium acetate (50 % ) 10 .03 4 . 00 % 2 % Composition 870 - B ) water 220 . 18 INGREDIENT WT (g ) WT % % ACTIVE 50 DMA glyphosate 15 .04 6 .02 % 2 . 40 % ae ( DURANGO ® DMA ® ) TABLE 1 - 15 2 , 4 - D amine 15 .43 6 . 17 % 2 . 40 % ae ( Composition 836 - 1 ) potassium acetate (50 % ) 10 .02 4 . 00 % 2 . 00 % water 209 . 57 55 INGREDIENT WT ( g ) WT % % ACTIVE CLARITY ® 6 .01 3 . 0 1 . 2 % ae ROUNDUP POWERMAX ® 12 .05 6 . 1 2 . 4 % ae TABLE 1 - 9 water 181. 98 (Composition 870 - C ) 60 For the tank mix compositions in Table 1 - 16 through INGREDIENT WT ( g ) WT % % ACTIVE Table 1 - 19 , the monocarboxylic acid salt (e . g ., potassium IPA glyphosate (30 . 8 % ae ) 19 . 54 7 .82 % 2 . 40 % ae acetate ) was formed in situ by combining a monocarboxylic 2 , 4 - D amine 15 .42 6 . 17 % 2 . 40 % ae potassium acetate (50 % ) 10 . 00 4 . 00 % 2 . 00 % acid with a neutralizing base . The compositions were pre 205 . 04 65 pared by mixing the herbicide ( s) with water followed by water addition of the monocarboxylic acid followed by addition of the neutralizing base . Although a specific order of addition US 10 ,212 , 933 B2 37 38 of the ingredients is not required to prepare the final com TABLE 1 -21 position , the order of addition described above can be advantageous to reduce the heat generation resulting when the ingredients are combined . The neutralizing base (potas (Composition 893- A ) sium hydroxide in the compositions below ) was added as a 5 45 % w / w aqueous solution . INGREDIENT WT ( g ) WT % % ACTIVE

TABLE 1 - 16 CLARITY ® 7. 50 .3 ) . . 0 1. 2 % ae ROUNDUP POWERMAX ® 15 . 20 6 . 0 2 . 4 % ae 10 (Composition 836 - 2 ) water 227 .46

INGREDIENT WT ( g ) WT % % ACTIVE TABLE 1 - 22 CLARITY ® 6 . 00 3 . 0 1 . 2 % ae 15 ROUNDUP POWERMAX ® 12 .04 6 . 0 2 . 4 % ae (Composition 893- B ) succinic acid 2 . 57 1. 3 potassium hydroxide (45 % solution ) 5 . 46 INGREDIENT WT ( g ) WT % % ACTIVE water 174 .01 20 CLARITY ® 7 . 50 3 . 0 1 . 2 % ae ROUNDUP POWERMAX ® 15 .04 6 . 0 2 . 4 % ae potassium acetate (50 % solution ) 10 . 04 2 . 0 % ai TABLE 1 - 17 water 217 . 44 25 ( Composition 836 - 3 ) INGREDIENT WT ( g ) WT % % ACTIVE TABLE 1 - 23 CLARITY ? 6 . 00 3 . 0 1 . 2 % ae ROUNDUP POWERMAX ® 12 .09 6 . 0 2 . 4 % ae ( Composition 893- C ) propionic acid 1 .63 0 . 8 30 - potassium hydroxide (45 % solution ) 2. 72 INGREDIENT WT ( g ) WT % % ACTIVE water 177 . 65 CLARITY ® 7 .67 3 . 0 1 . 2 % ae ROUNDUP POWERMAX ® 15 .02 6 . 0 2 . 4 % ae potassium formate 5 .05 2 . 0 % ai TABLE 1 - 18 35 water 222 . 46 (Composition 836 - 4 ) INGREDIENT WT ( g ) WT % % ACTIVE TABLE 1 - 24 CLARITY ® 6 .01 3 . 0 1 . 2 % ae 40 Composition 893 - D ) ROUNDUP POWERMAX ® 12 . 03 6 . 0 2 . 4 % ae acetic acid 1 . 32 0 . 7 INGREDIENT WT ( g ) WT % % ACTIVE potassium hydroxide (45 % solution ) 2 .73 water 177 . 98 CLARITY ® 7 . 51 3 . 0 1 . 2 % ae ROUNDUP POWERMAX® 15 . 03 6 . 0 2 . 4 % ae 45 potassium benzoate 5 . 05 2 . 0 % ai water 222 .45 TABLE 1 - 19 (Composition 836 - 5 ) TABLE 1 - 25 INGREDIENT WT ( g ) WT % % ACTIVE 50 - ( Composition 893 - F ) CLARITY ® 6 .05 3 . 0 1 . 2 % ae ROUNDUP POWERMAX ® 12 .03 6 . 0 2 . 4 % ae INGREDIENT WT ( g ) WT % % ACTIVE formic acid 1 . 00 0 .5 potassium hydroxide (45 % solution ) 2 . 73 CLARITY ® 7 .51 3 . 0 1 . 2 % ae Water 178 . 32 ROUNDUP POWERMAX ® 15 .04 6 . 0 2 . 4 % ae 5 sodium acetate 5 .01 2 . 0 % ai water 222 .44 TABLE 1 - 20 (Composition 836 - 6 ) 60 TABLE 1 - 26 INGREDIENT WT (g ) WT % % ACTIVE ( Composition 854 - A ) CLARITY ® 6 .01 3 . 0 1 . 2 % ae ROUNDUP POWERMAX ® 12. 03 6 . 0 2 . 4 % ae INGREDIENT WT ( g) WT % % ACTIVE potassium hydroxide (45 % solution ) 1 . 78 0 . 9 CLARITY ® 30 .0 3. 0 1 . 2 % ae water 180 . 19 65 water US 10 ,212 , 933 B2 39 40 TABLE 1 - 27 TABLE 1 - 33 (Composition 854 - D ) Composition 268 - 5 ) INGREDIENT WT ( g ) WT % % ACTIVE INGREDIENT WT ( g ) WT % % ACTIVE CLARITY ® 7 . 5 3 . 0 1 . 2 ae DGA dicamba ( CLARITY ® ) 6 .09 3 .05 | 1 .20 ae ROUNDUP POWERMAX ® 15 . 08 6 .0 2 . 4 ae ammonium glyphosate (ROUNDUP ® 7 .07 3 .53 2 . 40 ae potassium oxalate (25 % solution ) 20 .0 8 . 0 2 . 0 ai ENERGY ) water 207 .42 potassium acetate 8 .02 4 .00 2 . 00 dipotassium phosphate 9 .08 4 .56 3 . 00 10 water 169. 69 84 .86 TABLE 1 - 28 Composition 854 - E ) TABLE 1 - 34 INGREDIENT WT ( g) WT % % ACTIVE 15 (Composition 268- 6 ) CLARITY ® 7 . 5 3 . 0 1 . 2 ae INGREDIENT WT (g ) WT % % ACTIVE ROUNDUP POWERMAX ® 15 .08 6 . 0 2 . 4 ae potassium citrate (50 % ) 10 . 0 4 . 0 DGA dicamba ( CLARITY ® ) 6 . 11 3 .05 1 . 20 ae water 217 .42 ROUNDUP POWERMAX ® 12 . 00 6 . 00 2 . 40 ae 20 water 181 . 90 90 . 95

TABLE 1 -29 ( Composition 268 - 1 ) Example 1 - B : Tank Mix Compositions 25 (Dicamba + Glufosinate ) INGREDIENT WT ( g ) WT % % ACTIVE DGA dicamba ( CLARITY ® ) 6 .13 3 . 05 1 . 20 ae ammonium glyphosate (ROUNDUP ? 7 . 10 3 .53 2 . 40 ae TABLE 1 - 35 ENERGY) (Composition 364 - 2 ) water 186 .78 93 .422 30 * ROUNDUP ? ENERGY is the glyphosate ammonium salt , sold as water soluble INGREDIENT WT (g ) WT % % ACTIVE granules in Europe . DGA dicamba ( CLARITY ® ) 6 . 04 6 . 04 1 . 2 % ae onium glufosinate (LIBERTY ® ) 7 .59 7 .59 3 . 36 % v / v water 186 .57 186 .57 TABLE 1 -30 35 (Composition 268 - 2 ) INGREDIENT WT (g ) WT % % ACTIVE TABLE 1 - 36 DGA dicamba (CLARITY ® ) 6 . 09 3 . 05 1 . 20 ae Composition 364 - 3 ) ammonium glyphosate (ROUNDUP ® 7 . 09 3 . 53 | 2 . 40 ae 40 ENERGY) INGREDIENT WT (g ) WT % % ACTIVE dipotassium phosphate 9 .12 4 .56 3. 00 water 177 .72 88 . 86 DGA dicamba ( CLARITY ® ) 6 .05 6 . 05 1 . 2 % ae ammonium glufosinate (LIBERTY ® ) 7 .41 7 . 41 3 . 36 % v / v dipotassium phosphate ( 50 % ) 9 .199 . 193 . 00 % v / v 45 water 177. 40 177 . 40 TABLE 1 -31 (Composition 268 -3 ) TABLE 1 -37 INGREDIENT WT ( g ) WT % % ACTIVE 50 (Composition 364 - 5 ) DGA dicamba ( CLARITY ® ) 6 .09 3 .05 1 . 20 ae ammonium glyphosate (ROUNDUP ® 7 . 10 3 . 53 2 . 40 ae INGREDIENT WT % % ACTIVE ENERGY potassium acetate 7 .99 4 .00 4 . 00 DGA dicamba ( CLARITY ® ) 2 . 9 1 . 2 % ae water 178 .78 89 .42 potassium hydroxide 0 . 38 acetic acid 0 . 23 ammonium glufosinate (LIBERTY ® ) 3 . 7 3 . 36 % v / v water 92. 79 TABLE 1 - 32 (Composition 268 - 4 ) TABLE 1 - 38 INGREDIENT WT ( g ) WT % % ACTIVE 60 ( Composition 364 - 6 ) DGA dicamba ( CLARITY ® ) 6 . 25 3 . 05 1 . 20 ae ammonium glyphosate (ROUNDUP ? 7 .09 3. 53 2 .40 ae INGREDIENT WT % % ACTIVE ENERGY ) potassium acetate 8 . 00 16 . 01 4 . 00 DGA dicamba ( CLARITY ® ) 2 . 9 1 . 2 % ae water 170 .81 85 .42 65 potassium hydroxide 0 . 38 acetic acid 0 . 23 US 10 ,212 ,933 B2 41 42 TABLE 1 - 38 - continued above 60° C . The pre - formed potassium acetate was then added to the solution containing the herbicide ( s ) . The ratio (Composition 364 - 6 ) indicated in the tables below is on a molar basis . For example , “ 50 / 50 ACOH /KOH ” means a 1 : 1 M ratio of acetic INGREDIENT WT % % ACTIVE 5 acid to potassium hydroxide . The compositions in the tables ammonium glufosinate (LIBERTY ® ) 3 . 7 3 . 36 % v / v dipotassium phosphate 4 .6 3 . 00 % v / v below were prepared by adding the desired amount of each water 88 .19 ingredient and stirring for about 20 minutes . Alternatively , the monocarboxylic acid salt can be pre 10 pared by adding the monocarboxylic acid to the solution Example 1 - C : Tank Mix Compositions ( Dicamba ) containing the herbicide ( s ) followed by addition of a neu tralizing base . Although a specific order of addition of the ingredients is not required to prepare the final composition , TABLE 1 - 39 the order of addition described above can be advantageous 15 to reduce the heat generation resulting when the ingredients (Composition 364 - 1 ) are combined . INGREDIENT WT ( g ) WT % % ACTIVE DGA dicamba ( CLARITY ® ) 6 .00 6 .00 1 . 20 % ae TABLE 2A - 1 - 29 water 194 .00 194 . 00 20 ( Composition 503- 1)

TABLE 1 - 40 INGREDIENT WT (g ) WT % % ACTIVE (Composition 364 - 4 ) - 25 CLARITY ® 157 . 4 78. 7 31. 0 INGREDIENT WT % % ACTIVE 50 /50 ACOH /KOH 4 2 . 6 21. 3 6 .9 (ACOH ) DGA dicamba (CLARITY ® ) 2 . 9 1 . 2 % ae potassium hydroxide 0 . 38 acetic acid 0 . 23 TABLE 2A - 1 - 30 water 96 . 45 30 ( Composition 503 - 3 ) The compositions shown in Tables 1 -37 , 1 -38 , and 1 -40 INGREDIENT WT ( g ) WT % % ACTIVE above (Compositions 364 -5 , 364 - 6 , and 364 - 4 , respectively ) CLARITY ® 157. 4 78 . 7 31. 0 were prepared by combining the appropriate amount of the 35 60 / 40 ACOH / KOH 42. 6 321 . 8 . 2 ( ACOH ) composition shown in Table 2 -17 below (Composition 871 5 ) with the additional components and an amount of water sufficient to provide a final dicamba concentration of 1 . 2 % ae . TABLE 2A - 1 - 31 Example 1- D : Acetic Acid Adjuvant 40 Composition 295 - 3 ) INGREDIENT WT ( g ) WT % % ACTIVE An example of an acetic acid adjuvant for use in the DGA dicamba (55 . 2 % ) 112 . 3 56 . 2 31. 0 preparation of a dicamba tank mix is described in Table 1 -41 60 / 40 ACOH / KOH 65 . 1 32 . 6 12 . 6 ( ACOH ) below . 45 water 22 . 6 11 . 3 TABLE 1 -41 Adjuvant (Composition 828 - 2 ) TABLE 2A - 1 - 32 INGREDIENT WT (g ) WT % 50 (Composition 295 - 6 ) potassium acetate 25 .04 25 . 0 INGREDIENT WT (g ) WT % % ACTIVE potassium citrate (monohydrate ) 24 . 98 25 . 0 water 50 .02 50 . 0 DGA dicamba (55 . 2 % ) 112 . 3 56 . 2 31 . 0 60 / 40 ACOH / KOH 86 . 8 43 . 4 16 . 8 ( ACOH ) 0 . 9 0 . 4 total 100 . 04 100 . 0 55 water

Example 2 - A : Liquid Concentrate Compositions TABLE 2A - 1 - 33 (Dicamba ) 60 (Composition 771- C ) Liquid concentrate compositions are described in INGREDIENT Examples 2 - A , 2 - B , 2 - C , and 2 - D . WT ( g ) WT % % ACTIVE The potassium acetate used in the compositions in Tables CLARITY ® 29 . 15 62 . 94 acetic acid 6 . 26 6 . 26 2A - 1 -29 through Table 2A - 1 -32 was prepared by adding the potassium hydroxide 8 . 72 8 . 72 desired amount of glacial acetic acid to the desired amount 65 water 2 . 19 2 . 19 of potassium hydroxide ( 45 % w / w solution ) in an ice bath without allowing the temperature of the solution to rise US 10 ,212 , 933 B2 43 44 TABLE 2A - 1 -34 TABLE 2 - 3 (Composition 210 - F ) ( Composition 761- B ) 5 INGREDIENT WT ( g ) WT % % ACTIVE INGREDIENT WT ( g ) WT % % ACTIVE DGA dicamba /MEA glyphosate premix 23 .48 9 . 39 % 2 .40 % ae 1 : 1 wt/ wt 50 % potassium acetate / 50 % 10 .04 4 . 00 % 2 .00 % CLARITY® 32 . 82 71 . 20 dipotassium phosphate acetic acid 4 . 48 9 .72 Water 216 .51 10 potassium hydroxide 6 .24 13. 53 water 2 .56 TABLE 2 - 4 (Composition 210 - E ) 15 Example 2 - B : Liquid Concentrate Compositions INGREDIENT WT ( g ) WT % % ACTIVE (Dicamba + Glyphosate ) DGA dicamba ( CLARITY ® ) 32 . 2 32 . 12 12 . 75 1. 35 MEA glyphosate (46 . 8 % ) 55 . 0 54 . 49 25 . 50 AGM 550 2 .50 2 . 50 Herbicidal compositions containing DGA dicambaDa allland 20 Agnique PG8107 - G 5 . 1 5 .00 MEA glyphosate were prepared by mixing CLARITY® SAG 1572 0 .02 0 .01 with MEA glyphosate with water . After stirring the mixture Ferric citrate ( 7 . 0 % Fe ) 0 . 33 0 . 31 0 . 02 % for five minutes, surfactants AGM550 and Agnique 50 % K acetate solution 5 . 7 5 . 7 PG8107 - G were added followed by ferric citrate (for miti gating necrosis in certain crops ) and anti -foaming agent 25 The potassium acetate used in the formulations in Tables SAG 1572 , and the mixture stirred for an additional 30 2 - 5 through Table 2 -13 was prepared by adding the desired minutes. Premix compositions which also contain additional amount of glacial acetic acid to the desired amount of adjuvants , such as potassium acetate , were prepared as potassium hydroxide (45 % w /w solution ) in an ice bath described above with the modification of replacing the water without allowing the temperature of the solution to rise with the desired amount of aqueous adjuvant. The MEA 30 above 60° C . The ratio indicated in the tables below is on a glyphosate salt used in the preparation of the compositions molar basis . For example “ 50 /50 ACOH /KOH ” means a 1: 1 was prepared by mixing glyphosate acid and 1 . 35 molar M ratio of acetic acid to potassium hydroxide. The compo equivalents ofMEA with water. The list of ingredients of the sitions in the tables below were prepared by adding the dicamba/ glyphosate premix composition is set forth in Table desired amount of each ingredient and stirring for about 20 2 - 1 . minutes . Alternatively , the monocarboxylic acid salt can be prepared by adding themonocarboxylic acid to the solution TABLE 2 - 1 containing the herbicide ( s ) followed by addition of a neu tralizing base . (DGA Dicamba /MEA Glyphosate Premix ) - 40 The Fe dopant in Tables 2 -8 through 2 - 13 ( added to INGREDIENT WT (g ) WT % % ACTIVE mitigate necrosis in certain crops) was prepared by mixing ferric sulfate and citric acid . DGA dicamba ( CLARITY ® ) 32 . 36 32 . 36 % 12 .75 % 1 .35 MEA glyphosate (46 . 9 % ) 54 . 37 54 . 37 % 25 . 50 % TABLE 2 - 5 AGM 550 2 . 50 2 . 50 % 45 Ag PG8107 - G 5 .00 5 . 00 % ( Composition 287 - 5 ) SAG 1572 0 . 01 0 .01 % INGREDIENT WT (g ) WT % % ACTIVE Ferric citrate (7 .0 % Fe ) 0 . 31 0 .31 % 0 . 02 % water 5 . 44 5 .44 % DGA dicamba (54 . 8 % ae ) 18 .25 18 .25 10 . 0 50 1 . 35 MEA glyphosate (46 . 9 % ae ) 42 .74 42 . 74 20 . 0 SAG 1572 0 . 01 0 . 01 Ferric Citrate ( 7 . 0 % Fe) 0 . 31 0 . 31 0 . 02 Dicamba/ glyphosate premixes containing additional adju 60 / 40 ACOH / KOH ( 38 . 7 ACOH ) 6 . 98 6 . 98 2 . 70 vants , such as potassium acetate, typically were prepared by water 31. 72 31 .72 adding the desired amount of an aqueous solution of the adjuvant to the premix prepared as described in Tables 2 - 2 55 and 2 - 3 below . TABLE 2 - 6 TABLE 2 -2 (Composition 287 -6 ). ( Composition 751 - F ) - 606 INGREDIENT WT ( g ) WT % % ACTIVE DGA dicamba (54 . 8 % ae ) 17 . 34 17 . 34 9 . 50 INGREDIENT WT ( g ) WT % % ACTIVE 1 . 35 MEA glyphosate (46 . 9 % ae ) 40 .60 40 .60 19 .00 DGA dicamba /MEA glyphosate premix 23 .51 9 . 40 % 1 . 20 % ae SAG 1572 0 . 01 0 .01 potassium acetate (50 % ) 10 . 00 4 .00 % 2 .00 % Ferric Citrate ( 7 . 0 % Fe ) 0 . 31 0 . 31 0 .02 water 216 . 48 60 / 40 ACOH /KOH ( 38 . 7 ACOH ) 13 . 44 13. 44 5 . 20 65 Water 28 . 30 28 . 30 US 10 ,212 ,933 B2 45 46 TABLE 2 -7 TABLE 2 - 12 (Composition 512 - 1 ) ( Composition 249 - 2 ) INGREDIENT WT ( g ) WT % % ACTIVE 5 INGREDIENT WT (g ) WT % % ACTIVE DGA dicamba (CLARITY ® ) 31 .61 31. 61 12 . 55 1 .35 MEA glyphosate ( 46 . 9 % ae ) 53 . 63 53. 63 25 . 10 DGA dicamba (55 . 2 % ) 18 .04 18 . 04 9 .95 AGM 550 2 . 50 2 . 50 1 . 35 MEA glyphosate (46 . 8 % ae ) 42 .50 42. 50 19 .90 AGNIQUE PG8107 - 6 5 . 00 5 . 00 AGM 550 2 .50 2 . 50 SAG 1572 0 . 01 0 . 01 10 Agnique PG8107 - G 2 .00 2 .00 Ferric Citrate (7 . 0 % Fe ) 0 . 31 0 . 31 0 .02 SAG 1572 0 .01 0 .01 70 / 30 ACOH / KOH ( 38 . 7 AcOH ) 6 .93 6 . 93 Fe Dopant ( 4 .5 % Fe ) 0 . 49 0 .49 0 .02 60 /40 ACOH /KOH (38 . 7 ACOH ) 10 . 83 10 .83 4 . 20 15 water 23 .59 23. 59 TABLE 2 - 8 (Composition 248 - 1 ) TABLE 2 - 13 INGREDIENT WT (g ) WT % % ACTIVE 20 (Composition 249 - 3 ) DGA dicamba (55 . 2 % ) 18 . 03 18 . 03 9 . 95 1 . 35 MEA glyphosate (46 . 8 % ae ) 45 .51 45 . 51 19 . 90 INGREDIENT WT (g ) WT % % ACTIVE Ethoquad C12 75 DEG 3 . 49 3 . 49 SAG 1572 0 .01 0 . 01 DGA dicamba (55 . 2 % ) 17 .93 17 . 93 9 . 90 Fe Dopant ( 4 . 5 % Fe ) 0 . 49 0 . 49 0 . 02 1 . 35 MEA glyphosate ( 46 . 8 % ae ) 42. 37 42. 37 19 . 80 60 /40 ACOH /KOH ( 38 . 7 ACOH ) 6 . 95 6 . 95 2 . 70 AGM 550 2 . 50 2 . 50 water 28 . 49 28 . 49 25 Agnique PG8107 - G 1 . 97 1 . 97 SAG 1572 0 .01 0 .01 Fe Dopant ( 4 . 5 % Fe ) 0 . 49 0 .49 0 . 02 60 / 40 ACOH /KOH ( 38 . 7 AcOH ) 14 . 00 14 . 00 5 . 40 TABLE 2 - 9 water 20 . 79 20 . 79 (Composition 248 - 2 ) 30 INGREDIENT WT (g ) WT % % ACTIVE TABLE 2 - 14 DGA dicamba (55 . 2 % ) 18 . 08 18 .08 9 . 95 ( Composition 530 - 2 ) 1 . 35 MEA glyphosate (46 . 8 % ae ) 42 .62 42 . 62 19 . 90 Ethoquad C12 75 DEG 3 . 49 3 . 49 35 INGREDIENT WT ( g ) WT % % ACTIVE SAG 1572 0 . 02 0 . 02 Fe Dopant ( 4 . 5 % Fe ) 0 . 49 0 . 49 0 . 02 CLARITY ® 125 .63 25 . 13 9 . 90 ae 60 /40 ACOH /KOH ( 38 . 7 AcOH ) 10 . 86 10 . 86 4 . 20 1 . 35 MEA glyphosate ( 46 . 8 % ae ) 211 . 54 42 . 31 19 . 80 ae Water 24 .61 24 .61 AGM 550 12 . 50 2 . 50 Agnique PG8107 - G 10 .00 2 .00 40 SAG 1572 0 .05 0 .01 Fe Dopant ( 4 . 5 % Fe ) 1 . 94 0 . 39 0 .02 65 / 35 AcOH / KOH ( 38 . 7 AcOH ) 64 . 29 12 .86 5 . 40 TABLE 2 - 10 water 199 .68 (Composition 248 - 3 ) INGREDIENT WT ( g ) WT % % ACTIVE 45 TABLE 2 - 15 DGA dicamba (55 . 2 % ) 17 .91 17 . 91 9 . 90 1 . 35 MEA glyphosate (46 . 8 % ae ) 42 . 28 42 . 28 19 . 80 ( Composition 540 -1 ) Ethoquad C12 75 DEG 3 .61 3 .61 SAG 1572 0 .02 0 .02 INGREDIENT WT ( g ) WT % % ACTIVE Fe Dopant ( 4 . 5 % Fe ) 0 . 53 0 . 53 0 .02 50 60 /40 ACOH /KOH (38 . 7 AcOH ) 13 . 95 13. 95 5 . 40 CLARITY ® ( 39 . 4 % a. e .) 124 . 37 24 . 87 9 . 80 ae water 21 . 81 21. 81 1 . 35 MEA glyphosate (46 . 8 % ae ) 209 . 40 41. 88 | 19. 60 ae Ethoquad C12 75 DEG 17 . 50 3 . 50 65 / 35 ACOH /KOH ( 42 . 0 % ACOH ) 64 . 29 12 . 86 5 . 40 Fe Dopant ( 4 . 5 % Fe ) 1 . 94 0 . 39 0 .0175 TABLE 2 - 11 55 SASAG 1572 0 .05 0 .01 water 82. 45 16 . 49 (Composition 249 - 1) INGREDIENT WT ( g ) WT % % ACTIVE TABLE 2 - 16 DGA dicamba (55 . 2 % ) 18 .00 18. 00 9 .95 1 .35 MEA glyphosate (46 . 8 % ae ) 42 . 52 42. 52 19 . 90 60 ( Composition 540 - 4 ) AGM 550 2 . 48 2 .48 Agnique PG8107- G 1 . 95 1 . 95 INGREDIENT WT ( g ) WT % % ACTIVE SAG 1572 0 . 01 0 . 01 Fe Dopant ( 4 . 5 % Fe ) 0 .60 0 . 60 0 .02 CLARITY ® (39 . 4 % a . . ) 123 . 10 24 .62 9 . 70 ae 60 /40 ACOH / KOH (38 . 7 AcOH ) 6 . 96 6 . 96 2 . 70 1 . 35 MEA glyphosate ( 46 . 8 % ae ) 207 . 26 41. 45 19 . 40 ae water 27 . 48 27 . 48 AGM 550 12 . 50 2 .50 Agnique PG8107 - G 10 .00 2 .00 US 10 ,212 , 933 B2 47 48 TABLE 2 - 16 -continued TABLE 2 -21 - continued (Composition 540 - 4 ) ( Composition 771 -3 ) INGREDIENT WT ( g ) WT % % ACTIVE SAG 1572 0 . 05 0 . 01 INGREDIENT WT ( g ) WT % % ACTIVE Fe Dopant ( 4 . 5 % Fe ) 1 . 94 0 . 39 0 .0175 60 /40 ACOH /KOH ( 38 . 7 % AcOH ) 69 . 77 13 .95 5 . 40 acetic acid 13 .52 Phosphate ester 5 .00 1 . 000 acetic acid 13. 52 13. 52 water water 70 .38 14 .08 10 3 .55 3 . 55

Example 2 - C : Liquid Concentrate Compositions TABLE 2 - 22 ( Dicamba ) 15 (Composition 871 - 2)

TABLE 2 - 17 INGREDIENT WT ( g ) WT % % ACTIVE 73 . 43 73 . 43 29 . 00 (Composition 871- 5 ) 20 DGA dicamba ( CLARITY ® ) potassium hydroxide 9 . 50 9 . 50 INGREDIENT WT (g ) WT % % ACTIVE acetic acid 5 . 91 5 . 91 DGA dicamba (CLARITY ® ) 73 . 43 73 . 43 29 . 00 PF 8000 Surfactant 1 . 00 1 .00 potassium hydroxide 9 . 50 9 . 50 water 10 . 16 10 . 16 acetic acid 5 .91 5 . 91 water 11 . 16 11. 16 25 TABLE 2 - 23 TABLE 2 - 18 Composition 871 - 3 ) 30 (Composition 871 - 4 ) INGREDIENT WT ( g ) WT % % ACTIVE INGREDIENT WT (g ) WT % % ACTIVE DGA dicamba (CLARITY ® ) 73 .07 73 .07 28 .86 potassium hydroxide 11. 00 11 . 00 DGA dicamba ( CLARITY ® ) 73 . 49 73. 49 29 .03 acetic acid 5 . 88 5 .88 potassium hydroxide 9 .00 9 .00 1 . 00 1 . 00 5 . 93 PF 8000 Surfactant acetic acid 5 .93 35 water 9 . 05 9 .05 water 11 . 58 11 . 58

TABLE 2 - 19 TABLE 2 - 24 40 (Composition 871- 12) (Composition 871- 6 ) INGREDIENT WT (8 ) WT % % ACTIVE INGREDIENT WT ( g ) WT % % ACTIVE DGA dicamba ( CLARITY ® ) 73 . 07 73 .07 28 . 86 DGA dicamba (CLARITY ® ) 72 .53 72 .53 28 .65 potassium hydroxide 5 . 88 5 . 88 potassium hydroxide 13 . 25 13 . 25 acetic acid 11 . 00 11. 00 acetic acid 7 . 65 7 .65 10 .05 10 .05 water 6 . 57 6 . 57 water

TABLE 2 -20 50 Example 2 - D : Liquid Concentrate Compositions (Composition ion 761 - 2) (Dicamba + Glyphosate ) INGREDIENT WT ( g ) WT % % ACTIVE TABLE 2 - 24 DGA dicamba (CLARITY ® ) 72 .47 72 .47 28 .63 55 - potassium hydroxide 13 . 53 13 . 53 (Composition 540 - 1 ) acetic acid 9 .72 9 .72 water 4 . 28 4 . 28 INGREDIENT WT (g ) WT % % ACTIVE CLARITY ® ( 39 . 4 % ae ) 24 . 87 24 . 87 9 . 8 1 . 35 MEA glyphosate (45 . 6 % ae ) 42 . 98 42. 98 19 . 6 TABLE 2 - 21 hl Ethoquad C12 75 DEG 3 . 5 3 . 5 SAG 1572 0 .01 0 .01 (Composition 771 - 3) Ferric sulfate 0 . 14 0 . 14 Citric Acid 0 . 26 0 . 26 INGREDIENT WT (g ) WT % % ACTIVE Acetic acid 5 .32 5 . 32 potassium hydroxide ( 45 % solution ) 7 . 33 7 . 33 DGA dicamba (CLARITY ® ) 64 . 11 64 . 11 25 . 32 hs water 15 .59 15 . 59 potassium hydroxide 18 . 82 18 . 82 US 10 ,212 , 933 B2 49 50 TABLE 2 -25 TABLE 2 - 29 Composition 249 - 3 ) (Composition 085 -1 ) INGREDIENT WT (g ) WT % % ACTIVE INGREDIENT WT (g ) WT % % ACTIVE DGA dicamba (55 . 2 % ae ) 17 . 93 9 . 90 1 . 35 MEA glyphosate (46 . 8 % ae ) 42. 31 19 . 80 AGM 550 2 . 50 CLARITY ® (39 . 4 % ae ) 24 . 87 24 . 87 9 . 8 Agnique PG 8107 - G 2 . 0 2 . 0 0 .01 42 . 98 42 . 98 19 . 6 SAG 1572 0 . 01 1 .35 MEA glyphosate (45 .6 % ae ) 10 Ferric sulfate 0 . 19 0 . 19 Ethoquad C12 75 DEG 3 . 5 3 . 5 Citric Acid 0 . 30 0 . 30 13 . 95 13. 95 5 . 40 0 . 01 Potassium acetate (38 . 7 % AcOH ) SAG 1572 0 .01 water 20 . 81 20 . 81 Ferric sulfate 0 . 14 0 . 14 Citric acid 0 . 26 0 . 26 15 acetic acid 5 . 32 5 . 32 Example 2 - E : Dry Concentrate Compositions potassium hydroxide 11 . 11 11. 11 (Dicamba ) water 11 .81 11. 81 Dry granules having the compositions shown in Table 20 2 -30 and Table 2 -31 were prepared . The sodium dicamba and the sodium acetate were mixed together in a blender . TABLE 2 - 26 The PEG 8000 , antifoam , and water were then added to the blender and mixing continued . The amount of water added (Composition 261) was an amount sufficient to generate a paste suitable for INGREDIENT T ( g ) WT % % ACTIVE 25 extrusion . The paste was extruded under pressure through a 1 mm opening to obtain granules . The granules were CLARITY ® ( 39 . 4 % ae ) 24 . 87 24 . 87 9 . 8 extruded a total of three times to obtain granules that were 1 .35 MEA glyphosate (45 .6 % ae ) 42. 98 42. 98 19 . 6 AGM 550 2 . 5 2 . 5 not too dry. The final extruded granules were then dried in Agnique PG 8107 - G 2 . 0 2 . 0 a fluidized bed dryer at 70° C . to yield dry granules having SAG 1572 0 . 01 0 . 01 30 an off -white color. Ferric sulfate 0 . 14 0 . 14 Citric Acid 0 .26 0 . 26 TABLE 2 - 30 Acetic acid 5 . 32 5 . 32 potassium hydroxide (45 % soln ) 7 . 33 7 .33 Composition T2 - 30 ) water 14 . 59 14 . 59 35 INGREDIENT WT (g ) WT % % ACTIVE

Sodium dicamba 85 .UU 00 85 .00 68 . 0 Sodium acetate 10 . 00 10 . 00 TABLE 2 - 27 PEG 8000 4 . 90 4 . 90 (Composition 567 - 2 ) Antifoam (Momentive , SAG 1572) 0 . 10 0 . 10 40 INGREDIENT WT ( g ) WT % % ACTIVE CLARITY ® ( 39. 4 % ae ) 26 . 02 26 . 02 10 . 25 TABLE 2 -31 1. 35 MEA glyphosate (45 .6 % ae ) 44 . 96 44 . 96 20 . 5 AGM 550 2 . 5 2 . 5 ( Composition T2 -31 ) Agnique PG 8107 - G 2 . 2 2 . 2 45 SAG 1572 0 . 01 0 .01 INGREDIENT WT ( g ) WT % % ACTIVE Ferric sulfate 0 .14 0 . 14 Citric Acid 0 . 26 0 . 26 Sodium dicamba 81. 25 81. 25 65 . 0 Acetic acid 5 . 57 5 . 57 Sodium acetate 10 .00 10 . 00 potassium hydroxide (45 % soln ) 7 .67 7 .67 PEG 8000 4 . 90 4 . 90 water 10 .67 10 .67 Antifoam (Momentive , SAG 1572) 0 . 10 0 . 10

TABLE 2 - 28 Example 3 : Measurement of Dicamba Volatility (Humidome ) ( Composition 331 - 3 ) 55 Humidomes obtained from Hummert International (Part INGREDIENT WT ( g ) WT % % ACTIVE Nos 14 - 3850 - 2 for humidomes and 11 - 3050 - 1 for 1020 flat CLARITY ® ( 39. 4 % ae ) 24 . 87 24 . 87 9 . 8 tray ) were modified by cutting a 2 .2 cm diameter hole on one 1 . 35 MEA glyphosate (45 .6 % ae ) 42 . 98 42 . 98 19 . 6 AGM 550 2 . 5 2 . 5 end approximately 5 cm from the top to allow for insertion Agnique PG 8107 - G 2 . 0 2 . 0 60 of a glass air sampling tube ( 22 mm OD ) containing a SAG 1572 0 .01 0 . 01 polyurethane foam ( PUF ) filter. The sampling tube was Ferric sulfate 0 . 14 0 . 14 secured with a VITON O - ring on each side of the humidome Citric Acid 0 . 26 0 . 26 Acetic acid 5 . 32 5 . 32 wall . The air sampling tube external to the humidome was potassium hydroxide ( 45 % soln ) 11 . 11 11. 11 fitted with tubing that was connected to a vacuum manifold water 10 . 81 10 . 81 65 immediately prior to sampling . The flat tray beneath the humidome was filled with 1 liter of sifted dry or wet 50 / 50 soil (50 % Redi- Earth and 50 % US US 10 , 212 , 933 B2 51 52 10 Field Soil ) to a depth of about 1 cm . The flat tray bottom TABLE 3 - 2 -continued containing the dicamba formulation on soil was covered with the humidome lid and the lid was secured with clamps . DICAMBA STD STD The assembled humidomes were placed in a temperature and ID COMPOSITION (ng / L) DEV ERROR humidity controlled environment and connected to a vacuum 5 731- C 1 . 2 % ae CLARITY® + nd nana nana 2 . 4 % ae POWERMAX ® + manifold through the air sampling line . Air was drawn 2 % potassium acetate through the humidome and PUF at a rate of 2 liters per 854 - C 1 . 2 % ae CLARITY ® + 00 . 04 0. 01 0 . 01 01 minute (LPM ) for 24 hours at which point the air sampling 2 . 4 % ae POWERMAX ® + was stopped . The humidomes were then removed from the 2 % dipotassium phosphate controlled environment and the PUF filter was removed . The 10 PUF filter was extracted with 20 mL of methanol and the solution was analyzed for dicamba concentration using TABLE 3 - 3 LC -MS methods known in the art . DICAMBA STD STD To measure the dicamba concentration in the gas phase 15 ID COMPOSITION DEV ERROR ( air ) that volatilized from the spray solutions, compositions 751 - A 1 . 2 % ae CLARITY ® 0 .02 0 .00 0 .00 were prepared to contain 1 . 2 % a .e . dicamba which is equiva 751 - B 1 . 2 % ae CLARITY ® + 1 . 04 0 . 50 0 . 25 lent to an application rate of 1 . 0 lb / A a . e . at 10 gallons per 2 . 4 % ae POWERMAX ® acre (GPA ) . Where glyphosate was added or was part of the 751- E 1 . 2 % ae CLARITY ® + 6 . 13 0 . 55 0 . 32 2 . 4 % ae POWERMAX ® + formulation , glyphosate was present at a concentration of 20 1 % AMS 2 . 4 % a . e . or 2 . 0 lb /Aa . e . Where 2 , 4 - D was added or was part 751- C 1 . 2 % ae CLARITY ® + nd na na of the formulation , 2 , 4 - D was present at 2 . 4 % ae or 2 . 0 lb / A 2 . 4 % ae PowerMAX + 2 % potassium acetate ae at 10 gallons per acre (GPA ) . The growth chambers were 751 - D 1 . 2 % ae CLARITY ® + 3 .63 0 . 38 set at 35º C . and 40 % relative humidity (RH ) . For each 2 . 4 % ae POWERMAX ® + 0. 77 0. 38 composition four separate humidome boxes were sprayed to 2 % potassium acetate + have 4 replicate measurements for each formulation . Tables 1 % ammonium sulfate 3 - 1 to 3 - 12 below provide the mean concentration of dicamba in air for the tested formulations. Where concen trations of dicamba were below the limits of detection , “ nd ” 30 TABLE 3 - 4 is indicated in the tables below . DICAMBA STD STD Humidome Results : ID COMPOSITION DEV ERROR 210 - A 1 . 2 % ae CLARITY ® + 0. 92 0 .22 0 .11 TABLE 3 - 1 2 . 4 % ae POWERMAX ® 35 210 - B 1 . 2 % ae Clarity + nd na na 2 . 4 % ae POWERMAX ® + na DICAMBA STD STD 2 % potassium acetate ID COMPOSITION ( ng / L ) DEV ERROR 210 -C 1 . 2 % ae CLARITY ? + 0 . 16 0 . 02 02 0 .01 01 2 . 4 % ae POWERMAX ® + 2 % potassium acetate + 854 - A 1 . 2 % ae CLARITY ® 0 .03 0 .00 0 .00 40 1 % ammonium sulfate 854 - B 1. 2 % ae CLARITY ® + 0 . 44 210 - D 1 . 2 % ae CLARITY ® + 0 .01 0 .00 0 .00 0. 11 0 .06 2 . 4 % ae POWERMAX ® + 2 . 4 % ae POWERMAX® 2 % potassium acetate / 854- F 1. 2 % ae CLARITY ® + nd na na dipotassium phosphate 2 . 4 % ae POWERMAX ® + 2 % potassium acetate 854 - C 1. 2 % ae CLARITY ® + 0 .06 0 .01 0 .01 TABLE 3 - 5 2 . 4 % ae POWERMAX ® + DICAMBA STD STD 2 % dipotassium phosphate ID COMPOSITION ( ng/ L ) DEV ERROR 854 - D 1 . 2 % ae CLARITY ® 0. 47 0 .13 0. 06 870 - A 2 . 4 % ae DURANGO ® 0 . 10 0 .03 0 .01 DMA ® + 2 . 4 % 2 , 4 - D amine 2 . 4 % ae POWERMAX ® + 870 - B 2 . 4 % ae DURANGO ® 0 .01 0 .00 0. 00 2 % potassium oxalate DMA ® + 2 . 4 % 2 , 4 - D amine + 2 % potassium acetate 854 - E 1 . 2 % ae CLARITY ® 0 . 33 0 .20 0 .10 870 - D 2 . 4 % ae IPA glyphosate + 0 .09 0 .03 0 . 01 2 . 4 % ae POWERMAX ® + 2 . 4 % ae 2 , 4 - D amine 870 -C 2 . 4 % ae IPA glyphosate + 0 .01 0 .01 0 .00 2 % potassium citrate 2 . 4 % ae 2 , 4 - D amine + 0. 01 0 .01 0. 00 2 % potassium acetate

TABLE 3 - 2 60 TABLE 3 -6 DICAMBA STD STD ID COMPOSITION ( ng / L ) DEV ERROR DICAMBA STD STD ID COMPOSITION DEV ERROR 854 - A 1 . 2 % ae CLARITY ® 0 .02 0 . 00 0 .00 854 - B 1 . 2 % ae CLARITY ® + 0 . 49 0 . 16 0 .08 65 563 - 2 1 . 2 % ae BANVEL ® + 1 . 92 0 .31 0. 15 2 . 4 % ae POWERMAX ® 2 . 4 % POWERMAX ® US 10 ,212 , 933 B2 53 54 TABLE 3 -6 - continued TABLE 3 - 8 - continued DICAMBA STD STD ID COMPOSITION ( ng/ L ) DEV ERROR DICAMBA STD STD ID COMPOSITION ( ng/ L ) DEV ERROR 563 - 5 1 . 2 % ae BANVEL ® + 0 . 02 0 . 01 0 .005 – 2 . 4 % POWERMAX ® + 2 % potassium acetate 893 - C 1 . 2 % ae CLARITY ® + 0 .007 0. 00 0 .00 563 - 3 1 . 2 % ae CLARITY ® + 0 .49 0 . 13 0 .06 2 . 4 % POWERMAX ® + 2 . 4 % ae PowerMAX 2 % potassium benzoate 563- 6 1 . 2 % ae CLARITY ® + 0 .01 0 .01 0 .00 893 - D 1 . 2 % ae CLARITY ® + 0 . 003 0 . 00 0 .00 2 . 4 % ae POWERMAX ® + 10 2 % potassium acetate 2 . 4 % POWERMAX ® + 563 - 1 1 . 2 % ae MEA dicamba + 1 .04 0 .24 0 .12 2 % potassium formate 2 . 4 % ae POWERMAX ® 893 - E 1 . 2 % ae CLARITY ® + 0 . 001 0 .00 0 . 00 563 - 4 1 . 2 % ae MEA dicamba + 0 .01 0 .00 0 .00 2 . 4 % ae POWERMAX ® + 2 . 4 % POWERMAX ® + 2 % potassium acetate 1515 2 % sodium acetate

TABLE 3 - 9 MOLAR MOLAR RATIO RATIO CARBOXYLIC CARBOXYLIC DICAMBA STD STD ID COMPOSITION ACID : DICAMBA ACID :KOH DEV ERR 836 - 1 1 . 2 % ae CLARITY ® + ?? ?? 1. 139 0 .34 0 .17 2 . 4 % POWERMAX ® 836 - 6 1 . 2 % ae CLARITY ? + NA NA 0 .029 0 .01 0 .00 2 . 4 % POWERMAX ® ++ potassium hydroxide 836 - 3 1 . 2 % ae CLARITY ® +T 2 : 1 1 : 1 0 .011 0 .01 0 .00 2 . 4 % POWERMAX ® ++ propionic acid + potassium hydroxide 836 - 5 1 . 2 % ae CLARITY ® + 2 : 1 1 : 1 0 .012 0 . 00 0 . 00 2 . 4 % POWERMAX ® + formic acid + potassium hydroxide 836 - 2 1 . 2 % ae CLARITY ® + 2 : 1 1 : 2 0 . 064 0 .01 0 . 01 2 . 4 % POWERMAX ® + succinic acid + potassium hydroxide 836 - 4 1 . 2 % ae CLARITY ® + 2 : 1 1 : 1 0 .014 0 .01 0 .00 2 . 4 % POWERMAX ® + acetic acid + potassium hydroxide

TABLE 3 - 7 TABLE 3 - 10

DICAMBA STD STD 45 DICAMBA STD STD ID COMPOSITION ( ng/ L ) DEV ERROR ID COMPOSITION * ( ng/ L ) DEV ERROR 751- F 1 . 2 % ae DGA dicamba/MEA nd na na glyphosate premix + 321 - 1 1 . 2 % ae CLARITY ® 0 .016 0 .005 0 .003 2 % potassium acetate 321 - 2 1 . 2 % Composition 871 - 2 0 . 004 0 .001 0 .001 210 - E 1 . 2 % ae DGA dicamba /MEA 0 .07 0 .01 0 .00 50 321 - 3 1. 2 % Composition 871- 3 0 . 005 0 . 003 0 .002 glyphosate / 321 - 4 1. 2 % Composition 871- 4 0 . 003 0 . 000 0 . 000 0 .54 % potassium acetate premix 321 - 5 1. 2 % Composition 871- 5 0 .003 0 . 000 0 .000 210 - F 1 . 2 % DGA dicamba /MEA 0 .01 0 .00 0 .00 321- 6 1 .2 % Composition 871- 6 0 .003 0 .001 0 . 000 glyphosate premix + 2 % potassium * Test formulation was prepared by diluting referenced Composition with an amount of acetate /dipotassium phosphate 35 water sufficient to provide a test formulation containing 1. 2 % a. e . dicamba. TABLE 3 - 11 TABLE 3 - 8 DICAMBA STD STD DICAMBA STD STD 60 ID COMPOSITION * ( ng / L ) . DEV ERROR ID COMPOSITION (ng ) DEV ERROR 891 - 1 1 . 2 % ae CLARITY ® 0 . 367 0 . 110 0 .039 917 - 2 1 . 2 % ae CLARITY ® + 0 .015 0 .004 0 .001 893 - A 1 . 2 % ae CLARITY ® + 0 .83 0 . 10 0 .05 2 . 4 % ae POWERMAX ® 2 . 4 % POWERMAX ® 0 .006 893 - B 1 . 2 % ae CLARITY ® + 0 .003 0 . 00 0 . 00 917 - 3 1 . 2 % ae Composition 261 0 .002 0 . 000 65 2 . 4 % POWERMAX ® + * Test formulation was prepared by diluting referenced Composition with an amount of 2 % potassium acetate water sufficient to provide a test formulation containing 1 . 2 % a . e . dicamba . US 10 ,212 , 933 B2 55 56 TABLE 3 - 12 TABLE 4 - 1 DICAMBA STD STD ID COMPOSITION % INJURY ( 7 DAT ) ID COMPOSITION * ( ng / L ) DEV ERROR 889 - A 1 . 2 % ae DGA dicamba 15 % - 5 889 - D 1 . 2 % ae DGA dicamba + 364 - 1 1 . 2 % ae CLARITY ® 0 . 049 0 .018 0 .009 2 % potassium acetate 364 - 2 1 . 2 % ae Clarity + 1 .938 0 . 020 0 .012 3 . 36 % v / v Liberty 364 - 3 1 . 2 % ae Clarity + 0 .031 0 . 013 0 .007 TABLE 4 - 2 3. 36 % v/ v Liberty + 10 3 % v / v dipotassium phosphate % INJURY % INJURY 364 - 4 1 . 2 % ae Composition 871 - 5 0 .002 0 . 003 0 .001 ID COMPOSITION * ( 7 DAT) ( 14 DAT) 364 - 5 1 . 2 % ae Composition 871 - 5 + 0 . 191 0 . 033 0 . 019 3 .36 % v / v Liberty 321- 1 1 . 2 % ae CLARITY ® 10 .00 23 .33 364 - 6 1 .2 % ae Composition 871- 5 + 0 .013 0 .002 0 . 001 321 - 2 1 . 2 % Composition 871 - 2 0 . 00 5 . 13 15 321 - 3 1 . 2 % Composition 871- 3 0 . 63 8 . 50 3 . 36 % v / v Liberty + 321- 4 1 . 2 % Composition 871 - 4 4 . 13 15 . 38 3 % dipotassium phosphate 321 - 5 1 . 2 % Composition 871- 5 2 .63 10 .75 321- 6 1 . 2 % Composition 871- 6 5 . 38 15 . 38 * Test formulation was prepared by diluting referenced Composition with an amount of water sufficient to provide a test formulation containing 1 . 2 % a . e . dicamba . * Test formulation was prepared by diluting referenced Composition with an amount of water sufficient to provide a test formulation containing 1 . 2 % a . e . dicamba . 20 TABLE 3 - 12 TABLE 4 - 3 STD DICAMBA STD ER % INJURY % INJURY DEV ROR ( 7 DAT ) ( 14 DAT) ID COMPOSITION * 25 ID COMPOSITION * 268 - 1 1 . 2 % ae CLARITY ® + 4 .76 0 . 96 0 .48 891 - 1 1 . 2 % ae CLARITY ® 6 . 44 25 . 31 2 . 4 % ae ROUNDUP ® ENERGY 917 - 2 1 . 2 % ae CLARITY ® + 12. 50 44 . 38 268 - 2 1 . 2 % ae CLARITY ® + 1 . 11 0 . 47 0 .23 2 . 4 % ae POWERMAX ® 2 .4 % ae ROUNDUP ® ENERGY + 917 - 3 1 . 2 % ae Composition 261 3 . 25 9 .75 3 % dipotassium phosphsate 268 - 3 1 . 2 % ae CLARITY ® + 0 . 17 0 13 06 30 * Test formulation was prepared by diluting referenced Composition with an amount of 2 .4 % ae ROUNDUP ® ENERGY + water sufficient to provide a test formulation containing 1 . 2 % a . e . dicamba . 2 % potassium acetate 268 - 4 1 . 2 % ae CLARITY ? + 0 .00 0 . 00 0 . 00 2 . 4 % ae ROUNDUP ® ENERGY + Example 5 : Measurement of Herbicidal 4 % potassium acetate Effectiveness 268 - 5 1 . 2 % ae CLARITY ® + 0 .01 0 .01 0 .00 35 2 . 4 % ae ROUNDUP ® ENERGY + 2 % potassium acetate + The herbicidal effectiveness of the compositions of the 3 % dipotassium phosphate present invention can be assessed through conventional 268 - 6 1 . 2 % ae CLARITY + 1 . 55 0 . 52 0 . 26 greenhouse tests and / or field tests . Herbicidal effectiveness 2 . 4 % ae PowerMAX can be measured as a percentage “ inhibition ” following a * ROUNDUP ® ENERGY is the glyphosate ammonium salt, sold as water soluble granules 40 standard procedure in the art which reflects a visual assess in Europe. ment of plant mortality and growth reduction by comparison with untreated plants, made by technicians specially trained The results reported above for the di- and tri -carboxylic to make and record such observations. In all cases , a single acids tested (oxalic acid , citric acid , and succinic acid ) technician makes all assessments of percent inhibition indicate that those acids did not reduce dicamba volatility . In 45 within any one experiment or trial. Such measurements are addition , malic acid was tested and likewise did not reduce relied upon and regularly reported by Monsanto Technology dicamba volatility . LLC in the course of its herbicide business. The selection of application rates that are biologically Example 4 : Measurement of Dicamba Volatility so effective for a specific auxin herbicide is within the skill of ( Plant Response ) 50 the ordinary agricultural scientist . Those of skill in the art will likewise recognize that individual plant conditions, Herbicidal compositions were sprayed onto eight 90 mm weather and growing conditions, as well as the specific diameter glass Petri dishes . The eight Petri dishes were exogenous chemical and formulation thereof selected , will placed immediately on a plastic tray along with two 55 affect the weed efficacy and associated crop injury achieved Roundup Ready soybean plants at V1 -V1 . 5 development in practicing this invention . Useful application rates for the stage as indicators . The plastic trays were then covered with auxin herbicides employed can depend upon all of the above plastic domes, sealed with clamps around edges, and placed conditions. With respect to the use of the method of this invention , much information is known about appropriate in the growth chamber , at a set temperature and relativei 60 auxin application rates , and a weed control practitioner can humidity ( 85° F. day (16 h light) , 70° F . night (8 h dark ) and select auxin application rates that are herbicidally effective 40 % RH ) for 24 hours . After 24 hours , the plants were on particular species at particular growth stages in particular removed from the domes and transferred to a greenhouse . environmental conditions . The indicator plants were evaluated for visual symptoms Effectiveness in greenhouse tests, usually at exogenous typically at 5 , 7 and 14 days after treatment. 65 chemical rates lower than those normally effective in the Plant response results for compositions containing field , is a proven indicator of consistency of field perfor dicamba are listed in Tables 4 - 1 , 4 - 2 , and 4 . 3 : mance at normal use rates . US 10 ,212 , 933 B2 57 58 The compositions of the present invention can be applied Example 6 : Herbicidal Efficacy on ABUTH to plants by spraying, using any conventional means for (Velvetleaf ) and ELEIN (Gooseqrass ) spraying liquids, such as spray nozzles , atomizers , or the like . Compositions of the present invention can be used in The herbicidal tank mix compositions listed in the tables precision farming techniques , in which apparatus is 5 below were prepared using CLARITY® (DGA dicamba employed to vary the amount of exogenous chemical applied from BASF ) and ROUNDUP POWERMAX® (potassium to different parts of a field , depending on variables such as glyphosate from Monsanto ) by successively adding each the particular plant species present, soil composition , and the specified herbicide to water and mixing . The tank mixtures like . In one embodiment of such techniques , a global posi containing potassium acetate were prepared as described in tioning system operated with the spraying apparatus can be 10 Example 1 . used to apply the desired amount of the composition to Weed seeds were planted in 3 .5 in square plastic pots different parts of a field . The composition , at the time of application to plants , is filled with Redi- earth (Sun Gro , Bellevue , Wash .) containing preferably dilute enough to be readily sprayed using stan 100 g /cu ft Osmocote 14 - 14 - 14 slow release fertilizer. Ten to dard agricultural spray equipment . Preferred application fifteen weed seeds were planted about one -half inch deep rates for the present invention vary depending upon a 15 and loosely covered with Redi- Earth potting media . The pots number of factors , including the type and concentration of were placed in a controlled environment equipped with active ingredient and the plant species involved . Useful rates sub - irrigation . Growth conditions were 27° C . day and 21° for applying an aqueous composition to a field of foliage can C . night with fourteen hours of supplemental light (approxi range from about 25 to about 1 ,000 liters per hectare ( 1 /ha ) mately 600 microeinsteins ). After germination and emer by spray application . The preferred application rates for 20 gence from the potting media , the plants were thinned to aqueous solutions are in the range from about 50 to about achieve one plant per pot. Pots that contained plants that 300 l/ ha . were similar in appearance , size , and vigor were selected for Many exogenous chemicals ( including auxin herbicides ) treatment. Typically , the plants were four to eight inches tall must be taken up by living tissues of the plant and translo at the time of herbicide treatment. Compositions were cated within the plant in order to produce the desired 25 applied to the plants with a track sprayer generally using a biological ( e . g . , herbicidal) effect. Thus , it is important that Teejet 9501E flat fan nozzle or similar nozzle with air an herbicidal formulation not be applied in such a manner as pressure set at a minimum of 24 pounds per square inch . The to excessively injure and interrupt the normal functioning of spray nozzle was 16 inches above the top of the plants and the local tissue of the plant so quickly that translocation is a spray volume rate of approximately 10 gallons per acre ( 93 reduced . However, some limited degree of local injury can 30 L per hectare ) was applied . Each composition was applied at be insignificant, or even beneficial , in its impact on the three application rates and herbicide injury rating was made biological effectiveness of certain exogenous chemicals . 21 days post treatment. Results obtained with application of the composition to green foxtail (SETVI ) , velvetleaf ( ABUTH ) , and hemp TABLE 6 - 1 sesbania (SEBEX ) are shown in Tables 5 -1 , 5 - 2 , and 5 - 3 , Herbicidal Efficacy of Tank Mixtures Containing POWERMAX ® and respectively . In each case , application rates were 280 g ae /ha DGA dicamba /potassium acetate on ABUTH ( velvetleaf) and for dicamba and 560 g ae/ ha for glyphosate , and the reported ELEIN ( goosegrass ) result is an average of the results obtained from six separate % CONTROL applications. 40 AMT ( 21 DAT) TABLE 5 - 2 COMPOSITION (% ae ) RATE ABUTH ELEIN POWERMAX ® 39 . 8 140 ae g / ha 0 . 0 23 . 3 Green Foxtail (SETVI ) 280 ae g /ha 52 . 5 85 . 0 560 ae g /ha 74 . 2 93 . 8 Composition AVG % CONTROL 45 CLARITY ® 40 70 ae g /ha 10 . 0 0 . 0 ROUNDUP POWERMAX ® + CLARITY ® 99 . 7 140 ae g /ha 18. 3 10 . 0 Composition 249 - 3 99 . 7 g/ ha 36 . 7 10 . 0 503 - 1 31. 0 70 ae g /ha 10 . 8 0 . 0 503 - 1 31. 0 g/ ha 19 . 2 0 . 0 503 - 1 31. 0 280 ig / ha 33 . 3 0 . 0 50 503 - 3 31. 0 rg / ha 10 . 0 8 . 3 TABLE 5 - 2 503 - 3 31. 0 140 ae g /ha 17 . 5 11 . 7 503 - 3 31. 0 280 de g/ ha 35 . 0 7 . 5 Velvetleaf (ABUTH ) 295 - 3 31. 0 70 ae g /ha 13 . 3 295 - 3 31. 0 140 g /ha 20 . 0 11 . 7 Composition AVG % CONTROL 295 - 3 31. 0 280 ae g /ha 36 . 7 7 . 5 55 295 - 6 31. 0 70 ae g/ ha 12 . 5 ROUNDUP POWERMAX ® + CLARITY ® 90 . 8 295 - 6 31. 0 140 ae g /ha 21 . 7 0 . 0 Composition 249- 3 86 . 7 295 - 6 31. 0 280 ae g / ha 43 . 3 3 . 3 POWERMAX ® 39 . 8 140 ae 14 . 2 38 . 3 CLARITY ? 40 70 ae g /ha POWERMAX ® 39 . 8 280 46 .7 85 . 0 TABLE 5 - 2 CLARITY ® 40 140 ha 60 POWERMAX ® 39 . 8 % ae 560 ae 80 . 8 95 . 0 Hemp Sesbania (SEBEX ) CLARITY ® 40 % ae 280 ae obibobubb POWERMAX ® 39. 8 % ae 140 ae g / ha 11. 7 39 . 2 Composition AVG % CONTROL 503 - 1 31 . 0 % ae 70 POWERMAX ® 39. 8 % ae 280 62 .5 81. 7 ROUNDUP POWERMAX ® + CLARITY ® 99 . 2 503 - 1 31 . 0 % ae 140 ae g /ha Composition 249 - 3 100 POWERMAX ® 39. 8 % ae 560 ae g/ ha 82. 5 94 . 2 503 - 1 31. 0 % ae 280 ae 8tha US 10 , 212 ,933 B2 59 60 TABLE 6 - 1 - continued TABLE 6 - 2 - continued Herbicidal Efficacy of Tank Mixtures Containing POWERMAX ® and Herbicidal efficacy of premix composition containing glyphosate , DGA dicamba/ potassium acetate on ABUTH (velvetleaf ) and dicamba and potassium acetate on ABUTH (velvetleaf ) and ELEIN ( goosegrass ) ELEIN ( goosegrass ) % CONTROL % CONTROL (21 DAT) AMT ( 21 DAT) COMPOSITION ABUTH ELEIN COMPOSITION ( % ae ) RATE ABUTH ELEIN 249- 1 140 / 70 ae g /ha 33. 3 81. 7 POWERMAX ® 39 . 8 % ae 140 ae g /ha 15 . 0 35 . 0 10 280 / 140 ae g /ha 59 . 2 90 . 0 503 - 3 31. 0 % ae 70 ae g /ha 560 /280 ae g / ha 92 . 2 98 . 0 POWERMAX ® 39 . 8 % ae 280 ae g /ha 49 . 2 83 . 3 249 - 2 140 /70 ae g /ha 30 . 0 80 . 8 503 - 3 31. 0 % ae g/ ha 280 / 140 ae g /ha 58 . 3 90 . 8 POWERMAX ® 39 . 8 % ae 560 g/ ha 83 . 3 93 . 3 560 /280 ae g / ha 89 . 7 97 . 3 503 - 3 31. 0 % ae 280 g/ ha 249 - 3 140 / 70 ae g /ha 30 . 8 86 . 7 POWERMAX ® 39. 8 % ae g /ha 15 . 8 15 280 / 140 ae g /ha 63. 3 91 . 7 295 - 3 31 . 0 % ae g/ ha 26. 7 15 560 / 280 ae g / ha 86 .7 98 .2 POWERMAX ® 39. 8 % ae 280 ae g/ ha 54 . 2 8282 . 5 UNTREATED 0 0 . 0 0 . 0 295 - 3 31. 0 % ae 140 ae g/ ha CHECK POWERMAX ® 39 . 8 % ae 560 ae g/ ha 83 . 3 90 . 0 295 - 3 31 . 0 % ae 280 ae g/ ha POWERMAX ® 39. 8 % ae 140 ae g/ ha 17 . 5 4242 . 5 20 This written description uses examples to disclose the 295 - 6 31. 0 % ae g/ ha invention , including the best mode , and also to enable any POWERMAX ® 39. 8 % ae 280 ae g /ha 55. . 0 80 . .0 person skilled in the art to practice the invention , including 295- 6 31 . 0 % ae 140 ae g /ha POWERMAX ® 39. 8 % ae 560 ae g/ ha 85 . 8 85 . 0 making and using any devices or systems and performing 295 - 6 31 . 0 % ae 280 ae g /ha any incorporated methods. The patentable scope of the UNTREATED 0 . 0 1 . 0 25 invention is defined by the claims, and may include other CHECK examples that occur to those 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 Herbicidal premix compositions listed in the tables below literal language of the claims, or if they include equivalent were prepared as previously described in Example 2 . 30 structural elements with insubstantial differences from the TABLE 6 - 2 literal languages of the claims. Herbicidal efficacy of premix composition containing glyphosate , What is claimed is : dicamba and potassium acetate on ABUTH ( velvetleaf) and 1. A herbicidal composition concentrate comprising : ELEIN ( goosegrass ) - 35 dicamba, or an agriculturally acceptable salt or ester % CONTROL ( 21 DAT) thereof; and a potassium or sodium monocarboxylate of a monocar COMPOSITION ABUTH ELEIN boxylic acid ; RATE wherein : 40 the concentrate comprises an amount of the potassium POWERMAX ® 140 ae g /ha 21 . 7 78. 3 280 ae g / ha 71. 7 95. 0 or sodium monocarboxylate sufficient to reduce the 560 ae g /ha 84 . 2 99 . 0 concentration of volatilized dicamba in the vapor CLARITY ® 70 ae g /ha 20 . 0 0 . 0 phase surrounding a diluted version of the concen 140 ae g /ha 36 .7 0 .0 280 ae g / ha 60 . 8 0 . 0 45 trate relative to the concentration of volatilized POWERMAX ® 140 ae g / ha 26 . 7 81. 7 dicamba in the vapor phase surrounding an otherwise CLARITY ® 70 ae g /ha identical diluted version of the concentrate lacking POWERMAX ® 280 ae g /ha 59 .2 90 . 0 CLARITY ® 140 ae g /ha the potassium or sodium monocarboxylate . POWERMAX ® 560 ae g / ha 85 . 8 92 . 5 2 . The herbicidal composition concentrate of claim 1 , CLARITY ? 280 ae g /ha 50 wherein the concentrate comprises an agriculturally accept RATE GLY /DICAMBA able salt of dicamba selected from the group consisting of 287 - 5 140 /70 ae g/ ha 20 . 0 0 . 0 N , N -bis - ?aminopropyl ]methylamine , monoethanolamine , 280 / 140 ae g /ha 51. 7 10 . 0 dimethylamine , isopropylamine, diglycolamine , potassium , 560/ 280 ae g /ha 71. 7 68 . 3 and sodium salts , and combinations thereof. 287 - 6 140 /70 ae g /ha 18 .3 0 . 0 55 3 . The herbicidal composition concentrate of claim 1 , 280 / 140 ae g / ha 50 . 0 10 . 0 560 / 280 ae g /ha 73 . 3 39 . 2 wherein the concentrate comprises the diglycolamine salt of 512 - 1 140 / 70 ae g /ha 22 . 5 84 . 2 dicamba . 280 / 140 ae g / ha 64. 2 93 . 3 4 . The herbicidal composition concentrate of claim 1 , 560/ 280 ae g /ha 92 .7 97 . 2 wherein the monocarboxylic acid is selected from the group 248 - 1 140 /70 ae g /ha 32. 5 78 . 3 280/ 140 ae g /ha 63 . 3 92 . 2 60 consisting of formic acid , acetic acid , propionic acid , and 560 / 280 ae g /ha 85 .5 95 . 0 benzoic acid . 248 - 2 140 /70 ae g /ha 38. 3 78 . 3 5 . The herbicidal composition concentrate of claim 1 , 280 / 140 ae g /ha 57. 5 93 . 3 wherein the concentrate comprises the potassium or sodium 560 /280 ae g /ha 85 . 8 95 . 0 248 - 3 140 / 70 ae g /ha 30 . 0 80 . 8 monocarboxylate salt, in whole or in part , in dissociated 280 / 140 ae g /ha 51. 7 90 . 8 65 form , the monocarboxylate salt selected from the group 560 /280 ae g /ha 84 . 7 96 . 5 consisting of formate salts , acetate salts , propionate salts , and benzoate salts of the monocarboxylic acid . US 10 ,212 , 933 B2 62 6 . The herbicidal composition concentrate of claim 1 , 24 . The herbicidal composition concentrate of claim 1 , wherein the concentrate comprises acetic acid , or an agri- wherein the concentrate is a dry concentrate and comprises culturally acceptable salt thereof. an amount ( acid equivalent weight) of the monocarboxylate , 7 . The herbicidal composition concentrate of claim 1 , of from about 5 % to about 15 % by weight of the concentrate . wherein the concentrate comprises an additive selected from 5 25 . The herbicidal composition concentrate of claim 1 , the group consisting of surfactants , drift reduction agents , wherein the composition comprises : safeners , solubility enhancing agents , thickening agents , flow enhancers , foam -moderating agents , freeze protectants, acetic acid , or an agriculturally acceptable salt thereof; UV protectants , preservatives , antimicrobials, and / or other wherein the molar ratio of acetic acid , or agriculturally additives that are necessary or desirable to improve the 10 acceptable salt thereof, to dicamba , or agriculturally performance , crop safety , or handling of the composition . acceptable salt or ester thereof, is from about 1 : 10 to 8 . The herbicidal composition concentrate of claim 1 , about 10 : 1 ; and / or wherein the concentrate comprises less than about 10 ppm of wherein the acid equivalent weight ratio of acetic acid , or ammonium sulfate . agriculturally acceptable salt thereof, to dicamba , or 9 . The herbicidal composition concentrate of claim 1 , 15 agriculturally acceptable salt or ester thereof, is from wherein the concentrate contains dicamba at a total loading about 1 : 10 to about 5 : 1 ; and / or of from about 120 to about 600 g acid equivalent ( a . e . ) / L . wherein the concentrate contains an amount (acid equiva 10 . The herbicidal composition concentrate of claim 1 , lent weight) of the acetic acid , or agriculturally accept wherein the concentrate contains dicamba at a total loading able salt thereof, from about 0 . 25 % to about 25 % by of from about 300 g a . e . / L to about 600 g a . e . / L . 20 weight of the concentrate ; and /or 11 . The herbicidal composition concentrate of claim 1 , wherein the concentration of the acetic acid , or agricul wherein the concentrate contains dicamba at a total loading turally acceptable salt thereof , is from about 1 gram of from about 350 g a . e ./ L to about 600 g a . e . / L . (acid equivalent weight) / L to about 250 grams (acid 12 . The herbicidal composition concentrate of claim 1 , equivalent weight )/ L ; and / or wherein the concentrate contains dicamba at a total loading 25 wherein the concentration of dicamba , or an agriculturally of from about 400 g a . e . / L to about 600 g a . e . / L . acceptable salt or ester thereof, is from about 120 grams 13 . The herbicidal composition concentrate of claim 1 , (acid equivalent weight )/ L to about 600 grams ( acid wherein the concentrate contains dicamba at a total loading equivalent weight) / L . of from about 450 g a .e ./ L to about 600 g a .e ./ L . 26 . The herbicidal composition concentrate of claim 1 , 14 . The herbicidal composition concentrate of claim 1 , 30 wherein the composition comprises : wherein the concentrate contains dicamba at a total loading acetic acid , or an agriculturally acceptable salt thereof; of from about 500 g a . e ./ L to about 600 g a . e ./ L . wherein the concentration of dicamba , or an agriculturally 15 . The herbicidal composition concentrate of claim 1 , acceptable salt or ester thereof , is from about 120 grams wherein the composition is a liquid concentrate containing a ( acid equivalent weight) / L to about 600 grams ( acid total amount ( acid equivalent weight ) of dicamba from about 35 equivalent weight ) / L ; and 5 % to about 75 % by weight of the concentrate . wherein the acid equivalent weight ratio of acetic acid , or 16 . The herbicidal composition concentrate of claim 1 , agriculturally acceptable salt thereof, to dicamba , or wherein the composition is a liquid concentrate containing a agriculturally acceptable salt or ester thereof, is from total amount ( acid equivalentweight ) of dicamba from about about 1 : 10 to about 5 : 1 . 25 % to about 35 % by weight of the concentrate . 40 27 . The herbicidal composition concentrate of claim 1 , 17 . The herbicidal composition concentrate of claim 1 , wherein the composition comprises : wherein the composition is a dry concentrate containing a acetic acid , or an agriculturally acceptable salt thereof; total amount (acid equivalentweight ) of dicamba from about and 40 % to about 90 % by weight of the concentrate . wherein : 18 . The herbicidal composition concentrate of claim 1 , 45 the concentrate contains an amount ( acid equivalent wherein the molar ratio of dicamba to the potassium or weight ) of the acetic acid , or agriculturally acceptable sodium monocarboxylate, is from about 1 : 10 to about 10 : 1 . salt thereof, from about 1 % to about 25 % by weight of 19 . The herbicidal composition concentrate of claim 1 , the concentrate ; and wherein the molar ratio of dicamba to the potassium or the concentrate contains an amount ( acid equivalent sodium monocarboxylate , is from about 2 : 1 to about 1 : 2 . 50 weight) of dicamba , or an agriculturally acceptable salt 20 . The herbicidal composition concentrate of claim 1 , or ester thereof, from about 10 % to about 60 % by wherein the concentration of the potassium or sodium mono weight of the concentrate . carboxylate , is from about 1 gram ( acid equivalent 28 . The herbicidal composition concentrate of claim 1 , weight) / L to about 250 grams ( acid equivalent weight) / L . wherein the composition comprises : 21 . The herbicidal composition concentrate of claim 1 , 55 acetic acid , or an agriculturally acceptable salt thereof; wherein the concentrate comprises an amount ( acid equiva and lent weight) of the potassium or sodium monocarboxylate , wherein : of from about 1 % to about 20 % by weight of the concentrate . the concentrate contains an amount ( acid equivalent 22 . The herbicidal composition concentrate of claim 1 , weight ) of the acetic acid , or agriculturally acceptable wherein the concentrate comprises an amount (acid equiva - 60 salt thereof, from about 2 % to about 20 % by weight of lent weight ) of the potassium or sodium monocarboxylate , the concentrate ; and of from about 2 % to about 15 % by weight of the concentrate . the concentrate contains an amount ( acid equivalent 23 . The herbicidal composition concentrate of claim 1 , weight ) of dicamba , or an agriculturally acceptable salt wherein the concentrate is a liquid concentrate and com or ester thereof, from about 15 % to about 50 % by prises an amount ( acid equivalent weight ) of the monocar - 65 weight of the concentrate . boxylate , of from about 2 % to about 10 % by weight of the 29 . The herbicidal composition concentrate of claim 1 , concentrate . wherein the composition comprises : US 10 ,212 , 933 B2 63 64 acetic acid , or an agriculturally acceptable salt thereof; 34 . A herbicidal composition concentrate comprising: and ( a ) dicamba , or an agriculturally acceptable salt or ester wherein : thereof; the concentrate contains an amount ( acid equivalent ( b ) at least one monocarboxylic acid ; and weight) of the acetic acid , or agriculturally acceptable 5 ( c ) a neutralizing base , wherein the neutralizing base is an salt thereof, from about 3 % to about 15 % by weight of alkali metal hydroxide selected from potassium the concentrate ; and hydroxide , sodium hydroxide , or a mixture thereof, the concentrate contains an amount (acid equivalent wherein : weight ) of dicamba , or an agriculturally acceptable salt the concentrate comprises an amount of the monocar or ester thereof, from about 20 % to about 40 % by 10 boxylic acid and neutralizing base sufficient to weight of the concentrate . reduce the concentration of volatilized dicamba in 30 . The herbicidal composition concentrate of claim 1 , the vapor phase surrounding a diluted version of the wherein the composition comprises: concentrate relative to the concentration of volatil acetic acid , or an agriculturally acceptable salt thereof; 15 ized dicamba in the vapor phase surrounding an and otherwise identical diluted version of the concentrate wherein : lacking the monocarboxylic acid , and neutralizing the concentrate contains an amount (acid equivalent base . weight) of the acetic acid , or agriculturally acceptable 35 . A herbicidal composition comprising : salt thereof, from about 3 % to about 10 % by weightof 20 ( a ) dicamba or an agriculturally acceptable salt or ester the concentrate ; and thereof; the concentrate contains an amount (acid equivalent (b ) at least one monocarboxylic acid , or a monocarboxy weight) of dicamba , or an agriculturally acceptable salt late thereof; or ester thereof, from about 25 % to about 35 % by ( c ) a neutralizing base , wherein the neutralizing base is an weight of the concentrate. alkali metal hydroxide selected from potassium 31. The herbicidal composition concentrate of claim 1 , hydroxide, sodium hydroxide, or a mixture thereof; and wherein the concentrate is a dry concentrate comprising : ( d ) water; acetic acid , or an agriculturally acceptable salt thereof; wherein : and the composition comprises an amount of the monocar wherein : 30 boxylic acid and neutralizing base , or an amount of the the concentrate contains an amount ( acid equivalent weight) of the acetic acid , or agriculturally acceptable monocarboxylate , sufficient to reduce the concentration salt thereof, from about 1 % to about 40 % by weight of of volatilized dicamba in the vapor phase surrounding the concentrate ; the composition relative to the concentration of vola the concentrate contains an amount ( acid equivalent 35 tilized dicamba in the vapor phase surrounding an weight ) of dicamba , or an agriculturally acceptable salt otherwise identical composition lacking the monocar or ester thereof, from about 40 % to about 90 % by boxylic acid and neutralizing base , or monocarboxy weight of the concentrate ; and late . wherein the sum of the acetic acid weight percent and the 36 . The herbicidal composition of claim 35 , wherein the dicamba weight percent is less than or equal to 100 % . 40 herbicidal composition is prepared by a process comprising : 32 . The herbicidal composition concentrate of claim 1 , mixing the dicamba , or agriculturally acceptable salt or wherein the concentrate is a dry concentrate comprising : ester thereof, the monocarboxylic acid , and a neutral acetic acid , or an agriculturally acceptable salt thereof; izing base comprising an alkali metal hydroxide wherein : selected from potassium hydroxide , sodium hydroxide , the concentrate contains an amount ( acid equivalent 45 or a mixture thereof, thereby forming a liquid concen weight ) of the acetic acid , or agriculturally acceptable trate comprising the dicamba , or agriculturally salt or salt thereof, from about 3 % to about 30 % by weight of ester thereof, and the monocarboxylate . the concentrate ; and 37 . The herbicidal composition of claim 35 , wherein the the concentrate contains an amount ( acid equivalent herbicidal composition is prepared by a process comprising : weight ) of dicamba , or an agriculturally acceptable salt 50 mixing the dicamba , or agriculturally acceptable salt or or ester thereof, from about 50 % to about 80 % by ester thereof, with the monocarboxylate , thereby form weight of the concentrate ; and ing a liquid concentrate comprising the dicamba , or wherein the sum of the acetic acid weight percent and the agriculturally acceptable salt or ester thereof, and the dicamba weight percent is less than or equal to 100 % . monocarboxylate . 33 . The herbicidal composition concentrate of claim 1 , 55 38 . The herbicidal composition of claim 35 , wherein : wherein the concentrate is a dry concentrate comprising : the molar ratio ofmonocarboxylic acid , or monocarboxy acetic acid , or an agriculturally acceptable salt thereof; late thereof, to dicamba , or an agriculturally acceptable and salt or ester thereof, is from about 1 : 10 to about 10 : 1 ; wherein : and / or the concentrate contains an amount ( acid equivalent 60 the acid equivalent weight ratio of monocarboxylic acid , weight) of the acetic acid , or agriculturally acceptable or monocarboxylate thereof, to dicamba, or an agricul salt thereof, from about 5 % to about 20 % by weight of turally acceptable salt or ester thereof, is from about the concentrate ; and 1 : 10 to about 5 : 1 ; and /or the concentrate contains an amount ( acid equivalent the composition comprises an amount ( acid equivalent weight ) of dicamba , or an agriculturally acceptable salt 65 weight) of the monocarboxylic acid , or monocarboxy or ester thereof, from about 60 % to about 75 % by late thereof, from about 0 .01 % to about 25 % by weight weight of the concentrate . of the composition ; and /or US 10 ,212 , 933 B2 65 66 the concentration of the monocarboxylic acid , or mono carboxylate thereof, is from about 1 gram (acid equiva lent weight) / L to about 250 grams ( acid equivalent weight )/ L . 39 . The herbicidal composition of claim 35 , wherein the 5 concentration of dicamba , or an agriculturally acceptable salt or ester thereof , is from about 0 . 1 grams ( acid equivalent weight) / L to about 50 grams (acid equivalent weight) / L . 40 . The herbicidal composition of claim 35 , wherein the concentration of dicamba, or an agriculturally acceptable 10 salt or ester thereof, is from about 10 grams (acid equivalent weight) / L to about 50 grams (acid equivalent weight) / L . 41 . The herbicidal composition of claim 35 , wherein the composition comprises an amount ( acid equivalent weight ) of the monocarboxylic acid , or monocarboxylate thereof , 15 from about 0 .05 % to about 5 % by weight of the composi tion . 42 . The herbicidal composition of claim 35 , wherein the neutralizing base is potassium hydroxide . 43 . The herbicidal composition of claim 35 , wherein the 20 neutralizing base is sodium hydroxide . 44 . The herbicidal composition of claim 35 , comprising the neutralizing base and monocarboxylic acid at a molar ratio of about 50 : 50 ( 1 : 1 ) or about 60 :40 ( 1 . 5 : 1 ) . 45 . The herbicidal composition of claim 35 , wherein the 25 composition has a pH equal to or higher than the acid dissociation constant (pKa ) of the monocarboxylic acid present in the composition .