US00945.1767B2 (12) United States Patent (10) Patent No.: US 9.451,767 B2 Nolte et al. (45) Date of Patent: Sep. 27, 2016 (54) AQUEOUS COMPOSITION COMPRISING (52) U.S. Cl. DCAMIBA AND A DRIFT CONTROL AGENT CPC ............... A0IN 33/04 (2013.01); A0IN 37/10 (2013.01); A0IN 37/40 (2013.01); A0IN (71) Applicant: BASF SE, Ludwigshafen (DE) 37/44 (2013.01) (58) Field of Classification Search (72) Inventors: Marc Nolte, Mannheim (DE); Wen Xu, CPC ...................................................... AO1N 37/44 Cary, NC (US); Steven Bowe, Apex, USPC .......................................................... 514/564 NC (US); Maarten Staal, Durham, NC See application file for complete search history. (US); Terrance M. Cannan, Raleigh, NC (US) (56) References Cited (73) Assignee: BASF SE, Ludwigshafen (DE) FOREIGN PATENT DOCUMENTS (*) Notice: Subject to any disclaimer, the term of this WO WO O2,34047 5, 2002 patent is extended or adjusted under 35 W. w838g 1239 U.S.C. 154(b) by 101 days. WO WO 2011/O19652 2, 2011 WO WO 2011/O102.11 9, 2011 (21) Appl. No.: 14/408,172 WO WO 2012/076567 6, 2012 (22) PCT Filed: Jun. 11, 2013 OTHER PUBLICATIONS International Search Report dated Jul. 12, 2013, prepared in Inter (86). PCT No.: PCT/EP2013/061962 national Application No. PCT/EP2013/061962. S 371 (c)(1), International Preliminary Report on Patentability dated Jun. 6. (2) Date: Dec. 15, 2014 2014, prepared in International Application No. PCT/EP2013/ O61962. (87) PCT Pub. No.: WO2013/189773 Primary Examiner — Raymond Henley, III PCT Pub. Date: Dec. 27, 2013 (74) Attorney, Agent, or Firm — Brinks Gilson & Lione (65) Prior Publication Data (57) ABSTRACT US 2015/O173354 A1 Jun. 25, 2015 The present invention relates to an aqueous composition comprising dicamba and a drift control agent; to a method O O for preparing a tank mix, which comprises the step of Related U.S. Application Data contacting water and said composition, and optionally fur (60) Provisional application No. 61/662,390, filed on Jun. ther pesticides; to a method of controlling phytopathogenic 21, 2012. fungi and/or undesired vegetation and/or unde-sired insect or mite attack and/or for regulating the growth of plants, (30) Foreign Application Priority Data wherein the composition is allowed to act on the respective pests, their environment or the plants to be protected from Jul. 5, 2012 (EP) ..................................... 12175090 the respective pest, on the soil and/or on undesired plants and/or the crop plants and/or their environment; and finally (51) Int. Cl. to a use of the alkoxylate of the formula (I) as defined below AOIN 37/44 (2006.01) for reducing the wind drift of an aqueous composition AOIN 33/04 (2006.01) comprising a pesticide. AOIN 37/40 (2006.01) AOIN 37/10 (2006.01) 19 Claims, No Drawings US 9,451,767 B2 1. 2 AQUEOUS COMPOSITION COMPRISING Solutions, LLC (Arrow four, Corral AMS, InterLock, Place DCAMIBA AND A DRIFT CONTROL AGENT ment Propak, PowerLock), and various other discontinued commercial products, such as Apasil, Bivert, Chem-Trol, This application is a National Stage application of Inter Confine, Corral Poly, Drifgon, Driftgard, Drop Zone, Intac national Application No. PCT/EP2013/061962, filed Jun. 11, Plus, Nalcotrol, Nalcotrol II, Nalduatic, Progacyl, Target, 2013, which claims the benefit of U.S. Provisional Appli TMP, Wind-Fall. cation No. 61/662,390, filed Jun. 21, 2012, the entire con Preferred examples of drift control agents are tents of which are hereby incorporated herein by reference. lecithin derivatives, This application also claims priority under 35 U.S.C. S 119 linear nonionic polymers with a molecular weight of at to European Patent Application No. 12175090.5, filed Jul. 5, 10 2012, the entire contents of which is hereby incorporated least 20 kDa, herein by reference. guar gum, The present invention relates to an aqueous composition fatty alcohol alkoxylates. Preferred drift control agents are the fatty alcohol alkoxy comprising dicamba and a drift control agent; to a method lates. for preparing a tank mix, which comprises the step of 15 contacting water and said composition, and optionally fur Suitable lecithin derivatives are lecithin or its chemically ther pesticides; to a method of controlling phytopathogenic modified derivatives. Such drift control agents are for fungi and/or undesired vegetation and/or undesired insect or example commercially available as Liberate(R) or Compa mite attack and/or for regulating the growth of plants, dre(R) from Loveland Products. wherein the composition is allowed to act on the respective Suitable linear nonionic polymers with a molecular pests, their environment or the plants to be protected from weight of at least 20 kDa, may be selected from polyacry the respective pest, on the soil and/or on undesired plants lamide, polyacrylate, or a polyethylene glycol. Preferred and/or the crop plants and/or their environment; and finally nonionic polymers are polyacrylamide and polyacrylate. to a use of the alkoxylate of the formula (I) as defined below The molecular weight of said nonionic polymers is usually for reducing the wind drift of an aqueous composition 25 at least 50 kDa, preferably at least 100 kDa, and in particular comprising a pesticide. The preferred embodiments of the at least 1000 kDa. invention mentioned herein below have to be understood as Suitable guar gums are for example described in being preferred either independently from each other or in EP0660999, or are commercially available as AGRHOR) combination with one another. DEP 775 or AGRHOR) DR 200 from Rhodia. The reduction wind drift is an important object in agro 30 Preferred fatty alcohol alkoxylates are fatty alcohol chemistry. Various drift control agents are known showing a ethoxylates. The fatty alcohol may comprise a C-, pref wide variety of different chemical compositions. Thus, it is erably a Co. and in particular a C-1s fatty alcohol. The very difficult to identify new drift control agents or opti fatty alcohol ethoxylate may comprise from 1 to 15, pref mizing structures of known drift control agents. erably from 1 to 8, and in particular from 2 to 6 equivalents Dicamba is an important herbicide, which requires high 35 of ethylene oxide. Especially suitable fatty alcohol ethoxy drift control to avoid damages in neighboring fields. late is a Cao fatty alcohol, which comprises from 2 to 6 Object of the present invention was to find a new drift equivalents of ethylene oxide. control agent with improved properties. These agents should The drift control agent may have a HLB value of 4.0 to be easily to prepare starting from cheap, industrially avail 11.0, preferably of 6.0 to 10.0 and in particular of 8.0 to 10.0. able compounds, which are easy to handle. Yet another 40 In another particular preferred form the drift control agent object was to find a dicamba composition, which allows a (such as the alkoxylate of the formula (I)) has a HLB of 5.0 high drift control. to 8.0, and most preferably from 6.0 to 7.0. The HLB may The object was solved by an aqueous composition com be determined according to Griffin. prising dicamba and a drift control agent. The object was In an especially preferred form the drift control agent is a also solved by a use of the alkoxylate of the formula (I) as 45 fatty alcohol alkoxylate. Such as an alkoxylate of the formula defined below for reducing the wind drift of aqueous com (I) position comprising a pesticide. Drift control agents may be understood as chemical agents, which reduce the wind drift when spraying an wherein R is C-C-alkyl and/or -alkenyl, m is 2, 3, 4 or aqueous tank mix composition. Drift control agents are 50 a mixture thereof, and n is from 1 to 15. The alkoxylates of commercially available from various companies (trade the formula (I) are obtainable by common alkoxylation of names of the products given in brackets): Ag Spray, Inc. alcohols R OH, e.g. with ethylene oxide (resulting in (Halt), Ashland Specialty Ingredients (Soilcare), Brewer m=2), propylene oxide, or butylene oxide. International Inc. (Poly Control 2), Conklin Co. Inc. (Com R* may be an alkyl, alkenyl or a mixture thereof. Prefer plete), Helena Chemical Co. (AccuOuest WM. AccuZone 55 ably R' is an alkenyl or a mixture of an alkenyl with an alkyl. DC, Grounded. On-Line, Sta Put, Strike Zone, LineMan), In case R contains an alkenyl said alkenyl may comprise at Intracrop (Driftless), Kalo, Inc. (One AP XL, Spectra Tank least one double bond. R' is preferably a C-Co-alkyl Mix, Spectra Max), Loveland Products, Inc. (LI 700), Nalco and/or -alkenyl. More preferably R' is C-C-alkyl and/or Co. (Staput Plus), Precision Laboratories, Inc. (Border, -alkenyl. Especially preferred R is oleyl and/or cetyl. Border Xtra, Direct, Transport Plus), Rhodia Inc. (AgRHO 60 Preferably, m is 2, a mixture of 2 and 3, or a mixture of DEP, AgRHO DR), Sanitek Products, Inc. (SANAG Div.) 2 and 4. In particular, m is 2. (41-A, 38-F), Willowood USA (Willowood Driftguard), Preferably, n is from 2 to 8. In particular, n is from 2 to FORMULATORS TRADE NAMES: Brandt Consolidated, 5. Inc. (Drift Free), Custom Agricultural Formulators (Drifts In a very preferred form the drift control agent is an top), Loveland Products, Inc. (Compadre, Liberate, Reign, 65 alkoxylate of the formula (I), wherein R is C-Co-alkyl Reign LC, Weather Gard Complete), Wilbur-Ellis Co. and/or -alkenyl, m is 2, a mixture of 2 and 3, or a mixture (Bronc Max EDT, EDT Concentrate, In-Place), Winfield of 2 and 4, and n is from 2 to 8.