IIIUS00571690 1A United States Patent (19) 11 Patent Number: 5,716,901 Fenderson et al. 45) Date of Patent: Feb. 10, 1998 54 SYNERGISTC HERBCDAL 186118 7/1986 European Pat. COMPOSITIONS OF DIMETHENAMID, 186119 7/1986 European Pat. 18620 7/1986 European Pat. SULCOTRONE, AND ATRAZINE 230596 8/1987 European Pat. 24950 12/1987 European Pat. off. 75 Inventors: John M. Fenderson, Kiowa, Kans.; 35889 5/1989 European Pat. Of.. William B. O'Neal, Buffalo Grove, Ill.; 336898 10/1989 European Pat. Off. Théo Quaghebeur. Saint-Symphorien, 338992 10/1989 European Pat. off. Belgium; Karl-Christoph Schumm, 380.447 8/1990 European Pat. Off. Campinas, Brazil; Walter Van Loocke, 394889 10/1990 European Pat. Off. Meetkerke, Belgium 461079 12/1991 European Pat. off. 549524 6993 European Pat. Of.. (73) Assignee: Sandoz Ltd., Basel, Switzerland WO 91/10653 7/1991 WIPO WO 92/07837 5/1992 WIPO. WIPO (21) Appl. No.: 467,364 92/11761 7/1992 22 Filed: Jun. 6, 1995 OTHER PUBLICATIONS Related U.S. Application Data CA 118(23):228154u, Jun. 7, 1993. Weed Control And Soil Persistence Studies With Dimeth 63 Continuation of Ser. No. 265,594, Jun. 23, 1994, abandoned, enamid. In Maize, A. Rahman and T.K. James; Proc. 45th which is a continuation-in-part of Ser. No. 153,946, Nov. 16, N.Z. Plant Protection Conf. 1992: 84-88. 1993, abandoned, which is a continuation of Ser. No. 19,386, Feb. 18, 1993, abandoned, and a continuation-in Herbicidal Composition, Kimura et al.; United States Statu part of Ser. No. 152,066, Nov. 12, 1993, abandoned, which tory Invention Registration, Reg. No. H670. Sep. 5, 1989. is a continuation of Ser. No. 19,933, Feb. 19, 1993, aban SAN 582 H A New Herbicide For Weed Control. In Corn doned, and a continuation-in-part of Ser. No. 236,732, May And Soybeans, J. Harr, K. Seckinger, E. Ummel, Brighton 2, 1994. Crop Protection Conference-Weeds. 1991, pp. 87-92. 51) Int. Cl. ............. A01N 43/10; A01N 43/70; Weed Control in No-tillage and Conventional Corn (Zea A01N 35/06 mays) with ICIA-0051 and SC-0774, John S. Wilson and (52) U.S. Cl. .............. 504/134 Chester L. Foy; Weed Technology, 1990, vol. 4:731-738. 58 Field of Search .................................. 504/134, 138, CA118: 228154u. "Weed Control and Soil Persistence Stud 504/135 ies With Dimethenamid in Maize", Rahman et al., Proc. NZ. (56) References Cited Plant Prot. Conf. 45th 84-8, 1992. Harret al., Brighton Crop Protection Council, Weeds, vol. 1, U.S. PATENT DOCUMENTS 87-92 1991. 3,013,054 12/1961 Richter .................................... 504/144 4,666,502 5/1987 Seckinger et al. ... 504/13 Primary Examiner S. Mark Clardy 4,695,673 9/1987 Heather et al. ... ... 568/310 Attorney, Agent, or Firm-Bell Seltzer Intellectual Property 4,789,393 12/1988 Hanagan ................................. 504/215 Law Group; Alston & Bird LLP 4,869,748 9/1989 Knudsen ................................. 504,348 4,921,526 5/1990 Lee et al. ... ... 504,194 57 ABSTRACT 5,006,150 4/1991 Lee et al. ................................ 504/292 5,089,046 2/1992 Lee et al. ................................ 504/20 Co-application of dimethenamid with other herbicides pro vides improved herbicidal activity. FOREIGN PATENT DOCUMENTS 137963 4/1985 European Pat. Off. 5 Claims, No Drawings 5,716,901 1. 2 SYNERGISTIC HERBICIDAL Co-application can be achieved using tank mixes of COMPOSITIONS OF DIMETHENAMID, preformulated individual active ingredients, simultaneous or SULCOTRONE, AND ATRAZINE sequential (preferably 1-2 days) application of such formu lations or application of preformulated fixed pre-mix com binations of the individual active ingredients. This is a continuation of application Ser. No. 08/265,594, Examples of herbicides which may be used in combina filed on Jun. 23, 1994, abandoned, which is a continuation tion with dimethenamid in accordance with the invention in-part of application Ser. No. 08/153,946, filed Nov. 16, include 1993, abandoned, which is a continuation of application Ser. 1. auxin transport inhibitors, e.g. naptalam No. 08/019.386, filed Feb. 18, 1993 abandoned and a 2. growth regulators, including 1) benzoic acids. e.g. continuation-in-part of application Ser. No. 08/152.066, O dicamba: b) phenoxy acids i) acetic acid type, e.g. 2,4-D, filed Nov. 12, 1993, abandoned, which is a continuation of MCPA, ii) propionic acid type, e.g. 2,4-DP, MCPP, iii) application Ser. No. 08/019,933, filed Feb. 19, 1993, butyric acid type, e.g. 2.4-DB, MCPB; c) picolinic acids abandoned, and a continuation-in-part of application Ser. and related compounds, e.g. picloram, triclopyr, No. 08/236,732, filed May 2, 1994. furoxypyr, clopyralid The present invention concerns a method of controlling 15 3. photosynthesis inhibitors, including a) s-triazines i) chloro undesired plant growth employing co-application of dimeth substituted, e.g. atrazine, simazine, cyanazine, ii) meth enamid and at least one other herbicide, herbicidal compo oxy substituted, e.g. prometon, iii) methylthio substituted, sitions comprising dimethenamid and at least one other e.g. ametryn, prometryn; b) other triazines, e.g. herbicide and the use of such compositions in controlling hexazinone, metribuzin; c) substituted ureas, e.g. diuron, undesired plant growth. 20 fluometuron, linuron, tebuthiuron, thidiazuron, forchlor Dimethenamid (FRONTIERO) whose chemical name is fenuron; d) uracils, e.g. bromacil, terbacil; e) others, e.g. 2-chloro-N-(2,4-dimethyl-3 -thienyl)-N-(2-methoxy-1- bentazon, desmedipham, phenmedipham, propardi, methylethyl)-acetamide, processes for its production, herbi pyrazon, pyridate cidal compositions containing it and its use as a herbicide are 4. pigment inhibitors, including a) pyridazinones, e.g. nor described in U.S. Pat. No. 4666,502 the contents of which 25 flurazon; b) isoxazolones, e.g. clomazone; c) others, e.g. are incorporated herein by reference. Dimethenamid con amitrole, fluridone sists of 4 stereoisomers due to two chiral elements and can 5. growth inhibitors, including a) milotic disruptors i) thus also exist in the form of the individual isomers as dinitroanilines, e.g. trifluralin, prodiamine, benerin, diastereomeric mixtures (1S, aRS (known as ethalfluralin, isopropalin. oryzalin, pendimethalin; ii) S-dimethenamid) and 1R, aRS (known as R-dimethenamid)) 30 others, e.g. DCPA, dithiopyr, thiazopyr, pronamide; b) and as a racemic mixture (1RS, aRS). References herein to inhibitors of shoots of emerging seedlings i) dimethenamid refer to its various forms unless otherwise thiocarbamates, e.g. EPTC, butylate, cycloate, molinate, stated. Of the diastereomeric mixtures S-dimethenamid is pebulate, thiobencarb, triallate, vernolate; c) inhibitors of preferred. roots only of seedlings, e.g. bensulide, napropamide, The term herbicides, as used herein, refers to compounds 35 siduron; d) inhibitors of roots and shoots of seedlings, which combat or control undesired plant growth. This class including chloroacetamides e.g. alachlor, acetochlor, of compounds may be divided into sub-classes according to metolachlor, diethatyl, propachlor, butachlor, pretilachlor, the primary type or mode of action the herbicide has on the metazachlor, dimethachlor, and others e.g. cinmethylin plant. For example according to G. F. Warren of Purdue 6. amino acid synthesis inhibitors, including a) glyphosate, University, Indiana, USA, herbicides can be classified as glufosinate; b) sulfonylureas, e.g. rimsulfuron, auxin transport inhibitors, growth regulator herbicides, pho metsulfuron, nicosulfuron, triasulfuron, primisulfuron. tosynthesis inhibitors, pigment inhibitors, growth inhibitors, bensulfuron, chlorimuron, chlorsulfuron, sulfometuron, amino acid synthesis inhibitors, lipid biosynthesis inhibitors, thifen sulfuron, tribehuron, ethanetsulfuron, cell wall biosynthesis inhibitors, rapid cell membrane dis trifusulfuron, clopyrasulfuron, pyrazasulfuron, prosulfu ruptors as well as "miscellaneous" herbicides which do not 45 ron (CGA-152005), halosulfuron, metsulfuron-methyl, come under one of the preceding categories. chlorimuron-ethyl; c) sulfonamides, e.g. flumetsulam It has now surprisingly been found that co-application of (a.k.a. DE498); d) imidazolinones, e.g. imazaquin, dimethenamid and at least one other herbicide results in imazamethabenz, imazapyr, imazethapyr, imazmethapyr better and in some cases longer-lasting control of undesired 7. lipid biosynthesis inhibitors, including a) plant growth. This synergistic effect exhibits itself in a high cyclohexanediones, e.g. sethoxydim, clethodim; b) degree of control at co-application rates which are signifi aryloxyphenoxys, e.g. fluazifop-(P-butyl), diclofop cantly lower than the rate of each individual compound methyl, haloxyfop-methyl, quizalofop; c) others e.g. required to obtain the same degree of control. Furthermore, fenoxaprop-ethyl at any given co-application rate the degree of control is 8. cell wall biosynthesis inhibitors, e.g. dichlobenil, isoxa higher than the additive effect obtained for the individual 55 ben components at the same rate. In some cases both speed of 9. rapid cell membrane disruptors, including a) activity and level of control are enhanced and/or weeds can bipyridiliums, e.g. paraquat, diquat; b) diphenyl ethers, be controlled which are not controlled by either component e.g. acifluorfen, fomesafen, lactofen, oxyfluorfen; c) at economical rates. glutamine synthetase inhibitors, e.g. glufosinate; d) This synergistic effect allows for satisfactory control at others, e.g. oxadiazon reduced application rates for each component and even at