USOO9049866B2 (12) United States Patent (10) Patent No.: US 9,049,866 B2 Refardt et al. (45) Date of Patent: Jun. 9, 2015 (54) SYNERGISTIC HERBICIDAL COMBINATION (58) Field of Classification Search OF CLOMAZONE AND PETHOXAMD CPC ... A01N 43/80: A01N37/20: A01N 2300/00 USPC .......................... 504/138, 140,271, 342, 111 (75) Inventors: Matthias Refardt, Ettingen (CH): See application file for complete search history. Casper Reinhard Christensen, Holstebro (DK) (56) References Cited (73) Assignee: CHEMINOVA A/S, Lemvig (DK) U.S. PATENT DOCUMENTS 4,405.357 A 9/1983 Chang (*) Notice: Subject to any disclaimer, the term of this 4,895,587 A * 1/1990 Kato et al. .................... 504,289 patent is extended or adjusted under 35 5,583,090 A 12/1996 Stern et al. U.S.C. 154(b) by 392 days. 5,597,780 A 1/1997 Lee et al. 2003, OO69137 A1 4/2003 Almsick et al. (21) Appl. No.: 12/991,499 FOREIGN PATENT DOCUMENTS (22) PCT Filed: May 7, 2009 EP O 206251 12, 1986 (86). PCT No.: PCT/DK2O09/OOO 105 WO WO 2009115433 A2 * 9, 2009 S371 (c)(1), OTHER PUBLICATIONS (2), (4) Date: Nov. 11, 2010 Colby, S.R., "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations'. Weed Science Society of America, vol. 15. (87) PCT Pub. No.: WO2009/135492 No. 1. (Jan. 1967), pp. 20-22. PCT Pub. Date: Nov. 12, 2009 * cited by examiner (65) Prior Publication Data Primary Examiner — John Pak US 2011 FOO59849 A1 Mar. 10, 2011 Assistant Examiner — Andriae M Holt (30) Foreign Application Priority Data (74) Attorney, Agent, or Firm — Leydig, Voit & Mayer, Ltd. May 9, 2008 (DK) ................................. 2008 OO667 (57) ABSTRACT Presented are herbicidal compositions comprising as active (51) Int. Cl. ingredients clomaZone and pethoxamid. The combinations of AOIN 43/80 (2006.01) these herbicidal active compounds show a synergistic effect AOIN37/20 (2006.01) in the control of harmful plants. (52) U.S. Cl. CPC ...................................... A0IN 43/80 (2013.01) 19 Claims, No Drawings US 9,049,866 B2 1. 2 SYNERGISTC HERBICIDAL COMBINATION harmful plants are exposed to an effective amount of a syn OF CLOMAZONE AND PETHOXAMD ergistic combination of the compound A and the compound B. The present invention relates to herbicidal compositions In yet another embodiment, the invention relates to a her comprising as active ingredients the compound A which is bicidal composition comprising a herbicidal effective amount clomazone and the compound B which is pethoxamid. The of the compound A which is clomaZone and the compound B combinations of these active compounds show a synergistic which is pethoxamid. In a preferred embodiment the herbi effect in the control of harmful plants. The invention further cidal composition comprise a herbicidal effective amount of relates to a method for the control of harmful plants, such as the compound A and the compound B wherein the active weeds in crops of useful plants, and to the use of the herbicidal 10 components A and B are present in a synergistically effective compositions for that purpose. amount. The composition is preferably selected among those compositions comprising a form selected from the group BACKGROUND consisting of ready-to-use solutions, emulsifiable concen trates, emulsions, Suspensions, wettable powders, soluble The herbicidal active compound clomazone is known from 15 powders, granules, soluble granules, dispersible granules, U.S. Pat. No. 4,405.357 and is generally used to control microemulsions, microcapsule Suspensions and mixtures weeds in various crops. The herbicidal active compound thereof. pethoxamid is known from European patent application no. In a further embodiment, the invention relates to a method EP 206251-A1 and is generally used to control weeds in of reducing the Volatility of clomaZone, said method compris various crops such as control of grass weeds and broad-leaved ing combining clomaZone as compound A with a compound weeds. B which is pethoxamid, preferably in a herbicidal composi ClomaZone is known to be a very volatile organic com tion as described herein. Preferably the ratio between the pound to an extend so that clomaZone applied in a target area compounds A and B is in a ratio as to reduce the volatility of may move to adjacent areas and there cause discoloration, clomaZone on a comparative scale to an emulsifiable concen most typically whitening or some degree of bleaching, of a 25 trate composition comprising a similar amount of clomaZone variety of crops, trees, or decorative plants. While this bleach and without the compound B being present. Preferable com ing may be temporary when plants are exposed to Sufficiently pounds A and B are present in a herbicidal effective amount low concentrations, it is undesirable even when not causing but the compound B need not necessarily be present so as to the destruction of the affected plant. Accordingly appropriate produce a synergistic effect with the compound A. However, use instructions for clomaZone is often found on product 30 in a very preferred embodiment, the method of reducing the labels of commercially available clomaZone products and in Volatility of clomaZone comprise combining clomaZone as particular on emulsifiable concentrates formulations com compound A with a compound B which is pethoxamid, in a prising clomaZone in order to prevent exposure to clomaZone ratio as to reduce the volatility of the clomazone while main sensitive plants. Methods of reducing the volatility of cloma taining a synergistic herbicidal effect and without Substan Zone, i.e. to prevent or reduce vapor transfer of clomaZone to 35 tially sacrificing the overall herbicidal activity. Such ratios are plants which are not target of application, are proposed in preferably as herein described. Thus, the present invention U.S. Pat. Nos. 5,597,780 and 5,583,090 in which encapsula relates to a herbicidal composition having reduced cloma tion techniques are applied as to prepare microcapsule Sus Zone vapour transfer comprising a compound A which is pension formulations of clomaZone. clomaZone and a compound B which is pethoxamid and pref In crop protection products, it is always desirable to 40 erably the composition comprise a herbicidal effective increase the specific activity of an active ingredient and the amount of the compound A and the compound B wherein the reliability of action. It is an object of the present invention to active components A and B are present in a synergistically provide mixtures which comprise a compound A which is effective amount. Such ratios and amounts are preferably as clomaZone, and the compound B which is pethoxamid which herein described. are selective in crops to control undesirable harmful plants. 45 The compositions according to the invention can be Surprisingly, it has now been found that combinations of employed for the selective control of grasses and annual and these active compounds exhibits a synergistic effect when perennial monocotyledonous and dicotyledonous harmful used for the control of harmful plants. Further it has been plants the presence of useful plants such as maize, soya, peas, found that by combining clomaZone with pethoxamid the beans, Sunflowers, oilseed rape, Sugar cane, cassava, pump Volatile nature of clomaZone is significantly reduced. 50 kins, potatoes, vegetables and tobacco. Within the scope of this invention is also the control of such harmful plants found DESCRIPTION OF THE INVENTION among transgenic useful plants or among useful plants selected by classical means which are resistant to the active In one embodiment, the invention relates to a method for compounds A and B. Likewise, the compositions can be controlling harmful plants comprising exposing said harmful 55 employed for controlling undesirable harmful plants in plan plants to an effective amount of a combination of the com tation crops. Among harmful plants, e.g. weeds or Volunteer pound A which is clomaZone, and the compound B which is crop plants, that may be controlled are Ambrosia artemisiifo pethoxamid. In a preferred embodiment the harmful plants lia, Amaranthus retroflexus, Apera spica-venti, Capsella are exposed to an effective amount of a synergistic combina bursa-pastoris, Chenopodium album, Convolvulus arvensis, tion of the compound A and the compound B. 60 Digitaria ischaemum, Digitaria sanguinalis, Echinochloa In another embodiment, the invention relates to a method crus-galli, Galium aparine, Lamium purpureum, Matricaria for controlling harmful plants in the presence of useful plants spp., Mercurialis annua, Myosotis arvensis, Poa spp., comprising exposing said harmful plants and useful plants to Polygonum convolvulus, Polygonum persicaria, Portulaca an effective amount of a combination of the compound A oleracea, Senecio vulgaris, Setaria geniculata, Solanum which is clomaZone, and the compound B which is pethoxa 65 nigrum, Stellaria media, Veronica persica and Viola arvensis. mid, it being understood that the useful plants remain Compositions containing the active compounds A and B unharmed after the exposure. In a preferred embodiment the may be employed in any conventional form, for example, in US 9,049,866 B2 3 4 the form of a twin pack, or ready-to-use Solutions, emulsifi essential. Likewise, any form of combination of the active able concentrates, emulsions, Suspensions, wettable powders, components may be applied for either pre- or post-emergence soluble powders, granules, soluble granules, dispersible control of harmful plants, e.g. weeds in crops of useful plants. granules, microemulsions, microcapsule Suspensions e.g. Rates of application of the composition will vary according capsules comprising both active ingredients or present within 5 to prevailing conditions such as targeted weeds, degree of separate capsules; and mixtures thereof Such as a ZC, ZE or infestation, weather conditions, Soil conditions, crop species, ZW formulation. Such compositions can beformulated using mode of application, and application time. Compositions adjuvants and formulation techniques that are known in the containing the active compounds may be applied in the man art for individually formulating the herbicides.