Herbicidal Composition and Method of Weed Control
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Europäisches Patentamt *EP000888055B1* (19) European Patent Office Office européen des brevets (11) EP 0 888 055 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: A01N 43/54 of the grant of the patent: 30.08.2000 Bulletin 2000/35 (86) International application number: PCT/EP97/01106 (21) Application number: 97908179.1 (87) International publication number: (22) Date of filing: 05.03.1997 WO 97/34484 (25.09.1997 Gazette 1997/41) (54) HERBICIDAL COMPOSITION AND METHOD OF WEED CONTROL HERBIZIDE ZUSAMMENSETZUNG UND DEREN VERWENDUNG ZUR UNKRAUTBEKÄMPFUNG COMPOSITION HERBICIDE ET PROCEDE DE LUTTE CONTRE LES MAUVAISES HERBES (84) Designated Contracting States: (72) Inventors: AT BE CH DE ES FR GB GR IT LI NL PT • HUDETZ, Manfred CH-4310 Rheinfelden (CH) (30) Priority: 15.03.1996 CH 69196 • NELGEN, Robert D-55270 Jugenheim (DE) (43) Date of publication of application: 07.01.1999 Bulletin 1999/01 (56) References cited: DE-A- 4 437 197 US-A- 5 183 492 (73) Proprietors: • Novartis AG 4058 Basel (CH) Designated Contracting States: BE CH DE ES FR GB GR IT LI NL PT • Novartis-Erfindungen Verwaltungsgesellschaft m.b.H. 1235 Wien (AT) Designated Contracting States: AT Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 0 888 055 B1 Printed by Jouve, 75001 PARIS (FR) EP 0 888 055 B1 Description [0001] The present invention relates to a novel herbicidal composition comprising a herbicidal active ingredient com- bination that is suitable for the selective control of weeds in crops of useful plants, such as cereals, maize, rice, sugar 5 cane, plantation crops, cotton, potatoes and soybean crops. [0002] The invention relates also to a method of controlling weeds in crops of useful plants and to the use of the novel composition for that purpose. [0003] Herbicidal compositions that comprise the compound of formula A 10 15 20 are described, for example, in US-A-5 183 492. [0004] It has now surprisingly been shown that a combination of variable proportions of the compound of formula A with one compound selected from glyphosate, terbuthylazine, atrazine, metolachlor, metolachlor (S-enantiomer), dimethenamid, glufosinate and paraquat exhibits a herbicidal activity that renders possible effective control, both pre- 25 emergence and post-emergence, of the majority of weeds that occur especially in crops of useful plants, without any significant damage being done to the useful plants. [0005] In accordance with the present invention there is therefore proposed a novel herbicidal composition for se- lective weed control that comprises, in admixture with one another, the compound of formula A 30 35 40 or an agrochemically acceptable salt thereof as active ingredient, and a synergistically effective amount of a compound selected from glyphosate, terbuthylazine, atrazine, metolachlor, metolachlor (S-enantiomer), dimethenamid, glufosinate and paraquat. 45 [0006] It is extremely surprising that the combination of the compound of formula A with a synergistically effective amount of a compound selected from glyphosate, terbuthylazine, atrazine, metolachlor, metolachlor (S-enantiomer), dimethenamid, glufosinate and paraquat exceeds the additive effect on the weeds to be controlled that is to be expected in principle, and thus broadens the range of activity of the two preparations especially in the following two respects: [0007] First, the rates of application of the individual compounds are reduced while the good action remains un- 50 changed. Secondly, the composition according to the invention achieves a high degree of weed control even where the individual substances have become no longer usable agronomically at low rates of application. The result is a substantial broadening of the weed spectrum and an additional increase in selectivity for the crops of useful plants, which is desirable and necessary should an unintentional overdose of active ingredient be applied. [0008] The herbicidal mixture according to the invention can be used against a large number of agronomically im- 55 portant weeds, such as Veronica, Galium, Papaver, Solanum, Chenopodium, Amaranthus, Xanthium, Abutilon, Am- brosia, Sagitaria, Setaria, Digitaria, Echinochloa, Ipomoea, Cassiastora, Datura stramonium, Sesbania exaltata and Sida spinosa in crops of useful plants. It has also been shown that after application of the compositions according to the invention the compound of formula A contained therein is broken down more rapidly in the useful plants treated, 2 EP 0 888 055 B1 especially maize, than metolachlor, which is an important advantage. [0009] The compositions according to the invention are suitable for all methods of application customary in agricul- ture, such as pre-emergence application, post-emergence application and seed dressing. [0010] The herbicidal mixture according to the invention is suitable especially for weed control in crops of useful 5 plants such as cereals, sugar cane, plantation crops (TVM), rice, cotton, soybeans, potatoes and, especially, maize, and also for dessication (drying out) or defoliation, for example for the purpose of facilitating harvesting, for example in cotton and potato crops. [0011] "Crops" is also to be understood as meaning crops that have been made tolerant to herbicides and classes of herbicides by conventional breeding or genetic engineering methods. 10 [0012] The active ingredient combination according to the invention comprises the compound of formula A and the compound selected from glyphosate, terbuthylazine, atrazine, metolachlor, metolachlor (S-enantiomer), dimethena- mid, glufosinate and paraquat in a synergistically effective ratio, but usually with an excess of one component over the other(s). Preferred mixing ratios of the compound of formula A with its mixing partners are generally from 100 : 1 to 1 : 100. 15 [0013] The above-mentioned active ingredient combinations are suitable especially for use in maize. [0014] The following active ingredient combinations may be used specifically for maize that is resistant to imida- zolinone herbicides: compound of formula A + glyphosate, compound of formula A + glufosinate. [0015] Other active ingredient combinations according to the invention may be used, for example in potato and cotton 20 crops, as dessicators or defoliants for the purpose of facilitating harvesting, for example compound of formula A + glufosinate or in no-till-maize and plantation crops (TVM), for example compound of formula A + glufosinate, compound of formula A + glyphosate, and compound of formula A + paraquat. [0016] The above-mentioned active ingredients are described and characterised in "The Pesticide Manual", Tenth Edition, 1994, Crop Protection Publications, and other customary agronomical technical literature. The compound of 25 formula A is described, for example, in US-A-5 183 492. [0017] The optical isomer (S-enantiomer) of metolachlor suitable in accordance with the invention is aRS,1'S(-)-N- (1'-methyl-2'-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniline of formula Va 30 35 and also its agrochemically acceptable salts, which are described, for example, in US-A-5 002 606. 40 [0018] The rate of application of the active ingredients may vary within wide limits and depends on the nature of the soil, the type of use (pre- or post-emergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the weed to be controlled, the prevailing climatic conditions, and other factors determined by the type of use, time of use and target crop. Generally, the active ingredient mixture according to the invention can be applied at a rate of application of from 50 to 4000 g of active ingredient mixture/ha. 45 [0019] In the composition according to the invention, the component of formula A is present in a ratio by weight of from 1: 100 to 1 : 0.001 to a mixing partner selected from glyphosate, terbuthylazine, atrazine, metolachlor, metolachlor (S-enantiomer), dimethamid, glufosinate and paraquat. [0020] The compositions according to the invention may be used in unmodified form, that is to say as obtained in the synthesis, but they are preferably formulated in customary manner together with the adjuvants customarily em- 50 ployed in formulation technology, e.g. into emulsifiable concentrates, provided sulfonylureas are not present, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcap- sules. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. [0021] The formulations, that is to say the compositions, preparations or mixtures comprising the compounds (active 55 ingredients) of formulae A the mixing partners and/or one or more solid or liquid formulation adjuvants, are prepared in a manner known per se, e.g. by homogeneously mixing and/or grinding the active ingredients with the formulation adjuvants, for example solvents or solid carriers. It is also possible in addition to use surface-active compounds (sur- factants) in the preparation of the formulations. 3 EP 0 888 055 B1