EP1651046A1 - Combinaisons herbicides ternaires - Google Patents

Combinaisons herbicides ternaires

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Publication number
EP1651046A1
EP1651046A1 EP04741027A EP04741027A EP1651046A1 EP 1651046 A1 EP1651046 A1 EP 1651046A1 EP 04741027 A EP04741027 A EP 04741027A EP 04741027 A EP04741027 A EP 04741027A EP 1651046 A1 EP1651046 A1 EP 1651046A1
Authority
EP
European Patent Office
Prior art keywords
plants
herbicides
salts
acid
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04741027A
Other languages
German (de)
English (en)
Inventor
Erwin Hacker
Martin Hess
Frédéric Top
Wolfgang Benz
Markus Dollinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1651046A1 publication Critical patent/EP1651046A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

  • the invention is in the technical field of crop protection agents which are used against harmful plants e.g. can be used in plant crops and contain a combination of at least three herbicides as active ingredients.
  • the effectiveness of these herbicides against harmful plants in plant crops is at a high level, but generally depends on the application rate, the particular form of preparation, the harmful plants to be controlled or the range of harmful plants, the climatic and soil conditions, etc. Another criterion is the duration of action or the rate of degradation of the herbicide. If necessary, changes in the sensitivity of harmful plants that may occur with extended use of the herbicides or geographically limited must also be taken into account. Impact on individuals
  • Harmful plants can only be compensated for to a limited extent by higher application rates of the herbicides, e.g. B. because the selectivity of the herbicides is often deteriorated or there is no improvement in effectiveness even with a higher application rate. In some cases, the selectivity in cultures can be improved by adding safeners. In general, however, there is always a need for methods to achieve the herbicidal action with a lower application rate of active compounds.
  • a lower application rate not only reduces the amount of an active ingredient required for the application, but generally also reduces the amount of formulation auxiliaries required. Both reduce the economic effort and improve the ecological compatibility of herbicide treatment.
  • One way to improve the application profile of a herbicide is to combine the active ingredient with one or more other active ingredients consist.
  • phenomena of physical and biological incompatibility often occur when several active ingredients are used in combination, e.g. B. lack of stability in a co-formulation, decomposition of an active ingredient or antagonism of the active ingredients.
  • combinations of active substances with a favorable activity profile, high stability and, as far as possible, synergistically enhanced activity are desired, which allow a reduction in the application rate compared to the individual application of the active substances to be combined.
  • the group of hydroxybenzonitriles and phenylsulfonylaminocarbonyltriazolinones interact in a particularly advantageous manner, e.g. if they are used in plant crops in which the herbicides, if appropriate with the addition of
  • Safeners can act selectively.
  • the herbicide combinations according to the invention have a herbicidally active content of components (A), (B) and (C) and can contain further components, for. B. agrochemical active substances of another type and / or additives and / or formulation auxiliaries customary in crop protection, or used together with these. Herbicide combinations are preferred which have a synergistically active content of components (A), (B) and (C).
  • the herbicide combinations according to the invention have synergistic effects.
  • the synergistic effects can be observed, for example, when the active ingredients (A), (B) and (C) are applied together, but they can often also be found when the active ingredients are applied at different times (splitting application).
  • Preferred is the simultaneous or prompt application of the active compounds of the herbicide combination according to the invention.
  • the synergistic effects allow a reduction in the application rates of the individual active ingredients, a higher potency with the same application rate, the control of previously unrecognized species (gaps), an extension of the application period and / or a reduction in the number of necessary individual applications and - as a result for the user - economically and more environmentally friendly weed control systems.
  • the formulas (I), (II) and (III) mentioned comprise all stereoisomers and their mixtures, in particular also racemic mixtures, and - if enantiomers are possible - the biologically active enantiomers in each case.
  • Compounds of formula (I) and (III) and their salts and their preparation are e.g. described in EP-A-053011 and US 5,534,486.
  • Compounds of formula (II) and their salts and esters and their preparation are e.g. described in US 3,397,054.
  • a preferred compound of the formula (I) and its salts is diflufenican (A1) (see, for example, Pesticide Manual, 10th edition 1994, pp. 335-336).
  • Preferred compounds of the formula (II) are loxynil and its salts and esters (see, for example, 4-hydroxy-3,5-diiodobenzonitrile, Pesticide Manual, 10th edition 1994, pp.
  • metal salts such as alkali metal salts and Carbonklareester such as C4- ⁇ 0 carboxylic acid esters, for example, ioxynil (B1), ioxynil octanoate, (B2), ioxynil-sodium (B3) and ioxynil-potassium (B4).
  • Preferred compounds of the formula (III) and their salts are methyl 2 - ( ⁇ [(4-methyl-5-oxo-3-propoxy-4,5-dihydro-1 H-1, 2,4-triazol-1-yl ) carbonyl] amino ⁇ sulfonyl) benzoate (propoxycarbazone, C1) and its salts such as the sodium salt (propoxycarbazone sodium, C2) (see, for example, US 5,534,486 and Z. PfIKrankh. PflSchutz, Sonderh. XVII, 545-553 (2000)).
  • the application rate of the active compounds of the formulas (I), (II) and (III) and their salts can vary within wide limits, for example between 0.001 and 2.5 kg of AS / ha. Insofar as the abbreviation AS / ha is used in this description, this means “active substance per hectare”, based on 100% active ingredient.
  • the application rates are generally lower, for. B. in the range of 0.1 to 900 g ai / ha, preferably 0.5 to 750 g ai / ha.
  • the active ingredients can e.g. as water-soluble wettable powder (WP), water-dispersible granulate (WDG), water-emulsifiable granulate (WEG), suspoemulsion (SE) or old dispersion concentrate (e.g. oil suspension concentrate) (OD).
  • WP water-soluble wettable powder
  • WDG water-dispersible granulate
  • WEG water-emulsifiable granulate
  • SE suspoemulsion
  • old dispersion concentrate e.g. oil suspension concentrate
  • the weight ratio of components (A) and (B) to one another is generally 50: 1-1: 100, preferably 25: 1-1: 25.
  • the weight ratio (A + B): C is generally 3000: 1-1 : 10, preferably 800: 1 - 1: 5.
  • Suitable safeners are e.g. known from WO-A-96/14747 and the literature cited therein.
  • the following groups of compounds are suitable, for example, as safeners for the herbicidal active ingredients (A), (B) and (C) mentioned above: a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid (S1) type, preferably compounds such as 1- (2, 4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S1-1, mefenpyr-diethyl, PM, S 594-595), and " related " compounds as described, for example, in WO 91/07874 and PM (pp.
  • dichlorophenylpyrazole carboxylic acid preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (S1-2), 1- (2,4-dichlorophenyl) -5-isopropyl-pyrazole-3-carboxylic acid ethyl ester (S1-3), 1- (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) pyrazole-3- ethyl carboxylate (S1-4), 1- (2,4-dichlorophenyl) -5-phenyl-pyrazole-3-carboxylic acid ethyl ester (S1-5) and related compounds as described in EP-A-333 131 and EP-A -269 806 are described.
  • active substances of the phenoxyacetic or propionic acid derivative or aromatic carboxylic acid type such as, for example, 2,4-dichlorophenoxyacetic acid (ester) (2,4-D), 4-chloro-2-methylphenoxy-propionester (mecoprop) , MCPA or 3,6-dichloro-2-methoxy-benzoic acid (ester) (Dicamba).
  • active substances of the pyrimidine type such as "Fenclorim" (PM, pp.
  • 450-451 2-chloro 4-trifluoromethyl-1, 3-thiazole-5-carboxylic acid benzyl ester
  • m active substances of the type of naphthalenedicarboxylic acid derivatives, which are known as seed dressings, such as, for example, “Naphthalic anhy drid "(PM, pp.
  • the herbicides (A), (B) and (C) are suitable, if appropriate in the presence of safeners, for combating harmful plants in crops, for example in economically important crops such as cereals (for example wheat, barley, rye, Oats, rice, maize, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, of particular interest being the use in monocotyledon crops such as cereals, in particular wheat, barley, rye, oats, and crosses thereof such as triticale, rice, corn and millet
  • cereals for example wheat, barley, rye, Oats, rice, maize, millet
  • sugar beet sugar beet
  • sugar cane rapeseed
  • cotton and soybeans of particular interest being the use in monocotyledon crops
  • cereals in particular wheat, barley, rye, oats, and crosses thereof such as triticale, rice, corn and millet
  • the invention also includes those herbicide combinations which, in addition to components (A), (B) and (C), also comprise one or more further agrochemical active compounds of another structure, such as herbicides, insecticides, fungicides or safeners, preferably herbicides.
  • herbicide combinations which, in addition to components (A), (B) and (C), also comprise one or more further agrochemical active compounds of another structure, such as herbicides, insecticides, fungicides or safeners, preferably herbicides.
  • herbicides from group (D) are herbicides from group (D), the herbicides from the group of the compounds consisting of (indication with the "common name” and a reference point, eg., Selectively in some monocotyledon crops against monocotyledon and / or dicotyledonous harmful plants) from "The Pesticide Manual” 12th Ed., British Crop Protection Council 2000, abbreviated “PM” ⁇ ⁇ ⁇ ⁇ or from “" Th-rPesticide Manual "10th edition 1994, British Crop Protection Council) - 30 (D1) iodosulfuron, in particular also comprising its salts and esters, for example 3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -1- (2-methoxycarbonyl-5-iodophenylsulfonyl) urea (iodosulfuron-methyl) and its salts like that Sodium salt (iodosulfuron-methyl-sodium
  • Imazamox in particular also comprising its esters and salts such as the sodium salt (PM, p. 528), for example (RS) -2- (4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) -5 -methoxymethylnicotinic acid, (application rate in general: 1 - 500 g ai / ha, preferably 2 - 200 g ai / ha), (D3) florasulam, in particular also comprising its salts such as the sodium salt (PM, pp.
  • halosulfuron in particular also comprising its esters such as halosulfuron-methyl and its salts such as the sodium salt (PM, pp.
  • (D7) cinidon-ethyl, in particular also comprising its salts such as the sodium salt (PM, pp. 181-182), for example ethyl (Z) -2-chloro-3- [2-chloro-5- (1,2-cyclohex -1-enedicarboximido) phenyl] acryIate, (application rate in the old fine: " ⁇ - 500 g AS / ha, " preferably 5 - 20CTg AS / ha), ⁇ (D8) mesotrione (PM, p. 602), e.g.
  • (D11) flufenacet in particular also comprising its salts such as the sodium salt (PM, pp. 434-435), e.g. 4'-fluoro-N-isopropyl-2- (5-trifluoromethyl-1, 3,4-thiadiazol-2-yloxy) acetanilide, (application rate in general: 50-5000 g ai / ha, preferably 150-2000 g ai / Ha),
  • (D12) flumetsulam in particular also comprising its salts such as the sodium salt (PM, pp. 438-439), e.g. 2 ', 6'-difluoro-5-methyl [1, 2,4] triazolo [1,5-a] pyrimidine-2-sulfonanilide, (application rate in general: 5-1000 g ai / ha, preferably 10-600 g AS / ha)
  • (D13) flupoxam in particular also comprising its salts such as the sodium salt (PM, p. 999), e.g. 1- [4-Chloro-3- (2,2,3,3,3-pentafluoropropoxymethyl) phenyl] -5-phenyl-1 H-1, 2,4-triazole-3-carboxamide, (application rate in general: 5 - 5000 g ai / ha, preferably 20 - 3000 g ai / ha),
  • (D14) prosulfocarb in particular also comprising its salts (PM, pp. 786-787), e.g. S-benzyl dipropylthiocarbamate, (application rate in general: 50-5000 g ai / ha, preferably 200-3000 g ai / ha), (D15) flurtamone, in particular also comprising its salts such as the sodium salt (PM, p. 459), e.g.
  • 441-442 are known (application rate in general: 10-300 g ai / ha, preferably 15-200 g ai / ha), (D18) isoproturon, for example 3- (4-isopropylphenyl) -1, 1-dimethylurea pesticide manual , 10th edition 1994, pp. 611-612, (application rate in general: 50 - 5000 g ai / ha, preferably 100 - 4000 g ai / ha),
  • diclofop e.g. (r? S) -2- [4- (2,4-dichlorophenoxy) phenoxy] propionic acid including i.a. the most important form of use is the methyl ester, the diclofop-methyl, Pesticide Manual, 10th ed. 1994, pp. 315-317 (application rate in general: 100-3000 g ai / ha, preferably 200-2000 g ai / ha),
  • (D20) clodinafop e.g. (R) -2- [4- (5-chloro-3-fluoro-2-pyridyloxy) phenoxy] propionic acid, in particular also comprising the use form as clodinafop-propargyl, Pesticide Manual, 10th edition 1994, pp. 216-217, (Application rate in general: 1 - 150 g ai / ha, preferably 5 - 100 g ai / ha), (D21) chlorotoluron, e.g. 3- (3-chloro-p-tolyl) -1,1-dimethylurea, Pesticide Manual, 10th ed. 1994, pp.
  • (D23) Imazamethabenz e.g. reaction product, comprising ( ⁇ ) -6- (4-isopropyl-4-methyl-4-oxo-2-imidazolin-2-yl) -t? 7-toluic acid and ( ⁇ ) -6- ( 4-Isopropyl-4-methyl-4-oxo-2-imidazoli ⁇ -2-yl) -toluic acid7 - whereby the esters, for example the methyl esters known under the name Imazamethabenz-methyl, can also be used, Pesticide Manual, 10th ed. 1994, pp.
  • Flamprop also comprising Flamprop-M, for example ⁇ / -Benzoyl- ⁇ / - (3-chloro-4- 0 fluorophenyl) -DL-alanine and ⁇ / -Benzoyl- / V- (3-chloro-4- fluorophenyI) -D-alanine, including, inter alia, Flamprop-methyl, Flamprop-M-methyl, Flamprop-M-isopropyl, Pesticide Manual, 10th ed.
  • MCPA for example (4-chloro-2-methylphenoxy) acetic acid
  • D29 MCPA-butotyl, MCPA-dimethylammonium, MCPA-isoctyl, MCPA-potassium , MCPA sodium, Pesticide Manual, 10th ed. 5 1994, pp.
  • dichloroprop comprising also dichloroprop-P, for example (RS) -2- (2,4-dichlorophenoxy) propionic acid and (r?) - 2- (2,4- - " ⁇ - - ⁇ OichlOrophenoxy) propionic acid, dichloroprop-0 are also commonly used butotyl, dichloroprop-ethyl ammonium, dichloroprop-iso-octyl, dichloroprop-potassium, Pesticide Manual, 10th ed. 1994, pp. 309-311 and 311-312, (ed in general: 10 - 5000 g ai / ha, preferably 20 - 3000 g AS / ha),
  • dicamba e.g. 3,6-dichloro-anisic acid, used inter alia as dicamba-dimethylammonium, dicamba-potassium, dicamba-sodium, dicamba-trolamine, Pesticide Manual, 10th edition 1994, pp. 298-300, (application rate in general: 20-500 g ai / ha, preferably 30-400 g AS / ha)
  • fluroxypyr e.g. 4-amino-3,5-dichloro-6-fluoro-2-pyridyloxyacetic acid, further use: fluoroxypyr-meptyl and particularly preferably: fluroxypyr-butoxypropyl ester, Pesticide Manual, 10th ed. 1994, pp. 505-507, (application rate in general: 20 - 500 g ai / ha, preferably 30 - 400 g ai / ha),
  • bromoxynil e.g. 3,5-dibromo-4-hydroxy-benzonitrile, frequently used as bromoxynil octanoate, bromoxynil potassium, Pesticide Manual, 10th ed. 1994, pp. 121-123, (application rate in general: 10 - 3000 g ai / ha , preferably 50 - 1500 g ai / ha),
  • (D37) fluoroglycofen for example 0- [5- (2-chloro- ⁇ , ⁇ , ⁇ -trifluoro-p-tolyloxy) -2-nitrobenzoylglycolic acid, further use: fluoroglycofen-ethyl, Pesticide Manual, 10th edition 1994, p 492-494, (application rate in general: 1 - 200 g ai / ha, preferably 2 - 150 g ai / ha) - " (D38) lactofen, for example ethyl 0- [5- (2-chloro- ⁇ , ⁇ , ⁇ -trifluoro-p-tolyloxy) -2-nitrobenzoyl] - DL-lactate, Pesticide Manual, 10th edition 1994, p.
  • (D42) amidosulfuron e.g. 1- (4,6-dimethoxypyrimidin-2-yl) -3-mesyl (methyl) sulfamoyl urea, Pesticide Manual, 10th edition 1994, pp. 34-35, (application rate in general: 0, 5-200 g ai / ha, preferably 1-100 g ai / ha),
  • (D43) metsulfuron for example 2- (4-methoxy-6-methyl-1, 3,5-triazin-2-ylcarbamoylsulfamoyl) benzoic acid, usually used as Metsulfuron-methyl, Pesticide Manual, 10th ed. 1994, pp.
  • D48 Flupyrsulfuron (DPX-KE459), e.g. methyl 2- (4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl) -6-trifluoromethylnicotinate, e.g. flupyrsulfuron-methyl-sodium (PM, pp. 447 - 448), (application rate in general : 1 - 120 g ai / ha, preferably 2 - 100 g ai / ha), (D49) fluazolates (MON 48500), e.g.
  • glufosinate including also glufosinate-P, for example 4- [hydroxy (methyl) phosphinoyl] -DL-homoalanine, 4- [Hydroxy (methyl) phosphinoyl] -L-homoalanine, each preferred as salts, for example ammonium or alkali metal salts such as glufosinate-ammonium, glufosinate-P-ammonium, glufos inate sodium or glufosinate P sodium can be used, Pesticide Manual, 10th ed.
  • Glyphosate for example ⁇ / - (phosphonomethyl) glycine, which is preferably used as glyphosate-isopropylammonium, glyphosate-sesquinatrium, glyphosate-trimesium, Pesticide Manual, 10th ed. 1994, pp.
  • 2- (4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) nicotinic acid (application rate in general: 1 - 500 g ⁇ """ AS / ha, preferably 2 - 300 g AS / ha), 0 (D61) Imazapic, in particular also comprising its esters and salts such as the sodium salt (PM, p. 529), for example (RS) -2- (4-isopropyl-4-methyl-5-oxo-2 imidazolin-2-yl) -5-methylnicot Acid, (application rate in general: 1 - 500 g ai / ha, preferably 2 - 300 g ai / ha).
  • herbicides D1, D2, D4, D8, D9, D11 - D16, D18, D21, D22, D23, D24, D27, D40, D43, D47 - D53, D58 - D61, D63 are suitable - D65 in particular for controlling monocotyledon and dicotyledonous harmful plants
  • the herbicides D17, D19, D20, D25, D26, D54-D56 are particularly suitable for controlling monocotyledonous harmful plants
  • the herbicides D3, D5, D6, D7, D10, D28 - D39, D41 , D42, D44, D45, D46, D57, D62 are particularly suitable for controlling dicotyledonous harmful plants.
  • Herbicide combinations containing the following compounds (A) + (B) + (C) and (A) + (B) + (C) + (D) are of particular interest:
  • each of the herbicide combinations mentioned above can also contain a 10 or more safener, in particular a safener such as mefenpyr-diethyl (S1-1), isoxadifen-ethyl (S1-9) and cloquintocet-mexyl (S2-1).
  • a safener such as mefenpyr-diethyl (S1-1), isoxadifen-ethyl (S1-9) and cloquintocet-mexyl (S2-1).
  • S1-1 mefenpyr-diethyl
  • S1-9 isoxadifen-ethyl
  • S2-1 cloquintocet-mexyl
  • herbicides (A) with one or more herbicides (B) and / or more herbicides (C), for example one Herbicide (A) with one herbicide (B) and one herbicide (C).
  • herbicide combinations according to the invention can be used together with other agrochemical active ingredients, for example from the group of safeners, fungicides, herbicides, in particular from the group of herbicides (D), insecticides and plant growth regulators or additives customary in crop protection, such as fertilizers and dyes and formulation auxiliaries, the above ranges of application rates and
  • the application rate ratio (A + B + C): D is generally 2500: 1-1: 500, preferably 1000: 1-1: 300.
  • Herbicide combinations with several herbicides D e.g. those containing the following herbicide combinations as component D): D35 + D29, D1 + D42, D1 + D65, D44 + D45, D43 + D45, D46 + D32, D33 + D35 or D48 + D57, preferably as components ( A), (B) and (C) the compounds (A1) + (B1) + (C1), (A1) + (B1) + (C2), (A1) + (B2) + (C1), (A1 ) + (B2) + (C2), (A1) + (B3) + (C1), (A1) + (B3) + (C2), (A1) + (B4) + (C1) or (A1) + (B4) + (C2), in particular (A1) + (B2) + (C2), are contained, and additionally a safener
  • the combinations according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants.
  • Perennial weeds that are difficult to control and that sprout from rhizomes, rhizomes or other permanent organs are also well captured by the active ingredients. It does not matter whether the substances are applied by pre-sowing, pre-emergence or post-emergence. Use in the post-emergence process or in the early post-sowing pre-emergence process is preferred.
  • Some representatives of the monocotyledonous and dicotyledon weed flocks are examples.
  • the cfiS should be able to control the compounds according to the invention without the name being intended to restrict them to certain species.
  • On the side of the monocotyledon weed species for example, Apera spica venti, Avena spp., Alopecurus spp., Brachiaria spp., Digitaria spp., Lolium spp., Echinochloa spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp , and Bromus spp.
  • the spectrum of activity extends to species such as Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp., Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharbitis spp., Polygonum spp., Sida spp., Sinapis spp ., Solanum spp., Stellaria spp., Veronica spp. and Viola spp., Xanthium spp., Paphaver rhoeas spp., Centaurea spp. on the annual side as well as Convolvulus, Cirsium, Rumex and Artemisia spp. in the perennial weeds.
  • the herbicide combinations according to the invention are applied to the surface of the earth before germination, either the weed seedlings emerge completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks ,
  • the herbicidal compositions according to the invention are notable for a rapid onset and long-lasting herbicidal action.
  • the rain resistance of the active ingredients in the combinations according to the invention is generally favorable.
  • a particular advantage is that the effective dosages of compounds (A), (B) and (C) used in the combinations can be set so low that their soil effect is optimally low. This makes their use not only possible in sensitive crops, but groundwater contamination is practically avoided.
  • the combination of active substances according to the invention enables a considerable reduction in the amount of active substances required.
  • the combinations according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous harmful plants, the crop plants are damaged only insignificantly or not at all.
  • some of the agents according to the invention have excellent growth-regulatory properties in the crop plants. They intervene regulating the plant's own metabolism and can thus be used to influence plant constituents in a targeted manner and to facilitate harvesting, for example by triggering desiccation and stunted growth.
  • they are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent crop losses during storage.
  • the agents according to the invention for controlling harmful plants can be used in genetically modified crops or crop plants obtained by mutation selection.
  • crop plants are generally distinguished by special advantageous properties, such as resistance to herbicidal compositions or resistance to plant diseases or pathogens causing plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • special properties concern e.g. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. For example, transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
  • transgenic crop plants which are resistant to other herbicides, for example sulfonylureas (US-A-5013659), transgenic crop plants with the ability to produce Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP- A-0142924, EP-A-0193259).
  • transgenic crop plants with modified fatty acid composition WO 91/13972).
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombining DNA sequences.
  • plasmids which allow mutagenesis or a sequence change by recombining DNA sequences.
  • base exchanges partial sequences removed or natural or synthetic sequences added.
  • adapters or linkers can be attached to the fragments.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example by expressing at least one corresponding antisense RNA, a sense RNA for achieving a CosuppreBsiöns bines ödertlie "expression of at least cleaves one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a particular compartment, z. B. the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1: 95-106 (1991).
  • the transgenic plant cells can be regenerated into whole plants using known techniques.
  • the transgenic plants can in principle be plants of any plant species, i.e. both monocot and dicot plants.
  • the present invention furthermore also relates to a process for controlling unwanted vegetation (for example harmful plants such as weeds or undesired crop plants), preferably in crops such as - fet ' reideT (for example wheat rye, rye, oats; hybrids thereof such as ritical rice, maize, Millet), sugar beet, sugar cane, rapeseed, cotton and soy, particularly preferably in monocot crops such as cereals, for example wheat, barley, rye, oats, crosses thereof such as triticale, rice, corn and millet, one or several herbicides of type (A) with one or more herbicides of type (B) and one or more herbicides of type (C) together or separately, for example pre-emergence, post-emergence or pre-post-emergence, on the plants, for example harmful plants, Plant parts, plant seeds or the area on which the plants 5 grow, for example the cultivated area applied.
  • unwanted vegetation for example harmful plants such as weeds or undesi
  • Undesirable plants are understood to mean all plants that grow in places where they are undesirable. This can e.g. Harmful plants (e.g. weeds or unwanted crops), e.g. also those that are resistant to certain 10 herbicidal active ingredients such as glyphosate, atrazine, glufosinate or imidazolinones.
  • Harmful plants e.g. weeds or unwanted crops
  • herbicidal active ingredients such as glyphosate, atrazine, glufosinate or imidazolinones.
  • the plant cultures can also be genetically modified or obtained by mutation selection and are preferably tolerant of 15 acetolactate synthase (ALS) inhibitors.
  • ALS acetolactate synthase
  • the invention also relates to the use of the herbicide combinations according to the invention of compounds (A) + (B) + (C) for controlling harmful plants, preferably in plant crops.
  • herbicidal compositions according to the invention can also be used non-selectively for controlling unwanted vegetation, e.g. in plantation crops, on roadsides, squares, industrial plants or railway systems.
  • the active substance combinations according to the invention can be used both as mixed formulations of components (A), (B) and (C), if appropriate with further agrochemical active substances, additives and / or customary * ---- . -_ -p ⁇ rr ⁇ iferu ⁇ gshJifsmJ teln are present, which are then diluted with water in the usual way ⁇ 30 to use, or prepared as so-called tank mixes by jointly diluting the separately formulated or partially separately formulated components with water.
  • the components (A), (B) and (C) can also be formulated separately and applied separately, so that the active compound combination according to the invention forms at the application site.
  • the compounds (A), (B) and (C) or their combinations can be formulated in 5 different ways, depending on which biological and / or chemical-physical parameters are specified.
  • Examples of general formulation possibilities are: wettable powder (WP), water-soluble concentrates, emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions, 0 sprayable Solutions or emulsions, suspension concentrates (SC), dispersions based on oil or water, suspoemulsions, dusts (DP), mordants, granules for soil or litter application or water-dispersible granules (WG), ULV formulations, microcapsules or waxes.
  • Combinations can also be made on the basis of these formulations with other agrochemical active ingredients, such as other herbicides, fungicides, insecticides, as well as safeners, fertilizers and / or growth regulators, for example in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also ionic or nonionic surfactants (wetting agents, dispersing agents), e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene sulfonic acid sodium or also oleoylmethyl tauric acid sodium.
  • ionic or nonionic surfactants e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates
  • Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more ionic or nonionic surfactants (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
  • ionic or nonionic surfactants emulsifiers
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid ester sorbate polyethylenefatty acid sorboxate, polyoxyethylene ethoxylate sorbate, polyoxyethylene ethoxylate sorbet, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene fatty acid sorbet
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • SC Suspension concentrates
  • SC can be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, where appropriate, “ further, if they ” are already listed above for the other “ types of formulation ” .
  • Emulsions for example oil-in-water emulsions (EW), can be used, for example, using stirrers, colloid mills and / or static mixers aqueous organic solvents and optionally other surfactants, such as those already listed above for the other types of formulation.
  • EW oil-in-water emulsions
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers. Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. For the production of plate, fluidized bed, extruder and spray granules, see e.g.
  • the agrochemical formulations generally contain 0.1 to 99 percent by weight, in particular 2 to 95% by weight, of active ingredients of types A and / or B and / or C, the following concentrations being customary depending on the type of formulation: the active ingredient concentration in wettable powders is for example about 10 to 95 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. Beie ⁇ nu1gie7l are ⁇ Ki- ⁇ iz ⁇ the Wirkstoffk ⁇ nzentratiori eg 5 to be "80% by weight. 7 Dust-like formulations contain at most 5 to 20 wt .-%
  • Active ingredient sprayable solutions about 0.2 to 25 wt .-% active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulating agents and fillers are used. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreezes and solvents, fillers, dyes and carriers, defoamers, evaporation inhibitors and agents which adjust the pH or Influence viscosity.
  • the herbicidal activity of the herbicide combinations according to the invention can be improved, for example, by surface-active substances, preferably by wetting agents from the range of fatty alcohol polyglycol ethers.
  • the fatty alcohol polyglycol ethers preferably contain 10 to 18 carbon atoms in the fatty alcohol residue and 2 to 20 ethylene oxide units in the polyglycol ether part.
  • the fatty alcohol polyglycol ethers can be nonionic or ionic, for example in the form of fatty alcohol polyglycol ether sulfates, which are used, for example, as alkali metal salts (for example sodium and potassium salts) or ammonium salts, or also as alkaline earth metal salts such as magnesium salts, such as C-
  • Nonionic fatty alcohol polyglycol ethers are, for example, 2 to 20, preferably 3 to 15, ethylene oxide units (C 10 -C 8 ), preferably (C 1 -C 0 ) fatty alcohol polyglycol ethers (for example isotridecyl alcohol polyglycol ether), for example from Genapol ® X series such as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 or Genapol ® X-150 (all from Clariant GmbH).
  • Genapol ® X series such as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 or Genapol ® X-150 (all from Clariant GmbH).
  • the present invention further comprises the combination of herbicides (A), (B) and (C) with the above-mentioned wetting agents from the series of fatty alcohol polyglycol ethers, which preferably contain 10 to 18 carbon atoms in the fatty alcohol residue and 2 to 20 ethylene oxide units in the polyglycol ether part contain and can be non-ionic or ionic (for example as fatty alcohol polyglycol ether sulfates).
  • Ci2 / C 14 fatty alcohol diglycol ether sulfate sodium are preferred, and Isotridecyl alcohol polyglycol ether, with 3 - 15 ethylene oxide units, e.g.
  • Genapol ® X series such as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 and Genapol ® X-150 (all from Clariant GmbH).
  • fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (e.g. fatty alcohol polyglycol ether sulfates) are also suitable as penetration aids and activity enhancers for a number of other herbicides, including herbicides from the imidazolinone series (see, for example, EP-A - 0502014).
  • fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (e.g. fatty alcohol polyglycol ether sulfates) are also suitable as penetration aids and activity enhancers for a number of other herbicides, including herbicides from the imidazolinone series (see, for example, EP-A -0,502,014).
  • the herbicidal activity of the herbicide combinations according to the invention can also be enhanced by using vegetable oils.
  • vegetable oils is understood to mean oils from oil-producing plant species such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, safflower oil or castor oil, in particular rapeseed oil, and their transesterification products, e.g. Alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
  • the vegetable oils are preferably esters of C ⁇ o-C 22 -, preferably C-i2-C 20 - fatty acids.
  • the C 10 -C 22 fatty acid esters are, for example, esters of unsaturated or saturated C 0 -C 22 fatty acids, in particular with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular C 8 fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • Cfo-C 22 fatty acids-EsTersihd ⁇ Ester7 ' which are obtained by r- reaction of glycerol or glycol with the C ⁇ o-C 22 fatty acids, such as those contained in oils from oil-producing plant species, or C ⁇ -C 2 o-Alkyl -C 0 C 22 fatty acid esters, such as those obtained, for example, by transesterification of the above-mentioned glycerol or glycol-C ⁇ o-C22- Fatty acid esters with C 2 -C 20 alcohols (for example methanol, ethanol, propanol or butanol) can be obtained.
  • the transesterification can be carried out according to known methods, as described, for example, in the Römpp Chemie Lexikon, 9th edition, volume 2, page 1343, Thieme Verlag Stuttgart.
  • Preferred C 1 -C 20 -alkyl-C 22 -C 22 fatty acid esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethyl hexyl esters and dodecyl esters.
  • Preferred as glycol and glycerol -CC 22 fatty acid esters are the uniform or mixed glycol esters and glycerol esters of -CC 22 fatty acids, in particular those fatty acids with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular C- i ⁇ fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • the vegetable oils can be present in the inventive herbicidal compositions, for example in the form of commercially available oil-containing formulation additives, in particular those (hereinafter referred Victorian Chemical Company, Australia, Hasten, main constituent: rapeseed oil ethyl ester) based on rapeseed oil such as Hasten ®, Actirob ® B (Novance, France, hereinafter Called ActirobB, main component: rapeseed oil methyl ester), Rako-Binol ® (Bayer AG, Germany, hereinafter called Rako-Binol, main component: rapeseed oil), Renol ® (Stefes, Germany, hereinafter referred to as Renol, vegetable oil component: rapeseed oil methyl ester) or Stefes Mero ® (Stefes , Germany, hereinafter called Mero, main ingredient: rapeseed oil methyl ester).
  • Oil-containing formulation additives in particular those (hereinafter
  • Combinations of herbicides (A), (B) and (C) with the vegetable oils mentioned above such as rapeseed oil preferably in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ® (Victofiän Che ⁇ ica eornp ⁇ a ⁇ y Ausfrä.ie ⁇ r hereinafter referred to as, - Main ingredient: rapeseed oil ethyl ester), Actirob ® B (Novance, France, hereinafter called ActirobB, main ingredient: rapeseed oil methyl ester), Rako-Binol ® (Bayer AG, Germany, hereinafter called Rako-Binol, main ingredient: rapeseed oil), Renol ® (Stefes, Germany, hereinafter called Renol, vegetable oil component: rapeseed oil methyl ester) or Stefes Mero ® (Stefes, Germany, hereinafter called Mero
  • the formulations present in the commercial form are optionally diluted in the customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
  • Preparations in the form of dust, ground granules or granules for spreading, and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the active compounds can be applied to the plants, parts of plants, plant seeds or the area under cultivation (arable soil), preferably to the green plants and parts of plants and, if appropriate, additionally to the arable soil.
  • arable soil preferably to the green plants and parts of plants and, if appropriate, additionally to the arable soil.
  • One possible application is the joint application of the active ingredients in the form of tank mixes, the optimally formulated concentrated formulations of the individual active ingredients being mixed together with water in the tank and the spray liquor obtained being applied.
  • a common herbicidal formulation of the combination according to the invention of active ingredients (A), (B) and (C) generally has the advantage of being easier to use.
  • a dusting agent is obtained by mixing 10 parts by weight of an active substance / active substance mixture and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a readily water-dispersible wettable powder is obtained by mixing 25 wt ⁇ ⁇ parts-% fr ⁇ es "" drug / Wifkstoffgemischs, 64 wt. -Teile- kaolin-containing quartz as inert substance, 10 parts by wt. of potassium lignosulfonate and 1 wt - Mixes sodium oleoylmethyl tauric acid as a wetting and dispersing agent and grinds it in a pin mill.
  • a readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of an active compound / active compound mixture with 6 parts by weight of alkylphenol polyglycol ether (Triton ® X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 wt. Parts of paraffinic mineral oil (boiling range approx. 255 to 277 ° C) and ground in a friction ball mill to a fineness of less than 5 microns.
  • alkylphenol polyglycol ether Triton ® X 207
  • isotridecanol polyglycol ether 8 EO
  • Parts of paraffinic mineral oil (boiling range approx. 255 to 277 ° C) and ground in a friction ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of an active ingredient / active ingredient mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
  • a water-dispersible granulate is obtained by mixing 75 parts by weight of an active ingredient / active ingredient mixture, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin , grinds on a pin mill and granulates the powder in a fluidized bed by spraying water as the granulating liquid.
  • a water-dispersible granulate is also obtained by adding 25 parts by weight of an active ingredient / active ingredient mixture, 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, 2 parts by weight of oleoylmethyl tauric acid sodium , 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water and vofzeTkleinert, then ground in a bead mill and the suspension thus obtained is atomized and dried in a spray tower using a single-component nozzle.
  • B. Biological examples are also obtained by adding 25 parts by weight of an active ingredient / active ingredient mixture, 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, 2 parts by weight of oleoylmethyl tauric acid sodium , 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water and vo
  • the seeds or rhizome pieces of the harmful plants and useful plants were laid out or were present in the soil and grown under natural outdoor conditions.
  • the treatment with the active ingredients or combinations of active ingredients was carried out after, before and / or after emergence of the plants, as a rule in the 2 to 4 leaf stage in various dosages with a water application rate of the equivalent of 100 to 400 l / ha.

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Abstract

La présente invention concerne des combinaisons herbicides comprenant une quantité active de composantes (A), (B) et (C) et ayant des propriétés améliorées en tant qu'agents de protection végétale. Selon l'invention, (A) est un ou plusieurs herbicides appartenant au groupe des composés de formule (I) et leurs sels, (B) est un ou plusieurs herbicides appartenant au groupe des composés de formule (II) et leurs sels et esters, et (C) est un ou plusieurs herbicides appartenant au groupe des composés de formule (III) et leurs sels.
EP04741027A 2003-07-28 2004-07-15 Combinaisons herbicides ternaires Withdrawn EP1651046A1 (fr)

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DE10334299A DE10334299A1 (de) 2003-07-28 2003-07-28 Herbizid-Kombinationen
PCT/EP2004/007833 WO2005011384A1 (fr) 2003-07-28 2004-07-15 Combinaisons herbicides ternaires

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US3397054A (en) * 1962-08-30 1968-08-13 Schering Corp Process for controlling plant growth
GR861894B (en) * 1985-07-23 1986-11-24 May & Baker Ltd Herbicidal method comprising the use of diflufenican
US4943544A (en) * 1989-10-10 1990-07-24 Corhart Refractories Corporation High strength, abrasion resistant refractory castable
US5534486A (en) * 1991-04-04 1996-07-09 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen
US5549859A (en) * 1992-08-11 1996-08-27 E. Khashoggi Industries Methods for the extrusion of novel, highly plastic and moldable hydraulically settable compositions
US5527387A (en) * 1992-08-11 1996-06-18 E. Khashoggi Industries Computer implemented processes for microstructurally engineering cementious mixtures
WO2003028467A1 (fr) * 2001-09-27 2003-04-10 Syngenta Participations Ag Composition herbicide
US7137448B2 (en) * 2003-12-22 2006-11-21 Bj Services Company Method of cementing a well using composition containing zeolite

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