WO2000069266A1 - Herbicidal agent based on metamitron and glyphosate or their derivatives and salts - Google Patents

Herbicidal agent based on metamitron and glyphosate or their derivatives and salts Download PDF

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Publication number
WO2000069266A1
WO2000069266A1 PCT/EP2000/003929 EP0003929W WO0069266A1 WO 2000069266 A1 WO2000069266 A1 WO 2000069266A1 EP 0003929 W EP0003929 W EP 0003929W WO 0069266 A1 WO0069266 A1 WO 0069266A1
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Prior art keywords
glyphosate
salts
metamitron
derivatives
propylammonium
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PCT/EP2000/003929
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German (de)
French (fr)
Inventor
Dieter Feucht
Mark Wilhelm Drewes
Peter Dahmen
Rolf Pontzen
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Bayer Aktiengesellschaft
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Priority to AU49154/00A priority Critical patent/AU4915400A/en
Publication of WO2000069266A1 publication Critical patent/WO2000069266A1/en

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    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines

Definitions

  • the invention relates to new herbicidal, synergistic active ingredient combinations which are derived from the known active ingredient metamitron (4-amino-4,5-dihydro-3-methyl-6-phenyl-l, 2,4-triazin-5-one or 4-amino- 3-methyl-6-phenyl-l, 2,4-triazin-5 (4H) -one) on the one hand and the known active ingredient glyphosate (N-phosphonomethyl-glycine) and / or the derivatives and salts of glyphosate on the other hand and with particular good success can be used for weed control.
  • metamitron 4-amino-4,5-dihydro-3-methyl-6-phenyl-l, 2,4-triazin-5-one or 4-amino- 3-methyl-6-phenyl-l, 2,4-triazin-5 (4H) -one
  • glyphosate N-phosphonomethyl-glycine
  • derivatives and salts of glyphosate on the other hand and with particular good
  • the active ingredient metamitron has long been known (cf. DE-A-2 138 031 / US-A-3 910 909; Pestic. Se. 6 (1975), 239-244) and has proven itself in selective weed control, in particular in beet crops . However, it would be desirable to reduce the amount of weed control.
  • the active ingredient glyphosate and its derivatives and salts have also long been known as agents for controlling weeds (cf. DE-A-2 152 826 / DE-A-2 167 051 / US-A-3 799 758 / US-A- 3 977 860 / US-A-4 405 531 / EP-A-54 382).
  • this active ingredient and its derivatives and salts only work when applied after the weeds emerge; there is practically no effect against weeds emerging after use.
  • Salts shows pronounced synergistic effects with regard to the action against weeds and can be used particularly advantageously in broadly effective combination preparations for combating weeds.
  • the invention relates to synergistic herbicidal compositions comprising a combination of (a) Metamitron (4-amino-4,5-dihydro-3-methyl-6-phenyl-l, 2,4-triazin-5-one or 4-amino-3-methyl-6-phenyl-l, 2nd , 4-triazin-5 (4H) -one) of the formula (I)
  • R represents hydrogen or alkyl
  • R represents hydrogen or alkyl
  • Q + stands for the cation of a base, 1 to 1 part by weight of the metamitron accounts for 0.01 to 100 parts by weight of the glyphosate and / or its derivatives and salts.
  • agents are preferred which are characterized in that
  • R represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, and
  • agents which are characterized in that
  • R represents hydrogen, methyl, ethyl, n- or i-propyl
  • the active ingredients glyphosate (N-phosphonomethyl-glycine) and / or its sodium salt and / or its dimethylammonium salt and / or its i-propylammonium salt and / or its trimethylsulfonium salt (sulfosate) are particularly preferred as component (b) for the agents according to the invention . It has now surprisingly been found that the active substance combinations defined above of metamitron and glyphosate (N-phosphonomethyl-glycine) and / or their derivatives or salts of the general formula (II) or (III) have a particularly good herbicidal activity and with Success can be used for efficient weed control.
  • the herbicidal activity of the active compound combinations according to the invention consisting of the active ingredient metamitron and the active ingredient glyphosate and / or its derivatives or salts is considerably higher than the sum of the effects of the individual active ingredients.
  • the new active ingredient combinations can also combat weeds that are otherwise difficult to control (e.g. due to signs of resistance).
  • the new active ingredient combinations are therefore a valuable asset on the
  • the active substance combinations according to the invention can e.g. can be used in the following plants:
  • the active compound combinations according to the invention can also be used in these crop plants to control weeds.
  • Examples of cultivated plants are:
  • Rice, corn, wheat, barley, oats, sugar cane, cotton, soybeans, rapeseed and beets - in particular beets (fodder beets and sugar beets) - may be mentioned as crop plants which are to a certain extent resistant to the active ingredient metamitron.
  • Maize, soybean, cotton, sugar cane, rape and beet are examples of crop plants which are potentially resistant to the active ingredient glyphosate and its derivatives or salts - generally produced by known biotechnological methods.
  • the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges.
  • 0.01 to 100 parts by weight, preferably 0.05 to 50 parts by weight and particularly preferably 0.2 to 20 parts by weight of active compound of the general formula (II) and / or (III) are present in 1 part by weight of active ingredient metamitron.
  • the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as
  • ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic Table stone flours, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g.
  • suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt,
  • Molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active ingredients, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active ingredients contained in the active ingredient combinations can also be mixed in individual formulations during use, ie applied in the form of tank mixes.
  • the new combinations of active ingredients, as such or in their formulations can furthermore also be used in a mixture with other known herbicides, finished formulations or tank mixtures again being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible.
  • "safeners" can also be added.
  • mineral or vegetable oils which are compatible with plants (eg the commercial preparation "Oleo DuPont 11E") or ammonium salts such as eg
  • ammonium sulfate or ammonium rhodanide include ammonium sulfate or ammonium rhodanide.
  • the new active substance combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
  • the active compound combinations according to the invention can be applied especially after the plants have emerged, that is to say in the post-emergence process.
  • the application rates of the active compound combinations according to the invention can be varied within a certain range; they hang among other things depending on the weather and soil factors.
  • the application rates are between 10 g and 10 kg per ha, preferably between 50 g and 5 kg per ha, particularly preferably between 100 g and 2 kg per ha.
  • Herbicides always have a synergistic effect if the herbicidal activity of the active ingredient combination is greater than that of the individual active ingredients applied.
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.
  • Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 500 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention relates to a synergistic herbicidal agent containing a combination consisting of (a) metamitron of formula (I) and (b) glyphosate and/or their derivatives of general formula (II): (HO)2P(O)-CH2-NH-CH2-CO-O-R, wherein R represents hydrogen or alkyl and/or the salts of general formula (III), wherein R represents hydrogen or alkyl and Q<+> represents a base cation.

Description

Herbizide Mittel auf Basis von Metamitron und Glyphosat oder dessen Deriva- ten und SalzenHerbicidal agents based on metamitron and glyphosate or their derivatives and salts
Die Erfindung betrifft neue herbizide, synergistische Wirkstoffkombinationen, die aus dem bekannten Wirkstoff Metamitron (4-Amino-4,5-dihydro-3-methyl-6-phenyl- l,2,4-triazin-5-on oder 4-Amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-on) einerseits und dem bekannten Wirkstoff Glyphosat (N-Phosphonomethyl-glycin) und/oder den Derivaten und Salzen von Glyphosat andererseits bestehen und mit besonders gutem Erfolg zur Unkrautbekämpfung verwendet werden können.The invention relates to new herbicidal, synergistic active ingredient combinations which are derived from the known active ingredient metamitron (4-amino-4,5-dihydro-3-methyl-6-phenyl-l, 2,4-triazin-5-one or 4-amino- 3-methyl-6-phenyl-l, 2,4-triazin-5 (4H) -one) on the one hand and the known active ingredient glyphosate (N-phosphonomethyl-glycine) and / or the derivatives and salts of glyphosate on the other hand and with particular good success can be used for weed control.
Der Wirkstoff Metamitron ist seit langem bekannt (vgl. DE-A-2 138 031 / US-A- 3 910 909; Pestic. Sei. 6 (1975), 239-244) und in der selektiven Unkrautbekämpfung, insbesondere in Rübenkulturen, bewährt. Es wäre jedoch eine Senkung der Aufwand- menge bei der Unkrautbekämpfung wünschenswert.The active ingredient metamitron has long been known (cf. DE-A-2 138 031 / US-A-3 910 909; Pestic. Se. 6 (1975), 239-244) and has proven itself in selective weed control, in particular in beet crops . However, it would be desirable to reduce the amount of weed control.
Der Wirkstoff Glyphosat und dessen Derivate und Salze sind ebenfalls seit langem als Mittel zur Bekämpfung von Unkräutern bekannt (vgl. DE-A-2 152 826 / DE-A- 2 167 051 / US-A-3 799 758 / US-A-3 977 860 / US-A-4 405 531 / EP-A-54 382). Dieser Wirkstoff und seine Derivate und Salze wirken jedoch nur bei Anwendung nach dem Auflaufen der Unkräuter; eine Wirkung gegen nach der Anwendung neu auflaufende Unkräuter ist praktisch nicht gegeben.The active ingredient glyphosate and its derivatives and salts have also long been known as agents for controlling weeds (cf. DE-A-2 152 826 / DE-A-2 167 051 / US-A-3 799 758 / US-A- 3 977 860 / US-A-4 405 531 / EP-A-54 382). However, this active ingredient and its derivatives and salts only work when applied after the weeds emerge; there is practically no effect against weeds emerging after use.
Überraschend wurde nun gefunden, daß der Wirkstoff Metamitron bei gemeinsamer Anwendung mit dem bekannten Wirkstoff Glyphosat und/oder dessen Derivaten undSurprisingly, it has now been found that the active ingredient metamitron when used together with the known active ingredient glyphosate and / or its derivatives and
Salzen ausgesprochen synergistische Effekte hinsichtlich der Wirkung gegen Unkräuter zeigt und besonders vorteilhaft in breit wirksamen Kombinationspräparaten zur Bekämpfung von Unkräutern verwendet werden kann.Salts shows pronounced synergistic effects with regard to the action against weeds and can be used particularly advantageously in broadly effective combination preparations for combating weeds.
Gegenstand der Erfindung sind synergistische herbizide Mittel enthaltend eine Kombination bestehend aus (a) Metamitron (4-Amino-4,5-dihydro-3-methyl-6-phenyl-l,2,4-triazin-5-on oder 4-Amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-on) der Formel (I)The invention relates to synergistic herbicidal compositions comprising a combination of (a) Metamitron (4-amino-4,5-dihydro-3-methyl-6-phenyl-l, 2,4-triazin-5-one or 4-amino-3-methyl-6-phenyl-l, 2nd , 4-triazin-5 (4H) -one) of the formula (I)
Figure imgf000004_0001
und
Figure imgf000004_0001
and
(b) Glyphosat (N-Phosphonomethyl-glycin) und/oder dessen Derivaten der allgemeinen Formel (II),(b) glyphosate (N-phosphonomethyl-glycine) and / or its derivatives of the general formula (II),
(HO)2P(O)-CH2-NH-CH2-CO-O-R (II)(HO) 2 P (O) -CH 2 -NH-CH 2 -CO-OR (II)
in welcherin which
R für Wasserstoff oder Alkyl steht,R represents hydrogen or alkyl,
und/oder den Salzen der allgemeinen Formel (III),and / or the salts of the general formula (III),
O H0^ /P— CH 2— NH-CH 2-COOR (m)O H0 ^ / P— CH 2— NH-CH 2-COOR ( m )
Q o" in welcher Q o " in which
R für Wasserstoff oder Alkyl steht, undR represents hydrogen or alkyl, and
Q+ für das Kation einer Base steht, wobei auf 1 Gewichtsteil des Metamitrons 0,01 bis 100 Gewichtsteile des Glyphosats und/oder dessen Derivate und Salze entfallen.Q + stands for the cation of a base, 1 to 1 part by weight of the metamitron accounts for 0.01 to 100 parts by weight of the glyphosate and / or its derivatives and salts.
Erfindungsgemäß bevorzugt sind Mittel, die dadurch gekennzeichnet sind, daßAccording to the invention, agents are preferred which are characterized in that
R für Wasserstoff, Methyl, Ethyl, n- oder i-Propyl, n-, i- oder s-Butyl steht, undR represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, and
Q+ für ein Natrium-, Kalium-, Ammonium-, Methylammonium-, Ethyl- ammonium-, n- oder i-Propylammonium-, n-, i-, s- oder t-Butylammonium-, Dimethylammonium-, Diethylammonium-, Di-n-propyl-ammonium-, Di-i- propylammonium-, Di-n-butylammonium-, Di-i-butylammonium-, Di-s- butylammonium-, Trimethylammonium-, Triethyl-ammonium-, Tripropyl- ammonium-, Tributylammonium-, Trimethylsulfonium-, Triethylsulfonium- Ion steht.Q + for a sodium, potassium, ammonium, methylammonium, ethylammonium, n- or i-propylammonium, n-, i-, s- or t-butylammonium, dimethylammonium, diethylammonium, di -n-propyl-ammonium, di-i-propylammonium, di-n-butylammonium, di-i-butylammonium, di-s-butylammonium, trimethylammonium, triethylammonium, tripropylammonium, tributylammonium -, Trimethylsulfonium-, triethylsulfonium ion is.
Erfindungsgemäß besonders bevorzugt sind Mittel, die dadurch gekennzeichnet sind, daßAccording to the invention, particular preference is given to agents which are characterized in that
R für Wasserstoff, Methyl, Ethyl, n- oder i-Propyl steht,R represents hydrogen, methyl, ethyl, n- or i-propyl,
Q+ für ein Natrium-, Kalium-, Ammonium-, Methylammonium-, Ethyl- ammonium-, n- oder i-Propylammonium-, Dimethylammonium-, Diethylammonium-, Di-n-propyl-ammonium-, Di-i-propylammonium-, Trimethyl- sulfonium-Ion steht.Q + for sodium, potassium, ammonium, methylammonium, ethylammonium, n- or i-propylammonium, dimethylammonium, diethylammonium, di-n-propylammonium, di-i-propylammonium , Trimethyl sulfonium ion.
Die Wirkstoffe Glyphosat (N-Phosphonomethyl-glycin) und/oder dessen Natriumsalz und/oder dessen Dimethylammoniumsalz und/oder dessen i-Propylammoniumsalz und/oder dessen Trimethylsulfoniumsalz (Sulfosate) seien als Komponente (b) für die erfindungsgemäßen Mittel als ganz besonders bevorzugt hervorgehoben. Es wurde nun überraschend gefunden, daß die oben definierten Wirkstoffkombinationen aus Metamitron und Glyphosat (N-Phosphonomethyl-glycin) und/oder dessen Derivaten bzw. Salzen der allgemeinen Formel (II) bzw. (III) eine besonders lιob< herbizide Wirksamkeit aufweisen und mit Erfolg zur effizienten Unkrautbekämpfung verwendet werden können.The active ingredients glyphosate (N-phosphonomethyl-glycine) and / or its sodium salt and / or its dimethylammonium salt and / or its i-propylammonium salt and / or its trimethylsulfonium salt (sulfosate) are particularly preferred as component (b) for the agents according to the invention . It has now surprisingly been found that the active substance combinations defined above of metamitron and glyphosate (N-phosphonomethyl-glycine) and / or their derivatives or salts of the general formula (II) or (III) have a particularly good herbicidal activity and with Success can be used for efficient weed control.
Überraschenderweise ist die herbizide Wirksamkeit der erfindungsgemäßen Wirk- stoffkombinationen aus dem Wirkstoff Metamitron und dem Wirkstoff Glyphosat und/oder seinen Derivaten bzw. Salzen erheblich höher als die Summe der Wirkun- gen der einzelnen Wirkstoffe.Surprisingly, the herbicidal activity of the active compound combinations according to the invention consisting of the active ingredient metamitron and the active ingredient glyphosate and / or its derivatives or salts is considerably higher than the sum of the effects of the individual active ingredients.
Es liegt somit ein nicht vorhersehbarer synergistischer Effekt vor und nicht nur eine Wirkungsergänzung. Die neuen Wirkstoffkombinationen können auch sonst schwer bekämpfbare Unkräuter (z.B. wegen Resistenzerscheinungen) gut bekämpfen. Die neuen Wirkstoffkombinationen stellen somit eine wertvolle Bereicherung auf demThere is therefore an unforeseeable synergistic effect and not just an addition. The new active ingredient combinations can also combat weeds that are otherwise difficult to control (e.g. due to signs of resistance). The new active ingredient combinations are therefore a valuable asset on the
Gebiet der Unkrautbekämpfung dar.Area of weed control.
Die erfindungsgemäßen Wirkstoffkombinationen können z.B. bei den folgenden Pflanzen verwendet werden:The active substance combinations according to the invention can e.g. can be used in the following plants:
Dikotyle Unkräuter der Gattungen: Cassia, Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,Dicotyledon weeds of the genera: Cassia, Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsiumchum, Cardu , Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,
Ranunculus, Sphenoclea, Taraxacum.Ranunculus, Sphenoclea, Taraxacum.
Monokotyle Unkräuter der Gattungen: Echinochloa, Eriochloa, Setaria, Panicum,Monocotyledonous weeds of the genera: Echinochloa, Eriochloa, Setaria, Panicum,
Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris.Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris.
Soweit Kulturpflanzen gegenüber den Verbindungen der Formel (I) und/oder (11) resistent sind, können die erfindungsgemäßen Wirkstoffkombinationen auch in diesen Kulturpflanzen zur Unkrautbekämpfung eingesetzt werden. Als Beispiele für Kulturpflanzen seien genannt:If crop plants are resistant to the compounds of the formula (I) and / or (11), the active compound combinations according to the invention can also be used in these crop plants to control weeds. Examples of cultivated plants are:
Monokotyle Kulturen der Gattungen: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.
Dikotyle Kulturen der Gattungen: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Als gegenüber dem Wirkstoff Metamitron in gewissem Umfang resistente Kulturpflanzen seien beispielsweise Reis, Mais, Weizen, Gerste, Hafer, Zuckerrohr, Baumwolle, Soja, Raps und Rüben - insbesondere Rüben (Futterrüben und Zuckerrüben) - genannt.Rice, corn, wheat, barley, oats, sugar cane, cotton, soybeans, rapeseed and beets - in particular beets (fodder beets and sugar beets) - may be mentioned as crop plants which are to a certain extent resistant to the active ingredient metamitron.
Als potentiell gegenüber dem Wirkstoff Glyphosat und seiner Derivate oder Salze resistente Kulturpflanzen - im allgemeinen durch bekannte biotechnologische Methoden erzeugt - seien beispielsweise Mais, Soja, Baumwolle, Zuckerrohr, Raps und Rüben genannt.Maize, soybean, cotton, sugar cane, rape and beet are examples of crop plants which are potentially resistant to the active ingredient glyphosate and its derivatives or salts - generally produced by known biotechnological methods.
Die Verwendung der erfindungsgemäßen Wirkstoffkombinationen ist jedoch keineswegs auf diese Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen.However, the use of the active compound combinations according to the invention is by no means restricted to these genera, but extends in the same way to other plants.
Der synergistische Effekt der erfindungsgemäßen Wirkstoffkombinationen ist bei bestimmten Konzentrationsverhältnissen besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil Wirkstoff Metamitron 0,01 bis 100 Gewichtsteile, vorzugsweise 0,05 bis 50 Gewichtsteile und besonders bevorzugt 0,2 bis 20 Gewichtsteile Wirkstoff der allgemeinen Formel (II) und/oder (III).The synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios. However, can the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 0.01 to 100 parts by weight, preferably 0.05 to 50 parts by weight and particularly preferably 0.2 to 20 parts by weight of active compound of the general formula (II) and / or (III) are present in 1 part by weight of active ingredient metamitron.
Die Wirkstoffkombinationen können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.The active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln.These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkyl- naphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wieIf water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as
Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
Als feste Trägerstoffe kommen in Frage: z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthe- tische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B. Alkylarylpolyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.The following are suitable as solid carriers: for example ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic Table stone flours, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural stones such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as Sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospho- lipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt,Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt,
Molybdän und Zink verwendet werden.Molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent an Wirkstoffen, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95 percent by weight of active ingredients, preferably between 0.5 and 90%.
Die erfindungsgemäßen Wirkstoffkombinationen werden im allgemeinen in Form von Fertigformulierungen zur Anwendung gebracht. Die in den Wirkstoffkombinationen enthaltenen Wirkstoffe können aber auch in Einzelformulierungen bei der Anwendung gemischt, d.h. in Form von Tankmischungen zur Anwendung gebracht werden. Die neuen Wirkstoffkombinationen können als solche oder in ihren Formulierungen weiterhin auch in Mischung mit anderen bekannten Herbiziden Verwendung finden, wobei wiederum Fertigformulierungen oder Tankmischungen möglich sind. Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Fungiziden, Insektiziden, Akariziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Wuchsstoffen, Pflanzennährstoffen und Bodenstrukturverbesserungsmitteln ist möglich. Gegebenfalls können auch „Safener" zugesetzt werden. Für bestimmte Anwendungszwecke, insbesondere im Nachauflauf- Verfahren, kann es ferner vorteilhaft sein, in die Formulierungen als weitere Zusatzstoffe pflanzenverträgliche mineralische oder vegetabilische Öle (z.B. das Handelspräparat "Oleo DuPont 11E") oder Ammoniumsalze wie z.B.The active compound combinations according to the invention are generally used in the form of finished formulations. However, the active ingredients contained in the active ingredient combinations can also be mixed in individual formulations during use, ie applied in the form of tank mixes. The new combinations of active ingredients, as such or in their formulations, can furthermore also be used in a mixture with other known herbicides, finished formulations or tank mixtures again being possible. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible. If necessary, "safeners" can also be added. For certain applications, in particular in the post-emergence process, it may also be advantageous to add mineral or vegetable oils which are compatible with plants (eg the commercial preparation "Oleo DuPont 11E") or ammonium salts such as eg
Ammoniumsulfat oder Ammoniumrhodanid aufzunehmen.Include ammonium sulfate or ammonium rhodanide.
Die neuen Wirkstoffkombinationen können als solche, in Form ihrer Formulierungen oder der daraus durch weiteres Verdünnen bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Spritzen, Sprühen, Stäuben oder Streuen.The new active substance combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
Die erfindungsgemäßen Wirkstoffkombinationen können vor allem nach dem Auf- laufen der Pflanzen appliziert werden, also im Nachauflauf- Verfahren.The active compound combinations according to the invention can be applied especially after the plants have emerged, that is to say in the post-emergence process.
Die Aufwandmengen der erfindungsgemäßen Wirkstoffkombinationen können in einem gewissen Bereich variiert werden; sie hängen u.a. vom Wetter und von den Bodenfaktoren ab. Im allgemeinen liegen die Aufwandmengen zwischen 10 g und 10 kg pro ha, vorzugsweise zwischen 50 g und 5 kg pro ha, besonders bevorzugt zwischen 100 g und 2 kg pro ha.The application rates of the active compound combinations according to the invention can be varied within a certain range; they hang among other things depending on the weather and soil factors. In general, the application rates are between 10 g and 10 kg per ha, preferably between 50 g and 5 kg per ha, particularly preferably between 100 g and 2 kg per ha.
Die gute herbizide Wirkung der neuen Wirkstoffkombinationen geht aus den nachfolgenden Beispielen hervor. Während die einzelnen Wirkstoffe in der herbiziden Wirkung Schwächen aufweisen, zeigen die Kombinationen durchweg eine sehr guteThe good herbicidal activity of the new active compound combinations can be seen from the examples below. While the individual active ingredients have weaknesses in the herbicidal action, the combinations consistently show a very good one
Unkrautwirkung, die über eine einfache Wirkungssummierung hinausgeht. Ein synergistischer Effekt liegt bei Herbiziden immer dann vor, wenn die herbizide Wirkung der Wirkstoffkombination größer ist als die der einzelnen applizierten Wirkstoffe.Weed action that goes beyond a simple addition of effects. Herbicides always have a synergistic effect if the herbicidal activity of the active ingredient combination is greater than that of the individual active ingredients applied.
Die zu erwartende Wirkung für eine gegebene Kombination zweier Herbizide kann wie folgt berechnet werden (vgl. COLBY, S.R.: "Calculating synergistic and anta- gonistic responses of herbicide combinations", Weeds 15, Seiten 20 - 22, 1967):The expected effect for a given combination of two herbicides can be calculated as follows (cf. COLBY, S.R .: "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
Wenn X = % Schädigung durch Herbizid A (Wirkstoff der Formel I) bei p kg/ha Aufwandmenge und Y = % Schädigung durch Herbizid B (Wirkstoff der Formel II) bei q kg/ha Aufwandmenge und E = die erwartete Schädigung der Herbizide A und B bei p und q kg/ha Aufwandmenge, dann ist E = X + Y - (X * Y/100).If X =% damage by herbicide A (active ingredient of formula I) at p kg / ha application rate and Y =% damage by herbicide B (active ingredient of formula II) at q kg / ha application rate and E = the expected damage to herbicides A and B at p and q kg / ha application rate, then E = X + Y - (X * Y / 100).
Ist die tatsächliche Schädigung größer als berechnet, so ist die Kombination in ihrer Wirkung überadditiv, das heißt, sie zeigt einen synergistischen Effekt.If the actual damage is greater than calculated, the effect of the combination is super-additive, that is, it shows a synergistic effect.
Aus den folgenden Beispielen geht hervor, daß die gefundene herbizide Wirkung der erfϊndungsgemäßen Wirkstoffkombinationen bei den Unkräutern größer ist als die berechnete, das heißt, daß die neuen Wirkstoffkombinationen synergistisch wirken. The following examples show that the herbicidal activity of the active compound combinations according to the invention in the weeds is greater than the calculated one, that is to say that the new active compound combinations act synergistically.
Anwendungsbeispiele:Examples of use:
Es wurden handelsübliche Formulierungen der involvierten Wirkstoffe benutzt. Dit für die Versuche benötigten Wirkstoffkonzentrationen wurden durch Verdünnen mit Wasser hergestellt.Commercial formulations of the active ingredients involved were used. The drug concentrations required for the tests were prepared by dilution with water.
Beispiel AExample A
Post-emergence-TestPost emergence test
Mit der Wirkstoffzubereitung spritzt man Testpflanzen, welche eine Höhe von 5 bis 15 cm haben so, daß die jeweils gewünschten Wirkstoffmengen pro Flächeneinheit ausgebracht werden. Die Konzentration der Spritzbrühe wird so gewählt, daß in 500 1 Wasser/ha die jeweils gewünschten Wirkstoffmengen ausgebracht werden.Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area. The concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 500 l of water / ha.
Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle.After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
Es bedeuten:It means:
0 % = keine Wirkung (wie unbehandelte Kontrolle) 100 % = totale Vernichtung0% = no effect (like untreated control) 100% = total destruction
Wirkstoffe, Aufwandmengen, Testpflanzen und Resultate gehen aus den nach- folgenden Tabellen hervor, wobei die in den Tabellen verwendeten Abkürzungen folgende Bedeutung haben:Active substances, application rates, test plants and results are shown in the following tables, the abbreviations used in the tables have the following meanings:
(I) Metamitron (4-Amino-4,5-dihydro-3-methyl-6-phenyl- 1 ,2,4-triazin-5-on oder 4-Amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-on) (appliziert als „Goltix 70 WG") (IM) Glyphosat-i-propylammonium (N-Phosphonomethyl-glycin-i-propyl- ammonium)(I) Metamitron (4-amino-4,5-dihydro-3-methyl-6-phenyl-1, 2,4-triazin-5-one or 4-amino-3-methyl-6-phenyl-1,2 , 4-triazin-5 (4H) -one) (applied as "Goltix 70 WG") (IM) glyphosate-i-propylammonium (N-phosphonomethyl-glycine-i-propylammonium)
(appliziert als „Roundup 360 SC")(applied as "Roundup 360 SC")
( ) In Klammern stehen gegebenenfalls die nach der oben angegebenen Formel nach Colby berechneten Werte.() The values calculated using the Colby formula given above may be in brackets.
Tabelle AI post emergence Test/ GewächshausTable AI post emergence test / greenhouse
Figure imgf000013_0001
Figure imgf000013_0001
Tabelle A2 post emergence Test/ GewächshausTable A2 post emergence test / greenhouse
Figure imgf000013_0002
Tabelle A3 post emergence Test/ Gewächshaus
Figure imgf000013_0002
Table A3 post emergence test / greenhouse
Figure imgf000014_0001
Figure imgf000014_0001
Tabelle A4 post emergence Test/ GewächshausTable A4 post emergence test / greenhouse
Figure imgf000014_0002
Figure imgf000014_0002
Tabelle A5 post emergence Test/ GewächshausTable A5 post emergence test / greenhouse
Figure imgf000014_0003
Tabelle A6 post emergence Test/ Gewächshaus
Figure imgf000014_0003
Table A6 post emergence test / greenhouse
Figure imgf000015_0001
Figure imgf000015_0001

Claims

Patentansprüche claims
1. Mittel enthaltend eine Kombination bestehend aus1. Composition containing a combination of
(a) Metamitron (4-Amino-4,5-dihydro-3-methyl-6-phenyl-l,2,4-triazin-5- on oder 4-Amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-on) der Formel (I)(a) Metamitron (4-amino-4,5-dihydro-3-methyl-6-phenyl-l, 2,4-triazin-5-one or 4-amino-3-methyl-6-phenyl-l, 2nd , 4-triazin-5 (4H) -one) of the formula (I)
Figure imgf000016_0001
und
Figure imgf000016_0001
and
(b) Glyphosat (N-Phosphonomethyl-glycin) und/oder dessen Derivaten der allgemeinen Formel (II),(b) glyphosate (N-phosphonomethyl-glycine) and / or its derivatives of the general formula (II),
(HO)2P(O)-CH2-NH-CH2-CO-O-R (II)(HO) 2 P (O) -CH 2 -NH-CH 2 -CO-OR (II)
in welcherin which
R für Wasserstoff oder Alkyl steht,R represents hydrogen or alkyl,
und/oder den Salzen der allgemeinen Formel (III),and / or the salts of the general formula (III),
Figure imgf000016_0002
Figure imgf000016_0002
QQ
in welcherin which
R für Wasserstoff oder Alkyl steht, und Q+ für das Kation einer Base steht,R represents hydrogen or alkyl, and Q + stands for the cation of a base,
wobei auf 1 Gewichtsteil des Metamitrons 0,01 bis 100 Gewichtsteile des Glyphosats und/oder dessen Derivate und Salze entfallen.1 to 1 part by weight of the metamitron accounts for 0.01 to 100 parts by weight of the glyphosate and / or its derivatives and salts.
2. Mittel gemäß Anspruch, dadurch gekennzeichnet, daß2. Means according to claim, characterized in that
R für Wasserstoff, Methyl, Ethyl, n- oder i-Propyl, n-, i- oder s-Butyl steht, undR represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, and
Q+ für ein Natrium-, Kalium-, Ammonium-, Methylammonium-, Ethyl- ammonium-, n- oder i-Propylammonium-, n-, i-, s- oder t-Butyl- ammonium-, Dimethylammonium-, Diethylammonium-, Di-n-propyl- ammonium-, Di-i-propylammonium-, Di-n-butylammonium-, Di-i- butylam onium-, Di-s-butylammonium-, Trimethylammonium-, Tri- ethyl-ammonium-, Tripropylammonium-, Tributylammonium-, Tri- methylsulfonium-, Triethylsulfonium-Ion steht.Q + for a sodium, potassium, ammonium, methylammonium, ethylammonium, n- or i-propylammonium, n-, i-, s- or t-butylammonium, dimethylammonium, diethylammonium , Di-n-propylammonium, di-i-propylammonium, di-n-butylammonium, di-i-butylammonium, di-s-butylammonium, trimethylammonium, triethylammonium, tripropylammonium -, Tributylammonium-, trimethylsulfonium, triethylsulfonium ion is.
3. Mittel gemäß Anspruch, dadurch gekennzeichnet, daß3. Means according to claim, characterized in that
R für Wasserstoff, Methyl, Ethyl, n- oder i-Propyl steht,R represents hydrogen, methyl, ethyl, n- or i-propyl,
Q+ für ein Natrium-, Kalium-, Ammonium-, Methylammonium-, Ethyl- ammonium-, n- oder i-Propylammonium-, Dimethylammonium-, Diethylammonium-, Di-n-propyl-ammonium-, Di-i-propylammonium-, Trime hylsulfonium-Ion steht.Q + for sodium, potassium, ammonium, methylammonium, ethylammonium, n- or i-propylammonium, dimethylammonium, diethylammonium, di-n-propylammonium, di-i-propylammonium , Trime hylsulfonium-ion stands.
4. Mittel gemäß einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß auf 1 Gewichtsteil des Metamitrons 0,05 bis 50 Gewichtsteile des Glyphosats und/oder seiner Derivate und Salze entfallen. 4. Composition according to one of claims 1 to 3, characterized in that 0.05 to 50 parts by weight of the glyphosate and / or its derivatives and salts are accounted for 1 part by weight of the metamitron.
5. Mittel gemäß einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß auf 1 Gewichtsteil des Metamitrons 0,2 bis 20 Gewichtsteile des Glyphosats und/oder seiner Derivate und Salze entfallen.5. Agent according to one of claims 1 to 3, characterized in that 0.2 to 20 parts by weight of the glyphosate and / or its derivatives and salts account for 1 part by weight of the metamitron.
6. Verwendung eines Mittels gemäß einem der Ansprüche 1 bis 5 zur Bekämpfung von unerwünschtem Pflanzenwuchs.6. Use of an agent according to any one of claims 1 to 5 for combating undesirable plant growth.
7. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch ge- kennzeichnet, daß man Mittel gemäß einem der Ansprüche 1 bis 5 auf die unerwünschten Pflanzen und/oder ihren Lebensraum einwirken läßt.7. A method for controlling undesirable plant growth, characterized in that agents according to one of claims 1 to 5 are allowed to act on the undesired plants and / or their habitat.
8. Verfahren zur Herstellung eines herbiziden Mittels, dadurch gekennzeichnet daß man ein Mittel gemäß einem der Ansprüche 1 bis 5 mit oberflächen- aktiven Mitteln und/oder Streckmitteln vermischt. 8. A process for the preparation of a herbicidal composition, characterized in that an agent according to any one of claims 1 to 5 is mixed with surface-active agents and / or extenders.
PCT/EP2000/003929 1999-05-12 2000-05-02 Herbicidal agent based on metamitron and glyphosate or their derivatives and salts WO2000069266A1 (en)

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Publication number Priority date Publication date Assignee Title
EP0441764A1 (en) * 1990-02-05 1991-08-14 Monsanto Europe S.A./N.V. Glyphosate compositions and their use
EP0808569A1 (en) * 1996-05-24 1997-11-26 Monsanto Europe S.A./N.V. New herbicidal compositions and use thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0441764A1 (en) * 1990-02-05 1991-08-14 Monsanto Europe S.A./N.V. Glyphosate compositions and their use
EP0808569A1 (en) * 1996-05-24 1997-11-26 Monsanto Europe S.A./N.V. New herbicidal compositions and use thereof

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