WO1997031535A1 - Herbicidal agents based on n-phosphonomethylglycine esters - Google Patents

Herbicidal agents based on n-phosphonomethylglycine esters Download PDF

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Publication number
WO1997031535A1
WO1997031535A1 PCT/EP1997/000732 EP9700732W WO9731535A1 WO 1997031535 A1 WO1997031535 A1 WO 1997031535A1 EP 9700732 W EP9700732 W EP 9700732W WO 9731535 A1 WO9731535 A1 WO 9731535A1
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Prior art keywords
methyl
group
active ingredient
ethyl
active
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PCT/EP1997/000732
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German (de)
French (fr)
Inventor
Hans-Jochem Riebel
Uwe Priesnitz
Raphael Wieschollek
Markus Dollinger
Ingo Wetcholowsky
Original Assignee
Bayer Aktiengesellschaft
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Priority to AU18737/97A priority Critical patent/AU1873797A/en
Publication of WO1997031535A1 publication Critical patent/WO1997031535A1/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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the invention relates to new herbicidal compositions which consist of pure - not formulated - N-phosphonomethylglycine esters and dissolved or dispersed in water - previously formulated - other known, herbicidally active compounds or combinations of such known, herbicidally active compounds getting produced.
  • N-phosphonomethylglycine alkyl esters have herbicidal properties and - generally in formulated use forms, ie combined with certain additives - can be used to kill unwanted plants (cf. DE 2152826, DE 2166573, US) 3977860). That pure - i.e. active ingredients which are not formulated - are used in spray liquors, but is not common.
  • N-phosphonomethylglycine esters of the general formula (I) N-phosphonomethylglycine esters of the general formula (I)
  • R represents alkyl
  • the invention thus relates to herbicidal compositions, characterized by an effective content of a synergistic active ingredient combination consisting of (a) an N-phosphonomethylglycine ester of the above formula (I), in which R represents alkyl, or an acid adduct of these compounds (“active ingredient of group 1”) and
  • N-phosphonomethylglycine esters of the general formula (I) - and acid adducts of compounds of the formula (I) - in pure, non-formulated form for use in spray liquors of known, formulated herbicidal active compounds can be used and that these spray liquors show extremely synergistic properties in comparison with corresponding application forms of the individual active ingredients.
  • N-phosphonomethylglycine esters of the formula (I) directly in spray liquors without the use of formulation auxiliaries is a significant simplification of the application and thus a valuable enrichment of the prior art.
  • the invention preferably relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
  • R represents straight-chain or branched alkyl having 1 to 10 carbon atoms
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos,
  • Fluoroglycofen (-ethyl), flupoxam, flupropacil, flurenol (n-butyl ester), fluridone, fluroxypyr, flurprimidol, flurtamone, fomesafen, glufosinate (-ammonium), glyphosate, haloxyfop (-ethoxyethyl), hexazinone, imazamethylbenzene , Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil,
  • Tebutam Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thi- diazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), tricyclopyr, tridiphane, trifluralin, triflusulfuron,
  • the invention particularly relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
  • R represents straight-chain or branched alkyl having 2 to 4 carbon atoms
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate-Bensulfuron (Bensulfuron)
  • a particularly preferred group 1 active ingredient is N-phosphonomethylglycine ethyl ester
  • Suitable acids are preferably strong protonic acids, such as hydrogen fluoride, hydrogen chloride (hydrochloric acid), hydrogen bromide, hydrogen iodide, sulfuric acid, phosphoric acid, trifluoroacetic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, and tonic sulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid
  • N-phosphonomethylglycine esters of the general formula (I) are obtained if N-phosphonomethylglycine of the formula (II)
  • an acid such as, for example, hydrogen chloride (hydrogen chloride)
  • an acid binder such as e.g. triethylamine or propylene oxide
  • herbicidal compositions to be used according to the invention can be used both in conventional cultivation methods (row crops with a suitable row width) in plantation crops (for example wine, fruit, citrus) and in industrial and track systems, on paths and squares, but also for stubble treatment and for minimum
  • Tillage processes are used. They are also suitable as burners (killing herbs, e.g. in potatoes) or as defoliants (e.g. in cotton). They are also suitable for use on fallow land. Further areas of application are tree nurseries, forestry, grassland and ornamental plant cultivation
  • Scirpus Papalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera
  • the use of the active compounds and combinations of active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants
  • 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. In general, 1 part by weight of active ingredient in group 1 accounts for 0.001 to 1000 parts by weight, preferably 0.01 to
  • 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 0.05 and 5 kg of active ingredient combination per ha, preferably between 0.06 and 2 kg per ha, particularly preferably between 0.1 and 1.0 kg per ha.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence processes. However, they are preferably used in the post-emergence process.
  • a herbicide always has a synergistic effect if the herbicidal action of the active compound combination is greater than that of the individual applied active compounds.
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.
  • Hydrogen chloride gas is introduced into a suspension of 200 g (1.2 mol) of N-phosphonomethylglycine in 3000 ml of ethanol until saturation. Then the
  • Fluid bed drying, blade drying or circulating air drying in each case combined with conventional comminution processes, such as air jet milling, crushers, rollers, grinding, if appropriate).
  • Hydrogen chloride gas is introduced into a suspension of 5.1 g (30 mmol) of N-phosphonomethyl-glycine in 80 ml of ethanol until saturation.
  • the reaction mixture is heated under reflux for 2 hours and then concentrated in a water jet vacuum.
  • the residue is mixed with acetone stirred and the kristal ⁇ line product isolated by suction

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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 concerns herbicidal agents characterized in that they contain an effective amount of a synergistic combination of substances consisting of a) an N-phosphonomethylglycine ester of the formula (I): (HO)2P(O)-CH2-NH-CH2-NH-CH2-CO-O-R in which R is an alkyl group, or an acid adduct of such compounds ('group 1 substance') and b) at least one compound selected from the group comprising other, prior art herbicides ('group 2 substance'), the agent containing 0.001 to 1000 parts by weight of group 2 substance to every 1 part by weight of group 1 substance.

Description

Herbizide Mittel auf Basis von N-Phosphonomethyl-glvcinesternHerbicidal agents based on N-phosphonomethyl-glvcinestern
Die Erfindung betrifft neue herbizide Mittel, welche aus reinen - nicht formulierten - N-Phosphonomethyl-glycinestern und in Wasser gelösten oder dis¬ pergierten - vorher formulierten - anderen bekannten, herbizid wirksamen Ver¬ bindungen oder Kombinationen von solchen bekannten, herbizid wirksamen Ver¬ bindungen hergestellt werden.The invention relates to new herbicidal compositions which consist of pure - not formulated - N-phosphonomethylglycine esters and dissolved or dispersed in water - previously formulated - other known, herbicidally active compounds or combinations of such known, herbicidally active compounds getting produced.
Es ist bekannt, daß einige N-Phosphonomethyl-glycin-alkylester herbizide Eigen- schaften aufweisen und - im allgemeinen in formulierten Anwendungsformen, d.h mit bestimmten Zuschlagsstoffen kombiniert - zur Abtötung von unerwünschten Pflanzen verwendet werden können (vgl. DE 2152826, DE 2166573, US 3977860). Daß reine - d.h. nicht formulierte Wirkstoffe - in Spritzbrühen zur An¬ wendung kommen, ist jedoch nicht üblich.It is known that some N-phosphonomethylglycine alkyl esters have herbicidal properties and - generally in formulated use forms, ie combined with certain additives - can be used to kill unwanted plants (cf. DE 2152826, DE 2166573, US) 3977860). That pure - i.e. active ingredients which are not formulated - are used in spray liquors, but is not common.
Es wurde nun gefunden, daß N-Phosphonomethyl-glycinester der allgemeinen For¬ mel (I),It has now been found that N-phosphonomethylglycine esters of the general formula (I)
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)(HO) 2 P (O) -CH 2 -NH-CH 2 -CO-OR (I)
in welcherin which
R für Alkyl steht,R represents alkyl,
- sowie Säureaddukte von Verbindungen der Formel (I) -- and acid adducts of compounds of the formula (I) -
als reine Wirkstoffe, d.h. ohne Verwendung weiterer Hilfsstoffe, zu Spritzbruhen von bekannten Herbiziden gegeben werden können und die so hergestellten An¬ wendungsformen mit sehr gutem Erfolg zur Abtötung unerwünschter Pflanzen ver¬ wendet werden können, wobei synergistische Effekte zu beobachten sindas pure active substances, i.e. can be added to spray liquors from known herbicides without the use of further auxiliaries and the application forms thus prepared can be used with very good success to kill undesired plants, synergistic effects being observed
Gegenstand der Erfindung sind somit herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer synergistischen Wirkstoffkombination bestehend aus (a) einem N-Phosphonomethyl-glycinester der obigen Formel (I), in welcher R für Alkyl steht, oder einem Säureaddukt dieser Verbindungen ("Wirkstoff der Gruppe 1 ") undThe invention thus relates to herbicidal compositions, characterized by an effective content of a synergistic active ingredient combination consisting of (a) an N-phosphonomethylglycine ester of the above formula (I), in which R represents alkyl, or an acid adduct of these compounds (“active ingredient of group 1”) and
(b) wenigstens einer Verbindung aus der Gruppe der übrigen bekannten Herbizide ("Wirkstoff der Gruppe 2"),(b) at least one compound from the group of the other known herbicides (“active ingredient of group 2”),
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,001 bis 1000 Ge¬ wichtsteile Wirkstoff der Gruppe 2 entfallen.0.001 to 1000 parts by weight of active ingredient of group 2 per 1 part by weight of active ingredient of group 1.
Es ist als ausgesprochen überraschend anzusehen, daß N-Phosphonomethyl-glycin¬ ester der allgemeinen Formel (I) - sowie Säureaddukte von Verbindungen der Formel (I) - in reiner, nicht formulierter Form zur Anwendung in Spritzbrühen be¬ kannter, formulierter Herbizid-Wirkstoffe eingesetzt werden können und daß diese Spritzbrühen im Vergleich mit entsprechenden Anwendungsformen der einzelnen Wirkstoffe ausgesprochen synergistische Eigenschaften zeigen.It is to be regarded as extremely surprising that N-phosphonomethylglycine esters of the general formula (I) - and acid adducts of compounds of the formula (I) - in pure, non-formulated form for use in spray liquors of known, formulated herbicidal active compounds can be used and that these spray liquors show extremely synergistic properties in comparison with corresponding application forms of the individual active ingredients.
Die Möglichkeit, die N-Phosphonomethyl-glycinester der Formel (I) ohne Ver- wendung von Formulierungshilfsmitteln direkt in Spritzbrühen einzusetzen, stellt eine wesentliche Vereinfachung der Anwendung und somit eine wertvolle Be¬ reicherung des Standes der Technik dar.The possibility of using the N-phosphonomethylglycine esters of the formula (I) directly in spray liquors without the use of formulation auxiliaries is a significant simplification of the application and thus a valuable enrichment of the prior art.
Gegenstand der Erfindung sind vorzugsweise herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination bestehend ausThe invention preferably relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
(a) einem N-Phosphonomethyl-glycinester der allgemeinen Formel (I),(a) an N-phosphonomethylglycine ester of the general formula (I),
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)(HO) 2 P (O) -CH 2 -NH-CH 2 -CO-OR (I)
in welcherin which
R für geradkettiges oder verzweigtes Alkyl mit 1 bis 10 Kohlenstoffatomen steht,R represents straight-chain or branched alkyl having 1 to 10 carbon atoms,
("Wirkstoff der Gruppe 1 ") und (b) einer oder zwei Verbindungen aus einer zweiten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe (jeweils mit "common name" benannt) enthält:("Active substance of group 1") and (b) one or two compounds from a second group of herbicides, which contains the active compounds mentioned below (each named "common name"):
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos,Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos,
Asulam, Atrazin, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butami- fos, Butenachlor, Butylate, Cafenstrole, Carbetamide, Chlom ethoxy fen, Chlor- amben, Chloridazon, Chlorimuron (-ethyl), Chlormethoxynil, Chlornitrofen, Chlor- sulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cy- halofop (-butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimetha¬ metryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop (-ethyl), Flamprop (-isopropyl), Flamprop (-methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone,Asulam, Atrazin, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Butoslor, Butachlor, Butami- chloro Butylates, Cafenstrole, Carbetamide, Chlomethoxy fen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlormethoxynil, Chlornitrofen, Chlorosulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl, Clomropone, Clomropone, Clomazone, Clomazone Clopyrasulfuron, Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimifonican Dimepiperate, Dimethachlor, Dimethametryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etoxapropanidethyl , Flam prop (-isopropyl), flamprop (-methyl), flazasulfuron, fluazifop (-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, fluometuron, fluorochloridone,
Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butylester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Gly- phosate, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imaza- methapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil,Fluoroglycofen (-ethyl), flupoxam, flupropacil, flurenol (n-butyl ester), fluridone, fluroxypyr, flurprimidol, flurtamone, fomesafen, glufosinate (-ammonium), glyphosate, haloxyfop (-ethoxyethyl), hexazinone, imazamethylbenzene , Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil,
Linuron, MCPA, Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenz¬ thiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop- amide, Neburon, Nicosulfuron, Nitrofen, Norflurazon, Orbencarb, Oryzalin, Oxa- diargyl, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Pipero- phos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate,Linuron, MCPA, Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naproanilide, Naproanilide, Napon Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propyzonamide, Proulfuron (Prosulfuron) -ethyl), pyrazoxyfen, pyributicarb, pyridate, pyrithiobac (-sodium), quinchlorac, quinmerac, quizalofop (-ethyl), quizalofop (-p-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone (sulfomethyl), sulfometuron ), Sulfosates,
Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thi- diazimin, Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Tri- allate, Triasulfuron, Tribenuron (-methyl), Tricyclopyr, Tridiphane, Trifluralin, Tri- flusulfuron,Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thi- diazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), tricyclopyr, tridiphane, trifluralin, triflusulfuron,
("Wirkstoffe der Gruppe 2")("Active substances of group 2")
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,01 bis 100 Gewichts¬ teile Wirkstoff der Gruppe 2 entfallen.1 to 1 part by weight of active ingredient in group 1 accounts for 0.01 to 100 parts by weight of active ingredient in group 2.
Gegenstand der Erfindung sind insbesondere herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination bestehend ausThe invention particularly relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
(a) einem N-Phosphonomethyl-glycinester der allgemeinen Formel (I)(a) an N-phosphonomethylglycine ester of the general formula (I)
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)(HO) 2 P (O) -CH 2 -NH-CH 2 -CO-OR (I)
in welcherin which
R für geradkettiges oder verzweigtes Alkyl mit 2 bis 4 Kohlenstoff atomen steht,R represents straight-chain or branched alkyl having 2 to 4 carbon atoms,
("Wirkstoff der Gruppe 1 ") und("Active substance of group 1") and
(b) einer oder zwei Verbindungen aus einer zweiten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe (jeweils mit "common name" be¬ nannt) enthält:(b) one or two compounds from a second group of herbicides, which contains the active compounds mentioned below (in each case called "common name"):
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos, Asulam, Atrazin, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl),Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate-Bensulfuron (Bensulfuron)
Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butami- fos, Butenachlor, Butylate, Cafenstrole, Carbetamide, Chlomethoxyfen, Chlor¬ amben, Chloridazon, Chlorimuron (-ethyl), Chl orm ethoxy nil, Chlornitrofen, Chlor- sulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, ClodinafopBensulide, bentazone, benthiocarb, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bromacil, bromobutide, bromofenoxime, bromoxynil, butachlor, butamifos, butenachlor, butylates, cafenstrole, carbetamides, chloromethoxyfen, chloron amine, chlorine amine chlorur -ethyl), chlorine ethoxy nile, chloronitrofen, chlorosulfuron, chlorotoluron, cinmethylin, cinosulfuron, clethodim, clodinafop
(-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cy- halofop (-butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimetha¬ metryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop (-ethyl), Flamprop(-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyluron, Cyanazines, Cycloate, Cyclosulfamuron, Cycloxydim, Cy- halofop (-butyl), 2,4-D, desmedipham, dicamba, dichloroprop, diclofop (-methyl), difenzoquat, diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn, demethenamid, dinitramine, diphenamide, diquat, dithiopyr, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop (-ethyl), Flamprop
(-isopropyl), Flamprop (-methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butylester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Gly- phosate, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imaza- methapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenz¬ thiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop- amide, Neburon, Nicosulfuron, Nitrofen, Norflurazon, Orbencarb, Oryzalin, Oxa- diargyl, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Pipero- phos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac,(-isopropyl), flamprop (-methyl), flazasulfuron, fluazifop (-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil-buturen ), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Glyphosate, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazauronon, Imazosulfon Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenz¬ thiazuron, Metobenzuron, Metobromuron, Molachloroxoxuron (M) Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Nitrofen, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Piperophos, Pretilachlor-Promulfuryl, Primisulfur metryn, propachlor, propanil, propaquizafop, propyzamide, prosulfocarb, prosulfuron, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyributicarb, pyridate, pyrithiobac (-sodium), quinchlorac,
Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thi- diazimin, Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Tri- allate, Triasulfuron, Tribenuron (-methyl), Tricyclopyr, Tridiphane, Trifluralin, Tri- flusulfuron,Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Tchlorothiazopine, Terbutrynopine diazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), tricyclopyr, tridiphane, trifluralin, triflusulfuron,
("Wirkstoffe der Gruppe 2")("Active substances of group 2")
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,05 bis 50 Gewichtsteile Wirkstoff der Gruppe 2 entfallen.1 part by weight of active ingredient in group 1 each containing 0.05 to 50 parts by weight of active ingredient in group 2.
Als ganz besonders bevorzugter Wirkstoff der Gruppe 1 sei N-Phosphonomethyl- glycin-ethylester genanntA particularly preferred group 1 active ingredient is N-phosphonomethylglycine ethyl ester
Als Säureaddukte sind im Zusammenhang mit der vorliegenden Erfindung all¬ gemein Additionsprodukte aus Verbindungen der Formel (I) und Sauren zu ver- stehen Geeignete Sauren sind hierbei vorzugsweise starke Protonensauren, wie z B Hydrogenfluoπd, Hydrogenchloπd (Salzsaure), Hydrogenbromid, Hydrogen- lodid, Schwefelsaure, Phosphorsaure, Trifluoressigsaure, Methansulfonsäure, Ethansulfonsaure, Propansulfonsaure, Butansulfonsaure, Tπfluormethansulfonsaure, Benzolsulfonsaure und p-ToluolsulfonsaureIn the context of the present invention, addition products of compounds of the formula (I) and acids are generally to be used as acid adducts. Suitable acids are preferably strong protonic acids, such as hydrogen fluoride, hydrogen chloride (hydrochloric acid), hydrogen bromide, hydrogen iodide, sulfuric acid, phosphoric acid, trifluoroacetic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, and tonic sulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, and tonic sulfonic acid,
Die erfindungsgemaß zu verwendenden Verbindungen der Formel (I) sind bereits bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl DE 2152826, DE 2166573, US 3977860)The compounds of formula (I) to be used according to the invention are already known and / or can be prepared by processes known per se (cf. DE 2152826, DE 2166573, US 3977860)
Man erhalt die N-Phosphonomethyl-glycinester der allgemeinen Formel (I), wenn man N-Phosphonomethyl-glycin der Formel (II)The N-phosphonomethylglycine esters of the general formula (I) are obtained if N-phosphonomethylglycine of the formula (II)
(HO)2P(O)-CH2-NH-CH2-COOH (II)(HO) 2 P (O) -CH 2 -NH-CH 2 -COOH (II)
mit einem Alkohol der Formel (III)with an alcohol of formula (III)
HO-R (III)HO-R (III)
in welcherin which
R die oben angegebene Bedeutung hat,R has the meaning given above,
in Gegenwart einer Saure, wie z B Hydrogenchloπd (Chlorwasserstoff), bei Tem¬ peraturen zwischen 40°C und 150°C umsetzt und das hierbei gebildete Säure¬ addukt der Verbindung der Formel (I) - gegebenenfalls nach Zwischenisolierung - mit einem Saurebindemittel, wie z B Triethylamin oder Propylenoxid, bei Temperaturen zwischen 0°C und 60°C umsetzt (vgl die Herstellungsbeispiele)in the presence of an acid, such as, for example, hydrogen chloride (hydrogen chloride), at temperatures between 40 ° C. and 150 ° C. and the acid adduct formed in this way of the compound of the formula (I) - optionally after intermediate isolation - with an acid binder, such as e.g. triethylamine or propylene oxide, reacted at temperatures between 0 ° C and 60 ° C (see the production examples)
Es wurde nun überraschend gefunden daß die oben definierten Wirkstoffkombina- ttonen aus den N-Phosphonomethyl-glycinestern der Formel (I) und den oben auf¬ geführten Wirkstoffen der Gruppe 2 eine besonders hohe herbizide Wirksamkeit aufweisen Sie können insbesondere mit sehr gutem Erfolg im semi-selektiven und im nicht-selektiven Bereich der Unkrautbekämpfung eingesetzt werden Uberraschenderweise ist die herbizide Wirksamkeit der erfindungsgemäßen Wirk¬ stoffkombinationen aus den Verbindungen der oben aufgeführten Gruppen 1 und 2 erheblich höher als die Summe der Wirkungen der einzelnen WirkstoffeIt has now surprisingly been found that the combination of active ingredients defined above from the N-phosphonomethylglycine esters of the formula (I) and the active ingredients of group 2 listed above have a particularly high herbicidal activity. selective and in the non-selective area of weed control Surprisingly, the herbicidal activity of the active compound combinations according to the invention from the compounds of groups 1 and 2 listed above is considerably higher than the sum of the effects of the individual active compounds
Es liegt somit ein nicht vorhersehbarer synergistischer Effekt vor und nicht nur eine Wirkungserganzung Die neuen Wirkstoffkombinationen und Anwendungsfor¬ men stellen somit eine wertvolle Bereicherung des Standes der Technik darThere is therefore an unforeseeable synergistic effect and not just an addition of effects. The new combinations of active substances and forms of application thus represent a valuable addition to the prior art
Die erfindungsgemäß zu verwendenden herbiziden Mittel können sowohl in kon¬ ventionellen Anbauverfahren (Reihenkulturen mit geeigneter Reihenweite) in Plantagenkulturen (z B Wein, Obst, Zitrus) sowie in Industrie- und Gleisanlagen, auf Wegen und Platzen, aber auch zur Stoppelbehandlung und beim Minimum-The herbicidal compositions to be used according to the invention can be used both in conventional cultivation methods (row crops with a suitable row width) in plantation crops (for example wine, fruit, citrus) and in industrial and track systems, on paths and squares, but also for stubble treatment and for minimum
Tillage-Verfahren eingesetzt werden Sie eignen sich weiterhin als Abbrenner (Krautabtotung z.B in Kartoffeln) oder als Defoliantien (z B in Baumwolle) Ferner sind sind sie für den Einsatz auf Bracheflachen geeignet Weitere Einsatz¬ gebiete sind Baumschulen, Forst, Grünland und ZierpflanzenbauTillage processes are used. They are also suitable as burners (killing herbs, e.g. in potatoes) or as defoliants (e.g. in cotton). They are also suitable for use on fallow land. Further areas of application are tree nurseries, forestry, grassland and ornamental plant cultivation
Als Unkräuter, die durch die erfindungsgemaßen Wirkstoffe bzw Wirkstoffkom¬ binationen gut bekämpft werden können, seien beispielsweise genanntWeeds which can be controlled well by the active compounds or combinations of active compounds according to the invention are mentioned, for example
Dikotyle Unkräuter der Gattungen Sinapis, Lepidium, Galium, Stellaria, Matri- caπa, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Soianum, Cirsium, Carduus, Sonchus, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abu- tilon, Emex, Sida, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranun- culus, Taraxum, MenthaDicotyledonous weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matri- caπa, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Soianusus, Cirsium, Cirsium, Cirsium Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Sida, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxum, Mentha
Monokotyle Unkräuter der Gattungen Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorhum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleochaπs,Monocotyledonous weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorhum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleochaπs,
Scirpus, Papalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, AperaScirpus, Papalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera
Die Verwendung der erfindungsgemaßen Wirkstoffe und Wirkstoffkombinationen ist jedoch keineswegs auf diese Gattungen beschrankt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen Der synergistische Effekt der erfindungsgemäßen Wirkstoffkombinationen ist bei bestimmten Konzentrationsverhältnissen besonders stark ausgeprägt. Jedoch kön¬ nen die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichts- teil Wirkstoff der Gruppe 1 0,001 bis 1000 Gewichtsteile, vorzugsweise 0,01 bisHowever, the use of the active compounds and combinations of active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants The synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios. However, the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 part by weight of active ingredient in group 1 accounts for 0.001 to 1000 parts by weight, preferably 0.01 to
100 Gewichtsteile und besonders bevorzugt 0,05 bis 50 Gewichtsteile Wirkstoff der Gruppe 2.100 parts by weight and particularly preferably 0.05 to 50 parts by weight of active ingredient of group 2.
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 0,05 und 5 kg Wirkstoffkombination pro ha, vorzugsweise zwischen 0,06 und 2 kg pro ha, besonders bevorzugt zwischen 0,1 und 1,0 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 0.05 and 5 kg of active ingredient combination per ha, preferably between 0.06 and 2 kg per ha, particularly preferably between 0.1 and 1.0 kg per ha.
Die erfindungsgemäßen Wirkstoffkombinationen können vor und nach dem Auf¬ laufen der Pflanzen appliziert werden, also im Vorauflauf- und Nachauflauf- Ver- fahren. Sie werden jedoch vorzugsweise im Nachauflauf-Verfahren angewandt.The active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence processes. However, they are preferably used in the post-emergence process.
Die gute herbizide Wirkung der neuen Wirkstoffkombinationen geht aus den nach¬ folgenden Beispielen hervor. Während die einzelnen Wirkstoffe in der herbiziden Wirkung Schwächen aufweisen, zeigen die Kombinationen durchweg eine sehr gute Unkrautwirkung, die über eine einfache Wirkungssummierung hinausgeht.The 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 weed action which goes beyond a simple summation of action.
Ein synergistischer Effekt liegt bei Herbiziden immer dann vor, wenn die herbi¬ zide Wirkung der Wirkstofϊkombination größer ist als die der einzelnen applizier¬ ten Wirkstoffe.A herbicide always has a synergistic effect if the herbicidal action of the active compound combination is greater than that of the individual applied active compounds.
Die zu erwartende Wirkung für eine gegebene Kombination zweier Herbizide kann wie folgt berechnet werden (vgl COLBY, S.R.: "Calculating sy- nergistic and antagonistic responses of herbicide combinations",The expected effect for a given combination of two herbicides can be calculated as follows (see COLBY, S.R .: "Calculating synergistic and antagonistic responses of herbicide combinations",
Weeds 15, Seiten 20 - 22, 1967) Wenn X = % Schädigung durch Herbizid A (Wirkstoff der Gruppe 1) bei p kg/ha Aufwandmenge und Y = % Schädigung durch Herbizid B (Wirkstoff der Gruppe 2) 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).Weeds 15, pages 20-22, 1967) If X =% damage by herbicide A (active ingredient of group 1) at a rate of p kg / ha and Y =% damage by herbicide B (active ingredient of group 2) at a rate of q kg / ha 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.
Entsprechende biologische Tests zeigten, daß die herbizide Wirkung der erfin- dungsgemäßen Wirkstoffkombinationen bei den Unkräutern größer ist als die be¬ rechnete, das heißt, daß die neuen Wirkstoffkombinationen synergistisch wirken. Corresponding biological tests showed that the herbicidal activity of the active compound combinations according to the invention in the weeds is greater than that calculated, that is to say that the new active compound combinations have a synergistic effect.
Herstellungsbeispiele:Preparation Examples:
Beispiel 1example 1
(HO)2P(O)-CH2-NH-CH2-CO-O-C2H5 (HO) 2 P (O) -CH 2 -NH-CH 2 -CO-OC 2 H 5
In eine Suspension von 200 g (1,2 Mol) N-Phosphonomethyl-glycin in 3000 ml Ethanol wird Chlorwasserstoff-Gas bis zur Sättigung eingeleitet. Dann wird dieHydrogen chloride gas is introduced into a suspension of 200 g (1.2 mol) of N-phosphonomethylglycine in 3000 ml of ethanol until saturation. Then the
Reaktionsmischung 3 Stunden unter Rückfluß erhitzt und anschließend - nach Ab¬ kühlen auf Raumtemperatur - im Wasserstrahlvakuum eingeengt. Der Rückstand wird in 1500 ml Ethanol gelöst und zu dieser Lösung wird Triethylamin (ca. 140 g) tropfenweise gegeben, bis ein Farbumschlag von rötlich-braun nach hellgelb er- folgt Das hierbei kristallin anfallende Produkt wird durch Absaugen isoliertThe reaction mixture was heated under reflux for 3 hours and then - after cooling to room temperature - concentrated in a water jet vacuum. The residue is dissolved in 1500 ml of ethanol and triethylamine (approx. 140 g) is added dropwise to this solution until the color changes from reddish brown to light yellow. The product which is obtained in this way is isolated by suction
Man erhält 201 g (85% der Theorie) N-Phosphonomethyl-glycin-ethylester vom Schmelzpunkt 203°C.201 g (85% of theory) of N-phosphonomethyl-glycine-ethyl ester with a melting point of 203 ° C. are obtained.
Die "Trocknung" des gemäß Beispiel 1 erhaltenen Produktes - d.h. die Entfernung des Alkohols - kann - gegebenenfalls mit technisch üblichen Zerkleinerungsver- fahren kombiniert - beispielsweise nach folgenden, technisch üblichen Methoden erfolgen'The "drying" of the product obtained according to Example 1 - i.e. the alcohol can be removed - if appropriate combined with technically customary comminution processes - for example by the following, technically customary methods'
Wirbelschichttrocknung, Schaufel trocknung oder Umlufttrocknung (jeweils gegebe¬ nenfalls mit technisch üblichen Zerkleinerungsverfahren, wie z.B. Luftstrahlmah¬ lung, Brechern, Walzen, Mahlen kombiniert). Fluid bed drying, blade drying or circulating air drying (in each case combined with conventional comminution processes, such as air jet milling, crushers, rollers, grinding, if appropriate).
Beispiel 2Example 2
(HO)2P(O)-CH2-NH-CH2-CO-O-C2H5 x HCl(HO) 2 P (O) -CH 2 -NH-CH 2 -CO-OC 2 H 5 x HCl
In eine Suspension von 5,1 g (30 mMol) N-Phosphonomethyl-glycin in 80 ml Ethanol wird Chlorwasserstoff-Gas bis zur Sättigung eingeleitet Dann wird die Reaktionsmischung 2 Stunden unter Ruckfluß erhitzt und anschließend im Wasser¬ strahlvakuum eingeengt Der Ruckstand wird mit Aceton verrührt und das kristal¬ line Produkt durch Absaugen isoliertHydrogen chloride gas is introduced into a suspension of 5.1 g (30 mmol) of N-phosphonomethyl-glycine in 80 ml of ethanol until saturation. The reaction mixture is heated under reflux for 2 hours and then concentrated in a water jet vacuum. The residue is mixed with acetone stirred and the kristal¬ line product isolated by suction
Man erhalt 3,0 g (43% der Theorie) N-Phosphonomethyl-glycin-ethylester-Hydro- chloπd als hygroskopische Kristalle, welche beim Erhitzen zerfließen 3.0 g (43% of theory) of N-phosphonomethyl-glycine-ethyl ester hydrochloride are obtained as hygroscopic crystals which melt when heated

Claims

PatentansprücheClaims
1 Herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer synergistischen Wirkstoffkombination bestehend aus1 herbicidal agent, characterized by an effective content of a synergistic active ingredient combination consisting of
(a) einem N-Phosphonomethyl-glycinester der Formel (I),(a) an N-phosphonomethylglycine ester of the formula (I),
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)(HO) 2 P (O) -CH 2 -NH-CH 2 -CO-OR (I)
in welcherin which
R für Alkyl steht,R represents alkyl,
oder einem Säureaddukt dieser Verbindungen ("Wirkstoff der Grup¬ pe 1 ") undor an acid adduct of these compounds ("active ingredient of group 1") and
(b) wenigstens einer Verbindung aus der Gruppe der übrigen bekannten(b) at least one compound from the group of the other known ones
Herbizide ("Wirkstoff der Gruppe 2"),Herbicides ("active substance of group 2"),
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,001 bis 1000 Gewichtsteile Wirkstoff der Gruppe 2 entfallen0.001 to 1000 parts by weight of active ingredient of group 2 per 1 part by weight of active ingredient of group 1
2 Herbizide Mittel nach Anspruch 1, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination bestehend aus2 herbicidal composition according to claim 1, characterized by an effective content of an active ingredient combination consisting of
(a) einem N-Phosphonomethyl-glycinester der allgemeinen Formel (I),(a) an N-phosphonomethylglycine ester of the general formula (I),
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)(HO) 2 P (O) -CH 2 -NH-CH 2 -CO-OR (I)
in welcherin which
R für geradkettiges oder verzweigtes Alkyl mit 1 bis 10 Kohlenstoff- atomen steht,R represents straight-chain or branched alkyl having 1 to 10 carbon atoms,
("Wirkstoff der Gruppe 1 ") und (b) einer oder zwei Verbindungen aus einer zweiten Gruppe von Herbi¬ ziden, welche die nachstehend genannten Wirkstoffe (jeweils mit "common name" benannt) enthält:("Active substance of group 1") and (b) one or two compounds from a second group of herbicides, which contains the active substances mentioned below (each named by "common name"):
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl),Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amidochlor, amidosulfuron, amiprophos (-methyl),
Amitrol, Anilofos, Asulam, Atrazin, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromo- fenoxim, Bromoxynil, Butachlor, Butamifos, Butenachlor, Butylate, Cafen- strole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimu- ron (-ethyl), Chlormethoxynil, Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazo¬ ne, Clomeprop, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyl- uron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl),Amitrol, Anilofos, Asulam, Atrazin, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromofenoximachloroxin, Bromoxil Butamifos, Butenachlor, Butylate, Cafenstrole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlormethoxynil, Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clproodo-phenolopinaflopino-Clomodinophenyl Clomeprop, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyl-uron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl),
Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Di¬ methametryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxa- prop (-ethyl), Flamprop (-isopropyl), Flamprop (-methyl), Flazasulfuron,Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methylbenz) , Fenoxaprop (-ethyl), flamprop (-isopropyl), flamprop (-methyl), flazasulfuron,
Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumi- propyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butylester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Glyphosate, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr,Fluazifop (-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurenol (n-butyl ester), fluridone, fluroxolypyr, flurprimamome, flurprimone , Glufosinate (-ammonium), glyphosate, haloxyfop (-ethoxyethyl), hexazinone, imazamethabenz (-methyl), imazamethapyr,
Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Iso- propalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Meto- sulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Mono- linuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Nitrofen, Nor- flurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxyfluorfen, Para- quat, Pendimethalin, Phenmedipham, Piperophos, Pretilachlor, Primi¬ sulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Pro- pyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyi),Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Iso-propalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Metamitaben, Metobtholonuron, Metobthiazuron, Metobthiazuron sulam, metoxuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, nitrofen, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxyfluorfen, para- quin, phena- quin, pendate Piperophos, Pretilachlor, Primi¬ sulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Pro pyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyi),
Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Seth- oxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thioben- carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-me¬ thyl), Tricyclopyr, Tridiphane, Trifluralin, Triflusulfuron,Pyrazoxyfen, pyributicarb, pyridate, pyrithiobac (-sodium), quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Seth-oxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Tchloruthiazzine, Tchloruthiazzine, Tchloruthiazine Thidiazimin, Thifensulfuron (-methyl), Thioben-carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Tricyclopyr, Tridiphane, Trifluralin, Triflusulfuron,
("Wirkstoffe der Gruppe 2"),("Active substances of group 2"),
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,01 bis 100 Ge¬ wichtsteile Wirkstoff der Gruppe 2 entfallen.1 to 1 part by weight of active ingredient in group 1 accounts for 0.01 to 100 parts by weight of active ingredient in group 2.
Herbizide Mittel nach Anspruch 1 , gekennzeichnet durch einen wirksamenHerbicidal compositions according to claim 1, characterized by an effective
Gehalt an einer Wirkstoffkombination bestehend ausContent of an active ingredient combination consisting of
(a) einem N-Phosphonomethyl-glycinester der allgemeinen Formel (I)(a) an N-phosphonomethylglycine ester of the general formula (I)
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)(HO) 2 P (O) -CH 2 -NH-CH 2 -CO-OR (I)
in welcherin which
R für geradkettiges oder verzweigtes Alkyl mit 2 bis 4 Kohlenstoff¬ atomen steht,R represents straight-chain or branched alkyl having 2 to 4 carbon atoms,
("Wirkstoff der Gruppe 1 ") und("Active substance of group 1") and
(b) einer oder zwei Verbindungen aus einer zweiten Gruppe von Herbi¬ ziden, welche die nachstehend genannten Wirkstoffe (jeweils mit "common name" benannt) enthält:(b) one or two compounds from a second group of herbicides, which contains the active substances mentioned below (each with the "common name"):
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-so¬ dium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos, Asulam, Atrazin, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromo- fenoxim, Bromoxynil, Butachlor, Butamifos, Butenachlor, Butylate, Cafen- strole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimu- ron (-ethyl), Chlormethoxynil, Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazo¬ ne, Clomeprop, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyl- uron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl),Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfureson (Bens ), Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butamifos, Butenachlor, Butylate, Cafenstrole, Carbetamide, Chlomethoxyid, Chloronbenz Chlorimu- ron (-ethyl), chloromethoxynil, chloronitrofen, chlorosulfuron, chlorotoluron, cinmethylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralide, clopyrasulfuron, cloransulyl, -curonyl, -curonyl, -curonulyl (-methyl), cyanosulam, Cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, desmedipham, dicamba, dichloroprop, diclofop (-methyl),
Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Di¬ methametryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxa- prop (-ethyl), Flamprop (-isopropyl), Flamprop (-methyl), Flazasulfuron,Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl) , Fenoxaprop (-ethyl), flamprop (-isopropyl), flamprop (-methyl), flazasulfuron,
Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumi- propyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butylester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Glyphosate, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr,Fluazifop (-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurenol (n-butyl ester), fluridone, fluroxolyr, flurprimone, flurprimone , Glufosinate (-ammonium), glyphosate, haloxyfop (-ethoxyethyl), hexazinone, imazamethabenz (-methyl), imazamethapyr,
Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Iso- propalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Meto- sulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Mono- linuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Nitrofen, Nor- flurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxyfluorfen, Para- quat, Pendimethalin, Phenmedipham, Piperophos, Pretilachlor, Primi¬ sulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Pro- pyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyl),Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Iso-propalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Metamitaben, Metobtholonuron, Metobthiazuron, Metobthiazuron sulam, metoxuron, metribuzin, metsulfuron (-methyl), Molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, nitrofen, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxyfluorfen, para- quin, phena- quin, pendate Piperophos, Pretilachlor, Primi¬ sulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Pro pyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyl),
Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Seth- oxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thioben- carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-me¬ thyl), Tricyclopyr, Tridiphane, Trifluralin, Triflusulfuron,Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Seth-oxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (Sulfometuron) Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thioben-carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-me¬, Trifluryl, Trifluron, Trifluron), Tricyl
("Wirkstoffe der Gruppe 2"),("Active substances of group 2"),
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,05 bis 50 Ge- wichtsteile Wirkstoff der Gruppe 2 entfallen Herbizide Mittel nach Anspruch 1, dadurch gekennzeichnet, daß sie als Wirkstoff der Gruppe 1 N-Phosphonomethylglycin-ethylester enthalten1 part by weight of active ingredient of group 1 accounts for 0.05 to 50 parts by weight of active ingredient of group 2 Herbicidal compositions according to claim 1, characterized in that they contain N-phosphonomethylglycine ethyl ester as active ingredient of group 1
Verwendung von Wirkstoffkombinationen gemäß Ansprüchen 1-4 zur Be¬ kämpfung von UnkrautUse of active ingredient combinations according to claims 1-4 for combating weeds
Verfahren zur Bekämpfung von Unkraut, dadurch gekennzeichnet, daß man eine Wirkstoffkombination gemäß Ansprüchen 1-4 auf Unkraut oder seinen Lebensraum einwirken laßtProcess for controlling weeds, characterized in that an active ingredient combination according to claims 1-4 is allowed to act on weeds or their habitats
Verfahren nach Anspruch 6, dadurch gekennzeichnet, daß man die Wirk- stoffkombinationen in Aufwandmengen zwischen 0,05 und 5 kg pro ha, vorzugsweise zwischen 0,06 und 2 kg pro ha, besonders bevorzugt zwi¬ schen 0, 1 und 1 ,0 kg pro ha anwendet A method according to claim 6, characterized in that the active substance combinations in application rates between 0.05 and 5 kg per ha, preferably between 0.06 and 2 kg per ha, particularly preferably between 0.1 and 1.0 kg per hectare
PCT/EP1997/000732 1996-02-29 1997-02-17 Herbicidal agents based on n-phosphonomethylglycine esters WO1997031535A1 (en)

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