WO1997031535A1

WO1997031535A1 - Herbicidal agents based on n-phosphonomethylglycine esters

Info

Publication number: WO1997031535A1
Application number: PCT/EP1997/000732
Authority: WO
Inventors: Hans-Jochem Riebel; Uwe Priesnitz; Raphael Wieschollek; Markus Dollinger; Ingo Wetcholowsky
Original assignee: Bayer Aktiengesellschaft
Priority date: 1996-02-29
Filing date: 1997-02-17
Publication date: 1997-09-04
Also published as: DE19607633A1; AU1873797A

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

Herbicidal agents based on N-phosphonomethyl-glvcinestern

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.

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.

It has now been found that N-phosphonomethylglycine esters of the general formula (I)

(HO) ₂ P (O) -CH ₂ -NH-CH ₂ -CO-OR (I)

in which

R represents alkyl,

- and acid adducts of compounds of the formula (I) -

as 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

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

(b) at least one compound from the group of the other known herbicides (“active ingredient of group 2”),

0.001 to 1000 parts by weight of active ingredient of group 2 per 1 part by weight of active ingredient of group 1.

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.

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.

The invention preferably relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of

(a) an N-phosphonomethylglycine ester of the general formula (I),

(HO) ₂ P (O) -CH ₂ -NH-CH ₂ -CO-OR (I)

in which

R represents straight-chain or branched alkyl having 1 to 10 carbon atoms,

("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,

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-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, 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, triallates, triasulfuron, tribenuron (-methyl), tricyclopyr, tridiphane, trifluralin, triflusulfuron,

("Active substances of group 2")

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.

The invention particularly relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of

(a) an N-phosphonomethylglycine ester of the general formula (I)

(HO) ₂ P (O) -CH ₂ -NH-CH ₂ -CO-OR (I)

in which

R represents straight-chain or branched alkyl having 2 to 4 carbon atoms,

("Active substance of group 1") and

(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, Atrazine, Azimsulfuron, Benazolin, Benfuresate-Bensulfuron (Bensulfuron)

Bensulide, 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, 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-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, Tchlorothiazopine, Terbutrynopine diazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), tricyclopyr, tridiphane, trifluralin, triflusulfuron,

("Active substances of group 2")

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.

A particularly preferred group 1 active ingredient is N-phosphonomethylglycine ethyl ester

In 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,

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)

The N-phosphonomethylglycine esters of the general formula (I) are obtained if N-phosphonomethylglycine of the formula (II)

(HO) ₂ P (O) -CH ₂ -NH-CH ₂ -COOH (II)

with an alcohol of formula (III)

HO-R (III)

in which

R has the meaning given above,

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)

It 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

There 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

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 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

Weeds which can be controlled well by the active compounds or combinations of active compounds according to the invention are mentioned, for example

Dicotyledonous 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

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, Apera

However, 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 parts by weight and particularly preferably 0.05 to 50 parts by weight of active ingredient of group 2.

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.

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.

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.

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 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, 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).

If the actual damage is greater than calculated, the effect of the combination is super-additive, that is, it shows a synergistic effect.

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.

Preparation Examples:

example 1

(HO) ₂ P (O) -CH ₂ -NH-CH ₂ -CO-OC ₂ H ₅

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

The 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

201 g (85% of theory) of N-phosphonomethyl-glycine-ethyl ester with a melting point of 203 ° C. are obtained.

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'

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).

Example 2

(HO) ₂ P (O) -CH ₂ -NH-CH ₂ -CO-OC ₂ H ₅ x HCl

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

3.0 g (43% of theory) of N-phosphonomethyl-glycine-ethyl ester hydrochloride are obtained as hygroscopic crystals which melt when heated

Claims

1 herbicidal agent, characterized by an effective content of a synergistic active ingredient combination consisting of

(a) an N-phosphonomethylglycine ester of the formula (I),

(HO) ₂ P (O) -CH ₂ -NH-CH ₂ -CO-OR (I)

in which

R represents alkyl,

or an acid adduct of these compounds ("active ingredient of group 1") and

(b) at least one compound from the group of the other known ones

Herbicides ("active substance of group 2"),

0.001 to 1000 parts by weight of active ingredient of group 2 per 1 part by weight of active ingredient of group 1

2 herbicidal composition according to claim 1, characterized by an effective content of an active ingredient combination consisting of

(a) an N-phosphonomethylglycine ester of the general formula (I),

(HO) ₂ P (O) -CH ₂ -NH-CH ₂ -CO-OR (I)

in which

R represents straight-chain or branched alkyl having 1 to 10 carbon atoms,

("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),

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, 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, 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, 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, Tchloruthiazzine, Tchloruthiazzine, Tchloruthiazine Thidiazimin, Thifensulfuron (-methyl), Thioben-carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Tricyclopyr, Tridiphane, Trifluralin, Triflusulfuron,

("Active substances of group 2"),

Herbicidal compositions according to claim 1, characterized by an effective

Content of an active ingredient combination consisting of

(a) an N-phosphonomethylglycine ester of the general formula (I)

(HO) ₂ P (O) -CH ₂ -NH-CH ₂ -CO-OR (I)

in which

R represents straight-chain or branched alkyl having 2 to 4 carbon atoms,

("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 with the "common name"):

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, 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, 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, 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 (Sulfometuron) Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thioben-carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-me¬, Trifluryl, Trifluron, Trifluron), Tricyl

("Active substances of group 2"),

1 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

Use of active ingredient combinations according to claims 1-4 for combating weeds

Process for controlling weeds, characterized in that an active ingredient combination according to claims 1-4 is allowed to act on weeds or their habitats

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