DE19607633A1 - Herbicidal agents based on N-phosphonomethyl-glycine esters - Google Patents

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

The invention relates to new herbicidal compositions which are pure - not formulated - N-phosphonomethyl-glycine esters and dissolved in water or dis pergiert - previously formulated - other known herbicidal Ver bindings or combinations of such known herbicidal active Ver bindings are made.

It is known that some N-phosphonomethyl-glycine alkyl esters are herbicidal have properties and - generally in formulated application forms, d. H. combined with certain additives - to kill unwanted ones Plants can be used (cf. DE 21 52 826, DE 21 66 573, US 3977860). That pure - d. H. active ingredients not formulated - in spray liquors for use However, it is not common.

It has now been found that N-phosphonomethyl-glycine esters of the general For mel (I),

(HO) ₂P (O) -CH₂-NH-CH₂-CO-O-R (1)

in which
R represents alkyl,
- As well as acid adducts of compounds of formula (I) - as pure active ingredients, ie without the use of further auxiliaries, can be added to spray liquors from known herbicides and the application forms thus prepared can be used with very good success to kill unwanted plants, being synergistic Effects can be observed.

The invention thus relates to herbicidal compositions, characterized by effective content of a synergistic combination of active ingredients 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 Group 1 ") and
• b) at least one compound from the group of the other known Herbicides ("active substance of group 2"),

where for 1 part by weight of active ingredient of group 1 0.001 to 1000 Ge important parts of Group 2 active ingredient are eliminated.

It is extremely surprising that N-phosphonomethyl-glycine esters of the general formula (I) - and acid adducts of compounds of Formula (I) - in pure, non-formulated form for use in spray liquors known, formulated herbicide active ingredients and that Spray liquors in comparison with corresponding application forms of the individual Active ingredients show extremely synergistic properties.

The possibility of the N-phosphonomethyl-glycinester of formula (I) without Ver use of formulation aids directly in spray liquors a significant simplification of the application and thus a valuable Be enrichment of the state of the art.

The invention preferably relates to herbicidal compositions through an effective content of an active ingredient combination consisting of

• a) an N-phosphonomethylglycine ester of the general formula (I), (HO) ₂P (O) -CH₂-NH-CH₂-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 contain the active compounds mentioned below (each named "common name"):
  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 ), Chloromethoxynil, chloronitrofen, chlorosulphuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron, cloransulam (-methyl), cumyluronuron, cyclosulfonate, cyclonoxamone, cyclosulfonate, cyclosulfonate, cyclosulfonate, cyclosulfuron, cyclosulfonate, cyclosulfonate, cyclosulfonate, cyclosulfonate -butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimetha metryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopym, Diuron uron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop (-ethyl), Flamprop (-isopropyl), Flamprop (-methyl), Flazasulfuron, Fluazifop (-butam), Flumetsul , Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butyl ester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen (Glyphonate), Glufonate , Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imaza methapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifac, Lactic Linoxyrifac, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifac, Lactofloxyrifacil Mefenacet, Metamitron, Metazachlor, Methabenz thiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amide, Neburon, Nitrosulfonon, Oxosulfononuron, Oxonulfonon, Oxonulfonon, Oxonulfonon, Oxonulfonon, Oxonulfonon iargyl, phos oxadiazon, oxyfluorfen, paraquat, pendimethalin, phenmedipham, Pipero, 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, Tebuturon, Tebutamon, Tebutamon Terbutryn, Thenylchlor, Thiazopyr, Thi diazimin, Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Tri allate, Triasulfuron, Tribenuron (-methyl), Tricyclopyr, Tridiphane, Trifluralin, Tri flusulfuron,
  ("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 through an effective content of an active ingredient combination consisting of

• a) an N-phosphonomethylglycine ester of the general formula (I) (HO) ₂P (O) -CH₂-NH-CH₂-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 (each with the "common name"):
  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 ), Chloromethoxynil, chloronitrofen, chlorosulphuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron, cloransulam (-methyl), cumyluronuron, cyclosulfonate, cyclonoxamone, cyclosulfonate, cyclosulfonate, cyclosulfonate, cyclosulfuron, cyclosulfonate, cyclosulfonate, cyclosulfonate, cyclosulfonate -butyl), 2,4-D, desmedipham, dicamba, dichlorprop, diclofop (-methyl), difenzoquat, diflufenican, dimefuron, dimepiperate, dimethachlor, dimetha metryn, demethenamid, dinitramine, diphenamide, diquat, dithiopyr, diurai, diuron muron, dimuron), EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, etobenzanide, fenoxaprop (-ethyl), flamprop (-isopropyl), flamprop (-methyl), flazasulfuron, fluazifop (-butam), flumetsul , Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butyl ester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen (Glyphonate), Glufonate , Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imaza methapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifac, Lactic Linoxyrifac, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifacil, Lactoxapyrifac, Lactofloxyrifacil Mefenacet, Metamitron, Metazachlor, Methabenz thiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amide, Neburon, Nitrosulfonon, Oxosulfononuron, Oxonulfononuron, Oxonulfononuron, Oxonulfonon, Oxonulfonon, diargyl, oxadiazon, oxyfluorfen, paraquat, pendimethalin, phenmedipham, pipero phos, pretilachlor, primisulfuron (-methyl), prometryn, propachlor, propanil, propaquizafop, propyzamide, prosulfocarb, prosulfuron, pyrazolonate, pyrazosulfonate, pyrazosulfonate, pyrazosulfate, pyrazosulfate, pyrazosulfate, pyrazosulfate, pyrazosulfate, pyrazosulfonate, pyrazosulfonate, pyrazosulfonate, pyrazosulfonate, pyrazosulfonate, pyrazosulfonate, pyrazosulfonate, pyrazosulfonate, pyrazosulfonate, pyrazosulfonate, pyrazosulfonate, pyrazosulfonate, pyrazolate, pyrazosulfonate , Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebuturon, Tebutamon , Terbutryn, Thenylchlor, Thiazopyr, Thi diazimin, Thifensulfiron (methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Tri allate, Triasulfuron, Tribenuron (methyl), Tricyclopyr, Tridiphane, Trifluralin, Tri flusulfuron,
  ("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.

As a particularly preferred group 1 active ingredient, N-phosphonomethyl called glycine ethyl ester.

As acid adducts in connection with the present invention, all common addition products from compounds of formula (I) and acids to ver  stand. Suitable acids are preferably strong protonic acids, such as e.g. B. hydrogen fluoride, hydrogen chloride (hydrochloric acid), hydrogen bromide, hydrogen iodide, sulfuric acid, phosphoric acid, trifluoroacetic acid, methanesulfonic acid, Ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, trifluoromethanesulfonic acid, Benzenesulfonic acid and p-toluenesulfonic acid.

The compounds of formula (I) to be used according to the invention are already known and / or can be prepared by methods known per se (cf. DE 21 52 826, DE 21 66 573, US 3977860).

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

(HO) ₂P (O) -CH₂-NH-CH₂-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. B. hydrogen chloride (hydrogen chloride), at temperatures between 40 ° C and 150 ° C and the resulting acid adduct of the compound of formula (I) - optionally after intermediate isolation with an acid binder, such as. B. triethylamine or propylene oxide, at temperatures between 0 ° C and 60 ° C (see. The preparation examples).

It has now surprisingly been found that the combination of active substances defined above ions from the N-phosphonomethyl-glycine esters of the formula (I) and those above led active ingredients of group 2 have a particularly high herbicidal activity exhibit. You can be particularly successful in semi-selective and in the non-selective area of weed control.  

Surprisingly, the herbicidal activity of the active compound according to the invention combinations of substances from the compounds of groups 1 and 2 listed above considerably higher than the sum of the effects of the individual active ingredients.

There is therefore an unforeseeable synergistic effect and not only an addition. The new drug combinations and application form Men thus represent a valuable addition to the state of the art.

The herbicidal compositions to be used according to the invention can be used both in con conventional cultivation methods (row crops with a suitable row size) in Plantation crops (e.g. wine, fruit, citrus) as well as in industrial and track systems, on paths and squares, but also for stubble treatment and at the minimum Tillage method can be used. They are still suitable as burners (Herb killing e.g. in potatoes) or as defoliantia (e.g. in cotton). They are also suitable for use on fallow land. Further use areas are tree nurseries, forest, grassland and ornamental plant growing.

As weeds, which are caused by the active substances or active ingredient com Combinations can be fought well, for example:

Dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matri caria, anthemis, galinsoga, chenopodium, urtica, senecio, alnaranthus, portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Solanum, Cirsium, Carduus, Sonchus, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abu tilon, Emex, Sida, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranun culus, taraxum, mentha.

Monocot weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorhum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Papalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

The use of the active substances and combinations of active substances according to the invention is by no means limited to these genera, but extends into the same way for other plants.  

The synergistic effect of the active compound combinations according to the invention is certain concentration ratios particularly pronounced. However, the weight ratios of the active ingredients in the active ingredient combinations relatively large areas can be varied. Generally 1 weight is used Part of active ingredient of group 1 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 in be varied within a certain range; they hang u. a. of the weather and the 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 used before and after run of the plants are applied, i.e. in the pre-emergence and post-emergence ver drive. However, they are preferably used in the post-emergence process.

The good herbicidal activity of the new combinations of active ingredients follows from the following examples. While the individual active ingredients in the herbicidal The combinations all have a very weak effect good weed action that goes beyond a simple addition of effects.

A herbicide always has a synergistic effect if the herbicide zide effect of the active ingredient combination is greater than that of the individual applicator active ingredients.

The expected effect for a given combination of two herbicides can be calculated as follows (cf. COLBY, SR: "Calculating sy nergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
If X =% damage from herbicide A (active ingredient of group 1) at p kg / ha application rate
and Y =% damage by herbicide B (active ingredient of group 2) at an application 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 combination is in its effect is superadditive, that is, it shows a synergistic effect.

Appropriate biological tests showed that the herbicidal activity of the inventions active ingredient combinations according to the weeds is greater than the be calculated, that is, that the new active ingredient combinations act synergistically.  

Manufacturing examples example 1

(HO) ₂P (O) -CH₂-NH-CH₂-CO-O-C₂H₅

In a suspension of 200 g (1.2 mol) of N-phosphonomethyl-glycine in 3000 ml Ethanol is introduced to hydrogen chloride gas until saturation. Then the Reaction mixture heated under reflux for 3 hours and then - after Ab cool to room temperature - concentrated in a water jet vacuum. The residue is dissolved in 1500 ml of ethanol and triethylamine (approx. 140 g) added dropwise until a color change from reddish brown to light yellow follows. The crystalline product is isolated by suction.

201 g (85% of theory) of N-phosphonomethylglycine ethyl ester are obtained Melting point 203 ° C.

The "drying" of the product obtained according to Example 1 - ie the removal of the alcohol - can - if appropriate combined with technically customary comminution processes - be carried out, for example, by the following, technically customary methods:
Fluidized bed drying) paddle drying or forced-air drying (in each case, if necessary, combined with conventional comminution processes such as air jet grinding, crushers, rollers, grinding).

Example 2

(HO) ₂P (O) -CH₂-NH-CH₂-CO-O-C₂H₅ x HCl

In a suspension of 5.1 g (30 mmol) of N-phosphonomethyl-glycine in 80 ml Ethanol is introduced to hydrogen chloride gas until saturation. Then the The reaction mixture was heated under reflux for 2 hours and then in water jet vacuum concentrated. The residue is stirred with acetone and the crystal line product isolated by suction.

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

Claims (7)

1. Herbicidal agents, characterized by an effective content of a synergistic combination of active ingredients consisting of

• a) an N-phosphonomethylglycine ester of the formula (I), (HO) ₂P (O) -CH₂-NH-CH₂-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 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.

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) ₂P (O) -CH₂-NH-CH₂-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 with the "common name"):
  Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Alnitrol, Anilofos, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate-Bensulfuron) Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromo fenoxim, Bromoxynil, Butachlor, Butamifos, Butenachlor, Butylate, Cafen strole, Carbetamide, Chlomethoxyfen, Chlorambenimuazon, Chloramben, Chlorid ethyl), Chlormethoxynil, chlornitrofen, ne chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clodinafop (-propargyl), Clomazo, clomeprop, clopyralid, Clopyrasulfuron, cloransulam (-methyl), Cu myluron, 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, Douron Dai muron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxa prop (-ethyl), Flamprop (-isopropyl), Flamprop (-methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, flumiclorac (-pentyl), flumioxazin, flumi propyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxain, flupropacil, flurenol (n-butyl ester), fluridone, fluroxypyr, flurprimidol, flurtamonosium, fomesafen Glyphosate, Haloxyfop (-ethoxy ethyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosuifuron, Ioxynil, Iso propalin, Isoproturon, Isoxaben, Isoxaflutop, Mylapurol, Isoxa Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Meto sulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Mono linuron, Naproanilide, Napropamide, Orburon, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Narburon, Nitruron, Nitruron, Narburon, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nitruron, Nicuron , O xadiargyl, quat oxadiazon, oxyfluorfen, Para, pendimethalin, phenmedipham, piperophos, pretilachlor, Primi Sulfuron (-methyl), prometryn pyzamide, propachlor, propanil, propaquizafop, Pro, prosulfocarb, prosulfuron, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfüron, Seth oxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebuturam , Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thioben carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-me thyl), Tricyclopyr, Tridiphane, Triflulfuron, Trifluralin
  ("Active substances of group 2"),
  1 to 1 part by weight of active ingredient of group 1 accounts for 0.01 to 100 parts by weight of active ingredient of group 2.

3. 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) ₂P (O) -CH₂-NH-CH₂-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-Benfuresate (Bensulfuron) , Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromo fenoxim, Bromoxynil, Butachlor, Butamifos, Butenachlor, Butylate, Cafen strole, Carbetamides, Chlomethoxyon, Chloronbene, Chlorambene, Chlorambene, Chlorambene, Chlorambene, Chlorambene -ethyl) Chlormethoxynil, chlornitrofen, chlorosulfuron, 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), Difenzoquat, Diflufenican, Dimefiron, Dimepiperate, Dimethachlor, Di methametryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyrronur, Di (Daimu ron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxa prop (-ethyl), Flamprop (-isopropyl), Flamprop (-methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumi propyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butyl ester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamonosium, Fomesafen Glyphosate, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Iso propalin, Isoproturon, Isoxaben, Isoxaflutop, Mactolopyronac, Moxa , Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Meto sulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Mono linuron, Naproanilide, Napropamide, Neburon, Nourazonuronuron, Nicosulfononuron, Nicosofenuronuron Oxadi argyl, oxadiazon, oxyfluorfen, para quat, pendimethalin, phenmedipham, piperophos, pretilachlor, primi sulfuron (-methyl), prometryn, propachlor, propanil, propaquizafop, pro pyzamide, prosulfocarb, prosulfuron, pyrazolate, pyrazosulfuron (pyrazosulfuron) , Pyridate, Pyrithiobac (sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Seth oxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (methyl), Sulfosate, Tebuturon, Tebutamon Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thioben carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (me thyl), Tricyclopyr, Tridiphane, Trifluralin, Triflusulfuron
  ("Active substances of group 2"),
  with 1 part by weight of active ingredient of group 1 0.05 to 50 parts by weight of active ingredient of group 2.

4. Herbicidal compositions according to claim 1, characterized in that they are as Active ingredient of group 1 contain N-phosphonomethylglycine ethyl ester. 5. Use of active ingredient combinations according to claims 1-4 for loading weed control. 6. A method of combating weeds, characterized in that an active ingredient combination according to claims 1-4 on weed or its Living space. 7. The method according to claim 6, characterized in that the effect combinations of substances in application rates between 0.05 and 5 kg per ha, preferably between 0.06 and 2 kg per ha, particularly preferably between between 0.1 and 1.0 kg per ha.