Method for controlling herbicide resistant weeds

Abstract

The present invention relates to methods and uses for controlling herbicide resistant weed biotypes by applying a herbicidal malonamide of formula (I), or any of its agriculturally acceptable salts, stereoisomers and tautomers. The methods are particularly suitable for the protection of crops.

Description

[0001] Method for controlling herbicide resistant weeds

[0002] The present invention relates to methods for controlling herbicide resistant weed biotypes by applying a herbicidal malonamide of formula (I) or any of its agriculturally acceptable salts, stereoisomers, or tautomers.

[0003] The methods are particularly suitable for the protection of crops.

[0004] Background of the invention

[0005] Herbicide resistant weeds have become a significant concern in agriculture over the past few decades. These are weeds that have developed the ability to survive and reproduce despite being exposed to herbicides that were previously effective in controlling them. The occurrence of herbicide resistant weeds has been steadily increasing due to several factors, including the overreliance on a limited number of herbicides, improper herbicide use practices, and the natural ability of weeds to adapt and evolve.

[0006] To address this issue, various methods have been developed for controlling herbicide resistant weeds. Integrated Weed Management (I M) is a comprehensive approach that combines multiple strategies to minimize the reliance on herbicides alone. This approach includes practices such as crop rotation, tillage, mechanical weed control, cover cropping, and targeted herbicide application. By diversifying weed control methods, IWM aims to reduce the selection pressure on weeds and slow down the development of resistance.

[0007] Additionally, the use of herbicide mixtures with different modes of action can help delay the onset of herbicide resistance. By combining herbicides that target weeds through different biological pathways, the likelihood of resistance evolution decreases.

[0008] Herbicide resistance within weeds, in particular grass weeds such as, for example, Alopecurus myosuroides (ALOMY), Apera spica-venti (APESV), Echinochloa crus-gali (ECHCG) or Lolium species (LOLSS), but also broadleaf weeds like Amaranthus species (AMASS) and Raphanus species (RAPSS), has become a major concern for farmers, resulting in dramatic weed control problems, for example in cereal crops. Herbicides from the group of 5- enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, Acetyl-CoA carboxylase (ACC) inhibitors and acetolactate synthase (ALS) inhibitors are most affected by resistance evolution but also various other types of herbicides.

[0009] Accordingly, there is a strong demand to find new methods and uses to substitute or complement current agricultural practice in order to control herbicide resistant weeds and to reduce the risk of developing further resitant biotypes (BT). WO2021 / 170464 discloses certain malonamide compounds and compositions comprising the same for controlling unwanted vegetation. While these malonamide compounds show excellent herbicidal activity as well as certain selectivity in crops, there remains a need for methods to control weeds, especially herbicide resistant weeds, in a broad variety of different crops.

[0010] Accordingly, there is still a need to further develop practices for preventing, delaying or managing herbicide resistance in weeds.

[0011] We have found that this object and further objects are achieved by applying to the vegetation or the locus thereof or to the soil or water a herbicidally effective amount of a herbicidal malonamide (Herbicide A), selected from a compound of formula (I) wherein

[0012] X1is fluorine or chlorine,

[0013] X2is fluorine or chlorine,

[0014] R is hydrogen, (Ci-Ce)-alkyl or (Cs-Cej-cycloalkyl, or their agriculturally acceptable salts, stereoisomers and tautomers.

[0015] Summary of the invention

[0016] An object of the present invention lies in the effective control of herbicide-resistant weed biotypes, especially in the effective control of herbicide-resistant grass and / or broadleaf weeds.

[0017] It is also an object of the present invention to improve the herbicidal activity against undesirable harmful plants and / or the compatibility with the useful plants (in particular crop plants).

[0018] Surprisingly, it has now been found that herbicide resistant weeds are efficiently controlled by applying certain malonamide compounds.

[0019] Accordingly, in one aspect of the invention, there is provided a method for controlling undesirable vegetation, which comprises applying to the vegetation or the locus thereof or applying to the soil or water, a herbicidally effective amount of a herbicidal malonamide (Herbicide A), selected from a compound of formula (I) wherein

[0020] X1is fluorine or chlorine,

[0021] X2is fluorine or chlorine,

[0022] R is hydrogen, (Ci-Ce)-alkyl or (Cs-CeJ-cycloalkyl, or their agriculturally acceptable salts, stereoisomers and tautomers, and wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype.

[0023] The term "herbicidal ly effective amount" denotes an amount of the active ingredients, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated cultivated plant or material, the climatic conditions and the specific composition according to the invention used.

[0024] The terms "plants" and "vegetation", as used herein, include germinant seeds, emerging seedlings, plants emerging from vegetative propagules, and established vegetation.

[0025] The terms "undesirable vegetation", "harmful plants", "unwanted plants”, "weeds” and "weed species”, as used herein, are synonyms.

[0026] The term „ resistant weed biotype" refers to individuals within a species that are best adapted and not susceptible to the application of a specific herbicide at the highest registered application rate. Resistance of weed biotypes to herbicides is a consequence of naturally occurring mutations and evolutionary processes.

[0027] The terms "controlling" and "combating", as used herein, are synonyms, referring to inhibition of growth, control of growth, reduction of growth or complete destruction of weeds. In the context of the present invention, weed control means reducing or preventing the emergence or growth of the undesirable vegetation.

[0028] The term "locus", as used herein, means the area in which the vegetation or plants are growing or will grow, typically a field.

[0029] The term "resistant weed(s)” as used herein means weeds, which are not controlled by the application of a herbicide used at the highest registered field rate, whereas the respective sensitive biotype is controlled at that use rate. About 250 weed species have been confirmed to be resistant to at least one herbicide mode or site of action. Examples of herbicides to which resistance was observed are listed by the HRAC, Herbicide Resistance Action Committee, with the associated mode of action: https: / / www.weedscience.org / Pages / Herbicide.aspx. HRAC group 1, acetyl CoA carboxylase (ACCase) inhibitors: Alloxydim, Butroxydim, Clodinafop-propargyl, Clofop, Cloproxydim, Cy- cloxydim, Cyhalofop-butyl, Diclofop-methyl, Fenoxaprop-ethyl, Fenthiaprop, Fluazifop-butyl, Haloxyfop-methyl, Isoxa- pyrifop, Metamifop, Metproxybicyclone, Pinoxaden, Profoxydim, Quizalofop-ethyl, Sethoxydim, Tepraloxydim, Tralkoxydim. Acetolactate synthase (ALS) inhibitors (HRAC Group 2): Amidosulfuron, Azimsulfuron, Bensulfuron- methyl, Bispyribac-sodium, Chlorimuron-ethyl, Chlorsulfuron, Chloransulam-methyl, Cinosulfuron, Cloransulam-me- thyl, Cyclosulfamuron, Diclosulam, Ethametsulfuron-methyl, Ethoxysulfuron, Flazasulfuron, Flucarbazone-Na, Fluce- tosulfuron, Flumetsulam, Flupyrsulfuron-methyl-Na, Florasulam, Foramsulfuron, Halosulfuron-methyl, Imaza- methabenz-methyl, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, lodosulfuron-methyl-Na, Mesosulfuron- methyl, Metazosulfuron, Metsulfuron-methyl, Metosulam, Nicosulfuron, Orthosulfamuron, Oxasulfuron, Penoxsulam, Primisulfuron-methyl, Propoxycarbazone-Na, Propyrisulfuron, Prosulfuron, Pyrazosulfuron-ethyl, Pyriminobac-me- thyl, Pyrimisulfan, Pyroxsulam, Pyriftalid, Pyrithiobac-sodium, Rimsulfuron, Sulfometuron-methyl, Sulfosulfuron, Thiencarbazone-methyl, Thifensulfuron-methyl, Trifloxysulfuron-Na, Triflusulfuron-methyl, Triafamone, Tribenuron- methyl, Trisosulfuron. Inhibitors of photosynthesis at photosystem II (PS II) (HRAC Groups 5 and 6): Amicarbazone, Ametryne, Atraton, Atrazine, Aziprotryn, Benzthiazuron, Bentazon, Bromacil, Bromofenoxim, Bromoxynil, Brompyra- zon, Bromuron, Buturon, Chloranocryl, Chlorazine, Chlorbromuron, Chlorotoluron, Chloroxuron, Chlorprocarb, Chloridazon, CP 17029, Cyanazine, Cyprazine, Desmedipham, Desmetryne, Dicryl, Difenoxuron, Dimefuron, Di- methametryn, Dipropetryn, Diuron, Eglinazine-ethyl, Ethidimuron, Ethiozin, Fluometuron, Fluothiuron, Hexazinone, Ioxynil, Ipazine, Isomethiozin, Isoproturon, Isouron, Lenacil, Linuron, Metabenzthiazuron, Metabromuron, Metam- itron, Metobenzuron, Metobromuron, Methabenzthiazuron, Methoprotryn, Monolinuron, Monuron, Neburon, Paraflu- ron, Pentanochlor, Phenmedipham, Phenisopham, Phenyldiazine, Procyazine, Proglinazine-ethyl, Prometon, Prome- tryne, Propazine, Propanil, Pyrazon, Pyridate, Sebuthylazine, Siduron, Simazine, Simetryne, Tebuthiuron, Terbacil, Terbumeton, Terbutryne, Terbutylazine, Thiazafluron. Photosystem I (PS I) inhibitors (HRAC Group 22): Cyperquat, Diquat, Morfamquat, Paraquat. Protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group 14): Acifluorfen, Azaf- enidin, Bifenox, Butafenacil, Carfentrazone-ethyl, Chlorphthalim, Chlomethoxyfen, Chlornitrofen, Cinidon-ethyl, Epyri- fenacil, Flumiclorac-pentyl, Flumioxazin, Flumipropyn, Fluoronitrofen, Fluorodifen, Fluoroglycofen-ethyl, Fomesafen, Fluthiacet-methyl, Nitrofen, Oxyfluorfen, Oxadiazon, Oxadiargyl, Pentoxazone, Pyraclonil, Pyraflufen-ethyl, Saflufenacil, Sulfentrazone, Tiafenacil, Trifl udimoxazin. 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group 27): Benzobicyclon, Benzofenap, Bicyclopyrone, Dioxopyritrine, Fenquinotrione, Isoxaflutole, Mesotrione, Pyrasulfotole, Pyrazolynate, Pyrazoxyfen, Sulcotrione, Tembotrione, Tefuryltrione, Tolpyralate, Topramezone. Phytoene desaturase (PDS) inhibitors (HRAC Group 12): Beflubutamid, Diflufenican, Flurochloridone, Fluridone, Flurtamone, Norflurazon, Picolinafen Rimisoxafen. Lycopene cyclase inhibitors (HRAC Group 34): Amitrole. DOXP synthase inhibitors (HRAC Group 13): Bixlozone, Clomazone. 5-enolpyruvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group 9): Glyphosate. Glutamine synthetase inhibitors (HRAC Group 10): Glufosinate-ammonium, L- Glufosinate-ammonium, Bialaphos / bilanafos. Dihydropteroate synthase (DHP) inhibitors (HRAC Group 18): Asulam. Inhibitors of microtubuli assembly (HRAC Group 3): Benefin, Butamifos, Butralin, Chlorthal-dimethyl=DCPA, Dinitramine, Dithiopyr, Ethalfluralin, Fluchloralin, Flumioxazin, Icafolin-methyl, Isopropalin, Nitralin, Oryzalin, Pendimethalin, Prodiamine, Profluralin, Propyzamide=pronamide, Thiazopyr, Trifluralin. Inhibitors of mitosis / microtubuli organization (HRAC Group 23): Barban, Carbetamide, Chlorbufam, Chlorpropham, Propham, Swep. Very long chain fatty acid (VLCFA) inhibitors (HRAC Group 15): Acetochlor, Alachlor, Allidochlor=CDA, Anilofos, Benfuresate, Butachlor, Bu- tenachlor, Butylate, Cafenstrole, Cycloate, Delachlor, Dimepiperate, Diethatyl-ethyl, Dimethachlor, Dimethenamid, EPTC, Ethofumesate, Esprocarb, Fenoxasulfone, Fentrazamide, Flufenacet, Ipfencarbazone, Indanofan, Mefenacet, Metazachlor, Metolachlor, Molinate, Orbencarb, Pebulate, Pethoxamid, Piperophos, Pretilachlor, Propachlor, Pro- pisochlor, Prynachlor, Pyroxasulfone, Prosulfocarb, Thiobencarb (=Benthiocarb), Thenylchlor, Tiocarbazil, Tridip- hane, Tri-allate, Vernolate. Inhibitors of cell wall synthesis (HRAC Group 29): Chlorthiamid, Dichlobenil, Flupoxam, Indaziflam, Isoxaben, Triaziflam. Uncoupler (membran disruption) (HRAC Group 24): Dinosam, Dinoseb, Dinoterb, DNOC, Etinofen, Medinoterb. Synthetic auxins (HRAC Group 4): Aminocyclopyrachlor, Aminopyralid, Benazolin- ethyl, Chloramben, Chlorfenac=fenac, Chlorfenprop, Clomeprop, Clopyralid, Dicamba, Dichlorprop, Fluroxypyr, Florpyrauxifen, Halauxifen, Halauxifen-methyl, MCPA, MCPBDicamba, Mecoprop, Picloram, Quinclorac, Quinmerac, TBA, Triclopyr, 2,4-D, 2,4-DB. Auxin transport inhibitors (HRAC Group 19): Diflufenzopyr-sodium, Naptalam. Dihy- droorotate dehydrogenase (DHODH) inhibitors (HRAC Group 28): Tetflupyrolimet. Solanesyl diphosphate synthase (SDS) inhibitors (HRAC Group 32): Aclonifen. Serine-threonine protein phosphatase inhibitors (HRAC Group 31): Endothal. Fatty acid thioesterase (FAT) inhibitors (HRAC Group 30): Cinmethylin, Methiozolin. homogentisate solanesyltransferaseand (HST) inhibitors (HRAC Group 33): Cyclopyrimorate. Herbicides with unknown mode of action (HRAC Group 0): Bensulide, Bromobutide, Cacodylic acid, CAM, CAMA, Dalapon, Difenzoquat, Diphenamid, DSMADymron=Daimuron, Etobenzanid, Flamprop-m, Flupropanate, Fosamine, Mefluidide, Methyldymron, Monalide, MSMA, Naproanilide, Napropamide, Oleic acid, Oxaziclomefone, Pelargonic acid, Pyributicarb, Quinoclamine, Tebu- tam.

[0030] The present invention also relates to the use of a herbicidal malonamide (Herbicide A), selected from a compound of formula (I) wherein

[0031] X1is fluorine or chlorine,

[0032] X2is fluorine or chlorine,

[0033] R is hydrogen, (Ci-Ce)-alkyl or (Cs-CeJ-cycloalkyl, or their agriculturally acceptable salts, stereoisomers and tautomers, for controlling herbicide resistant weed biotypes.

[0034] In the methods and uses according to the present invention, the required application rate of the herbicidal malonamide (Herbicide A), depends on the density of the undesired vegetation, in particular of herbicide resistant weeds, on the development stage of these plants, on the climatic conditions of the location where Herbicide A or a compsition comprising Herbicide A is used and on the application method.

[0035] In general, the application rate of the herbicidal malonamide (Herbicide A), is from 1 to 300 g / ha, preferably from 2 to 200 g / ha, more preferably from 4 to 150 g / ha of active substance.

[0036] The herbicidal malonamide (Herbicide A) or a compsition comprising Herbicide A can generally be applied to weeds at any growth stage with good results. In one embodiment, Herbicide A or a compsition comprising Herbicide A is applied up to BBCH growth stage 37 of the weeds, showing effective weed control, in particular of herbicide resistant weeds.

[0037] Weeds, which are controlled by the methods and uses according to the present invention include monocots and dicots, preferably monocots.

[0038] The present invention relates to methods and uses for controlling herbicide resistant weeds in crops.

[0039] In the methods and uses according to the present invention for controlling herbicide resistant weeds in crops, the Herbicide A and compositions comprising Herbicide A can generally be applied post-emergence of the crop, up to BBCH growth stage 29-37 of the crop.

[0040] BBCH growth stages are as defined in "Growth stages of mono- and dicotyledonous plants”, BBCH Monograph edited by Uwe Meier Julius Kuhn-lnstitut (JKI), Open Agrar Repositorium, Quedlinburg 2018 DOI: 10.5073 / 20180906- 074619 ISBN: 978-3-95547-071-5.

[0041] The methods and uses of the present invention for controlling herbicide resistant weeds in crops have several advantages over conventional methods or methods applying structurally similar herbicides:

[0042] The method of the present invention provides for superior control of herbicide resistant weed biotypes, in particular of monocotyledonous weeds.

[0043] - The method of the present invention shows superior crop compatibility with certain conventional crop plants, in particular with spring wheat, winter wheat, spring barley, winter barley, durum, spelt wheat, turf and rice.

[0044] - The method of the invention provides for an adequate duration of herbicidal activity, even under difficult weathering conditions, which allows a more flexible application and minimizes the risk of weeds escaping.

[0045] Further embodiments of the invention are evident from the description, the examples and the claims. It is to be understood that the features mentioned above and still to be illustrated below of the subject matter of the invention can be applied not only in the combination given in each particular case but also in other combinations, without leaving the scope of the invention. Detailed description of the invention

[0046] The preferred embodiments of the invention mentioned herein below have to be understood as being preferred either independently from each other or in combination with one another.

[0047] As used herein, the term "composition” refers to compositions or mixtures comprising a herbicidal malonamide of formula (I), Herbicide A. Different salts of the herbicidal malonamide are considered as the same herbicide compound.

[0048] As used herein, the term "agrochemical composition” refers to compositions or mixtures comprising a herbicidal malonamide of formula (I), Herbicide A, and one or more auxiliaries customary for crop protection compositions.

[0049] As used herein "herbicide" refers to one or more agents, compounds and / or compositions having herbistatic and / or herbicidal activity.

[0050] As used herein, the terms "undesirable vegetation", "undesirable species", "undesirable plants", "harmful plants", "unwanted plants”, "undesirable weeds", "volunteer plants”, "weeds”, "weed species” or "harmful weeds" are used synonymously.

[0051] As used herein, "post-emergence” refers to an herbicide treatment that is applied to an area after the crop has germinated and emerged from the ground or growing medium.

[0052] As used herein, "pre-emergence” refers to an herbicide treatment that is applied to an area before the crop has emerged from the ground or growing medium.

[0053] Surprisingly, it has been found that a herbicidally effective amount of a herbicidal malonamide (Herbicide A) selected from a compound of formula (I) wherein

[0054] X1is fluorine or chlorine,

[0055] X2is fluorine or chlorine,

[0056] R is hydrogen, (Ci-Ce)-alkyl or (Ca-CeJ-cycloalkyl, or their agriculturally acceptable salts, stereoisomers and tautomers, provides effective control of herbicide-resistant weed biotypes. In addition, the present invention is directed to a method for controlling herbicide resistant weeds in crops, wherein an effective amount of a herbicidal malonamide of formula (I) (Herbicide A) is applied to the crop cultivation area, specifically to the vegetation or the locus thereof or to the soil or water.

[0057] The terms used for organic groups in the definition of the variables are collective terms which represent the individual members of these groups of organic units.

[0058] The prefix Cx-Cydenotes the number of possible carbon atoms in the particular case. All hydrocarbon chains can be straight-chain or branched.

[0059] For example, the term “Ci-C4-alkyl” denominates a group of linear or branched saturated hydrocarbon radicals having from 1 to 4 carbon atoms, e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl.

[0060] The term " (Ca-CeJ-cycloalkyl" denominates a monocyclic saturated hydrocarbon group having 3 to 6, in particular 4 to 5, carbon ring members, e.g. cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0061] In the context of the present invention, the herbicidal malonamides (Herbicide A) can be employed as such or, e.g. if they have a free carboxyl group (i.e. R = hydrogen), in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.

[0062] Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by C1-C4- alkyl, hydroxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sul- foxonium, and finally the salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[0063] Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. If a Herbicide A is capable of forming geometrical isomers, for example E / Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the methods or uses according to the invention.

[0064] If a Herbicide A as described herein has one or more centers of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the combinations or compositions according to the invention.

[0065] If a Herbicide A as described herein can form tautomers by hydrogen displacement which would not be formally covered by the general formulae (I), these tautomers are nevertheless encompassed by the definition of the compounds of the general formulae (I) according to the invention, unless a particular Tautomer is the subject of consideration. Thus, for example, many carbonyl compounds can be present both in the keto form and in the enol form, both forms being encompassed by the definition of the compound of the general formula (I).

[0066] The malonamide compounds of formula (I) have several centers of chirality and, as a consequence, are present as diastereomers.

[0067] Depending on the stereochemical orientation of the methoxy group (R or S), the malonamide compounds of formula

[0068] (I), I.R and I.S, are present as epimer / diastereomer mixtures in varying ratios.

[0069] Accordingly, compounds I.R and I.S, and respective epimer / diastereomer mixtures are particularly preferred as Herbicide A in the compositions and methods of the present invention.

[0070] In the context of the present invention, any ratio of the malonamide compound of formula (I) epimers in the respective epimer / diastereomer mixtures is contemplated and useful in the compositions and methods for selective weed control in grain crops. Non-limiting examples for ratios of the epimers in the respective epimer / diastereomer mixtures are 100: 0, 99.9:0.1 , 99.5:0.5, 99:1 , 98:2, 95:5, 90: 10, 80:20, 70:30, 60:40, 55:45, 50:50, 45:55, 40:60, 30:70, 20:80, 10:90, 5:95, 2:98, 1 :99, 0.5:99.5, 0.1 :99.9, 0:100. In some embodiments, the ratio of the epimers in the respective epimer / diastereomer mixtures is 95:5 or 50:50 + / - 10 % respectively.

[0071] In the context of the present invention, epimer / diastereomer mixtures I.R + I.S in varying ratios as listed above are particularly preferred components A in the compositions and methods according to the present invention; in very particularly preferred epimer / diastereomer mixtures, the percentage of the S-epimer in the epimer / diastereomer mixture is equal to or larger than the percentage of the R-epimer. For example, the S-epimer can be in the range of, 50- 100%, 60 to 100%, 70 to 100%, 80 to 100%, 90 to 100% or 95% + / - 5%, wherein the sum of the S- and the R-epimer is 100%.

[0072] The malonamide compounds of formula (I) are known from WO2021 / 170464.

[0073] Preferred malonamides of formula (I) (Herbicides A) in the methods and uses according to the invention are compounds of formula (I), wherein X1and X2are fluorine.

[0074] Further preferred malonamides of formula (I) (Herbicides A) in the methods and uses according to the invention are compounds of formula (I), wherein X1and X2are chlorine.

[0075] Further preferred malonamides of formula (I) (Herbicides A) in the methods and uses according to the invention are compounds of formula (I), wherein X1is fluorine and X2is chlorine.

[0076] Particular preferred malonamides of formula (I) (Herbicides A) in the methods and uses according to the invention are compounds of formula (I), wherein X1and X2are chlorine.

[0077] Preferred malonamides of formula (I) (Herbicides A) in the methods and uses according to the invention are compounds of formula (I), wherein R is selected from the group consisting of hydrogen, (Ci-CeJ-alkyl, and (Ca-CeJ-cycloal- kyl. In a particularly preferred embodiment, R is selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, cyclopropyl, and cyclobutyl. In the most preferred embodiment, R is selected from the group consisting of hydrogen, methyl and isopropyl.

[0078] Most preferred malonamides of formula (I) (Herbicides A) in the methods and uses according to the invention are compounds of formula (1.1) to (1.7) and combinations of the respective stereoisomers:

[0079]

[0080] The herbicidal malonamides of formula (I), Herbicide A, are suitable as herbicides for controlling resistant weeds.

[0081] They are suitable as such or as an appropriately formulated composition (agrochemical composition). In the methods and uses according to the present invention, the required application rate of Herbicide A or compositions comprising Herbicide A depends on the density of the undesired vegetation, in particular the resistant weeds, on the development stage of these plants, on the climatic conditions of the location where Herbicide A or a composition comprising Herbicide A is used and on the application method.

[0082] In general, the application rate of Herbicide A (total amount of Herbicide A) is from 1 g / ha to 300 g / ha, preferably from 2 g / ha to 200 g / ha, more preferably from 4 g / ha to 150 g / ha of active substance.

[0083] The recitation of ranges of values is a way of referring to each separate value within the range. This means that each individual value within the range is included in the specification as if it were individually recited. The range includes the endpoints, and any combination of values within the range can be used independently. When referring to numerical values or numerical ranges, integers and fractions within the range are included unless the context clearly indicates otherwise.

[0084] Exemplary for application rates, a range of 1 g / ha to 100 g / ha includes all application rates with values between 1 and 100, i.e. 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31,

[0085] 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62,

[0086] 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93,

[0087] 94, 95, 96, 97, 98, and 99, as well as values like 30.1, 35.4, 42.5, 48,8 and so on.

[0088] In one embodiment of the methods and uses according to present invention, Herbicide A or a composition comprising Herbicide A is applied pre-emergence of the crop with an application rate of Herbicide A of 1 g / ha to 300 g / ha, e.g. 2.5 g / ha to 250 g / ha.

[0089] In a particular embodiment of the method and uses according to present invention, the Herbicide A or a composition comprising Herbicide A is applied post-emergence of the crop with an application rate of Herbicide A of 1 g / ha to 200 g / ha, preferably with an application rate of 2 to 175 g / ha, more preferably with an application rate of 4 to 150 g / ha.

[0090] The above-mentioned application rates of Herbicide A indicate the amount of active agent without auxiliaries such as carrier material or surfactants.

[0091] If not stated otherwise, Herbicide A and compositions compring Herbicide A are suitable for application in any variety of crops as outlined herein. Examples of suitable crops are the following:

[0092] Allium cepa (onions), Allium sativum (garlic), Ananas comosus (pineapples), Arachis hypogaea [peanuts (groundnuts)], Asparagus officinalis (asparagus), Avena sativa (oat), Beta vulgaris spec, altissima (sugar beet), Beta vulgaris spec, rapa (turnips), Brassica napus var. napus (rapeseed, canola), Brassica napus van napobrassica (swedes), Brassica rapa var. silvestris (winter turnip rape), Brassica oleracea (cabbage), Brassica nigra (black mustard), Camellia sinensis (tea plants), Carthamus tinctorius (safflower), Carya illinoinensis (pecan trees), Citrus limon (lemons), Citrus sinensis (orange trees), Coffea arabica (Coffea canephora, Coffea liberica) (coffee plants), Cucumis sativus (cucumber), Cynodon dactylon (Bermudagrass), Daucus carotasubspec. sativa (carrot), Elaeis guineensis (oil palms), Fragaria vesca (strawberries), Glycine max (soybeans), Gossypium hirsutum (Gossypium arboreum, Gossy- pium herbaceum, Gossypium vitifolium), Helianthus annuus (sunflowers), Hevea brasiliensis (rubber plants), Hordeum vulgare (barley), Humulus lupulus (hops), Ipomoea batatas (sweet potatoes), Juglans regia (walnut trees), Lens culinaris (lentil), Linum usitatissimum (flax), Lycopersicon lycopersicum (tomatoes), Malus spec, (apple trees), Manihot esculenta (cassava), Medicago sativa [alfalfa (lucerne)], Musa spec, (banana plants), Nicotiana tabacum (N.rustica) (tobacco), Olea europaea (olive trees), Oryza sativa (rice), Phaseolus lunatus (limabeans), Phaseolus vulgaris (snapbeans, green beans, dry beans), Picea abies (Norway spruce), Pinus spec, (pine trees), Pistacia vera (pistachio), Pisum sativum (English peas), Prunus avium (cherry trees), Prunus persica (peach trees), Pyrus communis (pear trees), Prunus armeniaca (apricot), Prunus cerasus (sour cherry), Prunus dulcis (almond trees) and prunus domestica (plum trees), Ribes sylvestre (redcurrants), Ricinus communis (castor-oil plants), Saccharum offici- narum (sugar cane), Secale cereale (rye), Sinapis alba, Solanum tuberosum (Irish potatoes), Sorghum bicolor (s. vulgare) (sorghum), Theobroma cacao (cacao plants), Trifolium pratense (red clover), Triticum aestivum (wheat), Triti- cale (triticale), Triticum durum (durum wheat), Triticum turgidum (hard wheat), Triticum spelta (Spelt), Vicia faba (tick beans), Vitis vinifera (grapes), Zea mays (Indian corn, sweet corn, maize).

[0093] Preferred crops are Allium cepa, Allium sativum, Arachis hypogaea, Avena sativa, Beta vulgaris spec, altissima, Brassica napus van napus, Brassica oleracea, Cynodon dactylon, Daucus carota subspec. Sativa, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Pisum sativum, Saccharum officinarum, Secale cereale, Sola- num tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

[0094] In a preferred embodiment, the crop plant is selected from the group consisting of cereals, corn (maize), sunflower, rice, soybeans, peas, Vicia-beans, Phaseolus-beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables, in particular selected from the group consisting of wheat, barley, rye, triticale, oat, corn (maize), sunflower, rice, soybeans, peas, Vicia-beans, Phaseolus-beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables.

[0095] In an even more preferred embodiment, the crop plant is selected from the group consisting of cereals, corn (maize), sunflower, rice, soybeans, peas, beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables, in particular selected from the group consisting of wheat, barley, rye, triticale, oat, corn (maize), sunflower, rice, soybeans, peas, beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables.

[0096] In an especially preferred embodiment, the undesirable vegetation is controlled in cereals. In particular, the cereals are selected from the group consisting of wheat, barley, rye, rice, oat, sorghum, and triticale.

[0097] The methods and uses according to the invention are also suitable for controlling undesirable vegetation in crops which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

[0098] Herbicide A and compositions comprising Herbicide A are particularly suitable for controlling herbicide resistant weeds in non-crop applications and in fields of the following grain crops: cereals (small crops) such as wheat (Triticum aestivum) and wheat-like crops such as durum (T. durum), einkorn (T. monococcum), emmer (T. dicoccon) and spelt (T. spelta), rye {Secale cereale), triticale (Tritiosecale), barley (Hordeum vulgare),' sorghum (e.g. Sorghum bicolour),' rice (Oryza spp. such as Oryza sativa and Oryza glaberrima),' and turfgrasses.

[0099] Herbicide A and compositions compring Herbicide A are very particularly suitable for controlling herbicide resistant weeds in any variety of grain crops, preferably in fields of cereals, sorghum and rice.

[0100] According to a preferred embodiment of the invention, an effective amount of Herbicide A or a composition compring Herbicide A is applied to the crop cultivation area, where wheat, durum, einkorn, emmer, spelt, rye, triticale, or barley, preferably barley or wheat, was planted and wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype.

[0101] According to another preferred embodiment of the invention, an effective amount of Herbicide A or a composition compring Herbicide A are used for controlling herbcode resistant weeds in a crop cultivation area, where wheat, durum, einkorn, emmer, spelt, rye, triticale, or barley, preferably barley or wheat, was planted and where the undesirable vegetation comprises at least one herbicide resistant weed biotype.

[0102] For example, Herbicide A or a composition compring Herbicide A can effectively control herbicide-resistant grass weeds such as Alopecurus myosuroides (ALOMY), Apera spica-venti (APESV), Avena fatua (AVEFA), Echinochloa species (ECHSS), Phalaris species (PHASS), Poa annua (POAAN), Leptochloa species (LEFSS) or Lolium species (LOLSS), which have evolved resistance against ACCase-, ALS-, HPPD-, or Photosynthesis at PSII inhibiting herbicides, especially against ALS- or ACCase- inhibiting herbicides.

[0103] Another advantage of this invention is that Herbicide A can be used for controlling weed biotypes with target-site resistance but also weed biotypes with non-target site resistance. A particular advantage of the invention is that Herbicide A also provides effective control of weed biotypes having both target-site resistance and non-target-site resistance, such as resistant populations of Alopecurus myosuroides (ALOMY), Avena fatua (AVEFA), Echinochloa species (ECHSS), Leptochloa species (LEFSS) or Lolium rigidum (LOLRI). "Target-site resistance", as used herein, occurs by mutation within a gene coding for an herbicide target-site enzyme (limiting the herbicide binding) or by overproduction of the target enzyme (gene overexpression or amplification).

[0104] "Non-target-site resistance", as used herein, involves mechanisms that minimize the amount of active herbicide reaching the target site (e.g. reduced herbicide uptake or translocation, increased herbicide sequestration, or enhanced herbicide metabolism).

[0105] Effective weed control is defined as at least 70% weed suppression or eradication from the crop, or as at least 70% weed plant phytotoxicty, as determined 1-3 weeks after treatment.

[0106] Thus, resistant weeds are weeds, which are not controlled by the application of a herbicide used at the highest registered field rate, whereas the respective sensitive biotype is controlled at that use rate.

[0107] Here, "not controlled” means that, in a visual rating, the weed control (herbicidal effect) is < 60 % of weed suppression or eradication as determined 1-3 weeks after treatment; and "controlled” means that, in a visual rating, the weed control is > 70 % of weed suppression or eradication as determined 1-3 weeks after treatment.

[0108] Preferably, resistant weeds are weeds, which are not controlled (i.e. in a visual rating the weed control is < 60 % of weed suppression or eradication as determined 1-3 weeks after treatment) by the application of a herbicide used at the highest registered field rate.

[0109] Also preferably, herbicide resistant weeds are weeds, which are not controlled (i.e. in a visual rating the weed control is < 60 % of weed suppression or eradication as determined 1-3 weeks after treatment) by the application a herbicide used at the highest registered field rate, whereas the respective sensitive biotype is controlled (i.e. in a visual rating the weed control is > 70 % of weed suppression or eradication as determined 1-3 weeks after treatment) at that use rate.

[0110] In the context of the present invention, exemplary herbicide resistant weed species include, but are not limited to, biotypes resistant to herbicides selected from the group consisting of Acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1), acetolactate synthase (ALS) inhibitors (HRAC Group 2), inhibitors of photosynthesis at photosystem II (PS II) (HRAC Groups 5 and 6), photosystem I (PS I) inhibitors (HRAC Group 22), protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group 14), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group 27), phytoene desaturase (PDS) inhibitors (HRAC Group 12), lycopene cyclase inhibitors (HRAC Group 34), DOXP synthase inhibitors (HRAC Group 13), 5-enolpyruvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group 9), glutamine synthetase inhibitors (HRAC Group 10), Dihydropteroate (DHP) synthase inhibitors (HRAC Group 18), inhibitors of microtubuli assembly (HRAC Group 3), inhibitors of mitosis / microtubuli organization (HRAC Group 23), very long chain fatty acid (VLCFA) inhibitors (HRAC Group 15), inhibitors of cell wall synthesis (HRAC Group 29), uncoupler (membran disruption) (HRAC Group 24), synthetic auxins (HRAC Group 4), auxin transport inhibitors (HRAC Group 19), dihydroorotate dehydrogenase (DHODH) inhibitors (HRAC Group 28), solanesyl diphosphate synthase (SDS) inhibitors (HRAC Group 32), serine-threonine protein phosphatase inhibitors (HRAC Group 31), fatty acid thioesterase (FAT) inhibitors (HRAC Group 30), inhibitor of (HRAC Group 18), homogentisate solanesyltransferaseand (HST) inhibitors (HRAC Group 33), and herbicides with unknown mode of action (HRAC Group 0).

[0111] Preferably, the herbicide resistant weed species is selected from biotypes resistant to herbicides selected from the group consisting of Acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1), acetolactate synthase (ALS) inhibitors (HRAC Group 2), inhibitors of photosynthesis at photosystem II (PS II) (HRAC Groups 5 and 6), protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group 14), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group 27), phytoene desaturase (PDS) inhibitors (HRAC Group 12), 5-enolpyruvylshikimate-3- phosphate (EPSP) inhibitors (HRAC Group 9), inhibitors of microtubuli assembly (HRAC Group 3), very long chain fatty acid (VLCFA) inhibitors (HRAC Group 15), inhibitors of cell wall synthesis (HRAC Group 29), inhibitors of glutamine synthetase (HRAC Group 10), dihydroorotate dehydrogenase (DHODH) inhibitors (HRAC Group 28), fatty acid thioesterase (FAT) inhibitors (HRAC Group 30), and herbicides with unknown mode of action (HRAC Group 0).

[0112] More preferably, the herbicide resistant weed species is selected from biotypes resistant to herbicides selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1), acetolactate synthase (ALS) inhibitors (HRAC Group 2), inhibitors of photosynthesis at photosystem II (PS II) (HRAC Groups 5 and 6), 4- hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group 27), 5-enolpyruvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group 9), inhibitors of microtubuli assembly (HRAC Group 3), very long chain fatty acid (VLCFA) inhibitors (HRAC Group 15), inhibitors of cell wall synthesis (HRAC Group 29), inhibitors of glutamine synthetase (HRAC Group 10), and fatty acid thioesterase (FAT) inhibitors (HRAC Group 30).

[0113] Even more preferably, the herbicide resistant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1), acetolactate synthase (ALS) inhibitors (HRAC Group 2), inhibitors of photosynthesis at photosystem II (PS II) (HRAC Groups 5 and 6), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group 27), 5- enolpyruvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group 9), inhibitors of microtubuli assembly (HRAC Group 3), very long chain fatty acid (VLCFA) inhibitors (HRAC Group 15), and inhibitors of glutamine synthetase (HRAC Group 10), in particular from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1), acetolactate synthase (ALS) inhibitors (HRAC Group 2), inhibitors of photosynthesis at photosystem II (PS II) (HRAC Groups 5 and 6), and 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group 27).

[0114] In the context of the present invention, the herbicide resistant weed species is in particular selected from biotypes with resistance or tolerance to at least one herbicide selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1) and acetolactate synthase (ALS) inhibitors (HRAC Group 2).

[0115] In one embodiment, the herbicide resistant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1).

[0116] In another embodiment, the herbicide resistant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from acetolactate synthase (ALS) inhibitors (HRAC Group 2).

[0117] In the context of the present invention, the herbicide resistant weed is selected from the genera Abutilon, Aeschy- nomene, Alisma, Alopecurus, Alternanthera, Amaranthus, Ambrosia, Ammannia, Bacopa, Bidens, Bolboschoenus, Brachiaria, Calystegia, Capsella, Caperonia, Centaurea, Chenopodium, Cleome, Commelina, Convolvulus, Cynodon, Cyperus, Descurainia, Digitaria, Echinochloa, Eclipta, Eleocharis, Eleusine, Eriochloa, Erigeron, Euphorbia, Fimbristylis, Galium, Helianthus annuus, Heteranthera, Ipomoea, Ischaemum, Isolepis, Kochia, Leptochloa, Limnocharis, Lindernia, Lolium, Ludwigia, Marsilia, Matricaria, Melochia, Mollugo, Monochoria, Oryza sativa, Panicum, Papaver, Paspalum, Persicaria, Phalaris, Poa, Polygonum, Pontederia, Portulaca, Raphanus, Rottboellia, Sagittaria, Schoeno- plectiella, Schoenoplectus, Scirpoides, Scirpus, Sesbania, Setaria, Sida, Sinapis, Sisymbrium, Sphenoclea, Sorghum halepense, Stellaria, Thlaspi, Trichophorum, Typha, Urochloa and Xanthium.

[0118] In one embodiment, the herbicide resistant weed is a monocotyledonous weed species selected from the genera Ag- ropyron, Alopecurus, Alisma, Apera, Avena, Bolboschoenus, Brachiaria, Bromus, Commelina, Cynodon, Cyperus, Digitaria, Echinochloa, Eleocharis, Eleusine, Eriochloa, Fimbristylis, Heteranthera, Ischaemum, Isolepis, Leptochloa, Limnocharis, Lolium, Monochoria, Oryza sativa, Panicum, Paspalum, Phalaris, Poa, Pontederia, Rottboellia, Sagittaria, Schoenoplectiella, Schoenoplectus, Scirpoides, Scirpus, Setaria, Sorghum halepense, Trichophorum, Typha and Urochloa.

[0119] More preferably, the herbicide resistant weed is a monocotyledonous weed species selected from the genera Alopecurus, Apera, Avena, Cyperus, Digitaria, Echinochloa, Eleusine, Leptochloa, Lolium, Phalaris, Poa and Setaria. Most preferably, the herbicide resistant weed species is a monocotyledonous weed species selected from the genera Alopecurus and Avena,

[0120] In particular, the herbicide resistant weed is selected from the monocotyledonous weed species Alopecurus myosu- roides, Alopecurus aegualis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria de- cumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Bolboschoenus planiculmis, Cynodon dactylon, Cynodon transvaalensis, Cyperus compressus, Cyperus difformis, Cyperus ilia, Cyperus sp., Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa coIonum, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa formosensis, Echinochloa oryzoides, Echinochloa phyllogogon, Echinochloa sp., Echinochloa zelayensis, Eleusine indica, Fimbristylis guinguangularis, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflo- rum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Panicum capillare, Panicum dichotomiflorum, Phalaris bra- chystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Schoenoplectiella juncoides, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillate and Setaria viridis. Preferably, the herbicide resistant weed is selected from the monocotyledonous weed species Alopecurus myosu- roides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Digitaria insularis, Echinochloa colona, Echinochloa coIonum, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa formosen- sis, Echinochloa oryzoides, Echinochloa phyllogo-gon, Echinochloa sp., Echinochloa zelayensis, Eleusine indica, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillate and Setaria viridis.

[0121] More preferably, the herbicide resistant weed is selected from the monocotyledonous weed species Alopecurus myo- suroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Digitaria insularis, Echinochloa colona, Echinochloa coIonum, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa formosensis, Echinochloa oryzoides, Echinochloa phyllogogon, Echinochloa sp., Echinochloa zelayensis, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillate and Setaria viridis.

[0122] Most preferably, the herbicide resistant weed is selected from the monocotyledonous weed species Alopecurus myo- suroides and Avena fatua.

[0123] In another embodiment, the herbicide resistant weed is a dicotyledonous weed species selected from the genera Abutilon, Aeschynomene, Alternanthera, Ambrosia, Ammannia, Amaranthus, Anthemis, Bacopa, Bidens, Calystegia, Capsella, Caperonia, Centaurea, Chenopodium, Cleome, Commelina, Convolvulus, Conyza, Descurainia, Des- modium, Eclipta, Erigeron, Euphorbia, Galium, Helianthus annuus, Ipomoea, Kochia, Lindernia, Limnocharis, Lud- wigia, Matricaria, Melochia, Mollugo, Papaver, Persicaria, Polygonum, Pontederia, Portulaca, Raphanus, Sesbania, Sida, Sinapis, Sisymbrium, Sphenoclea, Stellaria, Thlaspi, Tripleurospermum, Veronica and Xanthium.

[0124] In particular, the herbicide resistant weed is selected from the dicotyledonous weed species Abutilon theophrasti, Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmed, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisifolia, Ammannia auriculata, Ammannia baccifera, Ammannia multiflora, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cy- anus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Commelina benghalensis, Conyza bonariensis, Conyza canadensis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Kochia scoparia, Limnocharis flava, Ludwigia decurrens, Ludwigia octovalvis, Ludwigia prostrata, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver rhoeas, Pontederia korsakowii, Pontederia vaginalis, Potamogeton distinctus, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium orientate, Stellaria media, Sphenoclea zeylanic, Thlaspi arvense, Tripleurospermum inodorum and Veronica persica. In another embodiment, the methods and uses of this invention are suitable for controlling ACCase-resistant mono- cotyledonous weeds selected from the genera Alopecurus, Apera, Avena, Digitaria, Echinochloa, Eleusine, Lepto- chloa, Lolium, Phalaris, Poa and Setaria.

[0125] More preferably, ACCase-resistant monocotyledonous weeds are selected from the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium.

[0126] More specifically, ACCase-resistant monocotyledonous weed species are selected from Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Digitaria ciliaris, Digitaria insularis, Digitaria is- chaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Echinochloa sp., Eleusine indica, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivi- alis, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillata and Setaria viridis.

[0127] More preferably, ACCase-resistant monocotyledonous weed species are selected from Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis.

[0128] In particular, ACCase-resistant monocotyledonous weed species are selected from Alopecurus myosuroides and Avena fatua.

[0129] In another embodiment, the methods and uses of this invention are suitable for controlling ALS-resistant monocotyledonous weeds selected from the genera Alopecurus, Apera, Avena, Cyperus, Digitaria, Echinochloa, Eleusine, Leptochloa, Lolium, Phalaris, Poa and Setaria.

[0130] Preferably, ALS-resistant monocotyledonous weeds are selected from the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium.

[0131] More specifically, ALS-resistant monocotyledonous weed species are selcted from Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Digitaria ciliaris, Digitaria insularis, Digitaria ischae- mum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Echinochloa sp., Eleusine indica, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillata and Setaria viridis. More preferably, ALS-resistant monocotyledonous weed species are selected from Alopecurus myosuroides, Alo- pecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis.

[0132] In particular, ALS-resistant monocotyledonous weed species are selected from Alopecurus myosuroides and Avena fatua.

[0133] In another embodiment, the methods and uses of this invention are suitable for controlling multiple resistant monocotyledonous weeds selected from the genera Alopecurus, Apera, Avena, Cyperus, Digitaria, Echinochloa, Eleusine, Leptochloa, Lolium, Phalaris, Poa and Setaria.

[0134] More preferably, multiple resistant weeds are selected from the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium.

[0135] More specifically, multiple resistant monocotyledonous weed species are selcted from Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Digitaria ciliaris, Digitaria insularis, Digitaria ischae- mum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Echinochloa sp., Eleusine indica, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillata and Setaria viridis.

[0136] More preferably, multiple resistant monocotyledonous weed species are selected from Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis.

[0137] Most preferably, multiple resistant monocotyledonous weed species are selected from Alopecurus myosuroides and Avena fatua.

[0138] One particular embodiment of the present invention (E1) is directed to a method for controlling undesirable vegetation, which comprises applying to the vegetation or the locus thereof or to the soil or water a herbicidal ly effective amount of a Herbicide A, wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype selected from monocotyledonous weeds of the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium, preferably from the species Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, and Lolium x hybridum, and most preferably from the species Alopecurus myosuroides and Avena fatua. One particular embodiment of the present invention (E2) is directed to a method for controlling undesirable vegetation, which comprises applying to the vegetation or the locus thereof or to the soil or water a herbicidal ly effective amount of Compound 1.1, wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype selected from monocotyledonous weeds of the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium, preferably from the species Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, and Lolium x hybridum, and most preferably from the species Alopecurus myosuroides and Avena fatua.

[0139] One particular embodiment of the present invention (E3) is directed to a method for controlling undesirable vegetation, which comprises applying to the vegetation or the locus thereof or to the soil or water a herbicidal ly effective amount of a Compound 1.2, wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype selected from monocotyledonous weeds of the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium, preferably from the species Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, and Lolium x hybridum, and most preferably from the species Alopecurus myosuroides and Avena fatua.

[0140] One particular embodiment of the present invention (E4) is directed to a method for controlling undesirable vegetation, which comprises applying to the vegetation or the locus thereof or to the soil or water a herbicidal ly effective amount of Compound 1.3, wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype selected from monocotyledonous weeds of the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium, preferably from the species Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, and Lolium x hybridum, and most preferably from the species Alopecurus myosuroides and Avena fatua.

[0141] One particular embodiment of the present invention (E5) is directed to a method for controlling undesirable vegetation, which comprises applying to the vegetation or the locus thereof or to the soil or water a herbicidal ly effective amount of Compound 1.4, wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype selected from monocotyledonous weeds of the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium, preferably from the species Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, and Lolium x hybridum, and most preferably from the species Alopecurus myosuroides and Avena fatua.

[0142] One particular embodiment of the present invention (E6) is directed to a method for controlling undesirable vegetation, which comprises applying to the vegetation or the locus thereof or to the soil or water a herbicidal ly effective amount of Compound 1.5, wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype selected from monocotyledonous weeds of the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium, preferably from the species Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, and Lolium x hybridum, and most preferably from the species Alopecurus myosuroides and Avena fatua.

[0143] One particular embodiment of the present invention (E7) is directed to a method for controlling undesirable vegetation, which comprises applying to the vegetation or the locus thereof or to the soil or water a herbicidal ly effective amount of Compound 1.6, wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype selected from monocotyledonous weeds of the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium, preferably from the species Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, and Lolium x hybridum, and most preferably from the species Alopecurus myosuroides and Avena fatua.

[0144] One particular embodiment of the present invention (E8) is directed to a method for controlling undesirable vegetation, which comprises applying to the vegetation or the locus thereof or to the soil or water a herbicidal ly effective amount of Compound 1.7, wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype selected from monocotyledonous weeds of the genera Alopecurus, Avena, Echinochloa, Leptochloa and Lolium, preferably from the species Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Echinochloa crus-galli, Echinochloa sp., Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, and Lolium x hybridum, and most preferably from the species Alopecurus myosuroides and Avena fatua.

[0145] Particularly preferred embodiments of the present invention are Embodiments (E9) to (E16), which differ from the respective Embodiments (E1) to (E8), in that the herbicidal malonamide is applied at an application rate from 4 to 150 g / ha, e.g. at an application rate of 4, 5, 6, 7, 8, 9, 10, 12, 14, 16, 18, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80, 90. 100, 110, 120, 130, 140 or 150 g / ha.

[0146] Further particularly preferred embodiments of the present invention are Embodiments (E17) to (E24), which differ from the respective Embodiments (E9) to (E16), in that the herbicidal malonamide is applied after the undesirable vegetation has emerged and has developed up to BBCH stage 14-15.

[0147] Further particularly preferred embodiments of the present invention are Embodiments (E25) to (E32), which differ from the respective Embodiments (E17) to (E24), in that the herbicidal malonamide is applied post-emergence of the crop.

[0148] In one embodiment of the methods and uses according to the invention, the Herbicide A is applied alone, i.e. the Herbicide A is the only herbicidally active ingredient.

[0149] In another embodiment, the Herbicide A is applied in combination with at least one Herbicide B, which is different from Herbicide A.

[0150] In addition to the Herbicide A and the optional Herbicide B, the use or method of this invention may further comprise applying at least one Safener C.

[0151] Therefore, in one embodiment, the use or method of the present invention comprises applying Herbicide A, at least one Safener C and optionally at least one Herbicide B. In another embodiment, the use or method of the present invention comprises applying Herbicide A, at least one Herbicide B and at least one Safener C.

[0152] In another embodiment of the methods or uses of this invention, a composition comprising the Herbicide A is applied. In a preferred embodiment of the methods or uses of this invention, a composition comprising the Herbicide A and at least one Herbicide B is applied. In yet another embodiment of the methods or uses of this invention, a composition comprising the Herbicide A and at least one Safener C is applied. In still another embodiment of the methods or uses of this invention, a composition comprising the Herbicide A, at least one Herbicide B and at least one Safener C is applied.

[0153] The Herbicides B and Safeners C are known herbicides and safeners, see, for example, The Pesticide Manual, British Crop Protection Council, 16thedition, 2012; The Compendium of Pesticide Common Names (http: / / www.alan- wood.net / pesticides / ); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CAS No. 52836-31-4] is also referred to as R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also referred to as AD-67 and MON 4660.

[0154] In yet another embodiment, these compositions may further comprise one or more auxiliaries customary in crop protection (as defined herein).

[0155] In the methods and uses of the invention, the weight ratio of Herbicide A to Herbicide B is generally in the range of from 1 :1000 to 1000:1, preferably in the range of from 1 :500 to 500:1, in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1, wherein each Herbicide B being an ester or a salt of an acid is calculated as the acid.

[0156] In the methods and uses of the invention, the weight ratio of Herbicide A to Safener C is generally in the range of from 1 :1000 to 1000:1, preferably in the range of from 1 :500 to 500:1, in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1, wherein each Safener C being an ester or a salt of an acid is calculated as the acid.

[0157] In the methods and uses of the invention, the weight ratio of Herbicide B to Safener C is generally in the range of from 1 :1000 to 1000:1, preferably in the range of from 1 :500 to 500:1, in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1, wherein each Herbicide B and Safener C being an ester or a salt of an acid is calculated as the acid. In the methods and uses of the invention, the weight ratio of the combination of Herbicides A and B to the Safener C is preferably in the range of from 1 :500 to 500:1, in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1, wherein each Herbicide B and Safener C being an ester or a salt of an acid is calculated as the acid.

[0158] The herbicidal compositions as defined herein are suitable as herbicides as such or as appropriately formulated agrochemical compositions. As used herein, the term "agrochemical composition” refers to a composition further comprising one or more auxiliaries customary in crop protection.

[0159] Thus, the agrochemical composition comprises the Herbicide A, optionally at least one Herbicide B, optionally at least one Safener C and one or more auxiliaries customary in crop protection.

[0160] The Herbicide A, optionally at least one Herbicide B and optionally at least one Safener C can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for agrochemical composition types are suspensions (e.g. SC, CD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EC, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further agrochemical compositions types are defined in the "Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6thEd. May 2008, CropLife International.

[0161] The agrochemical compositions can be prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0162] The term "auxiliaries customary in crop protection" includes but is not limited to solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

[0163] Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof. Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

[0164] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0165] Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

[0166] Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

[0167] Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

[0168] Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[0169] Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0170] Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazoli- nones.

[0171] Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

[0172] Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

[0173] Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

[0174] Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0175] The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

[0176] Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the Herbicide A, optionally at least one Herbicide B and optionally at least one Safener C (or the composition comprising the Herbicide A, optionally at least one Herbicide B and optionally at least one Safener C) used or applied in this invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.

[0177] According to one embodiment, either individual components of the agrochemical composition or partially premixed components, e. g. agrochemical components comprising Herbicide A, optionally at least one Herbicide B and optionally at least one Safener C may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.

[0178] In another embodiment, individual components of the agrochemical composition such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate. In another embodiment, either individual components of the agrochemical composition or partially premixed components, e. g. components comprising Herbicide A, optionally at least one Herbicide B and optionally at least one Saf- ener C can be applied jointly (e.g. after tank mixing) or consecutively.

[0179] Accordingly, the agrochemical composition may be provided in the form of a single package formulation comprising Herbicide A, optionally at least one Herbicide B and optionally at least one Safener C together with liquid and / or solid carriers, and, if desired, one or more surfactants and, if desired, one or more further auxiliaries customary in crop protection. The formulation may be provided in the form of a two-package formulation, wherein one package comprises a formulation of Herbicide A while the other package comprises a formulation comprising at least one Herbicide B and / or Safener C, and wherein both formulations comprise at least one carrier material, if desired, one or more surfactants and, if desired, one or more further auxiliaries customary in crop protection. The formulation may also be provided in the form of a two-package formulation, wherein one package comprises a formulation of Herbicide A and optionally the Safener C, while the other package comprises a formulation of the at least one Herbicide B, and wherein both formulations comprise at least one carrier material, if desired, one or more surfactants and, if desired, one or more further auxiliaries customary in crop protection. In the case of two package formulations, the two formulations are preferably mixed prior to application. Preferably, the mixing is performed as a tank mix, i.e. the formulations are mixed immediately prior or upon dilution with water.

[0180] The user applies the agrochemical composition used or applied in this invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and / or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

[0181] The compositions as defined herein can be applied pre- or post-emergence or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying seed, pretreated with a composition as defined herein, of a crop plant. If the Herbicide A and, if appropriate, the Herbicide B are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

[0182] Moreover, it may be advantageous to apply the compositions as defined herein on their own or jointly in combination with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth. Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added. When employed in plant protection, the amounts of active substances applied without formulation auxiliaries, are, depending on the kind of effect desired, 0.0001 to 10 kg per hectare (kg / ha), preferably 0.001 to 3 kg / ha, more preferably from 0.001 to 2.5 kg / ha, even more preferably from 0.001 to 2 kg / ha, especially preferably from 0.005 to 2 kg / ha, in particular from 0.05 to 0.9 kg / ha and most preferably from 0.1 to 0.8 kg / ha.

[0183] In the methods and uses of this invention, the application rate of the Herbicide B (in case of salts calculated as the acid) is generally from 0.0005 kg / ha to 10 kg / ha, preferably from 0.005 kg / ha to 5 kg / ha and more preferably from 0.001 kg / ha to 2.5 kg / ha.

[0184] In the methods and uses of this invention, the application rate of the Safener C (in case of salts calculated as the acid) is generally from 0.0005 kg / ha to 2.5 kg / ha, preferably from 0.005 kg / ha to 2 kg / ha and more preferably from 0.01 kg / ha to 1.5 kg / ha.

[0185] In the methods and uses of the invention, the Herbicide A and, if present, the Herbicide B and / or the Safener C can be applied jointly or separately.

[0186] In the methods and uses of the invention, the Herbicide A and, if present, the Herbicide B and / or the Safener C can be applied simultaneously or in succession.

[0187] Preferably, the Herbicide A and, if present, the Herbicide B and / or the Safener C are applied simultaneously to the undesirable vegetation. In another embodiment, the Herbicide A and, if present, the Herbicide B and / or the Safener C are provided as herbicidal composition as defined herein (e.g. a tank mixture containing the Herbicide A and, if present, the Herbicide B and / or the Safener C) being applied to the undesirable vegetation. Thus, in some embodiments of the method of this invention, the herbicidal composition as defined herein is applied to the undesirable vegetation or the locus thereof with or applied to the soil or water to prevent the emergence or growth of the undesirable vegetation.

[0188] In case of separate or successive application, the order of the application of the Herbicide A and, if present, the Herbicide B and / or the Safener C is of minor importance. It is only necessary that the Herbicide A and, if present, the Herbicide B and / or the Safener C are applied in a time frame that allows simultaneous action of the active ingredients on the plants to be controlled and / or safened, preferably within a time frame of at most 14 days, in particular at most 7 days.

[0189] In the methods and uses of the invention, the Herbicide A and, if present, the Herbicide B and / or the Safener C (or the composition as defined herein) can be applied pre-emergence (i.e. before the emergence of undesirable vegetation) or post-emergence (i.e., during and / or after emergence of the undesirable vegetation). In one embodiment, the Herbicide A and, if present, the Herbicide B and / or the Safener C (or the composition as defined herein) are / is applied before the emergence of the undesirable vegetation (pre-emergence).

[0190] In another embodiment, the Herbicide A and, if present, the Herbicide B and / or the Safener C (or the composition as defined herein) are / is applied before or during the emergence of the undesirable vegetation (pre-emergence or early- post emergence).

[0191] In another embodiment, the Herbicide A and, if present, the Herbicide B and / or the Safener C (or the composition as defined herein) are / is applied after emergence of the undesirable vegetation.

[0192] In case of post-emergence treatment, the Herbicide A and, if present, the Herbicide B and / or the Safener C (or the composition as defined herein) are / is preferably applied after the undesirable vegetation has emerged and has developed up to BBCH stage 14-15.

[0193] The following examples serve to illustrate the invention.

[0194] Examples

[0195] The herbicidal activity of Herbicides A on resistant weed biotypes was tested in comparison to commercial herbicides at the highest respective registered application rate (x) and the double rate (2x).

[0196] The commercial herbicides were selected from the group of

[0197] • ACCase inhibitors: pinoxaden, quizalofop, clethodim, clodinafop (HRAC Group 1);

[0198] • ALS-inhibitors: mesosulfurone + iodosulfurone, pyroxsulam (HRAC Group 2);

[0199] • HPPD inhibitors: pyrasulfotole (HRAC Groups 5 and 6); and

[0200] • Photosynthesis inhibitors: bromoxynil (HRAC Group 27).

[0201] In addition, the herbicidal activity of Herbicides A on resistant weed biotypes was tested in comparison to a structurally highly similar herbicidal compound of formula 11.1 (IUPAC: methyl (4S)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3- oxo-propanoyl]amino]pentanoate, CAS: 2699953-66-5), disclosed in WO2021 / 170464.

[0202] The following greenhouse experiments were conducted: The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species. Blackgrass (ALOMY) biotypes (BT 01087, BT 12199, BT 12200, BT 12201 , BT 12203, BT 12204, BT 12217, BT 12206, BT 12207, BT 12208, BT

[0203] 12209, BT 01580, BT 01619, BT 01729, BT 01726, BT 01397, BT 17050, BT 17056, BT 17058, BT 17059, BT

[0204] 16448, BT 16449, BT 16450, BT 16451 , BT 16454) ) and wild oat (AVEFA) biotypes (BT 21755, BT 21757, BT

[0205] 21758, BT 21761 , BT 21763, BT 21773, BT 21776, BT 21777, BT 21779, BT 21780, BT 03241 , BT 21771, BT

[0206] 21772) with varying degrees of resistance towards a range of modes of action according to the HRAC (Herbicide Resistance Action Committee) classification on mode of action 2022 (see e.g https: / / hracglobal.com / tools / hrac-mode-of- action-classification-2022-map) were tested alongside non-resistant biotypes (ALOMY: BT 01087; AVEFA: BT 03558), see Tables 1 below. In case of a known resistance within the biotype, the HRAC group is provided (see Table 1.5).

[0207] For the post-emergent treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

[0208] Depending on the species, the plants were kept at 10-25°C or 20-35°C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

[0209] • Herbicides A were formulated as an emulsion concentrate (EC with a loading of 100 g / L) with an active ingredient concentration of 5% and additional 0.25% of the adjuvant DASH.

[0210] • Compound 11.1 was formulated as an emulsion concentrate (EC with a loading of 100 g / L) with an active ingredient concentration of 5% and additional 0.25% of the adjuvant DASH.

[0211] • Pinoxaden was used as a commercial emulsion concentrate (EC with 50 g / L loading), which is commercialized under the trademark Axial® and registered up to an application rate of 60 g / ha, plus the adjuvant ADIGOR® in a concentration of 0.27%.

[0212] • Guizalofop was used as a commercial emulsion concentrate (EC with 106 g / L loading), which is commercialized under the trademark Assure® II and registered up to an application rate of 48 g / ha, plus the adjuvant DASH® in a concentration of 1 %.

[0213] • Clethodim was used as a commercial emulsion concentrate (EC with 240 g / L loading), which is commercialized under the trademark SELECT®240 EC and registered up to an application rate of 45 g / ha, plus the adjuvant DASH® in a concentration of 0.25%.

[0214] • Meso- and iodosulfuron were used as commercial oil dispersion (CD with 12 g / L loading), which is commercialized under the trademark Atlantis® and registered up to an application rate of 18 g / ha, plus the adjuvant Mero®, an emulsion concentrate (EC with 810 g / L loading) with 1000 g / ha.

[0215] • Pyroxsulam was used as commercial water dispersible granules (WG with 21 .5% loading), which is registered up to an application rate of 15 g / ha, plus the adjuvant MSO in a concentration of 0.5%. Evaluation of the herbicidal activity was carried out using a scale from 0 to 100. 100 means complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.

[0216] Example 1 :

[0217] Table 1.1 : Herbicidal activity of Herbicides (A) in comparison to Axial® and compound 11.1 , applied post-emergence on blackgrass (ALOMY) biotypes with growth stage BBCH 11-12, assessed 20 days after treatment:

[0218] Table 1.2: Herbicidal activity of Herbicides (A) in comparison to compound 11.1 applied post-emergence on blackgrass (ALOMY) biotypes on BBCH growth stage 11 , assessed 20 days after treatment:

[0219] Table 1.3: Herbicidal activity of Herbicides (A) in comparison with Axial®, Atlantis® and compound 11.1 , applied postemergence on blackgrass (ALOMY) biotypes with BBCH growth stage 11 , assessed 21 days after treatment:

[0220] Table 1.4: Herbicidal activity of Herbicides (A) in comparison with Axial® and Atlantis®, applied post-emergence on blackgrass (ALOMY) biotypes with BBCH growth stage 11 , assessed 20 days after treatment:

[0221] Table 1.5: Herbicidal activity of Herbicides (A) in comparison to Pyroxsulam, Clethodim, Quizalofop and compound 11.1 , applied post-emergence on wild oat (AVEFA) biotypes with BBCH growth stage 11 , assessed 20 days after treatment:

[0222] Table 1.6: Herbicidal activity of Herbicides (A) in comparison to Quizalofop, applied post-emergence on wild oat (AVEFA) biotypes with BBCH growth stage 11 , assessed 20 days after treatment:

[0223] Table 1.7: Herbicidal activity of Herbicides (A) in comparison to Pinoxaden, Quizalofop, and Clethodim, applied postemergence on wild oat (AVEFA) biotypes with BBCH growth stage 11 , assessed 20 days after treatment:

[0224] The following field testings were conducted:

[0225] On field test sites, natural weed infestation or seeded weeds were treated post-emergence of the weeds.

[0226] For the post emergence treatment, the weedy plants were treated as indicated below. The herbicidal compositions were, together with the adjuvant(s) as indicated, suspended or emulsified in water as distribution medium (200 l / ha unless indicated otherwise) and sprayed with commercial flat fan nozzles.

[0227] In the following experiments, the herbicidal activity for the individual herbicidal compositions was assessed the indicated days after treatment (DAT). The assessments for the damage on undesired weeds caused by the composition was carried out using a scale from 0 to 100%, compared to the untreated control plants. Here, 0 means no damage and 100 means complete destruction of the plants.

[0228] Example 2:

[0229] Table 2.1 : Herbicidal activity of Herbicides (A) in comparison to a mixture of Axial®XL and Infinity®, applied postemergence on wild oat (AVEFA) biotypes with BBCH growth stage 11, assessed 16 days after treatment: Market Standard:

[0230] Axial®XL: Pinoxaden as a 50 g / L EC formulation with Cloquintocet-mexyl as 12.5 g / L (safener).

[0231] Infinity®: 247.5 g / L EC formulation, with Pyrasulfotole (37.5 g / L) and Bromoxynil heptanoate and octanoate (210 g / L total).

[0232] Table 2.2: Herbicidal activity of Herbicides (A) in comparison to a mixture of Axial®XL and Infinity®, applied postemergence on wild oat (AVEFA) biotypes with BBCH growth stage 11, assessed 28 days after treatment: Market Standard:

[0233] Axial®XL: Pinoxaden as a 50 g / L EC formulation with Cloquintocet-mexyl as 12.5 g / L (safener)

[0234] Infinity®: Pyrasulfotole 37.5 g / L, Bromoxynil heptanoate and octanoate as 105 g / L each as 247.5 g / L EC formulation

[0235] Table 2.3: Herbicidal activity of Herbicides (A) in comparison to Axial®XL, Horizon®NG and Simplicity™ GoDRI™, applied post-emergence on wild oat (AVEFA) biotypes with 3-4 leaf stage, assessed 41 days after treatment: Axial®XL: Pinoxaden as a 50 g / L EC formulation with Cloquintocet-mexyl as 12.5 g / L (safener) Simplicity™ GoDRI™: Pyroxsulam as a 21.5% WG formulation with Agral®90 0.25% as adjuvant Horizon®NG: Clodinafop-propargyl 50 g / L, EC formulation. Table 2.4: Herbicidal activity of Herbicides (A) in comparison to Axial®XL, Horizon®NG and Simplicity™ GoDRI™, applied post-emergence on wild oat (AVEFA) biotypes with 3-4 leaf stage, assessed 28 days after treatment:

[0236] Axial®XL: Pinoxaden as a 50 g / L EC formulation with Cloquintocet-mexyl as 12.5 g / L (safener)

[0237] Simplicity™ GoDRI™: Pyroxasulam as a 21.5% WG formulation, with Agral®90 0.25% as adjuvant Horizon®NG: Clodinafop-propargyl 50 g / L, EC formulation.

Claims

Claims1. Use of a herbicidal malonamide (Herbicide A), selected from a compound of formula (I)whereinX1is fluorine or chlorine,X2is fluorine or chlorine,R is hydrogen, (Ci-Ce)-alkyl or (Cs-CeJ-cycloalkyl, or their agriculturally acceptable salts, stereoisomers and tautomers, for controlling herbicide resistant weed biotypes.

2. A method for controlling undesirable vegetation, which comprises applying to the vegetation or the locus thereof or to the soil or water a herbicidally effective amount of a herbicidal malonamide (Herbicide A), selected from a compound of formula (I)whereinX1is fluorine or chlorine, X2is fluorine or chlorine, R is hydrogen, (Ci-Ce)-alkyl or (Cs-CeJ-cycloalkyl, or their agriculturally acceptable salts, stereoisomers and tautomers, and wherein the undesirable vegetation comprises at least one herbicide resistant weed biotype.

3. The use according to claim 1 or the method according to claim 2, wherein the herbicide resistant weed biotype is a biotype with resistance or tolerance to at least one herbicide selected from the group consisting of Acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1), acetolactate synthase (ALS) inhibitors (HRAC Group 2), inhibitors of photosynthesis at photosystem II (PS II) (HRAC Groups 5 and 6), protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group 14), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group 27), phytoene desaturase (PDS) inhibitors (HRAC Group 12), 5-enolpyruvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group 9), inhibitors of microtubuli assembly (HRAC Group 3), very long chain fatty acid (VLCFA) inhibitors (HRAC Group 15), inhibitors of cell wall synthesis (HRAC Group 29), inhibitors of glutamine synthetase (HRAC Group 10), dihydroorotate dehydrogenase (DHODH) inhibitors (HRAC Group 28), fatty acid thioesterase (FAT) inhibitors (HRAC Group 30), and herbicides with unknown mode of action (HRAC Group 0).

4. The use according to claim 1 or the method according to claim 2, wherein the herbicide resistant weed biotype is a biotype with resistance or tolerance to at least one herbicide selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1), acetolactate synthase (ALS) inhibitors (HRAC Group 2), inhibitors of photosynthesis at photosystem II (PS II) (HRAC Groups 5 and 6), 4-hydroxyphenyl-pyruvate- dioxygenase (HPPD) inhibitors (HRAC Group 27), 5-enolpyruvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group 9), inhibitors of microtubuli assembly (HRAC Group 3), very long chain fatty acid (VLCFA) inhibitors (HRAC Group 15), and inhibitors of glutamine synthetase (HRAC Group 10).

5. The use according to claim 1 or the method according to claim 2, wherein the herbicide resistant weed biotype is a biotype with resistance or tolerance to at least one herbicide selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1), acetolactate synthase (ALS) inhibitors (HRAC Group 2), inhibitors of photosynthesis at photosystem II (PS II) (HRAC Groups 5 and 6), and 4-hydroxyphenyl-py- ruvate-dioxygenase (HPPD) inhibitors (HRAC Group 27).

6. The use according to claim 1 or the method according to claim 2, wherein the herbicide resistant weed biotype is a biotype with resistance or tolerance to at least one herbicide selected from acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group 1) and acetolactate synthase (ALS) inhibitors (HRAC Group 2).

7. The use according to any one of claims 1 and 3 to 6 or the method according to any one of claims 2 to 6, wherein the herbicide resistant weed biotype is selected from the genera Abutilon, Aeschynomene, Alisma, Alopecurus, Alternanthera, Amaranthus, Ambrosia, Amman-nia, Bacopa, Bidens, Bolboschoenus, Brachiaria, Calystegia, Capsella, Caperonia, Centaurea, Chenopodium, Cleome, Commelina, Convolvulus, Cynodon, Cyperus, Descurainia, Digitaria, Echinochloa, Eclipta, Eleocharis, Eleusine, Eriochloa, Erigeron, Euphorbia, Fimbristylis, Galium, Helianthus annuus, Heteranthera, Ipomoea, Ischaemum, Isolepis, Kochia, Leptochloa, Limno-charis, Lindernia, Lolium, Ludwigia, Marsilia, Matricaria, Melochia, Mollugo, Monochoria, Oryza sativa, Panicum, Papaver, Paspalum, Persicaria, Phalaris, Poa, Polygonum, Pontederia, Portu-laca, Raphanus, Rottboellia, Sagittaria, Schoenoplectiella, Schoenoplectus, Scirpoides, Scirpus, Sesbania, Setaria, Sida, Sinapis, Sisymbrium, Sphenoclea, Sorghum halepense, Stellaria, Thlaspi, Trichophorum, Typha, Urochloa and Xanthium.

8. The use according to any one of claims 1 and 3 to 6 or the method according to any one of claims 2 to 6, wherein the herbicide resistant weed biotype is a monocotyledonous weed biotype selected from the genera Alopecurus, Apera, Avena, Cyperus, Digitaria, Echinochloa, Eleusine, Leptochloa, Lolium, Phalaris, Poa and Setaria.

9. The use according to any one of claims 1 and 3 to 6 or the method according to any one of claims 2 to 6, wherein the herbicide resistant weed biotype is a monocotyledonous weed biotype selected from the group consisting of Alopecurus myosuroides and Avena fatua.

10. The use according to any one of claims 1 and 3 to 9 or the method according to any one of claims 2 to 9, wherein the undesirable vegetation is controlled in crop plants selected from wheat, barley, durum, rye, triticale, oat, corn (maize), sunflower, rice, soybeans, peas, Vicia-beans, Phaseolus-beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables.

11. The use according to any one of claims 1 and 3 to 10 or the method according to any one of claims 2 to 10, whereinX1and X2are chlorine.

12. The use according to any one of claims 1 and 3 to 11 or the method according to any one of claims 2 to 11, whereinR is hydrogen, methyl, ethyl, isopropyl, or cyclobutyl.

13. The use according to any one of claims 1 and 3 to 12 or the method according to any one of claims 2 to 12, wherein the herbicidal malonamide (Herbicide A) is applied with an application rate of 4 to 150 g / ha.

14. The use according to any one of claims 1 and 3 to 13 or the method according to any one of claims 2 to 13 wherein the Herbicide A and, if present, the Herbicide B and / or the Safener C are / is applied after emergence of the undesirable vegetation.

15. The use according to any one of claims 1 and 3 to 14 or the method according to any one of claims 2 to 14 wherein the Herbicide A and, if present, the Herbicide B and / or the Safener C are / is applied after emergence of the undesirable vegetation up to BBCH growth stage 32.

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