EA042560B1 - HERBICIDE MIXTURES - Google Patents

Description

The present invention relates to a herbicidal mixture containing i) 2-[(2,4-dichlorophenyl)methyl]4,4-dimethyl-3-isoxazolidinone and ii) cinmethylin, as well as herbicidal compositions containing these mixtures. In addition, the present invention relates to a process for preparing said herbicidal mixtures and formulations containing said mixtures. Further, the present invention relates to the use of these mixtures and compositions in the field of agriculture for the control of harmful plants.

2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone is already known as a selective herbicide from WO 2012/148689. Mixtures with this herbicide are known from WO 2015/127259.

In Wo 2017/009095, Wo 2017/009124, Wo 2017/009137, Wo 2017/009138, Wo 2017/009054, Wo 2017/009056, Wo 2017/009139, Wo 2017/009140, Wo 2017/009092, Wo 2017/009090 , WO 2017/009134, WO 2017/009142, WO 2017/009143, WO 2017/009143 and WO 2017/009144 describe herbicidal mixtures containing cinmethylin.

Despite the good performance of 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone as a single active ingredient and in already known mixtures, there is still a need to improve the application profile of this active ingredient. The reasons for this are many, such as improved efficiency in certain applications, improved crop compatibility, better responses to new production technologies in individual crops, and/or more herbicide-tolerant plants.

The possibility of improving the application profile of the herbicide may consist in the combination of the active ingredient with one or more other suitable active ingredients. Of course, with the combined use of several active substances, phenomena of chemical, physical and biological incompatibility often occur, for example, insufficient stability in the composition, degradation of the active substance or incompatibility of the active substances. On the contrary, combinations of active ingredients with a favorable action profile, high stability and maximally enhanced synergistic action are desirable, which makes it possible to reduce application rates compared to a single single exposure of the combined active ingredients. It is also desirably possible to use active ingredients which improve the compatibility of cultivated plants in general and/or in specific production techniques. These include, for example, reducing the sowing depth, which cannot often be applied for reasons of compatibility of cultivated plants. As a result, rapid germination of cultivated plants can be obtained, the risk of diseases associated with long germination (such as Pythium and Rhizoctonia) is reduced, and wintering capacity and planting density are improved. This also applies to late sowing, which would not be possible at other times due to the risk of crop compatibility.

The object of the present invention was to improve the application profile of the herbicidal active ingredient 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, taking into account:

a simplified application method that reduces costs for the consumer and is more gentle on the environment;

improving the flexibility of the application of active substances from the pre-emergence to post-emergence period of cultivated and weed plants;

improving the flexibility of the application of active substances, which allows the application before sowing crops;

improvements and flexibility in applying safe application efficiency to different soil types (eg soil type, soil moisture);

improvements and flexibility in applying safe efficiency in different types of irrigation (sprinkling);

improving the safe action on weeds that germinate from different depths of the soil;

improvements and flexibility for soils with different pH levels;

improving the safe action on resistant weed species, which provides a new opportunity for effective sustainable organization of processes, improving efficiency through synergies, with the last named tasks being of paramount importance.

This problem was solved by providing a herbicide mixture containing 2-[(2,4dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone and the additional herbicide cinmethylin.

Thus, the subject of the invention are herbicidal mixtures containing:

i) 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone

- 1 042560 ii) cinmethylin.

Another aspect of the present invention is a herbicide mixture which, along with components (i) and (ii), contains at least one additional herbicide from group I.

Another aspect of the present invention is a herbicidal mixture which, along with components (i) and (ii), contains at least one protective agent.

Another aspect of the present invention is a herbicide mixture which, along with components (i) and (ii), contains at least one additional herbicide from group I and one protective agent.

Definitions.

Group I herbicides:

acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxidim, alloxidim-sodium, ametrin, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro3-methylphenyl)- 5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachloropotassium, aminocyclopyrachlor-methyl, aminopyralid, amitrol, ammonium sulfamate, anilophos, azulam, atrazine, azaphenidine, azimsulfuron, beflubutamide, benazoline, benazoline-ethyl, benfluralin, methyl bensulfuresate, benzoline , bensulide, bentazone, benzobicyclone, benzofenap, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromophenoxime, bromoxynil, bromoxynyl-butyrate, -potassium, -heptanoate and -octanoate, buzoxynone, butachlor, butafenacil, butamiphos, butenachlor, butralin, butroxydim, butylate, cafenstrol, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazone, chlorine rimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidone-ethyl, cinosulfuron, clacifos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cymiluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cyclooxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl , -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-OB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dimron), dalapon, dazomet, n-decanol, desmedifam, detosyl pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5- dichlorobenzyl)-4,4dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor , dimeta methrin, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamide, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, etametsulfuron, etametsulfuron-methyl, etiosin, etofumesate, ethoxyphene, ethoxyphen- ethyl, ethoxysulfuron, etobenzanide, F-5231, i. e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro5-oxo-1H-tetrazol-1-yl]-phenyl]-ethanesulfonamide, F-7967, v. e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1Hbenzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidin-2,4(1H,3H)-dione, fenoxaprop, fenoxapropP, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrion, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florazulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycophen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron methyl sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamon, flutiacet, fluthiacet-methyl, fomesafen, fomesafen sodium, foramsulfuron, fosamine, glufosinate, glufosinate ammonium, glufosinate-P-sodium, glufosinate-ammonium, glufosinate-P-sodium, glyphosate, glyphosatammonium, -isopropylammonium, -diammonium, -dimethylammonium, -ka ly, -sodium and -trimesium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioate, galauxifen, galauxifenmethyl, halosafen, halosulfuron, halosulfuron-methyl, haloxifop, haloxyfop-P, haloxyfopethoxyethyl, haloxifop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinon, HW-02, i.e. 1-(dimethoxyphosphoryl)-ethyl-(2,4-dichlorophenoxy)acetate, imazametabenz, imazametabenz-methyl, imazamox, imazamox-ammonium, imazapik, imazapir-ammonium, imazapir, imazapyr-isopropylammonium, imazakquin, imazaquin-ammonium, imazethapyr, imazetapir -immonium, imazosulfuron, indanophane, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynyl-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutol, carbutylate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, metabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, metabenzthiazuron, methiopyrsulfuron, methiozolin, methylisothiocyanate, metobromuron, metolachlor, S-metolachlor, methosulam,

- 2 042560 methoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), nnorflurazone, butyric acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxacyclomefone, oxyfluorophen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxulam, pentachlorophenol, pentoxazone, pentoxamide, petroleum oils, phenmedifam, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxidim, promethone, promethrin, propachlor, propanil, propaquizafop, propazin, profam, propisochlor, propoxycarbazone, propoxycarbazone sodium, propyrisulfuron, propizamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribamben , pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxime, pyributicarb, pyridafol, pyridate, pyrifthalide, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, piroxulam, hinclorac, hinmerac, quinoclamine, chizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, chizalofop-P-tefuryl, rimsulfuron, saflufenacil, setoxydim, siduron, simazine, simetrin, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine -4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumetone, terbutylazine, terbutrin, tenylchlor, thiazopyr, thiencarbazone, thiencarbazonemethyl , thifensulfuron, thifensulfuron-methyl, thiobencarb, thiafenacil, tolpyralate, topramesone, tralkoxydim, triafamon, triallate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron sodium, trifludimoxazine, trifluralin, triflumethylsulfuron , tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, as well as the following compounds:

Examples of possible mixing partners for plant growth regulators are:

acibenzol, acibenzolαp-D-methyl, 5-aminolevulinic acid, ancimidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl) propionic acid, daminoside, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dicalium, disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetraline, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid ( IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthylacetic acid, nitrophenolate -mixture, 4-oxo-4[(2phenylethyl)amino]butyric acid, paclobutrazol, N-phenylphthalic acid, prohexadione, prohexadione-calcium, prohydrojasmon, salicylic acid, strigolactone, teknazen, thidiazuron, triacontanol, trinexapac, trinexapak-ethyl, tsitodef , uniconazole, uniconazole -P.

Herbicides.

The herbicides named in this description are known, for example, from The Pesticide Manual, 16th ed. 2012.

Protective equipment.

The following groups of compounds are taken into account, for example, as protective agents:

S1) compounds from the group of heterocyclic carboxylic acid derivatives:

S1 ^a ) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1 ^a ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid,

- 3 042560 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid ester (S1-1) (mefenpyr-diethyl), and related compounds, which are described in WO-A-91/07874;

S1 ^b ) dichlorophenylpyrazolecarboxylic acid derivatives (S1 ^b ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (S1-2), 1-(2,4 -dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid (S1-3), 1-(2,4dichlorophenyl)-5-(1,1-dimethyl-ethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806;

S1 ^c ) 1,5-diphenylpyrazole-3-carboxylic acid derivatives (S1 ^c ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S1-5), 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylic acid methyl ester (S1-6) and related compounds which are described, for example, in EP-A-268554;

S1 ^d ) compounds of the triazolecarboxylic acid type (S1 ^d ), preferably compounds such as phenchlorazole(-ethyl ester), i.e. 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EPA -346620;

S1 ^e ) compounds of the type 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 ^e ), preferably compounds such as ethyl ester 5- (2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylic acid (S1-8) or 5-phenyl-2isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds as described in WO-A91/ 08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid (S1-10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-11) (isoxafifen-ethyl) or -n-propyl ester (S1-12) or 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-13) as described in patent application WO-A-95/07897,

S2) compounds from the group of 8-quinolinoxy derivatives (S2):

S2 ^a ) compounds of the 8-quinolinoxyacetic acid type (S2 ^a ), preferably (1-methylhexyl) ester of (5-chloro-8-quinolinoxy)acetic acid (cloquintoset-mexyl) (S2-1), (1,3-dimethyl- but-1yl) ester (S2-2) of (5-chloro-8-quinolinoxy)acetic acid, -4-allyl-hydroxy-butyl ester (S2-3) of (5chloro-8-quinolinoxy)acetic acid, (5-chloro-8-quinolinoxy)acetic acid prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy)acetic acid ethyl ester (S2-5), (5-chloro-8-quinolinoxy) methyl ester )acetic acid (S2-6), (5-chloro-8quinolinoxy)acetic acid allyl ester (S2-7), 2-(2-propylidene-iminoxy)-1-ethyl ester (5-chloro-8quinolinoxy)acetic acid ( S2-8), (5-chloro-8-quinolinoxy)-acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds, which are described, for example, in EP-A-86750, EP-A -94349 and EPA-191736 or EP-A-0 492 366 as well as (5-chloro-8-quinolinoxy)acetic acid (S2-10), its hydrates and salts, e.g. its lithium, sodium, potassium, calcium salts , magnesium, aluminum, w iron, ammonium, quaternary ammonium, sulfonium, or phosphonium salts as described, for example, in WO-A-2002/34048;

S2 ^b ) compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2 ^b ), preferably compounds such as (5-chloro-8-quinolinoxy)malonic acid diethyl ester, (5-chloro8-quinolinoxy)malonic acid diallyl ester acids, (5-chloro-8-quinolinoxy)malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198,

S3) active ingredients of the dichloroacetamide type (S3), which are often used as pre-emergence preservatives (soil preservatives), such as:

dichlormide (N,N-diallyl-2,2-dichloroacetamide) (S3-1),

R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),

R-28725 (3-dichloroacetyl-2,2,-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4 -benzoxazine) (S3-4),

PPG-1292 (N-allyl-N-(1,3-dioxolan-2-yl)-methyl]-dichloroacetamide) from PPG Industries (S3-5), DKA-24 (N-allyl-N-[(allylaminocarbonyl) methyl]-dichloroacetamide) from Sagro-Chem (S3-6), AD-67 or MON 4660 (3-dichloroacetyl-1-oxa-3-aza-spiro[4,5]decane) from Nitrokemia or Monsanto (S3-7 ),

TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), diclonon (dicyclonone or BAS145138 or LAB145138 (S3-9) ((RS)-1-dichloroacetyl-3,3,8atrimethylperhydropyrrolo[1, 2-a]pyrimidin-6-one) from BASF, furilazole or MON 13900 (RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), as well as their (R )-isomer (S3-11),

S4) compounds from the class of acylsulfonamides (S4):

S4 ^a ) N-acylsulfonamides of formula (S4 ^a ) and their salts as described in WO-A-97/45016

- 4 042560 where RA ¹ (C1-C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, the last 2 residues being substituted by va substituents from the halogen group, (C ₁ -C ₄ )alkoxy, (C ₁ -C ₆ )haloalkoxy and (C ₁ -C ₄ )alkylthio and, in the case of cyclic residues, are also substituted by (C ₁ -C ₄ )alkyl and (C ₁ -C ₄ )haloalkyl;

R _a ² means halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )alkoxy, CF ₃ ;

m _A means 1 or 2;

v _A means 0, 1, 2 or 3;

S4 ^b ) compounds of the 4-(benzoylsulfamoyl)benzamide type of formula (S4 ^b ) and their salts as described in WO-A-99/16744

where RB ¹ , RB2 are independently hydrogen, (C ₁ -C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, (C ₃ -C ₆ )alkenyl, (C ₃ -C ₆ )alkynyl,

RB ³ is halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ ) haloalkyl, or (C ₁ -C ₄ )alkoxy, and mB is 1 or 2, such as where RB ¹ =cyclopropyl, RB ² =hydrogen and (RB ³ )=2-OMe (cyprosulfamides, S4-1), RB ¹ =cyclopropyl, RB ² =hydrogen and (RB ³ )=5-Cl-2-OMe (S4-2),

RB ¹ =ethyl, RB ² =hydrogen and (RB ³ )=2-OMe (S4-3), RB ¹ =isopropyl, RB ² =hydrogen and (RB ³ )=5-Cl-2-OMe (S44), And

RB ¹ =isopropyl, RB ² =hydrogen and (R= ³ )=2-OMe (S4-5);

S4 ^c ) compounds from the benzoylsulfamoylphenylurea class of formula (S4 ^c ) as described in EP-A-365484

where RC ¹ , Rc ² independently of each other mean hydrogen, (C ₁ -C ₈ )alkyl, (C ₃ -C ₈ )cycloalkyl, (C ₃ C ₆ )alkenyl, (C ₃ -C ₆ )alkynyl,

RC ³ means halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )alkoxy, CF ₃ ., and mC means 1 or 2;

For example:

1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,

1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea;

S4d) compounds of the N-phenylsulfonylterephthalamide type of formula ( ^S4d ) and their salts, which are known, for example, from CN 101838227

where RD ⁴ means halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )alkoxy, CF3;

mD means 1 or 2;

RD ⁵ means hydrogen, (C ₁ -C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, (C ₂ -C ₆ )alkenyl, (C ₂ -C ₆ )alkynyl, (C ₅ C ₆ )cycloalkenyl,

S5) active substances from the class of hydroxy-aromatic compounds and aromatic aliphatic derivatives of carboxylic acid (S5), for example, 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4- hydroxy salicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4 dichlorocinnamic acid, which are described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001,

S6) active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g. 1-methyl-3-(2thienyl)-1,2-dihydroquinoxalin-2-one, thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydro-quinoxalin-2-one-hydrochloride, 1-(2-methylsulfonylaminoethyl) -3(2-thienyl)-1,2-dihydro-quinoxalin-2-one, which are described in WO-A-2005/112630,

S7) compounds from the class of derivatives of diphenylmethoxyacetic acid (S7), for example diphenylmethoxyacetic acid methyl ester (CAS No. 41858-19-9) (S7-1), diphenylmethoxyacetic acid ethyl ester or diphenylmethoxyacetic acid, which are described in WO-A-98/ 38856,

- 5 042560

S8) compounds of formula (S8) as described in WO-A-98/27049

where symbols and indices have the following meanings:

RD ¹ means halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )haloalkyl, (C ₁ -C ₄ )alkoxy, (C ₁ -C ₄ )haloalkoxy,

RD ² means hydrogen or (C ₁ -C ₄ )alkyl,

RD ³ means hydrogen, (C ₁ -C ₈ )alkyl, (C ₂ -C ₄ )alkenyl, (C ₂ -C ₄ )alkynyl or aryl, each of the named C-containing residues being unsubstituted or substituted by one or more, preferably up to three identical or different residues from the group consisting of halogen and alkoxy; or their salts, nD means integer 0-2,

S9) active substances from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example:

1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-( 5-tetrazolyl-carbonyl)-2-quinolone (CAS No. 95855-00-8), which are described in WO-A-1999/000020,

S10) compounds of formula (S10a) or (S10b) as described in WO-A-2007/023719 and WO-A2007/023764

(S10 ^a ) (S10 ^b ) , where RE ¹ means halogen, (C ₁ -C ₄ )alkyl, methoxy, nitro, cyano, CF3, OCF3,

YE, ZE independently means O or S, nE means integer 0-4,

RE ² means (C ₁ -C ₁₆ )alkyl, (C ₂ -C ₆ )alkenyl, (C ₃ -C ₆ )cycloalkyl, aryl; benzyl, halobenzyl,

RE ³ means hydrogen or (C ₁ -C ₆ )alkyl,

S11) active ingredients of the oxyimino type (S11) which are used as seed dressings, such as:

oxabethrinyl ((2)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is used as a seed dressing for millet against damage caused by metolachlor, fluxofenim (1-(4- chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2), which is used as a seed dressing for millet against damage induced by metolachlor, and cyometrinil or CGA-43089 ((2)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is used as a seed dressing for millet against damage caused by metolachlor,

S12) active ingredients from the class of isothiochromanones (S12), such as methyl-[(3-oxo-1H2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS No. 205121-04-6) (S12-1 ) and related compounds from WO-A-1998/13361,

S13) one or more compounds from the group (S13):

naphthalic anhydride (1,8-naphthalenedicarboxylic acid anhydride) (S13-1), which is used as a protectant for corn seed dressing against damage caused by thiocarbamate herbicides, fenclorim (4,6-dichloro-2-phenylpyrimidine) (S13-2 ) which is used as a protectant against pretilachlor in seeded rice, flurazol (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3) which is used as a protectant for dressing millet seeds against damage caused by alachlor and metolachlor,

CL 304415 (CAS No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid which is used as a corn preservative from damage caused by imidazolinones,

MG 191 (CAS No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is used as a corn preservative,

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MG 838 (CAS No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia, disulfotone (Ο,Ο-diethyl S-2- ethylthioethyl phosphorodithioate) (S13-7), dietholate (O,O-diethyl-O-phenylphosphorothioate) (S13-8), mephenate (4-chlorophenyl-methylcarbamate) (S13-9),

S14) active ingredients which, in addition to their herbicidal action against harmful plants, also have a protective action against cultivated plants, such as rice, such as:

dimepiperate or MY-93 (S-1-methyl-1-phenylethyl-piperidine-1-carbothioate), which is a rice protectant against damage caused by the herbicide molinate, daimuron or SK 23 (1-(1-methyl-1- phenylethyl)-3-p-tolyl-urea), which is a protective agent for rice against damage caused by the herbicide imazosulfuron, kumiduron=JC-940 (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenyl- ethyl)urea, see JP-A60087254), which is a protectant for rice against damage caused by certain herbicides, methoxyphenone or NK 049 (3,3-dimethyl-4-methoxy-benzophenone), which is a protectant for rice against damage caused by some herbicides,

CSB (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS No. 54091-06-4), which is a rice protectant against damage caused by certain herbicides,

S15) compounds of formula (S15) or their tautomers

ABOUT

which are described in WO-A-2008/131861 and WO-A-2008/131860, where RH ¹ is a (C ₁ -C ₆ ) haloαalkyl residue, and

RH ² means hydrogen or halogen, and ^R H3, ^r h ⁴ independently of each other mean hydrogen, (C ₁ -C ₁₆ )alkyl, (C ₂ -C ₁₆ )alkenyl or (C ₂ C ₁₆ )alkynyl, each of of the last three residues is unsubstituted or may be substituted by one or more of halo, hydroxy, cyano, (C ₁ -C ₄ )α alkoxy, (C 1 C ₄ ) haloalkoxy, (C ₁ -C ₄ ) alkylthio, (C ₁ - C ₄ )alkylamino, di[(C ₁ -C ₄ )alkyl]-amino, [(C 1 -C ₄ )alkoxy]carbonyl, [(C ₁ -C ₄ )haloalkoxy]-carbonyl, (C ₃ -C ₆ ) cycloαalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or (C ₃ -C ₆ )cycloαalkyl, (C ₄ -C ₆ )cycloalkenyl, (C ₃ -C ₆ )cycloalkyl which is fused on the ring side with one 4-6 membered saturated or unsaturated carbocyclic ring, or (C ₄ C ₆ )cycloalkenyl which is fused on the ring side with one 4-6-membered saturated or unsaturated carbocyclic ring om, and each of the last 4 residues named is unsubstituted or may be substituted by one or more residues from the group of halogen, hydroxy, cyano, (C ₁ -C ₄ )alkyl, (C1C ₄ )haloαalkyl, (C ₁ -C ₄ )alkoxy _{. _ _ _ _ _ _ _} , [(C1-C ₄ )haloalkoxy]-carbonyl, (C ₃ -C ₆ )cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or

RH ³ means (C 1 -C ₄ )-alkoxy, (C ₂ -C ₄ )alkenyloxy, (C ₂ -C ₆ )alkynyloxy or (C ₂ -C ₄ )haloalkoxy, and

RH ⁴ means hydrogen or (C1-C ₄ )alkyl, or

RH ³ and RH ⁴ together with the directly connected N-atom means a 4 to 8-membered heterocyclic ring, which, in addition to the N-atom, can also contain other ring heteroatoms, preferably up to 2 other ring heteroatoms from the group N, O and S and which is unsubstituted or substituted by one or more of halo, cyano _, nitro, (C1- _C4 )alkyl, (C1- _C4 )haloalkyl, ( _CrC4 )alkoxy, (C1- _C4 )haloalkoxy, and (C1- C ₄ ) alkylthio,

S16) active ingredients which are mainly used as herbicides, but which also have a protective effect on cultivated plants, for example:

(2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-otolyloxy)propionic acid (mecoprop), 4-(2 ,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-otolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid,

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3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl-3,6-dichloro-2methoxybenzoate (lactidichloro-ethyl).

Preferred protective agents are: cloquintoset-mexil, cyprosulfamide, fenchlorazole-ethyl ether, isoxadifen-ethyl, mefenpyr-diethyl, fenchlorim, cymiluron.

Particularly preferred protective agents are: cloquintoset-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

Most preferred is: mefenpyr-diethyl.

AB/ha.

In general, the abbreviation AB/ha is used in this description, which means active ingredient per hectare, relative to 100% active ingredient. All percentages in the specification are in percent by weight (abbreviation: wt%) and refer, unless otherwise indicated, to the relative weight of the respective component relative to the total weight of the herbicidal mixture/composition (eg, as a composition).

Cinmethylin (CAS RN 87818-31-3) is a racemate of (+/-)-2-exo-(2-methylbenzyloxy)-1methyl-4-isopropyl-7-oxabicyelo[2.2.1]heptane

The ratio of the two enentiomers to each other is approximately the same. The preparation of compounds saturated with enantiomers is known from EP 0081893 A2.

The herbicidal compositions according to the invention contain the component of the mixture according to the invention i), ii), and and, if necessary, contain other herbicides and protective agents and other components, for example agrochemical active substances from the group of insecticides and fungicides and/or conventional additives and/or auxiliaries means for the preparative form for the field of plant protection.

The herbicidal mixtures/compositions according to the invention have, in a preferred form, a synergistic effect as an improvement in the application profile. These synergistic effects can be observed, for example, when the herbicidal component is used together, however, they can also often occur when the application is divided over time (splitting). It is also possible to apply individual herbicides or combinations of herbicides in several portions (sequential application), for example, a pre-emergence application that follows a post-emergence application or an early post-emergence application that follows a mid or late post-emergence application. In this case, the joint or topical application of the active ingredients of the herbicidal mixtures/compositions according to the invention is preferred.

Synergistic effects make it possible to reduce the application rates of individual active substances, increase the effect at the same application rate, control new types (gaps), increase the period of application and / or reduce the necessary applications in individual cases and - as a result for the consumer - an economically and environmentally preferable control system with weeds.

Application rates of herbicidal components in herbicidal mixtures/formulations can vary within wide ranges. When applied with a consumption rate of 1-5000 g AS/ha of the herbicidal component in the pre- and post-emergence period, a wide range of annual and perennial weeds, weeds, and sedge grasses are controlled.

The application rates of the herbicidal component in the mixtures/formulations are in the following weight ratio:

i):ii):

in general (1-1000):(1-1000), preferably (1-100):(1-100), particularly preferably (1-50):(150).

The application rates of the respective herbicidal component in the herbicidal mixtures/formulations are as follows.

Component (i): in general 1-2000 g AS/ha, preferably 10-1000 g AS/ha, particularly preferably 10-500 g AS/ha 2-[(2,4-dichlorophenyl)methyl]-4,4 -dimethyl-3-isoxazolidinone;

Component ii): in general 1-2000 g AS/ha, preferably 10-1000 g AS/ha, particularly preferably 10-500 g AS/ha cinmethylin.

If the composition contains a single protectant, the application rate is generally 5-2000 g AS/ha, preferably 10-500 g AS/ha and particularly preferably 10-300 g AS/ha.

Accordingly, from the above application rates it is possible to calculate the mass percentages (wt.%) of the herbicidal component relative to the total mass of the herbicidal mixtures, which may also additionally contain other components.

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The mixtures/compositions according to the invention have excellent herbicidal activity against a wide range of economically important mono- and dicotyledonous annual pests. The active ingredients also work well on perennial pests that are difficult to control and may regrow from rhizomes, rhizomes or other organs.

Therefore, the subject of the present invention is also a method for controlling unwanted plants or regulating plant growth, preferably in plant cultures, in which the mixtures/compositions according to the invention are applied to plants (for example, harmful plants such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), on seed material (for example, grains, seeds or vegetative reproductive organs, such as tubers or shoots with buds) or on the soil on which the plants grow (for example, on a cultivated surface). In this case, the mixtures/compositions according to the invention can be applied, for example, in the pre-sowing (if necessary, also when fertilizing the soil), pre-emergence and/or post-emergence period. In particular, mono- and dicotyledonous weeds that can be controlled with the mixtures/compositions according to the invention should be mentioned as examples, but the invention should not be limited to these names.

Monocot plant species: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum.

Dicotyledon weed species: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis , Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio , Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola and Xanthium.

If the mixtures/compositions according to the invention are applied to the surface of the earth before the sprouts germinate, then the growth of the weed sprouts is completely stopped, or the weeds grow to the cotyledon stage, but then their growth stops and, eventually, they die within 3-4 weeks after the start of growth . This can also be used if IBS (Incorporated By Sowing) application methods are used. In this case, herbicidal mixtures/compositions are applied to the bed at the time of sowing.

When the mixtures/compositions according to the invention are applied to the green parts of the plants in post-emergence application, growth ceases after the treatment, and the harmful plants at the stage of growth they were at at the time of application, or completely die after a certain period of time, thus very early and at for a long period eliminate competition in the form of harmful weeds. The mixtures/compositions according to the invention can also be applied to rice in water and then spread through the soil, sprouts and roots.

The mixtures/compositions according to the invention are characterized by rapid application and long-lasting herbicidal action. The rain resistance of the active compounds in the mixtures/formulations according to the invention is generally sufficient. It is of particular advantage that the effective dosages of the components i) and ii) used in the mixtures/compositions according to the invention can be so low that their effect on the soil also remains optimally low. Thus, their use appears to be feasible in sensitive crops and also practically prevents groundwater contamination. By means of the active ingredient combinations according to the invention, the required dosage rates of the active ingredients can be significantly reduced.

When components i) and ii) are used together in the mixtures/compositions according to the invention, super-additive (=synergistic) effects occur in the preferred embodiment as a use profile improver. In this case, the action in combinations is stronger than the expected sum of the actions of the individual herbicides used. Synergistic effects allow for increased and/or prolonged exposure (continuous exposure); control a wide range of weeds, grass weeds and sedge grasses, in part with only one application or a small number of applications; rapid onset of herbicidal action; control new species (gaps); for example, to control species that have tolerance or resistance to one or more herbicides; increase the period of application and/or reduce the necessary applications in individual cases and, as a result for the consumer, obtain an economically and environmentally preferable weed control system.

The named properties and advantages are necessary for the practical control of weeds in order to prevent the emergence of undesirable competitive plants in agricultural/forestry/horticultural crops, meadows/grasslands or energy crops (biogas, bio-ethanol) and thus preserve quantitatively and qualitatively and/ or increase productivity. These new combinations in the herbicidal mixtures/formulations according to the invention far exceed the technical standard with regard to the properties described.

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Although according to the invention the mixtures/compositions show excellent herbicidal activity against mono- and dicotyledonous weeds, cultivated plants, economically important crops, for example, dicotyledonous crops of the species Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca , Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solarium, Vicia, or monocots of the species Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular, Zea and Triticum are only slightly affected by the structure of the respective compound and its application rates, or are not affected at all.

In addition, the mixtures/compositions according to the invention may partially have plant growth regulating properties in cultivated plants. They interfere with and regulate plant metabolism and this can be used to target plant components and to facilitate harvesting, such as by triggering desiccation and stopping growth. They further enable the general regulation and inhibition of unwanted vegetative growth without destroying the plants. Inhibition of vegetative growth plays a large role in many mono- and dicotyledonous crops, for example, in this way, yield losses during storage can be reduced or completely prevented.

Due to their improved application profile, the mixtures/compositions according to the invention can also be used to control harmful plants in known plant cultures or newly developed, tolerant or genetically modified crop plants. Transgenic plants (GMOs) are usually characterized by particularly advantageous properties, for example by their resistance to certain pesticides, in particular to certain herbicides (such as resistance to components i) and ii) in the mixtures/preparations according to the invention) eg resistance to insect pests, plant diseases or their pathogens, such as certain insects or micro-organisms such as fungi, bacteria or viruses. Other special properties are usually related to the harvested crop, regarding quantity, quality, storage stability, as well as the composition of special components. Thus, transgenic plants with an increased starch content or an altered starch property, or plants with a different fatty acid composition in the harvested crop or an increased vitamin content or energy properties are known. Other special properties are tolerance or resistance to abiotic stress factors such as heat, cold, drought, high salt content and ultraviolet radiation. Likewise, the mixtures/compositions according to the invention, due to their herbicidal and other properties, can also be used to control harmful plants in cultures of known or obtained by mutation breeding plants, as well as from crosses of mutagenic and transgenic plants.

Conventional methods for obtaining new plants that have new altered qualities compared to previously existing plants are, for example, classical cultivation methods and the creation of mutated plants. Alternatively, new plants with modified properties can be obtained using genetic engineering techniques (see, for example, EP 0221044 A, EP 0131624 A). Described, for example, in many cases: genetic modifications of cultivated plants caused by a change in the starch synthesized in plants (for example, WO 92/011376 A, WO 92/014827 A, WO 91/019806 A); transgenic crop plants that are resistant to certain herbicides such as glufosinate (see, for example, EP 0242236 A, EP 0242246 A) or glyphosate (WO 92/000377 A) or sulfonylurea (EP 0257993 A, US 5,013,659) or combinations or mixtures these herbicides through gene stacking, as transgenic crop plants, for example, corn or soybeans under the trade name or designation Optimum™ GAT™ (ALS glyphosate resistance); transgenic crop plants, such as cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make plants resistant to certain pests (EP 0142924 A, EP 0193259 A); transgenic crop plants with a modified fatty acid composition (WO 91/013972 A by crop plants with a modified fatty acid composition (WO 91/013972 A); genetically modified crop plants with a new composition or secondary substances, for example new phytoalexins, which cause increased resistance to diseases (EP 0309862 A, EP 0464461 A); genetically modified plants with reduced photorespiration that have high yield and increased resistance to stress (EP 0305398 A); transgenic crop plants that produce pharmaceutically or diagnostically important proteins (molecular farming); transgenic crop plants that are characterized by high yield or improved quality, transgenic crop plants that are characterized by combinations of, for example, the above-mentioned new properties (gene stacking).

The person skilled in the art is aware of many molecular biological technologies that can be used to produce new transgenic plants with altered properties; see, for example, I. Potrykus and G. Spangenberg (ed.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, Trends in Plant Science 1 (1996) 423-431). For genetic engineering manipulations of this kind, nucleic acid molecules can be delivered into plasmids that allow mutagenesis or modification of the nucleotide DNA sequence. Using standard techniques, for example, cation exchange can be carried out, partial sequences can be removed or

- 10 042560 natural or synthetic sequences are added. Adapters or linkers can be attached to DNA fragments to connect DNA fragments to each other, see e.g. Sambrook et al., 1989,

Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor,

NY; or Winnacker Gene und Klone, VCH Weinheim 2nd ed. 1996.

Generating plant cells with reduced activity of a gene product can, for example, be achieved by expressing at least one corresponding antisense RNA, one sense RNA to extract RNA interference, or by expressing at least the corresponding generated ribosome by a specific transcript of said gene product.

In addition, DNA molecules can be used that span the overall encoded sequence of the gene product, including possible flanking sequences present, as well as DNA molecules that span only a portion of the encoded sequence, which portion must be long enough to cause an antisense effect in cells. It is also possible to use DNA sequences that indicate a high degree of homology to the encoded sequences, but are not completely identical.

When nucleic acid molecules are expressed in plants, the synthetic protein can be localized in any compartment of the plant cell. But in order to achieve localization in a specific compartment, the encoded region can, for example, be associated with DNA sequences that provide localization in one specific compartment. Such sequences are known to the skilled person (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Expression of nucleic acid molecules can also occur in plant cell organelles.

Transgenic plant cells can be regenerated by known methods into whole plants. In transgenic plants, in principle, we can talk about plants of any species, i.e., both monocots and dicots. Thus, commercially available transgenic plants may have altered properties due to increased expression, suppression or inhibition of homologous (=natural) genes or gene sequence, or expression of heterologous (=foreign) genes or gene sequence.

Further, the subject of the present invention is also a method for controlling undesired growth of plants (for example, harmful plants), preferably in crops such as cereal crops (for example, durum and soft wheat, barley, rye, oats, their crosses, such as triticale, planted or rice sown in a hill or field, corn, millet, such as sorghum), sugar beet, sugar cane, rapeseed, cotton, sunflower, soybeans, potatoes, tomatoes, beans, such as common beans and beans, flax, meadow grass, orchards, plantation crops, lawns and lawns, as well as areas near residential buildings and industrial buildings, travel parks, especially preferably in monocotyledonous crops such as cereals, such as wheat, barley, rye, oats, their crosses, such as triticale, rice, corn and millet, as well as dicotyledonous crops, such as sunflower, soybeans, potatoes, tomatoes, peas, carrots and fennel, and components i) and ii) are applied with a herbicide positions according to the invention, together or separately, for example, in the pre-emergence period (very early to very late), post-emergence period or in the pre- and post-emergence period, on plants, for example, harmful plants, plant parts, plant seeds or on a surface on which plants grow, for example, on a cultivated surface.

The subject of the invention is also the use of the herbicidal composition according to the invention, containing the components i) and ii) for the control of harmful plants, preferably in plant cultures, preferably in the plants named above. Further subject of the invention is also the use of the herbicidal composition according to the invention, comprising components i) and ii) for the control of herbicide-resistant harmful plants (eg resistance to TSR and EMR in ALS and ACCase), preferably in plant cultures, preferably in the plants named above.

The subject of the invention is also a method using the herbicidal composition according to the invention containing components i) and ii) for the selective control of harmful plants in crops of useful plants, preferably in the plants named above, as well as its use.

The subject of the invention is also a method for combating unwanted plant growth, containing a herbicidal composition according to the invention, containing components i) and ii), as well as its use, in plant cultures that are genetically modified (transgenic) or obtained by mutation selection, and which are resistant to active ingredients such as, for example, 2,4-D, dicamba, or to herbicides that block essential plant enzymes, such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD), respectively to herbicides from the group of sulfonylurea, glyphosate, glufosinate or benzoylisoxazole and similar active ingredients, or to any combination of these active ingredients. Especially preferably, herbicidal compositions can be used in transgenic crop plants that are resistant to a combination of glyphosate and glufosinate, glyphosate and sulfonylurea, or imidazolinones. Very preferably, the herbicidal compositions of the invention can be used in transgenic crop plants, such as corn or soybeans under the trade name or designation Optimum™ GAT™ (ALS glyphosate resistance).

The subject of the invention is also the use of the herbicidal composition according to the invention, containing the components i) and ii) for the control of harmful plants, preferably in plant cultures, preferably in the plants named above.

The herbicidal compositions according to the invention can also be used for non-selective control of undesirable plants, for example, in plantation crops, on roadsides, landing sites, near industrial or railway facilities; or selectively applied to control unwanted plants in energy crops (biogas, bio-ethanol).

The herbicidal compositions according to the invention can be present both as mixed formulations of components i) and ii) and, if necessary, with other agrochemical active ingredients, additives and/or conventional formulation auxiliaries, which are diluted for application in the usual way with water, or obtained in the form of so-called mixtures in containers after a general dilution of the obtained separately or partially separated components with water. Under certain conditions, mixed compositions can be diluted with other liquids or solids or also used undiluted.

The mixtures/formulations according to the invention can be formulated in various ways, depending on which biological and/or chemical-physical parameters are given. As general formulation options, for example, take into account: Spray powders (WP), water-soluble concentrate, emulsifiable concentrate (EC), aqueous solutions (SL), emulsions (EW) as oil-in-water emulsions and water - in oil, solutions for spreading or emulsions, suspension concentrates (SC), dispersions, oil dispersions (OD), suspoemulsions (SE), pollinators (DP), dressing agents, granulates for soil application or spreading (GR) or water-dispersible granulates (WG), ultra-low volume formulations, microcapsule dispersions or paraffin dispersions.

Certain types of formulations are known in principle and are described, for example, in: Manual on Development and Use of FAO and WHO Specifications for Pesticides, FAO and WHO, Rome, Italy, 2002; Winnacker-Kuchler, Chemische Technologie, vol. 7, C. Hanser Verlag Munich, 4th ed. 1986; van Valkenburg, Pesticide Formulations, Marcel Dekker N.Y. 1973; K. Martens, Spray Drying Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries such as inerts, surfactants, solvents and other additives are also known and described in, for example: Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2nd ed., Darland Books, Caldwell N.J.; H.v. Olphen, Introduction to Clay Colloid Chemistry; 2nd ed., J. Wiley & Sons, N.Y. Marsden, Solvents Guide, 2nd ed., Interscience, New York 1950; McCutcheon's, Detergents and Emulsifiers Annual, MC Publ. Corp., Ridegewood N.J.; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., New York 1964; Schonfeldt, Grenzflachenaktive Athylenoxidaddukte, Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Kuchler, Chemische Technologie, volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

Based on these formulations, it is also possible to obtain combinations with other agrochemical active ingredients, such as, for example, fungicides, insecticides, as well as protective agents, fertilizers and/or growth regulators, for example, in the form of finished formulations or in the form of mixing in containers.

Powders for spraying (wettable powders) are preparations uniformly dispersed in water, which, in addition to active ingredients, in addition to several diluents or inert substances, also contain non-ionic and / or ionic surfactants (wetting agents, dispersants), for example, polyoxyethylated alkylphenols, polyoxyethylated aliphatic alcohols or polyoxyethylated aliphatic amines, propylene oxide-ethylene oxide copolymers, alkane sulfonates, alkylbenzenesulfonates or alkylnaphthalene sulfonates, sodium lignin sulphonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonic acid, sodium dibutylnaphthalene sulphate or also sodium oleolmethyl taurine acid.

Emulsifiable concentrates are obtained by dissolving the active ingredients in an organic solvent or solvent mixture, for example, butanol, cyclohexanone, dimethylformamide, acetophenone, xylene, or also in high-boiling aromatic compounds or hydrocarbons, with the addition of one or more surfactants of an ionic and/or nonionic type (emulsifiers). As emulsifiers, for example, the following can be used: calcium salts of alkylarylsulfonic acid, such as Ca-dodecylbenzenesulfonate or non-ionic emulsifiers, such as fatty acid polyglycol ester, alkylaryl polyglycol ether, fatty alcohol polyglycol ester, propylene oxide ethylene oxide copolymers, alkyl polyether, fatty acid sorbitan ester, sorbitan polyoxyethylene ester. fatty acids or polyoxyethylene sorbitan ether.

Pollinators are obtained by grinding the biologically active substance with finely divided solids such as, for example, talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

- 12 042560

Suspension concentrates are suspensions of active ingredients based on water.

They can be obtained, for example, by wet grinding with standard bead mills, optionally with the addition of other surfactants, as, for example, already mentioned in other types of formulations. In addition to the suspended active ingredient or substances, other active ingredients may also be present in the formulation in dissolved form.

Oil dispersions are oil-based suspensions of the active ingredients, oil being understood to mean various organic liquids, for example vegetable oils, aromatic or aliphatic solvents or a fatty acid alkyl ester. They can be obtained, for example, by wet grinding with standard bead mills, if necessary, with the addition of other surfactants (wetting agents, dispersants), as, for example, already mentioned in other types of formulations. In addition to the suspended active ingredient or substances, other active ingredients may also be present in the formulation in dissolved form.

Emulsions, such as oil-in-water (EW) type emulsions, can be prepared using stirrers, colloid mills and/or static mixers using mixtures of water and water-immiscible aqueous organic solvents and, if necessary, surfactants, such as for example , has already been named in other types of formulations. The active substances here are present in dissolved form.

Granules can be produced by spraying the active ingredient onto granular inert adsorbents or by applying the concentrate of active ingredients with binders, for example polyvinyl alcohol, sodium polyacrylic acid or also mineral oils, onto the surface of a filler such as sand, kaolinite, chalk or granular inert material. Also for the manufacture of fertilizer granules, the appropriate active ingredients are crushed in the usual way, optionally mixed with fertilizers. Water-dispersible granulates are generally produced by conventional methods such as spray drying, fluidized bed granulation, disc granulator granulation, mixing in a high-speed mixing granulator and extrusion without solid inert. For the production of disc granules, fluidized bed granulates, extruder and spray granulates, see for example the method in the SprayDrying Handbook 3rd Ed. 1979, G. Goodwin Ltd., London; J.E. Browning, Agglomeration, Chemical and Engineering 1967, pp. 147ff. Perry's Chemical Engineer's Handbook, 5th ed., McGraw-Hill, New York 1973, S. 8-57.

For further details on plant protection compositions, see, for example, G.C. Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and J.D. Freyer, S.A. Evans, Weed Control Handbook, 5th ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

Agrochemical compositions generally contain 0.1 to 99% by weight, in particular 2 to 95% by weight, of the active ingredients of the herbicidal component, the following concentrates being commonly used depending on the type of composition: In spray powders, the concentration of the active ingredient is, for example, 10-95 wt. % residue to 100 wt. % of the usual formulation components. In emulsifiable concentrates, the concentration of active substance can be, for example, 5-80 wt.%. Dust-like compositions usually contain 1-20 wt.% of the active substance, solutions for scattering contain approximately 0.2-25 wt.% of the active substance. In granulates such as water-dispersible granules, the content of the active ingredient depends in part on whether the active compound is present in liquid or solid form and which granulating aids and excipients are used. As a rule, the water content of the dispersible granules is 10-90% by weight.

In addition, the active ingredient compounds mentioned optionally contain the usual setting, wetting, dispersing, emulsifying, preservative, antifreeze agents and solvents, fillers, carriers, dyes, defoamers, brake evaporators and pH-influencing agents. and viscosity.

The herbicidal action of the mixtures/compositions according to the invention can, for example, be improved with surfactants, for example with a wetting agent from the fatty alcohol polyglycol ether series. The fatty alcohol polyglycol ethers preferably contain 10-18 carbon atoms per fatty alcohol residue and 2-20 ethylene oxide units per part of the polyglycol ether. The fatty alcohol polyglycol ethers can be present in non-ionic form or in ionic form, for example as sulfates or phosphates of the fatty alcohol polyglycol ether, which can, for example, be used in the form of alkali metal salts (for example sodium or potassium salts) or ammonium salts, or also in in the form of alkali metal salts, as magnesium salts, as sodium sulfate of diglycol ether C ₁₂ /C ₁₄ fatty alcohol (Genapol® LRO, Clariant GmbH); see for example EP-A-0476555, EP-A-0048436, EP-A-0336151 or USA-4,400,196 sowie Proc. EWRS Symp. Factors Affecting Herbicidal Activity and Selectivity, 227-232 (1988). Non-ionic fatty alcohol polyglycol ethers are, for example, containing 2-20, preferably 3-15 units of ethylene oxide polyglycol ether (C ₁₀ -C ₁₈ )-, preferably (C ₁₀ -C ₁₄ ) fatty alcohol (for example, isotridecyl alcohol polyglycol ether), for example , from Genapol® X-13 042560 series, like Genapol® X-030, Genapol® X-060, Genapol® X-080 or Genapol® X-150 (all manufactures

LLC Clariant).

The present invention further comprises combinations of the mixtures/formulations according to the invention with the previously named wetting agents from the fatty alcohol polyglycol ether series, which preferably contain 10-18 C atoms in the fatty alcohol residue and 2-20 ethylene oxide units in the polyglycol ether part contain and may also be present in non-ionic or ionic (eg, as fatty alcohol polyglycol ether sulfates) form. Preferred are sodium sulfate diglycol ether C ₁₂ /C ₁₄ -fatty alcohol (Genapol® LRO, OOO Clariant) and polyglycol ether isotridecyl alcohol, with 3-15 units of ethylene oxide, for example from the Genapol® X-series, such as Genapol® X-030 , Genapol® X-060, Genapol® X-080 and Genapol® X-150 (all from 000 Clariant). It is further known that fatty alcohol polyglycol ethers, such as non-ionic or ionic fatty alcohol polyglycol ethers (for example polyglycol fatty alcohol ether sulphates), are also suitable as penetration and action enhancers for a number of other herbicides, among others also for herbicides of the imidazolinone series (see , for example, EP-A-0502014).

The herbicidal action of the mixtures/compositions according to the invention can also be enhanced by the use of vegetable oils. The term vegetable oils is understood to mean oils of oil-containing plant species such as soybean, rapeseed, corn, sunflower, cottonseed, linseed, coconut, palm, milk thistle or castor oils, in particular rapeseed oil, as well as its interesterification products, for example, an alkyl ester such as rapeseed oil methyl or ethyl ester.

Vegetable oils are preferably esters of C ₁₀ -C ₂₂ -, preferably C ₁₂ C ₂₀ fatty acids. Esters of C ₁₀ -C ₂₂ fatty acids are, for example, esters of unsaturated or saturated C ₁₀ -C ₂₂ fatty acids, in particular those with an even number of carbon atoms, such as erucic acid, lauric acid, palmitic acid, and particularly preferably C ₁₈ fatty acids like stearic acid, butyric acid, linoleic acid or linolenic acid.

Examples of C ₁₀ -C ₂₂ fatty acid esters are esters which are obtained by replacing glycerol or glycol with C ₁₀ -C ₂₂ fatty acids, which are present, for example, in oils of oily plant species, or C 1 -C ₂₀ -alkyl esters. -C ₁₀ -C ₂₂ -fatty acids, which can be obtained, for example, by interesterification of the above-mentioned glycerol or glycol esters of C ₁₀ -C ₂₂ fatty acids with C 1 -C ₂₀ -alcohols (for example, methanol, ethanol, propanol or butanol). Interesterification can be carried out using known methods, which are described, for example, in Rompp Chemie Lexikon, 9th ed., vol. 2, page 1343, ed. Thieme Verlag Stuttgart.

As esters of C 1 -C ₂₀ -alkyl-C ₁₀ -C ₂₂ fatty acids, methyl, ethyl, propyl, butyl ester, 2-ethyl-hexyl and dodecyl ester are preferred. As esters of glycolic and glyceric C ₁₀ -C ₂₂ fatty acids, homogeneous or mixed glycol or glyceric esters of C ₁₀ -C ₂₂ fatty acids are preferred, in particular fatty acids with an even number of carbon atoms, such as, for example, erucic acid, lauric acid, palmitic acid and particularly preferably C ₁₈ fatty acids such as stearic acid, butyric acid, linoleic acid or linolenic acid.

As vegetable oils in the herbicidal mixtures/compositions according to the invention can be present, for example, in the form of commercially available oil-containing composition additives, in particular based on rapeseed oils, such as Hasten® (Victorian Chemical Company, Australia, hereinafter referred to as Hasten, the main component : rapeseed oil ethyl ester), Actirob®B (Novance, France, hereafter called ActirobB, main component: rapeseed oil methyl ester), Rako-Binol® (Bayer AG, Germany, hereafter called Rako-Binol, hereafter called Rapsol) , Renol® (Stefes, Germany, hereinafter referred to as Renol, main component of rapeseed oil: rapeseed oil methyl ester) or Stefes Mero® (Stefes, Germany, hereinafter referred to as Mero, main component: rapeseed oil methyl ester).

In another embodiment, the present invention comprises combinations of components i) and ii) with the previously named vegetable oils, such as rapeseed oil, preferably in the form of commercially available oil-containing additives to compositions, in particular based on rapeseed oil, such as Hasten®, Actirob®B , Rako-Binol®, Renol® or Stefes Mero®.

For use, the formulations normally present are diluted with water in the usual manner, for example in the form of spray powders, emulsifiable concentrates, dispersions and water-dispersible granules. Dust compositions, soil granulates or granulates, and spray solutions are usually not diluted with other inert substances before use.

The active ingredients can be applied to plants, plant parts, plant seeds or cultivated surface (soil), preferably green plants and plant parts and, if necessary, additionally to soil.

- 14 042560

A possible application is the co-application of the active ingredients in the form of mixing in a container, wherein the optimal concentrations of the formulations of the individual active ingredients are mixed together in a tank with water and the resulting spray liquids are used.

The advantage of the general herbicidal composition of the herbicidal mixtures according to the invention with components i) and ii) is the easy handling, since the amount of the components is already in the correct ratio to each other. In addition, formulation auxiliaries can be optimally matched to one another.

A. General Formulation Examples.

a) Pollinator can be obtained by mixing 10 wt. parts of the active ingredient/mixture of active ingredients and 90 wt. parts of talc as an inert substance and grinding in a hammer mill.

b) Dispersible in water, a wettable powder is obtained by mixing 25 wt. parts of active ingredient/mixture of active ingredients, 64 wt. parts containing kaolin clay as an inert substance, 10 wt. parts of potassium ligninsulfonic acid and 1 wt. parts of sodium oleoylmethyltaurine as a wetting agent and dispersant and crushed in a pin crusher.

c) Easily dispersible in water suspension concentrate is obtained by mixing 20 wt. parts of the active ingredient/mixture of active ingredients, 5 wt. parts tristyrylphenolpolyglycol ether (Soprophor BSU), 1 wt. parts of sodium ligninsulfonic acid (Vanisperse CB) and 74 wt. parts of water and grinding in a ball mill to a grinding fineness of 5 microns.

d) Easily dispersible in water oil dispersion is obtained by mixing 20 wt. parts of the active ingredient/mixture of active ingredients with 6 wt. parts of alkylphenol polyglycol ether (© Triton X 207), 3 wt. parts of isotridecanol polyglycol ether (8 EO) and 71 wt. parts of paraffinic mineral oil (boiling range, for example, about 255-277°C) and grinding in a ball grinder to a fineness of grinding of 5 microns.

e) Emulsifiable concentrate is obtained from 15 wt. parts of the active ingredient/mixture of active ingredients, 75 wt. parts of cyclohexanone as a solvent and 10 wt. parts of oxoethylated nonylphenol as an emulsifier.

f) Water-dispersible granules are obtained by mixing 75 wt. parts of the active substance / mixture of active substances:

wt. parts of calcium ligninsulfonic acid, wt. parts of sodium lauryl sulfate, wt. parts of polyvinyl alcohol, and wt. parts of kaolin, grinding in a pin crusher, and granulating the powder in a fluidized bed by spraying water as the granulating liquid.

g) Water-dispersible granulate can also be obtained by mixing 25 wt. parts of the active substance / mixture of active substances:

wt. parts of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, wt. parts of oleylmethyltaurine sodium, wt. parts of polyvinyl alcohol, wt. parts of calcium carbonate, and wt. parts of water, in a colloid mill and homogenization, preliminary grinding, subsequent grinding in a bead mill and spraying the suspension thus obtained in a scrubber with a mono nozzle and drying.

B. Biological examples.

a) Method descriptions.

Vegetation tests.

During standard experiments, seeds of various biotypes (of different origins) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm filled with ordinary earth (clay sand) and covered with a layer of soil of about 1 cm. Depending on the conditions of mushrooms, sterile or non-sterile earth. Then the pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C) until application. The pots are sprayed with the mixtures/formulations according to the invention, the latest mixtures or separately applied components on a special laboratory surface. Application in the form of WG, WP, EC or other formulations or combinations of active ingredients is carried out at certain stages of plant growth. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses.

Approximately 3 weeks after application, an external assessment of the effect on the soil and/or plants was carried out on a scale of 0-100% compared to the untreated control group: 0%=no noticeable effect compared to the untreated control group; 100%=full action compared to the untreated control group.

- 15 042560 (Note: the concept of seeds also includes vegetative forms of reproduction, such as parts at once; abbreviations used: h light = hours duration of illumination, g

AB/ha=gram active substance per hectare, l/ha=liter per hectare, S=susceptible, R=resistant).

1) Action on weeds in the pre-emergence period: seeds of various biotypes (of different origin) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm, filled with ordinary soil (clay sand) and covered with a layer of soil of about 1 cm. Depending on the conditions of honey agaric sterile or non-sterile soil may be used. Then the pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C) until application. Pots at the seed/plant stage of BBCH 00-10 are sprayed with mixtures/formulations according to the invention, mixtures or separately applied components such as WG, WP, EC or other formulations, on a special laboratory surface. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated.

2) Action on weeds in the post-emergence period: seeds of various biotypes (of different origins) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm filled with ordinary soil (clay sand) and covered with a layer of soil of about 1 cm. Depending on the conditions of honey agaric sterile or non-sterile soil may be used. Then the pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C) until application. Pots at different stages of BBCH seeds/plants, between 11-25, i.e. as a rule, between two and three weeks after the start of cultivation, spray liquids with mixtures/formulations according to the invention, mixtures or separately applied components, such as WG, WP, EC or other formulations, on a special laboratory surface. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated.

3) Action on weeds in the pre-emergence period with and without the introduction of active ingredients: seeds of various biotypes (of different origin) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm, filled with ordinary soil (clay sand). Depending on the conditions of honey mushrooms, sterile or non-sterile earth can be used. Pots of seed for comparison or are treated at BBCH seed/plant stage 00-10, i.e. typically between two and three weeks after the start of cultivation, with spray liquids of mixtures/formulations according to the invention, mixtures or single applied components, such as WG, WP, EC or other compositions, on a special laboratory surface, or an equivalent amount of mixtures / compositions according to the invention, mixtures or separately applied components, such as WG, WP, EC or other formulations, are applied to the surface layer of the earth by about 1 cm. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated. Pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C).

4) Selective action in the pre-emergence period: seeds of various cultivated species (of different origins) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm filled with ordinary earth (clay sand) and covered with a soil layer of about 1 cm. Depending on the conditions of the experiment sterile or non-sterile soil may be used. Then the pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C) until application. Pots at the seed/plant stage of BBCH 00-10 are sprayed with mixtures/formulations according to the invention, mixtures or separately applied components such as WG, WP, EC or other formulations, on a special laboratory surface. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated.

5) Selective action in the post-emergence period: seeds of various cultivated species (of different origins) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm filled with ordinary earth (clay sand) and covered with a layer of soil of about 1 cm. Depending on the conditions of the experiment sterile or non-sterile soil may be used. Then the pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C) until application. Pots at different stages of BBCH seeds/plants, 11-32, i.e. typically between two and four weeks after the start of cultivation, are treated with spray liquids with mixtures/formulations according to the invention, mixtures or separately applied components, such as WG, WP , EC or other formulations, on a special laboratory surface. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated. Pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C).

6) Action on weeds when used before sowing: seeds of different biotypes (different origin) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm filled with ordinary earth (clay sand). Depending on the conditions of the experiment, sterile

- 16 042560 naya or non-sterile earth. The seed pots are sprayed with mixtures/compositions according to the invention, mixtures or separately applied components such as WG, WP, EC or other formulations, on a special laboratory surface. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After sowing, the pots are placed in greenhouses and, if necessary, fertilized and irrigated. Pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C).

7) Action on weeds in the pre- and post-emergence period under different cultivation conditions: Seeds of various biotypes (of different origin) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm, filled with ordinary soil (clay sand) and covered with a layer of soil of about 1 see Depending on the conditions of the experiment, sterile or non-sterile soil can be used. Then the pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C) until application. Pots at various seed/plant stages of BBCH 00-25 are sprayed with mixtures/formulations according to the invention, mixtures or separately applied components such as WG, WP, EC or other formulations, on a special laboratory surface. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated. Pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C). Irrigation, if necessary, may be different. At the same time, individual control groups provide water differentially, from a level above PWP (continuous wilting point) and up to the level of maximum soil capacity.

8) Action on weeds in the pre- and post-emergence period under different irrigation conditions: Seeds of various biotypes (of different origin) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm, filled with ordinary soil (clay sand) and covered with a soil layer of about 1 see Depending on the conditions of the experiment, sterile or non-sterile soil can be used. Then the pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C) until application. Pots at various seed/plant stages of BBCH 00-25 are sprayed with mixtures/formulations according to the invention, mixtures or separately applied components such as WG, WP, EC or other formulations, on a special laboratory surface. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated. Pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C). At the same time, different irrigation technologies are used in separate control groups. Irrigation is carried out either differentially above or below previously established levels (simulated sprinkling).

9) Action on weeds in the pre- and post-emergence period under different soil conditions: Seeds of different biotypes (of different origin) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm filled with ordinary soil and covered with a layer of soil of about 1 cm. For comparison herbicidal action plants were cultivated on various types of soil, from sandy soil to heavy clay soil and different content of organic matter. Depending on the experimental conditions, sterile or non-sterile cultivation soil can be used. Then the pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C) until application. Pots at various seed/plant stages of BBCH 00-25 are sprayed with mixtures/formulations according to the invention, mixtures or separately applied components such as WG, WP, EC or other formulations, on a special laboratory surface. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated. Pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C).

10) Action on weeds in the pre- and post-emergence period to control resistant weed-/weeds: seeds of different biotypes (of different origin) of weeds and weeds of biotypes with different mechanisms of resistance to different mechanisms of action are sown in a pot with a diameter of 8-13 cm, filled ordinary earth (clay sand, LSI; pH 7.4; % C org. 2.2) and cover with a layer of soil of about 1 cm. Depending on the conditions of the experiment, sterile or non-sterile earth can be used. The pots are then cultivated in a greenhouse (12-16 hours of light, day temperature about 23°C, night temperature about 15°C) until application. Pots at various seed/plant stages of BBCH 00-25 are sprayed with mixtures/formulations according to the invention, mixtures or separately applied components such as WG, WP, EC or other formulations, on a special laboratory surface. The amount of water used for spray application was 300 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated. Pots are cultivated in a greenhouse (12-16 hours of light, day temperature about 23°C, night temperature about 15°C).

11) Effect on weeds and selectivity of crops in the pre- and post-emergence period under different sowing conditions: seeds of various biotypes (of different origin) and cultivated species (origin) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm, filled with ordinary

- 17 042560 soil and cover with a layer of soil of about 0-5 cm. Depending on the conditions of the experiment, sterile or non-sterile earth can be used. Then the pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C) until application. Pots at various seed/plant stages of BBCH 00-25 are sprayed with mixtures/formulations according to the invention, mixtures or separately applied components such as WG, WP, EC or other formulations, on a special laboratory surface. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated. Pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C).

12) Action on weeds in the pre- and post-emergence period at different soil pH values: seeds of various biotypes (of different origin) of weeds and weeds of biotypes are sown in a pot with a diameter of 8-13 cm, filled with ordinary soil and covered with a layer of soil of about 1 cm. comparison of herbicidal action, the plants were cultivated on different types of soil, on ordinary soil (clay sand) with different pH values of 7.4 and 8.4. For a higher pH value, lime was mixed into the earth accordingly. Sterile or non-sterile soil may be used depending on the experimental conditions. The pots are then cultivated in a greenhouse (12-16 hours of light, daytime temperature 2022°C, night temperature 15-18°C) until application. Pots at various seed/plant stages of BBCH 00-10 are sprayed with mixtures/formulations according to the invention, mixtures or single components such as WG, WP, EC or other formulations, on a dedicated laboratory surface. The consumption of the amount of water when applied by spraying was 100-600 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated. Pots are cultivated in a greenhouse (12-16 hours of light, day temperature 20-22°C, night temperature 15-18°C).

Field test.

During field trials under natural conditions during normal field preparation and with natural or artificial infestation with harmful plants, before or after sowing of cultivated plants or before or after germination of harmful plants, apply the agent according to the invention, the latest mixtures or individual components and give a visual assessment after 4 weeks - 8 months after treatment compared to untreated fragments (small plots of land). At the same time, damage to cultivated plants and action against harmful plants are recorded in percentage terms, as well as other results of the corresponding subject of the experiment.

b) Results.

The following methods were used for the results.

Action on weeds in the pre-emergence period: seeds of different biotypes (of different origins) of weeds and weeds of biotypes are sown in an 8 cm pot filled with ordinary earth (clay sand; steamed) and covered with a soil layer of about 1 cm. The pots are then cultivated in a greenhouse (12 -16 hours of light, day temperature 20-22°C, night temperature 15-18°C) until application. Pots at seed stage BBCH 00-06 are sprayed with mixtures/formulations according to the invention, mixtures or separately applied components such as WG, WP, EC or other formulations, on a special laboratory surface. The amount of water used for spray application was 300 l/ha. After treatment, the plants are again placed in greenhouses and, if necessary, fertilized and irrigated.

The following abbreviations have been used.

ВВСН=ВВСН-code gives information about the morphological stage of plant development. The abbreviation officially means the Federal Biological Office, the Office for the Protection of Plant Variety and the Chemical Industry. A BBCH value of 00-10 indicates the stages of seed germination prior to emergence on the surface. A BBCH value of 11-25 denotes the stages of leaf development before the emergence of shoots (corresponding to the number of shoots or side shoots).

PE=application before planting on the soil; BBCH seeds/plants 00-10.

PO=application after emergence of green parts of plants; BBCH plants 11-25.

HRAC=International 'Herbicide Resistance Action Committee', which categorizes permitted active substances according to their mechanism of action (syn. 'Mode of Action'; MoA).

HRAC group A = acetyl coenzyme A carboxylase inhibitors (MoA: ACCase).

HRAC group B = acetolactate synthase inhibitors (MoA: ALS).

AS = active ingredient (relative to 100% active ingredient; syn. a.i. (eng.)). Dosage g AS/ha = application rate in grams of active ingredient per hectare.

The following biotypes of weeds and weeds were used in the tests.

ALOMY - sensitive (Alopecurus myosuroides) - sensitive to common herbicidal active ingredients.

ALOMY - resistant (Alopecurus myosuroides) - resistant to herbicidal active ingredients HRAC groups A and B; mixture of field-occurring populations with increased metabolic resistance (EMR) and Target Site Resistenz (TSR).

- 18 042560

LOLRI - sensitive (Lolium rigidum) - sensitive to common herbicidal active ingredients.

LOLRI - resistant (Lolium rigidum) - resistant to herbicidal active ingredients HRAC groups A and B; mixture of field-occurring populations with increased metabolic resistance (EMR) and Target Site Resistenz (TSR).

AVEFA (Avena fatua) - wild oat.

BROST (Bromus sterilis) - barren fire.

SORHA (Sorghum halepense) - Johnson grass.

BRSNW (Brassica napus) - winter rapeseed.

CENCY (Centaurea cyanus) - sunflower.

EMEAU (Emex australis) - emex.

GALAP (Gallium aparine) - tenacious bedstraw.

PAPRH (Papaver rhoeas) - common poppy.

RAPRA (Raphanus raphanistrum) - field radish.

VERHE (Veronica hederaefolia) - ivy-leaved veronica.

HORVS (Hordeum vulgare) - common barley.

TRZAS (Triticum aestivum) - summer wheat.

The actions of the herbicidal compositions according to the invention meet the stated requirements and thus solve the problem of improving the application profile of the herbicidal active ingredient 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (also obtaining a universally applicable solution relative to the required flow rate at a constant to increasing efficiency).

In general, the herbicidal results of the agent according to the invention, compared with the latest mixtures or single components, have a better effect on economically important mono- and dicotyledonous pests, synergistic herbicidal effects were calculated using 'Colby-Former (cp. S. R. Colby; Weeds 15 (1967) , 20-22).

Table 1

Dose in g AI/ha ALOMY Feelings. ALOMY LOLRI Feelings. LOLRI Stable AVEFA BROST PAPRH 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 500 95 95 95 94 80 75 95 isoxazolidinone cinmethylin 50 80 70 90 85 0 50 0 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 500+50 100 99 99 100 95 95 99 isoxazolidinone + Cinmethylin Measured by COLBY - 99 99 100 99 80 88 95 Synergy - 1 1 -1 1 15 8 4 Dose in g AI/ha VERHE EMEAU RAPRA BRSNW TRZAS HORVS 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 500 95 70 90 20 70 60 isoxazolidino And Cinmethylin 50 0 0 0 0 thirty thirty 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 500+50 98 95 95 20 80 95 isoxazolidino n + Cinmethylin Measured by COLBY - 95 70 90 20 72 20 Synergy - 3 25 5 0 1 23

- 19 042560

table 2

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST PAPRH 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 400 95 95 95 94 75 70 95 Cinmethylin 10 0 0 0 0 0 0 0 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 400+10 100 98 100 100 85 78 99 Measured by COLBY - 95 95 95 94 75 70 95 Synergy - 5 3 5 6 10 8 4 Dose in g AB/ha VERHE EMEAU RAPRA BRSNW TRZAS HORVS 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 400 95 70 80 20 60 60 Cinmethylin 10 0 0 0 0 0 0 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 400+10 97 70 80 thirty 80 95 Measured by COLBY - 95 70 80 20 60 60 Synergy - 2 0 0 10 20 35

Table 3

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST PAPRH 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 400 95 95 95 94 75 70 95 Cinmethylin 25 80 60 70 70 0 20 0 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 400+25 100 98 98 99 93 95 98 Measured by COLBY - 99 98 99 98 75 76 95 Synergy - 1 0 -1 1 18 19 3

- 20 042560

Dose in g AB/ha VERHE EMEAU RAPRA BRSNW TRZAS HORVS 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 400 95 70 80 20 60 60 Cinmethylin 25 0 0 0 0 0 0 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 400+25 98 75 80 20 80 75 Measured by COLBY - 95 70 80 20 60 60 Synergy - 3 5 0 0 20 15

Table 4

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST PAPRH 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 250 93 93 95 80 75 65 95 isoxazolidino And Cinmethylin 25 80 60 70 70 0 20 0 2-[(2,4dichlorophenyl)methyl]-4,4- 250+25 dimethyl-3isoxazolidino n + Cinmethylin 100 95 98 93 85 80 98 Measured by COLBY - 99 97 99 94 75 72 95 Synergy - 1 -2 -1 -1 10 8 h Dose in g VERHE EMEAU RAPRA BRSNW TRZAS HORVS AB/ha 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 250 95 60 60 20 50 50 isoxazolidino And Cinmethylin 25 0 0 0 0 0 0 2-[(2,4dichlorophenyl)methyl]-4,4- 250+25 dimethyl-3isoxazolidino n + Cinmethylin 97 65 80 10 40 70 Measured by COLBY - 95 60 60 20 50 50 Synergy - 2 5 20 -10 -10 20

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Table 5

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST SORHA 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 50 20 10 70 60 15 0 thirty Cinmethylin 500 100 100 100 100 70 100 100 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 50+500 100 100 100 100 85 100 95 Measured by COLBY - 100 100 100 100 75 100 100 Synergy 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone Cinmethylin 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin Dose in g AI/ha 50 500 50+500 0 CENCY 10 80 70 0 VERHE 70 0 97 0 EMEAU 10 0 40 0 RAPRA 20 40 60 AND BRSNW 0 10 50 0 TRZAS 0 90 80 -5 HORVS 5 70 90 Measured by COLBY - 82 70 10 52 10 90 72 Synergy - -12 27 thirty 8 40 -10 19

Table 6

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST SORHA 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 25 0 0 thirty 5 5 0 0 Cinmethylin 250 100 90 100 100 50 100 80 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 25+250 100 100 100 100 75 100 90 Measured by COLBY - 100 90 100 100 53 100 80 Synergy - 0 10 0 0 23 0 10

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Dose in g AB/ha CENCY VERHE EAU RAPRA BRSNW TRZAS HORVS 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 25 0 40 0 5 0 0 2 Cinmethylin 250 thirty 0 0 thirty 0 75 65 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 25+250 90 95 40 40 20 75 75 Measured by COLBY - thirty 40 0 34 0 75 66 Synergy - 60 55 40 7 20 0 9

Table 7

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST SORHA 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 10 0 0 0 0 0 0 0 Cinmethylin 500 100 100 100 100 70 100 100 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 10+500 100 100 100 100 80 100 100 Measured by COLBY - 100 100 100 100 70 100 100 Synergy 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone Cinmethylin 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin Dose in g AI/ha 10 500 10+500 0 CENCY 0 80 90 0 VERHE 15 0 90 0 EMEAU 0 0 0 0 RAPRA 0 40 40 10 BRSNW 0 10 15 0 TRZAS 0 90 90 0 HORVS 0 70 95 Measured by COLBY - 80 15 0 40 10 90 70 Synergy - 10 75 0 0 5 0 25

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Table 8

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST SORHA 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 10 0 0 0 0 0 0 0 isoxazolidinone Cinmethylin 250 100 90 100 100 50 100 80 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 10+250 100 100 100 100 65 100 90 isoxazolidinone + Cinmethylin Measured by COLBY 100 90 100 100 50 100 80 Synergy Dose in g 0 10 0 0 15 0 10 CENCY VERHE EMEAU RAPRA BRSNW TRZAS HORVS AB/ha 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3 - 10 0 15 0 0 0 0 0 isoxazolidinone Cinmethylin 250 thirty 0 0 thirty 0 75 65 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3 - 10+250 90 50 0 thirty 15 65 95 isoxazolidinone + Cinmethylin Measured by COLBY - thirty 15 0 thirty 0 75 65 Synergy - 60 35 0 0 15 -10 thirty

Table 9

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST SORHA 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 10 0 0 0 0 0 0 0 Cinmethylin 100 90 70 100 100 25 100 70 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 10+100 100 100 100 100 25 100 85 Measured by COLBY - 90 70 100 100 25 100 70 Synergy - 10 thirty 0 0 0 0 15

- 24 042560

Dose in g AB/ha CENCY VERHE EMEAU RAPRA BRSNW TRZAS HORVS 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 10 0 15 0 0 0 0 0 Cinmethylin 100 0 0 0 0 0 40 40 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 10+100 93 10 0 thirty 15 40 50 Measured by COLBY - 0 15 0 0 0 40 40 Synergy - 93 -5 0 thirty 15 0 10

Table 10

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST SORHA 2-[(2,4dichlorophenyl)methyl]-4,4- 100 60 60 70 70 50 20 40 dimethyl-3- isoxazolidinone cinmethylin 100 90 70 100 100 25 100 70 2-((2,4dichlorophenyl)methyl]-4,4dimethyl-3- 100+10 100 99 100 100 80 95 100 isoxazolidinone + 0 Cinmethylin Measured by COLBY - 96 88 100 100 63 100 82 Synergy Dose in g 4 AND 0 0 18 -5 18 CENCY VERHE EMEAU RAPRA BRSNW TRZAS HORVS AB/ha 2-((2,4dichlorophenyl)methyl]-4,4dimethyl-3- 100 70 80 20 40 0 5 15 isoxazolidinone Cinmethylin 100 0 0 0 0 0 40 40 2-((2,4dichlorophenyl)methyl]-4,4dimethyl-3- 100+100 88 100 60 60 thirty 20 65 isoxazolidinone + Cinmethylin Measured by COLBY - 70 80 20 40 0 43 49 Synergy - 18 20 40 20 thirty -23 16

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Table 11

Dose in g ALOMY ALOMY LOLRI LOLRI AVEFA BROST SORHA AB/ha Feelings. Stable Feelings. Stable 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 200 95 80 90 80 70 thirty 60 isoxazolidinone Cinmethylin 100 90 70 100 100 25 100 70 2-[(2,4- dichlorophenyl)methyl]-4,4- 200+10 dimethyl-3 isoxazolidinone + Cinmethylin 0 100 99 100 100 75 96 95 Measured by COLBY - 100 94 100 100 78 100 88 Synergy Dose in g 1 5 0 0 -3 -4 7 CENCY VERHE EMEAU RAPRA BRSNW TRZAS HORVS AB/ha 2-[(2,4- dichlorophenyl)methyl]-4,4dimethyl-3- 200 88 90 40 50 5 40 40 isoxazolidinone Cinmethylin 100 0 0 0 0 0 40 40 2-[(2,4- dichlorophenyl)methyl]-4,4- 200+10 dimethyl-3 isoxazolidinone + Cinmethylin 0 95 99 80 60 20 50 70 Measured by COLBY - 88 90 40 50 5 64 64 Synergy - 7 9 40 10 15 -14 6

Table 12

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST SORHA 2-[(2,4- dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 100 60 60 70 70 50 20 40 Cinmethylin 50 80 70 90 85 0 50 65 2-[(2,4- dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 100+50 100 100 97 100 70 93 90 Measured by COLBY - 92 88 97 96 50 60 79 Synergy - 8 12 0 5 20 33 AND

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Dose in g AB/ha CENCY VERHE EMEAU RAPRA BRSNW TRZAS HORVS 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 100 70 80 20 40 0 5 15 Cinmethylin 50 0 0 0 0 0 thirty thirty 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin 100+50 85 98 60 50 20 thirty thirty Measured by COLBY - 70 80 20 40 0 34 41 Synergy - 15 18 40 10 20 -4 -AND

Table 13

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST SORHA 2-[(2,4dichlorophenyl)methyl]-4,4- 50 20 20 70 thirty 15 0 thirty dimethyl-3- isoxazolidinone Cinmethylin 100 90 70 100 100 25 100 70 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 50+100 100 100 100 100 70 90 90 isoxazolidinone + Cinmethylin Measured by COLBY - 92 76 100 100 36 100 79 Synergy Dose in g 8 24 0 0 34 -10 AND CENCY VERHE EMEAU RAPRA BRSNW TRZAS HORVS AB/ha 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 50 10 70 10 20 0 0 5 isoxazolidinone Cinmethylin 100 0 0 0 0 0 40 40 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- 50+100 85 100 60 40 20 20 25 isoxazolidinone + Cinmethylin Measured by COLBY - 10 70 10 20 0 40 43 Synergy - 75 thirty 50 20 20 -20 -18

- 27 042560

Table 14

2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone Cinmethylin Mefenpyr 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin + Mefenpyr Measured by COLBY Synergism Dose in g AI/ha 100 50 300 100+ 50+ 300 Dose in g AI/ha ALOMY Feelings. 60 80 0 100 92 8 CENCY ALOMY 60 70 0 90 88 2 VERHE LOLRI Feelings. 70 90 0 98 97 1 EMEAU LOLRI Stable 75 100 0 100 100 0 RAPRA AVEFA 50 0 0 55 50 5 BRSNW BROST 20 50 0 90 60 thirty TRZAS SORHA 40 65 0 80 79 1 HORVS 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 100 70 80 20 40 0 5 15 Cinmethylin 50 0 0 0 0 0 thirty thirty mefenpir 300 0 0 0 0 0 0 0 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin + Mefenpyr 100+ 50+ 300 70 97 75 85 10 0 5 Measured by COLBY - 70 80 20 40 0 34 41 Synergy - 0 17 55 45 10 -34 -36

Table 15

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST SORHA 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 100 60 60 70 75 50 20 40 Cinmethylin 50 80 70 90 100 0 50 65 mefenpir 100 0 0 0 0 0 0 0 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin + Mefenpyr 100+ 50+ 100 99 95 95 99 60 90 80 Measured by COLBY - 92 88 97 100 50 60 79 Synergy - 7 7 -2 -1 10 thirty 1

- 28 042560

Dose in g AB/ha CENCY VERHE EMEAU RAPRA BRSNW TRZAS HORVS 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 100 70 80 20 40 0 5 15 Cinmethylin 50 0 0 0 0 0 thirty thirty mefenpir 100 0 0 0 0 0 0 0 2-[(2,4- dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin + Mefenpyr 100+ 50+ 100 99 97 75 90 5 5 10 Measured by COLBY - 70 80 20 40 0 34 41 Synergy - 29 17 55 50 5 -29 -31

Table 16

Dose in g AB/ha ALOMY Feelings. ALOMY Stable LOLRI Feelings. LOLRI Stable AVEFA BROST SORHA 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone 100 60 60 70 75 50 20 40 Cinmethylin 50 80 70 90 100 0 50 65 mefenpir 10 0 0 0 0 0 0 0 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin + Mefenpyr 100+ 50+ 10 100 100 100 100 60 70 98 Measured by COLBY - 92 88 97 100 50 60 79 Synergy - 8 12 3 0 10 10 19 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone Cinmethylin Mefenpyr 2-[(2,4dichlorophenyl)methyl]-4,4dimethyl-3- isoxazolidinone + Cinmethylin + Mefenpyr Tsoza in g AB/ha 100 50 10 100+ 50+ 10 CENCY 70 0 0 93 VERHE 80 0 0 97 EMEAU 20 0 0 75 RAPRA 40 0 0 50 BRSNW 0 0 0 5 TRZAS 5 30 0 5 HORVS 15 30 0 20 Measured by COLBY - 70 80 20 40 0 34 41 Synergy - 23 17 55 10 5 -29 -21

- 29 042560

Claims (10)

1. Herbicide mixture containing i) 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone; and ii) cinmethylin, wherein the herbicidal components have the following weight ratio to each other: (component i range): (range component ii) - (1-100):(1-100). 2. Herbicide mixture according to claim 1, additionally containing at least one protective agent, the application rate being generally 5-2000 g AS/ha, preferably 10-500 g AS/ha and particularly preferably 10-300 g AS / ha. 3. Herbicide mixture according to claim 2, containing at least one protective agent from the group consisting of cloquintoset-mexil, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl. 4. Herbicidal mixture according to one of claims 1 to 3, wherein the herbicidal components have the following mass ratio to each other: (component range 1):(component range ii) - (1-50):(1-50). 5. Herbicide mixture according to one of claims 1 to 4, containing for the respective herbicide components the following application rates: component i): in general 1-2000 g AS/ha, preferably 10-1000 g AS/ha, particularly preferably 10-500 g AS/ha 2-[(2,4-dichlorophenyl)methyl]-4,4- dimethyl-3-isoxazolidinone; component ii): in general 1-2000 g AS/ha, preferably 10-1000 g AS/ha, particularly preferably 10-500 g AS/ha cinmethylin. 6. Herbicide mixture according to one of claims 1 to 5, additionally containing additives and/or formulation auxiliaries conventional in the field of plant protection. 7. A method for controlling unwanted plant growth, wherein the herbicidal mixture according to one of claims 1 to 6 is applied to plants, parts of plants, plant seeds or areas where plants grow. 8. The method according to claim 7 for the selective control of harmful plants in crops of useful plants. 9. The method of claim 8, wherein the plant cultures are genetically modified or obtained by mutation selection. 10. The use of a herbicidal mixture according to one of claims 1 to 6 for controlling harmful plants in crops of useful plants.