EP3823450A1

EP3823450A1 - Herbicidal mixtures containing aclonifen and cinmethylin

Info

Publication number: EP3823450A1
Application number: EP19742325.4A
Authority: EP
Inventors: Thomas Auler; Udo Bickers; Hubert Menne; Christoph BREITENSTRÖTER; Herve TOSSENS
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 2018-07-16
Filing date: 2019-07-12
Publication date: 2021-05-26
Also published as: BR112021000056A2; AU2019307127A1; AR115791A1; CL2021000125A1; CN112469277A; WO2020016134A1; US20210289781A1; JP2021529820A

Abstract

The invention relates to herbicidal mixtures containing i) aclonifen and ii) cinmethylin, as well as to herbicidal compositions containing said mixtures. The invention further relates to a process for synthesizing said herbicidal mixtures and compositions containing said mixtures. The invention finally relates to the use of said mixtures and compositions in the agricultural field for controlling harmful plants.

Description

HERBICIDE MIXTURES CONTAINING ACLONIFEN AND

cinmethylin

The present invention relates to herbicidal mixtures comprising i) aclonifene and ii) cinmethylin and herbicidal compositions comprising these mixtures. The present invention further relates to a process for the preparation of these herbicidal mixtures and compositions comprising these mixtures. Furthermore, the invention relates to the use of the mixtures and compositions mentioned in the field of agriculture for controlling harmful plants.

Aclonifen is already known as a selective herbicide from DE2831262.

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 effectiveness of Aclonifen as a single active ingredient and in the known mixtures, there is still a need to improve the application profile of this active ingredient. There are many reasons for this, e.g. further increase in effectiveness in special areas of application, increase in crop tolerance, reaction to new production techniques in individual crops and / or to the increasing occurrence of herbicide-resistant harmful plants.

One way to improve the application profile of a herbicide is to combine the active ingredient with one or more suitable other active ingredients. However, phenomena of chemical, physical and biological incompatibility often occur when several active ingredients are used in combination, for example poor stability in a co-formulation, decomposition of an active ingredient or antagonism of the active ingredients. On the other hand, combinations of active ingredients with a favorable activity profile, high stability and, as far as possible, synergistically enhanced action are desired, which allow a reduction in the application rate compared to the individual application of the active ingredients to be combined. Combinations of active ingredients which generally increase the tolerance of crop plants and / or which can be used in special production techniques are also desirable. This includes, for example, a reduction in the sowing depth, which often cannot be used for reasons of cultural compatibility. This generally leads to a faster emergence of the culture, reduces its risk of emergence diseases (such as Pythium and Rhizoctonia), improves the ability to overwinter and the degree of tillering. This also applies to late seeds, which would otherwise not be possible due to the cultural compatibility risk. The object of the present invention was to improve the application profile of the herbicidal active ingredient aclonifene with a view to:

- a simplified application process, which would reduce the costs for the user and would therefore have a gentler impact on the environment;

- An improvement in the application flexibility of the active ingredients from pre-emergence to

Post-emergence of crops and weeds;

- an improvement in the application flexibility of the active ingredients, which would make application possible before sowing the crop;

- an improvement and application flexibility of the effectiveness on soils with different soil properties (e.g. soil type, soil moisture);

- an improvement and application flexibility of effectiveness in different

Irrigation methods (rain events);

- An improvement in the effectiveness of weed plants from different

Germinate soil depths;

- Improvement and application flexibility on soils with different pH values;

- An improvement in the effectiveness of resistant weed plant species, which is a new

Would enable effective resistance management,

- an improvement in effectiveness due to synergism, with the latter task being particularly important.

This problem was solved by providing a herbicide mixture containing aclonifene and the further herbicide cinmethylin.

The invention thus relates to herbicide mixtures comprising i) aclonifene and ii) cinmethylin.

Another aspect of the present invention is a herbicide mixture which, in addition to components i) and ii), comprises at least one further herbicide from group I. Another aspect of the present invention is a herbicide mixture which, in addition to components i) and ii), comprises at least one safener.

Another aspect of the present invention is a herbicide mixture which, in addition to components i) and ii), comprises at least one further herbicide from group I and a safener.

definitions

Group I herbicides:

2 - [(2,4-dichlorophenyl) methyl] -4,4-dimethyl-3-isoxazolidinone, acetochlor, acifluorfen, acifluorfen-sodium, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4 -amino-3-chloro-6- (4-chloro-2-fluoro-3-methylphenyl) -5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos-sodium, bispanibibacac, sodium, bispanibosac, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, chlorfamone, carf , chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorosulfuron, cinidon, cinidon-ethyl, cinosulfuron, clacyfos, clafopin, clafopin, clethodop, clodopod, clethodop, clodopod, clethodop, , clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, 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-DB-butyl, -dimethylammonium, isooctyl, potassium and sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2- (2,4-dichlorobenzyl) -4,4-dimethyl- 1, 2-oxazolidin-3-one, 2- (2,5-dichlorobenzyl) -4,4-dimethyl-1, 2-oxazolidin-3-one, dichloroprop, dichloroprop-P, diclo fop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, diterbatamid, dinitramine, dinitramine, dititaminophen dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethamet-sulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F- 5231, ie N- [2-chloro- 4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] phenyl] ethanesulfonamide, F-7967, ie 3- [7-chloro -5-fluoro-2- (trifluoromethyl) -lH-benzimidazol-4-yl] -l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (lH, 3H) -dione, fenoxaprop, fenoxaprop-P, fenoxaprop- ethyl, fenoxaprop-P- ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M- methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsacam, flumiclorum, flumiclorum, flumicloracyl, flumicloro, flumicloro, flumicloro, flumicloro, flumiclor, flumicloro fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flutyruthetham, fluthyrethamethane, flutyruthuth-meptyl, fleutroputh-meptyl, flutroputh-meptyl, flutroputh-meptyl, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, --dimethylammonium -sodium and -trimesium, H-9201, ie 0- (2,4-dimethyl-6-nitrophenyl) -0-ethyl-isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P , haloxyf op-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, ie l- (dimethoxyphosphoryl) ethyl- (2,4-dichlorophenoxy) acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuronox, iodosulfuronoxinililoxyliloxane -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutilate, KUH-043, ie 3 - ({[5- (difluoromethyl) -l-methyl-3- (trifluoromethyl) -lH-pyrazol-4-yl ] methyl} sulfonyl) -5,5-dimethyl-4,5-dihydro-l, 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 -potas sium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, met isobromocyanurol, metol , metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, ie N- [3-chloro-4- (l-methylethyl) - phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC- 310, ie 4- (2,4-dichlorobenzoyl) -l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, prulfiluron, prisulfuron, primis ofoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, Propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron - ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfurazine, simethoximazine, safethoxynacyl SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron,, SYN-523, SYP-249, ie l-ethoxy-3-methyl-l-oxobut-3-en-2-yl- 5- [2 -chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP-300, ie l- [7-fluoro-3-oxo-4- (prop-2-in-l-yl) -3,4-dihydro -2H- 1,4-benzoxazin-6-yl] -3-propyl-2-thioxoimidazolidin-4,5-dione, 2,3,6-TB A, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyrali sulfate, toamone zoneamone, oxamone tribenuron, tribenuron-methyl, triclopy r, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, tifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea Sulfate, vernolate, XDE-848, ZJ-0862, ie 3,4-dichloro-N- {2- [4 , 6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following compounds:

Examples of plant growth regulators as possible mix partners are:

Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3- (cycloprop-l-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, and mono (N, N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA ), 4- indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2- (l-naphthyl) acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4 [(2-phenylethyl) amino] butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, Salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

herbicides:

The herbicides mentioned in this description are, for example, from "The Pesticide Manual", 16.

Edition 2012 known.

safener:

The following groups of compounds can be considered as safeners, for example:

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

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

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

Sl ^b ) derivatives of dichlorophenylpyrazole carboxylic acid (Sl ^b ), preferably compounds such as

1 - (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylic acid ethyl ester (S 1 -2), l- (2,4-dichlorophenyl) -5-isopropylpyrazole-3-carboxylic acid ethyl ester (S 1-3), l- (2,4-dichlorophenyl) -5- (l, l-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (S1-4) and related compounds as described in EP-A-333 131 and EP-A-269 806 are;

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

Sl ^d ) compounds of the triazole carboxylic acid type (Sl ^d ), preferably compounds such as

Fenchlorazole (ethyl ester), i.e. 1- (2,4-dichlorophenyl) -5-trichloromethyl- (lH) -l, 2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds, as described in EP-A-174 562 and EP -A-346 620 are described;

Sl ^e ) compounds of the type of 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid, or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl ^e ), preferably compounds such as 5- ( 2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (S 1-8) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S 1-9) and related compounds, as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid (Sl- 10) or 5,5-Diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sl-11) ("Isoxadifen-ethyl") or -n-propyl ester (Sl-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-quinoline oxy-derivatives (S2):

S2 ^a ) Compounds of the 8-quinolineoxyacetic acid (S2 ^a ) type, preferably (5-chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5- Chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-but-l-yl) ester (S2-2),

(5-chloro-8-quinolinoxy) 4-allyl-oxy-butyl acetate (S2-3),

(5-chloro-8-quinolinoxy) acetic acid-l-allyloxy-prop-2-yl ester (S2-4),

(5-chloro-8-quinolinoxy) ethyl acetate (S2-5),

(5-chloro-8-quinolinoxy) methyl acetate (S2-6),

(5-chloro-8-quinolinoxy) allyl acetate (S2-7),

(5-chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -l-ethyl ester (S2-8),

(5-Chloro-8-quinolinoxy) 2-oxo-prop-1-yl acetate (S2-9) and related compounds as described in EP-A-86 750, EP-A-94 349 and EP-A- 191 736 or EP-A-0 492 366 are described, and (5-chloro-8-quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium , Aluminum, iron, ammonium, quaternary ammonium, sulfonium, or phosphonium salts as described in WO-A-2002/34048;

S2 ^b ) Compounds of the type of (5-chloro-8-quinolinoxy) malonic acid (S2 ^b ), preferably

Compounds such as (5-chloro-8-quinolinoxy) diethyl malonate,

(5-chloro-8-quinolinoxy) malonate,

Methyl (5-chloro-8-quinolinoxy) malonic acid and related compounds as described in EP-A-0 582 198.

S3) Active substances of the type of dichloroacetamide (S3), often as pre-emergence safeners

(Soil-effective safeners), such as B.

"Dichlormid" (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-l-oxa-3-aza-spiro [4,5] decane) from the company

Nitrokemia or Monsanto (S3-7),

"TI-35" (1-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8), "Diclonon" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9)

((RS) -l-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [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 its (R) -isomer (S3-11).

S4) compounds from the class of the acylsulfonamides (S4): S4 ^a ) N-acylsulfonamides of the formula (S4 ^a ) and their salts as described in WO-A-97/45016,

RA ¹ (Ci-Ce) alkyl, (C3-Ce) cycloalkyl, the latter 2 radicals being substituted by V _A substituents from the group halogen, (Ci-C alkoxy, (Ci-Ce) haloalkoxy and (Ci-C4) alkylthio and in the case of cyclic radicals also substituted by (Ci-C alkyl and (Ci-C haloalkyl;

RA ² halogen, (C ₁ -C ₄ ) alkyl, (Ci-C ₄ ) alkoxy, CF _3; m _A 1 or 2;

V _A is 0, 1, 2 or 3;

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

wherein RB ¹ , RB ² independently of one another hydrogen, (Ci-Ce) alkyl, (C3-Ce) cycloalkyl, (C ₃ - Ce) alkenyl, (C3-C6) alkynyl,

RB ^{3 is} halogen, (Ci-C alkyl, (Ci-C4) haloalkyl or (Ci-C4) alkoxy and IP _B 1 or 2, for example those in which

RB ¹ = cyclopropyl, R _B ² = hydrogen and (RB ³ ) = 2-OMe ("Cyprosulfamide", S4-1),

R _B ¹ = cyclopropyl, R _B ² = hydrogen and (R _B ³ ) = 5-Cl-2-OMe is (S4-2),

R _B ¹ = ethyl, R _B ² = hydrogen and (R _B ³ ) = 2-OMe is (S4-3),

R _B ¹ = isopropyl, R _B ² = hydrogen and (R _B ³ ) = 5-Cl-2-OMe is (S4-4) and

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

S4 ^C ) compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4 ^C ) as described in EP-A-365484,

where Rc ¹ , Rc ² independently of one another are hydrogen, (Ci-Cs) alkyl, ((VCsK'ycloalkyl, (C ₃ -

Ce) alkenyl, (C3-C6) alkynyl,

Rc ^{3 is} halogen, (Ci-C4) alkyl, (Ci-C4) alkoxy, CF ₃ and mc 1 or 2; for example 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,

l- [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,

l- [4- (N-4,5-Dimethylbenzoylsulfamoyl) phenyl] -3-methyl urea;

S4 ^d ) compounds of the N-phenylsulfonylterephthalamide type of the formula (S4 ^d ) and their salts, which are known, for example, from CN 101838227, wherein

R _D ⁴ halogen, (Ci-C4) alkyl, (Ci-C4) alkoxy, CF _3; m _D 1 or 2;

R _D ⁵ hydrogen, (Ci-Ce) alkyl, (C3-Ce) cycloalkyl, (C2-Ce) alkenyl, (C2-C6) alkynyl, (Cs-

Ce) means cycloalkenyl.

S5) Active ingredients from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), e.g. 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A- 2004/084631, WO-A-2005/015994, WO-A-2005/016001.

S6) active substances from the class of 1,2-dihydroquinoxalin-2-one (S6), e.g. l-methyl-3- (2-thienyl) -1, 2-dihydroquinoxalin-2-one, l-methyl-3- (2-thienyl) -1, 2-dihydroquinoxalin-2-thione, l- (2-aminoethyl ) -3- (2-thienyl) -l, 2-dihydroquinoxalin-2-one hydrochloride, l- (2-

Methylsulfonylaminoethyl) -3- (2-thienyl) -1, 2-dihydro-quinoxalin-2-one, as described in WO-A-2005/112630.

S7) compounds from the class of diphenylmethoxyacetic acid derivatives (S7), e.g.

Diphenylmethoxyacetic acid methyl ester (CAS Reg. No. 41858-19-9) (S7-1),

Diphenylmethoxyacetic acid ethyl ester or Diphenylmethoxyacetic acid as described in WO-A-98/38856.

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

where the symbols and indices have the following meanings:

R _D ¹ is halogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy, R _D ² is hydrogen or (C ₁ -C ₄ ) alkyl,

R _D ³ is hydrogen, (Ci-C ₈ ) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, each of the abovementioned C-containing radicals being unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted; or their salts is an integer from 0 to 2.

S9) active substances from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.

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

S 10) compounds of the formulas (S 10 ^a ) or (S 10 ^b ) as described in WO-A-2007/023719 and WO-A-2007/023764,

wherein

RE ¹ halogen, (Ci-C4) alkyl, methoxy, nitro, cyano, CF ₃ , OCF ₃

Y _E , _E independently of one another O or S, P _E an integer from 0 to 4,

R _E ² (Ci-Ci ₆ ) alkyl, (C2-Ce) alkenyl, (C3-Ce) cycloalkyl, aryl; Benzyl, halobenzyl,

R _E ^{3 is} hydrogen or (Ci-C ₆ ) alkyl.

Si l) active substances of the type of oxyimino compounds (Si l), which are known as seed dressings, such as. B. "Oxabetrinil" ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl l-1), which as

Seed dressing safener known for millet against damage from metolachlor

"Fluxofenim" (1 - (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-0- (1, 3-dioxolan-2-ylmethyl) oxime)

(S 11-2), which is known as a seed dressing safener for millet against damage to metolachlor, and "Cyometrinil" or "CGA-43089" ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S 11-3), which is known as a seed dressing safener for millet against damage to metolachlor. ) Active substances from the class of the isothiochromanones (S12), such as methyl - [(3-oxo-lH-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361. ) One or more connections from group (S 13):

"Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,

"Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice,

"Flurazole" (Benzyl-2-chloro-4-trifluoromethyl-l, 3-thiazole-5-carboxylate) (S13-3), which as

Seed dressing safener known for millet against damage from alachlor and metolachlor

"CF 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which as Safener for corn against damage from imidazolinones is known

"MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn,

"MG 838" (CAS Reg. No. 133993-74-5) (2-propenyl l-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia

"Disulfoton" (O, O-Diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),

"Dietholate" (O, O-Diethyl-O-phenylphosphorothioat) (S13-8),

"Mephenate" (4-chlorophenyl methyl carbamate) (S13-9). ) Active substances which, in addition to a herbicidal action against harmful plants, also have safener action on crop plants such as rice, such as, for. B. "Dimepiperate" or "MY-93" (.V-1-methyl-1-phenylethyl-piperidine-1-carbothioate), which is known as a safener for rice against damage to the herbicide Molinate,

"Daimuron" or "SK 23" (l- (l-methyl-l-phenylethyl) -3-p-tolylurea), which is known as a safener for rice against damage to the herbicide imazosulfuron, "Cumyluron" = "JC-940" (3- (2-chlorophenylmethyl) -l- (l-methyl-l-phenyl-ethyl) urea, see JP-A-60087254), which acts as a safener for rice against damage to some herbicides is known

"Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxy-benzophenone), which is known as a safener for rice against damage by some herbicides,

"COD" (l-bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage to some herbicides in rice.

S 15) compounds of the formula (S 15) or their tautomers,

as described in WO-A-2008/131861 and WO-A-2008/131860, in which

RH ^{1 represents} a (Ci-C ₆ ) haloalkyl radical and RH ^{2 represents} hydrogen or halogen and

RH ³ , RH ⁴ independently of one another are hydrogen, (Ci-Cie) alkyl, (C2-Ci6) alkenyl or (C2-Ci6) alkynyl, each of the last 3 radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, Cyano, (Cj-C alkoxy, (Cj-C haloalkoxy, (Cj-C alkylthio, (Cj-C alkylamino, di [(Cj-C4) alkyl] amino, [(Ci-C alkoxy] carbonyl, [( Cj-C HaloalkoxyJ-carbonyl, (C3-Ce) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, or (C3-C6) cycloalkyl, (C4 -C6) cycloalkenyl, (C3-C6) cycloalkyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6) cycloalkenyl which is bonded on one side of the ring with a 4th to 6-membered saturated or unsaturated carbocyclic ring, each of the latter 4 radicals being unsubstituted or by one or more R este from the group halogen, hydroxy, cyano, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy, (Ci-C4) alkylthio, (Ci-C4) Alkylamino, di [(Ci C alkylj-amino, [(Ci-C alkoxyj-carbonyl, [(Ci-C4) haloalkoxy] carbonyl,

(C3-C6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted is substituted or

RH ^{3 is} (Ci-C-alkoxy, (Cz-C alkenyloxy, (C2-C6) alkynyloxy or (C2-C4) haloalkoxy) and RH ^{4 is} hydrogen or (Ci-C4) -alkyl or

RH ³ and RH ⁴ together with the directly bound N atom form a four- to eight-membered heterocyclic ring which, in addition to the N atom, can also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy and (Ci-C4) alkylthio is means.

S16) Active ingredients which are primarily used as herbicides, but also have safener action on crops, for. B.

(2,4-dichlorophenoxy) acetic acid (2,4-D), (4-chlorophenoxy) acetic acid, (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop), 4- (2 , 4-dichlorophenoxy) butyric acid (2,4-DB), (4-chloro-o-tolyloxyacetic acid (MCPA), 4- (4-chloro-o-tolyloxy) butyric acid, 4- (4-chlorophenoxy) butyric acid, 3 , 6-dichloro-2-methoxybenzoic acid (Dicamba), 1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloroethyl).

Preferred safeners are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole-ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron.

Particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

Mefenpyr-diethyl is very particularly preferred.

AS / ha:

Insofar as the abbreviation "AS / ha" is used in this description, this means "active substance per hectare", based on 100% active ingredient. All percentages in the description are percentages by weight (abbreviation: "% by weight") and refer to unless otherwise defined, on the relative weight of the respective component based on the total weight of the herbicidal mixture / composition (for example as a formulation).

Cinmethylin (CAS RN 87818-31-3) is a racemic mixture of (+/-) - 2-exo- (2-methylbenzyloxy) - l-methyl-4-isopropyl-7-oxabicyclo [2. 2.1] heptane.

The ratio of the two enantiomers to one another is approximately the same. The preparation of the enantiomerically enriched compounds is known from EP 0 081 893 Al.

The herbicidal compositions according to the invention have the components according to the invention of the mixture i), ii) and, if appropriate, further herbicides and safeners, and contain further constituents, e.g. agrochemical active ingredients from the group of insecticides and fungicides and / or additives and / or formulation auxiliaries customary in crop protection.

In a preferred embodiment, the herbicidal mixtures / compositions according to the invention have synergistic effects as an improvement in the application profile. These synergistic effects can e.g. can be observed when the herbicide components are applied together, but they can often also be found with a delayed application (splitting). It is also possible to use the individual herbicides or the herbicide combinations in several portions (sequence application), e.g. Pre-emergence applications, followed by post-emergence applications or early post-emergence applications, followed by mid or late post-emergence applications. Preferred here is the simultaneous or prompt application of the active compounds of the herbicidal mixtures / compositions according to the invention.

The synergistic effects allow a reduction in the application rates of the individual active ingredients, a higher potency with the same application rate, the control of previously unrecognized types (gaps), an extension of the application period and / or a reduction in the number of necessary individual applications and - as a result for the user - economically and more environmentally friendly weed control systems.

The application rate of the herbicide components in the herbicidal mixtures / compositions can vary within wide limits. For applications with application rates of 1 to 5000 g AS / ha Herbicide components are combated in the pre- and post-emergence process, a relatively wide range of annual and perennial weeds, grasses and cyperaceae.

The application rates of the herbicide components in the mixtures / compositions are in the weight ratio to one another given below: i): h) in general (1-1000) :( 1-1000), preferably (1-100) :( 1-100), particularly preferred (1-50) :( 1-50).

The application rates of the respective herbicide components in the herbicidal mixtures / compositions are:

- Component i): generally 1 - 2000 g ai / ha, preferably 10 - 1000 g ai / ha, particularly preferably 10 - 500 g ai / ha aclonifen;

- Component ii): generally 1 - 2000 g ai / ha, preferably 10 - 1000 g ai / ha, particularly preferably 10 - 500 g ai / ha cinmethylin.

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

Correspondingly, the weight percentages (% by weight) of the herbicide components based on the total weight of the herbicidal compositions, which may also contain further constituents, can be calculated from the above application rates.

The mixtures / compositions according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Perennial harmful plants that are difficult to control and that sprout from rhizomes, rhizomes or other permanent organs are also well captured by the active ingredients.

The present invention therefore also relates to a process for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, the mixtures / compositions according to the invention applied to the plants (for example harmful plants such as mono- or dicotyledon weeds or undesired crop plants), the seed ( grains, seeds or vegetative propagation organs such as tubers or shoots with buds) or the area on which the plants grow (e.g. the area under cultivation). The mixtures / compositions according to the invention can be applied, for example, in the pre-sowing (possibly also by incorporation into the soil), pre-emergence or post-emergence methods. Some representatives of the monocotyledonous and dicotyledonous weed flora, which are caused by the mixtures / compositions according to the invention can be controlled without the name being intended to restrict them to certain types.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Festoochaistimist, Eriochaantimist, Eriochaimantherist, Eriochaimantherist , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum.

Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Gexhoris, Erysimum, Erysimum , Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senalsola , 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 germination, either weed seedlings are prevented from emerging completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks , This is also the case if the IBS (Incorporated By Sowing) application method is used. The herbicidal mixture / composition is introduced into the seedbed when sowing.

When the mixtures / compositions according to the invention are applied to the green parts of the plants in the post-emergence process, growth stops after the treatment and the harmful plants remain at the growth stage at the time of application or die completely after a certain time, so that weed competition which is harmful to the crop plants is in this way is removed very early and sustainably. The mixtures / compositions according to the invention can also be applied to the water in rice and are then taken up via the soil, shoots and roots.

The mixtures / compositions according to the invention are notable for a rapid onset and long-lasting herbicidal action. The rain resistance of the active ingredients in the mixtures / compositions according to the invention is generally favorable. A particular advantage is that the effective dosages of components i) and ii) used in the mixtures / compositions according to the invention can be set so low that their soil effect is optimally low. This makes their use not only possible in sensitive crops, but groundwater contamination is also practically avoided. Through the The combination of active substances according to the invention enables a considerable reduction in the necessary application rate of the active substances.

When components i) and ii) are used together in the mixtures / compositions according to the invention, in a preferred embodiment there are superadditive (= synergistic) effects as an improvement in the application profile. The effect in the combinations is stronger than the expected total of the effects of the individual herbicides used. The synergistic effects allow a higher and / or longer potency (long-term action); combating a broader spectrum of weeds, grasses and cyperaceae, sometimes with only one or a few applications; faster onset of herbicidal activity; Control of species not yet recorded (gaps); Control e.g. of species that are tolerant or resistant to one or more herbicides; Extension of the application period and / or a reduction in the number of individual applications required or a reduction in the total application rate and - as a result for the user - economically and ecologically more advantageous weed control systems.

The properties and advantages mentioned are required in practical weed control in order to keep agricultural / forestry / horticultural crops, grassland / pasture land or crops for energy production (biogas, bio-ethanol) free from undesired competitive plants and thus to secure the yields qualitatively and quantitatively and / or to increase. The technical standard is significantly exceeded by these new combinations in the herbicidal mixtures / compositions according to the invention with regard to the properties described.

Although the mixtures / compositions according to the invention have excellent herbicidal activity against mono- and dicotyledon weeds, crop plants of economically important crops e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the Ganasyp , Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, depending on the structure of the respective compound according to the invention and its application rate only insignificantly or not at all.

In addition, the mixtures / compositions according to the invention can in some cases have growth-regulating properties in the crop plants. They intervene regulating the plant's own metabolism and can therefore be used to influence plant constituents in a targeted manner and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. A Inhibition of vegetative growth plays a major role in many mono- and dicotyledon crops, since harvest losses during storage can be reduced or completely prevented.

Because of their improved application profile, the mixtures / compositions according to the invention can also be used to control harmful plants in known plant crops or tolerant or genetically modified crop and energy plants which are still to be developed. The transgenic plants (GMOs) are generally distinguished by particularly advantageous properties, for example resistance to certain pesticides, especially certain herbicides (such as resistance to components i) and ii) in the mixtures / compositions according to the invention, for example by Resistance to insect pests, plant diseases or pathogens such as certain microorganisms such as fungi, bacteria or viruses. Other special properties concern e.g. the crop in terms of quantity, quality, storability and the composition of special ingredients. Thus, transgenic plants with increased starch content or changed starch quality or those with a different fatty acid composition of the crop or increased vitamin content or energetic properties are known. Other special properties can include tolerance or resistance to abiotic stressors e.g. There is heat, cold, dryness, salt and ultraviolet radiation. Equally, the mixtures / compositions according to the invention, owing to their herbicidal and other properties, can also be used to control harmful plants in crops of known or still to be developed plants obtained by mutant selection, and also from crosses of mutagenic and transgenic plants.

Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants are, for example, classic breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be produced using genetic engineering processes (see, for example, EP 0221044 A, EP 0131624 A). For example, the following have been described in several cases: genetic engineering changes in crop plants for the purpose of modifying the starch synthesized in the plants (for example WO 92/011376 A, WO 92/014827 A, WO 91/019806 A); Transgenic crop plants which act against certain herbicides of the glufosinate type (cf., for example, EP 0242236 A, EP 0242246 A) or glyphosate (WO 92/000377 A) or the sulfonylureas (EP 0257993 A, US Pat. No. 5,013,659) or against combinations or mixtures of these herbicides “Gene stacking” are resistant, like transgenic crops B. corn or soy with the trade name or the designation Optimum ™ GAT ™ (Glyphosate ALS Tolerant); transgenic crop plants, for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP 0142924 A, EP 0193259 A); transgenic crop plants with modified fatty acid composition (WO 91/013972 A); genetically modified crops with new ingredients or secondary substances such as new phytoalexins, which have increased disease resistance cause (EP 0309862 A, EP 0464461 A); genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EP 0305398 A); transgenic crop plants that produce pharmaceutically or diagnostically important proteins (“molecular pharming”); transgenic crops characterized by higher yields or better quality; transgenic crop plants which are characterized by a combination of, for example, the above-mentioned new properties (“gene stacking”).

In principle, numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known; see e.g. I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg or Christou, "Trends in Plant Science" 1 (1996) 423-431). For such genetic engineering manipulations, nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard procedures e.g. Base exchanges made, partial sequences removed or natural or synthetic sequences added. Adapters or linkers can be attached to the fragments for connecting the DNA fragments to one another, 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 and Clones", VCH Weinheim 2nd edition 1996.

The production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the gene product mentioned above.

For this purpose, DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.

When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a specific compartment, the coding region can be linked, for example, to DNA sequences which ensure localization in a specific compartment. Such sequences are known to the person skilled in the art (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). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells.

The transgenic plant cells can be regenerated into whole plants using known techniques. The transgenic plants can in principle be plants of any plant species, i.e. both monocot and dicot plants. Thus, transgenic plants are available which have changed properties due to overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

The present invention furthermore also relates to a process for controlling unwanted vegetation (for example harmful plants), preferably in crops such as cereals (for example hard and soft wheat, barley, rye, oats, hybrids thereof such as triticale, planted or sown rice under 'upland' - or 'paddy' conditions, maize, millet such as sorghum), sugar beet, sugar cane, rapeseed, cotton, sunflower, soybean, potato, tomato, beans such as bush bean and horse bean, flax, pasture grass, fruit growing plants, plantation crops, green and Lawns and squares of residential and industrial facilities, track systems, particularly preferred in monocot crops such as cereals, for example Wheat, barley, rye, oats, crosses thereof such as triticale, rice, corn and millet, and dicotyledon crops such as sunflowers, soybeans, potatoes, tomatoes, peas, carrots and fennel, components i) and ii) of the herbicidal compositions according to the invention being combined or separately, e.g. pre-emergence (very early to late), post-emergence or pre- and post-emergence, on the plants, e.g. Harmful plants, parts of plants, plant seeds or the area on which the plants grow, e.g. applied the acreage.

The invention also relates to the use of the herbicidal compositions according to the invention comprising components i) and ii) for controlling harmful plants, preferably in crops, preferably in the crops mentioned above. The invention furthermore also relates to the use of the herbicidal compositions according to the invention comprising components i) and ii) for controlling herbicide-resistant harmful plants (for example TSR and EMR resistance to ALS and ACCase), preferably in plant crops, preferably in the plant crops mentioned above.

The invention also relates to the process with the herbicidal compositions according to the invention comprising components i) and ii) for the selective control of harmful plants in plant crops, preferably in the plant crops mentioned above, and to the use thereof.

The invention also relates to the process for controlling unwanted vegetation using the herbicidal compositions according to the invention comprising components i) and ii), as well as its use in plant crops which have been genetically modified (transgenic) or obtained by mutation selection and which are used against growth substances, such as, for example, 2,4 D, dicamba or against herbicides, the essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyruvat Dioxygenasen (HPPD) inhibit, respectively against herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and analogous active substances, or against any combination of these active substances. The herbicidal compositions according to the invention can particularly preferably be used in transgenic crop plants which are resistant to a combination of glyphosates and glufosinates, glyphosates and sulfonylureas or imidazolinones. The herbicidal compositions according to the invention can very particularly preferably be used in transgenic crop plants such as, for. B. corn or soy with the trade name or the designation Optimum ™ GAT ™ (Glyphosate ALS Tolerant) can be used.

The invention also relates to the use of the herbicidal compositions according to the invention comprising components i) and ii) for controlling harmful plants, preferably in crops, preferably in the crops mentioned above.

The herbicidal compositions according to the invention can also be used non-selectively for controlling unwanted vegetation, e.g. in plantation crops, on roadsides, squares, industrial plants or railway systems; or used selectively to combat unwanted plant growth in crops for energy generation (biogas, bio-ethanol).

The herbicidal compositions according to the invention can be present both as mixed formulations of components i) and ii) and, if appropriate, with further agrochemical active ingredients, additives and / or customary formulation auxiliaries, which are then used in a customary manner, diluted with water, or as so-called tank mixtures by common dilution of the separately formulated or partially separately formulated components are made with water. Under certain circumstances, the mixed formulations can be diluted with other liquids or solids or used undiluted.

The mixtures / compositions according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. Examples of general formulation options are: wettable powder (WP), water-soluble concentrates, emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, suspension concentrates (SC), dispersions, oil dispersions (OD), suspoemulsions (SE), dusts (DP), mordants, granules for soil or litter application (GR) or water-dispersible granules (WG), ultra-low-volume formulations , Microcapsule or wax dispersions. The individual formulation types 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-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker NY 1973; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: 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, "Solvent Guide," 2nd Ed., Interscience, N.Y. 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., N.Y. 1964; Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1976, Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

On the basis of these formulations, combinations with other agrochemical active ingredients, such as fungicides, insecticides, and safeners, fertilizers and / or growth regulators can also be prepared, e.g. in the form of a finished formulation or as a tank mix.

Spray powders (wettable powders) are preparations which are uniformly dispersible in water and, in addition to the active ingredients, besides one or more diluents or inert substances, surfactants of an ionic and / or nonionic type (wetting agents, dispersing agents), e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, propylene oxide / ethylene oxide copolymers, alkanesulfonates or alkylbenzenesulfonates or alkylnaphthalenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonic acid, sodium dibutylnaphthalene or sodium sulfonate.

Emulsifiable concentrates are made by dissolving the active ingredients in an organic solvent or solvent mixture, e.g. Butanol, cyclohexanone, dimethylformamide, acetophenone, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers which can be used are: alkylarylsulfonic acid calcium salts, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide copolymers, alkyl polyethers, sorbitan fatty acid ester sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene acid sorbetyl ester, polyoxyethylene ethoxylate or polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene ethoxylate or polyoxyethylene ethoxylate, polyoxyethylene ethoxylate.

Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates are water-based suspensions of active ingredients. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of further surfactants, such as those already listed above for the other types of formulation. In addition to the suspended active ingredient or active ingredients, other active ingredients can also be present in solution in the formulation.

Oil dispersions are oil-based suspensions of active substances. Oil is understood to mean any organic liquid, e.g. B. vegetable oils, aromatic or aliphatic solvents, or fatty acid alkyl esters. You can, for example, by wet grinding using commercially available bead mills and optionally adding other surfactants (wetting agents, dispersing agents), such as those e.g. already listed above for the other types of formulation. In addition to the suspended active ingredient or active ingredients, other active ingredients can also be present in solution in the formulation.

Emulsions, e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers made from mixtures of water and water-immiscible organic solvents and, if appropriate, from further surfactants, such as those e.g. already listed above for the other formulation types. The active ingredients are present in dissolved form.

Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinite, chalk or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers. Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. For the production of plate, fluidized bed, extruder and spray granules, see e.g. Procedure in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry’s Chemical Engineer’s Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For further details on the formulation of crop protection agents see, for example, GC Klingman, “Weed Control as a Science”, John Wiley and Sons, Ine., New York, 1961, pages 81-96 and JD Freyer, SA Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103. The agrochemical formulations generally contain 0.1 to 99 percent by weight, in particular 2 to 95% by weight, of active compounds of the herbicide components, the following concentrations being customary depending on the type of formulation: the active compound concentration in wettable powders is, for example, about 10 to 95% by weight. -%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be, for example, 5 to 80% by weight. Dust-like formulations usually contain 5 to 20% by weight of active ingredient, sprayable solutions about 0.2 to 25% by weight of active ingredient. In the case of granules such as dispersible granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulation auxiliaries and fillers are used. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.

In addition, the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, preservatives, antifreeze agents and solvents, fillers, dyes and carriers, defoamers, evaporation inhibitors and agents which control the pH or Influence viscosity.

The herbicidal activity of the mixtures / compositions according to the invention can be improved, for example, by surface-active substances, for example by wetting agents from the range of fatty alcohol polyglycol ethers. The fatty alcohol polyglycol ethers preferably contain 10-18 carbon atoms in the fatty alcohol residue and 2-20 ethylene oxide units in the polyglycol ether part. The fatty alcohol polyglycol ethers can be nonionic or ionic, for example in the form of fatty alcohol polyglycol ether sulfates or phosphates, which are used, for example, as alkali metal salts (for example sodium and potassium salts) or ammonium salts, or also as alkaline earth metal salts such as magnesium salts, such as Ci2 / Ci4-fatty alcohol diglycol ether sodium (Genapol ^® LRO, Clariant GmbH); see for example EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988). Nonionic fatty alcohol polyglycol ethers are, for example, 2-20, preferably 3-15, ethylene oxide units (Cio-Ci ₈ ), preferably (Cio-Ci4) fatty alcohol polyglycol ethers (for example isotridecyl alcohol polyglycol ether), for example from the Genapol ^® X series, such as Genapol ^® X-030, Genapol ^® X-060, Genapol ^® X-080 or Genapol ^® X-150 (all from Clariant GmbH).

The present invention further comprises the combination of the mixtures / compositions according to the invention with the above-mentioned wetting agents from the series of fatty alcohol polyglycol ethers, which preferably contain 10 to 18 carbon atoms in the fatty alcohol residue and 2 to 20 ethylene oxide units in the polyglycol ether part and are nonionic or ionic (e.g. as Fatty alcohol polyglycol ether sulfates) can be present. Preferred are Ci2 / Ci4-fatty alcohol diglycol ether sulfate sodium (Genapol ^® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ether having 3-15 ethylene oxide units, for example from the Genapol ^® X series, such as Genapol ^® X-030, Genapol ^® X 060, Genapol ^® X-080 and Genapol ^® X-150 (all from Clariant GmbH). It is also known that fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (e.g. fatty alcohol polyglycol ether sulfates) are also suitable as penetration aids and activity enhancers for a number of other herbicides, including herbicides from the imidazolinone series (see, for example, EP-A -0,502,014).

The herbicidal activity of the mixtures / compositions according to the invention can also be enhanced by using vegetable oils. The term vegetable oils is understood to mean oils from oil-producing plant species such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, safflower oil or castor oil, in particular rapeseed oil, and their transesterification products, e.g. Alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.

The vegetable oils are preferably esters of C ₁₀ -C ₂₂ -, preferably Ci ₂ -C ₂ o-fatty acids. The C ₁₀ -C ₂₂ fatty acid esters are, for example, esters of unsaturated or saturated Cio-C ₂₂ fatty acids, in particular with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular cis fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.

Examples of Cio-C22 fatty acid esters are esters which are obtained by reacting glycerol or glycol with the Cio-C22 fatty acids, such as those contained in oils from oil-producing plant species, or Ci-C2o-alkyl-CioC22 fatty acid Esters such as can be obtained, for example, by transesterification of the aforementioned glycerol or glycol-Cio-C22 fatty acid esters with C ₁ -C ₂₀ alcohols (for example methanol, ethanol, propanol or butanol). The transesterification can be carried out according to known methods, as described, for example, in the Römpp Chemie Lexikon, 9th edition, volume 2, page 1343, Thieme Verlag Stuttgart.

Preferred Ci-C2o-alkyl-Cio-C22 fatty acid esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethyl-hexyl esters and dodecyl esters. Preferred as glycol and glycerol-Cio-C22 fatty acid esters are the uniform or mixed glycol esters and glycerol esters of Cio-C22 fatty acids, in particular those fatty acids with an even number of carbon atoms, e.g. Erucic acid, lauric acid, palmitic acid and especially cis fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.

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

The present invention includes in a further embodiment, combinations of components i) and ii) with the previously mentioned vegetable oils such as rapeseed oil, preferably in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ^®, Actirob ^® B, Rako-Binol ^® , Renol ^® or Stefes Mero ^® .

For use, the formulations present in the commercial form are optionally diluted in the customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Preparations in the form of dust, ground granules or granules for spreading, and sprayable formulations are usually no longer diluted with other inert substances before use.

The active compounds can be applied to the plants, parts of plants, plant seeds or the area under cultivation (arable soil), preferably to the green plants and parts of plants and, if appropriate, additionally to the arable soil.

One possible application is the joint application of the active ingredients in the form of tank mixtures, the optimally formulated concentrated formulations of the individual active ingredients being mixed with water together in the tank and the spray liquor obtained being applied.

A joint herbicidal formulation of the herbicidal mixtures according to the invention with components i) and ii) has the advantage of being easier to use because the amounts of the components have already been set in the correct ratio to one another. In addition, the auxiliaries can be optimally coordinated in the formulation. A. General Formulation Examples a) A dusting agent is obtained by mixing 10 parts by weight of an active ingredient / active ingredient mixture and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill. b) A wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of an active compound / mixture of active compounds, 64 parts by weight of clay containing kaolin as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyl taurine mixes as a wetting and dispersing agent and grinds in a pin mill. c) A suspension concentrate which is easily dispersible in water is obtained by mixing 20 parts by weight of an active ingredient / active ingredient mixture with 5 parts by weight of tristyrylphenol polyglycol ether (Soprophor BSU), 1 part by weight of sodium figninsulfonate (Vanisperse CB) and 74 parts by weight. - Mixes water and grinds to a fineness of less than 5 microns in a attritor. d) An oil dispersion which is easily dispersible in water is obtained by mixing 20 parts by weight of an active ingredient / active ingredient mixture with 6 parts by weight of alkylphenol polyglycol ether ( ^Triton® X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight. Parts of paraffinic mineral oil (boiling range approx. 255 to 277 ° C) and ground in a friction ball mill to a fineness of less than 5 microns. e) An emulsifiable concentrate is obtained from 15 parts by weight of one

Active ingredient / active ingredient mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier. f) A water-dispersible granulate is obtained by adding 75 parts by weight of an active ingredient / active ingredient mixture,

10 parts by weight of calcium lignosulfonic acid,

5 parts by weight of sodium lauryl sulfate,

3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin are mixed, ground in a pin mill and the powder is granulated in a fluidized bed by spraying water as the granulating liquid. g) A water-dispersible granulate is also obtained by adding 25 parts by weight of an active ingredient / active ingredient mixture,

5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium,

2 parts by weight of sodium oleoylmethyl taurine,

1 part by weight of polyvinyl alcohol,

17 parts by weight of calcium carbonate and 50 parts by weight of water are homogenized and pre-comminuted on a colloid mill, then ground on a bead mill and the suspension thus obtained is atomized and dried in a spray tower using a single-component nozzle.

B. Biological examples a) Method descriptions of greenhouse experiments

In the standard experiment, the seeds of different weed and weed biotypes (origins) were sown in a pot of 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt) and covered with a covering layer of the soil of about 1 cm. The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots were then cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were treated on a laboratory spray track with spray liquors with the mixtures / compositions according to the invention, mixtures of the prior art or with the individually applied components. The active ingredients or combinations of active ingredients formulated as WG, WP, EC or other formulations were applied at the corresponding growth stages of the plants. The water application rate for the spray application was 100-600 l / ha. After the treatment, the plants were put back in the greenhouses.

About 3 weeks after application, the soil and / or leaf effect was assessed optically on a scale of 0-100% compared to an untreated comparison group: 0% = no discernible effect compared to the untreated comparison group; 100% = complete effect compared to the untreated control group.

(Notes: The term "seeds" also includes vegetative forms of propagation, such as rhizome pieces; abbreviations used: h light = hours of illumination, g AS / ha = grams of active substance per hectare, 1 / ha = liter per hectare, S = sensitive, R = resistant)

1. Pre-emergence weed action: Seeds of different weeds and weed biotypes (origins) were sown in a pot of 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt) and covered with a covering layer of the soil of about 1 cm. The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots were then cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were treated in the BBCH stage 00-10 of the seeds / plants on a laboratory spray track with spray liquors with the mixtures / compositions according to the invention, mixtures or with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 100-600 l / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed.

2. Post-emergence weed action: Seeds of different weeds and weed biotypes (origins) were grown in a standard field soil (loamy silt) with natural soil filled pot of 8-13 cm in diameter and covered with a covering layer of about 1 cm in the bottom. The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots were then cultivated in a greenhouse (12-16h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were at different BBCH stages between 11-25 of the seeds / plants, ie generally between two to three weeks after the start of cultivation, on a laboratory spray track with spray liquors with the mixtures / compositions, mixtures or with the individually applied components as WG, WP, EC or other formulations treated. The water application rate for the spray application was 100-600 l / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed. Pre-emergence weed effects with and without active ingredient incorporation: Seeds of different weeds and weed biotypes (origins) were sown in a pot of 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt). The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots with the seeds were compared either in the BBCH stage 00-10 of the seeds / plants, ie generally between two to three weeks after the start of cultivation, on a laboratory spray track with spray liquors with the mixtures / compositions, mixtures or mixtures according to the invention individually applied components treated as WG, WP, EC or other formulations, or an equivalent amount of the mixtures / compositions, mixtures or individually applied components as WG, WP, EC or other formulations were incorporated into the top layer of 1 cm. The water application rate for the spray application was 100-600 l / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed. The pots were cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C). Pre-emergence selectivity: Seeds of different crops (origins) were sown in a pot of 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt) and covered with a covering layer of about 1 cm. The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots were then cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were treated in the BBCH stage 00-10 of the seeds / plants on a laboratory spray track with spray liquors with the mixtures / compositions according to the invention, mixtures or with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 100-600 1 / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed. Selectivity effect in post-emergence: Seeds of different crops (origins) were sown in a pot of 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt) and covered with a covering layer of the soil of about 1 cm. The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots were then cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were at different BBCH stages 11-32 of the seeds / plants, ie generally between two to four weeks after the start of cultivation, on a laboratory spray track with spray liquors using the inventive

Mixtures / compositions, mixtures or treated with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 100-600 l / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed. The pots were cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) weed action in the pre-sowing application: seeds of different weeds and weed biotypes

(Origins) were sown in a pot 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt). The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots with the seeds were sprayed with the broths according to the invention on a laboratory spray lane before sowing

Mixtures / compositions, mixtures or treated with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 100-600 l / ha. After sowing, the pots were set up in the greenhouses and fertilized and watered as needed. The pots were cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C). Weed effects in the pre- and post-emergence under different cultivation conditions: Seeds of different weeds and weed biotypes (origins) were sown in a pot filled with natural soil from a standard field soil (loamy silt) of 8-13 cm in diameter and covered with a covering layer of the soil of about 1 cm , The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots were then cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were treated at different BBCH stages 00-25 of the seeds / plants on a laboratory spray track with spray liquors with the mixtures / compositions according to the invention, mixtures or with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 100-600 1 / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed. The pots were cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C). The irrigation was varied according to the question. The individual comparison groups were supplied with water in increments ranging from above the PWP (permanent wilting point) and up to the level of the maximum field capacity. Weed effects in the pre- and post-emergence under different irrigation conditions: Seeds of different weeds and weed biotypes (origins) were sown in a pot filled with natural soil from a standard field soil (loamy silt) with a diameter of 8-13 cm and covered with a covering layer of the soil of about 1 cm , The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots were then cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were treated at different BBCH stages 00-25 of the seeds / plants on a laboratory spray track with spray liquors with the mixtures / compositions according to the invention, mixtures or with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 100-600 l / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed. The pots were cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C). The individual comparison groups were exposed to different irrigation techniques. Irrigation was carried out either from below or in increments from above (simulated irrigation). Weed effects in the pre- and post-emergence under different soil conditions: Seeds of different weeds and weed biotypes (origins) were sown in a pot of 8-13 cm diameter filled with natural soil and covered with a covering layer of the soil of about 1 cm. For a comparison of the herbicidal activity, the plants were cultivated in different growing media, from a sandy soil to heavy clay soil and various organic matter contents. The cultivation soils are used sterile or non-sterile depending on the test conditions. The pots were then cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were treated at different BBCH stages 00-25 of the seeds / plants on a laboratory spray track with spray liquors with the mixtures / compositions, mixtures or with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 100-600 l / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed. The pots were cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C). 10. Weed action in the pre- and post-emergence to combat resistant weed / weed species: Seeds of different weed and weed biotypes (origins) with different resistance mechanisms against different mechanisms of action were grown in a standard field soil with natural soil (loamy silt, LSI; pH 7.4;% C org 2.2) filled pot of 8 cm in diameter and covered with a covering layer of the bottom of about 1 cm. The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots were then cultivated in a greenhouse (12-16 h light, temperature day approx. 23 ° C, night approx. 15 ° C) until the time of application. The pots were treated at different BBCH stages 00-25 of the seeds / plants on a laboratory spray track with spray liquors with the mixtures / compositions, mixtures or with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 300 l / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed. The pots were cultivated in a greenhouse (12-16 h light, temperature day approx. 23 ° C, night approx. 15 ° C).

11. Weed action and crop selectivity in the pre- and post-emergence under different sowing conditions: Seeds of different weeds, weed biotypes (origins) and crop types (origins) were sown in a pot filled with natural soil with a diameter of 8-13 cm and with a covering layer of the soil from covered about 0-5cm. The soil of the standard field floor is used sterile or non-sterile depending on the test conditions. The pots were then cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were treated at different BBCH stages 00-25 of the seeds / plants on a laboratory spray lane with spray liquors with the mixtures / compositions, mixtures or with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 100-600 l / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed. The pots were cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C).

12. Weed action in pre- and post-emergence at different soil pH values: Seeds of different weed and weed biotypes (origins) were sown in a pot of 8-13 cm diameter filled with natural soil and covered with a covering layer of the soil of about 1 cm , For a comparison of the herbicidal action, the plants were cultivated in soil from a standard field soil (loamy silt) with different pH values of pH 7.4 and pH 8.4. The soil was mixed accordingly with lime to the higher pH. The soil of the standard field floor becomes sterile or non-sterile depending on the test conditions used. The pots were then cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were treated at different BBCH stages 00-10 of the seeds / plants on a laboratory spray track with spray liquors with the mixtures / compositions according to the invention, mixtures or with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 100-600 l / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed. The pots were cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C).

field trials

In field trials, the agents according to the invention, mixtures of the prior art or the individual components were applied under natural conditions with field preparation customary in practice and with natural or artificial contamination with harmful plants before or after sowing the crop plants or before or after emergence of the harmful plants and in the period from Visually rated 4 weeks to 8 months after treatment compared to untreated sections (plots). The damage to crops and the activity against harmful plants were recorded as a percentage, as were the other effects of the respective test question. b) results

The following method was used for the results:

Pre-emergence weed action: Seeds of different weeds and weed biotypes (origins) were sown in a pot of 8 cm diameter filled with natural soil from a standard field soil (loamy silt; steamed) and covered with a covering layer of the soil of about 1 cm. The pots were then cultivated in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were treated in BBCH stage 00-06 of the seeds on a laboratory spray track with spray liquors with the mixtures / compositions according to the invention, mixtures or with the individually applied components as WG, WP, EC or other formulations. The water application rate for the spray application was 300 l / ha. After the treatment, the plants were put back in the greenhouses and fertilized and watered as needed.

The following abbreviations were used:

BBCH = BBCH code provides information about the morphological stage of development of a plant. The abbreviation officially stands for the Federal Biological Institute, the Federal Plant Variety Office and the chemical industry. The range of BBCH 00-10 stands for the stages from seed germination to penetration of the Surface. The area from BBCH 11-25 stands for the stages of leaf development up to tillering (according to the number of tillers or side shoots).

PE = pre-emergence application on the floor; BBCH of the seeds / plants 00-10.

PO = post-emergence application on the green plant parts; BBCH of plants 11-25.

HRAC = 'Herbicide Resistance Action Committee', which classifies the approved active substances according to their mode 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 substance (based on 100% active ingredient; syn. A.i. (English)).

Dose g AS / ha = application rate in grams of active ingredient per hectare.

The following weed and weed biotypes were used in the experiments:

ALOMY - sensiti v (Alopecurus myosuroides) Sensitive to common herbicides

Agents.

ALOMY - resistant (Alopecurus myosuroides) resistant to herbicides

Agents. the HRAC groups A and B; Population mix of a field origin with increased metabolic resistance (EMR) and a portion of target site resistance (TSR).

LOLRI - sensitive (Lolium rigidum) Sensitive to common herbicidal agents.

LOLRI - resistant (Lolium rigidum) resistant to herbicidal agents. the HRAC groups A and B; Population mix of a field origin with increased metabolic resistance (EMR) and a portion of target site resistance (TSR).

AVEFA (Avenafatua) - Wild oat

BREAST (Bromus sterilis) - bromegrass, ingot

SORHA (Sorghum halepense) - Johnsongrass

BRSNW (Brassica napus) - rape, winter

CENCY (Centaurea cyanus) - Cornflower

EMEAU (Emex australis) - Cathead GALAP (Gallium aparine) - Cleaver PAPRH (Papaver rhoeas) - Poppy, common RAPRA (Raphanus raphanistrum) - Charlock, jointed VERHE (Veronica hederaefolia) - Speedwell, iveleaf HORVS (Hordeum vulgare) - Barley, spring

TRZAS (Triticum aestivum) - Wheat, spring

The effects of the herbicidal compositions according to the invention meet the requirements set and thus solve the task of improving the application profile of the herbicidal active ingredient aclonifen (including providing more flexible solutions in relation to necessary application rates with constant to increased effectiveness).

Insofar as the herbicidal effects of the compositions according to the invention were in focus in comparison with mixtures of the prior art or with individually applied components against economically important monocotyledonous and dicotyledonous harmful plants, the synergistic herbicidal effects were based on the 'Colby formula' (cf. SR Colby; Weeds 15 (1967), 20-22) calculated:

Claims

claims:

1. Herbicidal mixture containing i) aclonifene and ii) cinmethylin.

2. Herbicidal mixture according to claim 1 containing at least one further herbicide from group I:

2- [(2,4-dichlorophenyl) methyl] -4,4-dimethyl-3-isoxazolidinone, acetochlor, acifluorfen, acifluorfen-sodium, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4 -amino-3-chloro-6- (4-chloro-2-fluoro-3-methylphenyl) -5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachloro- potassium, aminocyclopyrachloromethyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos-sodium, bispanibibacac, sodium, bispanibosac, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstroleent, carbentamide, carfam on, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorosulfuron, cinidon, cinidon-ethyl, cinosulfuron, clacyfodin, clafopim, clafop-, clethodim propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butot -butyl, -dimethylammonium, - diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, - triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium , isooctyl, potassium and sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2- (2,4-dichlorobenzyl) -4,4-dimethyl -l, 2-oxazolidin-3-one, 2- (2,5-dichlorobenzyl) -4,4-dimethyl-l, 2-oxazolidin-3-one, dichloroprop, dichloroprop-P, diclof op, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflu- fenican, diflufenzopyr, diflufenzopyr- sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinithenine, dinitramine, dinitramine diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, F-5231, ie N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-lH-tetrazol-l-yl] - phenyl] ethanesulfonamide, F-7967, ie 3- [7-chloro-5-fluoro-2- (trifluoromethyl) -lH-benzimidazol-4-yl] -l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (lH, 3H) -dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumuronoluren, flumuroxoluren, flumuroxoluren, fluumuron, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, flomesiacetosulfamates, futhiacetosulfamates, fomethafenet forsulfamone, fomethafenet famsam, methylsulfonate ine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium H-9201, ie 0- (2,4-dimethyl-6-nitrophenyl) -0-ethyl-isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop -P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, ie l- (dimethoxyphosphoryl) - ethyl- (2,4-dichlorophenoxy) acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium , imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, iodine, iodine, iodine, iodine, iodine, iodine, iodine, iodine, iodine, iodine, iodine, iodine, iodine, sodium ioxynil, sodiumoxynil, iodine, iodine, iodine, iodine, sodium ioxynil, sodium ioxynil, sodium, ioxynyl, sodium, ioxynil, sodium, ioxynoxyn ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutilate, KUH-043, ie 3 - ({[5- (Difluoromethyl) -1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] methyl} sulfonyl) -5,5-dimethyl-4,5-dihydro-l, 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, methabenzthiazuron, metam, metamifop, metamitronaben, metazachuron, methazachuron, meth , methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-3, chlorine 4- (l-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic a cid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, propach, propa, propetran, propetran, propetran , propisochlor, propoxycarbazone, propoxycarbazone- sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyamibzylamylbenzamethylbenzambenz pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofal-ethyl-quizalofalopol quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfe ntrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron,, SYN-523, SYP-249, ie 1-ethoxy-3-methyl-l-oxobut-3-en-2-yl-5- [2-chloro-4- ( trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP-300, ie l- [7-fluoro-3-oxo-4- (prop-2-in-l-yl) -3,4-dihydro-2H-1,4 -benzoxazin-6-yl] -3- propyl-2-thioxoimidazolidin-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb , terbumetone, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-alliburon, tri-alluron, tri-alluronuron, tri-allonuron , trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea Sulfate, vernolate, XDE-848, ZJ-0862, ie 3,4-dichloro-N- {2 - [({ 6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following compounds Ungen:

3. Herbicidal mixture according to one of claims 1 or 2 containing at least one safener, the application rate generally being 5-2000 g ai / ha, preferably 10-500 g ai / ha and particularly preferably 10-300 g ai / ha.

4. Herbicidal mixture according to one of claims 1 or 2 containing at least one safener from the group consisting of: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethy 1st

5. Herbicidal mixture according to one of claims 1 to 4, wherein the herbicide components are in the weight ratio given below:

(Component i range): (Component ii range) in general (l-1000) :( l-1000), preferably (l-100) :( l-100), particularly preferably (1-50) :( 1-50 ).

6. Herbicidal mixture according to one of claims 1 to 5, containing the application rates specified below for the respective herbicide components:

Component i): generally 1 - 2000 g ai / ha, preferably 10 - 1000 g ai / ha, particularly preferably 10 - 500 g ai / ha aclonifen;

Component ii): generally 1 - 2000 g ai / ha, preferably 10 - 1000 g ai / ha, particularly preferably 10 - 500 g ai / ha cinmethylin.

7. Herbicidal mixture according to one of claims 1 to 6, additionally containing additives and / or formulation auxiliaries customary in crop protection.

8. Herbicidal composition / mixture according to one of claims 1 to 7, additionally containing one or more further components from the group of agrochemical active ingredients comprising insecticides and fungicides.

9. A method for controlling unwanted vegetation, in which components i) and ii) of the herbicidal mixtures / compositions, defined according to one of claims 1 to 8, together or separately on the plants, parts of plants, plant seeds or the area on which the plants grow, be applied.

10. The method according to claim 9 for the selective control of harmful plants in plant crops.

11. The method according to claim 9, wherein the plant cultures are genetically modified or by

Mutation selection were obtained.

12. Use of the herbicidal mixtures / compositions according to any one of claims 1 to 8 for controlling harmful plants.

13. Use of the herbicidal mixtures / compositions according to any one of claims 1 to 8 for controlling herbicide-resistant harmful plants.