WO2010066679A2 - Herbicidal mixtures - Google Patents

Abstract

Herbicidal mixtures comprising a) at least one active compound A from the group of the cellulose biosynthesis inhibitors selected from chlorthiamid, dichlobenil, flupoxam, isoxaben, triaziflam, indaziflam, 1-cyclohexyl-5-pentafluorophenyloxy-1?4-[1,2,4,6]thiatriazin-3-ylamine and thaxtomin derivatives of the formula (I) in which the variables are as defined in the description and b) at least one active compound B from the group of VLCFA inhibitors selected from: chloroacetamides, oxyacetanilides, acetanilides, tetrazolinones, and other VLCFA inhibitors, compositions comprising them, and also methods for controlling unwanted vegetation.

Description

 Herbicidal mixtures

description

The present invention relates to herbicidal mixtures containing

a) at least one active substance A from the group of cellulose biosynthesis

Inhibitors selected from chlorothiamide, dichlobenil, flupoxam, isoxaben, triacidlam, indaziflam, 1-cyclohexyl-5-pentafluorophenyloxy-1λ ⁴ - [1, 2,4,6] thiatriazine-3-ylamine and thaxtomin derivatives of the formula I.

worin

wherein

R ^{a is} CN, CF ₃ or NO ₂ ; R ^{1 is} H or OH; A is phenyl or a five- or six-membered fully unsaturated ring which, in addition to carbon, may contain 1, 2 or 3 heteroatoms selected from O, N and S; and R ^1, R ² H, OH, halogen, C -C alkyl or C ₄ -alkyl mean ₄ haloalkyl,

and

b) at least one active substance B from the group of VLCFA inhibitors selected from: b1) chloroacetamides such as acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S,

Pethoxamide, pretilachlor, propachlor, propisochlor, and thenylchloro b2) oxyacetanilides such as flufenacet and mefenacet, b3) acetanilides such as diphenamid, naproanilide and napropamide, b4) tetrazolinones such as fentrazamide, and b5) other VLCFA inhibitors such as anilofos, cafenstrol, piperophos,

Pyroxasulfone 2:

worin

wherein

Y is phenyl or 5- or 6-membered heteroaryl as defined above, which may be substituted by one to three groups R; R is halogen, Ci _-C4 -alkyl, Ci-C ₄ alkoxy, Ci-C ₄ haloalkyl, or -C ₄ -

haloalkoxy;

R ²¹ , R ²² , R ²³ , R ^{24 are} H, halogen or C 1 -C ₄ -alkyl; X is O or NH; n is 0 or 1.

In the case of crop protection agents, it is generally desirable to increase the specific action of an active substance and the safety of action. In particular, it is desirable if the plant protection product effectively combats the harmful plants, but at the same time is compatible with the respective crops. It is also desirable to have a broad spectrum of activity for the simultaneous control of harmful plants. This can often not be achieved with a herbicidal active ingredient.

For many highly effective herbicides, the problem is that their compatibility with crops, especially dicotyledonous crops such as cotton, rape and grass plants such as barley, millet, corn, rice, wheat and sugar cane is not always satisfactory, ie in addition to the harmful plants and the crops in one not tolerable dimensions damaged. By reducing the application rates while the crops are spared, but at the same time naturally decreases the extent of harmful plant control. In addition, there is often the problem that the herbicides can be used only in a narrow time window in order to achieve the desired herbicidal action, wherein the time window can be influenced in an unpredictable manner by weather conditions.

It is known that specific combinations of different specific active herbicides result in an increase in the activity of a herbicidal component in the sense of a synergistic effect. As a result, the required amounts of herbicidal active ingredients required to control harmful plants can be reduced.

Furthermore, it is known that in some cases the combined application of specific acting herbicides with organic active ingredients, the z.T. themselves have herbicidal activity, better crop compatibility can be achieved. The active ingredients act as antidotes or antagonists in these cases and are also referred to as safeners, as they reduce the damage to the crop or even prevent it.

The above-mentioned cellulose biosynthesis inhibitors (CBI) and VLCFA inhibitors, their preparation and their herbicidal action are known J. Agric. Food Chem. (2001) 49, 2298-2301, WO 97/25318, WO 06/024820, WO 06/037945, WO 07/071900 and WO 07/096576 the agents named by common name are commercially available.

The object of the invention is to provide herbicidal compositions which have a high activity against unwanted harmful plants. The compositions should at the same time have good crop compatibility. sen. In addition, the compositions of the invention should show a broad spectrum of activity.

These and other objects are achieved by the herbicidally active compositions according to the invention containing the active components a) and b), as defined above.

In particular, the invention relates to compositions in the form of herbicidally active crop protection compositions containing a herbicidally effective amount of a drug combination comprising at least one CBI and at least one VLCFA inhibitor, and at least one liquid and / or solid carrier and / or one or more surfactants and, if desired one or more further auxiliaries customary for pesticides.

The invention also relates to compositions in the form of a plant protection composition formulated as a 1-component composition, comprising a combination of active substances comprising at least one active substance A and at least one further active ingredient B, and at least one solid or liquid carrier and / or one or more surface-active substances if desired, one or more further auxiliaries customary for pesticides. The invention also relates to compositions in the form of a plant protection composition formulated as a 2-component composition comprising a first component comprising at least one active substance A, a solid or liquid carrier and / or one or more surface-active substances, and a second component containing at least one further active ingredient, selected from the active compounds B, a solid or liquid carrier and / or one or more surface-active substances, wherein in addition both components may also contain other, customary for crop protection agents.

The compositions of the invention containing at least one active ingredient A and at least one active ingredient B exhibit better herbicidal efficacy, i. H. a better action against harmful plants than would have been expected due to the herbicidal activity observed for the individual compounds (synergistic effect), or a broader spectrum of activity.

In addition, by the compositions according to the invention, which contain both at least one active ingredient A and one active ingredient B, the time window within which the desired herbicidal action can be achieved is increased. This allows a more flexible temporal use of the compositions of the invention compared to the individual compounds.

The compositions of the invention also show a good herbicidal activity against harmful plants and a better crop compatibility. The compositions according to the invention have a better herbicidal activity, ie a better action against harmful plants than would have been expected on account of the herbicidal activity observed for the individual compounds. Furthermore, the invention relates to a method for controlling undesired plant growth, in particular in cultivated areas of crop plants, for example in crops of the following crop plants: Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phasolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spp., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus com munis, Saccharum officinarum, Seeale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgaris), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays, especially cereal, maize, soybean, rice, rapeseed, cotton, potato, peanut or permanent crops, as well as in crops that are resistant to one or more herbicides or to insect infestation through genetic engineering or breeding measures.

The invention also relates to a method for desiccation or defoliation of plants. In the latter method, it is irrelevant whether the herbicidally active compounds of components A) and B) are formulated and applied together or separately and in which order the application is carried out with separate application.

A preferred embodiment of the combinations according to the invention contains as active ingredient A chlorothiamide.

A further preferred embodiment contains dichlobenil as active ingredient A.

A further preferred embodiment contains as active ingredient A flupoxam.

A further preferred embodiment contains as active ingredient A isoxaben.

A further preferred embodiment contains as active ingredient A triaziflam.

A further preferred embodiment contains as active ingredient A 1 -cyclohexyl-5-pentafluorophenyloxy-1 λ ⁴ - [1, 2,4,6] thiatriazin-3-ylamine (compound A-6).

A further preferred embodiment contains Indaziflam as active ingredient A.

A further preferred embodiment contains, as active ingredient A, a thaxtomin derivative of the formula I, in particular one in which A is phenyl or thiophene. In particular, the following active substances come into question:

An embodiment of the invention contains as active ingredient B a chloroacetamide.

Another embodiment contains as active ingredient B an oxyacetanilide.

Another embodiment contains as active ingredient B an acetanilide.

Another embodiment contains as active ingredient B a tetrazolinone.

Another embodiment contains as active ingredient B one of the other VLCFA inhibitors, as defined above.

Preferred embodiments of the invention relate to combinations of an active substance A with an active ingredient B which is selected from dimethachlor, metolachlor, metolachlor-S, flufenacet, napropamide, fentrazamide and pyroxasulfone. A further preferred embodiment relates to the combination of an active compound A with an isoxazoline compounds of the formula 2. Of these, the compounds of

Formula 2 is preferred in which

bedeutet, wobei # die Bindung zu dem Molekülgerüst bedeutet;

where # is the bond to the molecular skeleton;

_R 2i _{i R} 22 _R 23 _R 24 _{H i} (^ _{F or C} H _{3; R} 25 is halogen, C 1 -C ₄ -alkyl or C 1 -C ₄ -haloalkyl; R ^{26 is} C 1 -C ₄ -alkyl; R ^{27 is} halogen, C 1 -C ₄ - alkoxy or _{Ci-C4-haloalkoxy;} R ²⁸ is H, halogen, CrC ₄ - alkyl, Ci-C ₄ haloalkyl or _{Ci-C4-haloalkoxy;} m is 0, 1, 2 or 3; X is oxygen; n is 0 or 1 Particularly preferred compounds of the formula 2 have the following meanings:

R ²¹ H; R ^22, R ²³ F; R ²⁴ H or F; X oxygen; n 0 or 1.

Particularly preferred compounds of the formula 2 are:

3- [5- (2,2-Difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfonyl] -4-fluoro-5,5-dimethyl-4,5-dihydro -isoxazole (2-1); 3 - {[5- (2,2-Difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] -fluoro-methanesulfonyl} -5,5-dimethyl-4,5 dihydro-isoxazole (2-2); 4- (4-Fluoro-5,5-dimethyl-4,5-dihydroisoxazol-3-sulfonylmethyl) -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-3 ); 4 - [(5,5-dimethyl-4,5-dihydroisoxazol-3-sulfonyl) fluoromethyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-4 ); 4- (5,5-dimethyl-4,5-dihydroisoxazol-3-sulfonylmethyl) -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-5); 3 - {[5- (2,2-Difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] -difluoro-methanesulfonyl} -5,5-dimethyl-4,5-dihydro -isoxazole (2-6); 4 - [(5,5-Dimethyl-4,5-dihydro-isoxazol-3-sulfonyl) -difluoro-methyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-7 ); 3 - {[5- (2,2-difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] difluoro-methanesulfonyl} -4-fluoro-5,5-dimethyl-4 , 5-dihydroisoxazole (2-8); 4- [Difluoro (4-fluoro-5,5-dimethyl-4,5-dihydroisoxazol-3-sulfonyl) methyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-9); 3 - [(5-Difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl) -difluoro-methanesulfonyl] -5,5-dimethyl-4,5-dihydro-isoxazole (2-10). Particularly preferred binary combinations of the active compounds A and B are:

The binary combinations according to the invention, in particular the abovementioned A-1 to A-315, may optionally contain a further active component C. Such ternary combinations may comprise as active component C at least one and preferably one herbicide C and / or at least one and preferably one safener D.

In one embodiment, the compositions according to the invention comprise as third component c) at least one, and preferably a herbicide selected from groups d) to c13) as defined below. In a further embodiment, at least one, and preferably a safener D, is present as the third component C).

In a further embodiment, the third component C) is a herbicide selected from groups d) to c13) and the fourth component at least one, and preferably a safener D before.

Of the ternary compositions of the invention, those containing at least one herbicide C are preferred.

Examples of herbicides C that can be used in combination with the active compounds A according to the present invention are: d) from the group of lipid biosynthesis inhibitors:

Alloxydim, alloxydim sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, Fluazifop-butyl, FIuac-p-P, Fluazifop-P-butyl, Haloxyfop, Haloxyfop-methyl, Haloxyfop-P, Haloxyfop-P-methyl, Metamifop, Pinoxaden, Profoxydim, Propaquizafop, Quizalofop, Quizalofopethyl, Quizalofop-tefuryl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Sethoxydim, Tepraloxydim, Tralkoxydim, Benfuresat, Butylate, Cycloat, Dalapon, Dimepiperate, EPTC, Esprocarb, Ethofumesate, Flupropanate, Molinate, Orbencarb, Pebulate, Prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate; c2) from the group of ALS inhibitors:

Amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cloransulam, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, Flucarbazone sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foram-sulfurone, halosulfuron, halosulfuron-methyl, imazamethabenz, imazamethabenz- methyl, imazapox, imazapyr, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, primisulfuron-methyl, Propoxycarbazone, propoxycarbazone sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribenzoxime, pyrimisulfan, pyridalid, pyrimi- nobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, Thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron; c3) from the group of photosynthesis inhibitors:

Ametryn, amicarbazone, atrazine, bentazone, bentazone sodium, bromacil, bromofenoxime, bromoxynil and its salts and esters, chlorobromuron, chloridazon, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquat-dibromide , Diuron, fluometuron, hexazinone, loxynil and its salts and esters, isoproturon, isourone, carbutilate, lenacil, linuron, metamitron, methabenzthiazirone, metobenzuron, methoxuron, metribuzin, monolinuron, neburon, paraquat, paraquat dichloride, paraquat dimethylsulfate, pentanochlor, phenmedipham, phenmediphamethyl, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumetone, terbuthylazine, terbutryn, thidiazuron and trietazine; c4) from the group of protoporphyrinogen IX oxidase inhibitors: acifluorfen, acifluorfen sodium, azafenidine, bencarbazone, benzfendizone, bifenox, buafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidone-ethyl, fluazolate, flufenpyr, flufenpyr- ethyl, flumiclorac, flumiclorac-pentyl, flumioxazine, fluoroglycofene, fluoroglycofenethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen- ethyl, saflufenacil, sulfentrazone, thidiazimine, 2-chloro-5- [3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl) -1 (2H) -pyrimidinyl] -4-fluoro-N [(isopropyl) methylsulfamoyl] benzamide (CAS 372137-35-4), [3- [2-chloro-4-fluoro-5- (1-methyl-6-trifluoromethyl-2,4-dioxo-1, 2,3,4-tetrahydropyrimidin-3-yl) phenoxy] -2-pyridyloxy] acetic acid ethyl ester (CAS 353292-31-6), N-ethyl-3- (2,6-dichloro-4-trifluoromethylphenoxy) -5- Methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3- (2,6 dichloro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) -5 -methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7) and N-tetrahydrofurfuryl-3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole 1-carboxamide (CAS 45100-03-7); c5) from the group of bleacher herbicides:

Aclonifen, Amitrole, Beflubutamide, Benzobicyclone, Benzofenap, Clomazone, Diflufenicanone, Fluridone, Flurochloridone, Flurtamone, Isoxaflutole, Mesotrione, Norflurazon, Picolinefine, Pyrasulfutole, Pyrazolynate, Pyrazoxyfen, Sulcotrione, Tefuryltrione, Tembotrione, Topramezone, 4- hydroxy-3 - [[2 - [(2-methoxyethoxy) methyl] -6- (trifluoromethyl) -3-pyridyl] car- bonyl] bicyclo [3.2.1] oct-3-en-2-one (CAS 352010-68-5) and 4- (3-trifluoromethylphenoxy) -2- (4-trifluoromethylphenyl) pyrimidine (CAS 180608-33- 7); c6) from the group of EPSP synthase inhibitors:

Glyphosate, glyphosate isopropylammonium and glyphosate trimesium (sulfosate); c7) from the group of glutamine synthase inhibitors:

Bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium; c8) from the group of DHP synthase inhibitors: asulam; c9) from the group of mitosis inhibitors: amiprophos, amiprophos-methyl, benfluralin, butamiphos, butraline, carbetamide,

Chlorpropham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, flulcholine, oryzalin, pendimethalin, prodiamine, prophy, propyzamide, tebutam, thiazopyr and trifluralin; c10) from the group of decoupling herbicides: dinoseb, dinoterb and DNOC and its salts; d 1) from the group of auxin herbicides:

2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts, such as aminopyralid tris (2-hydroxypropyl) ammonium and its esters, benazoline, benazolin-ethyl, chloroamben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quineme-rac, TBA (2, 3,6) and its salts and esters, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (CAS 858956-08-8) and its salts and esters; c12) from the group of auxin transport inhibitors: diflufenzopyr, diflufenzopyrsodium, naptalam and naptalam sodium; c13) from the group of the other herbicides: bromobutide, chlorofluorol, chlorofluorolmethyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metylsulfates, dimethipine, DSMA, dymron, endothal and its salts, etobenzanide, flamprop, Flamprop-isopropyl, Flamprop-methyl Flamprop-M-isopropyl, Flamprop-M-methyl, Flurenol, Flurenol-butyl, Flurprimidol, Fosamine, Fosamine-ammonium, Indano fan, maleic acid hydrazide, Mefluidide, Metam, methyl azide, methyl bromide, methyl -dymron, methyl iodide. MSMA, oleic acid, oxaziclomefon, pelargonic acid, pyributicarb, quinoclamin, triaziflam, tridiphan and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinoline (CAS 499223-49-3) and its salts and esters.

Suitable safeners D are in particular: Benoxacor, Cloquintocet, Cyometrinil, Cyprosulfamide, Dichlormid, Dicyclonon,

Dietholates, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenopyr, mephenate, naphthalic anhydride, oxabetrinil, 4- (dichloroacetyl) -1-oxa-4-aza spiro [4.5] decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (R-29148, CAS 52836-31-4).

Particularly preferred herbicides C which can be used in combination with the active compounds A and B according to the present invention are: d) from the group of lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop- P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, esprocarb, prosulfocarb, thiobencarb and triallate; c2) from the group of ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, lodosulfuron, lodosulfuron-methyl- sodium, mesosulfuron, nicosulfuron, penoxsulam, propoxycarbonazone sodium, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thi-carbazone-methyl, and tritosulfuron; c3) from the group of photosynthesis inhibitors: atrazine, diuron, fluometuron,

Hexazinone, isoproturon, metribuzin, paraquat, paraquat-dichloride, propanil and terbutylazine; c4) from the group of protoporphyrinogen IX oxidase inhibitors: flumioxazine, oxyfluorfen, sulfentrazone, 2-chloro-5- [3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl) -1 (2H) -pyrimidinyl] -4-fluoro-N - [(isopropyl) methylsulfamoyl] benzamide (CAS 372137-35-4) and [3- [2-chloro-4-fluoro-5- (1-methyl-6-) trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl) phenoxy] -2-pyridyloxy] -acetic acid ethyl ester (CAS 353292-31-6); c5) from the group of bleacher herbicides: clomazone, diflufenican, flurochloridone, isoxaflutole, mesotrione, picolinafen, sulcotrione, tefuryltrione, tembotrione, topramezone and 4-hydroxy-3 - [[2 - [(2-methoxyethoxy) methyl] -6 - (trifluoromethyl) -3-pyridyl] carbonyl] - bicyclo [3.2.1] oct-3-en-2-one (CAS 352010-68-5); c6) from the group of EPSP synthase inhibitors: glyphosate, glyphosate-isopropyl-ammonium and glyphosate-trimesium (sulfosate); c7) from the group of glutamine synthase inhibitors: glufosinate, glufosinate-ammonium; c8) from the group of mitosis inhibitors: pendimethalin and trifluralin; c9) from the group of auxin herbicides: 2,4-D and its salts and esters, aminopyridone and its salts, such as aminopyralid tris (2-hydroxypropyl) ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, fluoroxypyr-meptyl, quinclorac, quinmerac and δ-dichloro-cyclopropyl-pyrimidinecarboxylic acid (CAS 858956-08-8) and its salts and esters; c10) from the group of auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium, d 1) from the group of other herbicides: Dymron (Daimuron), Indanofan and Oxaziclomefon.

Examples of preferred safeners D are Benoxacor, Cloquintocet, Cyprosulfamide, Dichlormid, Fenchlorazole, Fenclorim, Flurazole, Fluxofenim, Isoxadifen, Mefenpyr, Naph- thalian acid anhydride, oxabetrinil, 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3. oxazolidine (R-29148, CAS 52836-31-4).

Particularly preferred safeners D are benoxacor, cloquintocet, cyprosulfamide, dichloromide, fenchlorazole, isoxadifen, mefenpyr, 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (MON4660, CAS 71526-07-3) and 2 , 2,5-Trimethyl-3- (dichloroacetyl) -1, 3-oxazolidine (R-29148, CAS 52836-31-4).

The active compounds A, B, C and D are known herbicides and safeners, see, for. B. The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 Volume 86, Meister Publishing Company, 2000; Hock, C. Fedtke, R.R. Schmidt, Herbicides, Georg Thieme Verlag, Stuttgart 1995; W.H. Ahrens, Herbicide Handbook, 7th Edition, Weed Science Society of America, 1994; and K.K. Hatzios, Herbicide Handbook, Supplement to the 7th Edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3- (dichloroacetyl) -1, 3-oxazolidine [CAS-No. 52836-31 -4] is also referred to as R-29148. 4- (Dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane [CAS # 71526-07-3] is also referred to as AD-67 and MON 4660. Further herbicidal active substances are known from WO 96/26202, WO 97/411 16, WO 97/411 17, WO 97/41 118 and WO 01/83459 and from W. Krämer et al. (ed.) "Modern Crop Protection Compounds", Vol. 1, Wiley VCH, 2007 and the literature cited therein. If the herbicides and / or safeners geometric isomers, eg. B. E / Z isomers to form, both the pure isomers and mixtures thereof can be used in the compositions of the invention. If the herbicides and / or safeners have one or more chiral centers and are therefore present as enantiomers or diastereomers, both the pure enantiomers and diastereomers and mixtures thereof can be used in the compositions according to the invention.

As far as the herbicides and / or the safeners have ionizable functional groups, they can also be used in the form of their agriculturally acceptable salts. In general, the salts of those cations or the acid addition salts of those acids come into consideration whose cations, or anions, do not adversely affect the action of the active ingredients.

Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, the alkaline earth metals, preferably of calcium and magnesium, and the transition metals, preferably of manganese, copper, zinc and iron, furthermore ammonium and substituted ammonium, in which one to four hydrogen atoms are replaced by C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl, preferably Ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2- (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-1 -yl) ammonium, benzyltrimethylammonium, benzyltriethylammonium, des further phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium such as trimethylsulfonium and sulfoxonium ions, preferably tri (C 1 -C 4 -alkyl) sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of Ci-C4-alkanoic acids, preferably Formate, acetate, propionate and butyrate. Such active compounds which have a carboxyl group can be used in the form of the acid, in the form of an agriculturally suitable salt but also in the form of an agriculturally acceptable derivative in the compositions according to the invention, e.g. as amides, such as mono- and di-C 1 -C 6 -alkylamides or arylamides, as esters, e.g. as allyl esters, propargyl esters, C 1 -C 10 -alkyl esters, alkoxyalkyl esters and thioesters, e.g. be used as Ci-Cio-alkylthioester. Preferred mono- and di-C 1 -C 6 -alkylamides are the methyl and the dimethylamides. Preferred arylamides are, for example, the anilides and the 2-chloroanilides. Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl) or isooctyl (2-ethylhexyl) esters. Preferred C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl esters are the straight-chain or branched C 1 -C 4 -alkoxyethyl esters, for example the methoxyethyl, ethoxyethyl or butoxyethyl esters. An example of the straight-chain or branched C 1 -C 10 -alkyl thioesters is the ethylthioester.

As used herein, the term "binary compositions" includes such compositions comprising one or more agents A (CBI) and one or more agents B (VLCFA inhibitors). Accordingly, the term "ternary compositions" includes those compositions which incorporate a or more CBI, one or more VLFA inhibitors, and one or more herbicides C and / or safener D.

In binary compositions which contain at least one CBI as component A and at least one VLCFA inhibitor B, the weight ratio of the active substances A: B is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and more preferably in the range of 1: 75 to 75: 1.

In ternary compositions containing both at least one CBI as component A, at least one VLCFA inhibitor B and at least one herbicide C and / or safener D, the relative proportions by weight of components A: B are as described above for binary combinations, Weight ratio of component a): c) usually in the range of 1: 1000 to 1000: 1, preferably in the range of 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and particularly preferably in the range from 1: 75 to 75: 1, and the weight ratio of components b): c) usually in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1 : 250 to 250: 1, and more preferably in the range of 1: 75 to 75: 1. Preferably, the weight ratio of Components a) + b) to component c) in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and particularly preferably in the range from 1: 75 to 75: 1.

Further preferred embodiments relate to ternary compositions which correspond to the binary compositions and which additionally comprise a safener D, in particular selected from benoxacor, cloquintocet, cyprosulfamide, dichloromethane, fenchlorazole, isoxadifen, mefenpyr, 4- (dichloroacetyl) -1-oxa-4- azaspiro [4.5] decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (R-29148, CAS 52836-31-4).

The combination of the active compounds A and B and their agriculturally useful salts are suitable - both as mixtures of isomers and in the form of pure isomers - as herbicides. They are suitable as such or as appropriately formulated agent. The herbicidal compositions containing combinations of the active compounds A and B, in particular the preferred embodiments thereof, combat plant growth on non-cultivated areas very well, especially at high application rates. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crops. This effect occurs especially at low application rates.

Depending on the particular application method, the combinations of active compounds A and B, in particular the preferred embodiments thereof, or agents containing them can be used in a further number of crop plants for the removal of undesirable plants. For example, the cultures mentioned in the introduction may be considered.

The term crops also includes those that have been modified by breeding, mutagenesis or genetic engineering methods. Genetically engineered plants are plants whose genetic material has been altered in a way that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information). As a rule, one or more genes are integrated into the genome of the plant in order to improve the properties of the plant. Furthermore, it has been found that the combination of the active compounds A and B is also suitable for the defoliation and / or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, come into consideration. In this regard, compositions for the desiccation and / or defoliation of plants, processes for the preparation of these agents and methods for the desiccation and / or defoliation of plants with the compounds of formula I have been found.

As desiccants, the compounds of the formula I are particularly suitable for drying out the aerial parts of crop plants such as potatoes, rape, sunflower me and soybean but also cereals. This enables a completely mechanical harvesting of these important crops.

Also of economic interest is harvest facilitation, which is made possible by the time-concentrated dropping or reducing the adhesion of the tree to citrus fruit, olives or other types and varieties of pome, stone and peel fruit. The same mechanism, i.e. promoting the formation of release webs between fruit or leaf and shoot part of the plants, is also essential for a well controllable defoliation of crops, especially cotton. In addition, shortening the time interval in which each cotton plant ripens leads to increased fiber quality after harvest.

The active compounds or the herbicidal compositions containing them can, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, atomizing, Dusting, scattering, pouring or treatment of the seed or mixing with the seed are applied. The forms of application depend on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.

The herbicidal compositions contain a herbicidally effective amount of at least one active substance A and at least one active substance B or an agriculturally useful salt thereof and auxiliaries customary for the formulation of pesticides.

Examples of the Formulation of Pesticides Commonly used auxiliaries are preferred auxiliaries, solid carriers, surface-active substances (such as dispersants, protective colloids, emulsifiers, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if necessary, dyes and for seed formulations adhesives.

Examples of thickeners (ie, compounds which impart modified flowability to the formulation, ie, high-level at low viscosity and low viscosity in the agitated state) are polysaccharides such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum ® (RT Vanderbilt) and organic and inorganic layer minerals such as Attaclay® (Engelhardt).

Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.

Bactericides may be added to stabilize the aqueous herbicidal formulation. Examples of bactericides are bactericides based on diclorophene and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS der Fa. Thor Chemie)

Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol. Examples of colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned under the names rhodamine B, Cl. Pigment Red 1 12 and Cl. Solvent Red 1 known dyes, and pigment blue 15: 4, pigment blue 15: 3, pigment blue 15: 2, pigment blue 15: 1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 1 12, pigment red 48: 1, pigment red 48: 1, pigment red 57: 1, pigment red 53: 1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108. Examples of adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and

Tylose.

Suitable inert additives are, for example: mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, eg. As amines such as N-methylpyrrolidone or water. Solid carriers are mineral soils such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.

As surface-active substances (adjuvants, wetting agents, adhesives, dispersants and emulsifiers), the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg lignosulfonic acids (eg Borrespers types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types , Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), as well as fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ethers, alkylarylpolyether alcohols, isotridecyl alcohol, fatty alcohol-ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl lether or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulfite deposits and proteins, denatured proteins, polysaccharides (eg methyl cellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), Polyalkoxylates, polyvinylamine (BASF SE, lupamine Types), polyethylenimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.

Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier. Granules, e.g. Coating, impregnation and homogeneous granules can by

Binding of the active ingredients to solid carriers are produced.

Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds of the formula I or Ia, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of active substance, wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil, which are suitable for dilution with water. The concentrations of the compounds of the formula I in the ready-to-use formulations can be varied within wide limits. The formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum). The combinations according to the invention can be formulated, for example, as follows:

1. Products for dilution in water A Water-soluble concentrates 10 parts by weight of active compound are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with 10 wt .-% active ingredient content.

B Dispersible Concentrates 20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion. The active ingredient content is 20% by weight

C Emulsifiable concentrates

15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (for example alkylaromatics) with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion. The formulation has 15% by weight active ingredient content.

D emulsions

25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (for example alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is added by means of an emulsifying machine (eg Ultraturax) in 30 parts by weight of water and a homogeneous emulsion brought. Dilution in water results in an emulsion. The formulation has an active ingredient content of 25% by weight.

E suspensions

20 parts by weight of active compound are comminuted with the addition of 10 parts by weight dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient. The active ingredient content in the formulation is 20% by weight. F Water-dispersible and water-soluble granules 50 parts by weight of active compound are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient. The formulation has an active ingredient content of 50% by weight. G Water-dispersible and water-soluble powders

75 parts by weight of active compound are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the formulation is 75% by weight. H gel formulations

In a ball mill, 20 parts by weight of the active ingredient, 10 parts by weight of the dispersant, 1 part by weight of the gelling agent and 70 parts by weight of water or an organic solvent are ground to a fine suspension. Dilution with water results in a stable suspension with 20% by weight active ingredient content. 2. Products for direct application

I dusts

5 parts by weight of active compound are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content. J Granules (GR, FG, GG, MG) 0.5 parts by weight of active compound are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content. K ULV solutions (UL) 10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent, e.g. XyIoI solved. This gives a product for direct application with 10% by weight of active ingredient content.

The application of the active substances or herbicidal compositions containing them can be carried out in the pre-emergence, post-emergence or together with the seed of a crop. It is also possible to apply the herbicidal compositions or active ingredients by pretreating with the herbicidal compositions or active ingredients. seed of a crop plant is applied. If the active ingredients are less compatible with certain crops, application techniques may be used in which the herbicidal agents are sprayed with the help of the sprayers so as not to hit the leaves of the sensitive crops as far as possible, while the active ingredients on the leaves below grow undesirable plants or the uncovered soil surface (post-directed, lay-by).

In a further embodiment, the application of the active ingredients or of the herbicidal agents can be carried out by treating seed.

The treatment of seed essentially comprises all techniques familiar to the skilled worker (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, and seed pelleting) based on the compounds according to the invention of the formula I or agents produced therefrom. Here, the herbicidal agents can be diluted or applied undiluted. The term seed includes seeds of all kinds, e.g. Grains, seeds, fruits,

Tubers, cuttings and similar forms. The term seed preferably describes grains and seeds here.

Seeds of the crops mentioned above, but also the seed of transgenic plants or plants obtained by conventional breeding methods, can be used as seed.

The required application rate of pure drug composition, i. A and B and optionally C / D without formulation auxiliaries, is dependent on the composition of the plant population, on the developmental stage of the plants, on the climatic conditions at the place of use and on the application technique. In general, the application rate of A and B and optionally C / D is 0.001 to 3 kg / ha, preferably 0.005 to 2.5 kg / ha and in particular 0.01 to 2 kg / ha of active substance (a.S.).

The required application rates of active substances A are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS

The required application rates of active substances B are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS

The required application rates of active substances C are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS

The required application rates of safeners D are generally in the range of 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1, 5 kg / h aS

The funds are fed to the plants primarily by foliar spraying. In this case, the application can, for example, with water as a carrier by conventional spraying techniques Spray mixture amounts of about 100 to 1000 l / ha (eg 300 to 400 l / ha) take place. Application of the herbicidal compositions in the so-called "low-volume" and "ultra-low-volume" method is just as possible as their application in the form of so-called microgranules The administration of the active substances or of the herbicidal compositions containing them can be carried out in the pre-emergence phase It is also possible to apply the compositions by applying seed of a crop plant pretreated with a composition according to the invention: If the active compounds A and B and, if appropriate, C are less compatible for certain crops Thus, application techniques may be used in which the herbicidal agents are sprayed with the help of the sprayers so that the leaves of the sensitive crops are not affected if possible, while the active ingredients on the leaves underneath growing unwanted plants or the uncovered Bodenflä (post-directed, lay-by).

In another embodiment, the application of the composition may be by treatment of seed.

The treatment of seed comprises essentially all techniques familiar to the person skilled in the art (seed dressing, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, and seed pelleting) based on the compounds according to the invention In this case, the herbicidal agents can be diluted or applied undiluted.

The term seed includes seeds of all kinds, e.g. Grains, seeds, fruits, tubers, cuttings and similar forms. The term seed preferably describes grains and seeds here.

Seeds of the abovementioned crops but also the seeds of transgenic or obtained by conventional breeding methods plants can be used as seeds. Depending on the control target, season, target plants and growth stage, the application rates of active ingredient are 0.001 to 3.0 kg / ha, preferably 0.01 to 1.0 kg / ha of active substance (a. For seed treatment, the compounds I are usually used in amounts of 0.001 to 10 kg per 100 kg of seed. In addition, it may be useful to mix, apply the active ingredients alone or in combination with other crop protection products, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with growth-regulating active ingredient groups. Also of interest is the miscibility with mineral salt solutions, which are used for the elimination of nutritional and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.

The active compounds and the compositions according to the invention may also have a plant-strengthening effect. They are therefore willing to mobilize zeneigener defenses against infestation by unwanted microorganisms, such as harmful fungi, but also viruses and bacteria. In this context, plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of treated plants in such a way that they develop extensive resistance to these microorganisms during subsequent inoculation with undesired microorganisms.

The active ingredients can be used to protect plants against attack by undesirable microorganisms within a certain period of time after the treatment. The period within which protection is induced generally extends to 1 to 28 days, preferably 1 to 14 days after treatment of the plants with the compounds I or after treatment of the seeds, up to 9 months after sowing.

The active compounds and the compositions according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.

The following examples serve to illustrate the invention.

Use Examples: The herbicidal action of the active substance combinations was demonstrated by greenhouse experiments:

The culture vessels used were plastic pots with loamy sand with about 5.8% humus as substrate. The seeds of the test plants were sown separately by species. In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing by means of finely distributing nozzles. The jars were lightly rained to promote germination and growth and then covered with clear plastic hoods until the plants had grown. This cover causes a uniform germination of the test plants, if it was not affected by the active ingredients. For the postemergence treatment, the test plants were grown depending on the growth form only to a stature height of 1, 5 to 15 cm and then treated with the suspended or emulsified in water agents. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.

The plants were kept species-specific at temperatures of 10 - 25 ° C and 20 - 35 ° C, respectively. The trial period lasted for 1 to 4 weeks. During this time, the plants were cared for, and their response to each treatment was evaluated. The rating was based on a scale of 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts and 0 no damage or normal growth course. A good herbicidal activity is at Wer- at least 70 and a very good herbicidal activity is given at values of at least 85.

The plants used in the greenhouse experiments are composed of the following species:

The results of these tests are given in the following Tables of Application Examples 1 to 9 and demonstrate the synergistic effect of mixtures containing at least one active ingredient A and at least one active ingredient B.

Here, a.S. = active substance, based on 100% active ingredient. The Colby values E are given in parentheses () in Application Examples 1 to 9.

Use Example 1: Synergistic herbicidal action of 1-1 with pre-emergence S-metolachlor

^* Drug 1-1 was used as 3S, 6S isomer. Use Example 2: Synergistic herbicidal action of I-9 with pre-emergence S-metolachlor

^* Agent I-9 was used as a 3S, 6S isomer.

Use Example 3: Synergistic herbicidal action of 1-10 with pre-emergence 2-10

^* The active ingredient 1-10 was used as a racemate.

Use Example 4: Synergistic herbicidal action of dichlobenil with dimethenamid-P in the pre-emergence process

Anwendungsbeispiel 6: Synergistische herbizide Wirkung von A-6 mit Pyroxasulfon im Vorauflaufverfahren

Use Example 6 Synergistic Herbicidal Action of A-6 with Pyroxasulfone in the Preemergence Process

Use Example 7: Synergistic herbicidal action of A-6 with dimethenamid-P in the pre-emergence process

Use Example 8 Synergistic Herbicidal Action of I-9 with Postemergence S-Metolachlor (GS 10)

Drug I-9 was used as 3S, 6S isomer. Use Example 9: Synergistic herbicidal action of 1-10 with post-emergence 2-10

Claims

claims 1. Herbicidal mixtures containing a) at least one active ingredient A from the group of cellulose biosynthesis inhibitors selected from chlorothiamide, dichlobenil, flupoxam, isoxaben, triaziflam, indaziflam, 1-cyclohexyl-5-pentafluorophenyloxy-1λ ⁴ - [1, 2,4,6] thiatriazine 3-ylamine and thaxomine derivatives of the formula I

wherein: R ^{a is} CN, CF ₃ or NO ₂ ; R ^{1 is} H or OH; A is phenyl or a five- or six-membered fully unsaturated ring which, in addition to carbon, may contain 1, 2 or 3 heteroatoms selected from O, N and S; and R ^2, R ³ H, OH, halogen, C -C alkyl or C ₄ -alkyl mean ₄ haloalkyl, and b) at least one active substance B from the group of VLCFA inhibitors selected from: b1) chloroacetamides such as acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metachlorlor-S, pethoxamide, pretilachlor, propachlor, B) acetanilides such as diphenamid, naproanilide and napropamide, b4) tetrazolinones such as fentrazamide, and b5) other VLCFA inhibitors such as anilofos, cafenstrol, piperophos, pyroxasulfone of formula 2:

wherein Y is phenyl or 5- or 6-membered heteroaryl as defined above, which may be substituted by one to three groups R; R is halogen, C 1 -C ₄ -alkyl, C 1 -C ₄ -alkoxy, C 1 -C ₄ -haloalkyl or Ci-C4-haloalkoxy; _R 2i _{i R} 22 _R 23 _R 24 _{H i is} halogen or C 1 -C ₄ -alkyl; X is O or NH; n O or i; means in synergistically effective amount. 2. Mixtures according to claim 1, which contain dichlobenil as active compound A. 3. Mixtures according to claim 1, which contain as active ingredient A isoxaben. 4. Mixtures according to claim 1, which contain Triaziflam as active ingredient A. 5. Mixtures according to claim 1, which contain as active ingredient A Indaziflam. 6. Mixtures according to claim 1, which contain as active ingredient A 1-cyclohexyl-5-pentafluorophenyloxy-1 λ ⁴ - [1, 2,4,6] thiatriazin-3-ylamine. 7. Mixtures according to claim 1, which contain as active ingredient A a thaxtomin derivative of the formula I. 8. Mixtures according to claim 7, which contain a thaxtomin derivative of the formula I, wherein A is phenyl or 2-thiophene and R ² and R ^{3 are} hydrogen. 9. Mixtures according to one of claims 1 to 8, which contain as active ingredient B a chloroacetamide. 10. Mixtures according to one of claims 1 to 8, which contain as active ingredient B an oxyacetanilide or an acetanilide. 1 mixtures according to any one of claims 1 to 8, which contain as active ingredient B a tetrazolinone or one of the other VLCFA-I inhibitors. 12. Mixtures according to one of claims 1 to 1 1, which contain a third active component c), which is selected from c) at least one herbicide C, selected from d) lipid biosynthesis inhibitors; c2) acetolactate synthase inhibitors (ALS inhibitors); c3) photosynthesis inhibitors; c4) protoporphyrinogen IX oxidase inhibitors; c5) bleacher herbicides; c6) enolpyruvyl-shikimate-3-phosphate synthase inhibitors (EPSP inhibitors); c7) glutamine synthetase inhibitors; c8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); c9) mitosis inhibitors; c10) decoupling herbicides; d 1) auxin herbicides; c12) auxin transport inhibitors; and c13) other herbicides selected from bromobutide, chlorofluorol, chlorofluorolmethyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metylsulfates, dimethipine, DSMA, dymron, endothal and its salts, etobenzanide, flamprop, flamprop -isopropyl, Flamprop-methyl, Flamprop-M-isopropyl, Flamprop-M-methyl, Flurenol, Flurenol-butyl, Flurprimidol, Fosamine, Fosamine-ammonium, Indano fan, maleic hydrazide, Mefluidide, Metam, methyl azide, Methylbro - mid, methyl dymron, methyl iodide, MSMA, oleic acid, oxaziclomefon, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphan and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol and its salts and esters; and Safenern D, selected from Benoxacor, Cloquintocet, Cyometrinil, Cyprosulfamide, Dichlormid, Dicyclo-non, Dietholate, Fenchlorazole, Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane and 2,2,5-trimethyl-3- (di-chloroacetyl) -1,3-oxazolidine. 13. A herbicidal mixture according to any one of the preceding claims, wherein the weight ratio of component A to component B is in the range of 100: 1 to 1: 100. Composition in the form of a plant protection composition formulated as a 1-component composition, comprising a mixture according to one of the preceding claims and at least one solid or liquid carrier and / or one or more surface-active substances. 15. A method for controlling undesired plant growth, which comprises allowing a herbicidally effective amount of a mixture according to one of claims 1 to 12 to act on plants, their habitat or seed.