WO1999057965A1 - Sulfonylurea-tolerant sugar beet mutants - Google Patents
Sulfonylurea-tolerant sugar beet mutants Download PDFInfo
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- WO1999057965A1 WO1999057965A1 PCT/EP1999/003348 EP9903348W WO9957965A1 WO 1999057965 A1 WO1999057965 A1 WO 1999057965A1 EP 9903348 W EP9903348 W EP 9903348W WO 9957965 A1 WO9957965 A1 WO 9957965A1
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H5/00—Angiosperms, i.e. flowering plants, characterised by their plant parts; Angiosperms characterised otherwise than by their botanic taxonomy
- A01H5/12—Leaves
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H6/00—Angiosperms, i.e. flowering plants, characterised by their botanic taxonomy
- A01H6/02—Amaranthaceae or Chenopodiaceae, e.g. beet or spinach
- A01H6/024—Beta vulgaris [beet]
Definitions
- the present invention relates to a process for the preparation of herbicide-tolerant cells, sulfonylurea-tolerant sugar beet mutants, processes for their preparation and processes for controlling unwanted vegetation in crops of sulfonylurea-tolerant sugar beet mutants.
- herbicidal agents e.g. Sulfonylureas
- Sulfonylureas for controlling undesirable plant growth in crops
- herbicides are widely used in agriculture.
- the possibility of controlling the harmful plants by the herbicides is not always satisfactory.
- highly effective herbicides are applied to control harmful plants, the growth of crops is often impaired. For this reason, herbicide-tolerant crops are of particular interest for agriculture.
- EP-A-0360750 describes e.g. the production of AHAS inhibitor-tolerant plants by selection or by genetic engineering.
- the herbicide tolerance of the plants to certain ortho-substituted N-arylsulfonyl-N'-pyrimidinyl ureas is generated here by an increased AHAS content in the plants.
- ßtSl ibUNGSKÜPIE which have been obtained by selection processes and have, inter alia, a tolerance to chlorosulfuron, bensulfuron, chlorimuron, thifensulfuron and sulfometuron.
- US 5,013,659; US 5,141, 870 and US 5,378,824 the introduction of a modified acetolactate synthase (ALS) gene from yeast in sugar beets by means of genetic engineering processes and the production of herbicide-tolerant plant mutants based on this resistance principle on appropriate herbicide-containing nutrient media.
- Saunders et al. (Crop Science, 1992, 32, 1317-1320) described the production of sulfonylurea-resistant sugar beet by somatic cell selection.
- WO 98/02527 also mentions sugar beets which are resistant to certain sulfonylureas and herbicides of the imidazolinone type.
- the principle of resistance described in WO 98/02527 is based on two point mutations within the ALS gene in positions 337 and 562, which lead to the amino acid substitutions Ala 113 Thr and Pro 188 Ser in the enzyme.
- sugar beet mutants described to date in the prior art do not always enable adequate control of all harmful plants or do not always show a satisfactory tolerance towards newer sulfonylurea herbicide generations, in particular one or more sulfonylurea herbicides from group A, consisting of
- Q is oxygen, sulfur or -N (R 4 ) -; Y is CH or N;
- R is hydrogen (H), (C 1 -C 12 ) alkyl; (C 2 -C 10 ) alkenyl; (C 2 -C 10 ) alkynyl; (C r C 6 ) - alkyl, which is one to four times by residues from the group halogen, (C, - ⁇ ) -
- Halogen group (C 1 -C 4 ) alkyl, (C 1 -C 4 alkoxy, (C r C 4 ) haloalkyl, (C, -C 4 ) thioalkyl, (C 2 -C 5 ) alkoxycarbonyl, ( C 2 -C 5 ) -alkylcarbonyloxy, carbonamide, (C 2 -C 5 ) -alkylcarbonylamino, (C 2 -C 5 ) -alkylaminocarbonyl, di - [(C 1 -C 4 ) -aikyl] - carbonyl and nitro or a radical of the formulas A-1 to A-10
- R 1 is hydrogen or (CC 3 ) alkyl
- R 2 is hydrogen, halogen, (C 1 -C 3 ) -alkyl or (C r C 3 ) -alkoxy, the latter two radicals being unsubstituted or substituted by one or more halogen or (CC 3 ) -alkoxy groups;
- R 3 is hydrogen, halogen, (C r C 3 ) -alkyl, (C 1 -C 3 ) -alkoxy or (C r C 3 ) -alkylthio, the abovementioned alkyl-containing radicals being unsubstituted or singly or multiply by halogen or mono- or are substituted twice by (C 1 -C 3 ) alkoxy or (C 1 -C 3 ) alkylthio; or a radical of the formula NR 5 R 6 , (C 3 -C 6 ) cycloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 4 ) alkenyloxy or (C 3 - C 4 ) alkynyloxy;
- R 4 is hydrogen, (C r C 4 ) alkyl or (C 1 -C 4 ) alkoxy and
- R 5 and R 6 are independently hydrogen, (C 1 -C 4 ) alkyl, (C 3 -C 4 ) alkenyl, (C 1 -C 4 ) haloalkyl or (CC 4 ) alkoxy;
- R 2 and R 3 are independently H or (C r C 4 ) alkyl;
- R 5 (C r C 4 ) alkylsulfonyi, CHO, [(C r C 4 ) alkyl] carbonyl which is unsubstituted or substituted by one or more halogen atoms, [(C 1 -C 4 ) alkoxy] oxalyl, [( C 3 -C 6 ) cycloalkyl] carbonyl or a group of the formula WWW
- W is an oxygen or sulfur atom (O or S);
- R 9 H, (C 1 -C 4 ) alkyl which is unsubstituted or by one or more halogen atoms or by (C 1 -C 4 ) alkoxy, ( ⁇ -C ⁇ alkylthio, [(C 1 -C 4 ) alkoxy] - carbonyl and [(C 1 -C 4 ) alkyl] carbonyl is substituted, R 10 and R 11 independently of one another are H, (C 1 -C 4 ) alkyl which is unsubstituted or substituted by one or more halogen atoms, or (C 3 -C 4 ) alkenyl or (C 3 -C 4 ) alkynyl, where at least one of the radicals R 10 and R 1 is different from hydrogen; the radicals R 12 together with the N atom form a heterocyclic ring with 5 or 6 ring members, which is another heteroatom from the group N, O and S in can contain the various oxidation states and is unsubstitute
- Halogen atoms is substituted, or (C 3 -C 4 ) alkenyl or (C 3 -C 4 ) alkynyl; A3) Compounds of the general formula III, their N-oxides and their inorganic or organic salts
- Halogen is substituted, (C r C 4 ) alkoxy, (CC 4 ) alkylthio;
- R 2 is H or methyl
- R 3 is methyl or methoxy
- R 4 H (C 1 -C ⁇ ) alkyl which is unsubstituted or one or more times by halogen
- Alkylthio is substituted
- R 9 Rio. Marg. R12.
- R 25 > R 26 and R 27 are each independently H, (CC 4 ) alkyl, (C 3 -C 6 ) alkenyl or (C 3 -C 6 ) alkynyl; or
- R 10 and R 20 each independently of one another are the groups -C (O) -X 5 - (CC 4 ) -alkyl or -C (O) - (CC 4 ) -alkyl, which can be partially substituted by halogen; or R 10 and R ⁇ or R 12 and R 13 or R 16 and R 17 or R 20 and R 21 or R 23 and R 24 or R 25 and R 9 or R 26 and R 27 together form a (C 4 -C 5 ) Form alkylene chain, which may be partially interrupted by oxygen or NR 14 , wherein R 14 is H, (CC 4 ) alkyl, (C 3 -C 6 ) alkenyl or (C 3 -C 6 ) alkynyl; R 15 and R ⁇ are each independently of one another (C ⁇ C -alkyl or (C 1 -C 4 ) haloalkyl; R 18 and R 30 are each independently substituted by COOR 28 (C ⁇ C-alkyl; R 19.
- ⁇ And R 28 each independently of one another H or (C 1 -C 4 ) alkyl, X, and X 3 each independently of one another S, SO or SO 2 ; X 2 and X 4 each independently of one another O or S and X 5 O or NR 14 ; A4) amidosulfuron (21, p.37); A5) ethoxysulfuron (287, p.488); A6) triasulfuron (723, p.1222);
- the object of the present invention is to overcome these disadvantages.
- the object is achieved by the present invention by providing sugar beet mutants which, compared to one or more sulfonylureas of the abovementioned (above) general formulas I to III, amidosulfuron, ethoxysulfuron, triasulfuron, metsulfuron, tribenuron, flupyrsulfuron, nicosulfuron, rimsulfuron, sulfosulfuron, sulfosuron , Oxasulfuron, etametsulfuron, imazosulfuron and / or compounds of the above Formula V has a very good tolerance, ie a high tolerance.
- Another object of the present invention is also to improve methods for controlling unwanted plant growth in the sugar beet crops according to the invention.
- sugar beet mutants By selection on nutrient media containing sulfonylurea, in particular nutrient media additionally containing safeners, sugar beet mutants have now been found which surprisingly have the desired resistance to sulfonylurea herbicides of the general formulas I to III, amidosulfuron, ethoxysulfuron triasulfuron, metsulfuron, tribenulfuron, flupyrsulfuron, flup Prosulfuron, sulfosulfuron, oxasulfuron, etametsulfuron, imazosulfuron and / or compounds of the above Have formula V.
- sugar beet mutants according to the invention have further surprising advantages, for example by are promoted by the said sulfonylureas in their growth or a changed content of
- Carbohydrates or nitrogen-containing compounds e.g. amino acid content, proteins.
- the present invention also has other advantages because it enables a broader spectrum of
- Harmful plants in the sugar beet crops according to the invention so that a faster and safer activity against the harmful plants and / or considerably simplified control of the harmful plants is made possible, for example by requiring a single or only a few applications.
- the post-emergence application is particularly preferred, particularly in the period between the cotyledon and 12-leaf stage of the harmful plants and / or in the period between piercing the sugar beets and their 12-leaf stage.
- the present invention therefore relates to sulfonylurea tolerants
- Sugar beet mutants their seeds or propagation material and their cells, selected from group A consisting of one or more sulfonylureas
- prosulfuron (613, p.1041)
- sulfosulfuron (668, p.1130)
- sulfonylureas selected from group A consisting of A1 to A18.
- the sulfonylurea-tolerant sugar beet mutants, their seeds or propagation material and their cells can e.g. through conventional crossing methods, in addition to the feature of the sulfonylurea resistance according to the invention, also have a further herbicide resistance (e.g. against glufosinates or glyphosates) or contain a further genetic modification, e.g. be modified by the introduction of insect, fungus or virus resistance (eg by expression of a Bt toxin, a chitinase, glucanase) or also in their metabolic properties, so that a qualitative and / or quantitative change in ingredients (eg the energy carbohydrate -, fatty acid or nitrogen metabolism or with the
- plant mutants or cell lines can also be selected by e.g. Seed or cell cultures (callus or suspension cultures) are grown in a suitable medium in the presence of increasing herbicide concentrations.
- a suitable mutagen see e.g. US 4,443,971
- Another object of the present invention is also a method for the selection of herbicide-tolerant cells (mutants), preferably of eu or prokaryotic cells, in particular those from plants, bacteria or yeasts, by cultivating said cells in the presence of at least one herbicidally active compound and at least a safener under suitable conditions.
- the method according to the invention for the selection of herbicide-tolerant mutants leads to an improved quality and / or quantity of the herbicide-resistant cells, in particular when selecting in the presence of herbicide concentrations which are> 50%, preferably> 90%, particularly preferably> 95 % and very particularly preferably> 99% are lethal for the respective cell population.
- a particularly suitable method for qualitatively and / or quantitatively improving the mutant yield consists, for example, of cells, preferably cell suspensions, in the presence of one or more herbicides and one or more safeners in a concentration range from 10 "3 M to 10 '7 M, preferably in the range of 10 "4 M to 10 " 6 M to treat and after a period of about a day to 2 weeks, preferably about 3-10 days, for example a week, the cells with fresh cell culture medium without herbicide, but with safener and continue this subculture step for about 3-5 cycles.
- the cell suspensions are then applied, for example, to agar media with the respective herbicidal active ingredient (in the concentration range from 10 "3 M to 10" 7 M, preferably 10 "4 M to 10 " 6 M) with and without safener (in the concentration range 10 "3 M to 10 7 M, preferably 10 "4 M to 10 " 6 M.
- the concentration ratio of safener to herbicidal active ingredient in the mixture can differ in a ratio of 100: 1 to 1: 100, preferably in the range 10: 1 to 1: 10.
- the herbicide-resistant cell clones can be transferred to fresh selection medium, either maintaining the herbicide concentration or by a factor of 2-100, preferably around by a factor of 2 to 10.
- Plant mutants with a herbicide resistance that is significantly higher than that of wild-type cells are used for the subsequent plant regeneration utanten subcultivated on / in culture media which have the content of cytokinins and / or auxins necessary for the respective genotype.
- Plant regeneration can be carried out in the presence or absence of a herbicide or, if appropriate, a herbicide / safener mixture.
- safener means a compound by means of which the damage to a crop plant possibly caused by a herbicide can be reduced or avoided.
- suitable safeners are those which, in combination with sulfonylurea herbicides, preferably phenylsulfonylureas, have a safener action.
- Suitable safeners are known from WO-A-96/14747 and the literature cited therein.
- the following groups of compounds are suitable, for example, as safeners for the herbicidal active compounds (A) mentioned above: a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type, preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester, and related compounds as described in WO 91/07874, b) derivatives of dichlorophenylpyrazole carboxylic acid, preferably Compounds such as ethyl 1 - (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate,
- active substances of the phenoxyacetic or propionic acid derivative or aromatic carboxylic acid type e.g. 2,4-dichlorophenoxyacetic acid (ester) (2,4-D), 4-chloro-2-methylphenoxy-propionester (mecoprop), MCPA or 3,6-dichloro-2-methoxy-benzoic acid (ester) (dicamba) .
- an object of the present invention is a method for producing sulfonylurea-tolerant plants by cultivation on / in a sulfonylurea-containing nutrient medium in the presence of a suitable safener, by a) selecting callus or cell suspension cultures while maintaining their embryogenic and morphogenic competence, b) the cultures obtained under a) are cultivated and selected on / in a sulfonylurea-containing nutrient medium and c) intact plants are regenerated from the cultures obtained under b).
- Another object of the present invention is a
- Process for producing the sugar beet mutants according to the invention by culturing on / in a sulfonylurea-containing nutrient medium, preferably in the presence of a suitable safener, by a) selecting callus or cell suspension cultures while maintaining their embryogenic and morphogenic competence, b) the cultures obtained under a) on / cultivated and selected in a nutrient medium containing sulfonylurea and c) intact plants are regenerated from the cultures obtained under b).
- an object of the invention is the use of sugar beet mutants according to the invention which can be obtained by the process according to the invention in agriculture, e.g. as animal feed or for the food industry, especially for sugar production.
- Yet another object of the present invention is also a method for controlling undesirable plant growth in crops of the sugar beet mutants according to the invention, characterized in that one or more sulfonylureas selected from group A consisting of A1 are added to the plants, their seeds or propagation material or their cultivated area to A18, optionally in combination with one or more herbicides selected from group B consisting of B1) herbicides from the class of the imidazolinones, preferably imazethapyr (415, p. 701), imazamethapyr (2, p.
- imazapyr 413, p.697), imazaquin (414, p.699), imazamox (412, p.696);
- herbicides from the class of inhibitors of photosynthetic electron transport preferably biscarbamates, particularly preferably phenmedipham (563, p.948), desmedipham (206, p.349);
- B3) a herbicide from the class of the PPO inhibitors for example the diphenyl ether or the azoles, preferably Azifluorfen (7, S.12), Oxyfluorfen (547, S.919), Pyraflufen (617, S.1048), Carfentrazone (112 , P.191), lactofen (442, p.747), nitrofen (S1193, p.1343), oxadiargyl (538, p.904), fluoroglycofen (344, p.580), sulfentrazone (665, p.1126) or also a CF 3 uracil of the formula IV as disclosed in US Pat. No. 5,183,492: Formula IV:
- HPPDO hydroxyphenyl pyruvate dioxygenase
- B4 a herbicide from the class of the hydroxyphenyl pyruvate dioxygenase (HPPDO) inhibitors, e.g. the triketones, preferably isoxaflutole (436, p.737), isoxachlortole (RPA-201735) or sulcotrione (664, p.1124);
- B5 a herbicide from the class of herbicidally active, optionally synthetic auxins or their transport inhibitors, preferably Quinmerac (636, S.1080), clopyralide (153, S.260), diflufenzopyr (50, S.81, BAS 65400H);
- B6) a herbicide from the class of lipid or fatty acid synthesis inhibitors, preferably aryloxyphenoxycarboxylic acids or cyclohexanedione oximes, particularly preferably fenoxaprop (309, p.
- B8) a herbicide from the class of 5-enolpyruvylshikimate-3-phosphate synthase inhibitors, preferably glyphosate (383, p. 646); B9) a herbicide from the class of benzofuranylalkanesulfonates, preferably ethofumesate (285, p.484) or herbicidal compositions containing these active ingredients from group A or B can be applied simultaneously or in succession.
- an object of the invention is also the use of one or more sulfonylureas selected from group A (A1 to A18) as defined, optionally in combination with one or more herbicides selected from group B, consisting of B1 to B9, or containing them Herbicidal agents on the areas under cultivation of sugar beet crops according to the invention.
- the active substances mentioned under A1 to A18 and under B1 to B9 include both their racemic mixtures and their active enantiomers.
- the salts of the active ingredients mentioned under A1 to A18 and under B1 to B9 with organic or inorganic acids or bases are included, provided that they are salt formers.
- the esters of the active ingredients mentioned under A1 to A18 and under B1 to B9 are also included, if they are herbicidally active.
- the advantages are e.g. in a positive growth regulatory effect, a reduced number of applications or a reduction in the application rates (compared to the conventional use of herbicides), a generally good biodegradability, a low burden in post-cultivation and / or good protection of beneficial organisms.
- herbicidal active ingredients from group A i.e. sulfonylureas A1 to A18
- herbicides from group B i.e. herbicides B1 to B9
- herbicide-tolerant means that the herbicide-tolerant sugar beet mutants are present in the presence of a or several sulfonylureas of group A, possibly in combination with one or more herbicides of group B, do not show any apparent impairment of their physiological functions, the same sulfonylureas showing non-tolerant plants, a growth-impairing or phytotoxic effect.
- the type and extent of herbicide tolerance depend on the particular herbicide, the respective dosage and general growth conditions.
- the sugar beet mutants, their seeds or propagation material or their cells particularly preferably have a tolerance to compounds of the general formula I in a concentration range of 0.5-40, in particular 1-20 and very particularly 3-10 g ai / ha, to compounds of the general formula II in a concentration range of 1-40, in particular 2-20 and very particularly 6-10 g ai / ha, compared to compounds of the general formula III in a concentration range of 0.5-50, in particular 1-25 and very particularly 3-12.5 g ai / ha, compared to amidosulfuron in a concentration range of 1-60, in particular 2-30 and very particularly 6-15 g ai / ha, compared to ethoxysulfuron in a concentration range of 5-120, especially 10-60 and very particularly 20-30 g ai / ha, compared to triasulfuron in a concentration range of 1-80, in particular 2-40 and very particularly 6-20 g ai / ha, compared to metsulfuron in a concentration range of
- seed or propagation material includes both vegetative and sexual propagation material such as fruits, seeds, tubers, rhizomes, seedlings, cuttings, calli, protoplasts, cell cultures etc.
- sugar beet is not only to be understood as whole plants which can be obtained or produced by selection, but also, if appropriate, their parts such as roots, leaves, stems, tubers and other cell assemblies and generations or cells derived from these plants.
- sulfonylurea-resistant sugar beet mutants according to the invention can also be found in e.g. transgenic sugar beets are crossed using conventional breeding methods known to those skilled in the art.
- transgenic plants which can be particularly preferred, for example, for a cross, are generally distinguished by particularly advantageous properties, for example by an increased yield, resistance to certain pesticides, especially to certain herbicides or insect pests, resistance to plant diseases or pathogens such as certain insects or mites or microorganisms such as fungi, bacteria or viruses.
- Other properties concern e.g. B. also the crop in terms of quantity, quality, shelf life, composition or special ingredients.
- transgenic plants which have modified properties compared to previously naturally occurring plants exist, for example, in the use of genetic engineering processes (see, for example, EP-A-0221044, EP-A-0131624 ).
- genetic engineering processes see, for example, EP-A-0221044, EP-A-0131624 .
- the production of genetically modified plants with respect to modifications of the vegetable carbohydrate metabolism e.g. WO 94/28146, WO 92/11376, WO 92/14827, WO 91/19806
- resistance to certain herbicides e.g. of the glufosinate type (see e.g. EP-A-0242236, EP-A-242246) or glyphosate (e.g.
- WO 92/00377 resistance to certain pests, e.g. due to the ability to produce certain Bacillus thuringiensis toxins (Bt toxins) or protease inhibitors (e.g. EP-A-0142924, EP-A-0193259).
- Bt toxins Bacillus thuringiensis toxins
- protease inhibitors e.g. EP-A-0142924, EP-A-0193259
- transgenic sugar beet with an altered sucrose content through modifications of the gene expression of the enzymes ADP-glucose pyrophosphorylase, sucrose phosphate synthase and sucrose synthase are known from WO 94/28146.
- a wide range of economically important monocotyledonous and dicotyledonous harmful plants can be combated excellently with the methods according to the invention for controlling (controlling) undesired plant growth.
- Perennial weeds which are difficult to control and which sprout from rhizomes, rhizomes or other permanent organs are also recorded with excellent results. It does not matter whether the substances or agents are used in pre-sowing,
- the spectrum of activity extends to species such as Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Matricaria, Abutilon, Polygonum, Galinsoga, Mercurialis, Solanum, Chinopodium, Kochia, Anthemis and Sonchus on the annual side as well as Convolvulus, Cirsium and Rumex for the perennial weeds and also crops such as Potato, rapeseed etc.
- the existing growth stage stands or dies completely after a certain time, so that weed competition which is harmful to the crop plants is eliminated very early and sustainably.
- the herbicidal active compounds or combinations thereof by suitable application of the herbicidal active compounds or combinations thereof, the following harmful plants, such as Anthemis, agropyron, Chinopodium, cirsium, kochia, polygonum, matriciaria, as well as growth / failure crops and generally weeds in later growth stages well, ie preferably> 80% and especially> 90% to be controlled.
- harmful plants such as Anthemis, agropyron, Chinopodium, cirsium, kochia, polygonum, matriciaria, as well as growth / failure crops and generally weeds in later growth stages well, ie preferably> 80% and especially> 90% to be controlled.
- the compounds or agents used in the process according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations and can be formulated in various ways, depending on the biological and / or chemical-physical parameters specified are.
- Possible formulation options include: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator - and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
- WP wettable powder
- SP water-soluble powder
- EC emulsifiable concentrates
- EW emulsions
- SC Suspension concentrates
- SC dispersions based on oil or water, oil-
- combinations with other pesticidally active substances e.g. Apply insecticides, acaricides, fungicides, safeners, fertilizers and / or growth regulators, e.g. in the form of a finished formulation or as a tank mix.
- the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 1 to 95% by weight, of active ingredients or their salts.
- the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation ingredients.
- the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight.
- Dust-like formulations contain 1 to 30, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
- the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used.
- the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
- active ingredient formulations mentioned may contain the usual adhesive, wetting, dispersing, emulsifying, penetrating,
- Preservatives Preservatives, antifreeze and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH value and viscosity influencing means.
- the herbicidal combination partners of group B (B1 to B9) with the sulfonylureas of group A (A1 to A18) can be used in mixture formulations or in a tank mix, for example known active compounds, such as those e.g. in Weed Research 26, 441-445 (1986) or "The Pesticide Manual", 11th edition, The British Crop Protection Council, 1997, Bracknell, England, and the literature cited therein.
- the individual compounds listed under A4 to A17 and B1 to B9 are generally designated with the "common name" according to the International Organization for Standardization (ISO).
- the formulations present in the commercial form are optionally diluted in the customary manner, e.g. in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water, and then applied to the plants, parts of plants or the agricultural soil on which the plants stand or in which they grow or are present as seeds.
- Preparations in the form of dust, ground granules or scattering granules and sprayable solutions are usually no longer diluted with other inert substances before use.
- the required application rate of the herbicidal compounds varies within wide limits, e.g. between 0.001 and 10.0 kg / ha or more of active substance, but it is preferably between 0.005 and 5 kg / ha.
- Example 1 Establishment of morphogenic sugar beet cell cultures on amino acid-free nutrient medium
- Ripe sugar beet seeds were germinated after the disinfection of the seed surface on hormone-free medium under aseptic conditions.
- the modified Murashige-Skoog medium (MS medium) used for the experiments is shown in Table 1.
- the pH of the medium was adjusted to 5.8 before autoclaving.
- the vitamins were added to the medium before autoclaving (120 ° C; 15 min).
- the phytohormone concentrations were varied for callus initiation, callus subculture and plant regeneration as described in the text.
- the explants were cultivated on MS medium with a content of 0.05-0.5 mg naphthylacetic acid per liter medium at 25 ⁇ 2 ° C in a 12 hour light / dark rhythm at approx. 500-2000 lux. Under these conditions, explants from some seedlings formed morphogenic callus within 2-3 weeks, which could be subcultured on the respective medium for months while maintaining its regenerative capacity.
- Example 2 In vitro mutagenesis
- Morphogenic sugar beet callus pieces are in MS medium with 0.1 to 1% ethyl methanesulfonate for 10 to 120 min. incubated, washed 3 times and cultivated in the medium. The surviving morphogenic callus segments are subcultured on fresh medium after 2 to 4 weeks. After a further 2 to 4 weeks, the calli can be used for selection experiments.
- calli are transferred to the herbicidal (LD 98 ) agar media (0.8% agar) and evaluated after 6 to 8 weeks.
- the Petri dishes are incubated at 12 to 2000 lux and 25 ° C per day. Calli are formed in the media with the herbicides, which grow with the formation of shoot primordia.
- Example 5 Selection of sulfonylurea tolerant sugar beet mutants in the presence of herbicide and safener.
- the cells were washed twice with safener-free and herbicide-free medium, taken up in 20 ml of MS medium and plated out on agar medium.
- the agar medium contained MS salts, vitamins and usual trace elements, 20 g sucrose, 0.8% agar, 0.5 mg / l BAP and 0.5 mg / l 2.4.-D pH 5.8.
- the following additives were added to the medium:
- the herbicide-tolerant cell clones were induced on regeneration medium (MS medium with 1 mg / l BAP and 0.05 mg / l naphthylphenoxyacetic acid (NAA)) for sprout formation.
- the in vitro shoots were induced on medium with 0.05 mg / l NAA in a second step for root formation.
- the rooted plants could be transferred into soil after approx. 8 - 12 weeks.
- Example 6 Herbicide Application In the 4th and 5th leaf stages, the plants are sprayed with herbicide solutions in customary application rates. The herbicides are applied as 0.1 to 1% aqueous solutions. The treated plants are rated visually after 14 to 28 days. The test for herbicide resistance is carried out under conditions which lead to serious damage (degree of damage> 80%) in commercial (control plants).
- the regenerated plants show a good tolerance towards the applied sulfonylureas, i.e. comparatively little damage.
- herbicidal effectiveness is assessed at intervals of 3-6 weeks as the growth progresses in order to assess the selectivity of the various active compounds and their herbicidal activity.
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Abstract
The invention relates to a method for producing herbicide-tolerant cells, to sulfonylurea-tolerant sugar beet mutants, to a method for the production thereof, and to a method for combating unwanted plant growth in cultures of sulfonylurea-tolerant sugar beet mutants.
Description
Sulfonylhamstoff-tolerante ZuckerrübenmutantenSulphonylurea-tolerant sugar beet mutants
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung Herbizid-toleranter Zellen, Sulfonylhamstoff-tolerante Zuckerrübenmutanten, Verfahren zu deren Herstellung sowie Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs in Kulturen von Sulfonylhamstoff-toleranten Zuckerrübenmutanten.The present invention relates to a process for the preparation of herbicide-tolerant cells, sulfonylurea-tolerant sugar beet mutants, processes for their preparation and processes for controlling unwanted vegetation in crops of sulfonylurea-tolerant sugar beet mutants.
Die Verwendung von herbiziden Wirkstoffen, z.B. Sulfonylharnstoffen, zur Kontrolle von unerwünschtem Pflanzenwuchs in Nutzpflanzenkulturen ist in der Landwirtschaft weit verbreitet. Hierbei besteht häufig das Problem, daß die Kontrollmöglichkeit der Schadpflanzen durch die Herbizide nicht immer befriedigend ist. Werden hochwirksame Herbizide appliziert, um die Schadpflanzen zu bekämpfen, wird oftmals auch das Wachstum der Nutzpflanzenkulturen beeinträchtigt. Aus diesem Grunde sind herbizid-tolerante Nutzpflanzen für die Landwirtschaft von besonderem Interesse.The use of herbicidal agents, e.g. Sulfonylureas, for controlling undesirable plant growth in crops, are widely used in agriculture. Here there is often the problem that the possibility of controlling the harmful plants by the herbicides is not always satisfactory. If highly effective herbicides are applied to control harmful plants, the growth of crops is often impaired. For this reason, herbicide-tolerant crops are of particular interest for agriculture.
Es sind bereits mehrfach Zuckerrüben beschrieben worden, die eine Toleranz gegenüber herbiziden Wirkstoffen, beispielsweise Sulfonylhamstoffe, Imidazolinone oder Inhibitoren des Enzyms Acetohydroxysäure Synthase (AHAS), aufweisen:Sugar beets have been described several times, which have a tolerance to herbicidal active ingredients, for example sulfonylureas, imidazolinones or inhibitors of the enzyme acetohydroxy acid synthase (AHAS):
Die EP-A-0360750 beschreibt z.B. die Herstellung von AHAS-lnhibitor-toleranten Pflanzen durch Selektion oder durch gentechnische Verfahren. Die Herbizid- Toleranz der Pflanzen gegenüber bestimmten ortho-substituierten N-Aryl-sulfonyl- N'-Pyrimidinylhamstoffen (Chlorsulfuron, Sulfometuronmethyl, Triasulfuron u.a.) wird hierbei durch einen erhöhten AHAS-Gehalt in den Pflanzen erzeugt.EP-A-0360750 describes e.g. the production of AHAS inhibitor-tolerant plants by selection or by genetic engineering. The herbicide tolerance of the plants to certain ortho-substituted N-arylsulfonyl-N'-pyrimidinyl ureas (chlorosulfuron, sulfometuronmethyl, triasulfuron, etc.) is generated here by an increased AHAS content in the plants.
US 5,198,599 beschreibt Sulfonylhamstoff- und Imidazolinon-tolerante Pflanzen,US 5,198,599 describes sulfonylurea- and imidazolinone-tolerant plants,
ßtSl ibUNGSKÜPIE
die durch Selektionsverfahren gewonnen wurden und u.a. eine Toleranz gegenüber Chlorsulfuron, Bensulfuron, Chlorimuron, Thifensulfuron und Sulfometuron aufweisen.ßtSl ibUNGSKÜPIE which have been obtained by selection processes and have, inter alia, a tolerance to chlorosulfuron, bensulfuron, chlorimuron, thifensulfuron and sulfometuron.
Desweiteren beschreiben US 5,013,659; US 5,141 ,870 und US 5,378,824 die Einführung eines modifizierten Acetolactat-Synthase (ALS)-Gens aus Hefe in Zuckerrüben mittels gentechnischer Verfahren sowie die Herstellung von auf diesem Resistenzprinzip beruhenden, Herbizid-toleranten pflanzlichen Mutanten auf entsprechenden Herbizid-haltigen Nährmedien. Darüber hinaus wird von Saunders et al. (Crop Science, 1992, 32, 1317-1320) die Herstellung von Sulfonylharnstoff-resistenten Zuckerrüben durch somatische Zellselektion geschildert.Furthermore, US 5,013,659; US 5,141, 870 and US 5,378,824 the introduction of a modified acetolactate synthase (ALS) gene from yeast in sugar beets by means of genetic engineering processes and the production of herbicide-tolerant plant mutants based on this resistance principle on appropriate herbicide-containing nutrient media. In addition, Saunders et al. (Crop Science, 1992, 32, 1317-1320) described the production of sulfonylurea-resistant sugar beet by somatic cell selection.
In WO 98/02527 werden außerdem Zuckerrüben genannt, die gegenüber bestimmten Sulfonylharnstoffen und Herbiziden vom Imidazolinon-Typ resistent sind. Das in der WO 98/02527 beschriebene Resistenzprinzip beruht dabei auf zwei Punktmutationen innerhalb des ALS-Gens in den Positionen 337 und 562, die zu den Aminosäuresubstitutionen Ala113Thr und Pro188Ser in dem Enzym führen.WO 98/02527 also mentions sugar beets which are resistant to certain sulfonylureas and herbicides of the imidazolinone type. The principle of resistance described in WO 98/02527 is based on two point mutations within the ALS gene in positions 337 and 562, which lead to the amino acid substitutions Ala 113 Thr and Pro 188 Ser in the enzyme.
Die bislang im Stand der Technik beschriebenen Zuckerrübenmutanten ermöglichen jedoch nicht immer eine ausreichende Bekämpfung aller Schadpflanzen bzw. zeigen nicht immer eine befriedigende Toleranz gegenüber neueren Sulfonylhamstoff-Herbizid Generationen, insbesondere einem oder mehreren Sulfonylhamstoff-Herbiziden der Gruppe A, bestehend ausHowever, the sugar beet mutants described to date in the prior art do not always enable adequate control of all harmful plants or do not always show a satisfactory tolerance towards newer sulfonylurea herbicide generations, in particular one or more sulfonylurea herbicides from group A, consisting of
A1 ) Verbindungen der Formel (I) und deren anorganische oder organische Salze,
A1) compounds of the formula (I) and their inorganic or organic salts,
worinwherein
Q Sauerstoff, Schwefel oder -N(R4)-; Y CH oder N;Q is oxygen, sulfur or -N (R 4 ) -; Y is CH or N;
R Wasserstoff (H), (C1-C12)-Alkyl; (C2-C10)-Alkenyl; (C2-C10)-Alkinyl; (CrC6)- Alkyl, das ein- bis vierfach durch Reste aus der Gruppe Halogen, (C,-^)-R is hydrogen (H), (C 1 -C 12 ) alkyl; (C 2 -C 10 ) alkenyl; (C 2 -C 10 ) alkynyl; (C r C 6 ) - alkyl, which is one to four times by residues from the group halogen, (C, - ^) -
Alkoxy, (C C4)-Thioalkyl, CN, (C2-C5)-Alkoxycarboπyl und (C2-C6)-Alkenyl substituiert ist; oder (C3-C8)-Cycloalkyl, das unsubstituiert oder durch Reste aus der Gruppe (CrC4)-Alkyl, (C1-C4)-Alkoxy, (CrC4)-Alkylthio und Halogen substituiert ist; (C5-C8)-Cycloalkenyl; Phenyl-(CrC4)-alkyl, das im Phenylrest unsubstituiert oder durch einen oder mehrere Reste aus derAlkoxy, (CC 4 ) thioalkyl, CN, (C 2 -C 5 ) alkoxycarboπyl and (C 2 -C 6 ) alkenyl is substituted; or (C 3 -C 8 ) cycloalkyl which is unsubstituted or substituted by radicals from the group (C r C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C r C 4 ) alkylthio and halogen ; (C 5 -C 8 ) cycloalkenyl; Phenyl- (C r C 4 ) -alkyl, which is unsubstituted in the phenyl radical or by one or more radicals from the
Gruppe Halogen, (C1-C4)-Alkyl, (C^y-Alkoxy, (CrC4)-Haloalkyl, (C,-C4)- Thioalkyl, (C2-C5)-Alkoxycarbonyl, (C2-C5)-Alkylcarbonyloxy, Carbonamid, (C2-C5)-Alkylcarbonylamino, (C2-C5)-Alkylaminocarbonyl, Di-[(C1-C4)-aikyl]- carbonyl und Nitro substituiert ist; oder einen Rest der Formeln A-1 bis A- 10Halogen group, (C 1 -C 4 ) alkyl, (C 1 -C 4 alkoxy, (C r C 4 ) haloalkyl, (C, -C 4 ) thioalkyl, (C 2 -C 5 ) alkoxycarbonyl, ( C 2 -C 5 ) -alkylcarbonyloxy, carbonamide, (C 2 -C 5 ) -alkylcarbonylamino, (C 2 -C 5 ) -alkylaminocarbonyl, di - [(C 1 -C 4 ) -aikyl] - carbonyl and nitro or a radical of the formulas A-1 to A-10
A-4 A-5 A-6 A-7A-4 A-5 A-6 A-7
A-8 A-9 A-10A-8 A-9 A-10
worinwherein
X O, S, S(O) oder S02;XO, S, S (O) or S0 2 ;
R1 Wasserstoff oder (C C3)-Alkyl;R 1 is hydrogen or (CC 3 ) alkyl;
R2 Wasserstoff, Halogen, (C1-C3)-Alkyl oder (CrC3)-Alkoxy, wobei die beiden letztgenannten Reste unsubstituiert oder durch ein- oder mehrfach durch Halogen oder (C C3)-Alkoxy substituiert sind;R 2 is hydrogen, halogen, (C 1 -C 3 ) -alkyl or (C r C 3 ) -alkoxy, the latter two radicals being unsubstituted or substituted by one or more halogen or (CC 3 ) -alkoxy groups;
R3 Wasserstoff, Halogen, (CrC3)-Alkyl, (C1-C3)-Alkoxy oder (CrC3)-Alkylthio, wobei die vorgenannten alkylhaltigen Reste unsubstituiert oder ein- oder mehrfach durch Halogen oder ein- oder zweifach durch (C1-C3)-Alkoxy oder (C1-C3)-Alkylthio substituiert sind; oder einen Rest der Formel NR5R6, (C3- C6)-Cycloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C3-C4)-Alkenyloxy oder (C3- C4)-Alkinyloxy;R 3 is hydrogen, halogen, (C r C 3 ) -alkyl, (C 1 -C 3 ) -alkoxy or (C r C 3 ) -alkylthio, the abovementioned alkyl-containing radicals being unsubstituted or singly or multiply by halogen or mono- or are substituted twice by (C 1 -C 3 ) alkoxy or (C 1 -C 3 ) alkylthio; or a radical of the formula NR 5 R 6 , (C 3 -C 6 ) cycloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 4 ) alkenyloxy or (C 3 - C 4 ) alkynyloxy;
R4 Wasserstoff, (CrC4)-Alkyl oder (C1-C4)-Alkoxy undR 4 is hydrogen, (C r C 4 ) alkyl or (C 1 -C 4 ) alkoxy and
R5 und R6 unabhängig voneinander Wasserstoff, (C1-C4)-Alkyl, (C3-C4)-Alkenyl, (C1-C4)-Haloalkyl oder (C C4)-Alkoxy bedeuten;R 5 and R 6 are independently hydrogen, (C 1 -C 4 ) alkyl, (C 3 -C 4 ) alkenyl, (C 1 -C 4 ) haloalkyl or (CC 4 ) alkoxy;
A2) Verbindungen der allgemeinen Formel II und deren anorganische oder organische Salze,
R 2 -
A2) compounds of the general formula II and their inorganic or organic salts, R 2 -
N R R 5 NRR 5
worinwherein
R1 CO-Q-R8; R2 und R3 unabhängig voneinander H oder (CrC4)Alkyl; R4 H, (C1-C4)Alkyl, Hydroxy oder (CrC4) Alkoxy;R 1 CO-QR 8 ; R 2 and R 3 are independently H or (C r C 4 ) alkyl; R 4 H, (C 1 -C 4 ) alkyl, hydroxy or (C r C 4 ) alkoxy;
R5 (CrC4)Alkylsulfonyi, CHO, [(CrC4)Alkyl]-carbonyl, das unsubstituiert oder durch ein oder mehrere Halogenatome substituiert ist, [(C1-C4)Alkoxy]- oxalyl, [(C3-C6)Cycloalkyl]-carbonyl oder eine Gruppe der Formel W W WR 5 (C r C 4 ) alkylsulfonyi, CHO, [(C r C 4 ) alkyl] carbonyl which is unsubstituted or substituted by one or more halogen atoms, [(C 1 -C 4 ) alkoxy] oxalyl, [( C 3 -C 6 ) cycloalkyl] carbonyl or a group of the formula WWW
II II oder ||II II or ||
- C - T - R9 , -C - NR10R11 -C - N(R12)2 bedeuten, worin- C - T - R 9 , -C - NR 10 R 11 -C - N (R 12 ) 2 , in which
W ein Sauerstoff- oder Schwefelatom (O oder S);W is an oxygen or sulfur atom (O or S);
T O oder S;T O or S;
R9 H, (C1-C4)Alkyl, das unsubstituiert oder durch ein oder mehrere Halogenatome oder durch (C1-C4)Alkoxy, (^-C^Alkylthio, [(C1-C4)Alkoxy]-carbonyl und [(C1-C4)Alkyl]-carbonyl substituiert ist, R10 und R11 unabhängig voneinander H, (C1-C4)Alkyl, das unsubstituiert oder durch ein oder mehrere Halogenatome substituiert ist, oder (C3-C4)-Alkenyl oder (C3-C4)Alkinyl, wobei mindestens einer der Reste R10 und R 1 von Wasserstoff verschieden ist; die Reste R12 gemeinsam mit dem N-Atom einen heterocyclischen Ring mit 5 oder 6 Ringgliedern, der ein weiteres Heteroatom aus der Gruppe N, O und S in
den verschiedenen Oxidationsstufen enthalten kann und unsubstituiert oder durch (C C4)Alkyl oder die Oxogruppe substituiert ist, und Q O, S oder -NR13-; R6 H, (C C3)Alkyl, (C1-C3)Alkoxy, Halogen; R8 unabhängig voneinander (C1-C4)Alkyl, das unsubstituiert oder durch ein oder mehrere Halogenatome substituiert ist, oder (C3-C4)-Alkenyl oderR 9 H, (C 1 -C 4 ) alkyl which is unsubstituted or by one or more halogen atoms or by (C 1 -C 4 ) alkoxy, (^ -C ^ alkylthio, [(C 1 -C 4 ) alkoxy] - carbonyl and [(C 1 -C 4 ) alkyl] carbonyl is substituted, R 10 and R 11 independently of one another are H, (C 1 -C 4 ) alkyl which is unsubstituted or substituted by one or more halogen atoms, or (C 3 -C 4 ) alkenyl or (C 3 -C 4 ) alkynyl, where at least one of the radicals R 10 and R 1 is different from hydrogen; the radicals R 12 together with the N atom form a heterocyclic ring with 5 or 6 ring members, which is another heteroatom from the group N, O and S in can contain the various oxidation states and is unsubstituted or substituted by (CC 4 ) alkyl or the oxo group, and QO, S or -NR 13 -; R 6 H, (CC 3 ) alkyl, (C 1 -C 3 ) alkoxy, halogen; R 8 independently of one another (C 1 -C 4 ) alkyl which is unsubstituted or substituted by one or more halogen atoms, or (C 3 -C 4 ) alkenyl or
(C3-C4)-Alkinyl; A einen Rest der Formel(C 3 -C 4 ) alkynyl; A is a residue of the formula
bedeutet, worin Z CH oder N und einer der Reste X und Y Halogen, (CrC2)Alkyl, (CrC2)Alkoxy, OCF2H, CF3 oder OCH2CF3 und der andere der Reste X und Y (C1-C2)Alkyl,means in which Z is CH or N and one of the radicals X and Y is halogen, (C r C 2 ) alkyl, (C r C 2 ) alkoxy, OCF 2 H, CF 3 or OCH 2 CF 3 and the other of the radicals X and Y (C 1 -C 2 ) alkyl,
(C1-C2)Alkoxy oder (C C2)Haloalkoxy bedeuten; R7 H oder CH3 und R13 H, (C^C^Alkyl, das unsubstituiert oder durch ein oder mehrereAre (C 1 -C 2 ) alkoxy or (CC 2 ) haloalkoxy; R 7 H or CH 3 and R 13 H, (C ^ C ^ alkyl that is unsubstituted or substituted by one or more
Halogenatome substituiert ist, oder (C3-C4)-Alkenyl oder (C3-C4)Alkinyl bedeuten;
A3) Verbindungen der allgemeinen Formel III, deren N-Oxide und deren anorganische oder organische SalzeHalogen atoms is substituted, or (C 3 -C 4 ) alkenyl or (C 3 -C 4 ) alkynyl; A3) Compounds of the general formula III, their N-oxides and their inorganic or organic salts
worin Ri H, Halogen, (C1-C4)-Alkyl, das unsubstituiert oder ein- oder mehrfach durchwherein Ri H, halogen, (C 1 -C 4 ) alkyl, which is unsubstituted or one or more times by
Halogen substituiert ist, (CrC4)-Alkoxy, (C C4)-Alkylthio ;Halogen is substituted, (C r C 4 ) alkoxy, (CC 4 ) alkylthio;
R2 H oder Methyl;R 2 is H or methyl;
R3 Methyl oder Methoxy; A -N-(R4)R5;R 3 is methyl or methoxy; A -N- (R 4 ) R 5 ;
R4 H, (C1-Cβ)-Alkyl, das unsubstituiert oder ein- oder mehrfach durch Halogen,R 4 H, (C 1 -C β ) alkyl which is unsubstituted or one or more times by halogen,
(C C6-)-Alkoxy, (C3-C6)-Alkenyloxy, (C3-C6)-Alkinyloxy oder (C C6)-(CC 6 -) alkoxy, (C 3 -C 6 ) alkenyloxy, (C 3 -C 6 ) alkynyloxy or (CC 6 ) -
Alkylthio substituiert ist;Alkylthio is substituted;
H,
das unsubstituiert oder ein- oder mehrfach durch Halogen,H, which is unsubstituted or one or more times by halogen,
(CrCβ)-Alkoxy, (C3-Cβ)-Alkenyloxy, (C3-C6)-Alkinyloxy oder (CrC8)-Alklythio substituiert ist, oder C(O)R6; RR H,
oder (C3-C6)-Cycloalkyl, die unsubstituiert oder ein- oder mehrfach durch Halogen oder (CrC4)-Alkoxy substituiert sind, (C2-Cβ)-(C r C β ) alkoxy, (C 3 -C β ) alkenyloxy, (C 3 -C 6 ) alkynyloxy or (C r C 8 ) alklythio, or C (O) R 6 ; R R H, or (C 3 -C 6 ) cycloalkyl which are unsubstituted or substituted one or more times by halogen or (C r C 4 ) alkoxy, (C 2 -C β ) -
Alkenyl, das unsubstituiert oder ein- oder mehrfach durch Halogen substituiert ist, (C2-C6)-Alkinyl, Phenyl, Benzyl oder Naphthyl, die unsubstituiert oder ein- oder mehrfach durch Halogen, (C1-C4)-Alkyl,Alkenyl which is unsubstituted or mono- or polysubstituted by halogen, (C 2 -C 6 ) -alkynyl, phenyl, benzyl or naphthyl which is unsubstituted or mono- or polysubstituted by halogen, (C 1 -C 4 ) -alkyl,
(C1-C4)-Haloalkyl, (C C4)-Alkoxy, (C^C -Haloalkoxy, (C3-C6)-Alkenyloxy,(C 1 -C 4 ) haloalkyl, (CC 4 ) alkoxy, (C 1 -C 4 haloalkoxy, (C 3 -C 6 ) alkenyloxy,
(C3-Cβ)-Alkinyloxy, Nitro, Cyano, COOR8, NR^R,,, C(O)NR12R13, X RW,
S02NR16R17 oder durch X2R18 substituiert sind oder OR7; R7 (C1-C6)-Alkyl, das unsubstituiert oder durch (CrC4)-Alkoxy, (C3-C6)- Cycloalkyl, Cyano, COOR19, oder CONR26R27 substituiert ist, (CrC6)- Haloalkyl, (C3-C6)-Alkenyl, (C3-C6)-Haloalkenyl, (C3-C6)-Alkinyl, (C3-C6)- Haloalkinyl, Oxetan-3-yl, oder (C4-C6)-Cycloalkyl, das unsubstituiert oder teilweise durch Halogen, (CrC4)-Alkyl oder (C C4)-Alkoxy substituiert ist oder Phenyl, Benzyl oder Naphthyl, das unsubstituiert oder jeweils durch (CrC4)-Alkyl, (C1-C4)-Haloalkyl, (C C4)-Alkoxy, (C C4)-Haloalkoxy, (CrC4)- Alkylthio, (C1-C4)-Haloalkylthio, (C C4)-Alkylsulfonyl, (C C4)-Alkylsulfinyl, Nitro, Cyano, COOR^, NR20R21, CONR23R24 oder durch SO2NR25R9 substituiert ist; oder (C^C^-Alkyl, X^ oder X4R30; R8 H, (CrC6)-Alkyl, (C3-C6)-Alkenyl, (C3-C6)-Alkinyl oder Oxetan-3-yl;(C 3 -C β ) alkynyloxy, nitro, cyano, COOR 8 , NR ^ R ,,, C (O) NR 12 R 13 , XR W , S0 2 NR 16 R 17 or are substituted by X 2 R 18 or OR 7 ; R 7 (C 1 -C 6 ) alkyl which is unsubstituted or substituted by (C r C 4 ) alkoxy, (C 3 -C 6 ) cycloalkyl, cyano, COOR 19 , or CONR 26 R 27 , (C r C 6 ) haloalkyl, (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) haloalkenyl, (C 3 -C 6 ) alkynyl, (C 3 -C 6 ) haloalkynyl, oxetane-3 -yl, or (C 4 -C 6 ) cycloalkyl which is unsubstituted or partially substituted by halogen, (C r C 4 ) alkyl or (CC 4 ) alkoxy or phenyl, benzyl or naphthyl which is unsubstituted or in each case by (C r C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (CC 4 ) alkoxy, (CC 4 ) haloalkoxy, (C r C 4 ) alkylthio, (C 1 -C 4 ) - Haloalkylthio, (CC 4 ) alkylsulfonyl, (CC 4 ) alkylsulfinyl, nitro, cyano, COOR ^, NR 20 R 21 , CONR 23 R 24 or substituted by SO 2 NR 25 R 9 ; or (C ^ C ^ alkyl, X ^ or X 4 R 30 ; R 8 H, (C r C 6 ) alkyl, (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl or Oxetan-3-yl;
R9, Rio. Rn. R12. R13. Ri6. R17. 20- R2ι . R23. R2 . R25> R26 und R27 jeweils unabhängig voneinander H, (C C4)-Alkyl, (C3-C6)-Alkenyl oder (C3-C6)-Alkinyl; oderR 9 , Rio. Marg. R12. R 13.Ri6. R17. 20 - R 2 ι. R 23. R 2 . R 25 > R 26 and R 27 are each independently H, (CC 4 ) alkyl, (C 3 -C 6 ) alkenyl or (C 3 -C 6 ) alkynyl; or
R10 und R20 jeweils unabhängig voneinander die Gruppen -C(O)-X5-(C C4)-Alkyl oder -C(O)-(C C4)-Alkyl, die teilweise durch Halogen substituiert sein können; oder R10 und R^ oder R12 und R13 oder R16 und R17 oder R20 und R21 oder R23 und R24 oder R25 und R9 oder R26 und R27 gemeinsam eine (C4-C5)-Alkylen-Kette bilden, die teilweise durch Sauerstoff oder NR14 unterbrochen sein kann, worin R14 H, (C C4)-Alkyl, (C3-C6)-Alkenyl oder (C3-C6)-Alkinyl; R15 und R^ jeweils unabhängig voneinander (C^C -Alkyl oder (C1-C4)Haloalkyl; R18 und R30 jeweils unabhängig voneinander durch COOR28 substituiertes (C^C - Alkyl; R19. ^ und R28 jeweils unabhängig voneinander H oder (C1-C4)-Alkyl, X, und X3 jeweils unabhängig voneinander S, SO oder SO2; X2 und X4 jeweils unabhängig voneinander O oder S und X5 O oder NR14 bedeuten; A4) Amidosulfuron (21, S.37); A5) Ethoxysulfuron (287, S.488);
A6) Triasulfuron (723, S.1222);R 10 and R 20 each independently of one another are the groups -C (O) -X 5 - (CC 4 ) -alkyl or -C (O) - (CC 4 ) -alkyl, which can be partially substituted by halogen; or R 10 and R ^ or R 12 and R 13 or R 16 and R 17 or R 20 and R 21 or R 23 and R 24 or R 25 and R 9 or R 26 and R 27 together form a (C 4 -C 5 ) Form alkylene chain, which may be partially interrupted by oxygen or NR 14 , wherein R 14 is H, (CC 4 ) alkyl, (C 3 -C 6 ) alkenyl or (C 3 -C 6 ) alkynyl; R 15 and R ^ are each independently of one another (C ^ C -alkyl or (C 1 -C 4 ) haloalkyl; R 18 and R 30 are each independently substituted by COOR 28 (C ^ C-alkyl; R 19. ^ And R 28 each independently of one another H or (C 1 -C 4 ) alkyl, X, and X 3 each independently of one another S, SO or SO 2 ; X 2 and X 4 each independently of one another O or S and X 5 O or NR 14 ; A4) amidosulfuron (21, p.37); A5) ethoxysulfuron (287, p.488); A6) triasulfuron (723, p.1222);
A7) Metsulfuron (498, S.842);A7) Metsulfuron (498, p.842);
A8) Tribenuron (728, S.1230);A8) tribenuron (728, p.1230);
A9) Flupyrsulfuron (348, S.586); A10) Nicosulfuron (519, S.877);A9) flupyrsulfuron (348, p.586); A10) Nicosulfuron (519, p.877);
A11 ) Rimsulfuron (644, S.1095);A11) Rimsulfuron (644, p.1095);
A12) Primisulfuron (589, S.997);A12) Primisulfuron (589, p.997);
A13) Prosulfuron (613, S.1041);A13) prosulfuron (613, p.1041);
A14) Sulfosulfuron (668, S.1130); A15) Oxasulfuron (542, S.911 );A14) Sulfosulfuron (668, p.1130); A15) oxasulfuron (542, p.911);
A16) Ethametsulfuron (280, S.475);A16) ethametsulfuron (280, p.475);
A17) Imazosulfuron (416, S.703) undA17) Imazosulfuron (416, p.703) and
A18) Verbindungen der Formel V.wie in EP-A-0496701 offenbart:A18) Compounds of the formula V. as disclosed in EP-A-0496701:
Die suboptimale Toleranz der bislang verfügbaren Zuckerrübenmutanten gegenüber den genannten Sulfonylharnstoffen führt bei den Aufwandmengen, wie sie z.B. bei schwer bekämpfbaren Schadpflanzen (z.B. Anthemis arvensis) erforderlich sind, oftmals zu einer Schädigung der Kulturpflanzen, die mit einer Ertragsminderung und einem erheblichen wirtschaftlichen Ausfall verbunden ist.The suboptimal tolerance of the sugar beet mutants available to date to the sulfonylureas mentioned leads to the application rates such as in the case of harmful plants which are difficult to control (e.g. Anthemis arvensis), damage to the crop plants is often necessary, which is associated with a reduction in yield and a considerable economic failure.
Die Aufgabe der vorliegenden Erfindung besteht in der Überwindung dieser Nachteile. Die Aufgabe wird durch die vorliegende Erfindung gelöst, indem Zuckerrübenmutanten bereitstellt werden, die gegenüber einem oder mehreren Sulfonylharnstoffen der oben genannten (o.g.) allgemeinen Formeln I bis III, Amidosulfuron, Ethoxysulfuron Triasulfuron, Metsulfuron, Tribenuron, Flupyrsulfuron, Nicosulfuron, Rimsulfuron, Prosulfuron, Sulfosulfuron, Oxasulfuron, Etametsulfuron, Imazosulfuron und/oder Verbindungen der o.g.
Formel V eine sehr gute Verträglichkeit, d.h. eine hohe Toleranz aufweisen.The object of the present invention is to overcome these disadvantages. The object is achieved by the present invention by providing sugar beet mutants which, compared to one or more sulfonylureas of the abovementioned (above) general formulas I to III, amidosulfuron, ethoxysulfuron, triasulfuron, metsulfuron, tribenuron, flupyrsulfuron, nicosulfuron, rimsulfuron, sulfosulfuron, sulfosuron , Oxasulfuron, etametsulfuron, imazosulfuron and / or compounds of the above Formula V has a very good tolerance, ie a high tolerance.
Eine weitere Aufgabe der vorliegenden Erfindung besteht ebenfalls in der Verbesserung von Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs in den erfindungsgemäßen Zuckerrüben-Kulturen.Another object of the present invention is also to improve methods for controlling unwanted plant growth in the sugar beet crops according to the invention.
Überraschenderweise wurde gefunden, daß durch die Zugabe von Safenern zu Selektionsmedien, die herbizid wirksame Verbindungen enthalten, die Qualität und Quantität herbizidresistenter Zellen (Mutanten) verbessert wird, die aus den erfindungsgemäßen Selektionsverfahren resultieren. Die Zugabe von Safenern zu herbizidhaltigen Medien zum Auffinden von herbzidtoleranten Zellen (Mutanten) in vitro ist bisher nicht beschrieben worden.Surprisingly, it was found that the addition of safeners to selection media which contain herbicidally active compounds improves the quality and quantity of herbicide-resistant cells (mutants) which result from the selection processes according to the invention. The addition of safeners to herbicide-containing media to find herbicide-tolerant cells (mutants) in vitro has not previously been described.
Es wurden nun durch Selektion auf Sulfonylharnstoff-haltigen Nährmedien, insbesondere zusätzlich Safener enthaltenden Nährmedien Zuckerrübenmutanten gefunden, die überraschenderweise die gewünschte Resistenz gegenüber Sulfonylharnstoff-Herbiziden der allgemeinen Formeln I bis III, Amidosulfuron, Ethoxysulfuron Triasulfuron, Metsulfuron, Tribenuron, Flupyrsulfuron, Nicosulfuron, Rimsulfuron, Prosulfuron, Sulfosulfuron, Oxasulfuron, Etametsulfuron, Imazosulfuron und/oder Verbindungen der o.g. Formel V aufweisen.By selection on nutrient media containing sulfonylurea, in particular nutrient media additionally containing safeners, sugar beet mutants have now been found which surprisingly have the desired resistance to sulfonylurea herbicides of the general formulas I to III, amidosulfuron, ethoxysulfuron triasulfuron, metsulfuron, tribenulfuron, flupyrsulfuron, flup Prosulfuron, sulfosulfuron, oxasulfuron, etametsulfuron, imazosulfuron and / or compounds of the above Have formula V.
Außerdem weisen die erfindungsgemäßen Zuckerrübenmutanten weitere überraschende Vorteile auf, indem sie z.B. durch die besagten Sulfonylhamstoffe in ihrem Wachstum gefördert werden oder einen veränderten Gehalt anIn addition, the sugar beet mutants according to the invention have further surprising advantages, for example by are promoted by the said sulfonylureas in their growth or a changed content of
Kohlenhydraten oder Stickstoff-haltigen Verbindungen (z.B. Aminosäuregehalt, Proteinen) aufweisen.Carbohydrates or nitrogen-containing compounds (e.g. amino acid content, proteins).
Darüber hinaus weist die vorliegende Erfindung auch noch weitere Vorteile auf, denn sie ermöglicht die Bekämpfung eines breiteren Spektrums vonIn addition, the present invention also has other advantages because it enables a broader spectrum of
Schadpflanzen in den erfindungsgemäßen Zuckerrübenkulturen, so daß eine schnellere und sicherere Wirksamkeit gegenüber den Schadpflanzen und/oder
erheblich vereinfachte Kontrolle der Schadpflanzen ermöglicht wird, indem z.B. eine einzige oder nur wenige Applikationen erforderlich sind. Neben der Applikation im Vorauflauf ist insbesondere die Nachauflauf-Applikation bevorzugt, ganz besonders in dem Zeitraum zwischen Keimblatt- und 12-Blatt-Stadium der Schadpflanzen und/oder in dem Zeitraum zwischen Durchstoßen der Zuckerrüben und deren 12-Blatt-Stadium.Harmful plants in the sugar beet crops according to the invention, so that a faster and safer activity against the harmful plants and / or considerably simplified control of the harmful plants is made possible, for example by requiring a single or only a few applications. In addition to the pre-emergence application, the post-emergence application is particularly preferred, particularly in the period between the cotyledon and 12-leaf stage of the harmful plants and / or in the period between piercing the sugar beets and their 12-leaf stage.
Gegenstand der vorliegenden Erfindung sind daher Sulfonylhamstoff-toleranteThe present invention therefore relates to sulfonylurea tolerants
Zuckerrübenmutanten, deren Saat- oder Vermehrungsgut sowie deren Zellen, die gegenüber einem oder mehreren Sulfonylharnstoff ausgewählt aus der Gruppe A bestehend ausSugar beet mutants, their seeds or propagation material and their cells, selected from group A consisting of one or more sulfonylureas
A1) Verbindungen der o.g. allgemeinen Formel I,A1) Connections of the above general formula I,
A2) Verbindungen der o.g. allgemeinen Formel II,A2) Connections of the above general formula II,
A3) Verbindungen der o.g. allgemeinen Formel III, A4) Amidosulfuron (21 , S.37),A3) Connections of the above general formula III, A4) amidosulfuron (21, p.37),
A5) Ethoxysulfuron (287, S.488),A5) ethoxysulfuron (287, p.488),
A6) Triasulfuron (723, S.1222),A6) triasulfuron (723, p.1222),
A7) Metsulfuron (498, S.842),A7) Metsulfuron (498, p.842),
A8) Tribenuron (728, S.1230), A9) Flupyrsulfuron (348, S.586),A8) Tribenuron (728, p.1230), A9) Flupyrsulfuron (348, p.586),
A10) Nicosulfuron (519, S.877),A10) Nicosulfuron (519, p.877),
A11 ) Rimsulfuron (644, S.1095)A11) Rimsulfuron (644, p.1095)
A12) Primisulfuron (589, S.997)A12) Primisulfuron (589, p.997)
A13) Prosulfuron (613, S.1041) A14) Sulfosulfuron (668, S.1130)A13) prosulfuron (613, p.1041) A14) sulfosulfuron (668, p.1130)
A15) Oxasulfuron (542, S.911 );A15) oxasulfuron (542, p.911);
A16) Ethametsulfuron (280, S.475);A16) ethametsulfuron (280, p.475);
A17) Imazosulfuron (416, S.703) undA17) Imazosulfuron (416, p.703) and
A18) Verbindungen der Formel V.wie in EP-A-0496701 offenbart: Formel V:
A18) Compounds of the formula V. as disclosed in EP-A-0496701: Formula V:
tolerant sind und die vorzugsweise durch einen oder mehrere Sulfonylhamstoffe ausgewählt aus der Gruppe A bestehend aus A1 bis A18 in ihrem Wachstum gefördert werden.are tolerant and which are preferably promoted in their growth by one or more sulfonylureas selected from group A consisting of A1 to A18.
Es wird ausdrücklich darauf hingewiesen, daß die unter A4 bis A17 sowie B1 bis B9 (siehe unten) im einzelnen aufgeführten Herbizide im "The Pesticide Manual", 11th edition, The British Crop Protection Council, 1997, Bracknell, England, und der dort zitierten Literatur beschrieben sind. Die einzelnen Verbindungen sind in der Regel mit dem "common name" nach der International Organization for Standardization (ISO) bezeichnet; die in Klammern angegebenen Ziffern kennzeichnen die Nummer des Eintrags sowie die Seitenzahl.It is expressly pointed out that the herbicides listed under A4 to A17 and B1 to B9 (see below) in detail in "The Pesticide Manual", 11th edition, The British Crop Protection Council, 1997, Bracknell, England, and the cited therein Literature are described. The individual connections are usually designated with the "common name" according to the International Organization for Standardization (ISO); the numbers in brackets indicate the number of the entry and the page number.
Die erfindungsgemäßen Sulfonylhamstoff-toleranten Zuckerrübenmutanten, deren Saat- oder Vermehrungsgut sowie deren Zellen können z.B. durch herkömmliche Kreuzungsverfahren neben dem erfindungsgemäßen Merkmal der Sulfonylhamstoff-Resistenz auch eine weitere Herbizidresistenz (z.B. gegen Glufosinate oder Glyphosate) aufweisen oder eine weitere gentechnische Modifikation enthalten, z.B. durch Einführung einer Insekten-, Pilz- oder Virusresistenz (z.B. durch Expression eines Bt-Toxins, einer Chitinase, Glucanase) oder auch in ihren metabolischen Eigenschaften modifiziert sein, so daß eine qualitative und/oder quantitative Änderung von Inhaltsstoffen (z.B. des Energie- Kohlenhydrat-, Fettsäure- oder Stickstoffstoffwechsels bzw. mit denThe sulfonylurea-tolerant sugar beet mutants, their seeds or propagation material and their cells can e.g. through conventional crossing methods, in addition to the feature of the sulfonylurea resistance according to the invention, also have a further herbicide resistance (e.g. against glufosinates or glyphosates) or contain a further genetic modification, e.g. be modified by the introduction of insect, fungus or virus resistance (eg by expression of a Bt toxin, a chitinase, glucanase) or also in their metabolic properties, so that a qualitative and / or quantitative change in ingredients (eg the energy carbohydrate -, fatty acid or nitrogen metabolism or with the
Stoffwechselvorgängen in Zusammenhang stehenden Metabolitflüssen) resultiert.Metabolic processes in connection with metabolite flows) results.
Für den Fachmann bestehen verschiedene Möglichkeiten, Herbizid-tolerante pflanzliche Mutanten zu selektieren, wie z.B. in der US 5,162,602 oder US
,761 ,373 beschrieben.There are various possibilities for the person skilled in the art to select herbicide-tolerant plant mutants, such as, for example, in US Pat. No. 5,162,602 or US , 761, 373.
Darüber hinaus können pflanzliche Mutanten bzw. Zellinien können auch selektiert werden, indem z.B. Saatgut oder Zellkulturen (Kallus- oder Suspensionskulturen) in geeignetem Medium in Gegenwart steigender Herbizidkonzentrationen angezogen wird. Darüber hinaus kann bei diesem Selektionsverfahren der Zusatz eines geeigneten Mutagens (vgl. z.B. US 4,443,971) das Auftreten von Mutationen signifikant erhöhen.In addition, plant mutants or cell lines can also be selected by e.g. Seed or cell cultures (callus or suspension cultures) are grown in a suitable medium in the presence of increasing herbicide concentrations. In addition, the addition of a suitable mutagen (see e.g. US 4,443,971) can significantly increase the occurrence of mutations in this selection process.
Ein weiterer Gegenstand der vorliegenden Erfindung ist außerdem ein Verfahren zur Selektion von Herbizid-toleranten Zellen (Mutanten), vorzugsweise von eu- oder prokaryontischen Zellen, insbesondere solchen aus Pflanzen, Bakterien oder Hefen durch Kultivierung besagter Zellen in Gegenwart mindestens einer herbizid wirksamen Verbindungen und mindestens eines Safeners unter geeigneten Bedingungen. Das erfindungsgemäße Verfahren zur Selektion herbizid-toleranter Mutanten führt zu einer verbesserten Qualität und/oder Quantität der herbizid- resistenten Zellen, insbesondere bei der Selektion in Gegenwart von Herbizidkonzentrationenen, die zu > 50%, vorzugsweise zu >90%, besonders bevorzugt zu > 95% und ganz besonders bevorzugt zu >99 % für die jeweilige Zellpopulation letal sind.Another object of the present invention is also a method for the selection of herbicide-tolerant cells (mutants), preferably of eu or prokaryotic cells, in particular those from plants, bacteria or yeasts, by cultivating said cells in the presence of at least one herbicidally active compound and at least a safener under suitable conditions. The method according to the invention for the selection of herbicide-tolerant mutants leads to an improved quality and / or quantity of the herbicide-resistant cells, in particular when selecting in the presence of herbicide concentrations which are> 50%, preferably> 90%, particularly preferably> 95 % and very particularly preferably> 99% are lethal for the respective cell population.
Überraschenderweise wurde eine Steigerung der Quantität und/oder eine Verbesserung der Qualität der selektierten Mutanten nicht nur in Gegenwart von Herbizid-Safener-Mischungen beobachtet, deren agronomische Verwendung an der Kulturpflanze bekannt ist, sondern auch in Gegenwart von Herbizid-Safener- Mischungen deren agronomische Verwendung für die entsprechende Kulturpflanze bisher völlig unbekannt ist.Surprisingly, an increase in the quantity and / or an improvement in the quality of the selected mutants was observed not only in the presence of herbicide-safener mixtures whose agronomic use on the crop is known, but also in the presence of herbicide-safener mixtures whose agronomic use is completely unknown for the corresponding crop.
Besonders gut geeignete Verfahren zur qualitativen und/oder quantitativen Verbesserung der Mutantenausbeute besteht z.B. darin, Zellen, vorzugsweise Zellsuspensionen in Gegenwart von einem oder mehreren Herbizid und einem oder mehreren Safener in einem Konzentrationsbereich von 10"3 M bis 10'7 M,
vorzugsweise im Bereich von 10"4 M bis 10"6 M zu behandeln und nach einem Zeitraum von etwa einem Tag bis 2 Wochen, vorzugsweise etwa 3-10 Tagen, z.B. einer Woche die Zellen mit frischem Zellkulturmedium ohne Herbizid, aber mit Safener zu versetzen und diesen Subkulturschritt über etwa 3 - 5 Zyklen fortzusetzen. Danach werden die Zellsuspensionen z.B. auf Agarmedien mit dem jeweiligen herbiziden Wirkstoff (im Konzentrationsbereich von 10"3 M bis 10"7 M, vorzugsweise 10"4 M bis 10"6 M) mit und ohne Safener (im Konzentrationsbereich 10"3 M bis 10'7 M, vorzugsweise 10"4 M bis 10"6 M) ausplattiert. Das Konzentrationsverhältnis von Safener zu herbizidem Wirkstoff in der Mixtur kann dabei im Verhältnis von 100:1 bis 1 :100 differieren, vorzugsweise im Bereich 10:1 bis 1 :10. Etwa 2 - 8 Wochen nach dem Ausplattieren der Zellsuspension, vorzugsweise etwa 3 - 6 Wochen nach dem Ausplattieren, lassen sich die herbizidresistenten Zeilklone auf frisches Selektionsmedium überführen. Dabei kann entweder die Herbizidkonzentration beibehalten werden oder um den Faktor 2 - 100, vorzugsweise um den Faktor 2 - 10 erhöht werden. Zellmutanten mit einer gegenüber den Wildtypzellen signifikant erhöhten Herbizidresistenz werden für die sich anschließende Pflanzenregeneration verwendet. Dazu werden die Mutanten auf/in Kulturmedien subkultiviert, die den für den jeweiligen Genotyp notwendigen Gehalt an Cytokininen und/oder Auxinen aufweisen. Die Pflanzenregeneration kann dabei in An- oder Abwesenheit von Herbizid oder gegebenenfalls Herbizid-Safener-Mixtur durchgeführt werden.A particularly suitable method for qualitatively and / or quantitatively improving the mutant yield consists, for example, of cells, preferably cell suspensions, in the presence of one or more herbicides and one or more safeners in a concentration range from 10 "3 M to 10 '7 M, preferably in the range of 10 "4 M to 10 " 6 M to treat and after a period of about a day to 2 weeks, preferably about 3-10 days, for example a week, the cells with fresh cell culture medium without herbicide, but with safener and continue this subculture step for about 3-5 cycles. The cell suspensions are then applied, for example, to agar media with the respective herbicidal active ingredient (in the concentration range from 10 "3 M to 10" 7 M, preferably 10 "4 M to 10 " 6 M) with and without safener (in the concentration range 10 "3 M to 10 7 M, preferably 10 "4 M to 10 " 6 M. The concentration ratio of safener to herbicidal active ingredient in the mixture can differ in a ratio of 100: 1 to 1: 100, preferably in the range 10: 1 to 1: 10. About 2-8 weeks after plating the cell suspension, preferably about 3-6 weeks after plating, the herbicide-resistant cell clones can be transferred to fresh selection medium, either maintaining the herbicide concentration or by a factor of 2-100, preferably around by a factor of 2 to 10. Cell mutants with a herbicide resistance that is significantly higher than that of wild-type cells are used for the subsequent plant regeneration utanten subcultivated on / in culture media which have the content of cytokinins and / or auxins necessary for the respective genotype. Plant regeneration can be carried out in the presence or absence of a herbicide or, if appropriate, a herbicide / safener mixture.
Im Sinne der vorliegenden Erfindung bedeutet "Safener" eine Verbindung, mittels derer der durch ein Herbizid möglicherweise verursachte Schaden an einer Kulturpflanze reduziert oder vermieden werden kann. Beispiele für geeignete Safener sind solche, die in Kombination mit Sulfonylhamstoff-Herbiziden, vorzugsweise, Phenylsulfonylhamstoffen Safenerwirkung entfalten. Geeignete Safener sind aus WO-A-96/14747 und der dort zitierten Literatur bekannt. Folgende Gruppen von Verbindungen sind beispielsweise als Safener für die oben erwähnten herbiziden Wirkstoffe (A) geeignet: a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure, vorzugsweise Verbindungen wie
1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3- carbonsäureethylester, und verwandte Verbindungen, wie sie in der WO 91/07874 beschrieben sind, b) Derivate der Dichlorphenylpyrazolcarbonsäure, vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-methyl-pyrazol-3-carbonsäureethylester,For the purposes of the present invention, “safener” means a compound by means of which the damage to a crop plant possibly caused by a herbicide can be reduced or avoided. Examples of suitable safeners are those which, in combination with sulfonylurea herbicides, preferably phenylsulfonylureas, have a safener action. Suitable safeners are known from WO-A-96/14747 and the literature cited therein. The following groups of compounds are suitable, for example, as safeners for the herbicidal active compounds (A) mentioned above: a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type, preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester, and related compounds as described in WO 91/07874, b) derivatives of dichlorophenylpyrazole carboxylic acid, preferably Compounds such as ethyl 1 - (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate,
1-(2,4-Dichlorphenyl)-5-isopropyl-pyrazol-3-carbonsäureethylester, 1-(2,4-Dichlorphenyl)-5-(1 ,1-dimethyl-ethyl)pyrazol-3-carbonsäureethyl-ester (S1-4), 1-(2,4-Dichlorphenyl)-5-phenyl-pyrazol-3-carbonsäureethylester (S1-5) und verwandte Verbindungen, wie sie in EP-A-333 131 und EP-A-269 806 beschrieben sind. c) Verbindungen vom Typ der Triazolcarbonsäuren, vorzugsweise Verbindungen wie Fenchlorazol, d.h.1- (2,4-dichlorophenyl) -5-isopropyl-pyrazole-3-carboxylic acid ethyl ester, 1- (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (S1 -4), 1- (2,4-dichlorophenyl) -5-phenyl-pyrazole-3-carboxylic acid ethyl ester (S1-5) and related compounds as described in EP-A-333 131 and EP-A-269 806 . c) Compounds of the triazole carboxylic acid type, preferably compounds such as fenchlorazole, i.e.
1 -(2,4-Dichlorphenyl)-5-trichlormethyl-(1 H)-1 ,2,4-triazol-3- carbonsäureethylester, und verwandte Verbindungen (siehe EP-A-174 562 und EP-A-346 620); d) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure, oder der 5,5-Diphenyl-2-isoxazolin-3-carbonsäure vorzugsweise Verbindungen wie 5-(2,4-Dichlorbenzyl)-2-isoxazolin-3- carbonsäureethylester oder 5-Phenyl-2-isoxazolin-3-carbonsäureethylester und verwandte Verbindungen, wie sie in WO 91/08202 beschrieben sind, bzw. der 5,5-Diphenyl-2-isoxazolin-carbonsäureethylester oder -n- propylester oder der 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3- carbonsäureethylester, wie sie in WO-A-95/07897 beschrieben sind. e) Verbindungen vom Typ der 8-Chinolinoxyessigsäure, vorzugsweise (5-Chlor-8-chinolinoxy)-essigsäure-(1 -methyl-hex-1 -yl)-ester,1 - (2,4-dichlorophenyl) -5-trichloromethyl- (1 H) -1, 2,4-triazole-3-carboxylic acid ethyl ester, and related compounds (see EP-A-174 562 and EP-A-346 620) ; d) Compounds of the 5-benzyl or 5-phenyl-2-isoxazoline-3-carboxylic acid type, or the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds such as 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester and related compounds, as described in WO 91/08202, or the 5,5-diphenyl-2-isoxazoline-carboxylic acid ethyl ester or - n-propyl ester or the 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester, as described in WO-A-95/07897. e) compounds of the 8-quinolineoxyacetic acid type, preferably (5-chloro-8-quinolinoxy) acetic acid (1-methyl-hex-1-yl) ester,
(5-Chlor-8-chinolinoxy)-essigsäure-(1 ,3-dimethyl-but-1-yl)-ester, (5-Chlor-8-chinolinoxy)-essigsäure-4-allyl-oxy-butylester, (5-Chlor-8-chinolinoxy)-essigsäure-1-allyloxy-prop-2-ylester, (5-Chlor-8-chinolinoxy)-essigsäureethylester, (5-Chlor-8-chinolinoxy)-essigsäuremethylester,(5-chloro-8-quinolinoxy) -acetic acid- (1,3-dimethyl-but-1-yl) ester, (5-chloro-8-quinolinoxy) -acetic acid-4-allyl-oxy-butyl ester, (5th -Chloro-8-quinolinoxy) -acetic acid-1-allyloxy-prop-2-yl ester, (5-chloro-8-quinolinoxy) -acetic acid ethyl ester, (5-chloro-8-quinolinoxy) -acetic acid methyl ester,
(5-Chlor-8-chinolinoxy)-essigsäureallylester, (5-Chlor-8-chinolinoxy)-essigsäure-2-(2-propyliden-iminoxy)-1-
ethylester,(5-chloro-8-quinolinoxy) -acetic acid allyl ester, (5-chloro-8-quinolinoxy) -acetic acid-2- (2-propylidene-iminoxy) -1- ethyl ester,
(5-Chlor-8-chinolinoxy)-essigsäure-2-oxo-prop-1-ylester und verwandte Verbindungen, wie sie in EP-A-86 750, EP-A-94 349 und EP-A-191 736 oder EP-A-0 492 366 beschrieben sind. f) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)-malonsäure, vorzugsweise Verbindungen wie (5-Chlor-8-chinolinoxy)-malonsäure- diethylester, (5-Chlor-8-chinolinoxy)-malonsäurediallylester, (5-Chlor-8-chinolinoxy)-malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind. g) Wirkstoffe vom Typ der Phenoxyessig- bzw. -propionsäurederivate bzw. der aromatischen Carbonsäuren, wie z.B. 2,4-Dichlorphenoxyessigsäure(ester) (2,4-D), 4-Chlor-2-methyl-phenoxy-propionester (Mecoprop), MCPA oder 3,6-Dichlor-2-methoxy-benzoesäure(ester) (Dicamba).(5-Chloro-8-quinolinoxy) -acetic acid-2-oxo-prop-1-yl ester 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. f) Compounds of the type of (5-chloro-8-quinolinoxy) malonic acid, preferably compounds such as (5-chloro-8-quinolinoxy) malonic acid diethyl ester, (5-chloro-8-quinolinoxy) malonic acid diallyl ester, (5- Chloro-8-quinolinoxy) -malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198. g) active substances of the phenoxyacetic or propionic acid derivative or aromatic carboxylic acid type, e.g. 2,4-dichlorophenoxyacetic acid (ester) (2,4-D), 4-chloro-2-methylphenoxy-propionester (mecoprop), MCPA or 3,6-dichloro-2-methoxy-benzoic acid (ester) (dicamba) .
Insbesondere ist ein Gegenstand der vorliegenden Erfindung ein Verfahren zur Herstellung von Sulfonylhamstoff-toleranten Pflanzen durch Kultivierung auf/in einem Sulfonylharnstoff-haltigen Nährmedium in Gegenwart eines geeigneten Safeners, indem a) Kallus- oder Zellsuspensionskulturen unter Beibehaltung ihrer embryogenen und morphogenen Kompetenz selektioniert, b) die unter a) erhaltenen Kulturen auf/in einem Sulfonylharnstoff-haltigen Nährmedium kultiviert und selektioniert und c) aus den unter b) erhaltenen Kulturen intakte Pflanzen regeneriert werden.In particular, an object of the present invention is a method for producing sulfonylurea-tolerant plants by cultivation on / in a sulfonylurea-containing nutrient medium in the presence of a suitable safener, by a) selecting callus or cell suspension cultures while maintaining their embryogenic and morphogenic competence, b) the cultures obtained under a) are cultivated and selected on / in a sulfonylurea-containing nutrient medium and c) intact plants are regenerated from the cultures obtained under b).
Insbesondere ist ein weiterer Gegenstand der voriiegenden Erfindung einIn particular, another object of the present invention is a
Verfahren zur Herstellung der erfindungsgemäßen Zuckerrübenmutanten durch Kultivierung auf/in einem Sulfonylharnstoff-haltigen Nährmedium, vorzugsweise in Gegenwart eines geeigneten Safeners, indem a) Kallus- oder Zellsuspensionskulturen unter Beibehaltung ihrer embryogenen und morphogenen Kompetenz selektioniert, b) die unter a) erhaltenen Kulturen auf/in einem Sulfonylharnstoff-haltigen Nährmedium kultiviert und selektioniert und
c) aus den unter b) erhaltenen Kulturen intakte Pflanzen regeneriert werden.Process for producing the sugar beet mutants according to the invention by culturing on / in a sulfonylurea-containing nutrient medium, preferably in the presence of a suitable safener, by a) selecting callus or cell suspension cultures while maintaining their embryogenic and morphogenic competence, b) the cultures obtained under a) on / cultivated and selected in a nutrient medium containing sulfonylurea and c) intact plants are regenerated from the cultures obtained under b).
Außerdem ist ein Erfindungsgegenstand die Verwendung von erfindungsgemäßen Zuckerrübenmutanten, die nach dem erfindungsgemäßen Verfahren erhältlich sind in der Landwirtschaft, z.B. als Futtermittel oder für die Lebensmittelindustrie, insbesondere zur Zuckergewinnung.In addition, an object of the invention is the use of sugar beet mutants according to the invention which can be obtained by the process according to the invention in agriculture, e.g. as animal feed or for the food industry, especially for sugar production.
Noch ein weiterer Gegenstand der vorliegenden Erfindung ist auch ein Verfahren zur Kontrolle von unerwünschtem Pfianzenwuchs in Kulturen der erfindungsgemäßen Zuckerrübenmutanten, dadurch gekennzeichnet, daß auf die Pflanzen, deren Saat- oder Vermehrungsgut oder deren Anbaufläche ein oder mehrere Sulfonylhamstoffe ausgewählt aus der Gruppe A bestehend aus A1 bis A18, gegebenenfalls in Kombination mit einem oder mehreren Herbiziden ausgewählt aus der Gruppe B bestehend aus B1) Herbiziden aus der Klasse der Imidazolinone, vorzugsweise Imazethapyr (415, S.701 ), lmazamethapyr (2, S.5, AC 263,222), lmazapyr (413, S.697), Imazaquin (414, S.699), Imazamox (412, S.696); B2) Herbiziden aus der Klasse der Inhibitoren des photosynthetischen Elektronentransports, vorzugsweise der Biscarbamate, besonders bevorzugt Phenmedipham (563, S.948), Desmedipham (206, S.349);Yet another object of the present invention is also a method for controlling undesirable plant growth in crops of the sugar beet mutants according to the invention, characterized in that one or more sulfonylureas selected from group A consisting of A1 are added to the plants, their seeds or propagation material or their cultivated area to A18, optionally in combination with one or more herbicides selected from group B consisting of B1) herbicides from the class of the imidazolinones, preferably imazethapyr (415, p. 701), imazamethapyr (2, p. 5, AC 263.222), imazapyr (413, p.697), imazaquin (414, p.699), imazamox (412, p.696); B2) herbicides from the class of inhibitors of photosynthetic electron transport, preferably biscarbamates, particularly preferably phenmedipham (563, p.948), desmedipham (206, p.349);
B3) einem Herbizid aus der Klasse der PPO-Hemmer, z.B. der Diphenylether oder der Azole, vorzugsweise Azifluorfen (7, S.12), Oxyfluorfen (547, S.919), Pyraflufen (617, S.1048), Carfentrazone (112, S.191 ), Lactofen (442, S.747), Nitrofen (S1193, S.1343), Oxadiargyl (538, S.904), Fluoroglycofen (344, S.580), Sulfentrazone (665, S.1126) oder auch ein CF3-Uracil der Formel IV wie in US Patent 5,183,492 offenbart:
Formel IV:B3) a herbicide from the class of the PPO inhibitors, for example the diphenyl ether or the azoles, preferably Azifluorfen (7, S.12), Oxyfluorfen (547, S.919), Pyraflufen (617, S.1048), Carfentrazone (112 , P.191), lactofen (442, p.747), nitrofen (S1193, p.1343), oxadiargyl (538, p.904), fluoroglycofen (344, p.580), sulfentrazone (665, p.1126) or also a CF 3 uracil of the formula IV as disclosed in US Pat. No. 5,183,492: Formula IV:
B4) einem Herbizid aus der Klasse der Hydroxyphenylpyruvat-Dioxygenase (HPPDO)-Inhibitoren, z.B. der Triketone, vorzugsweise Isoxaflutole (436, S.737), Isoxachlortole (RPA-201735) oder Sulcotrione (664, S.1124); B5) einem Herbizid aus der Klasse der herbizid wirksamen, gegebenenfalls synthetischen Auxine oder deren Transporthemmer, vorzugsweise Quinmerac (636, S.1080), Clopyralid (153, S.260), Diflufenzopyr (50, S.81 , BAS 65400H); B6) einem Herbizid aus der Klasse der Lipid- oder der Fettsäure-Synthese- Inhibitoren, vorzugsweise der Aryloxyphenoxycarbonsäuren oder der Cyclohexandionoxime, besonders bevorzugt Fenoxaprop (309, S.519), Haloxyfop (390, S.659), Fluazifop (327-328, S.553-557), Quizalofop (640-641 , S.1087- 1092), Clodinafop (147, S.251 ), Propaquizafop (602, S.1021 ), Clethodim (146, S.250), Sethoxidim (648, S.1101 ), Tepraloxydim (49, S.80, BAS 620H, Caloxydim), Butroxidim (98, S.167) und Cycloxidim (174, S.290) oder Prosulfocarb (612, S.1040); B7) einem Herbizid aus der Klasse der Glutamin-Synthetase-Inhibitoren, vorzugsweise Phosphinoaminosäure-Derivate, besonders bevorzugt glufosinate (382, S.643);B4) a herbicide from the class of the hydroxyphenyl pyruvate dioxygenase (HPPDO) inhibitors, e.g. the triketones, preferably isoxaflutole (436, p.737), isoxachlortole (RPA-201735) or sulcotrione (664, p.1124); B5) a herbicide from the class of herbicidally active, optionally synthetic auxins or their transport inhibitors, preferably Quinmerac (636, S.1080), clopyralide (153, S.260), diflufenzopyr (50, S.81, BAS 65400H); B6) a herbicide from the class of lipid or fatty acid synthesis inhibitors, preferably aryloxyphenoxycarboxylic acids or cyclohexanedione oximes, particularly preferably fenoxaprop (309, p.519), haloxyfop (390, p.659), fluazifop (327-328 , P.553-557), quizalofop (640-641, p.1087-1092), clodinafop (147, p.251), propaquizafop (602, p.1021), clethodim (146, p.250), sethoxidim ( 648, p.1101), tepraloxydim (49, p.80, BAS 620H, caloxydim), butroxidim (98, p.167) and cycloxidim (174, p.290) or prosulfocarb (612, p.1040); B7) a herbicide from the class of glutamine synthetase inhibitors, preferably phosphinoamino acid derivatives, particularly preferably glufosinate (382, p.643);
B8) einem Herbizid aus der Klasse der 5-Enolpyruvylshikimat-3-phosphat- Synthase-Inhibitoren, vorzugsweise glyphosate (383, S.646); B9) einem Herbizid aus der Klasse der Benzofuranylalkansulfonate, vorzugsweise Ethofumesate (285, S.484) oder diese Wirkstoffe der Gruppe A oder B enthaltende herbizide Mittel zeitgleich oder aufeinanderfolgend appliziert werden.
Und schließlich ist ein Erfindungsgegenstand auch die Verwendung von einem oder mehreren Sulfonylharnstoffen ausgewählt aus der Gruppe A (A1 bis A18) wie definiert, ggf. in Kombination mit einem oder mehreren Herbiziden ausgewählt aus der Gruppe B, bestehend aus B1 bis B9, oder diese enthaltende herbizide Mittel auf Anbauflächen von erfindungsgemäßen Zuckerrübenkulturen.B8) a herbicide from the class of 5-enolpyruvylshikimate-3-phosphate synthase inhibitors, preferably glyphosate (383, p. 646); B9) a herbicide from the class of benzofuranylalkanesulfonates, preferably ethofumesate (285, p.484) or herbicidal compositions containing these active ingredients from group A or B can be applied simultaneously or in succession. Finally, an object of the invention is also the use of one or more sulfonylureas selected from group A (A1 to A18) as defined, optionally in combination with one or more herbicides selected from group B, consisting of B1 to B9, or containing them Herbicidal agents on the areas under cultivation of sugar beet crops according to the invention.
Sofern es sich um chirale Verbindungen handelt, werden von den unter A1 bis A18 sowie unter B1 bis B9 genannten Wirkstoffen sowohl deren racemische Gemische als auch deren aktive Enantiomere umfaßt. Außerdem sind auch die Salze der unter A1 bis A18 sowie unter B1 bis B9 genannten Wirkstoffe mit organischen oder anorganischen Säuren oder Basen umfaßt, sofern es sich um Salzbildner handelt. Ebenso sind auch ggf. die Ester der unter A1 bis A18 sowie unter B1 bis B9 genannten Wirkstoffe umfaßt, sofern diese herbizid wirksam sind.If the compounds are chiral, the active substances mentioned under A1 to A18 and under B1 to B9 include both their racemic mixtures and their active enantiomers. In addition, the salts of the active ingredients mentioned under A1 to A18 and under B1 to B9 with organic or inorganic acids or bases are included, provided that they are salt formers. Likewise, the esters of the active ingredients mentioned under A1 to A18 and under B1 to B9 are also included, if they are herbicidally active.
Die erfindungsgemäßen Verfahren zur Kontrolle von Schadpflanzen in den erfindungsgemäßen Zuckerrübenkulturen mit den Sulfonylharnstoffen der Gruppe A (A1 bis A18) eröffnen eine ökonomisch und ökologisch vorteilhafte Kontrolle von Schadpflanzen. Die Vorteile liegen z.B. in einem positiven wachstumsregulatorischen Effekt, einer verminderten Anzahl von Applikationen bzw. einer Reduzierung der Aufwandmengen (im Vergleich zur konventionellen Anwendung herbizider Mittel), einer in der Regel guten biologischen Bodenabbaubarkeit, einer geringen Belastung im Nachanbau und/oder einer guten Nützlingsschonung.The methods according to the invention for controlling harmful plants in the sugar beet crops according to the invention with the sulfonylureas of group A (A1 to A18) open up an economically and ecologically advantageous control of harmful plants. The advantages are e.g. in a positive growth regulatory effect, a reduced number of applications or a reduction in the application rates (compared to the conventional use of herbicides), a generally good biodegradability, a low burden in post-cultivation and / or good protection of beneficial organisms.
Insbesondere die Kombinationsmöglichkeiten von herbiziden Wirkstoffen der Gruppe A (d.h. Sulfonylhamstoffe A1 bis A18) mit Herbiziden der Gruppe B (d.h. Herbizide B1 bis B9) erweisen sich in den erfindungsgemäßen Verfahren zur Kontrolle von Schadpflanzen als besonders vorteilhaft.In particular, the possible combinations of herbicidal active ingredients from group A (i.e. sulfonylureas A1 to A18) with herbicides from group B (i.e. herbicides B1 to B9) have proven particularly advantageous in the processes according to the invention for controlling harmful plants.
Unter dem Begriff „Herbizid-tolerant" ist im Sinne der vorliegenden Anmeldung zu verstehen, daß die Herbizid-toleranten Zuckerrübenmutanten in Gegenwart eines
oder mehrerer Sulfonylhamstoffe der Gruppe A, ggf. in Kombination mit einem oder mehreren Herbiziden der Gruppe B keine apparente Beeinträchtigung ihrer physiologischen Funktionen zeigen, wobei dieselben Sulfonylhamstoffe bei nichttoleranten Pflanzen, eine das Wachstum beeinträchtigende oder phytotoxische Wirkung zeigen. Art und Ausmaß der Herbizidtoleranz hängen dabei vom jeweiligen Herbizid, der jeweiligen Dosierung und allgemeinen Wachstumsbedingungen ab.In the context of the present application, the term “herbicide-tolerant” means that the herbicide-tolerant sugar beet mutants are present in the presence of a or several sulfonylureas of group A, possibly in combination with one or more herbicides of group B, do not show any apparent impairment of their physiological functions, the same sulfonylureas showing non-tolerant plants, a growth-impairing or phytotoxic effect. The type and extent of herbicide tolerance depend on the particular herbicide, the respective dosage and general growth conditions.
Besonders bevorzugt besitzen die erfindungsgemäßen Zuckerrübenmutanten, deren Saat- oder Vermehrungsgut oder deren Zellen eine Toleranz gegenüber Verbindungen der allgemeinen Formel I in einem Konzentrationsbereich von 0,5- 40, insbesondere 1-20 und ganz besonders 3-10 g a.i./ha, gegenüber Verbindungen der allgemeinen Formel II in einem Konzentrationsbereich von 1- 40, insbesondere 2-20 und ganz besonders 6-10 g a.i./ha, gegenüber Verbindungen der allgemeinen Formel III in einem Konzentrationsbereich von 0,5- 50, insbesondere 1-25 und ganz besonders 3-12,5 g a.i./ha, gegenüber Amidosulfuron in einem Konzentrationsbereich von 1-60, insbesondere 2-30 und ganz besonders 6-15 g a.i./ha, gegenüber Ethoxysulfuron in einem Konzentrationsbereich von 5-120, insbesondere 10-60 und ganz besonders 20-30 g a.i./ha, gegenüber Triasulfuron in einem Konzentrationsbereich von 1-80, insbesondere 2-40 und ganz besonders 6-20 g a.i./ha, gegenüber Metsulfuron in einem Konzentrationsbereich von 0,1-50, insbesondere 1-25 und ganz besonders 3-12,5 g a.i./ha, gegenüber Tribenuron in einem Konzentrationsbereich von 3- 100, insbesondere 6-50 und ganz besonders 10-25 g a.i./ha, gegenüber Flupyrsulfuron in einem Konzentrationsbereich von 1-80, insbesondere 2-40 und ganz besonders 6-20 g a.i./ha, gegenüber Nicosulfuron in einem Konzentrationsbereich von 1-120, insbesondere 2-60 und ganz besonders 6-30 g a.i./ha, gegenüber Rimsulfuron in einem Konzentrationsbereich von 0,1-60, insbesondere 0,2-30 und ganz besonders 0,6-15 g a.i./ha, gegenüber Primisulfuron in einem Konzentrationsbereich von 1-100, insbesondere 2-50 und ganz besonders 6-25 g a.i./ha, gegenüber Prosulfuron in einem Konzentrationsbereich von 1-90, insbesondere 2-45 und ganz besonders 6-25 g
a.i./ha, gegenüber Sulfosulfuron in einem Konzentrationsbereich von 1-90, insbesondere 2-45 und ganz besonders 6-25 g a.i./ha, gegenüber Oxasulfuron in einem Konzentrationsbereich von 5-250, insbesondere 10-125 und ganz besonders 30-65 g a.i./ha, gegenüber Etametsulfuron in einem Konzentrationsbereich von 0,1-50, insbesondere 0,2-25 und ganz besonders 0,6- 12,5 g a.i./ha, gegenüber Imazosulfuron in einem Konzentrationsbereich von 10- 250, insbesondere 20-125 und ganz besonders 30-65 g a.i./ha, bzw. gegenüber Verbindungen der Formel V in einem Konzentrationsbereich von 0,5-120, insbesondere 1-60 und ganz besonders 3-30 g a.i./ha.The sugar beet mutants, their seeds or propagation material or their cells particularly preferably have a tolerance to compounds of the general formula I in a concentration range of 0.5-40, in particular 1-20 and very particularly 3-10 g ai / ha, to compounds of the general formula II in a concentration range of 1-40, in particular 2-20 and very particularly 6-10 g ai / ha, compared to compounds of the general formula III in a concentration range of 0.5-50, in particular 1-25 and very particularly 3-12.5 g ai / ha, compared to amidosulfuron in a concentration range of 1-60, in particular 2-30 and very particularly 6-15 g ai / ha, compared to ethoxysulfuron in a concentration range of 5-120, especially 10-60 and very particularly 20-30 g ai / ha, compared to triasulfuron in a concentration range of 1-80, in particular 2-40 and very particularly 6-20 g ai / ha, compared to metsulfuron in a concentration range of 0.1-50, in particular other 1-25 and very particularly 3-12.5 g ai / ha, compared to tribenuron in a concentration range of 3-100, in particular 6-50 and very particularly 10-25 g ai / ha, compared to flupyrsulfuron in a concentration range of 1- 80, in particular 2-40 and very particularly 6-20 g ai / ha, compared to nicosulfuron in a concentration range of 1-120, in particular 2-60 and very particularly 6-30 g ai / ha, compared to rimsulfuron in a concentration range of 0, 1-60, in particular 0.2-30 and very particularly 0.6-15 g ai / ha, compared to primisulfuron in a concentration range of 1-100, in particular 2-50 and very particularly 6-25 g ai / ha, compared to prosulfuron in a concentration range of 1-90, especially 2-45 and very particularly 6-25 g ai / ha, compared to sulfosulfuron in a concentration range of 1-90, in particular 2-45 and very particularly 6-25 g ai / ha, compared to oxasulfuron in a concentration range of 5-250, especially 10-125 and very particularly 30-65 g ai / ha, compared to etametsulfuron in a concentration range of 0.1-50, in particular 0.2-25 and very particularly 0.6-12.5 g ai / ha, compared to imazosulfuron in a concentration range of 10- 250, especially 20- 125 and very particularly 30-65 g ai / ha, or compared to compounds of the formula V in a concentration range of 0.5-120, in particular 1-60 and very particularly 3-30 g ai / ha.
Der Begriff „Saat- oder Vermehrungsgut" beinhaltet sowohl vegetatives als auch geschlechtliches Vermehrungsgut wie Früchte, Samen, Knollen, Wurzelstöcke, Sämlinge, Stecklinge, Calli, Protoplasten, Zellkulturen etc..The term "seed or propagation material" includes both vegetative and sexual propagation material such as fruits, seeds, tubers, rhizomes, seedlings, cuttings, calli, protoplasts, cell cultures etc.
Unter dem Begriff „Zuckerrübe" sind nicht nur ganze Pflanzen zu verstehen, die durch Selektion erhalten bzw. erzeugt werden können, sondern ggf. auch deren Teile wie Wurzeln, Blätter, Stengel, Knollen und weitere Zellverbände sowie von diesen Pflanzen abstammende Generationen oder Zellen.The term "sugar beet" is not only to be understood as whole plants which can be obtained or produced by selection, but also, if appropriate, their parts such as roots, leaves, stems, tubers and other cell assemblies and generations or cells derived from these plants.
Der Begriff „erfindungsgemäße Zuckerrübenkultur" umfaßt im allgemeinenThe term "sugar beet culture according to the invention" generally includes
Kulturen der erfindungsgemäßen Zuckerrübenmutanten und deren Saat- oder Vermehrungsgut sowie ggf. auch die Anbauflächen solcher Pflanzen.Cultures of the sugar beet mutants according to the invention and their seeds or propagation material and, if appropriate, also the areas under cultivation of such plants.
Die erfindungsgemäßen Merkmale der Sulfonylhamstoffresistenten Zuckerrübenmutanten können auch in z.B. transgene Zuckerrüben nach herkömmlichen, dem Fachmann bekannten Züchtungsverfahren eingekreuzt werden.The features of the sulfonylurea-resistant sugar beet mutants according to the invention can also be found in e.g. transgenic sugar beets are crossed using conventional breeding methods known to those skilled in the art.
Die transgenen Pflanzen, die z.B. für eine Kreuzung besonders bevorzugt geeignet sein können, zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch einen gesteigerten Ertrag, Resistenzen gegenüber bestimmten Pestiziden, vor allem gegenüber bestimmten Herbiziden
oder Schadinsekten, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Milben oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere Eigenschaften betreffen z. B. auch das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung oder spezieller Inhaltsstoffe.The transgenic plants, which can be particularly preferred, for example, for a cross, are generally distinguished by particularly advantageous properties, for example by an increased yield, resistance to certain pesticides, especially to certain herbicides or insect pests, resistance to plant diseases or pathogens such as certain insects or mites or microorganisms such as fungi, bacteria or viruses. Other properties concern e.g. B. also the crop in terms of quantity, quality, shelf life, composition or special ingredients.
Wege zur Herstellung transgener Pflanzen, die im Vergleich zu bisher natürlich vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen neben klassischen Züchtungsverfahren und der Erzeugung von Mutanten beispielsweise in der Anwendung gentechnischer Verfahren (siehe z. B. EP-A-0221044, EP-A-0131624). Beschrieben wurden beispielsweise die Herstellung von gentechnisch modifizierten Pflanzen in bezug auf Modifikationen des pflanzlichen Kohlenhydratstoffwechsels (z. B. WO 94/28146, WO 92/11376, WO 92/14827, WO 91/19806), Resistenzen gegen bestimmte Herbizide, z.B. vom Typ Glufosinate (vgl. z. B. EP-A-0242236, EP-A-242246) oder Glyphosate (z.B. WO 92/00377), Resistenzen gegen bestimmte Schädlinge, z.B. aufgrund der Fähigkeit bestimmte Bacillus thuringiensis-Toxine (Bt-Toxine) oder Protease-Inhibitoren zu produzieren (z.B. EP-A-0142924, EP-A-0193259).In addition to classic breeding methods and the generation of mutants, methods of producing transgenic plants which have modified properties compared to previously naturally occurring plants exist, for example, in the use of genetic engineering processes (see, for example, EP-A-0221044, EP-A-0131624 ). For example, the production of genetically modified plants with respect to modifications of the vegetable carbohydrate metabolism (e.g. WO 94/28146, WO 92/11376, WO 92/14827, WO 91/19806), resistance to certain herbicides, e.g. of the glufosinate type (see e.g. EP-A-0242236, EP-A-242246) or glyphosate (e.g. WO 92/00377), resistance to certain pests, e.g. due to the ability to produce certain Bacillus thuringiensis toxins (Bt toxins) or protease inhibitors (e.g. EP-A-0142924, EP-A-0193259).
Insbesondere sind transgene Zuckerrüben mit einem veränderten Saccharose- Gehalt durch Modifikationen der Genexpression der Enzyme ADP-Glukose- Pyrophosphorylase, Sucrosephosphat-Synthase und Sucrose-Synthase aus der WO 94/28146 bekannt.In particular, transgenic sugar beet with an altered sucrose content through modifications of the gene expression of the enzymes ADP-glucose pyrophosphorylase, sucrose phosphate synthase and sucrose synthase are known from WO 94/28146.
Mit den erfindungsgemäßen Verfahren zur Kontrolle (Bekämpfung) von unerwünschtem Pflanzenwuchs kann ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler Schadpflanzen hervorragend bekämpft werden. Auch schwer bekämpfbare perennierende Unkräuter, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Verfahren ausgezeichnet erfaßt. Dabei ist es gleichgültig, ob die Substanzen oder Mittel im Vorsaat-,A wide range of economically important monocotyledonous and dicotyledonous harmful plants can be combated excellently with the methods according to the invention for controlling (controlling) undesired plant growth. Perennial weeds which are difficult to control and which sprout from rhizomes, rhizomes or other permanent organs are also recorded with excellent results. It does not matter whether the substances or agents are used in pre-sowing,
Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielsweise einige Vertreter der mono- und dikotylen Unkrautflora genannt, die
durch die erfϊndungsgemäßen Verfahren kontrolliert werden können, ohne daß durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll.Pre-emergence or post-emergence procedures are applied. In particular, some representatives of the monocotyledonous and dicotyledonous weed flora may be mentioned, the can be controlled by the methods according to the invention, without any restriction to certain types being intended by the naming.
Auf der Seite der monokotylen Unkrautarten werden z.B. Avena, Lolium, Alopecurus, Apera, Poa, Phalaris, Echinochloa, Digitaria, Setaria sowie Cyperusarten aus der annuellen Gruppe und auf seifen der perennierenden Spezies Agropyron, Cynodon, Sorghum, ausdauernde Cyperusarten und auch Ausfallgetreide wie Weizen, Gerste usw. gut erfaßt.On the side of the monocot weed species, e.g. Avena, Lolium, Alopecurus, Apera, Poa, Phalaris, Echinochloa, Digitaria, Setaria as well as Cyperus species from the annual group and on soaps of the perennial species Agropyron, Cynodon, Sorghum, perennial Cyperus species and also crops such as wheat, barley etc.
Bei dikotylen Unkrautarten erstreckt sich das Wirkungsspektrum auf Arten wie z.B. Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Matricaria, Abutilon, Polygonum, Galinsoga, Mercurialis, Solanum, Chinopodium, Kochia, Anthemis und Sonchus auf der annuellen Seite sowie Convolvulus, Cirsium und Rumexbei den perennierenden Unkräutern und auch Ausfallkulturen wie Kartoffel, Raps usw..With dicotyledon weed species, the spectrum of activity extends to species such as Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Matricaria, Abutilon, Polygonum, Galinsoga, Mercurialis, Solanum, Chinopodium, Kochia, Anthemis and Sonchus on the annual side as well as Convolvulus, Cirsium and Rumex for the perennial weeds and also crops such as Potato, rapeseed etc.
Werden in den erfindungsgemäßen Verfahren die Verbindungen oder Mittel vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimiinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab.If the compounds or agents are applied to the surface of the earth before germination in the process according to the invention, either weed germination is completely prevented or the weeds grow up to the cotyledon stage, but then stop growing and finally die after three to four Weeks off completely.
Bei Applikation der Wirkstoffe oder Mittel auf die grünen Pflanzenteile im Nachauflaufverfahren tritt ebenfalls sehr rasch nach der Behandlung ein drastischer Wachstumsstop ein und die Unkrautpflanzen bleiben in dem zumWhen the active ingredients or agents are applied to the green parts of the plants in the post-emergence process, there is also a drastic growth stop very quickly after the treatment and the weed plants remain in the
Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so daß auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird.At the time of application, the existing growth stage stands or dies completely after a certain time, so that weed competition which is harmful to the crop plants is eliminated very early and sustainably.
In den erfindungsgemäßen Zuckerrübenkulturen sind durch geeignete Applikation der herbiziden Wirkstoffe bzw. deren Kombinationen die folgenden, bislang besonders schwer bekämpfbaren Schadpflanzen wie Anthemis, Agropyron,
Chinopodium, Cirsium, Kochia, Polygonum, Matriciaria, sowie Durchwuchs/Ausfallkulturen und im allgemeinen auch Unkräuter in späteren Wachstumsstadien gut, d.h. vorzugsweise zu >80% und insbesondere zu >90% zu kontrollieren.In the sugar beet crops according to the invention, by suitable application of the herbicidal active compounds or combinations thereof, the following harmful plants, such as Anthemis, agropyron, Chinopodium, cirsium, kochia, polygonum, matriciaria, as well as growth / failure crops and generally weeds in later growth stages well, ie preferably> 80% and especially> 90% to be controlled.
Obgleich mit den erfindungsgemäßen Verfahren eine ausgezeichnete herbizide Wirkung gegenüber mono- und dikotylen Unkräutern erreicht wird, werden die erfindungsgemäßen Kulturpflanzen nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verfahren eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Kulturen der erfindungsgemäßen Zuckerrübenmutanten.Although an excellent herbicidal action against mono- and dicotyledon weeds is achieved with the methods according to the invention, the crop plants according to the invention are only insignificantly or not at all damaged. For these reasons, the present methods are very well suited for the selective control of undesired plant growth in agricultural crops of the sugar beet mutants according to the invention.
Darüber hinaus werden mit den erfindungsgemäßen Verfahren hervorragende zusätzliche Effekte in den erfindungsgemäßen Zuckerrüben erzielt. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Förderung von Pflanzeninhaltsstoffen und des Ernteertrages eingesetzt werden.In addition, excellent additional effects are achieved in the sugar beets according to the invention with the methods according to the invention. They intervene regulating the plant's own metabolism and can thus be used for the targeted promotion of plant constituents and harvest yield.
Die in dem erfindungsgemäßen Verfahren eingesetzten Verbindungen oder Mittel können in Form von Spritzpulvern, emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden und können auf verschiedene Art formuliert sein, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie öl-in-Wasser- und Wasser-in-öl-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Mikrokapseln und Wachse.
Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufl. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.The compounds or agents used in the process according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations and can be formulated in various ways, depending on the biological and / or chemical-physical parameters specified are. Possible formulation options include: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator - and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th Edition 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY , 1973, K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Fungiziden, Safenern, Düngemitteln und/oder Wachstumsregulatoren appiizieren, z.B. in Form einer Fertigformulierung oder als Tankmix.Based on these formulations, combinations with other pesticidally active substances, e.g. Apply insecticides, acaricides, fungicides, safeners, fertilizers and / or growth regulators, e.g. in the form of a finished formulation or as a tank mix.
Die agrochemischen Zubereitungen enthalten in der Regel 0,1 bis 99 Gew.-%, insbesondere 1 bis 95 Gew.-%, Wirkstoffe oder deren Salze.The agrochemical preparations generally contain 0.1 to 99% by weight, in particular 1 to 95% by weight, of active ingredients or their salts.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formuiierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten 1 bis 30, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen etwa 0,05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%.The active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation ingredients. In the case of emulsifiable concentrates, the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight. Dust-like formulations contain 1 to 30, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions about 0.05 to 80, preferably 2 to 50% by weight of active ingredient. In the case of water-dispersible granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used. The active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-,In addition, the active ingredient formulations mentioned may contain the usual adhesive, wetting, dispersing, emulsifying, penetrating,
Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH-Wert und die Viskosität
beeinflussende Mittel.Preservatives, antifreeze and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH value and viscosity influencing means.
In den erfindungsgemäßen Verfahren sind die herbiziden Kombinationspartner der Gruppe B (B1 bis B9) mit den Sulfonylharnstoffen der Gruppe A (A1 bis A18) in Mischungsformulierungen oder im Tank-Mix einsetzbar, beispielsweise bekannte Wirkstoffe, wie sie z.B. in Weed Research 26, 441-445 (1986), oder "The Pesticide Manual", 11th edition, The British Crop Protection Council, 1997, Bracknell, England, und der dort zitierten Literatur beschrieben sind. Die einzelnen, unter A4 bis A17 und B1 bis B9 aufgeführten Verbindungen sind in der Regel mit dem "common name" nach der International Organization for Standard ization (ISO) bezeichnet.In the processes according to the invention, the herbicidal combination partners of group B (B1 to B9) with the sulfonylureas of group A (A1 to A18) can be used in mixture formulations or in a tank mix, for example known active compounds, such as those e.g. in Weed Research 26, 441-445 (1986) or "The Pesticide Manual", 11th edition, The British Crop Protection Council, 1997, Bracknell, England, and the literature cited therein. The individual compounds listed under A4 to A17 and B1 to B9 are generally designated with the "common name" according to the International Organization for Standardization (ISO).
Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicher Weise verdünnt, z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser, und anschließend auf die Pflanzen, Pflanzenteile oder den landwirtschaftlich genutzten Boden, auf dem die Pflanzen stehen oder in dem sie heranwachsen oder als Saat vorliegen, appiiziert. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt.For use, the formulations present in the commercial form are optionally diluted in the customary manner, e.g. in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water, and then applied to the plants, parts of plants or the agricultural soil on which the plants stand or in which they grow or are present as seeds. Preparations in the form of dust, ground granules or scattering granules and sprayable solutions are usually no longer diluted with other inert substances before use.
Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids, u.a. variiert die erforderliche Aufwandmenge der herbiziden Verbindungen innerhalb weiter Grenzen, z.B. zwischen 0,001 und 10,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,005 und 5 kg/ha.With the external conditions such as temperature, humidity, the type of herbicide used, etc. the required application rate of the herbicidal compounds varies within wide limits, e.g. between 0.001 and 10.0 kg / ha or more of active substance, but it is preferably between 0.005 and 5 kg / ha.
Die nachfolgenden Beispiele sollen die vorliegende Erfindung illustrieren und stellen insofern keine Beschränkung dar.
Beispiel 1 : Etablierung morphogener Zuckerrübenzellkulturen auf aminosäurefreiem NährmediumThe following examples are intended to illustrate the present invention and thus do not constitute a limitation. Example 1: Establishment of morphogenic sugar beet cell cultures on amino acid-free nutrient medium
Reife Zuckerrübensamen wurden nach erfolgter Desinfektion der Samenoberfläche auf hormonfreiem Medium unter aseptischen Bedingungen zum Keimen gebracht.Ripe sugar beet seeds were germinated after the disinfection of the seed surface on hormone-free medium under aseptic conditions.
Das modifizierte Medium nach Murashige-Skoog (MS-Medium), das für die Experimente verwendet wurde, ist in Tabelle 1 wiedergeben. Vor dem Autoklavieren wurde der pH-Wert des Mediums auf 5,8 eingestellt. Die Vitamine wurden vor dem Autoklavieren (120°C; 15 min) dem Medium zugegeben. Die Phytohormonkonzentrationen wurden für die Kallusinitiation, Kallussubkultur und Pflanzenregeneration wie im Text beschrieben variiert.The modified Murashige-Skoog medium (MS medium) used for the experiments is shown in Table 1. The pH of the medium was adjusted to 5.8 before autoclaving. The vitamins were added to the medium before autoclaving (120 ° C; 15 min). The phytohormone concentrations were varied for callus initiation, callus subculture and plant regeneration as described in the text.
Tabelle 1 MS-Medium mg/LTable 1 MS medium mg / L
MgS04 * 7H20 370MgSO 4 * 7H 2 0 370
CaCI2 * 2H20 440CaCI 2 * 2H 2 0 440
KN03 1900KN0 3 1900
(NH4)2S04 —(NH 4 ) 2 S0 4 -
NH4N03 1650NH 4 N0 3 1650
KH2P04 170KH 2 P0 4 170
MnS04 22,3MnS0 4 22.3
KJ 0,86KJ 0.86
CoCI2 * 6H20 0,025CoCI 2 * 6H 2 0 0.025
ZnS04 * 7HsO 8,6ZnS0 4 * 7H s O 8.6
CuS04 * 5H20 0,025CuS0 4 * 5H 2 0 0.025
H3B03 6,2H 3 B0 3 6.2
Na2Mo04 * 2H20 0,25Na 2 Mo0 4 * 2H 2 0 0.25
EDTA 37,3EDTA 37.3
FeS04 * 7H20 27,3FeS0 4 * 7H 2 0 27.3
Thiamin * Hcl 0,5
Fortsetzung Tabelle 1 MS-MediumThiamine * Hcl 0.5 Continued Table 1 MS medium
Nicotinsäure 0,2Nicotinic acid 0.2
Cyanocobalamin 0,1Cyanocobalamin 0.1
Pyridoxin 0,2 p-Aminobenzosäure 0,05Pyridoxine 0.2 p-aminobenzoic acid 0.05
Ca-Panthothenat 0,1Ca panthothenate 0.1
Biotin 0,1Biotin 0.1
Folsäure 0,05Folic acid 0.05
Nicotinsäure 0,2Nicotinic acid 0.2
Cholin HCI 0,1Choline HCI 0.1
Riboflavin 0,05Riboflavin 0.05
Inosit 100Inositol 100
Saccharose 30000Sucrose 30000
Agar 7000Agar 7000
Naphtylessigsäure 0,1Naphtylacetic acid 0.1
Benzylaminopurin 1 ,0Benzylaminopurine 1,0
Sobald die Keimblätter entfaltet waren, wurden sie abgetrennt und in 4-6 mm lange Stücke geschnitten. Die Hypocotylabschnitte wurden ebenfalls in 4-6 mm große Stücke zerlegt. Die Explantate wurden auf MS-Medium mit einem Gehalt von 0,05-0,5 mg Naphtylessigsäure pro Liter Medium bei 25±2°C im 12h Licht/Dunkelrhythmus bei ca. 500-2000 lux kultiviert. Explantate einiger Sämlinge bildeten unter diesen Bedingungen innerhalb von 2-3 Wochen morphogenen Kallus, der sich auf dem jeweiligen Medium unter Beibehaltung seiner Regenerationsfähigkeit über Monate subkultivieren ließ.Once the cotyledons were unfolded, they were separated and cut into 4-6 mm pieces. The hypocotyl sections were also cut into 4-6 mm pieces. The explants were cultivated on MS medium with a content of 0.05-0.5 mg naphthylacetic acid per liter medium at 25 ± 2 ° C in a 12 hour light / dark rhythm at approx. 500-2000 lux. Under these conditions, explants from some seedlings formed morphogenic callus within 2-3 weeks, which could be subcultured on the respective medium for months while maintaining its regenerative capacity.
Es wurden Zellinien etabliert, die auf dem in Tabelle 1 beschriebenen Medium länger als ein Jahr unter Beibehaltung der Regenerationsfähigkeit wachsen können.
Beispiel 2: In vitro MutageneseCell lines have been established which can grow on the medium described in Table 1 for more than one year while maintaining the ability to regenerate. Example 2: In vitro mutagenesis
Morphogene Zuckerrübenkallusstücke werden in MS-Medium mit 0,1 bis 1% Ethylmethansulfonat 10 bis 120 min. inkubiert, 3 x gewaschen und in dem Medium kultiviert. Die überlebenden morphogenen Kallussegmente werden nach 2 bis 4 Wochen auf frischem Medium subkultiviert. Nach weiteren 2 bis 4 Wochen können die Kalli für Selektionsexperimente herangezogen werden.Morphogenic sugar beet callus pieces are in MS medium with 0.1 to 1% ethyl methanesulfonate for 10 to 120 min. incubated, washed 3 times and cultivated in the medium. The surviving morphogenic callus segments are subcultured on fresh medium after 2 to 4 weeks. After a further 2 to 4 weeks, the calli can be used for selection experiments.
Beispiel 3: Selektion herbizidresistenter KalluskulturenExample 3: Selection of herbicide-resistant callus cultures
Es wird zunächst ermittelt bei welcher Herbizidkonzentration im Medium 95 bis 99 % der Kalli absterben.It is first determined at which herbicide concentration in the medium 95 to 99% of the calli die off.
Es werden jeweils 1000 Kalli auf die herbizidhaltigen (LD98) Agar-Medien (0,8% Agar) transferiert und nach 6 bis 8 Wochen evaluiert. Die Petrischalen werden bei 12 h Beleuchtung pro Tag mit 1000 bis 2000 Lux und 25°C inkubiert. In den Medien mit den Herbiziden bilden sich Kalli aus, die unter Ausbildung von Sproßprimordien wachsen.1000 calli are transferred to the herbicidal (LD 98 ) agar media (0.8% agar) and evaluated after 6 to 8 weeks. The Petri dishes are incubated at 12 to 2000 lux and 25 ° C per day. Calli are formed in the media with the herbicides, which grow with the formation of shoot primordia.
Durch wiederholte Subkultur der resistenten morphogenen Kalli können Zellinien etabliert werden, die eine relativ hohe Herbizidkonzentrationen tolerieren und zur Pflanzenregeneration befähigt sind.Through repeated subculture of the resistant morphogenic calli, cell lines can be established that tolerate a relatively high herbicide concentration and are capable of plant regeneration.
Beispiel 4: PflanzenregenerationExample 4: Plant regeneration
Auf Regenerationsmedium (Medium ohne Naphtylessigsäure) differenzieren sich aus den erhaltenen embryogenen herbizidverträglichen Kalli innerhalb von 1-2 Subkulturperioden (1-2 Monate) Sproße aus, die auf hormonfreiem Medium (d.h. ohne Naphtylessigsäure und Benzylaminopurin (BAP)) während der folgenden 1- 3 Subkulturen bewurzeln. Sobald sich genügend Wurzeln gebildet haben, werden die Pflanzen in ein anorganisches Substrat (z.B. Vermiculit oder Periit) überführt, nachdem die Agarreste möglichst vollständig aus den Wurzeln entfernt wurden.
Während der ersten 3-6 Tage werden die Pflanzen bei 90 bis 100% relativer Luftfeuchte kultiviert. Danach können die Pflanzen entweder in der Klimakammer oder im Gewächshaus weiterkultiviert werden. Bis zur Ausbildung von weiteren 2 bis 4 Blättern, werden die Regenerate in Hydrokultur gehalten. Danach können die Zuckerrübenmutanten in Erde verpflanzt werden.On regeneration medium (medium without naphthylacetic acid) sprouts differentiate from the embryogenic herbicide-compatible calli obtained within 1-2 subculture periods (1-2 months), which on hormone-free medium (ie without naphthylacetic acid and benzylaminopurine (BAP)) during the following 1-3 Root subcultures. As soon as enough roots have formed, the plants are transferred to an inorganic substrate (eg vermiculite or periite) after the agar residues have been removed as completely as possible from the roots. During the first 3-6 days, the plants are cultivated at 90 to 100% relative humidity. The plants can then be cultivated either in the climatic chamber or in the greenhouse. The regenerates are kept in hydroponic until a further 2 to 4 leaves are formed. The sugar beet mutants can then be transplanted into soil.
Beispiel 5: Selektion von Sulfonylhamstofftoleranten Zuckerrübenmutanten in Gegenwart von Herbizid und Safener.Example 5: Selection of sulfonylurea tolerant sugar beet mutants in the presence of herbicide and safener.
2 g einer Zellsuspension des regenerationsfähigen Zuckerrübengenotyps Rel2 wurden in Gegenwart von 1 x 10-5 M 5,5-Diphenyl-2-isoxazolin-3-carbonsäure- ethylester (DIC) als Safener und 1 x 10-5 M 1-[3-(N-Ethyl-N-formyl-amino)-pyrid-2- yl-sulfonyl]-3-(4,6-dimethoxy-pyrimidin-2-yl)-harnstoff (SH) als Herbizid in 20 ml MS-Medium kultiviert. Dem MS-Medium wurden je 0,5 mg/l Benzylaminopurin und 2,4-D (2,4-Dichlorphenoxy-essigsäure) zugefügt. Die Zellsuspenison wurde 7 Tage lang bei 25 °C in einem Schüttler bei 120 rpm kultiviert.2 g of a cell suspension of the regenerable sugar beet genotype Rel2 were in the presence of 1 x 10-5 M 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (DIC) as safener and 1 x 10-5 M 1- [3- (N-Ethyl-N-formylamino) pyrid-2-yl-sulfonyl] -3- (4,6-dimethoxy-pyrimidin-2-yl) urea (SH) cultivated as a herbicide in 20 ml of MS medium . 0.5 mg / l benzylaminopurine and 2,4-D (2,4-dichlorophenoxyacetic acid) were added to the MS medium. The cell suspension was cultivated for 7 days at 25 ° C. in a shaker at 120 rpm.
Nach 7 Tagen wurden 20 ml frisches MS Medium der genannten Zusammensetzung ohne SH hinzugefügt und die Kultur fortgesetzt. Nach weiteren 7 Tagen wurden nach dem Absedimentieren der Zellen 20 ml des zellfreien Überstands abgesaugt und durch frisches MS Medium (ohne Herbizid, aber mit 10"5 M Safener) ersetzt. Nach weiteren 7 Tagen wurde dieser Vorgang wiederholt.After 7 days, 20 ml of fresh MS medium of the composition mentioned without SH were added and the culture was continued. After a further 7 days, after the cells had been sedimented, 20 ml of the cell-free supernatant were aspirated and replaced by fresh MS medium (without herbicide, but with 10 "5 M safener). This process was repeated after a further 7 days.
Nach Ablauf der 4. Subkulturperiode wurden die Zellen 2 x mit Safener- und herbizidfreiem Medium gewaschen, in 20 ml MS-Medium aufgenommen und auf Agarmedium ausplattiert. Das Agarmedium enthielt MS-Salze, Vitamine und übliche Spurenelemente, 20 g Saccharose, 0,8 % Agar, 0,5 mg/l BAP und 0,5 mg/l 2.4.-D pH 5.8.
Dem Medium wurden folgende Zusätze zugegeben:After the fourth subculture period had ended, the cells were washed twice with safener-free and herbicide-free medium, taken up in 20 ml of MS medium and plated out on agar medium. The agar medium contained MS salts, vitamins and usual trace elements, 20 g sucrose, 0.8% agar, 0.5 mg / l BAP and 0.5 mg / l 2.4.-D pH 5.8. The following additives were added to the medium:
1) keine1) none
2) 1 x 10-° M SH 3) 2,5 x 10"6 M SH2) 1 x 10- ° M SH 3) 2.5 x 10 "6 M SH
4) 1 x 10-° M SH + 1 x 10'5 M DIC4) 1 x 10- ° M SH + 1 x 10 '5 M DIC
5) 2.5 x 10^ M SH + 1 x 10-° M DIC5) 2.5 x 10 ^ M SH + 1 x 10- ° M DIC
Nach 6 Wochen wurde die Anzahl der Zellkolonien durch Auszählen ermittelt. Das Ergebnis ist in Tabelle 2 wiedergegeben.After 6 weeks, the number of cell colonies was determined by counting. The result is shown in Table 2.
Tabelle 2: Anzahl der Zellkolonien (Anzahl/10 Petrischalen)Table 2: Number of cell colonies (number / 10 petri dishes)
Die herbizid-toleranten Zeilklone (Medien 2-5) wurden auf Regenerationsmedium (MS-Medium mit 1 mg/l BAP und 0,05 mg/l Naphthylphenoxyessigsäure (NAA)) zur Sproßbildung induziert. Die in vitro Sprosse wurden auf Medium mit 0,05 mg/l NAA in einem 2. Schritt zur Wurzelbildung induziert. Die bewurzelten Pflanzen konnten nach ca. 8 - 12 Wochen in Erde überführt werden.The herbicide-tolerant cell clones (media 2-5) were induced on regeneration medium (MS medium with 1 mg / l BAP and 0.05 mg / l naphthylphenoxyacetic acid (NAA)) for sprout formation. The in vitro shoots were induced on medium with 0.05 mg / l NAA in a second step for root formation. The rooted plants could be transferred into soil after approx. 8 - 12 weeks.
Biologische BeispieleBiological examples
Beispiel 6: Herbizidapplikation
Im 4. und 5. Blattstadium werden die Pflanzen mit Herbizidlösungen in praxisüblichen Aufwandmengen besprüht. Die Herbizide werden als 0,1 bis 1 %ige wäßrige Lösungen appliziert. Die behandelten Pflanzen werden nach 14 bis 28 Tagen visuell bonitiert. Der Test auf Herbizidresistenz wird unter Bedingungen durchgeführt, die bei kommerziellen (Kontrollpflanzen) zu einer schweren Schädigung (Schädigungsgrad >80 %) führen.Example 6: Herbicide Application In the 4th and 5th leaf stages, the plants are sprayed with herbicide solutions in customary application rates. The herbicides are applied as 0.1 to 1% aqueous solutions. The treated plants are rated visually after 14 to 28 days. The test for herbicide resistance is carried out under conditions which lead to serious damage (degree of damage> 80%) in commercial (control plants).
Die Regeneratpflanzen zeigen eine gut ausgeprägte Toleranz gegenüber den applizierten Sulfonylharnstoffen, d.h. eine vergleichsweise geringe Schädigung.The regenerated plants show a good tolerance towards the applied sulfonylureas, i.e. comparatively little damage.
Beispiel 7: Herbizidwirkung an Schadpflanzen in Kulturen von ZuckerrübenmutantenExample 7: Herbicidal action on harmful plants in crops of sugar beet mutants
Verschiedene Linien der Regeneratpflanzen werden in Töpfen im Gewächshaus oder im Feld in Kleinparzellen ausgesät und bis zum Stadium von 2-4 Blättern angezogen. Gleichzeitig werden einige Unkräuter bzw. Ungräser ausgesät bzw. durch natürliches Keimen und Auflaufen werden in den Feldparzellen verschiedene Unkrautsituationen (bezüglich Unkräuter und Blattstadien) erreicht.Different lines of the regenerated plants are sown in pots in the greenhouse or in the field in small plots and grown up to the stage of 2-4 leaves. At the same time, some weeds or grass weeds are sown, or due to natural germination and emergence, different weed situations (with regard to weeds and leaf stages) are achieved in the field plots.
Nach Behandlung mit den Sulfonylharnstoffen der Gruppe A und ggf. in Kombination mit Herbiziden der Gruppe B werden im weiteren Verlauf des Wachstums in Zeitabständen von 3-6 Wochen Bonituren der herbiziden Effektivität vorgenommen, um die Selektivität der verschiedenen Wirkstoffe und ihre herbizide Wirksamkeit zu beurteilen.After treatment with the group A sulfonylureas and, if appropriate, in combination with group B herbicides, herbicidal effectiveness is assessed at intervals of 3-6 weeks as the growth progresses in order to assess the selectivity of the various active compounds and their herbicidal activity.
Die Ergebnisse dieser Versuche zeigen, daß die Herbizide bzw. Herbizidkombinationen an den erfindungsgemäßen Zuckerrübenmutanten besonders gut verträglich sind, aber gleichzeitig hervorragende herbizide Wirksamkeit gegen unerwünschte breitblättrige und grasartige Unkräuter aufweisen und somit eine selektive Unkrautbekämpfung in den erfindungsgemäßen Zuckerrübenkulturen ermöglicht wird.
The results of these experiments show that the herbicides or combinations of herbicides on the sugar beet mutants according to the invention are particularly well tolerated, but at the same time have excellent herbicidal activity against undesired broad-leaved and grass-like weeds and thus selective weed control in the sugar beet crops according to the invention is made possible.
Claims
1. Sulfonylhamstoff-tolerante Zuckerrübenmutante, deren Saat- oder1. sulfonylurea-tolerant sugar beet mutant, its seed or
Vermehrungsgut oder deren Zellen, dadurch gekennzeichnet, daß sie tolerant sind gegenüber einem oder mehreren Sulfonylharnstoffen ausgewählt aus derPropagation material or their cells, characterized in that they are tolerant to one or more sulfonylureas selected from the group
Gruppe A bestehend ausGroup A consisting of
A1 ) Verbindungen der Formel (I) und deren anorganische oder organischeA1) Compounds of formula (I) and their inorganic or organic
Salze,Salts,
worinwherein
Q Sauerstoff, Schwefel oder -N(R4)-,Q oxygen, sulfur or -N (R 4 ) -,
Y CH oder N, R Wasserstoff (H), (CrC12)-Alkyl; (C2-C10)-Alkenyl; (C2-C10)-Alkinyl; (CrC8)- Alkyl, das ein- bis vierfach durch Reste aus der Gruppe Halogen, (C C4)- Alkoxy, (CrC4)-Thioalkyl, CN, (C2-C3)-Alkoxycarbonyl und (C2-Cβ)-Alkenyl substituiert ist; oder (C3-C8)-Cycloalkyl, das unsubstituiert oder durch Reste aus der Gruppe (CrC4)-Alkyl, (C C4)-Alkoxy, (CrC4)-Alkylthio und Halogen substituiert ist; (C5-C8)-Cydoalkenyl; Phenyl-(C1-C4)-alkyl, das imY is CH or N, R is hydrogen (H), (C r C 12 ) alkyl; (C 2 -C 10 ) alkenyl; (C 2 -C 10 ) alkynyl; (C r C 8 ) - alkyl, which is mono- to quadruple by residues from the group halogen, (CC 4 ) - alkoxy, (C r C 4 ) -thioalkyl, CN, (C 2 -C 3 ) -alkoxycarbonyl and ( C 2 -C β ) alkenyl is substituted; or (C 3 -C 8 ) cycloalkyl which is unsubstituted or substituted by radicals from the group (C r C 4 ) alkyl, (CC 4 ) alkoxy, (C r C 4 ) alkylthio and halogen; (C 5 -C 8 ) -Cydoalkenyl; Phenyl- (C 1 -C 4 ) alkyl, which in
Phenylrest unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (C1-C4)-Alkyl, (CrC4)-Alkoxy, (CrC4)-Haloalkyl, (CrC4)- Thioalkyl, (C2-C5)-Alkoxycarbonyl, (C2-C5)-Alkylcarbonyloxy, Carbonamid, (C2-C5)-Alkylcarbonylamino, (C2-C5)-Alkylaminocarbonyl, Di-[(C C4)-alkyl]- carbonyl und Nitro substituiert ist; oder einen Rest der Formeln A-1 bis A-Phenyl radical unsubstituted or by one or more radicals from the group halogen, (C 1 -C 4 ) -alkyl, (C r C 4 ) -alkoxy, (C r C 4 ) -haloalkyl, (C r C 4 ) -thioalkyl, (C 2 -C 5 ) alkoxycarbonyl, (C 2 -C 5 ) alkylcarbonyloxy, carbonamide, (C 2 -C 5 ) alkylcarbonylamino, (C 2 -C 5 ) alkylaminocarbonyl, di - [(CC 4 ) - alkyl] - carbonyl and nitro is substituted; or a radical of the formulas A-1 to A-
A-4 A-5 A-6 A-7A-4 A-5 A-6 A-7
A-8 A-9 A-10A-8 A-9 A-10
worin X O, S, S(0) oder S02;wherein XO, S, S (0) or S0 2 ;
R1 Wasserstoff oder (CrC3)-Alkyl; R2 Wasserstoff, Halogen, (C,-C3)-Alkyl oder (CrC3)-Alkoxy, wobei die beiden letztgenannten Reste unsubstituiert oder durch ein- oder mehrfach durch Halogen oder (C1-C3)-Alkoxy substituiert sind;R 1 is hydrogen or (C r C 3 ) alkyl; R 2 is hydrogen, halogen, (C, -C 3 ) alkyl or (C r C 3 ) alkoxy, the latter two radicals being unsubstituted or substituted one or more times by halogen or (C 1 -C 3 ) alkoxy are;
R Wasserstoff, Halogen, (CrC3)-Alkyl, (CrC3)-Alkoxy oder (C C3)-Alkylthio, wobei die vorgenannten alkylhaltigen Reste unsubstituiert oder ein- oder mehrfach durch Halogen oder ein- oder zweifach durch (C C3)-Alkoxy oder (C^C^-Alkylthio substituiert sind; oder einen Rest der Formel NR5R6, (C3- C6)-Cycloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C3-C4)-Alkenyloxy oder (C3- C4)-Alkinyloxy;R is hydrogen, halogen, (C r C 3 ) -alkyl, (C r C 3 ) -alkoxy or (CC 3 ) -alkylthio, where the abovementioned alkyl-containing radicals are unsubstituted or one or more times by halogen or once or twice by ( CC 3 ) alkoxy or (C ^ C ^ alkylthio) are substituted; or a radical of the formula NR 5 R 6 , (C 3 - C 6 ) cycloalkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkynyl, (C 3 -C 4 ) alkenyloxy or (C 3 - C 4 ) alkynyloxy;
R4 Wasserstoff, (C1-C4)-Alkyl oder (CrC4)-Alkoxy und R5 und R6 unabhängig voneinander Wasserstoff, (C C4)-Alkyl, (C3-C4)-Alkenyl, (CrC4)-Haloalkyl oder (CrC4)-Alkoxy bedeuten;
A2) Verbindungen der Formel II und deren anorganische oder organische Salze,R 4 is hydrogen, (C 1 -C 4 ) alkyl or (C r C 4 ) alkoxy and R 5 and R 6 are independently hydrogen, (CC 4 ) alkyl, (C 3 -C 4 ) alkenyl, ( C r C 4 ) haloalkyl or (C r C 4 ) alkoxy; A2) compounds of the formula II and their inorganic or organic salts,
N R R 5 NRR 5
worinwherein
R1 CO-Q-R8,R 1 CO-QR 8 ,
R2 und R3 unabhängig voneinander H oder (C C4)Alkyl,R 2 and R 3 independently of one another are H or (CC 4 ) alkyl,
R4 H, (C C4)Aikyl, Hydroxy oder (C C4)Alkoxy,R 4 H, (CC 4 ) aikyl, hydroxy or (CC 4 ) alkoxy,
R5 (CrC4)Alkylsulfonyl, CHO, [(C1-C4)Alkyl]-carbonyl, das unsubstituiert oder durch ein oder mehrere Halogenatome substituiert ist, [(CrC4)Alkoxy]- oxalyl, [(C3-C6)Cycloalkyl]-carbonyl oder eine Gruppe der FormelR 5 (C r C 4 ) alkylsulfonyl, CHO, [(C 1 -C 4 ) alkyl] carbonyl which is unsubstituted or substituted by one or more halogen atoms, [(C r C 4 ) alkoxy] oxalyl, [( C 3 -C 6 ) cycloalkyl] carbonyl or a group of the formula
W W W oderW W W or
- C - T - R9 -C - NR10R11 oder -C M N/(DR1122\)- C - T - R 9 -C - NR 10 R 11 or -CMN / (DR1 1 2 2 \)
bedeuten, worinmean what
W ein Sauerstoff- oder Schwefelatom (O oder S),W is an oxygen or sulfur atom (O or S),
T O oder S, R9 H, (C1-C4)Alkyl, das unsubstituiert oder durch ein oder mehrere Halogenatome oder durch (C C4)Alkoxy, (C1-C4)Alkylthio, [(C1-C4)Alkoxy]-carbonyl und [(C C4)Alkyl]-carbonyl substituiert ist, R10 und R11 unabhängig voneinander H, (C C4)Alkyl, das unsubstituiert oder durch einoder mehrere Halogenatome substituiert ist, oder (C3-C4)-Alkenyl
oder (C3-C4)Alkinyl, wobei mindestens einer der Reste R10 und R11 vonTO or S, R 9 H, (C 1 -C 4 ) alkyl which is unsubstituted or by one or more halogen atoms or by (CC 4 ) alkoxy, (C 1 -C 4 ) alkylthio, [(C 1 -C 4 ) Alkoxy] carbonyl and [(CC 4 ) alkyl] carbonyl is substituted, R 10 and R 11 independently of one another H, (CC 4 ) alkyl which is unsubstituted or substituted by one or more halogen atoms, or (C 3 -C 4 ) Alkenyl or (C 3 -C 4 ) alkynyl, where at least one of the radicals R 10 and R 11 of
Wasserstoff verschieden ist, die Reste R12 gemeinsam mit dem N-Atom einen heterocyclischen Ring mit 5 oder 6 Ringgliedern, der ein weiteres Heteroatom aus der Gruppe N, O und S in den verschiedenen Oxidationsstufen enthalten kann und unsubstituiert oder durch (C C4)Alkyl oder die Oxogruppe substituiert ist, und Q O, S oder -NR13-, R6 H, (CrC3)Alkyl, (C C3)Alkoxy, Halogen,Hydrogen is different, the radicals R 12 together with the N atom form a heterocyclic ring with 5 or 6 ring members, which may contain a further heteroatom from the group N, O and S in the various oxidation states and are unsubstituted or by (CC 4 ) alkyl or the oxo group is substituted and QO, S or -NR 13 -, R 6 H, (C r C 3 ) alkyl, (CC 3 ) alkoxy, halogen,
R8 unabhängig voneinander (C1-C4)Alkyl, das unsubstituiert oder durch ein oder mehrere Halogenatome substituiert ist, oder (C3-C4)-Alkenyl oder (C3-R 8 independently of one another (C 1 -C 4 ) alkyl which is unsubstituted or substituted by one or more halogen atoms, or (C 3 -C 4 ) alkenyl or (C 3 -
C4)Alkinyl, A einen Rest der FormelC 4 ) alkynyl, A is a radical of the formula
worin Z CH oder N und einer der Reste X und Y Halogen, (C^C^Alkyl, (CrC2)Alkoxy, OCF2H, CF3 oder OCH2CF3 und der andere der Reste X und Y (C C2)Alkyl, (C^C^AIkoxy oder (C1-C2)Haloalkoxy bedeuten, R7 H oder CH3 undwherein Z is CH or N and one of X and Y is halogen, (C ^ C ^ alkyl, (C r C 2 ) alkoxy, OCF 2 H, CF 3 or OCH 2 CF 3 and the other of X and Y (CC 2 ) alkyl, (C ^ C ^ alkoxy or (C 1 -C 2 ) haloalkoxy mean R 7 H or CH 3 and
R13 H, (C^C Alkyl, das unsubstituiert oder durch ein oder mehrereR 13 H, (C ^ C alkyl that is unsubstituted or substituted by one or more
Halogenatome substituiert ist, oder (C3-C4)-Alkenyl oder (C3-C4)Alkinyl bedeuten;
A3) Verbindungen der Formel III, deren N-Oxide und deren anorganische oder organische Salze,Halogen atoms is substituted, or (C 3 -C 4 ) alkenyl or (C 3 -C 4 ) alkynyl; A3) compounds of the formula III, their N-oxides and their inorganic or organic salts,
worinwherein
Ri H, Halogen, (C C4)-Alkyl, das unsubstituiert oder ein- oder mehrfach durchRi H, halogen, (CC 4 ) alkyl, which is unsubstituted or one or more times
Halogen substituiert ist, (C C4)-Alkoxy, (C1-C4)-Alkylthio ;Halogen is substituted, (CC 4 ) alkoxy, (C 1 -C 4 ) alkylthio;
R2 H oder Methyl;R 2 is H or methyl;
R3 Methyl oder Methoxy; A -N-(R4)R5;R 3 is methyl or methoxy; A -N- (R 4 ) R 5 ;
R4 H,
das unsubstituiert oder ein- oder mehrfach durch Halogen,R 4 H, which is unsubstituted or one or more times by halogen,
(CrC6-)-Alkoxy, (C3-C6)-Alkenyloxy, (C3-C6)-Alkinyloxy oder (C C6)-(C r C 6 -) alkoxy, (C 3 -C 6 ) alkenyloxy, (C 3 -C 6 ) alkynyloxy or (CC 6 ) -
Alkylthio substituiert ist;Alkylthio is substituted;
R, H, (C^C -Alkyl, das unsubstituiert oder ein- oder mehrfach durch Halogen,R, H, (C ^ C alkyl, which is unsubstituted or one or more times by halogen,
(C Cβ)-Alkoxy, (C3-C6)-Alkenyloxy, (C3-C6)-Alkinyloxy oder (C C6)-Alklythio substituiert ist, oder C(0)R6;(CC β ) alkoxy, (C 3 -C 6 ) alkenyloxy, (C 3 -C 6 ) alkynyloxy or (CC 6 ) alklythio, or C (0) R 6 ;
RR H, (C^C -Alkyl oder (C3-C6)-Cycloalkyl, die unsubstituiert oder ein- oder mehrfach durch Halogen oder (C1-C4)-Alkoxy substituiert sind, (C2-C6)-R R H, (C 1 -C 4 -alkyl or (C 3 -C 6 ) cycloalkyl which are unsubstituted or substituted one or more times by halogen or (C 1 -C 4 ) alkoxy, (C 2 -C 6 ) -
Alkenyl, das unsubstituiert oder ein- oder mehrfach durch Halogen substituiert ist, (C2-C6)-Alkinyl, Phenyl, Benzyl oder Naphthyl, die unsubstituiert oder ein- oder mehrfach durch Halogen, (CrC4)-Alkyl,Alkenyl which is unsubstituted or mono- or polysubstituted by halogen, (C 2 -C 6 ) -alkynyl, phenyl, benzyl or naphthyl which is unsubstituted or mono- or polysubstituted by halogen, (C r C 4 ) -alkyl,
(C1-C4)-Haloalkyl, (CrC4)-Alkoxy, (C C4)-Haloalkoxy, (C3-C6)-Alkenyloxy,(C 1 -C 4 ) haloalkyl, (C r C 4 ) alkoxy, (CC 4 ) haloalkoxy, (C 3 -C 6 ) alkenyloxy,
(C3-Cβ)-Alkinyloxy, Nitro, Cyano, COOR8, NR10R11 t C(0)NR12R13, X R S,(C 3 -C β ) alkynyloxy, nitro, cyano, COOR 8 , NR 10 R 11 t C (0) NR 12 R 13 , XR S ,
S02NR1βR17 oder durch X2R18 substituiert sind oder OR7;S0 2 NR 1β R 17 or are substituted by X 2 R 18 or OR 7 ;
Rr (C Cβ)-Alkyl, das unsubstituiert oder durch (CrC4)-Alkoxy, (C3-C6)-
Cycloalkyl, Cyano, COOR19, oder CONR26R27 substituiert ist, (CrCβ)- Haloalkyl, (C3-C6)-Alkenyl, (C3-C6)-Haloalkenyl, (C3-C6)-Alkinyl, (C3-Cβ)- Haloalkinyl, Oxetan-3-yl, oder (C4-C6)-Cycloalkyl, das unsubstituiert oder teilweise durch Halogen, (CrC4)-Alkyl oder (C1-C4)-Alkoxy substituiert ist oder Phenyl, Benzyl oder Naphthyl, das unsubstituiert oder jeweils durchRr (CC β ) -alkyl which is unsubstituted or by (C r C 4 ) -alkoxy, (C 3 -C 6 ) - Cycloalkyl, cyano, COOR 19 , or CONR 26 R 27 is substituted, (C r C β ) - haloalkyl, (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) haloalkenyl, (C 3 -C 6 ) -Alkynyl, (C 3 -C β ) - haloalkynyl, oxetan-3-yl, or (C 4 -C 6 ) cycloalkyl, which is unsubstituted or partially substituted by halogen, (C r C 4 ) -alkyl or (C 1 -C 4 ) alkoxy is substituted or phenyl, benzyl or naphthyl, which is unsubstituted or in each case by
(^-C -Alkyl, (CrC4)-Haloalkyl, (C1-C4)-Alkoxy, (CrC4)-Haloalkoxy, (CrC4)- Alkylthio, (Cι-C4)-Haloalkylthio, (CrC4)-Alkylsulfonyl, (CrC4)-Alkylsulfinyl, Nitro, Cyano, COOR^, NR20R21, CONR23R24 oder durch S02NR25R9 substituiert ist; oder (C C6)-Alkyl,
oder X4R30;(C 1 -C 4 -alkyl, (C r C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C r C 4 ) -haloalkoxy, (C r C 4 ) -alkylthio, (Cι-C 4 ) -Haloalkylthio, (C r C 4 ) -alkylsulfonyl, (C r C 4 ) -alkylsulfinyl, nitro, cyano, COOR ^, NR 20 R 21 , CONR 23 R 24 or substituted by S0 2 NR 25 R 9 ; or ( CC 6 ) alkyl, or X 4 R 30 ;
R8 H,
(C3-C6)-Alkenyl, (C3-C6)-Alkinyl oder Oxetan-3-yl;R 8 H, (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl or oxetan-3-yl;
R9- Rio. Rn. Rι2. R13. Ri6. Ri7. R2o. R2ι. R23. R24. R2s. 2e und R27 jeweils unabhängig voneinander H, (C C4)-Alkyl, (C3-C6)-Alkenyl oder (C3-C6)-Alkinyl; oderR 9 - Rio. Marg. R ι 2 . R13. Ri6. Ri7. R 2 or R 2 ι. R 23 . R 24 . R 2 s. 2 e and R 27 each independently of one another are H, (CC 4 ) alkyl, (C 3 -C 6 ) alkenyl or (C 3 -C 6 ) alkynyl; or
Rio und R20 jeweils unabhängig voneinander die Gruppen -C(0)-X5-(CrC4)-Alkyl oder -C(0)-(C1-C4)-Alkyl, die teilweise durch Halogen substituiert sein können; oderRio and R 20 each independently of one another the groups -C (0) -X 5 - (C r C 4 ) alkyl or -C (0) - (C 1 -C 4 ) alkyl, which may be partially substituted by halogen ; or
Rio und R„ oder R12 und R13 oder Rιβ und R17 oder R20 und R2i oder R23 und R24 oder R25 und R9 oder R26 und R27 gemeinsam eine (C4-C5)-Alkylen-Kette bilden, die teilweise durch Sauerstoff oder NR14 unterbrochen sein kann, worinRio and R „or R 12 and R 13 or Rι β and R 17 or R 20 and R 2i or R 23 and R 24 or R 25 and R 9 or R 26 and R 27 together form a (C 4 -C 5 ) - Form alkylene chain, which can be partially interrupted by oxygen or NR 14 , wherein
R14 H, (CrC4)-Alkyl, (C3-C6)-Alkenyl oder (C3-C6)-Alkinyl;R 14 H, (C r C 4 ) alkyl, (C 3 -C 6 ) alkenyl or (C 3 -C 6 ) alkynyl;
Rι5 und R^ jeweils unabhängig voneinander (C C4)-Alkyl oder (Cι-C4)Haloalkyl;R 5 and R ^ each independently of one another (CC 4 ) alkyl or (C 1 -C 4 ) haloalkyl;
R,8 und R30 jeweils unabhängig voneinander durch COOR28 substituiertes (C C4)- Alkyl; Rι9, Rzz und R28 jeweils unabhängig voneinander H oder (Cι-C4)-Alkyl,R, 8 and R 30 are each independently (CC 4 ) alkyl substituted by COOR 28 ; Rι 9 , Rzz and R 28 each independently of one another H or (Cι-C 4 ) alkyl,
X., und X3 jeweils unabhängig voneinander S, SO oder S02;X., and X 3 each independently of one another S, SO or S0 2 ;
X2 und X4 jeweils unabhängig voneinander O oder S;X 2 and X 4 are each independently O or S;
X5 O oder NRM bedeuten;X 5 represents O or NR M ;
A4) Amidosulfuron; A5) Ethoxysulfuron;A4) amidosulfuron; A5) ethoxysulfuron;
A6) Triasulfuron;A6) triasulfuron;
A7) Metsulfuron;
A8) Tribenuron;A7) metsulfuron; A8) tribenuron;
A9) Flupyrsulfuron;A9) flupyrsulfuron;
A10) Nicosulfuron;A10) nicosulfuron;
A11) Rimsulfuron;A11) rimsulfuron;
A12) Primisulfuron;A12) primisulfuron;
A13) Prosulfuron;A13) prosulfuron;
A14) Sulfosulfuron;A14) sulfosulfuron;
A15) Oxasulfuron;A15) oxasulfuron;
A16) Ethametsulfuron;A16) ethametsulfuron;
A17) Imazosulfuron undA17) imazosulfuron and
A18) Verbindungen der Formel V:A18) compounds of the formula V:
Formel V:Formula V:
2. Zuckerrübenmutanten, deren Saat- oder Vermehrungsgut oder deren Zellen gemäß Anspruch 1 , dadurch gekennzeichnet, daß sie durch ein oder mehrere Sulfonylhamstoffe ausgewählt aus der Gruppe A wie in Anspruch 1 definiert in ihrem Wachstum gefördert werden.2. sugar beet mutants, their seeds or propagation material or their cells according to claim 1, characterized in that they are promoted by one or more sulfonylureas selected from group A as defined in claim 1 in their growth.
3. Verfahren zur Herstellung von Sulfonylhamstoff-toleranten Zuckerrübenmutanten gemäß Anspruch 1 oder 2 durch Kultivierung auf einem Sulfonylharnstoff-haltigen Nährmedium, dadurch gekennzeichnet, daß a) Kallus- oder Zellsuspensionskulturen unter Beibehaltung ihrer embryogenen und morphogenen Kompetenz selektioniert werden, b) die unter a) erhaltenen Kulturen auf einem Sulfonylharnstoff-haltigen Nährmedium kultiviert und selektioniert werden und c) aus den unter b) erhaltenen Kulturen intakte Pflanzen regeneriert werden.
3. A process for the production of sulfonylurea-tolerant sugar beet mutants according to claim 1 or 2 by cultivation on a sulfonylurea-containing nutrient medium, characterized in that a) callus or cell suspension cultures are selected while maintaining their embryogenic and morphogenic competence, b) the under a) cultures obtained are cultivated on a sulfonylurea-containing nutrient medium and selected and c) intact plants are regenerated from the cultures obtained under b).
4. Verwendung von Zuckerrübenmutanten erhältlich nach einem Verfahren gemäß Anspruch 3 in der Landwirtschaft, als Futtermittel oder zur Zuckergewinnung.4. Use of sugar beet mutants obtainable by a process according to claim 3 in agriculture, as feed or for sugar production.
5. Verfahren zur Kontrolle von unerwünschtem Pflanzenwuchs in Kulturen von Sulfonylharnstoff-toleranten Zuckerrübenmutanten gemäß einem oder mehreren der Ansprüche 1 bis 2, dadurch gekennzeichnet, daß auf die Pflanzen, deren Saat- oder Vermehrungsgut oder deren Anbaufläche ein oder mehrere Sulfonylhamstoffe ausgewählt aus der Gruppe A wie in Anspruch 1 definiert oder diese enthaltende herbizide Mittel appliziert werden.5. A method for controlling unwanted vegetation in crops of sulfonylurea-tolerant sugar beet mutants according to one or more of claims 1 to 2, characterized in that one or more sulfonylureas selected from group A on the plants, their seeds or propagation material or their cultivated area as defined in claim 1 or herbicidal compositions containing them are applied.
6. Verfahren zur Kontrolle von unerwünschtem Pfianzenwuchs gemäß Anspruch 5, dadurch gekennzeichnet, daß auf die Pflanzen, deren Saat- oder Vermehrungsgut oder deren Anbaufläche zeitgleich oder nachfolgend ein oder mehrere Herbizide ausgewählt aus der Gruppe B bestehend aus B1 ) Herbiziden aus der Klasse der Imidazolinone, vorzugsweise Imazethapyr, Imazamethapyr, Imazapyr, Imazaquin, Imazamox; B2) Herbiziden aus der Klasse der Inhibitoren des photosynthetischen Elektronentransports, vorzugsweise der Biscarbamate, besonders bevorzugt Phenmedipham, Desmedipham;6. A method for controlling undesirable plant growth according to claim 5, characterized in that on the plants, their seeds or propagation material or their cultivated area at the same time or subsequently one or more herbicides selected from group B consisting of B1) herbicides from the class of the imidazolinones , preferably imazethapyr, imazamethapyr, imazapyr, imazaquin, imazamox; B2) herbicides from the class of inhibitors of photosynthetic electron transport, preferably of biscarbamates, particularly preferably phenmedipham, desmedipham;
B3) einem Herbizid aus der Klasse der PPO-Hemmer, z.B. der Diphenyle oder der Azole, Azifluorfen, Oxyfluorfen, Pyraflufen, Carfentrazone, Lactofen, Nitrofen, Oxadiargyl, Fluoroglycofen, Sulfentrazone oder auch ein CF3-Uracil der Formel IV:
B3) a herbicide from the class of the PPO inhibitors, for example the diphenyls or the azoles, azifluorfen, oxyfluorfen, pyraflufen, carfentrazone, lactofen, nitrofen, oxadiargyl, fluoroglycofen, sulfentrazone or else a CF 3 uracil of the formula IV:
B4) einem Herbizid aus der Klasse der Hydroxyphenylpyruvat-Dioxygenase (HPPDO)-Inhibitoren, z.B. der Triketone, vorzugsweise Isoxaflutole, Isoxachlorzole oder Sulcotrione;B4) a herbicide from the class of the hydroxyphenyl pyruvate dioxygenase (HPPDO) inhibitors, e.g. the triketones, preferably isoxaflutole, isoxachlorozole or sulcotrione;
B5) einem Herbizid aus der Klasse der herbizid wirksamen, gegebenenfalls synthetischen Auxine oder deren Transporthemmer, vorzugsweise Quinmerac, Clopyralid, Diflufenzopyr; B6) einem Herbizid aus der Klasse der Lipid- oder der Fettsäure-Synthese- Inhibitoren, vorzugsweise der Aryloxyphenoxycarbonsäuren oder der Cyclohexandionoxime, besonders bevorzugt Fenoxaprop, Haloxyfop, Fluazifop, Quizalofop, Clodinafop, Propaquizafop, Clethodim, Sethoxidim, Tepraloxydim , Butroxidim, Cycloxidim oder Prosulfocarb; B7) einem Herbizid aus der Klasse der Glutamin-Synthetase-Inhibitoren, vorzugsweise Phosphinoaminosäuren, besonders bevorzugt glufosinate; B8) einem Herbizid aus der Klasse der 5-Enolpyruvylshikimat-3-phosphat- Synthase-Inhibitoren, vorzugsweise glyphosate; B9) einem Herbizid aus der Klasse der Benzofuranylalkansulfonate, vorzugsweise Ethofumesate oder diese Verbindungen enthaltende herbizide Mittel appliziert werden.B5) a herbicide from the class of herbicidally active, optionally synthetic auxins or their transport inhibitors, preferably quinmerac, clopyralid, diflufenzopyr; B6) a herbicide from the class of the lipid or the fatty acid synthesis inhibitors, preferably the aryloxyphenoxycarboxylic acids or the cyclohexanedione oximes, particularly preferably fenoxaprop, haloxyfop, fluazifop, quizalofop, clodinafop, propaquizafop, clethodim, sethoxidim, tepraloximocoxime, oxydimoxydoxydoxydoxydoxydoxym, cyclohexane ; B7) a herbicide from the class of glutamine synthetase inhibitors, preferably phosphinoamino acids, particularly preferably glufosinate; B8) a herbicide from the class of the 5-enolpyruvylshikimate-3-phosphate synthase inhibitors, preferably glyphosate; B9) a herbicide from the class of benzofuranylalkanesulfonates, preferably ethofumesates or herbicidal compositions containing these compounds, are applied.
7. Verwendung von einem oder mehreren Sulfonylharnstoffen ausgewählt aus der Gruppe A wie in Anspruch 1 definiert oder diese enthaltende herbizide Mittel auf Anbauflächen von Zuckerrübenkulturen gemäß Anspruch 1 oder 2 zur Schadpflanzenkontrolle.
7. Use of one or more sulfonylureas selected from group A as defined in claim 1 or herbicidal compositions containing them on acreage of sugar beet crops according to claim 1 or 2 for harmful plant control.
8. Verwendung gemäß Anspruch 7 von einem oder mehreren Sulfonylharnstoffen ausgewählt aus der Gruppe A wie in Anspruch 1 definiert, in Kombination mit einem oder mehreren Herbiziden ausgewählt aus der Gruppe B wie in Anspruch 6 definiert oder diese enthaltende herbizide Mittel.8. Use according to claim 7 of one or more sulfonylureas selected from group A as defined in claim 1, in combination with one or more herbicides selected from group B as defined in claim 6 or herbicidal compositions containing them.
9. Verfahren zur Herstellung von Herbizid-toleranten Zellen durch Kultivierung auf einem Herbizid-haltigen Nährmedium in Gegenwart eines Safeners, dadurch gekennzeichnet, daß a) Kallus- oder Zellsuspensionskulturen unter Beibehaltung ihrer embryogenen und morphogenen Kompetenz selektioniert werden, b) die unter a) erhaltenen Kulturen auf einem Herbizid-haltigen Nährmedium kultiviert und selektioniert werden und c) aus den unter b) erhaltenen Kulturen intakte Pflanzen regeneriert werden.
9. A process for the production of herbicide-tolerant cells by cultivation on a herbicide-containing nutrient medium in the presence of a safener, characterized in that a) callus or cell suspension cultures are selected while maintaining their embryogenic and morphogenic competence, b) those obtained under a) Cultures are cultivated on a herbicide-containing nutrient medium and selected and c) intact plants are regenerated from the cultures obtained under b).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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AU41436/99A AU4143699A (en) | 1998-05-14 | 1999-05-14 | Sulfonylurea-tolerant sugar beet mutants |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19821614A DE19821614A1 (en) | 1998-05-14 | 1998-05-14 | Sugar beet mutants which are tolerant to sulfonylurea herbicides |
DE19821614.9 | 1998-05-14 |
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WO1999057965A1 true WO1999057965A1 (en) | 1999-11-18 |
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PCT/EP1999/003348 WO1999057965A1 (en) | 1998-05-14 | 1999-05-14 | Sulfonylurea-tolerant sugar beet mutants |
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AU (1) | AU4143699A (en) |
DE (1) | DE19821614A1 (en) |
WO (1) | WO1999057965A1 (en) |
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