WO1999057965A1 - Sulfonylurea-tolerant sugar beet mutants - Google Patents

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

Sulphonylurea-tolerant sugar beet mutants

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.

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.

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):

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 describes sulfonylurea- and imidazolinone-tolerant plants,

ßtSl ibUNGSKÜPIE which have been obtained by selection processes and have, inter alia, a tolerance to chlorosulfuron, bensulfuron, chlorimuron, thifensulfuron and sulfometuron.

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.

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.

However, 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) compounds of the formula (I) and their inorganic or organic salts,

wherein

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, - ^) -

Alkoxy, (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

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

A-4 A-5 A-6 A-7

A-8 A-9 A-10

wherein

XO, S, S (O) or S0 ₂ ;

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;

A2) compounds of the general formula II and their inorganic or organic salts, R ² -

NRR ⁵

wherein

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;

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

II II or ||

- C - T - R ⁹ , -C - NR ¹⁰ R ¹¹ -C - N (R ¹² ) ₂ , in which

W is an oxygen or sulfur atom (O or S);

T 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 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

(C ₃ -C ₄ ) alkynyl; A is a residue of the formula

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,

Are (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

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

wherein Ri H, halogen, (C ₁ -C ₄ ) alkyl, which is unsubstituted or one or more times by

Halogen is substituted, (C _r C ₄ ) alkoxy, (CC ₄ ) alkylthio;

R _{2 is} H or methyl;

R _{3 is} methyl or methoxy; A -N- (R ₄ ) R ₅ ;

R ₄ H, (C ₁ -C _β ) alkyl which is unsubstituted or one or more times by halogen,

(CC ₆ -) alkoxy, (C ₃ -C ₆ ) alkenyloxy, (C ₃ -C ₆ ) alkynyloxy or (CC ₆ ) -

Alkylthio is substituted;

H,

which is unsubstituted or one or more times by halogen,

(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 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,

(C ₁ -C ₄ ) haloalkyl, (CC ₄ ) alkoxy, (C ₁ -C ₄ haloalkoxy, (C ₃ -C ₆ ) alkenyloxy,

(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;

R 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

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, p.842);

A8) tribenuron (728, p.1230);

A9) flupyrsulfuron (348, p.586); A10) Nicosulfuron (519, p.877);

A11) Rimsulfuron (644, p.1095);

A12) Primisulfuron (589, p.997);

A13) prosulfuron (613, p.1041);

A14) Sulfosulfuron (668, p.1130); A15) oxasulfuron (542, p.911);

A16) ethametsulfuron (280, p.475);

A17) Imazosulfuron (416, p.703) and

A18) Compounds of the formula V. as disclosed in EP-A-0496701:

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.

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.

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.

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.

In 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

Carbohydrates or nitrogen-containing compounds (e.g. amino acid content, proteins).

In addition, 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. 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.

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

A1) Connections of the above general formula I,

A2) Connections of the above general formula II,

A3) Connections of the above general formula III, A4) amidosulfuron (21, p.37),

A5) ethoxysulfuron (287, p.488),

A6) triasulfuron (723, p.1222),

A7) Metsulfuron (498, p.842),

A8) Tribenuron (728, p.1230), A9) Flupyrsulfuron (348, p.586),

A10) Nicosulfuron (519, p.877),

A11) Rimsulfuron (644, p.1095)

A12) Primisulfuron (589, p.997)

A13) prosulfuron (613, p.1041) A14) sulfosulfuron (668, p.1130)

A15) oxasulfuron (542, p.911);

A16) ethametsulfuron (280, p.475);

A17) Imazosulfuron (416, p.703) and

A18) Compounds of the formula V. as disclosed in EP-A-0496701: Formula V:

are tolerant and which are preferably promoted in their growth by one or more sulfonylureas selected from group A consisting of A1 to A18.

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.

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

Metabolic processes in connection with metabolite flows) results.

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.

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.

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.

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.

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.

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-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-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-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-chloro-8-quinolinoxy) -acetic acid allyl ester, (5-chloro-8-quinolinoxy) -acetic acid-2- (2-propylidene-iminoxy) -1- ethyl ester,

(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) .

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).

In particular, 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).

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.

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) 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) 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) 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.

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.

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.

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.

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.

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.

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.

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.

The term "sugar beet culture according to the invention" generally includes

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.

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.

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.

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).

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.

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,

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.

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.

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.

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.

When 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

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 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.

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.

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.

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.

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.

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. 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.

In addition, the active ingredient formulations mentioned may contain the usual adhesive, wetting, dispersing, emulsifying, penetrating,

Preservatives, antifreeze and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH value and viscosity influencing means.

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).

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.

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.

The 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

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.

Table 1 MS medium mg / L

MgSO ₄ ^* 7H ₂ 0 370

CaCI ₂ * 2H ₂ 0 440

KN0 ₃ 1900

(NH ₄ ) ₂ S0 ₄ -

NH ₄ N0 ₃ 1650

KH ₂ P0 ₄ 170

MnS0 ₄ 22.3

KJ 0.86

CoCI ₂ * 6H ₂ 0 0.025

ZnS0 ₄ * 7H _s O 8.6

CuS0 ₄ * 5H ₂ 0 0.025

H ₃ B0 ₃ 6.2

Na ₂ Mo0 ₄ * 2H ₂ 0 0.25

EDTA 37.3

FeS0 ₄ * 7H ₂ 0 27.3

Thiamine * Hcl 0.5 Continued Table 1 MS medium

Nicotinic acid 0.2

Cyanocobalamin 0.1

Pyridoxine 0.2 p-aminobenzoic acid 0.05

Ca panthothenate 0.1

Biotin 0.1

Folic acid 0.05

Nicotinic acid 0.2

Choline HCI 0.1

Riboflavin 0.05

Inositol 100

Sucrose 30000

Agar 7000

Naphtylacetic acid 0.1

Benzylaminopurine 1,0

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.

Cell 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

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.

Example 3: Selection of herbicide-resistant callus cultures

It is first determined at which herbicide concentration in the medium 95 to 99% of the calli die off.

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.

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.

Example 4: Plant regeneration

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.

Example 5: Selection of sulfonylurea tolerant sugar beet mutants in the presence of herbicide and safener.

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.

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.

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) none

2) 1 x 10- ° M SH 3) 2.5 x 10 ^"6 M SH

4) 1 x 10- ° M SH + 1 x 10 ^'5 M DIC

5) 2.5 x 10 ^ M SH + 1 x 10- ° M DIC

After 6 weeks, the number of cell colonies was determined by counting. The result is shown in Table 2.

Table 2: Number of cell colonies (number / 10 petri dishes)

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.

Biological examples

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.

Example 7: Herbicidal action on harmful plants in crops of sugar beet mutants

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.

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.

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

Claims:

1. sulfonylurea-tolerant sugar beet mutant, its seed or

Propagation material or their cells, characterized in that they are tolerant to one or more sulfonylureas selected from the group

Group A consisting of

A1) Compounds of formula (I) and their inorganic or organic

Salts,

wherein

Q oxygen, sulfur or -N (R ⁴ ) -,

Y 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

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-

10

A-4 A-5 A-6 A-7

A-8 A-9 A-10

wherein XO, S, S (0) or S0 ₂ ;

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 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;

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,

R ² -

NRR ⁵

wherein

R ¹ CO-QR ⁸ ,

R ² and R ³ independently of one another are H or (CC ₄ ) alkyl,

R ⁴ H, (CC ₄ ) aikyl, hydroxy or (CC ₄ ) alkoxy,

R 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 or

- C - T - R ⁹ -C - NR ¹⁰ R ¹¹ or -CMN / (DR1 ¹ 2 ² \)

mean what

W is an oxygen or sulfur atom (O or S),

TO 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

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,

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 -

C ₄ ) alkynyl, A is a radical of the formula

wherein 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

R ¹³ H, (C ^ C alkyl that is unsubstituted or substituted by one or more

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,

wherein

Ri H, halogen, (CC ₄ ) alkyl, which is unsubstituted or one or more times

Halogen is substituted, (CC ₄ ) alkoxy, (C ₁ -C ₄ ) alkylthio;

R _{2 is} H or methyl;

R _{3 is} methyl or methoxy; A -N- (R ₄ ) R ₅ ;

R ₄ H,

which is unsubstituted or one or more times by halogen,

(C _r C ₆ -) alkoxy, (C ₃ -C ₆ ) alkenyloxy, (C ₃ -C ₆ ) alkynyloxy or (CC ₆ ) -

Alkylthio is substituted;

R, H, (C ^ C alkyl, which is unsubstituted or one or more times by halogen,

(CC _β ) alkoxy, (C ₃ -C ₆ ) alkenyloxy, (C ₃ -C ₆ ) alkynyloxy or (CC ₆ ) alklythio, or C (0) R ₆ ;

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 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,

(C ₁ -C ₄ ) haloalkyl, (C _r C ₄ ) alkoxy, (CC ₄ ) haloalkoxy, (C ₃ -C ₆ ) alkenyloxy,

(C ₃ -C _β ) alkynyloxy, nitro, cyano, COOR ₈ , NR ₁₀ R _{11 t} C (0) NR ₁₂ R ₁₃ , XR _S ,

S0 ₂ NR _1β R ₁₇ or are substituted by X ₂ R ₁₈ or OR ₇ ;

Rr (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 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 ;

R ₈ H,

(C ₃ -C ₆ ) alkenyl, (C ₃ -C ₆ ) alkynyl or oxetan-3-yl;

R 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 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 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

R ₁₄ H, (C _r C ₄ ) alkyl, (C ₃ -C ₆ ) alkenyl or (C ₃ -C ₆ ) alkynyl;

R ₅ and R ^ each independently of one another (CC ₄ ) alkyl or (C 1 -C ₄ ) haloalkyl;

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., and X ₃ each independently of one another S, SO or S0 ₂ ;

X ₂ and X _{4 are} each independently O or S;

X _{5 represents} O or NR _M ;

A4) amidosulfuron; A5) ethoxysulfuron;

A6) triasulfuron;

A7) metsulfuron; A8) tribenuron;

A9) flupyrsulfuron;

A10) nicosulfuron;

A11) rimsulfuron;

A12) primisulfuron;

A13) prosulfuron;

A14) sulfosulfuron;

A15) oxasulfuron;

A16) ethametsulfuron;

A17) imazosulfuron and

A18) compounds of the formula V:

Formula V:

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. 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. Use of sugar beet mutants obtainable by a process according to claim 3 in agriculture, as feed or for sugar production.

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. 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) 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) a herbicide from the class of the hydroxyphenyl pyruvate dioxygenase (HPPDO) inhibitors, e.g. the triketones, preferably isoxaflutole, isoxachlorozole or sulcotrione;

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. 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. 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. 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).