The present invention relates to novel herbicidally active plant-growth-regulating sulfonylureas, to processes for their preparation, to compositions containing them as active ingredients, and to their use for controlling weeds, especially selectively in crops of useful plants, or for regulating and inhibiting the growth of plants.

Urea compounds, triazine compounds and pyrimidine compounds which have herbicidal activity are generally known. Such compounds are described, for example, in EP-A-0007 687, 0030 138, 0073 562, 0 126711 and US-A-4618 363.

Novel sulfonylureas which have herbicidal and plant-growth-regulating properties have now been found.

The present invention therefore relates to compounds of the formula

in which

Q is a radical of the formula A or B

or

B

R is hydrogen or methyl,

X is C ₁ -Calkyl, C ₁ -Calkoxy, C ₁ -Chaloalkoxy, C ₁ -Chaloalkyl, Cx-C^haloalkylthio,

C ₁ -Callgrlthio, halogen, C^-Csalkoxyalkyl, C ₂ -C ₅ alkoxyalkoxy, C ₁ -C ₃ alkylamino or di^-Csalky^amino,

Yis C _r C ₄ alkl, C ₁ -C ₄ alkoxy, C _r C ₄ haloalkoxy, C _r C ₄ haloalkylthio, C ₁ -C ₄ all^lthio,

C^-Csalkoxyalkyl, Cj-Csalkoxyalkoxy, C ₂ -C- ₅ --lkylthioalkyl or cyclopropyl,

Eis-CH=or-N=,

R _al is hydrogen, halogen, -(Z^-Rx, nitro, -NR ₂ R ₃ , -C≡C-R ₄ , -O-CHR ₅ -C-≡C-R ₄ or

-COOR ₆ ,

R _a2 is hydrogen, fluorine, chlorine or methyl,

R is hydrogen, fluorine, chlorine, methyl or methoxy,

ZisO,S,SOorSO ₂ , n is 0 or 1,

R _x is C ₁ -C ₄ alkyl _I C-C ₄ alkyi which is substituted by 1 to 4 halogen atoms, C C ₃ alkoxy or

C ₁ -C ₃ alkylthio, or is C ₂ -Calkenyl, or C ₂ -Calkenyl which is substituted by 1 to 4 halogen atoms,

R ₂ is hydrogen or Cj^alkyl,

R ₃ is hydrogen, or C _r C ₃ alkoxy,

R ₄ is hydrogen or C _r C ₄ alkyl,

R ₅ is hydrogen or methyl and

R ₆ is Cx- alkyl or C ₃ -C ₆ cycloalkyl, and salts of these compounds, wherein the 2-position in the radical of the formula A is occupied by R _al or by the oxetanyloxy substituent and, if R _aJ is -COOR ₆ , this substituent occupies the 2-position in the radical of the formula A, and wherein E is -CH= if X is halogen or X or Y are -OCHF ₂ or -SCHF ₂ .

In preferred compounds of the formula I, Q is a radical of the formula A in which R _al is hydrogen, chlorine, -CO ₂ CH ₃ , -CO^Hs, -CH ₂ CH ₂ CF ₃ , -CH=CH-CF ₂ -CH ₃ or -C---CH und R _j g is hydrogen or methyl. R _aJ and R^ are preferably hydrogen. If Q is such a radical of the formula A, then R is preferably hydrogen, X is preferably methyl, methoxy, chlorine, -OCHF ₂ or -OCH ₂ CF ₃ and Y is preferably methyl, methoxy, chlorine, -OCHF ₂ or -N(CH ₃ ) ₂ .

In another group of particularly suitable compounds of the formula I, Q is a radical of the formula B in which R _b is hydrogen. In this case, R is preferably hydrogen, X is preferably methyl, methoxy, ethoxy, -OCHF ₂ or -OCH ₂ CF ₃ and Y is preferably methyl, methoxy, chlorine, -N(CH ₃ ) ₂ or cyclopropyl. Particularly preferably, X and Y independently of one another are methyl or methoxy.

In another group of particularly effective compounds of the formula I, R is hydrogen.

Another group of preferred compounds of the formula I contain, as substituent Q, a radical of the formula

in which R is as defined above. Preferred compounds amongst these are those in which R _b is hydrogen.

The compound of the formula

is particularly important.

In the above definitions, halogen is to be understood as meaning fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine.

The alkyl groups in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl or tert-butyl. The alkyl groups as, or in the, substituents preferably have 1-3 carbon atoms.

Alkenyl is to be understood as meaning straight-chain or branched alkenyl, for example vinyl, allyl, methallyl, 1-methylvinyl or but-2-en-l-yl. Preferred alkenyl radicals are those having a chain length of 2 to 4 carbon atoms.

Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fIuoroethyl, 2-chlonoethyl, 2,2,2-trichloroethyl and 3,3,3-trifluoropropyl; preferably trichloromethyl, difluorochloromethyl, trifluoromethyl and dichlorofluoromethyl.

Alkoxy is, for example, methoxy, ethoxy, propyloxy, i-propyloxy, n-butyloxy, iso-butyloxy, sec-butyioxy and tert-butyloxy; preferably methoxy and ethoxy.

Haloalkoxy is, for example, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2-difluoroethoxy; preferably difluoromethoxy, 2-chloroethoxy, trifluoromethoxy and

3,3,3-trifluoropropyloxy.

Alkyl thio is, for example, methylthio, ethyl thio, propylthio, isopropylthio, n-butylthio, iso-butylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio.

Examples of alkoxyalkoxy are: methoxymethoxy, methoxyethoxy, methoxypropyloxy, ethoxymethoxy, ethoxyethoxy and propyloxymethoxy.

Alkylamino is, for example, methylamino, ethylamino, n-propylamino or iso-propylamino. Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino or n-propylmethylamino.

The invention also embraces the salts which the compounds of the formula I can form with amines, alkali metal bases or alkaline earth metal bases or quaternary ammonium bases.

Preferred alkali metal hydroxides and alkaline earth metal hydroxides as salt-forming substances are lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide or calcium hydroxide, but in particular sodium hydroxide or potassium hydroxide.

Examples of amines which are suitable for salt formation are primary, secondary and tertiary aliphatic and aromatic amines such as methylamine, ethylamine, n-propylamine, iso-propylamine, the four isomeric butylamine radicals, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, di-iso-propylamine, di-n-butylamine, di-n-amylamine, di-iso-amylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, iso-propanolamine, N,N-diethylethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, di-butenyl-2-amine, n-hexenyl-2-amine, propylenediamine, diethanolamine, trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propylamine, tri-n-butylamine, tri-iso-butylamine, tri-sec-butylamine, tri-n-amylamine; heterocyclic amines, for example

pyridine, quinoline, ϊso-quinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o,m,p-toluidines, phenylenediamines, benzidines, naphthylamines and o,m,p-chloroanilines; but in particular ethyl-, propyl-, diethyl- or triethylamine, but especially iso-propylamine and diethanolamine.

As a rule, examples of quaternary ammonium bases are the cations of haloammonium salts, for example the tetramethylammonium cation, the trimethylbenzylammonium cation, the triethylbenzylammonium cation, the tetraethylammonium cation, the trimethylethylammonium cation, but also the ammonium cation.

The compounds of the formula I according to the invention can be prepared for example by reacting suitable sulfonamides with corresponding pyrimidine or triazine derivatives. Thus, the compound of the formula

Q-SO ₂ -NH ₂ π

can be reacted with a compound of the formula

or

to give the corresponding end products. It is also possible to convert substituted sulfonamides, f

example that of the formula

Q-SO ₂ -NH-COOR _c V

with a compound of the formula

into a compound of the formula I according to the invention.

In formulae II to VI, Q, R, X, Y and E are as defined above; R _< . is phenyl which can be substituted.

The reactions which give compounds of the formula I are advantageously carried out in aprotic, inert organic solvents. Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as acetonitrile or propionitrile, amides such as dimethylformamide, diethylformamide, or N-methylpyrrolidinone. The reaction temperatures are preferably between -20° and +120°C.

As a rule, the reactions are slightly exothermic and can be carried out at room temperature. To shorten the reaction time or else to start up the reaction, it is expedient to heat the reaction mixture briefly up to its boiling point. The reaction times can also be shortened by adding a few drops of base as reaction catalyst. Suitable bases are, in particular, tertiary amines such as trimethylamine, triethylamine, quinuclidine, l,4-diazabicyclo-(2.2.2)-octane, l,5-diazabicyclo(4.3.0)non-5-ene or l,5-diazabicyclo(5.4.0)undec-7-ene. Alternatively, inorganic bases such as hydrides, such as sodium hydride or calcium hydride, hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate or hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen

carbonate, can also be used as bases.

The end products of the formula I can be isolated by concentration and/or evaporation of the solvent and purified by recrystallisation or trituration of the solid residue in solvents in which they are not freely soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.

Thephenylsulfonamides of the formulae

and

are novel compounds which were developed and prepared specifically as intermediates for the preparation of the active ingredients of the formula I. They are therefore also part of the present invention.

Compounds of the formula VII can be prepared for example by the following methods:

a) reaction of a compound of the formula

with a compound of the formula

b) reaction of a compound of the formula

with a compound of the formula

Reactions of this type are described for example in US-A-4523 944.

A further variant which can be used for the preparation of the abovementioned intermediates is proposed in Ace. Chem. Res. 12, 146 (1979) and Synthesis 312 (1983) and 253 (1985) and consists essentially of the conversion of a compound of the formula

VII into another derivative:

c) reaction of the compound of the formula

with a compound of the formula A-B in the presence of a Pd catalyst to give the compound of the formula

EP-A-336587 describes a further preparation method:

d) reaction of the compound of the formula

in a two-stage process with chlorine and ammonia to give the compound of the formula

R a2

For example, the following processes are suitable for the preparation of the compounds of the formula VIII:

e) reaction of the compound of the formula

with a compound of the formula X and

f) reaction of the compound of the formula

with a compound of the formula XII.

Reactions of this type are described, in particular, in US-A-4 579583 and PCT/EP92/00555.

Other processes for the preparation of sulfonylureas of the claimed type are illustrated in

US-A-4537 618 and 5041 603 as well as EP-B-120 814.

In the abovementioned formulae, the substituents R _al , R^ and R _b are as defined above. R^ is methyl, phenyl or substituted phenyl, R _x is bromine or iodine, R' _al is -Cr^CT^, -C≡C-R or -COOR ₆ , in which T _x is hydrogen or C _r C ₅ alkyl, T ₂ is hydrogen, C _r C ₅ alkyl or halogen and T ₃ is hydrogen or Cx-Csalkyl which is optionally substituted by halogen, R _y is i-propyl or benzyl and HAL is halogen. A-B is a compound of the formula HT ₁ C=CT ₂ T ₃ or HC---CR ₄ or a combination of CO and R ₆ OH, in which T _lt T ₂ , T ₃ , R and Rg have the abovementioned meanings.

Compounds of the formulae X and XII are known for example from J. Org. Chem.48, 2953 (1983) and Acta Chem. Scand. 28, 701 1974). Compounds of the formulae IX and XI can be prepared by the processes described in EP-A- 205 348, 216504, 336587 and US-A-4523944, 4618 363 and 4981 509. The preparation processes in accordance with US-A-4579583 and of Swiss Patent Application 895/91-6 are suitable for the compounds of the formulae XVE and XVm.

As a rule, the active ingredients of the formula I are applied successfully at application rates of 0.001 to 2 kg/ha, in particular 0.005 to 1 kg/ha. The dosage rate required for the desired action can be determined by experiments. It depends on the type of action, the development stage of the crop plant and of the weed and on the application (location, time, method) and, due to these parameters, can vary within wide ranges.

The compounds of the formula I are distinguished by growth-inhibiting and herbicidal properties which make them outstandingly suitable for use in crops of useful plants, in particular in cereals, cotton, soya beans, oilseed rape, maize and rice, their use in soya bean crops and cereals being especially preferred. Weeds in soya bean crops are preferably controlled postemergence. The compounds of the formula I are particularly distinguished by their good degradability.

The invention also relates to herbicidal and plant-growth-regulating compositions which comprise a novel active ingredient of the formula I, and to methods for inhibiting the growth of plants.

Plant growth regulators are substances which cause agronomically desirable biochemical and/or physiological and/or morphological modifications in/on the plant.

The active ingredients comprised in the compositions according to the invention affect plant growth in many ways, depending on the point in time of application, the dosage rate, the type of application and the prevailing environment. For example, plant growth regulators of the formula I can inhibit the vegetative growth of plants. This type of action is of interest on lawns, in the production of ornamentals, in fruit plantations, on verges, on sportsgrounds and industrial terrain, but also in the targeted inhibition of secondary shoots, such as in tobacco. In arable farming, inhibition of the vegetative growth in cereals by strengthening the stems results in reduced lodging, and similar agronomic effects are achieved in oilseed rape, sunflowers, maize and other crop plants. Furthermore, inhibition of the vegetative growth means that the number of plants per area can be increased. Another field in which growth inhibitors can be applied is the selective control of ground-cover plants in plantations or crops with plenty of space between the rows, by powerful growth inhibition without destroying these cover crops, so that competition with the main crop is eliminated, but the agronomically positive effects such as prevention of erosion, nitrogen fixation and loosening of the soil, are retained.

A method for inhibiting plant growth is understood as meaning controlling the natural development of the plant without altering the life cycle of the plant, which is determined by its genetic make-up, in the sense of a mutation. The method of growth regulation is applied at a particular point in time of the development of the plant, which is to be determined in the particular case. The active ingredients of the formula I can be applied before or after emergence of the plants, for example already to the seeds or seedlings, to roots, tubers, stalks, leaves, flowers or other parts of the plant. This can be effected, for example, by applying the active ingredient, as pure active ingredient or in the form of a composition, to the plants and/or by treating the nutrient substrate of the plant (soil).

Various methods and techniques are suitable for using the compounds of the formula I or compositions containing them for regulating plant growth, for example the following:

i) Seed dressing a) Dressing of the seeds with an active ingredient formulated as wettable powder by shaking in a container until the seed surface is uniformly covered (dry seed dressing). Up to 4 g of active ingredient of the formula I are used per kg of seeds (up to 8.0 g of wettable powder in the case of a 50 % formulation).

b) Dressing of the seeds with an emulsion concentrate of the active ingredient or with an aqueous solution of the active ingredient of the formula I formulated as a wettable powder, using method a) (wet seed dressing).

c) Dressing by immersing the seeds in a liquor containing up to 1000 ppm of active ingredient of the formula I for 1 to 72 hours, if desired followed by drying the seeds (seed soaking).

Naturally, seed dressing or treatment of the germinated seedling are the preferred application methods since the treatment with active ingredient is directed entirely at the target crop. As a rule, 0.001 g to 4.0 g of active ingredient are used per kg of seed, but it is possible to deviate from the limit concentrations given in both directions, depending on the method chosen, which also makes possible the addition of other active ingredients or micronutrients (repeated seed treatment).

ii) Controlled release of active ingredient

The dissolved active ingredient is applied to mineral granule carriers or polymerised granules (urea/formaldehyde) and allowed to dry. If desired, a coating can be applied

(coated granules), which permits slow release of the active ingredient over a certain period.

The compounds of the formula I are employed in unaltered form, as obtained from synthesis, or, preferably, together with the auxiliaries conventionally used in the art of formulation, and they are therefore processed in a known manner to give, for example, emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules and also encapsulations, for example in polymeric substances. The application methods such as spraying, atomising, dusting, wetting, scattering or pouring, as well as the type of the compositions are selected to suit the intended aims and the prevailing circumstances.

The formulations, i.e. the compositions, preparations or combinations comprising the active ingredient of the formula I and, if desired, one or more solid or liquid additives, are prepared in a known manner, for example by intimately mixing and/or grinding the active ingredients with extenders, for example solvents, solid carriers and, if desired, surface-active compounds (surfactants).

The following are possible as solvents: aromatic hydrocarbons, in particular the fractions Cg to C ₁ , such as mixtures of alkylbenzenes, for example xylene mixtures or alkylated naphthalenes; aliphatic and cycloahphatic hydrocarbons such as paraffins, cyclohexane or tetrahydronaphthalene; alcohols such as ethanol, propanol or butanol; glycols as well as their ethers and esters, such as propylene glycol or dipropylene glycol ether, ketones such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents such as N-methyl-2-pyrro one, dimethyl sulfoxide or water; vegetable oils and esters thereof, such as rapeseed oil, castor oil or soya oil; silicone oils may also be suitable.

Solid carriers which are used, for example for dusts and dispersible powders, are, as a rule, natural ground minerals such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve the physical properties, it is also possible to add highly-disperse silica or highly-disperse absorptive polymers. Possible paniculate, adsorptive carriers for granules are either porous types, for example pumice, brick grit, sepiolite or bentonite, or non-sorptive caπier materials, such as calcite or sand. Moreover, a large number of pregranulated materials of inorganic or organic nature can be used such as, in particular, dolomite or comminuted plant residues.

Suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties, depending on the nature of the active ingredient of the formula I to be formulated. Surfactants are also to be understood as meaning mixtures of surfactants.

Anionic surfactants which are suitable can be either so-called water-soluble soaps or water-soluble synthetic surface-active compounds.

Suitable soaps which may be mentioned are the alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts of higher fatty acids (C ₁₀ -C ₂₂ ), such as, for example, the sodium salts or potassium salts of oleic or stearic acid, or of natural mixtures of fatty acids which can be obtained, for example, from coconut oil or tallow oil. Mention must also be made of the fatty acid methyltaurinates.

However, so-called synthetic surfactants are used more frequently, in particular fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylarylsulf onates .

The fatty alcohol sulfonates or fatty alcohol sulfates are, as a rule, in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts, and have an alkyl radical having 8 to 22 carbon atoms, alkyl also including the alkyl moiety of acyl radicals, for example the sodium salt or calcium salt of ligninsulfonic acid, of the dodecylsulfiiric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids. This group also includes the salts of the sulfuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonyl groups and one fatty acid radical having 8-22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonic acid/formaldehyde condensation product.

Other suitable compounds are the corresponding phosphates, such as the salts of the phosphoric ester of p-nonylphenol/(4-14)-ethylene oxide adduct, orphospholipids.

Suitable non-ionic surfactants are mainly polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.

Other non-ionic surfactants which are suitable are the water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol which have 1 to 10 carbon atoms in the alkyl chain and which contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. The abovementioned compounds customarily contain 1 to 5 ethylene glycol units per propylene glycol unit.

Examples of non-ionic surfactants which may be mentioned are nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.

Other suitable substances are fatty acid esters of polyoxyethylenesorbitan, such as polyoxyethylenesorbitan trioleate.

The canonic surfactants are mainly quaternary ammonium salts which contain at least one

alkyl radical having 8 to 22 carbon atoms as N substituents and which have lower halogenated or free alkyl, benzyl or lower hydroxyalkyl radicals as further substituents. The salts are preferably in the form of halides, methylsulfates or ethylsulfates, for example stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants conventionally used in the art of formulation are described, inter alia, in the following publications:

"Mc Cutcheon's Detergents and Emulsifiers Annual", Mc Publishing Corp.,

Glen Rock, New Jersey, 1988.

M. and J. Ash, "Encyclopedia of Surfactants", Vol. I-IH.Chemical Publishing Co.,

New York, 1980-1981.

Dr. Helmut Stache "Tensid-Taschenbuch" [Surfactant Guide], Carl Hanser Verlag,

Munich/Vienna, 1981.

As a rule, the preparations comprise 0.1 to 99 %, in particular 0.1 to 95 %, of active ingredient of the formula 1, 1 to 99 % of the solid or liquid additive and 0 to 25 %, in particular 0.1 to 25 %, of a surfactant.

While concentrated compositions are more preferred as commercial goods, the end user, as a rule, uses dilute compositions.

The compositions can also comprise further additions such as stabilisers, for example epoxidised or unepoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soya oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers as well as fertilisers or other active ingredients for achieving specific effects.

Preferred formulations have in particular the following compositions:

{% = per cent by weight)

Emulsifiable concentrates:

Active ingredient: 1 to 20 , preferably 5 to 10 %

Surface-active agent: 5 to 30 %, preferably 10 to 20 %

Liquid carrier: 15 to 94 , preferably 70 to 85 %

Dusts:

Active ingredient: 0.1 to 10 %, preferably 0.1 to 1 %

Solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %

Suspension concentrates: Active ingredient: 5 to 75 %, preferably 10 to 50 % Water 94 to 24 %, preferably 88 to 30 % Surface-active agent: 1 to 40 %, preferably 2 to 30 %

Wettable powders: Active ingredient: 0.5 to 90 %, preferably 1 to 80 % Surface-active agent: 0.5 to 20 %, preferably 1 to 15 % Solid carrier: 5 to 95 %, preferably 15 to 90 %

Granules: Active ingredient: 0.5 to 30 , preferably 3 to 15 % Solid carrier: 99.5 to 70 %, preferably 97 to 85 %

Preparation Examples:

Example 1: Preparation of 2-(oxetan-3-yloxy)phenylsulfonamide

A mixture of 28.8 g of 2-hydroxyphenylsulfonamide, 40.0 g of oxetan-3-yl 4-methylphenylsulfonate, 23.5 g of potassium carbonate and 100 ml of dimethylformamide is stirred for 24 hours at 100 to 105°C. 14.3 g of the title compound with a melting point of 180 to 182°C are obtained by pouring the mixture into water, neutralising it with hydrochloric acid (10 %) and extracting it with ethyl acetate and drying and concentrating the extract until it crystallises.

Example 2: Preparation of 2-(2-chloroethoxy)-5-hydroxyphenylsulfonamide

54 g of boron tribromide are added dropwise with ice-cooling at not more than 30°C to a solution of 11.4 g of 2-(2-chloroethoxy)-5-methoxyphenylsulfonamide in 500 ml of methylene chloride, and the mixture is stirred for 30 minutes. The reaction mixture is .poured into a mixture of 1000 ml of ice- water and 500 ml of methylene chloride and washed to neutrality using saturated sodium chloride solution, and the aqueous phase is

treated with 350 g of sodium chloride and extracted using ethyl acetate. The organic phase is washed again with saturated sodium chloride solution and subsequently dried over sodium sulfate. After evaporation and recrystallisation from chloroform hexane, 8.0 g of the title compound with a melting point of 146 to 147°C are obtained.

Example 3: Preparation of N-[2-(oxetan-3-yl-oxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl -pyrimid-2-yl)urea

A mixture of 2.0 g of 2-(oxetan-3-yl)phenylsulfonamide, 2.2 g of 4-methoxy-6-methylpyrimid-2-yl phenylcarbamate and 30 ml of absolute dioxane is treated dropwise at 20 to 25°C with a solution of 1.33 g of diazobicyclo[5.4.0]undec-7-ene(1.5-5) and 10 ml of absolute dioxane, and this is stirred for 2 hours at 20 to 25°C. 3.0 g of the title compound

with a melting point of 195 to 197°C are obtained by pouring the mixture into water, adding hydrochloric acid (10 %) dropwise until a pH of 5 is obtained, filtration with suction and washing with water.

Example 4: Preparation of 3-(oxetan-3-yloxy)pyridin-2-yl-sulfonamide

7 g of oxetan-3-ol are added dropwise at not more than 30°C to a suspension of sodium hydride (55.6 % in oil) in 115 ml of dimethylformamide. After the mixture has been stirred for 10 minutes, a solution of 12.33 g of 3-fluoropyridine-2-sulfonamide in 35 ml of dimethylformamide is added dropwise at 22 to 32°C in the course of 15 minutes, the suspension is stirred for 2 hours at 60°C, a further 1.4 g of oxetan-3-ol are added, and the mixture is then stirred at 60°C for another hour. This gives a viscous suspension which is diluted with 50 ml of acetonitrile. The suspension is treated with 15 ml of trifluoroacetic acid with cooling, stirred for 10 minutes at 10 to 15 °C and filtered, and the filtrate is concentrated. The residue is purified by chromatography over silica gel using ethyl

acetate/methanol (5:1), and 11.2 g of the title compound with a melting point of 178 to 181°C are obtained.

Example 5: Preparation of N-[(3-oxetan-3-yloxy)pyridin-2-ylsulfonyl]-N ^< -(4,6-dimethoxypyrimidin-2-yl)urea

3.47 g of N-(4,6-dimethoxypyrimidin-2-yl) phenylcarbamate and 1.96 ml of l,5-diazabicyclo[5.4.0]undec-5-ene are added to a solution of 2.76 g of 3-(oxetan-3-yloxy)pyridin-2-ylsulfonamide in 40 ml of acetonitrile, and the mixture is stirred for 90 minutes at room temperature. It is then concentrated, and the oily residue is triturated with 8 ml of hydrochloric acid (2 N) and water, filtered, washed with ether and water and dried.4.5 g of the title compound

with a melting point of 168 to 169°C are obtained.

The compounds of the formula (1) and the intermediates thereof which are listed in the tables below can be prepared analogously.

Table 1:

Table 1: Continuation

Table 2:

Table 3:

Formulation examples of active ingredients of the formula I (% = per cent by weight)

Fl. Wettable powders a) b) c)

Active ingredient according to

Tables 1-3

Sodium ligninsulfonate

Sodium lauryl sulfate

Sodium diisobutylnaphthalenesulfonate

Octylphenol polyethylene glycol ether

(7-8 moles of EO)

Highly-disperse silica

Kaolin

Sodium chloride - - 59.5 %

The active ingredient is mixed thoroughly with the additives and the mixture is ground thoroughly in a suitable mill. This gives wettable powders which can be diluted with water to give suspensions of any desired concentration.

F2. Water-dispersible granules a) b)

Active ingredient according to

Tables 1-3

Sodium dibutylnaphthalenesulfonate

Gum arabic

Sodium sulfate

Sodium ligninsulfonate

Kaolin

Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

F3. Dusts a) b)

Active ingredient according to

Tables 1-3 O.i % 1 %

Talc 99.9 % Kaolin - 99 %

Ready-for-use dusts are obtained by intimately mixing the carriers with the active ingredient.

F4. Extruder granules a) b) Active ingredient according to

Tables 1-3 10 % 1 %

Sodium ligninsulfonate 2 % 2 %

Carboxymethylcellulose 1 % 1 %

Kaolin 87 % 96 %

The active ingredient is mixed with the additives, and the mixture is ground and moistened with water. This mixture is extruded and subsequently dried in a stream of air.

F5. Coated granules

Active ingredient according to Tables 1-3 3 %

Polyethylene glycol (MW200) 3 %

Kaolin 94 %

In a mixer, the kaolin which has been moistened with polyethylene glycol is coated uniformly with the finely-ground active ingredient. Dust-free coated granules are obtained in this manner.

The finely ground active ingredient is mixed intimately with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.

F7. Salt solution

Active ingredient according to Tables 1-3 5 %

Isopropylamine 1 %

Octylphenol polyethylene glycol ether

(78 moles of EO) 3 %

Water 91 %

Biological Examples

Example Bl: Herbicidal action before emergence of the plants Plastic pots are filled with expanded vermiculite (density: 0.135 g cm ³ , water adsorption capacity: 0.5651/1). The non-adsorptive vermiculite is saturated with an aqueous active ingredient emulsion in deionised water which comprises the active ingredients at a concentration of 70 ppm, and seeds of the following plants arc then sown onto the surface: Nasturtium officinalis, Agrostis tenuis, Stellaria media and Digitaria sanguinalis. The test containers are then kept in a controlled-environment cabinet at a temperature of 20°C, an illumination of approx. 20 kLux and a relative atmospheric humidity of 70 %. During a germination phase, of 4 to 5 days, the pots are covered with translucent material to increase the local atmospheric humidity and watered with deionised water. After day 5, 0.5 % of a commercially available liquid fertiliser is added to the irrigation water. 12 days after sowing, the test is evaluated and the effect on the test plants is assessed using the following key:

123 3 3 3 3 144 3 3 3 3 145 3 3 3 3 201 2 2 2 2 202 2 2 2 2 205 2 2 2 2 206 2 2 2 2 207 3 3 3 3 208 3 3 2 2 209 2 3 2 2 211 3 3 2 2 212 3 3 2 2

Example B2: postemergence herbicidal action (contact herbicide) A number of monocotyledon and dicotyledon weeds were sprayed after emergence (in the 4- to 6-leaf stage) with an aqueous dispersion of active ingredient according to Example F6 at a dosage rate of 8-500 g of active ingredient per hectare, and the plants were kept at 24°-26°C and a relative atmospheric humidity of 45-60 %. The test is evaluated 15 days after the treatment.

After 3 weeks, the herbicidal action is assessed using a 9-step (1 = complete damage, 9 = no action) score key in comparison with an untreated control group. Score figures from 1 to 4 (in particular 1 to 3) suggest good to very good herbicidal action. Scare figures from 6 to 9 (in particular from 7 to 9) suggest a good tolerance (in particular in crop plants).

In this test, the compounds of the formula I show a powerful herbicidal action. Identical results are obtained when the compounds of the formula I are formulated according to Examples Fl to F5 and F7.