GB1573215A

GB1573215A - Ammonium and sulphonium salts useful for regulating plant growth

Info

Publication number: GB1573215A
Application number: GB9159/77A
Authority: GB
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 1976-03-05
Filing date: 1977-03-04
Publication date: 1980-08-20
Also published as: IL51374A; BE852173A; FR2342966A1; JPS52106807A; DE2609105A1; FR2342966B1; IL51374A0

Description

(54) AMMONIUM AND SULFONIUM SALTS USEFUL FOR REGULATING PLANT GROWTH (71) We, BASF AKTIENGESELLSHAFT, a German Joint Stock Company of 6700 Ludwigshafen, Federal Republic of Germany, do hereby declare the invention, for which we pray that a Patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: The present invention relates to new and valuable ammonium and sulfonium salts and processes for the manufacture thereof, to compositions for regulating plant growth containing these compounds as active ingredients, and to methods of regulating plant growth with these compounds.

It is known to use N,N,N-trimethyl-N-ss-chloroethylammonium chloride, i.e. chlorocholine chloride (CCC, German Published Application DAS 1,294,734), N,N-dimethylmorpholinium chloride (DMC, German Published Application DAS 1,642,215) and N,N-dimethylpiperidinium chloride (DPC, German Laid-Open Application DOS 2,207,575) as plant growth regulators.

We have now found that ammonium and sulfonium salts of the formula

where X denotes

Rl denotes methyl and R2 denotes isopropyl, cyclopentenyl or (3-chloroethyl, or R1 and R2 together denote -(CH2)s-, -(CH2)2-O-(CH2)2-, -CH2-CH=CH-CH2-NH- or -(CH2)3-S- CH2, and ye denotes the anion of an anionic surfactant selected from those classes herein after specified, have a better growth-regulating action than the prior art compounds mentioned above. They influence the growth of plant parts above and below the ground in different ways, but they do not, when used in the usual concentrations, cause any changes or damage resulting in the withering of the plant. Their action is different from that of a herbicidal active ingredient and a fertilizer.

The active ingredients of the formula given above have an effect on the physiology of plant growth and may be used for various purposes in connection with increasing yields, facilitating harvesting, and making for labor savings in mechanical cultivation. The different effects of these active ingredients depend in essence on the time of application, based on the development stage of the seed or plant, and on the concentrations employed.

By suitable treatment with the agents of the invention it is possible to hasten the ripening process in plants and to achieve fuller and more uniform maturity of fruit and other crops, which is of considerable economic importance in various fruits and other crops.

The new active ingredients promote vegetative plant growth, flowering and fruiting. In particular, the supporting tissue of the stem of treated plants is strengthened and the resistance to lodging increased, especially in cereals (barley, wheat, rye, oats). Itis also possible to control the blossom-time and number of blooms in numerous crop plants and ornamentals.

The extent and type of effect are dependent on various factors, especially the time of application, with reference to the development stage of the plant, and the concentration employed. However, these factors differ in turn from plant to plant and with regard to the effect desired. For instance, cereals will be preferably treated in the growth phase between tillering and elongation; ornamentals in which it is desired to increase the bloom intensity and number of buds, before budding; the plants whose fruit is to be used or processed, an appropriate length of time before the harvest. The active ingredients are applied as solid or liquid agents not only to plant parts above the ground but also through the soil or onto the soil surface. It is preferred to apply the active ingredients to the plant parts above the ground, and solutions or aqueous dispersions are best suited for this. For treatment of the soil, dusts, granules and broadcasting agents are suitable in addition to solutions and dispersions.

The anionic surfactants from which the anion Y is selected are those in the following classes: alkane sulfonates, dodecylbenzene sulfonate, ether sulfonates, (i.e. compounds in which the hydrophobic organic radical contains an ether group), terminally sulfated alkoxylated fatty alcohols, terminally sulfated alkoxylated alkyl phenols, alkyl sulfinates, alkane phosphonates, alkane phosphinates, perfluoroalkyl sulfonates, perfluoroalkane carboxylic acids, a-olefin sulfonates,phosphoric acid mono-alkyl and dialyl esters, dialkyl sulfimides, oleic acid and sulfosuccinates. All these compounds have a hydrophilic anionic moiety, e.g. a sulfonate group or a carboxylate group, attached to a hydrophobic organic radical which, in the great majority of cases, contains at least 6 carbon atoms linked together in an aliphatic chain.

The compounds of the invention may be prepared by reaction of a compound of the formula

where X R1 and R2 have the above meanings and Hal denotes a halogen anion (e.g. Cle, Br9 or Id), with a compound of the formula HY and an alkali metal or alkaline earth metal hydroxide (e.g. NaOH, KOH, or MG(OH)2), preferably in stoichiometric amounts in the presence of a solvent, e.g. water, ethyl alcohol, ethyl acetate, ethylene chloride, n-hexane, cyclohexane, petroleum ether a hydrocarbon or a mineral oil fraction, at a temperatures of, e.g., 0 to 100"C.

The following are examples of the compounds of the invention: Formula Compound m.p. "C No.

5 Formula Compound No. m.p. C 10

C'c,iii "I 15 /7s-cs, ) 12Q5SO3e VII 210 7 l C H e VIII 20 .i(Cll3)3 | 12 Clr:'rs-/7 sore S03e IX 25 C:i3 C'S3 s 1 C12;I25,S03e x 30 1 X 7F 15 C00 XI 7 15 /m\ e XII 101 35 jC131"21C00d XII - 40 / / ; .,F13SOR XIII 40 u' - coo XIV 45 N0; 111 XV 45 ( / -nl7j0jb 7 p 0e XVI 50 50 /C;!-S\ 303 5 3 XVII 55 60 65 Examples 1 and 2, which follow, illustrate the manufacture of the compounds of the invention.

Example 1 452 parts by weight of N,N,N-trimethyl-N-ss-chloroethylammonium chloride (chlorocholine chloride (70 wt%, dissolved in water) and 600 parts by weight of ndodecylbenzenesulfonic acid are mixed in a stirred vessel. There are then added 800 parts by weight of water and 800 parts by weight of ethyl acetate. At 40 to 450C and while stirring, 180 parts by weight of a 50% aqueous caustic soda solution is added and the reaction mixture adjusted to a pH of 5 with it. The mixture is then stirred for 30 minutes at 40"C and the aqueous phase is subsequently separated.

The organic phase is dried with sodium sulfate and freed from the ethyl acetate solvent in - vacuo. There remains 900 parts of the compound, N,N,N-trimethyl-N-t3-chloroethyl- ammonium-n-dodecylbenzene sulfonate as an almost colorless viscous paste which solidifies to give a crystalline material; this material is dissolved in acetone and is precipitated in the form of colorless crystals by the addition of water to the solution; m.p.: 226 - 228"C (with discoloration).

Example 2 In a stirred apparatus, 150 parts of N,N-dimethylpiperidinium chloride is dissolved in 700 parts of absolute ethanol. While stirring, a solution of 327 parts of dodecylbenzenesulfonic acid in 200 parts of absolute ethanol is added. This mixture is refluxed. When the solution boils, a 10% ethanolic potassium hydroxide solution is added - the pH being continuously controlled by a pH meter -, until the pH is 7. The mixture is stirred for 1 hour at the boiling temperature under ethanol reflux, and then cooled to room temperature. The potassium chloride precipitate is filtered off, washed with a small amount of cold ethanol, and dried.

There is obtained 73.9 parts (theory: 75.56 parts) of potassium chloride. Complete concentration of the ethanol filtrate gives 431 parts (98% of theory) of N,N-dimethylpiperidiniumdodecylbenzene sulfonate, m.p.: 193 - 195"C.

The compositions according to the invention may be prepared in known manner by intimately mixing or grinding the active ingredients with liquid or solid carriers, if desired with the addition of dispersants or solvents inert to the active ingredients.

Active ingredient concentrates dispersible in water, i.e. wettable powders, pastes and emulsion concentrates, can be diluted with water to any desired concentration. They comprise active ingredient, carrier, optionally one or more additives to stabilize the active ingredient, surfactant, antifoam agent and optionally solvent. The active ingredient concentration in these agents is in general from 0.5 to 80% by weight. Application rates are in general from 0.1 to 10 kg of active ingredient per hectare.

Wettable powders and pastes may be obtained by mixing and grinding the active ingredients with conventional dispersants and conventional pulverulent carriers in suitable equipment until the product is homogeneous.

There may also be added to these mixtures active ingredient stabilizing additives and/or nonionic, anionic and cationic compounds which for instance improve the adherence of the active ingredients to plants and plant parts (spreader stickers) and/or guarantee superior wettability (wetting agents). The following are examples: mixture of olein and chalk, cellulose derivatives (e.g. methyl cellulose or carboxymethyl cellulose), hydroxyethylene glycol ethers of mono- and dialkylphenols, ligninsulfonic acid and alkali metal and alkaline earth metal salts thereof, polyethylene glycol ethers (Carbowaxes - CARBOWAX is a Registered Trade Mark), fatty alcohol polyglycol ethers, condensation products of ethylene oxide and for propylene oxide, polyvinylpyrrolidone, polyvinyl alcohols, ureaformaldehyde condensation products, and latex products. Generally speaking the active ingredients are mixed, ground, sieved and screened in such a manner that the particles in the wettable powders do not exceed 0.02 to 0.04 mm, and in the pastes 0.03 mm.

For the preparation of emulsion concentrates and pastes, dispersants as mentioned above, conventional organic solvents and water may be used.

The solvents should be practically odorless, non-phytotoxic and inert to the active ingredients.

The compositions according to the invention may be in the form of solutions. To this end, one or more of the active ingredients are dissolved in suitable organic solvents, mixtures of solvents or water. Suitable organic solvents are aliphatic and aromatic hydrocarbons, chlorinated derivatives thereof, alkyl naphthalenes, and mineral oils either individually or in admixture with one another. The active ingredient concentration in the solutions should generally be from 1 to 20% by weight.

The solid formulations such as dusts, broadcasting agents or granules contain solid carriers as described above and optionally additives for stabilizing the active ingredient.

The particle size of the carriers is advantageously up to about 0.1 mm for dusts, about 0.075 to 0.2 mm for broadcasting agents, and 0.2 mm and more for granules. The active ingredient concentration in these solid formulations is generally from 0.5 to 80% by weight.

All the active ingredient concentrates described above may also contain light stabilizers and antioxidants.

The growth-regulating effects of the compounds of the invention may be extended by adding one or more other growth regulators, or adapted to circumstances by mixing them with one or more fungicides and for fertilizers, especially urea. The compounds of the invention may be mixed with growth regulators, fungicides and fertilizers in any desired ratio; the conditions existing where the agents are to be used (fungus diseases, deficiency symptoms, etc) are decisive for the type of mixture.

Examples of growth regulators which can be mixed with the salts of the invention are: Phosphonic acid and derivatives thereof, such as 2-chloroethanephosphonic acid vinylphosphonic acid propylphosphonic acid phosphonomethylglycine bisphosphonomethylglycine and benzylphosphonic acid; ammonium and hydrazinium salts, such as chlorocholine chloride N,N-dimethylmorpholinium halide N,N-dimethyl-N-2-chloroethylhydrazinium halide N ,N-dimethyl-N-2-bromoethylhydrazinium halide N,N-dimethyl-N-isopropylhydrazinium halide N ,N-dimethyl-N-propen-(2)-yl hydrazinium halide N, N ,N-trimethyl-N-cyclopropanemethylammonium halide N,N-dimethylhexahydropyridazinium halide N ,N-dimethyltetrahydropyridazinium halide N,N,N-trimethyl-N-cyclopentenylammonium halide N,N-dimethyl-N-cyclopentenylhydrazinium halide and N,N,N-trimethyl-N-isopropylammonium halide; carboxylic acids and derivatives thereof, such as ss-indolylacetic acid a-naphthylacetic acid 4-chlorophenoxyacetic acid 2,4-dichlorophenoxyacetic acid 2-methyl-4-chlorophenoxyacetic acid 2,4,5-trichlorophenoxyacetic acid a-(2-methylphenoxy)-propionic acid a-2,4-dichlorophenoxy)-propionic acid a-(2-methyl-4-chlorophenoxy)-propionic acid a-(2,4.5-trichlorophenoxy)-propionic acid a-(2,4-dichlorophenoxy)-butyric acid a-(2-methyl-4-chlorophenoxy)-butyric acid and 2,4,5-triidobenzoic acid; sulfonium salts, such as S,S-dimethyl-S-2-chloroethylsulfonium halide S ,S-dimethyl-S-isopropylsulfonium halide S-methylthianium halide and 1-methyl-1,4-dithianium halide; and miscellaneous growth regulators, such as maleic hydrazide succinic acid-N,N-dimethyl hydrazide N-formyl-N-hydroxyglycine and salts thereof 9-hydroxyfluorene-9-carboxylic acid 7-chloro-9-hydroxyfluorene-9-carboxylic acid citric hydrazide and 5-chloro-2-thienylmethyl tri-n-butylphosphonium halide.

Examples of fungicides which can be combined with the compounds of the invention are: dithiocarbamates and derivatives thereof, e.g., ferric dimethyldithiocarbamate (ferbam) zinc dimethyldithiocarbamate (ziram) manganese ethylenebisdithiocarbamate (maneb) zinc ethylenebisdithiocarbamate (zineb) tetramethylthiuram disulfide (thiram) 3 ,5-dimethyl-1 ,3 ,5-2H-tetrahydrothiadiazine-2-thione nitrophenol derivatives, such as dinitro-(1-methylheptyl)-phenylcrotonate (dinocap) 2-sec-butyl-4,6-dinitrophenyl-3 ,5-dimethylacrylate (binapacryl) and 2-sec-butyl-4,6-dinitrophenylisopropylcarbonate; heterocyclic structures, such as N-trichloromethylthiotetrahydrophthalimide (captan) N-trichloromethylthiophthalimide (folpet) 2-heptadecyl-2-imidazoline (glsodin) 2 .4-dichloro-6- (o-chloroanilino)-s-triazine diethylphthalimidophosphorothioate 5-amino-1-[bis-(dimethylamino)-phosphynyl]-3-phenyl-1,2,4-triazole 5-ethoxy-3-trichloromethyl-1 ,2,4-thiadiazole 2,3-dicyano-1,4-dithiaanthraquinone (dithianon) 2-thio-1 ,3-dithio-[4,5-b]-quinoxaline (thioquinox) methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate 2-methoxycarbonylaminobenzimidazole 2-thiocyanomethylthiobenzothiazole (busan) 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone and pyridine-2-thiol-1-oxide; 8-hydroxyquinoline and its copper salt 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide 2,3-dihydro-5-carboxanilido-6-methyl-1 ,4-oxathiin 5,5-dimethyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine 2- [furyl-(2)]-benzimidazole piperazine-1 4-diyl-bis[1-(2 ,2,2-trichloroethyl)-formamide] 2-[thiazolyl-(4)]-benzimidazole 5-butyl-2-dimethylamino-4-hydroxy- 6-methylpyrimidine bis-(p-chlorophenyl)-3-pyrimidinemethanol 1 2-bis- 3-ethoxycarbonyl-2-thioureido)-benzene (thiophanate) and 1 ,2-bis-(3-methoxycarbonyl)-2-thioureido) 3-methoxycarbonyl)-2-thioureido)-benzene; and miscellaneous fungicides, such as dodecylguanidine acetate (dodine) 3-[2-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutarimide (cycloheximide) hexachlorobenzene 2,5-dimethylfuran-3-carboxylic acid anilide 2,5-dimethylfuran-3-carboxylic acid cyclohexylamide 2-methylbenzoic acid anilide 2-iodobenzoic acid anilide 2,3-dihydro-6-methyl-1 ,4-oxathiin-5-carboxylic acid anilide 2,3-dihydro-4,4-dioxy-1 ,4-oxathiin-5-carboxylic acid anilide 2,6-dimethyl-N-tridecylmorpholine and its salts 2,6-dimethyl-N-cyclododecylmorpholine and its salts 2,3-dichloro-1 ,4-naphthoquinone 1,4-dichloro-2,5-dimethoxybenzene p-dimethylaminobenzenediazosodium sulfonate 2-chloro-1-nitropropane N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide N-methyl-N-phenyl-(fluorodichloromethylthio)-N'-methyl sulfamide polychloro nitrobenzenes, such as pentachloronitrobenzene, methyl isothiocyanate, fungicidal robenzenes, such as pentachloronitrobenzene, methyl isothiocyanate, fungicidal antibiotics such as griseofulvin and kasugamycin, tetrafluorodichloroacetone, 1- - phenylthio semi-carbazide, Bordeaux mixture, nickel-containing compounds and sulfur; manganese-zinc ethylenediamine-bis-dithiocarbamate zinc- (N,N'-propylene-1 ,2-bis-dithiocarbamate) ammonia complex of zinc-(N,N'-ethylene-bis-dithiocarbamate) and N,N'-polyethylene-bis-thiocarbamoyl disulfide ammonia complex of zinc-(N,N'-propylene-bis-dithiocarbamate) and N,N' polypropylene-bis-thiocarbamoyl disulfide.

The following Examples 3 to 9 and 19 to 23 illustrate the effectiveness of the compounds of the invention as plant growth regulators, and Examples 10 to 18 illustrate compositions according to the invention.

Example 3 Spring barley of the "Villa" variety was grown in glass dishes filled with soil, and sprayed at a growth height of 10 cm with a 1 wt% aqueous solution of active ingredient I. For comparison purposes, CCC was employed analogously. Both active ingredients were used at application rates of 1.5, 3 and 6 kg/ha.

The plants treated with active ingredient I were much shorter than those treated with chlorocholine chloride (CCC), as will be seen from the following table: Active ingredient kg/ha Growth height cm relative untreated (control) - 31.5 100 CCC 1.5 30.5 98 CCC 3 28.5 92 CCC 6 28.0 90 I 1.5 26.0 84 I 3 26.0 84 I 6 25.0 81 Example 4 Spring barley of the "Villa" variety was grown in glass dishes filled with soil, and treated at a growth height of 10 cm with equimolar amounts of CCC and active ingredient I in aqueous solution.

The greater reduction in the stem length of the plants treated with I is apparent from the following table: Active ingredient Application rate in Growth height millimoles per dish cm relative untreated (control) - 31.5 100 CCC 1 x 10-2 29.5 95 CCC 2 X 10-2 28.5 92 CCC 4 x 10-2 28.5 92 I 1 X 10-2 23.0 74 I 2 X 10-2 23.0 74 I 4 x 10-2 20.0 65 Example 5 Spring wheat of the "Opal" variety was grown in glass dishes filled with soil and sprayed at a growth height of 10 cm with a 1 wt% aqueous solution of active ingredient I. CCC was used as comparison. Both active ingredients were employed at a rate of 1.5 and 3 kg/ha.

The action is apparent from the following table: Active ingredient kg/ha Growth height cm relative untreated (control) - 30.5 100 CCC 1.5 26.0 85 CCC 3 24.0 79 I 1.5 25.5 84 1 3 23.5 77 Example 6 Spring wheat of the "Opal" variety was grown in glass dishes filled with soil and treated at a growth height of 10 cm with equimolar amounts of CCC and I in aqueous solution.

The stronger action of I after 12 days is apparent from the following table: Active ingredient Application rate in Growth height millimoles per dish cm relative untreated (control) - 30.5 100 CCC 1 X 10-2 25.0 82 I 1 X 10-2 22.5 74 Example 7 Spring wheat was grown as described in Example 6 in glass dishes filled with soil and treated at a growth height of from 10 to 12 cm with a 1 wt% aqueous solution of the active ingredient N,N-dimethylmorpholinium chloride (DMC) and of active ingredient IV. The action was as follows: Active ingredient kg/ha Growth height cm relative untreated (control) - 29.5 100 DMC 1.5 27.0 92 DMC 6 26.0 88 IV 1.5 26.5 90 IV 6 24.5 83 Example 8 Spring barley was grown in glass dishes filled with soil and treated at a growth height of 10 cm with a 1 wt% aqueous solution of the active ingredient DMC and of active ingredient IV. The action was as follows: Active ingredient kg/ha Growth height cm relative untreated (control) - 30.8 100 DMC 1.5 29.0 94 DMC 6 27.0 88 IV 1.5 27.0 88 IV 6 26.0 84 Example 9 In a vegetation experiment in large enamelled iron vessels filled with soil, spring rye of the "Somro" variety was treated at a growth height of 45 cm with amounts of active ingredients equivalent to the application of 3 kg/ha of compounds I, III and IV as 1 wt% aqueous solutions. Active ingredients CCC, DMC and N,N-dimethylpiperidinium chloride (DPC) were employed analogously (at a rate equivalent to 3 kg/ha). The stems were measured when the rye was ripe. The shortening is apparent from the following table: Active ingredient kg/ha Growth height cm relative untreated (control) - 113.6 100 CCC 3 108.8 95.8 I 3 103.3 90.9 DMC 3 109.6 96.5 III 3 102.9 90.6 DPC 3 107.9 95.0 IV 3 104.9 92.3 Example 10 90 parts by weight of compound I is mixed with 10 parts by weight of N-methyl-apyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

Example 11 20 parts by weight of compound III is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

Example 12 20 parts by weight of compound IV is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

Example 13 20 parts by weight of compound I is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280"C, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

Example 14 20 parts by weight of compound I is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquid is obtained containing 0.1% by weight of the active ingredient.

Example 15 3 parts by weight of compound I is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

Example 16 30 parts by weight of compound III is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

Example 17 40 parts by weight of compound I is intimately mixed with 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion. Dilution in 100,000 parts by weight of water gives an aqueous dispersion containing 0.04 wt% of active ingredient.

Example 18 20 parts by weight of compound I is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable dispersion is obtained.

Example 19 Spring wheat of the "Opal" variety was sprayed at a growth height of 11 cm with aqueous formulations of the active ingredients. Ten days later, at a growth height of the untreated plants of 35 cm, the growth heights of the treated plants were as follows: Active ingredient kg/ha Growth height cm relative untreated (control) - 35.5 100 DPC 1.5 28.0 81.2 6 26.0 75.4 XII 1.5 27.5 79.7 6 24.5 71.0 Example 20 Spring wheat was sprayed as in Example 19. The experimental details and the method of assessment are the same as in Example 19.

Active ingredient kg/ha Growth height cm relative untreated (control) - 35.5 100

1.5 29.0 84.1 6 28.0 81.2 (disclosed in German Laid-Open Application DOS 2 217 697) 1.5 28.0 81.2 VII 6 23.5 68.1 Example 21 Spring barley of the "Villa" variety was sprayed at a growth height of 10 cm with aqueous formulations of the active ingredients. Ten days later, at a growth height of the untreated plants of about 30 cm, the height of the treated plants was as follows: Active ingredient kg/ha Growth hegiht cm relative untreated (control) - 30.5 100 DPC 1.5 28.5 93.4 6 27.0 88.5 XII 1.5 28.0 91.8 6 25.5 83.5 Example 22 Spring barley was sprayed as in Example 21. The experimental details and the method of assessment are the same as in Example 21.

Active ingredient kg/ha Growth height cm relative untreated (control) - 30.5 100 CS -Cnn 1.5 28.5 93.4 6 6 27.5 90.2 (prior art) VII 1.5 27.5 90.2 6 24.5 80.3 Example 23 Spring barley was sprayed as in Example 21. The experimental details and the method of assessment are the same as in Example 21.

Active ingredient kg/ha Growth height cm relative untreated (control) 30.5 100 DMC 1.5 29.0 95.1 DMC 6 27.0 88.5 XVI 1.5 28.0 91.8 V 1.5 28.0 91.8 V 6 26.0 85.2 WHAT WE CLAIM IS: 1. Ammonium and sulfonium salts of the formula

where X denotes

R1 denotes methyl and R2 denotes isopropyl, cyclopentenyl or -chloroethyl, or R1 and R2 together denote -(CH2)5-, -(CH2)2-O-(CH2)2-, -CH2-CH=CH-CH2-NH- or -(CH2)3-S CH2-, and Y denotes the anion of an anionic surfactant selected from alkane sulfonates, dodecylbenzene sulfonate, ether sulfonates, terminally sulfated alkoxylated fatty alcohols, terminally sulfated alkoxylated alkylphenols, alkyl sulfinates, alkane phosphonates, alkane phosphinates, perfluoroalkyl sulfonates, perfluoroalkyl carboxylic acids, a-olefin sulfonates, phosphoric acid monoalkyl and dialkyl esters, dialkylsulfimides, oleic acid and sulfosuccinates.

2. Ammonium and sulfonium salts as claimed in claim 1 wherein

denotes a cation individually depicted hereinbefore.

3. Ammonium and sulfonium salts as claimed in claim 1 or 2 wherein Y denotes RS03 or RCOO where R denotes a hydrophobic organic radical containing at least 6 carbon atoms linked in an aliphatic chain.

4. Ammonium and sulfonium salts as claimed in claim 1 or 2 wherein Y denotes an anion individually depicted hereinbefore.

5. The ammonium and sulfonium salts hereinbefore identified by the formula II to XVII.

6. The compound

**WARNING** end of DESC field may overlap start of CLMS **.

Claims

**WARNING** start of CLMS field may overlap end of DESC **. Example 23 Spring barley was sprayed as in Example 21. The experimental details and the method of assessment are the same as in Example 21. Active ingredient kg/ha Growth height cm relative untreated (control) 30.5 100 DMC 1.5 29.0 95.1 DMC 6 27.0 88.5 XVI 1.5 28.0 91.8 V 1.5 28.0 91.8 V 6 26.0 85.2 WHAT WE CLAIM IS:

1. Ammonium and sulfonium salts of the formula

where X denotes

R1 denotes methyl and R2 denotes isopropyl, cyclopentenyl or ss-chloroethyl, or R1 and R2 together denote -(CH2)5-, -(CH2)2-O-(CH2)2-, -CH2-CH=CH-CH2-NH- or -(CH2)3-S CH2-, and Y denotes the anion of an anionic surfactant selected from alkane sulfonates, dodecylbenzene sulfonate, ether sulfonates, terminally sulfated alkoxylated fatty alcohols, terminally sulfated alkoxylated alkylphenols, alkyl sulfinates, alkane phosphonates, alkane phosphinates, perfluoroalkyl sulfonates, perfluoroalkyl carboxylic acids, a-olefin sulfonates, phosphoric acid monoalkyl and dialkyl esters, dialkylsulfimides, oleic acid and sulfosuccinates.

2. Ammonium and sulfonium salts as claimed in claim 1 wherein

denotes a cation individually depicted hereinbefore.

6. The compound

7. A process for producing an ammonium or sulfonium salt claimed in claim 1, wherein an ammonium or sulfonium salt of the formula

where X, R1 and R2 have the meanings given in claim 1 and Hal denotes a halogen anion, is reacted with an alkali metal or alkaline earth metal hydroxide and an anionic surfactant of the formula HY, where Y has the meaning given in claim 1.

8. Ammonium and sulfonium salts when prepared by a process as claimed in claim 7.

9. A composition for regulating plant growth comprising an ammonium or sulfonium salt as claimed in any of claims 1 to 6 or 8 and a liquid carrier.

10. A composition for regulating plant growth comprising an ammonium or sulfonium salt as claimed in any of claims 1 to 6 or 8 and a solid carrier.

11. A composition as claimed in claim 9 or 10 in the form of a wettable powder, paste or emulsion concentrate containing a surfactant, an antifoam agent, a carrier and 0.5 to 80% by weight of the ammonium or sulfonium salt.

12. A composition as claimed in claim 9 in the form of a solution in an organic solvent or water at a concentration of 1 to 20% by weight.

13. A composition as claimed in any of claims 9 to 12 containing a further growth regulator and/or a fungicide and/or a fertilizer.

14. A composition as claimed in claim 13 containing a further growth regulator hereinbefore individually mentioned.

15. A composition as claimed in claim 13 containing a fungicide hereinbefore individually mentioned.

16. A composition as claimed in claim 9 or 10 substantially as described in any of the foregoing Examples 10 to 18.

17. A process for producing a composition for regulating plant growth wherein a solid or liquid carrier is mixed with an ammonium or sulfonium salt as claimed in any of claims 1 to 6 or 8.

18. A process for the regulation of plant growth, wherein the plants or soil in which the plants are growing are treated with an ammonium or sulfonium salt as claimed in any of claims 1 to 6 or 8.

19. A process as claimed in claim 18 wherein the plants are cereal plants and treatment takes place in the growth phase between tillering and elongation.

20. A process as claimed in claim 18 wherein the plants are ornamental plants and treatment takes place before budding.

21. A process as claimed in claim 18 wherein the plants are plants having fruits which are edible or processable and treatment takes place before harvesting of the fruits.

22. A process as claimed in any of claims 18 to 21 wherein the ammonium or sulfonium salt is applied in a solution or aqueous dispersion to the plant parts above ground.

23. A process as claimed in any of claims 18 to 21 wherein the ammonium or sulfonium salt is applied to the soil in dust, granular or broadcastable form or in a solution or aqueous dispersion.

24. A process as claimed in claim 18, 22 or 23 wherein the plants are barley, wheat or rye.