IL38891A - A method for the regulation of plant growth with 2-haloethanesulfinic acid and some derivatives thereof - Google Patents

Description

38891/2 A method for the regulation of plant growth with 2-haloethanesulfinic acid and some derivatives thereof BAYER ATIENGESELLSCHAT C I36777 Type Ila The present invention relates to the -use as plant-growth-regulating agents of certain 2-haloethanesulphinic acids and their derivatives, some of which are known.

It has been disclosed (see Netherlands Patent Specification 6 802 633), that 2-chloroethanephosphonic acid displays plant-gro h-regul ting properties.

It has now been found that the 2-haloethanesulphinic acid compounds of the general formula 0 It Hal-CH2-CH2-S-R (I) in which Hal is halogen, and R is halogen, hydroxyl, alkoxy with 1 to 20 carbon atoms, haloalkoxy with 1 to 8 carbon atoms, alkenyloxy with 2 to 20 carbon atoms, alkynyloxy with 2 to 8 carbon atoms or cycloalkoxy with up to 12 carbon atoms, show strong plant-growth-regulating properties.

Accordingly, the present invention provides a plant-growth-regulating composition containing as active ingredient a compound of the formula (I) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.

In the above formula (I), Hal is preferably chlorine or bromine whilst R is preferably chlorine, bromine, hydroxyl, straight-chain or branched alkoxy with 1 to 16 carbon atoms, straight or branched haloalkoxy with 1 to 5 carbon atoms, alkenyloxy with 3 to 18 carbon atoms, alkynyloxy with 3 to 5 carbon atoms or cyclohexyloxy. of the formula (I) show a considerably greater plant-growth-regulating activity than 2-chloroethanephosphonic acid, which is chemically the nearest active substance with the same type of activity. Some of the substances to be used according to this invention additionally have microbicidal and fungicidal activity. The compounds according to the invention hence represent a valuable enrichment of the art.

As individual examples of the active substances that can be used according to the present invention, there may be mentioned: 2-chloroethanesulphinic acid chloride, 2-chloro-ethanesulphinic acid bromide, 2-chloroethanesulphinic acid, 2-chloroethanesulphinic acid methyl ester, 2-chloroethanesulphinic acid ethyl ester, 2-chloroethanesulphinic acid n-propyl ester, 2-chloroethanesulphinic acid isopropyl ester, 2-chloroethanesulphinic acid n-butyl ester, 2-chloroethanesulphinic acid sec.-butyl ester, 2-chloroethanesulphinic acid tert.-butyl ester, 2-chloroethanesulphinic acid isobutyl ester, 2-chloroethanesulphinic acid n-pentyl ester, 2-chloroethanesulphinic acid isopentyl ester, 2-chloroethanesulphinic acid neo-pentyl ester, 2-chloroethanesulphinic acid n-hexyl ester, 2-chloroethanesulphinic acid 21-methylpentyl ester, 2-chloroethanesulphinic acid 3'-methylpentyl ester, 2-chloroethanesulphinic acid 2l,2*-dimethyl'butyl ester, 2-chloro- 1· ethanesulphinic acid ^-ethylbutyl ester, 2-chloroethanesulphinic acid 2 '-ethylbutyl ester, 2-chloroethanesulphinic acid n-heptyl ester, 2-chloroethanesulphinic acid 2 '-methylhexyl ester, 2-chloroethanesulphinic acid 3*-methylhexyl ester, 2-chloroethanesulphinic acid 21 ,2 •-dimethylpentyl ester, 2-chloroethanesulphinic acid 31 ,3 '-dimethylpentyl ester, 2-chloroethanesul hi ic acid 21 '-dimeth l ent l ester 2-chloroethane sulphinic acid 3 '-ethylpentyl ester, 2-chloroethanesulphinic acid 2 '-ethylhexyl ester, 2-chloroethanesulphinic acid 2,,3I,3,-trimethylbutyl ester, 2-chloroethanesulphinic acid n-octyl ester, 2-chloroethanesulphinic acid isooctyl ester, 2-chloroethanesulphinic acid 2· ,2 '-dimethylhexyl ester, 2-chloroethanesulphinic acid n-nonyl ester, 2-chloroethanesulphinic acid n-decyl ester, 2-chloroethanesulphinic acid n-undecyl ester, 2-chloroethanesulphinic acid n-dodecyl ester, 2-chloroethanesulphinic acid 2 · ,2 '-dimethyloctyl ester, 2-chloroethanesulphinic acid 21 ,2 '-dimeth ldecyl ester, 2-chloroethanesulphinic acid tetradecyl ester, 2-chloroethanesulphinic acid hexadecyl ester, 2-chloroethanesulphinic acid chloromethyl ester, 2-chloroethanesulphinic acid chloroethyl ester, 2-chloroethanesulphinic acid chloropropyl ester, 2-chloroethanesulphinic acid 1 · , 31-dichloroprop-2-yl ester, 2-chloroethanesulphinic acid vinyl ester, 2-chloroethanesulphinic acid propenyl ester, 2-chloroethanesulphinic acid "buten-1-yl ester, 2-chloroethanesulphinic acid buten-2-yl ester, 2-chloroethanesulphinic acid 2*-methylpropenyl ester, 2-chloroethanesulphinic acid penten-1-yl ester, 2-chloroethanesulphinic acid 11 , 1 •-dimethylallyl ester, 2-chloroethanesulphinic acid octadecen-9-yl ester, 2-chloroethanesulphinic acid propargyl ester, 2-chloroethanesulphinic acid 11-methyl-propargyl ester, 2-chloroethanesulphinic acid 1·,1'- dimethylpropargyl ester, 2-chloroethanesulphinic acid cyclohexyl ester and the corresponding 2-bromoethanesulphinic acid derivatives.

A number of the substances that can be used according to this invention are known, for example 2-chloroethanesulphinic acid chloride, 2-chloroethanesulphinic acid (see Doklady Akad, S R 157 ( 1964),No.1 ,pages 139-142) ;2-chloroethanesulphinic acid methyl ester and 2-bromoethanesulphinic acid methyl ester (see Chem. Ber. 86, 557 (1953) and German Published Specification 2,005,514); 2-chloroethanesulphinic acid methyl ester and ethyl ester, 2-bromoethanesulphinic acid methyl ester and ethyl ester d 2-chloroethanesulphinic acid isopropyl ester (see Tetrahedron Letters £2, 2743 - 2746 (1969)); and 2-chloroethanesulphinic acid tert.-butyl ester (see Zh. obsc. Khim. ^5_, (3)» 475 - 479 (1965)).

Some of the compounds of the formula (I) are new but can be prepared, as can the known analogues, in a simple manner using processes that are known in principle. For example, the sulphinic acid halides are obtained if the corresponding bis- (2-haloethane)-disulphides are halogenated, for example with chlorine in a molar ratio of 1:3» in the presence of inert solvents, such as methylene chloride, at temperatures between -60°C and + 10°C, and the products are then reacted with alcohols. The reaction products are isolated by stripping off the solvent in vacuo and distilling the residue. In order to prepare the sulphinic acids or their esters, the corresponding sulphinic acid halides are reacted with hydrolysing agents or with the corresponding alcohols at temperatures between -10°C and +40°C in the presence of inert solvents, such as methylene chloride.

The active compounds that can be used according to this invention interfere with the physiological phenomena of plant growth and can therefore be used as plant-growth regulators.

The different effects of the active compounds depend essentially on the point in time of the application, with reference to the development stage of the seed or the plant, as are connected with the development stage of the plant.

Thus, with plant -growth regulators the seed dormancy can be broken in order to cause the seeds to germinate at a certain time at which germination is desired, but at which the seed itself shows no readiness to germinate. The seed germination itself can, depending on the concentration applied, either be inhibited or promoted by such active compounds. This inhibition or promotion relates to the seedling development.

The bud dormancy of the plants, that is to say the endogenic annual cycle, can be influenced by the active compounds, so that the plants for instance shoot or blossom at a point in time at which they normally show no readiness to shoot or blossom.

It can also be achieved that the shooting of the buds is retarded, for example in order to avoid, in frost-threatened areas, damage by frosts.

The shoot or root growth can be promoted or inhibited by the active compounds in manner dependent on the applied concentration. Thus, it is possible, for example, to inhibit very strongly the growth of the fully formed plant, or to bring the plant as a whole to a more robust habitus or to produce a dwarf growth.

Of economic interest is the inhibition of plant growth at roadsides and waysides. Furthermore, the frequency of grass-cutting (of lawn-mowing) on swards can be reduced. The growth of woodlands can also be inhibited.

During the growth of the plant, the branching to the side can be multiplied by a chemical breaking of the apical dominance. This is of interest, for example in the propagation of plants by cuttings. In a concentration-dependent manner, however, it is also possible to inhibit the growth of side-shoots, for example The influence of the active compounds on the foliage of the plants can be so regulated that a defoliation is achieved, for example in order to facilitate the harvest or to reduce transpiration at a time at which the plants are to be transplanted.

With growth regulators it is also possible to reduce the transpiration rate of the plants in order to prevent damage by drying out.

In the cases of the influencing of blossom formation, there can be achieved, depending on the applied concentration and the point in time of the application, either a retarding of blossom formation or an acceleration of blossom formation. Under certain circumstances, a multiplication of blossom initiation can also be attained, these effects occurring when the appropriate treatments are carried out at the time of the normal blossom formation. In addition, the formation of predominantly female or predominantly male blossoms can be achieved.

Fruit initiation can be promoted so that more, or seedless, fruits are formed (parthenocarpy). Under certain conditions, the premature fall of fruit can also be prevented, or the fruit fall can be promoted to a certain extent in the sense of a chemical thinning out. The promotion of the fruit fall can, however, also be so exploited that the treatment is effected at the time of the harvest, whereby a facilitation of harvesting occurs. With growth regulators it is also possible to accelerate or retard fruit ripening, to improve the fruit colouration and to cause fruits to come to ripeness within a short period of one another.

Yield increases with the aid of growth regulators can be attained by promotion of fruit initiation, by formation of larger fruits and by promotion of the vegetative growth. Further, possible .

The active compounds to be used according to the present invention can be converted into the usual formulations, such as solutions, emulsions, suspensions, powders, pastes and granulates. These may be produced in known manner, for example by mixing the active compounds with extenders, that is, liquid or solid or liquefied gaseous diluents or carriers, optionally with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents.

As liquid diluents or carriers, there are preferably used aromatic hydrocarbons, such as xylenes, toluene,benzene or alkyl naphthalenes, chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethyl-formamide, dimethyl sulphoxide or acetonitrile, as well as water.

By liquefied gaseous diluents or carriers are meant liquids which would be gaseous at normal temperatures and pressures, e.g. aerosol propellants, such as halogenated hydrocarbons, e.g. freon.

As solid diluents or carriers, there are preferably used ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, or ground synthetic minerals, such as highly-dispersed silicic acid, Preferred examples of emulsifying agents include non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylarylpoly lycol ethers, alkyl sulphonates, alkyl sulphates and aryl sulphonates; and preferred examples of dispersing agents include lignin, sulphite waste liquors and methyl cellulose.

The formulations contain, in general, from 0.1 to 95» preferably from 0.5 to 90, per cent by weight of active compound.

The active compounds may be applied as such or in the form of their formulations or of the application forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, spray powders, pastes, soluble powders, dusting agents and granulates. Application may take place in any usual manner, for example by watering, squirting, spraying, scattering and dusting.

The concentrations of active compound can be varied within a fairly wide range. In general, concentrations of from 0.0005 to 2fo, preferably from 0.01 to 0.5$, by weight are used.

Further, there are used, in general, 0.1 to 100 kg, preferably 1 to 10 kg, of active compound per hectare of soil area.

Generally, application of the plant-growth regulators is effected within a preferred period of time, the precise delimitation of which is governed by the climatic and vegetative circumstances.

The present invention also provides a method of regulating the growth of plants which comprises applying to the plants or a plant habitat a compound of the formula (I), alone or in the The present invention further provides plants of which the growth has been regulated by their being grown in areas in which immediately prior to and/or during the time of the growing a compound of the formula (I) was applied alone or in admixture with a diluent or carrier.

The activity of the compounds to be used according to this invention can be seen from the following usage i!xamples.

Example A Acceleration of ripening in bananas.

Solvent: 10 parts by weight methanol Emulsifier : 2 parts by weight polyethylene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and water is added until the desired concentration is reached.

In each case 3 unripe bananas are sprayed with 20 ml of the preparation of active compound. The acceleration of ripening in days is determined by comparison with the control fruits.

There is staledjnda s the time by which the treated fruits ripened before the untreated control fruits.

The active compounds, the concentration of the active compounds and the results can be seen from the following Table 1 : a b l e 1 Acceleration of ripening in bananas Active compound Acceleration of ripening in days compared with the control 1000 ppm 2000 ppm 0 tl Cl-CHo-CH^-P-OH 10 10 T a b 1 e 1 (continued) Acceleration of ripening in bananas Active compound Acceleration of ripening in days compared with the control 1 000 pt>m 2000 ppm 0 Cl-CH2-CH2-S-0-CH(CH3 )2 (4) 1 1 1 1 0 II Cl-CH2-CH2-S-OC4H9-n ( 5 ) 1 1 1 1 Example B Germination cC ground-nut seeds Solvent : 1 0 parts by weight methanol Emulsifierj 2 parts by weight polyethylene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and water is added until the desired concentration is reached.

In each case 10 ground-nut seeds are laid out on filter paper in 2 Petri dishes with in each case 20 ml of the preparation of active compound. After 48 hours, the number of germinated ground-nut seeds is determined.

The active compounds, the concentrations of the active compounds, and the results can be seen from the following Table 2 : a b l e 2 Germination of ground-nut seeds Active compound Concentration Number of germinated seeds a b l e 2 (continued) Germination of ground-nut seeds Active compound Concentration Number of germinated seeds CH0-P-GH 100 ppm OH C1-CH2-CH2-S-0C2H5 (3) 100 ppm 17 0 «I Cl-CH2-CH2-S-0-CH(CH5)2 (4) 00 ppm 16 0 Cl-CH2-CH2- -0C4H9-n (5) 100 ppm 14 C1-CH2-CH2-S-0H (21) 100 ppm 15 0 It Cl-CH2-CH2-S-0C5H11-n (8) 100 ppm 13 Example 0 Retardment of senescence in barley Solvent: 10 parts by weight methanol Emulsifier: 2 parts by weight polyethylene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and water is added until the length. 4 such leaf pieces are each placed on filter paper in a Petri dish with 4 ml of the solution of active compound.

G-rowth regulators retard the yellowing of the leaf pieces ation compared with the water control. After 4 days, this retardae*** of senescence is evaluated on the following scale: Symbols t 0 = no retard¾K«2P of senescence ation + = slight retardment of senescence ation ++ = strong retardment of senescence ation = very strong retards©*** of senescence The active compounds, the concentrations of the active compounds and the results can be seen from the following Table 3: T a l e 3 Retardment of senescence in barley Active compound Concentration Retar¾»¾s£- of in ppm senescence Water (control) - OH (known) 0 " 1000 Cl-CH2-CH2-S-0-CH(CH3)2 (4) 200 0 " 1000 Cl-CH2-CH2-S-0C4H9-n (5) 200 i? 1000 C1-CH2-CH2-S-0CH5 (6) T a b 1 e 3 (continued) ation Retardment of senescence in barley Concentration Retarcfroo P of Active compound in ppm senescence 0 0 II Br-CH2-CH2-S-Cl *) 1000 0 0 0 II Br-CH2-CH2-S-0C2H5 (14) 1000 +++ 0 Cl-CI^-CI^-S-OCgH,, 7~n (9) 1000 -H-+ *) dissolved in acetone instead of in methanol Example D Growth inhibition in beans Solvent: 10 parts by weight methanol Emulsifier: 2 parts by weight polyethylene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and water is added until the desired concentration is reached.

Young bean plants about 10 cm in height are sprayed with the the growth increase is measured and the growth inhibition is c lculated as a percentage of the growth increase of the control treated with a preparation containing only solvent, emulsifier and water plants 1005-· means complete inhibition of growth, and Qffo means no inhibition of growth.

The active compounds, the concentrations of the active compounds and the results cun be seen from the following Table 4: a b l e 4 Growth inhibition in beans Concentration Inhibition compared Active compound in ppm with the control in jo 0 II (known) 0 C1-CH2-CH2-S-0C2H5 (3) 500 41 0 l« (4) Cl-CH2-CIi2-S-0-CH(CH5)2 500 45 0 It Cl-CH2-CH2-S-0C4Hg-n (5) 500 45 Example E Growth inhibition in cress seedlings Solvent: 10 parts by weight methanol Emulsifier: 2 parts by weight polyethylene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and water is added until the cress seeds remain adhering to the moist filter paper, the latter is placed vertically in a glass beaker of 250 ml capacity. The glass beaker is charged with 20 ml of the preparation of active compound and covered with a glass plate.

After 4 days, the seedlings are measured and the percentage inhibition of growth, in length compared with the control (distilled water with the corresponding amounts of solvent and emulsifier) is calculated. means complete inhibition of growth, and 0$¾ means no inhibition of growth.

The active compounds, the concentrations of active compound and the results can be seen from the following Table 5: T a ¾ 1 e 5 Growth inhibition in cress seedlings Concentration Growth inhibition Active compound in ppm in C1-CH2-CH2-P-0H 200 60 OH (known) 0 Br-CHg-CHg-S-Cl *) (1) 200 75 0 II Br-CH2-CH2~S-OC5H11 -n (10) 200 80 0 0 Br-CH2-GH2-S-0-CH(CH5)2 (12) 200 70 0 It Br-CH -CH -S-0C H -n (13) 200 80 Example F Growth inhibition in tomatoes Solvent: 10 parts by weight acetone Emulsifier: 2 parts by weight polyethylene sorbitan monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and water is added until the desired concentration is reached.

Young tomato plants 1 5 cm in height are sprayed with the preparation of active compound until dripping wet. After 1 4 days, the growth increase is measured and the growth inhibition is calculated as a percentage of the growth increase of the control plants. 0O o means complete inhibition of growth, and Qffc means no inhibition of growth.

The active compounds, the concentrations of the active compounds and the results can be seen from the following Table 6 : T a b 1 e 6 Growth inhibition in tomatoes Concentration Inhibition Active compound in ppm in o 0 »· C1-CH0-CH9-P-OH 2000 78 » 1 000 65 OH (known) 0 (I Cl-CH^-CH^-S-Cl (2 ) 2000 90 . 1 000 90 The preparation of the compounds to be used according to this invention is illustrated in the following preparative example 1 II 213 g (3 moles) of chlorine are introduced, at -60°C, into a solution of 280 g (1 mole) of bis-(2-bromoethane)-disulphide in 800 ml of methylene chloride, and thereafter 64 g (2 moles) of methanol in 100 ml of methylene chloride are added at this temperature, viith stirring. The reaction solution is allowed to come to room temperature whilst stirring is effected, in the course of which hydrogen chloride and methyl chloride are evolved. Thereafter, the solvent is stripped off in vacuo and the residue is distilled at 98°C and 11 mm Hg.210 g (60$ of theory) of 2-bromoethanesulphinic acid chloride are obtained as 22 a brownish liquid of refractive index = 1.5578. 2-chloroethanesulphinic acid chloride was prepared analogously. 0 It C1-CH2-CH2-S-C1 (2) 240 g (82$ of theory) were obtained as a colourless liquid: boiling point 72°C at 6 mm Eg; refractive index n 4 = 1.5200.

Example 2 0 It C1-CH2-CH2-S-0C2H5 (3) 29.4 g (0.2 mole) of 2-chloroethanesulphinic acid chloride are added dropwise at 0°C to 9.5 g (0.205 mole) of ethanol in 50 ml of methylene chloride. After the mixture has been stirred for a further 2 hours at 20 to 40°C, the solvent is stripped off in vacuo and the residue is distilled at 30°C and 0.1 mm Hg. 20 g (64$ of theory) of 2-chloroethanesulphinic acid ethyl ester are obtained a a col urless li uid f refractive index The following compounds are prepared in a manner analogous to that above (boiling-point data specify the pressure (mmKg) f rst) * Physical Properties Yield Structure (boiling point and { > of refractive index theory) 0 »i bp. 0.2/45°C Cl-CH2-CH2-S-0-CH(CH5)2 (4) n22 = 1.4720 50 0 «I Cl-CH2-CH2-S-OC4H9-n ( 5 ) bp. 0.l/63-65°C n22 = 1.4711 53 0 It C1-CH2-CH2-S-0CH5 (6) bp. 6/64°C n23 = 1.5020 65 0 Cl-CH2-CH2-S-OC5H11 -n (8) bp.0.05/90°C n23 = 1.4708 75 C1-CH2-CH2-S-0C 8H1 ?-n ( 9 ) bp. 0.1/102°C n22 = 1.4700 52 0 II Br-C^-CHg-S-OC^^n (10) bp. 0.01/90°C £ * = 1.4890 51 0 40 Physical Properties Yield Structure (boiling point and ($¾ of refractive index) theory) -GH2-GH2-S-0-Cil(CH3)2 (12) bp.O.Ol/52°C .2 n" = 1.4980 D Br-CH2-GH2-S-0G4H9-n (13) bp.0.4/74°C n|2 = 1.4990 70 0 » Br-CH2-OH2-3-OG2K5 (14) bp. 0.3/55 C 2; n" = 1.5050 lV 0 It Cl-CH2-CH2-S-0-CH2-CH2-Cl (15) n^4 = 1.4989 92 0 II Cl-CH2-CiI2-S-0-CH(CH2Cl)2 (16) n^ = 1.4958 89 0 II C1-CH2-CH2-S-0(CH2)15-CH5 (17) n^4 = 1.4698 59 0 II Cl-CH2-CH2-S-0-CH2-C≡CH (18) n 4 = 1.4990 85 !? (19) Cl-CH2-CH2-S-0 ( CH2 ) Cl-CH2-CH2-S-0-CH2-CK=CH2 (20) n^4 = 1.4920 80 Example 3 0 Cl-CH2-CH2-3-0H (21 ) 74 g (0.5 mole) of 2-chloroethanesulphinic acid chloride cooling with ice are effected. After stirring for a further half-hour, the v;ater is stripped off in vacuo, the residue is taken up in methylene chloride, the solution is dried over sodium sulphate and the solvent is stripped off in vacuo. A colourless oil of refractive index ^ = 1.5040 is left; yield: 60 g (94^ of theory).

Claims (2)

1. What we claim is: 1. A plant-growth-regulating composition containing as active ingredient a 2-haloethanesulphinic acid compound of the general formula 0 It Hal-CH2-CH2-S-R (I) in which Hal is halogen, and R is halogen, hydroxy!, alkoxy with 1 to 20 carbon atoms, haloalkoxy with 1 to 8 carbon atoms, alkenyloxy with 2 to 20 carbon atoms, alkynyloxy with 2 to 8 carbon atoms or cycloalkoxy with up to 12 carbon atoms* inadmixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
2. 2. A plant-growth-regulating composition containing as active ingredient a compound of the formula in cl im 1 , in which Hal is chlorine or bromine and R is chlorine, bromine, hydroxyl, straight-chain or branched alkoxy with 1 to 16 carbon atoms, straight-chain or branched haloalkoxy with 1 to 5 carbon atoms, alkenyloxy with 3 to 18 carbon atoms, alkynyloxy with 3 to 5 carbon atoms or cyclohexyloxy, in acLmixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 3. plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 tt Br-CH2-CH2-S-Cl (1 ) in admixture with a solid or liquefied gaseous diluent or containing a surface-active agent . 4. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent . 5. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 »» C l-CH . -OH .-S-0CoH5 (3 ) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 6. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 Cl-CH2-CH2-S-0-CH (GH3 )2 ( 4 ) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent . 7. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 II Cl-CH2-CH2-S-0C4H9-n (5 ) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent . ingredient is a compound of the formula 0 II C1-CH2-CH2-S-0CH3 (6 ) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 9. plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 10. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 It C1-CH2-GH2-S-0C5H11 -n (8) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 11. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 It Cl-CH2-CH2-S-0C8H17-n (9) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 12. A plant-growth-regulating composition in which the active ingredient is a compound of the formula Br-CH2-CH2-S-OC5H1 ,,-n (10) in admixture with a solid or liquefied gaseous diluent or carrier * in admixture with a liquid diluent or carrier containing a surface-active agent. 13. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 14. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 Br-CH2-CH2-S-0-CH(CH5)2 (12) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 15. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 Br-CH2-CH2-S-OC4H9-n (13) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 16. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 Br-CH2-CH2-S-OC2H5 (U) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 17. A plant-growth-regulating composition in which the active ingredient is a compound of the formula 0 II C1-CH2-CH2-S-0H (21 ) in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 18. A composition according to any of claims 1 to 17 containing from 0.1 to 959» of the active compound, by weight. 19. A composition according to claim 18 containing from 0.5 to 90# of the active compound, by weight. 20. A method of regulating the growth of plants which comprises applying to the plants or a plant habitat a compound of the formula given in any of claims 1 to 17» alone or in the form of a composition containing as active ingredient a compound of the formula given in any of claims 1 to 17 in admixture with a diluent or carrier. 21. A method according to claim 20 in which a composition is used containing from 0.0005 to 2 of the active compound, by weight. 22. A method according to claim 21 in which a composition is used containing from 0.01 to 0. $ of the active compound, by weigh . 23. A method according to any of claims 20 to 22 in which the 0.1 to 100 kg per hectare. 24. A method according to claim 23 in which the active compound is applied to an area of soil in an amount of 1 to 10 kg per hectare. 25. A method according to any of claims 10 to 24 in which the active compound is one of those hereinbefore mentioned in any of Examples A to F. 26. Plants of which the growth has been regulated by their being grown in areas in which immediately prior to and/or during the time of the growing a compound of the formula given in any of claims 1 to 17 was applied, alone or in admixture with a diluent or carrier. Le A 13 609 27