IL47156A - Phosphonic acid and thionophosphonic acid ester amides their preparation and their use as plantgrowth regulators - Google Patents

Description

Novel phosphonic and thionophosphonic acid ester amides, their preparation and their use as plant-growth regulators BAYER AKTIENGESELLSCHAFT Type la The present invention relates to certain new N-iso-propyl-2-chloroethane-( thiono )-phosphonic acid ester amides, to a process for their preparation and to their use as active compounds for regulating plant growth.

It has already been disclosed that 2-chloroethane-phosphonic acid exhibits plant growth-regulating properties (see published Netherlands Patent Application 68/02,633 However, the activity of this compound is not always entirely satisfactcry, especially if low amounts and low concentrations are used.

The present invention provides, as new compounds, the N-isopropyl-2-chloroethane-( thiono )-phosphonic acid ester amides of the general formula in which X is oxygen or sulphur, and R is acetyl or a group of the formula wherein X1 is oxygen or sulphur, R* is alkoxy with 1 to 4 carbon atoms or 2-chloroethyl, and R" is alkoxy or alkylamino, each with 1 to 4 carbon atoms, or an Hg- group.

The compounds of this invention have been found to Preferably R is acetyl or the group, in which X' is oxygen or sulphur, R'isa 2-chloroethyl radical or straight-chain or branched alkoxy with 1 to carbon atoms (methoxy, ethoxy and propoxy should be mentioned specifically in this context) and R" is an amino group, or straight-chain or branched alkoxy or alkylamino, each with 1 to 3 carbon atoms (preferred radicals being, in particular, methoxy, ethoxy, monomethylamino , monoethylamino , mono-n-propylamino and mono-isopropylamino) .

This invention also provides a process for the preparation of an N-isopropyl-2-chloroethane-( thiono)-phosphonic acid ester amide of the formula (I), in which an N-isopropyl-2-chloroethane-( thiono)-phosphonic acid amide halide of the general formula in which X has the above-mentioned meaning, and Hal is halogen, preferably chlorine, is reacted with a compound of the general formula R - 0 - Y (III), in which R has the above^-mentioned meaning, and Y is hydrogen or one equivalent of an alkali metal, alkaline earth metal or ammonium, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a solvent or diluent.

Sur r s - - - - phosphonic acid ester amides according to the invention exhibit a substantially greater plant-growth-regulating action than 2-chloroethanephosphonic acid, known from the state of the art, which is chemically the nearest active compound of the same type of action. A point to be singled out above all is that the compounds according to the invention are substantially more suitable for inhibiting vegetative plant growth than is 2-chloroethanephosphonic acid, The compounds according to the invention thus represent a valuable enrichment of the art.

If N-iso-propyl-2-chloroethanephosphonic acid amide chloride and sodium acetate are used as starting materials, the course of the reaction can be represented by the following equation: The N-isopropyl-2-chloroethane-( thiono)-phosphonic acid amide halides of the formula (II) which can be used according to the invention are either already known or can be prepared according to generally customary processes (see German Offenlegungsschrift (German Published Specification) 1,950,099; The following may be mentioned as examples of the compounds of the formula (II) which can be used according to the invention: N-isopropyl-2-chloroethane-phosphonic acid amide chloride and N-isopropyl-2-chloroethane-thiono-phosphonic acid In the formula (III), Y preferably represents hydrogen, sodium, potassium, calcium or ammonium. The compounds of the formula (III) which can be used according to the invention are known and can be prepared in accordance with generally customary methods, in most cases also on an industrial scale (see Belgian Patent Specification 756,981).

The following may be mentioned as examples of the compounds of the formula (III) which can be used according to the invention: acetic acid, sodium acetate and potassium acetate, and also 0, O-dimethylphosphoric acid diester, 0,0-diethylphosphoric acid diester, 0,O-di-n-propylphosphoric acid diester, 0,0-di-isopropyl-phosphoric acid diester, 0-eth l-O-n-propyl-phosphoric acid diester, 0-ethyl-O-isopropyl-phosphoric acid diester, O-methyl-N-methyl-phosphoric acid ester amide, O-raethyl-N-ethyl-phosphoric acid ester amide, O-ethyl-N-methyl-phosphoric acid ester amide, O-ethyl-N-ethyl-phosphoric acid ester amide, 0-n-propyl- -methyl-phosphoric acid ester amide, O-n-propyl-N-ethyl-phosphoric acid ester amide, O-isopropyl-N-methyl-phosphoric acid ester amide, O-isopropyl-N-iso-propyl-phosphoric acid ester amide, O-methyl-N-isopropyl-phosphoric acid ester amide, 0-ethyl-N-isopropyl-phosphoric acid ester amide, O-methyl-phosphoric acid ester amide, O-ethyl-phosphoric acid ester amide, 0-n-propyl-phosphoric acid ester amide, O-isopropyl-phosphoric acid ester amide, N-meth l-2-chloroethane-phosphonic acid amide, N-ethyl-2-chloroethane-phosphonic acid amide, N-n-propyl-2-chloroethane-phosphonic acid amide, N-isopropyl-2-chloroethane-phosphonic acid amide, as well as the sodium, potassium, ammonium and calcium salts of the above-mentioned The process according to the invention for the preparation of the new N-isopropyl-2-chloroethane-( thiono)-phosphonic acid ester amides of the formula (I) is preferably carried out in the presence of a suitable solvent or diluent. Practically all inert organic solvents can be used for this purpose, especially aliphatic and aromatic hydrocarbons, such as petroleum ether, benzine, benzene, toluene and xylene; chlorinated aliphatic and aromatic hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene; ethers, such as diethyl ether, dibutyl ether and dioxan; ketones, such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone; and nitriles, such as acetonitrile and propionitrile.

All customary acid-binding agents can be used as acid acceptors in carrying out the process according to the invention. Amongst these there should be mentioned especially alkali metal carbonates, such as potassium carbonate and sodium carbonate, alkali metal alcoholates, such as sodium ethylate and sodium meth late, and aliphatic, aromatic or heterocyclic amines, such as, for example, triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine and pyridine.

The reaction temperatures can be varied over a fairly wide range. In general, the reaction is carried out at between 0° and 100°C, preferably between 10° and 70°C. The reaction according to the invention is generally carried out under normal pressure.

In carrying out the process according to the invention for the preparation of the compounds of the formula (I), pre per mole of N-isopropyl-2-chloroethane-( thiono)-phosphonic acid amide halide of the formula (II). However, it is also possible to use one or other reactant in excess, although the yield is not significantly improved thereby.

In general, the reaction products of the formula (I) are isolated by, if appropriate, filtering off the crystalline precipitate produced during the reaction after the latter has been completed, adding water to the filtrate and extracting the resulting mixture repeatedly with a water-insoluble organic solvent. After drying under reduced pressure, the combined organic phases are concentrated. In some cases, working up by an aqueous method is superfluous. In that case, the procedure followed is first to filter off the precipitate which has formed during the reaction and then to concentrate the filtrate under reduced pressure.

The compounds of the formula (I) which can be prepared according to the invention are in most cases obtained, after working up, in the form of oils which cannot be distilled without decomposition. However, purification is possible by freeing the oily products from the last volatile constituents by so-called "slight distillation", that is to say by prolonged heating under reduced pressure to moderately elevated temperatures. The refractive index is used to characterise the compounds which are obtained as oils even after purification. Some compounds, however, are obtained in a crystalline form; they can be characterised as pure substances by their sharp melting point.

A particular embodiment of the process according to the invention is employed when preparing symmetrical compounds of In these cases it is not necessary to react the starting compound of the formula (II) with the corresponding hydroxy compound of the formula (III) or a salt of this hydroxy compound. Instead, the procedure followed is to treat the N-isopropyl-2-chloroethane-( thiono)-phosphonic^ acid amide halide in question, in a solvent or diluent, for one or more o 1000 hours at a temperature of between 0 and C with a mixture of an acid acceptor such as pyridine, water and an organic solvent such as methylene chloride. Working up is effected by extracting the reaction mixture repeatedly with dilute hydrochloric acid, subsequently drying the organic phase and concentrating it under reduced pressure.

The following may be mentioned as examples of the N-isopropy1-2-chloroethane-(thiono)-phosphonic acid ester amides of the formula (I): 0-acetyl-N-isopropyl-2-chloro-ethane-phosphonic acid ester amide, O-acetyl-N-isopropyl-2-chloroethane-thiono-phosphonic acid ester amide, 0-(0,0-dimethylphosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0,0-diethylphosphoryl)-N-isoprop l-2-chloroethane-phosphonic acid ester amide, 0-(0,0-di-n-propyl-phosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide , 0-(0,0-di-isopropylphosphoryl)-N-isopropyl-2-chloro-ethane-phosphonic acid ester amide, 0-(0-eth l-0-n-propyl-phosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0-ethyl-0-isopropylphosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0,0-dimethyl-thionophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0,0-diethyl-thionophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0,0-di-n-propyl- ester amide, 0-(0,0-di-isopropyl-thionophosphoryl)-N-iso-propyl-2-chloroethane-phosphonic acid ester amide, 0-(0-methyl-N-methylamidophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-( O-methy1-N-ethyl-amido-phosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-( O-ethyl-N-methyl-amidophosphoryl )-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0-ethyl-N-ethyl-amidophosphoryl )-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0-n-propyl-N-ethyl-amidophosphoryl)-N-iso-propyl-2-chloroethane-phosphonic acid ester amide, 0-(0-isopropyl-N-methylamidophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0-n-propyl-N-methyl-amido-phosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide , 0-(O-isopropyl-N-isopropyl-amidophosphoryl)-N-iso-propyl-2-chloroethane-phosphonic acid ester amide, 0-(0-methyl-N-isopropyl-amidophosphoryl)-N-isopropyl-2-chloroethane phosphonic acid ester amide, 0-(0-eth l-N-isopropyl-amido-phosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0-methyl-N-methyl-amidothionophosphoryl)-N-isopropyl 2-chloroethane-phosphonic acid ester amide, 0-(0~meth l-N-ethyl~amidothionophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0-eth l-N-meth l-amido-thionophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0-ethyl-N-ethyl-amidothionophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0-methyl-amidophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0-ethyl-amidophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, O-(0-n-propyl-amidophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid amidothionophosphoryl)-N-isopropyl-2-chloroethane--phosphonic acid ester amide, 0-(0-ethyl-amidothionophosphoryl)- -iso-propyl-2-chloroethane-phosphonic acid ester amide, 0-(0-n-propyl-amidothionophosphoryl)-N-isopropyl-2-chloroethane-phosphonic acid ester amide, 0-(0-isopropyl-amidothiono-phos horyl)-N-isopropyl-2-chloroethane-phosphoric acid ester amide , P,P'-di-isopropylamino-di-2-chloroethane-pyrophosphonic acid diamide and P,P 1 -di-isopropylamino-di-2-chloroethane-pyrothionophosphonic acid diamide.

The active compounds according to the invention affect the physiological metabolism of plant growth and can therefore be used as plant growth regulators.

The diverse actions of the active compounds essentially depend on the point in time at which they are used, relative to the stage of development of the seed or of the plant, and on the concentrations usedo Plant-growth regulators are used for various purposes related to the stage of development of the plant.

The growth of plants can be greatly inhibited with the compounds according to the invention. This inhibition of growth is of interest in grasses, for the purpose of reducing the frequency of cutting grass. An inhibition of vegetative growth is also of great importance in cereals, since lodging can thereby be reduced or completely prevented.

In the case of many crop plants, the inhibition of vegetative growth permits denser planting of the crop, so that a greater yield per area of ground can be achieved. A further mechanism of increasing the yield by means of growth inhibitors is based on the fact that the nutrients benefit vegetative growth is restricted.

Promotion of vegetative growth can also be achieved with the compounds according to the invention. This is of great utility if it is the vegetative parts of the plants which are harvested. Promoting the vegetative growth can, however, also simultaneously lead to a promotion of generative growth so that, for example, more fruit, or larger fruit, is formed.

Parthenocarpous fruit can be formed under the influence of the active compounds. Furthermore, the gender of the blossoms can be influenced.

Using the active compounds according to the invention it is also possible favourably to influence the production or efflux of secondary plant materials. The stimulation of latex flow in rubber trees may be mentioned as an example.

During the growth of the plant, lateral branching can also be increased by chemical breaking of the apical dominance. There is interest in this, for example, in the case of plant propagation by cuttings. However, depending on the con-centration, it is also possible to inhibit the growth of the side shoots, for example to prevent the formation of side shoots in tobacco plants after decapitation and thus to promote leaf growth,.

The influence of the active compounds on the amount of leaf on the plants can be so controlled as to achieve defoliation, for example to facilitate harvesting or to lower the transpiration at a point in time at which the plant is to be transplanted.

Under certain conditions, premature shedding of fruit of a chemical thinning out, up to a certain degree. However, assisting the shedding of fruit can also be utilised by carrying out the treatment at harvest time, which facilitates ha i*vesting. 5 Using the active compounds according to the invention i t is furthermore possible to accelerate or delay ripening of ru.it and improve the colourin of fruit. Concentrating the ripening of fruit within a certain per od of time is also possible. The desired effects can be achieved by varying 10 the concentrations of active compounds used and by application at different times during the development of the plant.

Using the compounds according to the invention, frost resistance and drought resistance ca be induced in the plants.

The latent period of seeds or buds of plants, that is V,> to say the endogenic annual rhythm, can be influenced by the active compounds, so that, for example, the plants germinate, shoot or blossom at a time at which they normally show no readiness to do so.

Using the active compounds it is also possible to delay 20 the shooting of buds or the germination of seeds, for example to avoid damage by late frosts in regions where frost is a h ard .

The active compounds according to the present invention can be converted into the usual formulations, such as 25 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 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 iso-butyl ketone or cyclohexanone, or strongly polar solvents, such as dimethyl formamide, dimethyl sulphoxide or aceto-nitrile, as well as water.

By liquefied gaseous diluents or carriers are meant liquids which would be gaseous at normal temperatures and pressures, for example aerosol propellants, such as halo-genated hydrocarbons, for example 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, alumina or silicates.

Preferred examples of emulsifying and foam-forming agents include non-ionic and anionic emulsifiers, such as polyoxy-ethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alk larylpolyglycol ethers, alkyl sulphonates, alkyl sulphates and aryl sulphonates as well as albumin hydrolyzation products; and preferred examples of dispersing agents include lignin sulphite waste liquors and The active compounds according to the invention can "be present in the formulations as a mixture with other active compounds, such as fungicides, insecticides and acaricides.

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

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders, pastes, soluble powders, dusting agents and granules. They may be used in the customary manner, for example by watering, spraying, atomising, scattering, dusting and the like.

The active compound concentrations can be varied within a fairly wide range. In general, concentrations of 0.0005 to 2%, preferably of 0.01 to 0. $, by weight are used.

Further, 0.01 to 50 kg, preferably 0.1 to 10 kg, of active compound are generally used per hectare of soil surface.

The preferred period of time within which the growth regulators are used depends on the climatic and vegetative circumstances .

The compounds according to the invention not only have very good plant-growth-regulating properties but in addition possess herbicidal activity.

The present invention also provides a plant-growth-regulating composition containing as active ingredient a compound of the present invention 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. ing the growth of plants which comprises applying to the plants or a plant habitat a compound of the present invention alone or in the form of a composition containing as active ingredient a compound of the present invention in admixture with a diluent or carrier.

The present invention further provides plants, the growth of which 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 present invention was applied alone or in admixture with a diluent or carrier.

The biotest Examples which follow illustrate the activity of the compounds according to the invention as growth regulators without excluding the possibility of other applications as growth regulators.

Example A Acceleration of ripening/bananas Solvent: 10 parts by weight of methanol Emulsifier: 2 parts by weight of polyethylene-sorbitane monolaurate .

To produce an appropriate preparation of active compound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier and made up to the desired concentration with water.

In each case, 3 unripe bananas were sprayed with 20 ml of the preparation of active compound. The acceleration in ripening in days compared to untreated control fruit was determined.

The active compounds, active-compound concentrations and results can be seen from the table which follows.

T b 1 e A CD leration of ripening/bananas Active compound Active compound concentration in °fo o 0 0.2 0.1 Gl-CH2-GH2-P-NHC5H7-iso 0-CO-CH, (1) Cl-CH -CHo P-0H 0.2 OH 0.1 (known) Water (control) Example B R tardation of growth/tomatoes Solvent: 10 parts by weight of methanol Emulsifier: 2 parts by weight of polyethylene-sorbi tane monolaurate To produce an appropriate preparation of active compound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier and made up to the desired concentration with water.

Tomato plants about 30 cm high were sprayed with the preparations of active compound until dripping wet. After 10 days, the additional growth was measured and the retardation of growth in of the additional growth of the control plants was calculated. 100$ denotes cessation of growth and 0$ denotes a growth which corresponded to that of the untreated control plants.

The active compounds, active compound concentrations and results can be seen from the table which follows„ a l e B Retardation of growth/toma Active compound Active compound concentration in io Water (control) 0 (known) (6) T a l e B (continuation) Retardation of growth/tomatoes Active compound Active compound concentration in io 0 I C1-CH2-CH2^^ 0 P_0-P_GH2-GH2-G1 0.2 ΒΟ-Ο,Η,-,- Η^ NH-C¾H«-iso 0.1 5 7 (5) Example G Retardation of growth/beans Solvent: 10 parts by weight of methanol Emulsifier: 2 parts by weight of polyethylene-sorbitane monolaurate To produce an appropriate preparation of active compound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier and made up to the desired concentration with water.

Young bean plants about 10 cm high were sprayed with the preparation of active compound until dripping wet.

After 14 days, the additional growth was measured and the retardation of growth in # of the additional growth of the control plants was calculated. 100$ denotes cessation of growth and 0 denotes a growth which corresponded to that of the untreated control plants.

The active compounds, active-compound concentrations and results can be seen from the table which follows » T a b l e C Retardation of growth/beans Active compound Active compound con¬ CTN centration in o Water (control) 0 II C1-CH2-CH2-P-0H 0.05 OH (known) C1-CH2-CH2 I P-0-P(0C2H5)2 0.05 iso-C^ H' (2) Cl-CH2-CH2-P-NHC3H7-iso (1) 0o05 0-CO-CH, The process of this invention is illustrated "by the following preparative Examples.

Example 1 0 Cl-CH2-CH2-P-NHC5H7-iso (1) 0-CO-CH^ 4.1 g (0.05 mole) of dry sodium acetate were added to a solution of 10.2 g (0.05 mole) of N-isopropyl-2-chloroethane-phosphonic acid amide chloride in 50 ml of acetonitrile. The mixture was stirred for 5 hours at 50°C and the crystalline precipitate contained in the reaction mixture was then filtered off. The filtrate was concentrated under reduced pressure and the residue was subjected to "slight distillation." This gave 10 g (88$ of theory) of Q-acetyl-N-isopropyl-2-chloroethane-phosphonic acid ester amide in the A form of a colourless oil having a refractive index n^ of 1.4709.

The compounds listed in Table 1 below were prepared analogously: T a b l e 1 C1-CH2-CH2 _ X II P-0R (I) iso-Ο,Η,,-ΗΝ' 3 7 Example 5 A mixture of 9 g ( 0. 1 1 mole) of pyridine, 0.9 g ( 0.005 mole) of water and 20 ml of methylene chloride was added to a solution of 20.4 g ( 0. 1 mole) of N-isopropyl-2-chloroethanephosphonic acid amide chloride in 50 ml of methylene chloride at 0-5°C. The reaction solution was stirred for a further 1 -2 hours at room t emperature and was then extracted with 1 N hydrochloric acid. After drying the organic phase over sodium sulphate, the solvent was stripped off. 1 2.5 g (70 of theory) of Ρ,Ρ'-di-isopropylamino-di-2-chloroethanepyrophosphonic acid diamide were obtained in the form of white crystals of melting point 1 35°C« The compound mentioned in Example 6 which follows was prepared analogously.

Example 6 The compound was found to have a refractive index n^3 of 1.4830.

The structures of the compounds of which the preparation is described in Examples 1-6 were in each case demonstrated by IR and MR spectroscopy.

Claims (12)

1. What we claim is: 1. N-isopropyl-2-chloroethane-( thiono )-phosphonic acid ester amides of the general formula χ CI—CHQ—GH^ . II ^^^P-OR (I) iso-C5H7-H in which X is oxygen or sulphur, and R is acetyl or a group of the formula wherein X1 is oxygen or sulphur, R1 is alkoxy with 1 to 4 carbon atoms or 2-chloroethyl, and R" is alkoxy or alkylamino, each with 1-4 carbon atoms, or an -NHg group.

2. Compounds according to claim 1 , in which R is acetyl or the group, in which X' is oxygen or sulphur, R'isa 2-chloroethyl radical or straight-chain or branched alkoxy with 1 to 3 carbon atoms and R" is an amino group, or straight-chain or branched alkoxy or alkylamino, each with 1 to 3 carbon atoms.

3. The compound of the formula 0 II Cl-CH2-CH2- - HC5H7-iso ( 1 ) 0-CO-CH.

4. The compound of the formula G1-GH2-CH2. S (2) iso-C^-NH'

5. The compound of the formula

6. The compound of the formula C1-CH0-CH 0 0 CH2-CH2-G1 iso-C^-NH NH-C^-iso

7. The compound of the formula Cl-CH0-CH S S ^CH -CH -C1 -- — - II II <- P-O-P (6) iso-C-^NH NH-C^-iso

8. The compounds according to claim 1 that are hereinbefore specifically disclosed.

9. process for the preparation of an N-isopropyl-2-chloro-ethane-(thiono)-phosphonic acid ester amides according to claim 1 , in which an N-isopropyl-2-chloroethane-(thiono)-phosphonic acid amide halide of the general formula C1-GH -CH9 X P-Hal (II), iso-C^-HN in which X has the meaning stated in claim 1 and Hal is halogen, is reacted with a compound of the eneral formula V R - 0 - Y (in) in which R a the meaning stated in claim 1 and Y i hydrogen or one equivalent of an alkali metal, alkaline earth metal or ammonium.

10. A process according to claim 9, in which Hal is oh .1 orine .

11. A process according to claim 9 or 10, in which 7 is sodium, potassium, calcium or ammonium.

12. A process according to claim 9 or 10, in which Y is hydrogen arid the reaction is effected in the presence of an acid acceptor. 1 · A process according to claim 12, in which the acid acceptor is an alkali metal alcoholate, an alkali metal carbonate, or an aliphatic, aromatic or heterocyclic amine. 14. process according to any of claims 9 to 13» in which the reaction is effected in the presence of a diluent or solvent. 15. A process according to any of claims 9 to 14, in which the reaction is effected at between 0° and 100°C. 16. A process according to claim 15, in which the reaction is effected at between 10° and 70°G. 17. A process according to any of claims 9 to 16, in which the reactants (II) and (III) are employed in equimolar amounts. 18. A process for the preparation of an N-isopropyl-2-chloro-ethane-( thiono)-phosphonic acid amide according to claim 1 in which R is a group of the formula in which Χ' has the same meaning as X, in which, process, an N-isopropyl-2-chloroethane-( thiono)-phos honic acid amide of the formula (II) given in claim 9» is treated, at a temperature of between 0° and 100°C, with a mixture of an acid acceptor, water and an organic solvent. 19. A process according to claim 18, in which the acid-acceptor is pyridine and the organic solvent is methylene chloride . 20. A process for the preparation of a compound according to claim 1 , substantially as hereinbefore described in any one of Examples 1 to 6. 21 o A compound according to claim 1 , whenever- prepared by a process according to any of claims 9 to 20. 22. A plant-growth-regulating composition containing as active ingredient a compound according to any of claims 1 to 8 and 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. 23. A composition according to claim 22 containing from 0.1 to 95?<> of the active compound, by weight. 24. A composition according to claim 23 containing from 0.5 to 90% of the active compound, by weight. 25. A method of regulating the growth of plants which com-prises applying to the plants or a plant habitat a compound according to any of claims 1 to 8 and 21 alone or in the form of a composition containing as active ingredient a compound according to any of claims 1 to 8 and 21 in admixture with a diluent or carrier. 26. A method accordin to claim 2 in which a is used containing from 0.0005 to ?$ of the active compound, by weight. 27. A method according to claim 26 in which a composition is used containing from 0.01 to 0.59» of the active compound, by weight. 28. A method according to claim 25 , 26 or 27 in which the active compound is applied to an area of plant cultivation in an amount of 0.01 to 50 kg per hectare. 29. A method according to claim 28 in which the active compound is applied in an amount of 0.1 to 10 kg per hectare. 30. A method according to any of claims 25 to 29 in which the active compound is one of those hereinbefore mentioned in any of Examples A to C. 31. Plants, the growth of which has been regulated by their being grown in areas in which immediately prior to and/or during the time of the growing a compound according to any of claims 1 to 8 and 21 was applied alone or in admixture with a diluent or carrier.