DE3234610A1 - Benzyl ether derivatives of glycerol, processes for the preparation of these compounds, and plant-growth-regulating agents containing them - Google Patents

Abstract

The invention relates to novel benzyl ether derivatives of glycerol of the general formula <IMAGE> in which one of the substituents Y represents the group of the general formula <IMAGE> and the two other substituents Y are identical or different and in each case represent the group -(CO)n-R3 where R1 represents hydrogen or a C1-C4-alkyl radical, R2 represents an aromatic hydrocarbon radical which is optionally monosubstituted or polysubstituted by C1-C6-alkyl and/or C1-C6-alkoxy and/or optionally substituted phenoxy and/or optionally substituted phenyl and/or halogen and/or the nitro group and/or the trifluoromethyl group, R3 represents hydrogen or an optionally substituted C1-C4-alkyl radical, and n represents 0 or 1, processes for the preparation of these compounds, and plant-growth-regulating agents containing them. The compounds are particularly suitable for controlling the vegetative and generative growth of plants, in particular legumes, preferably soya beans.

Description

BENZYL ETHER DERIVATIVES OF GLYCERINE, PROCESS FOR PRODUCING

PROVISION OF THESE LINKS AND THE EQUIPMENT CONTAINED WITH GROWTH REGULATORY EFFECT FOR PLANTS The invention relates to new benzyl ether derivatives des glycerol, processes for the preparation of these compounds and those containing them Agent with a growth-regulating effect for plants.

Glycerine ethers with biological effects have not yet become known.

The object of the present invention is to create new active ingredients with an advantageous growth-regulating effect for plants.

According to the invention, this object is achieved by an agent which is characterized by a content of at least one compound of the general formula in which one of the substituents Y is the group of the general formula and the two other substituents Y are identical or different and each represent the group - (CO) n - R3, in which R1 is hydrogen or a C1-C4-alkyl radical, R2 is optionally one or more substituted by C1-C6-alkyl and / or C1-C6-alkoxy and / or optionally substituted phenoxy and / or optionally substituted phenyl and / or halogen and / or the nitro group and / or the trifluoromethyl group substituted aromatic hydrocarbon radical, R3 hydrogen or an optionally substituted C1 -C4 alkyl radical and n 0 or represent 1.

The compounds according to the invention are surprisingly suitable to regulate the growth of plants and enrich through their diverse Effects the state of the art in this area.

Since the compounds according to the invention are both qualitative and quantitative Cause changes in plants as well as changes in the metabolism of plants, they are to be classified in the class of plant growth regulators, which are characterized by distinguish the following possible applications.

Inhibition of vegetative growth in woody and herbaceous plants For example, at the edges of the beach, track systems, etc., in order to allow excessive growth prevent. Inhibition of growth in grain to prevent it from being stored or twisted, with cotton to increase the yield.

Influencing the branching of vegetative and generative organs in ornamental or cultivated plants to increase the flower base or in tobacco and Tomato to inhibit side shoots.

Improvement of the fruit quality, for example an increase in the sugar content with sugar cane, sugar beet or fruit, and a more even ripening of the Crop that leads to higher yields.

Increase in resistance to litter, for example against climatic influences, such as cold and drought, but also against phytotoxic ones Influences of chemicals.

Influencing the latex flow in rubber plants.

Formation of parthenocarpic fruits, male sterility and sexual influence are also possible applications.

Control of the germination of seeds or the emergence of buds.

Defoliation or influencing of fruit fall to facilitate harvest.

The compounds according to the invention are particularly suitable for influencing of vegetative and generative growth in some legumes, such as Soy.

The application rates are generally from, depending on the intended use 0.005 to 5 kg of active ingredient / ha, if appropriate, higher application rates can also be used will.

The application time depends on the application goal and the climatic Conditions.

Of the compounds according to the invention, they are characterized by an optimal one growth-regulating effect in particular from those in those cited general formula I Y1 and Y2 are each the same and a hydrogen atom, a C1-C4-alkyl radical or an alkanoyl group with up to 5 carbon atoms, preferably an acetyl or butyryl group, and Y3 an aralkyl group of the general formula II or Y1 and Y3 are each identical and a hydrogen atom, a 9 9 C1-C4-alkyl radical or an alkanoyl group up to 5 carbon material atoms, especially an acetyl or butyryl group and Y2 an aralkyl group of the general Formula II mean.

Compounds according to the invention with an outstanding corresponding effect are in particular those in which R1 is hydrogen or C1-C4-alkyl, preferably Methyl, R2 phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,6-dichlorophenyl, 2,4-dichlorophenyl, 3, 4-dichlorophenyl, 2,4,6-trichlorophenyl, 4-bromophenyl, 2,4-dibromophenyl, 2,6-dibromophenyl, 2,4,6-tribromophenyl, 2-fluorophenyl, 2-chloro-6-fluorophenyl, D-fluorophenyl, 4-fluorophenyl, 2, 4-difluorophenyl, 2 phenyl, 3-methylpnenyl, 4-methyiphenyl, 3, 4-dimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,4-dioxymethylphenyl, 2-phenoxyphenyl, 3-phenoxyphenyl, 2-nitrophenyl or 3-nitrophenyl, R3 hydrogen, C1-C4-alkyl, preferably methyl, ethyl, propyl or chloromethyl and n 0 or 1 represent.

The compounds according to the invention can either be used alone or in a mixture be used with each other or with other active ingredients. If necessary, can Defoliation, plant protection or pesticide as required Purpose to be added.

If a broadening of the spectrum of activity is intended, other biocides can also be added.

For example, mixture partners are suitable as herbicidally effective mixture partners those active ingredients that are described in Weed Abstracts, Vol. 31, 1981, under the title "List of common names and abbreviations employed for currently used herbicides and plants growth regulators are listed in weed abstracts. In addition, neither can phytotoxic agents are added to the herbicides and / or growth regulators can result in a synergistic increase in effectiveness, such as wetting agents, Emulsifiers, solvents and oily additives.

The active compounds according to the invention or mixtures thereof are expedient in the form of preparations such as powders, scattering agents, granulates, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers, respectively Diluents and, if necessary, wetting agents, adhesives, emulsifying agents and / or dispersing agents, applied.

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons such as benzene, toluene, xylene, cyclohexanone, isophorone, Dimethyl sulfoxide, D: methylformamide, furthermore mineral oil fractions.

Mineral earths are suitable as solid carriers, for example Tonsil, Silica gel, talc, kaolin, attaclay, limestone, silica and vegetable products, for example flours.

Examples of surface-active substances are calcium lignosulfonate, Polyoxyethylene-alkylphenol ethers, naphthalene sulfonic acids and their salts, phenol sulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and their salts.

7) the proportion of the active ingredient (s) in the various Preparations can vary within wide limits.

For example, the agents contain about 5 to 95 percent by weight Active ingredients, about 95 to 5 percent by weight liquid or solid carriers as well optionally up to 20 percent by weight of surface-active substances.

The agents can be applied in the usual way, for example with water as a carrier in spray mixtures of about 100 to 1000 Liter / ha. An application of the means in the so-called low-volume and ultra-low-volume method is just as possible as their application in the form of so-called microgranules.

For the preparation of the preparations, for example, the following are used Ingredients used: A. Wettable powder a) 80 percent by weight active ingredient 15 percent by weight Kaolin 5 percent by weight surfactants based on the sodium salt of N-methyl-N-oleyltaurine and the calcium salt of lignin sulfonic acid.

b) 50 percent by weight of active ingredient 40 percent by weight of clay minerals 5 Weight percent cell pitch 5 weight percent surfactants on the base a mixture of the calcium salt of lignin sulfonic acid with alkylphenol polyglycol ether.

c) 20 percent by weight of active ingredient 70 percent by weight of clay minerals 5 Weight percent cell pitch 5 weight percent surfactants on the base a mixture of the calcium salt of lignin sulfonic acid with alkylphenol polyglycol ethers.

d) 5 percent by weight of active ingredient 80 percent by weight of Tonsil 10 percent by weight Cell pitch 5 percent by weight of surface-active substances on the basis of a fatty acid condensation product.

B. Emulsion concentrate 20 percent by weight active ingredient 40 percent by weight Xylene 35 percent by weight dimethyl sulfoxide 5 percent by weight mixture of nonylphenyl polyoxyethylene or calcium dodecyl benzosulfonate.

C. Paste 45 percent by weight active ingredient 5 percent by weight sodium aluminum silicate 15 percent by weight of cetyl polyglycol ether with 8 moles of ethylene oxide 2 percent by weight Spindle oil 10 percent by weight polyethylene glycol 23 parts water.

The new compounds according to the invention can be prepared, for example, by A) compounds of the general formula in which one of the substituents Y 'is the group and the two other substituents YT denote Wasserstori, a) with compounds of the general formula R3 - CO X IV - or b) with compounds of the general formula R3 ZV or c) with compounds of the general formula R3 - CO - O - CO - R3 VI , optionally in the presence of acid-binding agents and / or a catalyst, or B) compounds of the general formula in which one of the substituents Y "is the group and the other two substituents Y "in pairs represent an optionally substituted methylene group mean, optionally in the presence of organic solvents and acidic catalysts such as sulfuric acid, p-toluenesulfonic acid, hydrochloric acid, ammonium chloride, phosphoric acid, silicic acid and acidic ion exchange resins at temperatures from 0 to 100 ° C, preferably from 40 to 80 ° C, hydrolyzed, where R1, R2 and R 3 have the meaning given above and R4 and R5 can each be the same or different and each is hydrogen, a C1-C10-alkyl radical, a substituted C1-C10-alkyl radical, an optionally substituted aryl-C1-C3-alkyl radical, a C- C8-cycloaliphatic hydrocarbon radical an aromatic hydrocarbon radical substituted one or more times by C1-C6-alkyl and / or halogen and / or C1-C6-alkoxy and / or the nitro group and / or the trifluoromethyl group, or R4 and R5 together are a polymethylene group - (CH2 ) m ~ represent, 2 represent a halogen atom, preferably a chlorine atom, and Z represent a halogen atom or the radical R30S020- and m represents the integer 4 and 5 means.

Among the radicals R4 and R5 are the substituted methylene group to be understood as hydrogen, C1-C10-alkyl, for example methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, 2,2-dimethyl-1-propyl, n-pentyl, n-heptyl, n-octyl, n-decyl, substituted C1-C1o-alkyl, for example chloromethyl, bromomethyl, fluoromethyl, Dichloromethyl, trifluoromethyl, trichloromethyl, hydroxymethyl, methoxymethyl, xthoxymethyl, Phenoxymethyl, 4-chlorophenoxymethyl, chloroethyl, bromoethyl, 2-ethoxyethyl, 2-phenoxyethyl, C3-C8-cycloaliphatic hydrocarbons, for example cyclopropyl, cyclopentyl, Cyclohexy, aryl-C1-C3-alkyl, for example benzyl, 2-phenylethyl, aromatic hydrocarbons for example phenyl, 2-chlorophenyl, 5-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 4-methoxyphenyl, 4-nitrophenyl, 2,4-dichlorophenyl.

As starting materials preferred glycerol derivatives VII are both those in which 1) Y112 the remainder and Y "1 and Y113 together each represent an optionally substituted methylene group represent, as well as those in which 2) Y "3 the remainder and Y "1 and Y" 2 together each represent an optionally substituted methylene group.

Even the starting materials of the general formula VII can under certain circumstances, due to their sensitivity to hydrolysis on the carrier material, simulate the claimed effects of the compounds according to the invention.

The reaction partners are converted between 0 ° and 1500 C, in general, however, between room temperature and the reflux temperature of the corresponding Reaction mixture.

The reaction time is 1 to 72 hours.

The reactants are used to synthesize the compounds according to the invention used in approximately equimolar amounts. Suitable reaction media are opposite-the Reactants inert solvents. The choice of solvents or suspending agents depends on the use of the corresponding alkyl or acyl halides as well as dialkyl sulfates and the acid acceptors used. As a solution or Suspending agents may be mentioned, for example, ethers, such as diethyl ether, diisopropyl ether, Tetrahydrofuran, and dioxane, aliphatic and aromatic hydrocarbons, such as Petroleum ether, cyclohexane, hexane, heptane, benzene, toluene and xylene, carboxylic acid nitriles, such as acetonitrile and carboxamides such as dimethylformamide.

Organic bases, such as, for example, are suitable as acid acceptors Triethylamine, N, N-dimethylaniline and pyridine bases or organic bases such as oxides, Hydroxides and carbonates of the alkaline earth and alkali metals. Liquid bases such as pyridine can also be used as solvents.

ALs catalysts for process variant A are onium compounds suitable, such as quaternary ammonium, phosphonium and arsonium compounds as well Sulfonium compounds.

Polyglycol ethers, especially cyclic ones, such as for example 18-crown-6, and tertiary amines such as tributylamine. Preferred Compounds are quaternary ammonium compounds such as benzyltriethylammonium chloride and tetrabutylammonium bromide.

The inventive prepared by the above-mentioned processes Compounds can be isolated from the reaction mixture by the customary methods be, for example, by distilling off the solvent used at normal or reduced pressure, by precipitation with water or by extraction. An increased The degree of purity can usually be determined by purification by column chromatography fractional crystallization can be obtained.

The compounds according to the invention are generally almost discolored and odorless liquids that are sparingly soluble in water, conditionally soluble in aliphatic hydrocarbons such as petroleum ether, hexane, pentane and cyclohexane easily soluble in halogenated hydrocarbons such as chloroform, methylene chloride and carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene and Xylene, ethers, such as diethyl ether, Tetrahydrofuran and dioxane, carboxylic acid nitriles such as acetonitrile, ketones such as acetone, alcohols such as methanol and ethanol, carboxamides, such as dimethylformamide and sulfoxides such as dimethyl sulfoxide, but also colorless and odorless crystalline bodies that are sparingly soluble in aliphatic and aromatic hydrocarbons are moderately to readily soluble in halogenated hydrocarbons such as chloroform and carbon tetrachloride, ketones such as acetone, carboxamides such as dimethylformamide, Sulfoxides, such as dimethyl sulfoxide, carboxylic acid nitriles, such as acetonitrile, lower Alcohols such as methanol, ethanol and water.

The solvents used for recrystallization are in particular water, Methanol, acetonitrile and ethyl acetate.

The following examples explain the preparation of the inventive Benzyl ether derivatives of glycerine.

Example 1 1-0- (2,6-dichlorobenzyl) -glycerol 14.6 g (0.05 mol) (2,2-dimethyl-1,3-dioxolan-4-ylmethyl) - (2,6-dichlorobenzyl) -ether are presented and mixed with 55 ml of 1.5N sulfuric acid with stirring. Then it will be Stirred for 2.5 hours at 900 ° C. and then the reaction mixture overnight Left to stand at room temperature. The solution is then saturated with potassium carbonate and the product extracted with 300 ml of ethyl acetate, the extracts are then added washed twice with 100 ml of water each time, dried over magnesium sulfate, filtered and concentrated in vacuo. Colorless crystals obtained from diisopropyl ether are obtained recrystallized and then at room temperature / 200 Torr to constant weight to be dried.

Axle yield: 9.6 g = 76.4% of theory 62 ° - 64 ° C TLC: mobile phase: Chloroform / ethyl acetate 3: 1 Rf value: 0.34 Analysis: Ber. C 47.83% H 4.82% Cl 28.24 % Found C 47.90% H 4.90% Cl 28.36% Example 2 2,3-Bis-O-methyl-1-0- (2,6-dichlorobenzyl) glycerol 10.0 g (0.04 mol) of 1-0- (2,6-dichlorobenzyl) glycerol, 0.8 g of benzyltriethylammonium chloride and 25.23 g (0.2 mol) of dimethyl sulfate are placed in 40 ml of methylene chloride.

Then 23.4 g (0.585 mol) of sodium hydroxide, dissolved in 29 ml of water, added dropwise to the mixture at about 30 ° C. while cooling. After three hours of stirring at room temperature, the mixture is refluxed for a further hour warmed up.

It is then diluted with 150 ml of water and twice with 150 each time ml of methylene chloride extracted. The washed with water, over magnesium sulfate The dried and filtered extracts are concentrated and the oil that remains dried to constant weight at 400 ° C. under an oil pump vacuum.

Yield: 10.4 g = 93.2% of theory nD20: 1.5175 TLC: mobile phase = Toluene / ethyl acetate 1: 1 Rf value = 0.53 Analysis: Calc. C 51.63% H 5.78% Cl 25.40 % Found C 51.46% H 6.10% Cl 25.45% Example 3 2,3-Bis-O-acetyl-1-O- (2,6-dichlorobenzyl) -glycerol 10.0 g (0.04 mol) of 1-O- (2,6-dichlorobenzyl) -glycerin are added to a mixture of 40 ml of pyridine and 40 ml of acetic anhydride were first stirred for one hour at room temperature and then left to stand overnight. The reaction mixture is mixed with 150 ml of toluene added and the solution evaporated to dryness under a water jet vacuum. Of the A further 150 ml of toluene are added to the residue and the mixture is again concentrated in vacuo. The remaining oil is taken up in portions with 300 ml of ethyl acetate. the washed with water, dried over magnesium sulfate and filtered ethyl acetate extracts are evaporated and the remaining oil to constant weight under an oil pump vacuum dried.

Yield: 12.5 g = 93.3% of theory nD20: 1.5129 TLC: mobile phase: Toluene / ethyl acetate 1: 1 Rf value: 0.56 Analysis: Calc. C 50.16% H 4.81% Cl 21.16 % Found C 50.16% H 4.18% Cl 21.12% In an analogous way can produce the other compounds according to the invention.

Example Name Physical constant 4 1-0-Benzylglycerin nD20: 1.5287 5 1-O- (2,4-dichlorobenzyl) -glycerin M.p .: 58-600 C 6 1-0- (2-chlorobenzyl) -glycerin nD20: 1.5428 7 1-0- (2-methylbenzyl) -glycerin nD20: 1.5302 8 2-0- (2,6-dichlorobenzyl) -glycerin nD20: 1.5570 9 2-0- (2,4-dichlorobenzyl) -glycerin M.p .: 89-910 C 10 2-0- (2-chlorobenzyl) -glycerin M.p .: 74-750 C 11 2-0- (2-methylbenzyl) -glycerol M.p .: 58-600 C 12 1-0- (2-chloro-6-fluorobenzyl) - M.p .: 54-550 C -glycerol 13 1,2-bis-O- (acetyl) -3-O- (2-nD20: 1.4947 chloro-6-fluorobenzyl ) -glycerin 14 3-O (2-chloro-6-fluorobenzyl) n 20: 1.4930 -7,2-bls-0- (methyl) -glycerin As starting compounds of the general formula VII, which are usually known from the literature or can be synthesized by methods known per se, include called the following: Name Physical constant (2,2-dimethyl-1,3-dioxolan-4-ylmethyl) - (2,6-dichlorobenzyl) -ether nD20: 1,5212 (2,2-dimethyl-1,3-dioxolan-4-ylmethyl) - (2,4-dichlorobenzyl) ether nD20: 1.5195 (2,2-Dimethyl-1,3-dioxolan-4-ylmethyl) - (2-chlorobenzyl) ether nD20: 1.5074 (2,2-Dimethyl-1,3-dioxolan-4-ylmethyl) - (2-methylbenzyl) -ether nD20: 1,4987 (2-phenyl-1,3-dioxan-5-yl) -benzylether M.p .: 62-640 C (2,6-dichlorobenzyl) - (2-phenyl-1,3-dioxan-5-yl) ether. M.p .: 85-87 ° C (2,4-dichlorobenzyl) - (2-phenyl-1,3-dioxan-5-yl) -ether m.p .: 110-111 C (2-chlorobenzyl) - (2-phenyl-1,3-dioxane -5-yl) ether Mp .: 90-92 ° C (2-chloro-6-fluorobenzyl) - (2,2-dimethyl-1,3-dioxolan-4-yl-methyl) -ether nD20: 1.4949 (2,2-dimethyl-1,3-dioxolan-4-ylmethyl) - (2,4,6-tribromobenzyl) ether Melting point: 57 - 57.5 ° C The following examples explain the possible applications of the compounds according to the invention.

B e 1 s p i e 1 15 Increase in yields of soybeans Soybeans were used in Post-emergence greenhouse with an aqueous emulsion of the test Connections injected.

The application rate was 0.8 kg active ingredient / ha. 4 weeks after the injection the number of flowers and pods compared to the untreated control determined.

The compounds according to the invention brought about a significant increase of the flower and socket necks.

The plants were also compressed and stood out an intense dark green color.

Table according to the invention flower and pod approach connections in % of control 1-0- (2,6-dichlorobenzyl) -glycerin 162 1-O- (2,4-dichlorobenzyl) -glycerin 136 1-0- (2-methylbenzyl) -glycerin 104 2-0- (2,6-dichlorobenzyl) -glycerin 171 2-0- (2,4-dichlorobenzyl) -glycerin 150 B e 1 s p 1 e 1 16 Inhibits growth and promotes branching in the case of beans French beans were sown in the soil into which the powdery preparations of the compounds according to the invention incorporated in concentrations of 5, 25 and 125 ppm was. After one month of greenhouse cultivation, the percentage growth inhibition and the degree of branching of the plants was determined. From the table are the results of the experiment.

Here mean 0 = no promotion of the branch + = weak promotion of branching +++ = very intensive promotion of branching The findings show that the compounds according to the invention have an intensive growth-inhibiting and branching-promoting effect Make an impact.

In addition, depending on the application rate, the flowers were set on the plants clearly increased.

Table Concentration according to the invention, growth inhibition, branching, compounds (ppm)% 1-O- (2,6-dichlorobenzyl) -glycerin 5 78 +++ 25 83 125 87 1-0- (2,4-dichlorobenzyl) -glycerin 5 32 + 25 27 + 125 74 1-0- (2-methylbenzyl) -glycerin 5 0 0 25 19 0 125 23 + 2-O- (2,6-dichlorobenzylglycerin 5 78 25 82 125 82 +++ 2-O- (2-chlorobenzyl) -glycerol 5 0 0 25 0 0 125 13 +

Claims (1)

PATENT CLAIMS 1. Benzyl ether derivatives of glycerol of the general formula in which one of the substituents Y represents the group of the general formula and the two other substituents Y are identical or different and each represent the group (CO) n - R3, in which hydrogen or a C1-C4-alkyl radical, R2 is optionally one or more substituted by C1-C6-alkyl and / or C1 -C6-alkoxy and / or optionally substituted phenoxy and / or optionally substituted phenyl and / or halogen and / or the nitro group and / or the trifluoromethyl group-substituted aromatic hydrocarbon radical, R3 hydrogen or an optionally substituted C1-C4-alkyl radical and n 0 or 1 represent. 2. Benzyl ether derivatives of glycerol according to claim 1, wherein R1 is hydrogen or C1-C4-alkyl, preferably methyl, R2-phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,6-dichlorophenyl, 2,4-dichlorophenyl, 3, 4-dichlorophenyl, 2,4,6-trichlorophenyl, 4-bromophenyl, 2,4-di- bromophenyl, 2,6-dibromophenyl, 2,4,6-tribromophenyl, 2-chloro-6-fluorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 3,4-dimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-mehoxyphenyl, 3,4-dioxymethylphenyl, 2-phenoxyphenyl, 3-phenoxyphenyl, 2-nitrophenyl or 3-nitrophenyl, R3 hydrogen, C1-C4-alkyl, preferably methyl, Ethyl, propyl or chloromethyl and n represent 0 or 1. 3.1-0- (2,6-dichlorobenzyl) -glycerin 4. 2,3-bis-0-ethyl-1-0- (2,6-dichlorobenzyl) -glycerin 5. 2,3-bis-O- acetyl-1-0- (2,6-dichlorobenzyl) -glycerin 6. 1-0-benzylglycerin 7. 1-0- (2,4-dichlorobenzyl) -glycerin 8. 1-0- (2-chlorobenzyl) -glycerin 9.1-0- (2-methylbenzyl) -glycerin 10. 2-0- (2,6-dichlorobenzyl) -glycerin 11. 2-0- (2,4-dichlorobenzyl) -glycerin 12. 2-0- ( 2-chlorobenzyl) -glycerin 13. 2-0- (2-methylbenzyl) -glycerin 14. 1-0- (2-chloro-6-fluorobenzyl) -glycerin 15. 1,2-bis-O- (acetyl) - 3-O- (2-chloro-6-fluorobenzyl) -glycerol 16. 3-0- (2-chloro-6-fluorobenzyl) -1,2-bis-O-methyl-glycerol 17. Process for the preparation of benzyl ether derivatives of Glycerine according to Claims 1 to 16, characterized in that A) compounds of the general formula in which one of the substituents Y 'is the group and the two other substituents Y 'are hydrogen, a) with compounds of the general formula R3 - CO X IV or b) with compounds of the general formula R3 -ZV or c) with compounds of the general formula - CO - O - CO - R3 VI , optionally in the presence of acid-binding agents and / or a catalyst, or B) compounds of the general formula in which one of the substituents Y "is the group and the other two substituents Y "in pairs represent an optionally substituted methylene group mean, optionally in the presence of organic solvents and acidic catalysts such as sulfuric acid, p-toluenesulfonic acid, hydrochloric acid, ammonium chloride, phosphoric acid, silicic acid and acidic ion exchange resins at temperatures from 0 to 100 ° C, preferably from 40 to 80 ° C, hydrolyzed, where R1, R2 and R have the meaning given above and 1 2 3 R4 and R5 can each be identical or different and are each hydrogen, a C1-C10-alkyl radical, a substituted C1-C10-alkyl radical, an optionally substituted aryl-C1-C3-alkyl radical, a C3-C8-cycloaliphatic hydrocarbon radical, an aromatic hydrocarbon radical substituted one or more times by C1-C6-alkyl and / or halogen and / or C1-C6-alkoxy and / or the nitro group and / or the trifluoromethyl group, or R4 and R5 together Represent a polymethylene group (CH), X represent a halogen atom, preferably a chlorine atom, and Z represent a halogen atom or the radical R3OS020- and m represents the integer 4 u nd means 5. 18. Agents with growth-regulating effect for plants, labeled by a content of at least one compound according to claims 1 to 16. 19. Agents with a growth-regulating effect for plants according to Claim 18 mixed with carriers and / or auxiliaries. 20. Means according to claims 18 and 19 for influencing the vegetative and generative growth of plants, especially in legumes, preferably Soy. 21. Means with growth-regulating effect for plants according to Claim 18, produced by the method according to Claim 17.