DE2149680B2 - 2-HALOGENEETHYL-ORGANOOXY-SILANES, THEIR PRODUCTION AND AGENTS FOR REGULATING PLANT GROWTH - Google Patents

Description

X-CH ₂ -CH ₂ -Si- (O-CO-R ₄ ), (III)

where Y 'signifies chlorine or the radical -OCOR ₄ , gradually exchanging one, two or all three radicals - OCOR ₄ for radicals of alcohols P, OH or R ₂ OH or R ₃ OH.

3. Agent for regulating plant growth, characterized in that it is used as an active ingredient a 2-haloethyl-tri-organonxysilane or Contains 2-haloethyl-chloro-diorganooxysilane.

The invention relates to new 7-haloethyl-organooxysilanes and means for regulating plant growth to improve yield and facilitate harvesting agricultural, forestry and horticultural products and processes for the production of new silanes.

It has been found that the agents according to the invention and their active ingredients are surprisingly beneficial Effect on the growth and differentiation of above and below ground parts of plants and - Exercise tissue. They are the well-known plant growth regulator 2-chloroethane-phosphonic acids, which is an active ingredient in its mode of action. consider and ask in some ways thus a valuable addition to technology.

The new means of regulating the plant / cn-

wax rims are characterized by the fact that they as active ingredient a 2-Halogcnälhyl organooxy-silane formula

OR

Hal -CH, -CH, -Si -O-R

'I γ

where X is chlorine or bromine,

a) with a total of 2 or 3 equivalents of different alcohols or an identical alcohol R ₁ OH and / or R ₂ OH and optionally R ₃ OH or

b) with a total of 2 or 3 equivalents of the same or different carboxylic acids Ri contain - COOH or their anhydrides, in which Y is chlorine or - OR and R represents organic residues.

These 2-haloethyl-organooxy-silanes affect the growth of above and below ground parts of plants in different ways and have in the Usual application concentrations have a low toxicity to warm blooded animals. The active ingredients call into this Concentrations also do not result in any morphological changes or damage that the entering into of the plant. The compounds are not mutagenic. Their effect is one of those herbicidal active ingredient and a fertilizer. Rather, the effect corresponds to the. dk can be observed when ethylene is applied to different parts of the plant. It is known dai. ' also the plant itself in different stages of development to different degrees of ether produced, especially before and during the ripening process of the fruit and at the end of the fruit Vegetation period with the fruit and leaf detachment Since the influence of ripening, the fruit detachment and the leaf detachment by chemical substances in the fruit. Citrus fruit, pineapple and cotton cultivation The greatest economic importance was sought, the development of the plant with ether separating agents from the outside positive / u be

: influences. So are different in the meantime Jubsianzkiassen became known with which individual such effects can be achieved.

Such known compounds are either relatively unstable under weather conditions because they are very sensitive to hydrolysis or phytotoxic. In South African patent 68/1036 are / i-haloethylphosphonic acid derivatives than that Plant growth regulating agents described. These compounds decompose into and on the plant with the release of ethylene and are therefore similar to ethylene in terms of action and breadth of action. Due to their very poor stability, these phosphonic acids and their derivatives are capable but not enough to meet the demands placed on them. Since they only work in an acidic environment, more precisely in a pH range below:>, are stable, must the active ingredient concentrates can be stabilized by adding acids. This acid additive however, restricts the scope of these Wj-Icstoffe with regard to phytotoxic effects. In addition, the storage is more sensitive this way Active ingredient concentrations associated with difficulties. Other disadvantages of the 2-Chloräthanphosphonsüuie are not only corrosive but also have good water solubility, which causes it to appear everywhere in the sap flow of the plants and its effect not only at the desired location (fruits), but z. B in the form of uncomfortable water overflow makes the whole plant noticeable, so should not be used specifically for fruit abscission alone can, and also has too long a permanent effect

Certain halogen alkyl methylsilanes are also known as herbicidal active ingredients (cf. USÄ. Patcnlschriften 33 90976. 33 90977 and \). K. L ca s u re et al. J. Med. Chem, 9,949 [1966]).

Some low molecular weight; -chloroethyl-tris (alkoxy) -silanes and / j'-chloroethyl-acetoxy-dialkoxy or , '/ - Chloräthyl-diacetoxy-afkoxy-silanes are already known (F.W. Boye et al., J. Org. Chem. 16, 391 [1951] and 17, 1386 [1952]), but are plant growth regulators Properties of these compounds not previously described.

The invention relates to new active ingredients 2-Halogenäthyl-organooxy-silanes containing agents which, in the various stages of plant development, stimulate or retard plant growth act and do not have the disadvantages of 2-chloroethylphosphonic acid. Due to the These agents contain very good stability of these active ingredients in addition to the usual carriers, distribution agents, Light and oxidation stabilizers do not have a stabilizing acid additive and are therefore applicable without restriction. The new means intervene in the physiological processes of phance development a and can be used for various purposes that are related with the increase in yield, the easing of the harvest and the saving of labor in the case of cultural technology Measures. The various effects of these active ingredients depend essentially on the Time of application, based on the development stage of the seed or the plant, as well as of the concentrations used.

By suitable treatment with the agents according to the invention, the ripening process can be achieved Accelerate plants and do a better one.

More uniform maturation of fruits or others Achieve parts of the harvest, which is more economical with various types of fruit and other crops Meaning is.

It has been found that the proposed 7-haloethyl-organooxy-silanes in particular for Regulation of fruit fall (fruit abscission) is ideal. The agents according to the invention and active ingredients are for the abscission of olives

ίο in terms of effect that known for fruit abscission Commercial product 2-chloroethyl-phosphonic acid clearly superior, as shown in extensive comparative experiments to have. The harvesting of fruits is traditionally done by hand. In the course of Rationalization in agriculture has suggested other methods of harvesting egg fruits. A wide variety of mechanical devices have been developed for this purpose. Sole marriage mechanical devices, however, usually damage the plants and the harvest gui. It was found, that fruits either with no or only little mechanical support! to waste brought and can therefore be harvested more economically if the trees. Bushcr. Perennials be treated with the active ingredients according to the invention before the fruit is ripe

The promotion of fruit fall can also be used in this way that by early application of the active ingredients a chemical thinning of the young Fruit is obtained. This is desirable in the case of too strong, natural-n-! Fruit set, as z. B. at Apples. Peaches or citrus fruits often occurs. With the new means, the vegelathe plant growth and the germination capacity is influenced Flower formation, fruit development and the formation of separating tissues are promoted. aside from that the Slülzgevebe dt-r stem was strengthened in the treated plants. The training undesirable Stingy instincts in various types of plants, such as B. with tobacco and azaleas, becomes very strongly reduced, also the vegetative growth of vines is inhibited. The new connections work also promotes secretion, e.g. B the latex flow is promoted at Hevea brasiliensis; an effect that is great has economic importance. As experiments showed, the rooting of seedlings and cuttings as well as tuber formation in potatoes. In addition, the budding is more dormant Rhizomes at the same time, which is particularly important with different perennial weeds such as couch grass. Johnsongrass and Cypcrus, which can then be easily destroyed or contained with herbicides. the The ability of seeds to germinate is encouraged at lower concentrations and prevented at higher concentrations. As well as either effect is of economic importance. With many ornamental and cultivated plants It is possible to control the flowering date and the number of flowers. This is the case with pineapples Effect plays a particularly important role. If all plants bloom at the same time, harvesting can take place within a comparatively short time. There is a shift in pumpkin and other crops the flower sex differentiation in favor of dci female flowers. The influence of the flowering differentiation can in practice have a positive effect. liell /. B. as an aid in hybridizations in de Seed breeding or to increase yield, e.g. B. linden in freestyle bisuewächscn use.

By influencing the bloom formation, the bloom history and vegetative growth, the active ingredients used according to the invention can Significantly increase the harvest yield of plants (e.g. fruits, seeds, leaves).

The sprout and root growth can be controlled by the active ingredients in a koiizentretions-dependent manner be regulated. It is thus possible to inhibit the growth of plants. Of economic interest is here z. B. the attenuation of grass growth * n roadsides and roadsides or on lawns, because this allows the frequency of grass clippings to be reduced.

The seed germination, the sprouting of buds and rhizomes and the formation of side shoots can be promoted by the named active ingredients depending on the concentration used or be inhibited. Seed germination and the sprouting of dormant rhizomes can contribute to this Weeds are promoted, which facilitates the destruction of these weeds with herbicides. It but on the other hand, the undesirable development of stingy instincts in decapitated tobacco plants be prevented.

The possibility of using the agents according to the invention for certain plants should also be emphasized trigger the leaf fall. The harvest of cotton plants is made much easier if you previously defoliated the cotton plants by means of these compounds. For plants that are transplanted the transpiration can be reduced by defoliation.

Tests also showed that fruit and blossom thinning occurs in fruit trees. Farther are z. B. with oranges, melons, apricots, peaches, tomatoes. Bananas, blueberries, figs, Coffee, pepper and pineapple accelerate and improve fruit ripening and coloration. as well the ripening of tobacco leaves is accelerated and improved. By training fren- <o With tissue, the fruit detachment is made much easier. Has great economic significance this for mechanical harvesting, e.g. B. of citrus fruits, of olives. Stone fruit or pome fruit or Berries or subtropical fruits. By suitable application of the above substances, different crops, such as cotton, green beans, green peas, ornamental shrubs and young plants Defoliation can be achieved.

The extent and nature of the effect depend on various factors, in particular Application time in relation to the stage of development of the plant and the application concentration. However, these factors in turn differ depending on the type of plant and the desired effect. For example, lawns will be treated throughout the growing season; Ornamental plants, in which, for example, the intensity and number of flowers should be increased before training the flowers; Plants whose fruits are used respectively. be utilized in a corresponding manner Distance in front of the horn. The active ingredients are applied in the form of solid or liquid agents on above-ground parts of plants as well as in the ground or on the ground. Isl preferred Application to the above-ground parts of the plant, for which solutions or aqueous dispersions are on best suited. For the treatment of the wax substrate In addition to solutions and dispersions, there are also dusts, granulates and grit suitable.

The essential promotion of the detachment of citrus fruits and bean leaves with according to the invention Means was determined by the following experiments:

The active ingredients are applied to branches with good fruit treatment various orange trees as solutions in concentrations of 0.2% and 0.4%. After 14 ropes, the tests were carried out according to the method described by W. C. W i 1 s ο η and CH. Hendershott developed Method (Proc. Am. Soc. Hort. Sc. 90, 123 to 129 [1967]) evaluated. The for the Detachment of a fruit determined the force to be expended in kilograms.

The exact experimental methodology was as follows:

On orange trees of a certain variety, individual branches with at least 15 to 20 ripe fruits were found carried, injected with an agent of the two active ingredient concentrations 0.4 and 0.2%. Seven days after the application, the picking force to be used was determined for ten fruits treated in the same way determined with the help of a spring balance and the mean value formed from the ten measured data.

Active ingredient Conc Force in tration Kilograms 2-chloroethyl-tris- 0.2% 4.5 (alhoxy) silane 0.4% 1.5 2-chloroethyltris- 0.2% 3.7 (octyloxy) -siian 0.4% *) 2-chloroethyl-tris- 0.2% *) (benzoxy) silane 0.4% *) 2-chloroethyl-tris- 0.2% 4.7 (dodecyloxy) -sihin 0.4% 1.1 control 8.6

*) The rumors hanging on the tree let m;: 'i se easily assume that no measurement could be made.

Equally good and significant values were obtained with With tcln. which contained the following compounds, he aims:

2-chloroethyl-iris- (2'-chloroethoxy) -silane, 2-chloro-ethyl-iris- [butenyl- (2 ') - oxy] -silane, 2-chloroethyl-tris- [propenyl- (2 ') -oxy] -silane. 2-chloroethyl-tris- [3'-chloro-butenyl- (2 ') - oxy] -silane.

2-chloroethyl-tris- (octadecyloxy) -silane. 2-chloroethyl tris [butynyl (2 ') oxy] silane. 2-chloroethyl iris [hexynyl (3 ') oxy] silane. 2-chloroethyl-tris- (6'-chlorohycxyloxy) -silane. 2-chloroethyl-tris- (4'-methoxy-benzoxy) -silar .. 2-chloroethyl-tris- (2'.4'-dichlorobenzoxy * - i ¹ ,: i: T. 2-chloroethyl-tris - (4'-chlorbcn7.oxy) -sii; .n.

On bean leaf segments it was observed that leaf abscission facilitated by the formation of Treni tissue b / w. is promoted. segment a solution of 0.002% active ingredient was dipped from bean leaves of the »Tempo« variety and pr Active ingredient per 4 to 8 segments during 6 thaws unli controlled conditions in the active ingredient dissolving.

3.5 rcsp. 6 days after the start of treatment, the Λη / ahl of abscesses that have taken place (= intersection of the stem at the leaf-roped abscission zone). The evaluation was carried out according to a grading system from I to 9. where grade 9 = 0 and grade 1 = 8 corresponds to absenteeism.

Active ingredient

2-PromathyllHs- (benzoxy) -silane

2-chloroethyl-iris- (4'-chlorobenzoxy) -silane
2-chloroethyl-tris (octadccyloxy) -silane

2-Bromoethyl-iris- [butenyl- (2 ') - oxy] -silane
2-chloroethyl-tris- (4'-methoxyphynoxy) -silane

2-chloroethyl-tris- (carbobutoxymcthoxy) -silane

Means the following compounds
educate:

2-bromoethyl-tris- (ethoxy) -silane.

2-bromoethyl-tris- (hydroxyloxy) -silane.

2-bromoethyl-tris- (4'-chlorobenzoxy) -silane.

2-bromoethyl-tris- (octadecyloxy) -silane.

2-BromoäthyI-iris- [propynyl- (2 ') - oxy] -siyan.

2-chloroethyl-tris- [propynyl- (2 ') -oxyl] -silane.

2-chloroethyl-tris- (octyloxy) -silane,

2-chloroethyl-tris (benzoxy) -silane.

2-chlorothy! -Tris- (r-carbäthoxyüthyloxy) -silane.

2-chloroethyl-tris- [3'-chlorobutyl- (2 ') - oxy] -

silane,

2-chloroethyl tris [butenyl (2 ') oxy] silane.
2-chloroethyl-tris- [propenyl- {2 ') - oxy] -silane.
2-chloroethyl tris [butynyl (2 ') oxy] silane.
2-chloroethyl-tris- [3 \ 7'-dimethyloctenyl-

(7 ') - oxy] silane,

2-chloroethyl-tris- (4'-methoxybenzoxy) -silane,
2-chloroethyl-tris- [hexynyl- <3 ') - oxy] -silane.
2-chloroethyl (benzyloxy-diacetyloxy) -silane,
2-chloroethyl (dioctyloxy-acetyloxy) -silane.

The acceleration of life was observed on tomato plants proven in the following way:

Tomato plants of the Fournaisc variety were grown outdoors under plastic sheeting. After reaching When the plants reached a height of 1.5 m, the tip of the shoot was cut off. As the first If fruits turned reddish in color, the plants were treated with aqueous preparations from emulsion concentrates of the active ingredients mentioned below. In each case 4 plants were given 1.5 l of spray mixture treated, the active ingredient contained in the broth having a concentration of 2000 ppm, respectively. 4000 ppm (ppm means parts of active ingredient per million parts of broth). 10, 14 and 17 days after application the ripe fruits of the 3 bottom umbels were harvested. The sums of the earnings figures obtained in this way are summarized in the following table:

Active ingredient ΛιιΓ- Yield on tires Wall- l ^r smell from ί behind mcngc Notes Bonilur (ppm I weight % the Evaluation according to in kilos GesaiTit- 6 ropes ^l0
I 2 gram erle 2-chloroethyl-tris- 2000 4.05 61.2 I 1 1 (octyloxy) silane 4000 5.76 71.5 2-chloroethyl-tris- 2000 5.66 73.7 1 1 1 (benzyloxy) silane 4000 6.26 75.9 2-chloroethyl-tris- 2000 5.92 85.2 I 1 1 (3'-chloro- 4000 6.50 84.3 bulenyl- (2 ^r ) -oxy) -silars 111 2-chloroethyl-tris- 2000 5.03 63.4 (butenyl- (2 ') -oxy) -silane 4000 6.06 75.3 1 1 1 2-chloroithyl-t ris- 2000 5.50 70.6 (4'-methoxy-benzyloxy) - 4000 7.30 87.7 1 1 1 25 silane 2-chloroethyl-tris- 2000 3.37 62.9 (4'-chlorobenzyloxy) - 4000 6.80 82.4 silane : Values were with 2-chloroethyl-tris- 2000 5.32 77.7 indications contained. 30th (hexynyl- (3 ') -oxy) -silane 4000 5.94 85.2 Untreated control 3.41 52.0

The resin flow, which can be related to the latex release from rubber trees, was stimulated on plum trees in the following way:

Bark segments were cut out of branches of 12-year-old plum trees (Prumus domestica). A 10% solution of active ingredient (active ingredient: xylene added) was added below and above these incisions Castor oil = 1: 2: 7) on the branch surface of the intact Trees applizicrt. Each treatment was repeated on 4 different trees. 4 weeks after application the expelled resin was removed and weighed. The following table gives average values in grams of resin per treated branch.

Active ingredient

Amount of resin in
Gram

2-Bromoethyl-tris (ethoxy) -silane 0.37

2-chloroethyl-tris (4'-methoxyphenoxy) - 1.81
silane

2-chloroethyl-tris (propynyl- (2 ') - oxy) -silane 0.53

2-chloroethyl-tris (4'-chlorobenzyloxy) -silane 0.52

2-chloroethyl-tris (hexinyI- (3 ') - oxy) -silane 0.85

Control (untreated) 0

The preparation of the agents according to the invention takes place in a manner known per se by intimate Mixing and grinding of active ingredients of the general formula 1 with suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active ingredients.

«J9 521M71

Active ingredient concentration dispersible in water, i.e. Wettable powder, pastes and emulsion concentrates are active ingredient concentrates that can be adjusted to any desired concentration with water can be diluted. They consist of active ingredient, carrier, optionally stabilizing the active ingredient Additives, surface-active substances and anti-foaming agents and, if necessary, solvents. The active ingredient concentration in these agents is 0.5 to 80%.

The wettable powders and pastes are obtained by the active ingredients with the usual dispersants and the usual pulverulent carriers mixed and ground in suitable devices until homogeneous

These mixtures can also contain additives stabilizing the active substance and / or nonionic, anionic active substances and kationcnaktivi: substances are added, which, for example, improve the adhesive strength of the active ingredients on plants and plant parts (adhesive and adhesives) and / or ensure better wettability (wetting agents). Adhesives can be used for example the following in question:

Olein-lime mixture, cellulose derivatives (methyl cellulose, Carboxymethyl cellulose), hydroxyethylene glycol ethers of mono- and dialkylphenols, ligninsulphonic acid, their alkali and alkaline earth salts, polyethyleneglycol ethers (Carbowaxe). Fcttalcohol polyglycol ether, condensation products of ethylene oxide. Propylene oxide. Polyvinyl pyrrolidones, polyvinyl alcohols. Urea formaldehyde condensation products and latex products. The active ingredients are mixed with the additives listed above, ground, sieved and happens that at the wettable powders have a particle size of 0.02 to 0.04 for the solid part and 0.03 mm for the pastes does not exceed.

For the production of emulsion concentrates and pastes, dispersants such as those in the in the previous sections, common organic solvents and water were used.

The solvents have to be practically odorless, not phytotoxic and have no effect on the active ingredients be inert.

The agents according to the invention can also be used in the form of solutions. For this becomes the active ingredient or are several active ingredients of general formula 1 in suitable organic Solvents, solvent mixtures or water. Aliphatic solvents can be used as organic solvents and aromatic hydrocarbons, their thlorinated derivatives, alkylnaphthalenes, mineral oils Can be used alone or as a mixture with one another. The solutions are intended to contain the active ingredients a concentration range from 1 to 20%.

The solid processing forms such as dusts, grit and granulates contain solid carriers, as listed above, and optionally additives stabilizing the active ingredient. The grain size of the carrier materials is expediently up to about 0.1 mm for dusts and up to about 0.1 mm for grit about 0.075 to 0.2 mm and for granules f), 2 mm or more. The active ingredient concentrations In the solid forms of work-up, this is 0.5 to «0%.

All listed active ingredient concentrates can also Contain light stabilizers and antioxidants.

granules

40

45 The following substances are used to produce 5% granules:

5 parts of 2-chloroethyl-iris- (2'-chloro-ethoxy) -silane. 0.25 part epichlorohydrin.
0.25 part of cetyl polyglycol ether. 3.50 parts of polyethylene glycol ("Carbowax"). 91 parts of kaolin (grain size 0.2 to 0.8 mm).

The active substance is mixed with epichlorohydrin and then dissolved with 6 parts of acetone polyethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is on kaolin sprayed on and then the acetone evaporated in vacuo.

Wettable powder

For the production of (a) 40% and (b) 50%, (c) 25% and (d) a 10% wettable powder the following components are used:

(a) 40 parts of 2-chloroethyl-tris (octyloxy) -silane,

5 parts of lignin sulfonic acid sodium salt. 1 part dibutyl naphthalenesulfonic acid

Sodium salt.
54 parts of silica.

(b) 50 parts of 2-chloroethyl-tris (dodecyIoxy) -silane.

5 parts of alkylarylsulfonate ("Tinovetin B" l.

10 parts calcium lignosulfonate.

1 part champagne-chalk-hydroxyethyl-

cellulose mixture (1: 1).

20 parts of silica,

14 parts of kaolin.

(c) 25 parts of 2-chloroethyl-tris- (4'-methoxy-

benzoxy) silane,

5 parts of oleyl methyl tauride Na salt. 2.5 parts of naphthalenesulfonic acid formaldehyde

Condensate,

0.5 parts of carboxymethyl cellulose, 5 parts of neutral potassium aluminum silical. 62 parts of kaolin.

(d) 10 parts of 2-chloroethyl-tris- (4'-chloro-benzoxy) -

silane,

3 parts mixture of the sodium salts of saturated alcohol sulfates,

5 parts of naphthalenesulfonic acid formaldehyde

Condensate,
82 parts of kaolin.

The active ingredients are intimately mixed with the additives in suitable mixers and mixed with the appropriate Grind mills and rollers. This gives wettable powders which, with water, form suspensions Dilute to any desired concentration. Such suspensions find z. B. Application for removing unwanted stinging shoots, for tillering lawns and for rooting Seedlings and cuttings.

Emulsion concentrate

For the production of 25% emulsion concentrates

(a) 25 Parts 2-Chlorälhy! -Tns- (ben / oxy) -silane, 5 Parts Mixture of nonylphenol polyoxy- ethylen, and calcium dodccylbenzene sulfonate. 70 Parts Xylene. (St. 25 Parts 2-chloroethyl-tris- (ethoxy) -silane, 10 Parts Mixture of nonylphenol polyoxy- ethylene and calcium dodecylbenzene sulfonate. 65 Parts Cyclohexanone

can form a heterocyclic system, where then Y must represent a remainder - OR.

The invention also relates to these new compounds of formula 1 and processes for their preparation.

The production of the new 2-haloethyl-organooxy-silane of formula 1 is carried out according to the invention. by adding a 2-haloithyl-trichlorosilane in a manner known per se of formula II

mixed together. This concentrate can be mixed with water to form emulsions at suitable concentrations be diluted. Such emulsions are suitable for thinning flowers and fruits, for accelerated thinning Ripening of fruits and to promote fruit and leaf detachment.

Individual 2-haloethyl-organooxy-silanes are already described above (cf. F. W. B ο y e et al.).

Among the 2-HalogenäthyI-organooxy-silanes, new and preferred active ingredients are those which of Formula 1

X-CH ₂ -CH ₂ -Si (Cl) _-1

wherein X is chlorine or bromine.

O-R ₁

X-CH ₂ -CH ₂ -Si-OR ₂
Y

a) with a total of 2 or 3 equivalents of different alcohols or an identical alcohol R ₁ OH and / or R ₂ OH and optionally R ₃ OH or

b) with a total of 2 or 3 equivalents of the same or different carboxylic acids R ₄ - COOH or their anhydrides

and, if desired, in the silane of the formula III thus obtained

X-CH ₂ -CH ₂ -Si- (O-CO-R ₄ I ₂
Y '

(111)

correspond to where X is chlorine or bromine. Y is chlorine or a radical —OR ₃ , R ₁ , R ₂ and R—, independently of one another unsubstituted alkyl radicals each having 6 to 18 carbon atoms, by chlorine. C _{1 -C 8} alkoxy, C _{1 -C 8} alkyithio. C ₃ -C "alkenyloxy. Phenoxy, phenyl. Cj-C ^ cycloalkyl. Cyano. C _{1 -C R} alkoxy carbonyl. Tetrahydropyranyl. Tetrahydrofuranyl. Thicnyl, dioxanyl or dioxolanyl substituted C _{1 -C 18} -alkyl radicals. CyCtt-Alkenyk Chloralkenyl or Phcnylalkenylreste. _{C 1} -C ₆ alkynyl radicals, C ₃ to C ₁₂ cycloalkyl and cycloalkenyl radicals, possibly one or more times by chlorine or bromine, C 1 -C 4 alk) -I, C _r C ₄ alkoxy, C.-Q- Alkylthio, C _{1 -C 8} alkoxy, QQ-alkoxycarbonyl, formyl or cyano substituted phenyl radicals, optionally benzyl radicals substituted one or more times by chlorine, C _{1 -C 8} alkyl or C _{1 -C 8} alkoxy, or at least one of the radicals R ₁ to R 3 mean a radical —CO — R ₄ , in which each R _{4 has the} same meanings as given under R ₁ to R 3, R _{4 is} additionally also a five- or six-membered heterocyclic-aromatic ring or by a Oxognippe, alkyl radical substituted by methoxyphenyl or dichlorophenoxy or alkenyl radical substituted by chlorophenyl, dichlorophenyl and methoxyphenyl can be embodied, but the radicals R ₁ to R 3 can also represent lower alkyl groups, if X is bromine, and finally R ₁ and R 2, too in the form - COR ₄ , along with those associated with them

O
/
Si group

wherein Y 'signifies chlorine or the radical - OCOR _4.

gradually replaces one, two or all three radicals - OCOR ₄ for radicals of alcohols R ₁ OH or R ₂ OH or R., * OH.

If X in the starting material of the formula 11 is bromine, low molecular weight alkanols can also be used to replace the radicals —O — CO — R ₄ .

Since in the implementation according to the invention, the exchange of the 3 chlorine atoms of the starting materials of the formula II takes place in stages, intermediate products, namely dichlorosilanes and monochlorosilanes, can be used. isolated during synthesis or as impurities from the crude end product.

Incidentally, the monochlorosilanes (Y = Cl) are encompassed by the general formula 1 and also show biological, plant growth regulating properties.

The process is preferably carried out in the presence of reactants which are inert Solvents and / or diluents carried out. Aprotic solvents are particularly suitable, such as aliphatic and aromatic hydrocarbons, e.g. B. hexane, cyclohexane, benzene, toluene Xylene, halogenated hydrocarbons such as chlorinated ethylene, carbon tetrachloride, chloroform, chlorobenzene, also ethers and ethereal compounds such as diethyl ether and tetrahydrofuran.

To achieve a complete implementation can NEN the alcohols used as reactants, carboxylic acids and carboxylic acid anhydrides, in over Shot used as a solvent or diluent.

It may also be necessary to add an acid-binding agent to the reaction mixture

Tertiary amines are particularly useful for this purpose Question.

The reaction temperatures are in the range from 0 to 100 ° C, the reaction time can be between a few minutes and several days. It depends largely on the responsiveness of the person alcohols used.

The following examples are provided for illustrative purposes of the method according to the invention. In the following tables there are further, new / i-haloethyl-silanes of the formula 1 prepared by the route described in the examples summarized.

The temperatures are given in degrees Celsius, the pressure in Torr.

Calculated . .. C 49J, H 5.4, Cl 11.2, Si 8.9;
found C 49.4, H 5.4, Cl 11.7, Si 8.9.

AlhyI-iris- (4'-ehlorbenzoxy) -silane, b.p .: 2 (K) to 210 0.01 torr. / 1 = 1.5636 (compound 4).

Example 2

26.9 g obtained according to Example 1 a)? Chlorethyltris (acetyloxy) silane are dissolved in 40 ml of absolute benzene. At 50 ° to 55 °, 21.6 g of benzyl alcohol in 20 ml of absolute benzene are added over the course of 60 minutes. The mixture is stirred for 4 ¹ Z ₂ hours at 50 to 55 °. The reaction mixture is evaporated in vacuo, and 2QJL g of 2-chloroethyl- (dibenzyloxyacetyloxy) -silane are obtained. Kp .: 164 to 166 ° / 0.005 Torr, «S ⁵ == 1.5218 (compound 3).

Calculated ... C 59Λ H 5.8, α 9.7, Si 7.7:
found .... C 59.4, H 5.6, Cl 10.2, Si 8.0.

Example 3

10.5 g of 2-chloroethyl-lrichlorosilane are dissolved in 150 ml dissolved in absolute diethyl ether. At -5 to -10 °, 22.7 g of 4-chlorobenzyl alcohol are obtained within 5 minutes and then added within from 30 minutes 12.6 g of absolute pyridine, dissolved in 50 ml of absolute ether. The mixture is stirred for a further hour at 0 ° and then under reflux for 18 hours.

The reaction mixture is filtered, the filtrate washed twice with water, dried and evaporated in vacuo. 23.5 g of 2-chloro are obtained

45 Calculated
found.

C 53.5. H 4.3, Cl 27.5. Si 5.4: C-53.4. H 4.3, Cl 27.8. Si 5.6.

at

spat

1 4

example 1

a) 40.8 g of 2-chloroethyl-trichlorosilane are in 71.5 g Acetic anhydride dissolved and left to stand closed for 21 hours at room temperature. That The reaction product is evaporated in vacuo. 44.6 g of 2-chloroethyl-tris- (acetyloxy) -silane are obtained, Kp .: 85 to 88 ° / E, 1 Torr, n? = 1.6687 (connection 1)

Calculated ... C 35.8, H 4.8, Cl 13.20, Si 10.4; found .... C 36.0, H 4.7, Cl 13.4, Si 10.5.

b) 26.9 g of 2-chloroethyl-tris (acctyloxy) -silane are

dissolved in Αϋ ml of absolute benzene. At 50 to 55 °, 10.8 g of benzyl alcohol in 20 ml of absolute benzene are added over the course of 60 minutes. The mixture is stirred for 4V for ₂ hours at 50 to 55 °. The reaction mixture is evaporated in vacuo, and 14.3 g of 2-chloroethyl- (benzyloxy-diacctyloxy) -silane are obtained, boiling point : 125 to 12,000,000 Torr, nf = 1.4840 (compound 2)

16.9 g of 3-chloro-buten- (2) -ol are dissolved in 150 ml of absolute diethyl ether. It is cooled to -10 to -5 ". 12.6 g of absolute pyridine are added and a solution of 10.5 g of 2-chloroethyl-trichlorosilane in 50 ml of absolute diethyl ether is then added dropwise over the course of one hour at the same temperature Mixture for 1 hour at 0 °, 2 hours at room temperature and 18 hours under reflux, then filtered, the filtrate washed quickly with ice-cold water, dried and evaporated in vacuo to give 21.5 g of 2-chloroethyl-tris- [3 ' -chloro-butynyl- (2 ') -oxy] -silane, bp .: 145 to 150 0.05 Torr, η ■' ■ '■ · = 1.4912. (Compound 5).

Calculated ... C 41.2. H 5.4, Cl 34.8, Si 6.9: found .... C 41.6, H 5.4, Cl 34.9. Si 6.6.

40 Example 5 (preparation of an intermediate product)

59.4 g of I-chloroethyl trichlorosilane are dissolved in 750 ml dissolved in absolute diethyl ether. At -5 to - 10 a mixture of 34.9 g Hcxan- (l) -ol and 23.7 ^ absolute pyridine, dissolved in 250 ml of absolute ether, added within one hour. Now one stirs the mixture for 12 hours at room temperature. It is then filtered and the filtrate is evaporated in vacuo. After fractional distillation, 39.2 g of 2-chloroethyl (hexyloxy-dichloro) -s> lan, boiling point: 69, are obtained up to 7270.1 Torr.

Calculated ... C 36.5, H 6.5, Si 10.7; found .... C 36.5. H 6.5, Si 11.0.

Example 6

59.4 g of Z-chloroethyl trichlorosilane are dissolved in 750 ml dissolved in absolute diethyl ether. At -5 to -10 a mixture of 69.7 g of Hcxan- (l) -ol and 47.5 g absolute pyridine, dissolved in 250 ml of absolute ether. added within an hour. Nan is stirred

so the mixture! 2 hours at room temperature. It is then nitrated and the filtrate is evaporated in vacuo. After fractional distillation, 32.5 g of 2-chloroethyl (dihexy! Oxy-chloro) silane, boiling point: 97, are obtained up to 10270.001 Torr, n? = 1.4423 (compound 6).

Tables with further compounds of the formula now follow

O-R,

X-CH ₂ -CH ₂ -Si-OR ₂ O-R ₃

The tables below also contain some known compounds, but which are used as active ingredients can be present in the agents according to the invention.

aöelle 1

15th

Ir. R, = R, = - R, X Physical data Cp. Torr: h. ) (Fp .: i 80-82 '- / 22 6a methyl Cl Kp .: 80-81714 7th ethyl Cl Kp .: 83-4V14 8th ethyl Br Kp .: 55-60 / 0.1 9 n-propyl C! Kp .: 110-113 / 14 10 isopropyl Cl Kp .: 1 3-85 0.1 11th n-butyl Cl Kp .: Μ3--97 0.8 12th Isobutyl Cl Kp .: :; θ-83 '0.5 13th sec-butyl Cl Kp .: 108-112 "0.1 14th n-pentyl Cl Kp .: 1! 5-il8 ^c V0.2 15th 2-MethyI-buiyI Ci Kp .: 96-100 '/ O.l 16 3-methyl-butyl Cl Kp .: 145-50 ° / 0.01 17th Hexyl Br Kp .: = 1.4480 18th 2-ethylhexyl Cl fl? ^c = ■: 1.4460 19th 1-methyl-heptyl Cl n'r = : 65-70 ' ^J · 0.001 20th Octyl Cl Kp .: 3 65—7Ο- / Ο.ΟΟ5 21 Octyl Br Kp .: - 1.4500 22nd 1-methyl-4-ethyl-hexyl Cl _Π ί- = = 1.4458 23 Decyl Cl IV; = - 1.4511 24 Undecyl Cl ) i ^? S - -. 1.4545 25th Dodecyl Cl n $ = = 1.4582 26th Dodecyl Br η 'S - = 1.4543 27 Tetradecyl C! nt - -. 1.4540 28 Hexadecyl Cl ηΐ - 33-36 29 Octadecyl Cl Fp .: 35-36 30th Octadecyl Br Fp .: 123-26 ° / 0.001 31 2-chloroethyl Cl Kp .: 128 " 0.001 32 2-chloropropyl Cl Kp .: 210-15 "/ 0.03 33 6-chlorohexyl C! Kp .: 103-105 0.05 34 2-methoxyethyl Cl Kp .: = 1.4497 35 2-methoxyethyl Br ηψ - 122 125 0.005 36 2-ethoxyethyl Cl Kp .: 173 0.0O ¹ 37 2-ethoxyethyl Br Kp .: = 1.4495 38 2-butyloxyethyl Br η? - 14α-145 '0.001 39 2-allyloxyethyl Cl Kp .: = 1.4669 40 2-allyloxyethyl Br 11? = = 1.4397 41 2- (r-methylethenyloxy) ethyl Cl Hf = 134-138 0.005 42 2-propyloxyethyl Cl Kp .: = 1.4473 43 2-propyloxyethyl Br nt- '· 125-128 0.005 44 2- (1'-methylethyloxy) ethyl Cl Kp .: = 1.4501 45 2-hexyloxyethyl Cl Hf ■ = 1.4478 46 2- (2'-methoxyethoxy) ethyl Cl nf ■■ = 1.4409 47 ? - (2'-Ethoxyethoxy) ethyl Cl = 1.4441 48 2- (2'-Butyloxyätlioxy) üth \ I bi- η '■' ■ 195 200 0.005 49 2-ethylthioethyl ci Kp .: = 1.51 His 50 2-ethylthioethyl Br η: = 1.4895 51 2-octylthioyl Br η = 1.5361 52 1-phenylethyl Br II '. - 1.5340 53 3-PhcnyIprop \ l C! η = 1.5460 54 2-phenoxyethyl Cl Il = 1.5487 55 2-phenoxyeth Br H 95-KX) 0.2 56 2-propenyl Cl Kp .: 609 521/471

17 continued

No. R ₁ = R, = R ₃

57 2-propenyl

58 2-butenyl

59 2-butenyl

60 3,7-dimethyl-2-octenyl

61 10-undecenyl

62 9-octadecenyl

63 3,7-dimethyl-2,6-ocuidienyl

64 2-propynyl

65 2-propynyl

66 2-butynyl

17 2-butynyl

18 3-hexynyl

19 1-Athynylbutyl

70 3-chloro-2-butenyl

71 3-chloro-2-butenyl

72 3-phenyl-2-propenyl

73 / <- phenyl-2-propenyl

74 2-cyanoethyl

75 ethoxycarbonyl-methyl

76 1-EthoxycarbonyK 1 -methyl) ethyl

77 butoxycarbonyl-methyl

78 cyclohexyl

79 cyclohexylmethyl

80 cyclohexylmethyl

8 1 S-cyclohexylpropyl

82 3,4-Dimethylcyclgiiexyl

83 3,5-dimethylcyclohexyl

84 4-tert-butylcyclohexyl

85 (-) bornenyl

86 6,6-Dimethylbicyclo [3,1,1] hept--2-en-2-y-ethyl

87 benzyl

88 benzyl

fc9 4-chlorobenzyl

90 4-chlorobenzyl

91 4-methoxybenzyl

92 4-methoxybenzy!

93 2,4-dichlorobenzyl

94 4-methylbenzyl

95 4-methylbenzyl

96 phenyl

97 4-chlorophenyl

98 3-chlorophenyl

99 3,4-dichlorophenyl

100 3,5-dichlorophynyl

101 4-bromophenyl

102 4-methoxyphenyl

103 4-methoxyphenyl

104 3-methoxyphenyl

105 4-butyloxyphenyl

106 4-tert-butylphenyl

X Physical Daien Kp. Torr: υ. ι (Fp .: : 123 0.001 Br Kp. : 110-15 0.2 Cl Kp. : 115-20 0.01 Br Kp. = 1.4707 Cl Il = 1.4606 Cl η Υ = 1.4645 Cl / Ir ¹ = 1.4682 Cl ir-: : 94 0.35 Cl Kp. : 115-20 0.00: Br Kp. : 180 0.2 Br Kp. : J 30-135 0.01 Cl Kp. : 170-5 0.005 Cl Kp. = 1.4715 Cl ir : 145-50 0.OUf Cl Kp. = 1.5005 Br η = 1.5832 Cl ir) = 1.5882 Br /1 = 1.4696 Cl 11 ': = 1.4492 Cl ηΐ : 154-58 0.3 Cl Kp. = - 1.4480 Cl If'-: : 165-170 η. (X Cl Kp. : 180-190 0.0 ( Cl Kp. = 1.4833 Br H;" = 1.4782 Cl η · -. ' = 1.4746 Cl π ^: - ' = 1.4673 Cl nS ¹ = 1.4695 Br nt = 1.4890 Cl = 1.4687 Cl η Ψ : 190-200 0. (X Cl Kp. = 1.5612 Br Hf : 200-20 ° 0.01 Cl Kp. = 1.5757 Br nf = 1.5224 Cl = 1.5569 Br / 1 ΐ = 1.6637 Cl Π ff = 1.5433 Cl η'-. = 1.5543 Br ir- = 1.5623 Cl « = 1.5769 Cl Jl η " = 1.5262 Ci "27
Il D = 1.5257 Cl η " = 1.5268 Cl η Z = 1.5418 Cl η'J = 1.5620 Cl η = 1.5641 Br η = 1.5590 Cl η = 1.5307 α η : 75 77 Cl Fp.

continuation

19th

20th

R, = R ₂ = R, physical data (Hp .; Kp. Torr: n. I

107 108 109 Π0 111 112 113

3-methylphenyl

3-methylphynyl

3,4-dimethylphenyl

3-formylphenyl

4-cyanophenyl

4-ethoxycarbonylphenyl

3-ethoxycarbonylphenyl

Cl Br Cl Cl Cl Cl Cl

Cl

ni '= 1.5385 μ Γ = 1.5490 ηϊ = 1.4935 Mp .: 98-101 Mp .: 106-111 Mp .: 112-114 Mp .: 65-70

Bp: 195-200 0.001

CH,

O ^Χ

CH, -

CH, -

Γλ

O ^χ

CH, -

Cl

Cl

Bp: 152-154 0.001

ηΐ ¹ = 1.5771

ηΐ = 1.4727

CH, -

/ \ O

H ₃ C CH ₃ -H ₃ C _n

H ₃ C ⁷ O

CH ₁

⁰ CH ₂ - (OCH ₂ CHj) ₂ -

Br

Cl

Cl

Cl

(ΐ? = 1.4840

«5? = 1.4695

nf = 1.4712

wi? = 1.4732

Table Il

123 123 a

R ₁ - R ₂ - R ₁ to R _u R ₄ isi

Methyl methyl

Br

Cl

Physical data

Kp .: 120-122 Kp .: 85-88 '0.1

21

continuation

-7

22nd

a 125 126 127 128 129 130 f32 1.33 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 153 154 155 156 157 158 159 161 162 163 165 166 167 168 169 170 171 172 174 175 176 177

R ₁ = R; = R ₃ = -CO- Rj R ₄ Ut

ethyl

ethyl

Pentyl

1-methylpentyl

1-ethylpentyl

Heptyl

Octyl

Undecyl

Undecyl

Pentadecyi

Heptadecyl

2-propenyl

1-propenyl

2-propenyl

9-decenyl

1,3-pentadienyl

8,11-heptadccadienyl

2-chloroethyl

1-bromopentyl

10-bromodecyl

10-Bromdecy!

cis-2-chloroethenyl

cis-2-chloroethenyl

Phenylmethyl

Phenylmethyl

2-phenylethyl

4-chlorophynyl methy!

3-methylphenylmethyl

3- (4'-methoxyphenyl) ethyl

3-oxobutyl

3-oxobutyl

5-phenyl-5-oxo-pentyl

2-ethoxyethyl

3-phenoxypropyl

2,4-dichlorophenoxymethyl

2,4-dichlorophenoxymethyl

2-phenyl-1-ethenyl

2-phenyl-1-ethenyl

2- (3 ', 4'-dichlorophenyl) -l-alhenyl

2- (4'-methoxypheny 1-1-ethenyl

Cyclohexylmethyl

Cyclohexylmethyl

Cyclohexyl

Cyclopropyl

3-cyclohexyl

3-cyclohexynyl

2-cyclopentyl-1-methyl

Phenyl

4-chlorophenyl

4-methoxyplienyl

4-methylphenyl

Cl Br Cl Cl Cl Cl Cl Cl Br Cl Cl Cl Cl Br Cl Cl Cl Cl Cl Cl Br Cl Br Cl Br Cl Cl Cl Cl Cl Br Cl Cl Cl Cl Br Cl Br Cl Cl Cl Br Cl Cl Cl Br Cl Cl Br Bi-Cl

Musical duu-n 101-104 0.0? Kp .: 115-125 0.002 Kp .: = 1.4286 n '{~ - = 1.4290 Jl> = = 1.4325 IV. "- = 1.4376 H? = = 1.4332 / If = 42- ^ 4 ^: Fp. 44-47 Fp. 45-50 Fp .: 54-57 Fp .: - 1.4484 ηΐ = 24-27 Fp .: = 1.4621 (IV = = 1.4480 / 1 = 116-120 Fp .: = 1.4705 / 1 = = 1.4681 η ^: = = 1.4513 / ι ν = 49-50- Fp .: 48-50 Fp .: 25 ° Fp .: 55-58 " Fp .: 74-78 Fp .: 20-30 Fp .: 35-39 Fp .: 99-103 Fp .: 57-60 Fp .: 98-102 Fp .: = 1.4590 IU = 1.4841 ηΐ = 73-75 Fp .: = 1.4365 Hc = 58-60 Fp .: 140 ° Fp .: 137-138 Fp .: 128-130 Fp .: 129-131 Fp .: > 235 ° Fp .: 178 ° Fp .: = 1.4494 Il ^ O -
η ο - = 1.4592 / ι S = = 1.4578 η'ζ - = 1.4515 ; r: = = 1.4740 η ί "= = 1.4807 ην - = 1.4630 IV: '- = 1.5632 η r - 233 ° Fp .: 177-178 Fp .: 165-170 Fp .:

23

Continued 24

R ₁ ■ = R, --- ■ Rj = --CO R ₄ R ₄ is physical data

Br

Fp .: 123-126

S ^X Br

Fp .: 123-125

Table III

182 Benzyl = R * 183 Benzyl "R.i 184 Benzyl Benzyl 184 a ethyl ethyl 185 Pentyl Pentyl 186 Octyl = Rj 187 Octyl Octyl 188 2-butynyl 2-bulinyl 189 2-butenyl 2-butene vl 190 4-chloro-benzyl = R, 191 4-chlorobenzyl = R ₃ 192 3.7-dimethyl-7-octerjyl = R ₃ 194 4-methoxybenzyl = R _?

R, = CO-R ₄ X R ₄ is methyl Cl methyl Br methyl Cl methyl Cl methyl Br methyl Cl methyl Cl methyl Cl methyl Cl ethyl Cl ethyl Br ethyl Cl Äthvl Cl

Physical data

Kp .: 126 2770.001 Kp .: 140-143 ° 0.01 Kp .: 164-166 .0.0Of Kp .: 62-65 ^ 0.01 Kp .: 104-110 "0.001 Kp .: 115— 120 '0.02 Kp .: 150-152 ^r O.OOf Kp .: 108-110 ^c 0.02 Kp .: 94-98 ° 0.00! Iv ~ = 1.4940 π Γ = 1.5042 η = 1.4525 Ii = 1.4890

Table IV

H ₃ C

H ₃ CH

Hexvl Hexvl

Cl

Anion

Cl

Physical data

M.p .: 25-35 ^C

196 ^N tf — CHXH, -

H, C H

Benzvl Benzvl

Cl

tv; = 1.5212 m.p .: 35 ^C.

Table V

Compounds in which R ₁ and R ₂ together with the neighboring atoms form an Si-containing 1 letciocyclus

link

Physical data

H ₁ C CH ₂ -O OC ₁₁ H ₁ ,

C Si-CH ₁ -CH ₁ -Cl

H ₁ C CH ₂ -O

CH ₂

\
0

. I.

0-Si-CH ₂ -CH ₁ -Cl

OC ₁ H ₅ CO-O OC ₅ H ₁₁

Si-CH ₂ -CH ₂ -Cl CO-O CO-O OC ₅ H ₁₁

\ l

Si-CH ₁ -CH ₁ -Cl \
CO-O

CO-O OC ₀ H ₁ ,

Si-CH ₁ -CH, -Cl

CO-O

CO

Si-CH ₁ -CH ₁ -Cl

, / I

O OC ₁₁ H _n Bp .: 115 to 120: 0.005

η): = 1.5233

= 1.4718

= 1.4537

= 1.4400

= 1.4502

Table VI

Compounds of the formula I. in which Y is chlorine.

R ₁ = R ₂

203 methyl 206 Hexyl 207 Hexyl 208 Octyl 209 2-butynyl 210 3-hexynyl 211 6-chlorohydroxyl 212 2-methoxyethyl 213 2-ethoxyethyl

Cl Cl Br Cl Π Cl Cl Cl CI Physical data (Fp .: Kp.; Torr: m )

Kp .: = 68 '/ 14 Kp .: 97-102 "/0.0Ol; i>: = 1.4532

nr = 1.4479; Kp. 135-13 ^ / 0.01 S ₁ - ". i A £ .na

" - 1 .TVI / O

/ li, - = 1.4764

n? = 1.4707. Bp. 1S8 -190 ° 0.2 Bp .: 90- 94 0.01 Bp .: 87 92 0. (K) I.

-location R ₁ = R ₂ X Physical data , 4564 No. (Γρ .: Kp .. 'Torr: η, ) , 4836 1-phenylethyl Cl Bp: 134 '/ 0.0Ol , 4766 214 3-phenylpropyl Cl II ?; == 1.5192 , 5265, bp 160, 0.001 215 Dodecyl Cl II ί ¹ = , 5552 216 Cyclohexyl Cl Il ί! = , 5343 217 Cyclohexyl methyl Cl π ?! ' = , 5455 218 Benzyl Cl π ν; ¹ = , 5372 219 4-chlorobenzyl Cl Πη '== 1.5486 220 4-methylbenzyl Cl Il ΐ '= 221 4-methoxybenzyl Cl II ΐ '= 222 3-methylphenyl Cl Hi, "= 223 3-methoxyphenyl Cl 11? = 224

Claims (2)

Patent claims: 1. 2-halogenoethyl-organooxy-silanes of the formula 1 Ο — R ₁ -Si — ΟΙ wherein X is chlorine or bromine, Y is chlorine or a radical - OR ₃ , R ₁ , R ₂ and R ₃ independently of one another unsubstituted alkyl radicals each having 6 to 18 carbon atoms, by chlorine, C ₁ -C ₈ alkoxy, C _r C ₈ - Alkylthio, C ₃ -C ₆ alkenyloxy, phenoxy, phenyl, C ₁ -C _{4 cycloalkyl, cyano, C 1 -C 8} alkoxycarbonyl, tetrahydropyranyl, tetrahydrofuranyi. Thienyl, dioxanyl or dioxolanyl substituted C _{1 -C 18} -alkyl radicals, Cj-Qg-alkenyl-. Chloralkenyl or phenylaikenyl radicals, C ₃ -C ₈ alkynyl radicals, C ₃ - to C ^ cycloalkyl and cycloalkenyl radicals, optionally one or more times with chlorine or bromine. QC ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -AlkYHhIO., Q-Cg-alkanoyl, C ₁ -C ₈ -alkoxycarbonyl, formyl or cyano substituted phenyl radicals, optionally mono- or polysubstituted by chlorine , C ₁ -C ₈ -AlIlCyI or C _r C ₈ -alkoxy substituted benzyl resle, or at least one of the radicals R ₁ to R _{3 is} a »radical —CO-R ₄ , in which each R _{4 has the} same meanings as under R ₁ to R ₃ indicated, R "- is also a five- or six-membered heterocyclic aromatic ring or an alkyl radical substituted by an oxo group, methoxyphenyl or dichlorophenoxy or an alkenyl radical substituted by chlorophenyl, dichlorophenyl and methoxyphenyl, the radicals R ₁ to R ₃ but can also represent lower alkyl radicals, if X is bromine, and finally R ₁ and R ₂ , also in the form —COR ₄ . together with the Si group can form a heterocyclic system, in which case Y must represent a radical - OR ₃ . 2. Process for the preparation of 2-haloethyl-organooxy-silanes of formula 1 according to claim 1, characterized in that a 2-haloethyl-trichlorosilane is used in a manner known per se of formula II X-CH ₂ -CH ₂ -Si (Cl) ₃ (H) and, if desired, in the one thus obtained Siian of formula 111