CH528209A - Plant-growth regulating agents - contg haloethyl -silane compounds - Google Patents

Abstract

Agent for regulating plant growth contains as active component >=1 cpd. of the formula XCH2CH2Si(Y)(OR1) (OR2) (I) (where Y is Cl or OR3; X is Cl or Br; and R1-R3 are alkyl (opt. subst. by halogen, alk(en)oxy, phenyl, phenoxy, CN, cycloalk(en)yl, alkylthio, alkoxycrabonyl, >=1 heterocyclic residue and/or di- and tri-alkylammonio), alkenyl phenyl- or halo-alkenyl, alkynyl, cycloalk(en)yl, phenyl (opt. subst. by CN, NO2, alkyl, halogen, haloalkyl, alkoxy, alkylthio, alkanoyl and/or alkoxycrbonyl), benzyl (opt. subst. by alkyl, alkoxy and/or halogen) or -COR4 in which R4 is alkyl (opt. subst. by cycloalkyl, phenyl or phenoxy), oxoalkyl, alkenyl (opt. subst. by cycloalkyl or phenyl) (phenyl residues opt. subst. by alkyl, alkoxy and/or halogen), alkynyl, haloalk(en)yl, phenyl-ooalkyl, alkoxyalkyl, alkoxycarbonylalkyl, cycloalk(en)yl, phenyl (opt. subst. by halogen, lower alkyl or alkoxy) or a 5- or 6-membered heterocyclic residue; or R1 and R2 are linked so as to form an (un)satd. heterocyclic residue. (I) are non-phytotoxic, and their plant-growth regulating activity is similar to that of ethylene. Their stability is very good, so that formulations contg. (I) need not contain a stabilizing acid additive.

Description

       

  
 



  Means for regulating plant development
The present invention relates to a new agent and its use for regulating plant development. SS-haloethylsilanes serve as active ingredients.



   The ß-haloethylsilanes contained in the new agent as an active component correspond to formula I:
EMI1.1

In this formula:
X chlorine or bromine
Y chlorine or the remainder -OR3,
R1, R2 and R3 independently of one another are alkyl radicals, by halogen, alkoxy, alkenyloxy, phenyl, phenoxy, cyano, cycloalkyl, cycloalkenyl, alkylthio, alkoxycarbonyl, by at least one heterocyclic radical and / or by di- and tri-alkylammonio-substituted alkyl radicals, Alkenyl, phenylalkenyl or haloalkenyl, alkynyl, cycloalkyl, cycloalkenyl, optionally phenyl radicals monosubstituted or polysubstituted by cyano, nitro, alkyl, halogen, haloalkyl, alkoxy, alkylthio, alkanoyl and / or alkoxycarbonyl, optionally by alkyl, alkoxy and / or halogen - or polysubstituted benzyl radicals;

   one or more of the symbols R1, R2 and R3 can also represent the group -COR4, in which R4 represents an alkyl, oxoalkyl, alkenyl or alkynyl radical, a haloalkyl or haloalkenyl radical, one by cycloalkyl, phenyl or Phenoxy-substituted alkyl radical or an alkenyl radical substituted by cycloalkyl or phenyl, it being possible for the phenyl radicals to be substituted by alkyl, alkoxy and / or halogen, also for a phenyl-oxoalkyl, alkoxyalkyl, an alkoxycarbonylalkyl, a cycloalkyl or cycloalkenyl radical, or a phenyl radical, which the latter can be substituted by halogen, lower alkyl or alkoxy and finally represents a 5- or 6-membered heterocyclic radical.



   R1 and R2, even if they are present as a group -COR4, can form a saturated or unsaturated heterocyclic ring system together with the adjacent oxygen atoms and the Si atoms.



   Particularly suitable alkyl radicals in formula I are straight-chain or branched radicals having 1 to 18 carbon atoms, such as. B. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, n-hexyl, n-octyl, n-dodecyl, n-octadecyl, etc. In particular, the straight-chain or branched alkyl radicals with 1 to 8 carbon atoms the alkyl substituents or the alkyl part of alkoxy, alkylthio, di- and tri-alkylammonio or alkoxycarbonyl substituents of an alkyl radical or a phenyl radical. Among haloalkyl radicals those with 1 to 6 carbon atoms are preferred, which can be substituted in particular by fluorine, chlorine and / or bromine, such as. B. trifluoromethyl, 2-chloroethyl, 6-chlorohexyl, etc. Among alkenyl radicals, straight-chain or branched radicals having 3 to 18 carbon atoms are preferred in formula I, e.g. B.

   Propenyl, butenyl, octenyl, decenyl, heptadecenyl radicals. These alkenyl radicals can be substituted one or more times by halogen, such as fluorine, chlorine, bromine and / or iodine. In particular, alkenyl radicals with 3 to 6 carbon atoms form the alkenyl part of alkenyloxy radicals. Alkynyl radicals preferably have 3 to 8 carbon atoms in a straight chain, such as. B. 2 propynyl, 2-butynyl or 3-hexynyl. Cycloalkyl and cycloalkenyl radicals are mono- or polycyclic and preferably contain 3 to 12 carbon atoms, such as. B. Cyclopropyl, Cyclopentyl, Cyclopentenyl, Cyclohexenyl, Bicycloheptyl, etc.



   5- or 6-membered heterocyclic radicals R4 or as substituents of alkyl radicals R1, R2 and R3 contain 1 or more, e.g. B. two heteroatoms, especially nitrogen and / or oxygen, heterocyclic ring systems containing the Si atom, which are formed by the radicals R1 and R2 including the -COR4 type, can be saturated or unsaturated.



   The anions of the di- and tri-alkylammonio radicals (which can be regarded as the salt form of a dialkylamino radical) are in particular those of hydrohalic acids, alkylsulfonic acids and alkylphosphoric acid.



   The β-haloethylsilanes of the formula I influence the development of above and below ground parts of plants in various ways, they are not phytotoxic in the usual concentrations and have a low toxicity to warm blooded animals. The active ingredients do not cause any morphological changes or damage that would cause the plant to die. The compounds are not mutagenic. Their effect is different from that of a herbicidal active ingredient and a fertilizer. Rather, the effect corresponds to the effects that can be observed when ethylene is applied to different parts of the plant.

   It is known that the plant itself also produces ethylene to different degrees in different stages of development, in particular before and during the ripening process of the fruit and at the end of the vegetation period when the fruit and leaves are detached. Since the influence of chemical substances on ripening, fruit detachment and leaf detachment is of great economic importance for fruit, citrus fruit, pineapple and cotton cultivation, compounds were sought that could achieve such effects without causing any damage to the treated plants . In the meantime, various classes of substances have become known with which individual such effects that influence growth could be achieved, but their range of effects in no way corresponds to that of ethylene.



   Compounds which split off ethylene under certain conditions are known. Such compounds are either relatively unstable under the influence of weather, because they are very sensitive to hydrolysis, or they are phytotoxic. In South African Patent No. 68/1036, β-haloethylphosphonic acid derivatives are described as active ingredients which regulate plant growth. These compounds decompose in and on the plant, releasing ethylene and are therefore similar to ethylene in terms of their effects and breadth of activity. Because of their very poor stability, however, phosphonic acid derivatives are unable to meet the requirements placed on them. Since they are only stable in an acidic environment, more precisely in a pH range below 5, the active ingredient concentrates must be stabilized by adding acids.

   However, this addition of acid limits the scope of these active ingredients with regard to phytotoxic effects. In addition, the storage of such sensitive active ingredient concentrates is associated with difficulties.



   Haloalkyl-methyl-silanes are also known as herbicidal active ingredients, cf. US Pat. Nos. 3,390,976, 3,390,977 and J. K. Leasure et al., J. Med. Chem. 9, 949 (1966). Ss-chloroethyl-tris (alkoxy) -silanes and ss-chloroethylacetoxy-dialkoxy- or ß-chloroethyl-diacetoxy-alkoxy-silanes were obtained by FW Boye et al., J. Org. Chem. 16, 391 (1951), resp. 17, 1386 (1952).



   US Pat. No. 3,183,076 describes α-chloroethyl-methyldialkoxy-silanes which can be used to promote germination, leaf detachment, and the like.



   The present invention relates to new agents containing ss-haloethylsilanes as active ingredients which, in the various stages of plant development, have a stimulating or retarding effect on plant growth. Due to the very good stability of the active ingredients of the formula I, these agents do not need to contain any stabilizing acid additives in addition to the customary carriers, distributors, light stabilizers and oxidation stabilizers and can therefore be used without restriction. The new agents influence vegetative plant growth and germination, promote flower formation, fruit development and the formation of separating tissues. In monocotyledons there was an increase in tillering and branching with a simultaneous decrease in length growth.



  In addition, the supporting tissue of the stems of the treated plants was strengthened. The formation of undesirable stinging instincts in various types of plants is greatly reduced. Furthermore, rubber trees are stimulated to produce a greater amount of latex outflow, an effect that is of great economic importance. As tests have shown, the rooting of seedlings and cuttings as well as the tuber formation in potatoes is promoted. In addition, dormant rhizomes sprout at the same time, which is particularly important with various perennial weeds such as couch grass, johnson grass and cyperus, which can then be easily destroyed or contained with herbicides. The germinability of seeds, such as B. seed potatoes and legumes, is encouraged at lower concentrations, prevented at higher. Both the one and the other effect are of economic importance.

   With many ornamental and cultivated plants, it is possible to control the flowering date and number of flowers. This effect plays a particularly important role in pineapples. If all the bushes are in bloom at the same time, the bushes can be taken seriously within a comparatively short time. In cucurbits, there is a shift in the sex differentiation in favor of the female flowers.



   Tests also showed that fruit trees thinning out in flowers and fruit. Furthermore, z. B. in apples, pears, peaches, tomatoes, bananas and pineapples accelerates and improves fruit ripening and coloration. The fruit and leaf abscission is considerably facilitated by the formation of separating tissue.



  This is of great economic importance for mechanical harvesting, e.g. B. of citrus fruits or cotton. Ornamental plants such as chrysanthemums, rhododendrons, carnations and roses are also defoliated at high concentrations.



   The extent and type of effect depend on a wide variety of factors, in particular on the application time in relation to the development stage of the plant and the application concentration. However, these factors vary 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 the flower system forms; Plants whose fruits are used respectively. are used immediately after flowering or at an appropriate distance before harvest. The active ingredients are applied in the form of solid or liquid compositions both to above-ground parts of plants and in the soil or on the ground.

   Application to the above-ground parts of the plant, for which solutions or aqueous dispersions are most suitable, is preferred. For the treatment of the growth substrate (the soil), besides solutions and dispersions, dusts, granulates and grit are also suitable.



   The plant growth-regulating effect of the agents according to the invention can often be favorably influenced by the addition of organic or inorganic acids or bases, such as. B. acetic acid and sodium carbonate.



   With citrus fruits - oranges - it was found that the detachment of fruits after application of the active ingredients of the formula I is much easier. Various active ingredients were sprayed as solutions in concentrations of 0.2-0.4% onto branches with good fruit hangings from various orange trees. After 14 days, the experiments were carried out using the method developed by W. C. Wilson and C. H. Hendershott, cf. Proc. At the. Soc. Hoard. Sc. 90, 123-129 (1967). Here, the force required to remove a fruit is determined in kg.
EMI3.1


<tb>



  Active ingredient: <SEP> concentration <SEP> force <SEP> in <SEP> kg
<tb> 2-chloroethyl-tris- (ethoxy) - <SEP> 0.2 <SEP>% <SEP> 4.5
<tb> silane <SEP> 0.4 <SEP>% <SEP> 1.5
<tb> 2-chloroEthyl.-tris <SEP> (octyl <SEP> 0.2 <SEP>% <SEP> 3.7
<tb> oxy) <SEP> silane <SEP> 0.4 <SEP>% <SEP> *
<tb> 2-Chloräthyi-tri <SEP> (benzyl- <SEP> 0.2 <SEP>%
<tb> oxy <SEP>) -silane <SEP> 0, <SEP> <SEP>% <SEP> * <SEP>
<tb> <SEP> 2-chloroethyl-tris- (dodecyl- <SEP> 0.2% <SEP> 4.7
<tb> oxy) <SEP> -silane <SEP> 0> 4 <SEP>% <SEP> 1> 1 <SEP>
<tb> Control <SEP> 8, <SEP> G <SEP>
<tb> *) The fruits hanging on the tree were so easy to remove,

   that no measurement could be made.



   Equally good and significant values were obtained with agents containing the following compounds:
2-chloroethyl-tris- (2'-chloroethoxy) -silane
2-chloroethyl-tris- [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-tris- [hexynyl- (3 ') -oxy] -silane
2-chloroethyl-tris (6'-chlorohexyloxy) -silane
2-chloroethyl-tris- (4'-methoxy-benzyloxy) -silane
2-chloroethyl-tris- (2 ', 4' -dichlorobenzyloxy) -silane
2-chloroethyl-tris- (4'-chlorobenzyloxy) -silane.



   On bean leaf segments it was observed that leaf abscission is facilitated or promoted by the formation of separating tissue. Segments of bean leaves of the Tempo variety were immersed in a solution of 0.002% active ingredient and 4-8 segments per active ingredient were left in the active ingredient solution for 6 days under controlled conditions.



   3.5 resp. 6 days after the start of treatment, the number of abscissions that had occurred (= constriction of the stem at the abscission zone on the leaf side) was determined. The evaluation was carried out according to a grading system of 1-9, whereby grade 9 = 0 and grade 1 = 8 corresponds to abscissions.
EMI4.1


<tb>



   <SEP> grades <SEP> assessment <SEP> according to
<tb> <SEP> evaluation
<tb> 6 <SEP> buttons
<tb> <SEP>. <SEP>. <SEP>. <SEP>. <SEP>
<tb>



   <SEP> 2-bromoethyl-tris- <SEP> 1 <SEP> 1 <SEP> 1
<tb> <SEP> (benzyloxy <SEP> <SEP>) <SEP> -sIan
<tb> <SEP> 2-chloroethyl-tris- <SEP> 1 <SEP> 1 <SEP> 1 <SEP>
<tb> <SEP> (4'-chlorobenzyloxy) -silane
<tb> <SEP> 2-chloroethyl-tris- <SEP> 1 <SEP> 1 <SEP> 3 <SEP>
<tb> <SEP> (octadecyloxy) <SEP> silane <SEP>
<tb> <SEP> 2-bromoethyl-tris- <SEP> 1 <SEP> 1 <SEP> 1
<tb> <SEP> [butenyl- (2 ') -oxy] -silane
<tb> <SEP> 2-chloroethyl-tris- (4'- <SEP> 1 <SEP> 1 <SEP> 1
<tb> <SEP> methoxyphenoxy) silane
<tb> <SEP> 2 <SEP> -Chl.

   <SEP> sr <SEP> ä <SEP> t <SEP> t71- <SEP> tr <SEP> is- <SEP> 1 <SEP> 1 <SEP> 1
<tb> <SEP> (carbobutoxymethoxy) <SEP> silane
<tb>
Comparable and significant values were obtained with agents containing the following compounds:
2-bromoethyl-tris- (ethoxy) -silane 2-bromoethyl-tris- (hexyloxy) -silane
2-bromoethyl-tris- (4'-chlorobenzyloxy) -silane
2-bromoethyl-tris- (octadecyloxy) -silane
2-Bromoethyl-tris- [propynyl- (2 ') -oxy] -silane
2-chloroethyl-tris- [propynyl- (2 ') -oxy] -silane, 2-chloroethyl-tris- (octyloxy) -silane
2-chloroethyl-tris- (b enzyloxy) -silane
2-chloroethyl-tris- (1'-carbethoxyethyloxy) silane
2-chloroethyl-tris- [3'-chlorobutenyl- (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'-methoxybenzyloxy) -silane 2-chloroethyl-tris- [hexynyl- (3 ') -oxyl] -silane
2-chloroethyl- (benzyloxy) -di-acetyloxy) -silane 2-chloroethyl- (di-octyloxy) - (acetyloxy) -silane.



   The acceleration of ripening was demonstrated on tomato plants in the following way:
Fournaise tomato plants were grown outdoors under plastic sheeting. After the plants had reached a height of 1.5 m, the tip of the shoot was cut off. When the first fruits turned reddish, the plants were sprayed with aqueous preparations made from emulsion concentrates of the active ingredients mentioned below. In each case 4 plants were treated with 1.5 It spray liquor, 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 cones were harvested.

   The sums of the yield amounts obtained are summarized in the following table:
EMI5.1


<tb> <SEP> active ingredient <SEP> lack of effort <SEP> yield <SEP> of <SEP> ripe <SEP> fruits <SEP>
<tb> <SEP> (ppm) <SEP> from <SEP> 3 <SEP> harvests
<tb> <SEP> Weight <SEP> in <SEP> kg <SEP>% <SEP> of the <SEP> total
<tb> <SEP> harvest
<tb> 2-chloroethyl-tris (octyl- <SEP> 2000 <SEP> 4.05 <SEP> 51.2
<tb> oxy) -siian <SEP> 4000 <SEP> 5.76 <SEP> 71.5 <SEP>
<tb> 2-chloroethyl-tris (benz- <SEP> 2000 <SEP> 5.66 <SEP> 73.7
<tb> yloxy) -silane <SEP> 4000 <SEP> 6.26 <SEP> 75.9
<tb> 2-chloroethyl-tris (3'- <SEP> 2000 <SEP> 5.92 <SEP> 85.2
<tb> chlorobutenyl- (2 ') - oxy) - <SEP> 4000 <SEP> 6.50 <SEP> 84.3
<tb> silane
<tb> 2-chloroethyl-tris (buten- <SEP> 2000 <SEP> 5.03 <SEP> 63.4
<tb> yl- (2 ') - oxy)

  -silane <SEP> 4000 <SEP> 6.06 <SEP> 75.3
<tb> 2-chloroethyl-tris (4'- <SEP> 2000 <SEP> 5.50 <SEP> 70.6
<tb> methoxy-benzyloxy) -silane <SEP> 4000 <SEP> 7.30 <SEP> 87.7
<tb> 2-chloroethyl-tris (4'- <SEP> 2000 <SEP> 3.37 <SEP> 62.9
<tb> chlorobenzyloxy) -silane <SEP> 4000 <SEP> 6.80 <SEP> 82.4 <SEP>
<tb> 2-chloroethyl-tris (hexi- <SEP> 2000 <SEP> 5.32 <SEP> 77.7
<tb> nyl- (3 ') - oxy) -silane <SEP> 4000 <SEP> 5.94 <SEP> 85.2
<tb> untreated <SEP> control <SEP> 3.41 <SEP> 52.0
<tb>
The resin flow, which can be related to the latex release from rubber trees, was stimulated in plum trees in the following way:
Bark segments were cut out of branches of 12-year-old plum trees (Prunus domestica).

   A 10% solution of active ingredient (active ingredient: xylene: castor oil = 1 2: 7) was applied to the branch surface of the intact trees below and above these incisions. 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.
EMI5.2


<tb>



   <SEP> active substance <SEP> amount of resin <SEP> in <SEP> grams
<tb> 2-Bromoethyl-tris (ethoxy) -silane <SEP> 0.37
<tb> 2-chloroethyl-tris (4'-methoxy
<tb> phenoxy) -silane <SEP> 1.81
<tb> 2-chloroethyl-tris (propynyl- (2 ') - <SEP>
<tb> oxy) <SEP> -silane <SEP> 0.53
<tb> 2-chloroethyl-tris (4'-chlorobenzyl
<tb> oxy) -silane <SEP> 0.52
<tb> 2-chloroethyl-tris (hexynyl- (3 ')
<tb> oxy) <SEP> -silane <SEP> 0.85 <SEP>
<tb> Control <SEP> (untreated) <SEP> 0 <SEP>
<tb>
The agents according to the invention are prepared in a manner known per se by intimately mixing and grinding active ingredients of the general formula I with suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active ingredients.



   Active ingredient concentrates dispersible in water, d. H.



  Wettable powders, pastes and emulsion concentrates are active ingredient concentrates that can be diluted with water to any desired concentration. They consist of active ingredient, carrier, optionally additives stabilizing the active ingredient, surface-active substances and anti-foaming agents and optionally solvents. The active ingredient concentration in these agents is 0.5 to 80%.



   The wettable powders and pastes are obtained by mixing the active ingredients with dispersants and pulverulent carriers in suitable devices until homogeneous and grinding. The following can be used as carrier materials:
Kaolin, talc, bolus, loess, chalk, limestone, lime grit, ataclay, dolomite, diatomaceous earth, precipitated silica, alkaline earth silicates, sodium and potassium aluminum silicates (feldspars and mica), calcium and magnesium sulfates, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, urea, ground vegetable products such as grain flour, tree bark flour, wood flour, nut shell flour, cellulose powder, residues from plant extractions, activated charcoal, etc., either individually or as mixtures with one another.



   The following can be used as dispersants, for example:
Condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, and alkali metal, ammonium and alkaline earth metal salts of ligninsulfonic acid, further alkylarylsulfonates, alkali metal and alkaline earth metal sulfate, alkali metal sulfates, fatty alkanolsulfates, fatty alkanolsulfates, octadolecane sulfates and octalalkanecolates, such as saline alcoholecanolsulfates, octalalkanecolates, octadolecanolsulfates, and octalalkanecolates, such as saline-alkanolsulfates, and octalolecanols Salts of sulfated fatty alcohol glycol ether, the sodium salt of oleyl methyl tauride, ditertiary acetylene glycols, di alkyldilaurylammonium chloride and fatty acid alkali and earth alkali salts.



   These mixtures can also be added to stabilize the active ingredient and / or nonionic, anionic and cationic substances, which, for example, improve the adhesion of the active ingredients to plants and parts of plants (adhesives and adhesives) and / or ensure better wettability (wetting agents).

   For example, the following can be used as adhesives:
Oleic-lime mixture, cellulose derivatives (methyl cellulose, carboxymethyl cellulose), hydroxyethylene glycol ethers of mono- and dialkylphenols with 5-15 ethylene oxide residues per molecule and 8-9 carbon atoms in the alkyl residue, ligninsulphonic acid, its alkali and alkaline earth salts, polyethyleneglycol ethers (fatty alcohol bowax ethers) 5-20 ethylene oxide residues per molecule and 8-18 carbon atoms in the fatty alcohol part, condensation products of ethylene oxide, propylene oxide, polyvinylpyrrolidones, polyvinyl alcohols, condensation products of urea-formaldehyde and latex products.

   The active ingredients are mixed, ground, sieved and passed with the additives listed above in such a way that the solid portion of the wettable powders does not exceed a particle size of 0.02 to 0.04 and of the pastes 0.03 mm
To produce emulsion concentrates and pastes, dispersants such as those listed in the preceding sections, organic solvents and water are used. The following are, for example, possible solvents:
Ketones, benzene, xylenes, toluene, dimethyl sulfoxide and mineral oil fractions boiling in the range from 120 to 350 ". The solvents must be practically odorless, non-phytotoxic and inert to the active ingredients.



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



   The solid working-up forms such as dusts, scattering agents and granules contain solid carriers, as listed above, and optionally additives that stabilize the active ingredient. The grain size of the carrier materials is expediently up to about 0.1 mm for dusts, about 0.075 to 0.2 mm for grit and 0.2 mm or more for granulates. The active ingredient concentrations in the solid work-up forms are 0.5 to 80%.



   All of the active ingredient concentrates listed can also contain light stabilizers and antioxidants.



  granules
The following substances are used to produce 5% granules:
5 parts of 2-chloroethyl-tris- (2'-chloroethoxy) -silane,
0.25 parts epichlorohydrin,
0.25 part of cetyl polyglycol ether,
3.50 parts of polyethylene glycol (Carbowax), 91 parts of kaolin (grain size 0.2-0.8 mm),
The active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution obtained in this way is sprayed onto kaolin and the acetone is then evaporated in vacuo.



   Wettable powder
To produce a) 40% and b) 50%, c) 25% and d) a 10% wettable powder, the following ingredients 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 (dodecyloxy) -silane,
5 parts of alkylarylsulfonate (Tinovetin B),
10 parts calcium lignosulfonate,
1 part of champagne-chalk-hydroxyethyl cellulose
Mixture (1: 1),
20 parts of silica,
14 parts of kaolin.



  c) 25 parts of 2-chloroethyl-tris- (4'-methoxy-b enzyloxy) silane,
5 parts of oleyl methyl tauride sodium salt,
2.5 parts of naphthalenesulfonic acid-formaldehyde
Condensate,
0.5 parts of carboxymethyl cellulose,
5 parts of neutral potassium aluminum silicate,
62 parts of kaolin d) 10 parts of 2-chloroethyl-tris (4'-chloro-benzyloxy) -silane
3 parts mixture of the sodium salts of saturated
Fatty alcohol sulfates,
5 parts of naphthalenesulfonic acid-formaldehyde
Condensate,
82 parts of kaolin.



   The active ingredients are intimately mixed with the tensile impact agents in suitable mixers and ground on appropriate mills and rollers. Wettable powders are obtained which can be diluted with water to form suspensions of any desired concentration. Such suspensions find z. B. Application for removing unwanted stinging shoots, for tillering lawns, for rooting seedlings and cuttings, etc.



   Emulsion concentrate
To produce 25% emulsion concentrates, a) 25 parts of 2-chloroethyl-tris- (benzyloxy) -silane,
5 parts mixture of nonylphenol polyoxyethylene, and calcium dodecylbenzenesulfonate,
70 parts of xylene.



  b) 25 parts of 2-chloroethyl-tris- (ethoxy) -silane,
10 parts mixture of nonylphenol polyoxyethylene and
Calcium dodecylbenzenesulfonate,
65 parts of cyclohexanone mixed together. This concentrate can be diluted to suitable concentrations with water to form emulsions. Such emulsions are suitable for thinning flowers and fruits, for accelerating the ripening of fruits and for promoting the detachment of fruits and leaves.



   Some of the ß-haloethyl silanes encompassed by the formula I have already been described [cf. Boye, F. W. et al].



   The s-bromoethyl silanes of the formula I in which X is bromine are new compounds.



   Furthermore, 8-chloroethyl-silanes of the narrower formula II
EMI7.1
 also new, not yet described compounds.



   In the formula II of the new compounds mean
Y chlorine or a radical -OR'3,
R'1, R'2 and R'3 each independently represent an alkyl radical with 6 to 18 carbon atoms, one by halogen, alkoxy, alkenyloxy, alkylthio, alkoxycarbonyl, phenoxy, cycloalkyl, by a heterocyclic radical and / or by a di - or tri-alkylammonio group substituted alkyl radical, an alkenyl or haloalkenyl, an alkynyl, a cycloalkyl radical, a phenyl radical optionally monosubstituted or polysubstituted by cyano, alkyl, haloalkyl, alkoxy, alkylthio, alkanoyl and / or alkoxycarbonyl , a benzyl radical optionally substituted one or more times by alkyl, alkoxy and / or halogen;

   one or more of the symbols R'1, R'2 and R'3 can also represent the group R4-CO-, in which R4 represents an alkyl, alkenyl or alkynyl radical, a haloalkyl or haloalkenyl radical, a through Cycloalkyl or phenyl-substituted alkyl or alkenyl radical, where phenyl can be substituted by alkyl, alkoxy and / or halogen, for an alkoxyalkyl, an alkoxycarbonylalkyl, a benzoylalkyl or a phenyl radical or a optionally substituted by halogen, lower alkyl or alkoxy 5- or 6-membered heterocyclic radical;
R'1 and R'2, even if they are present as a group -COR4, together with the adjacent oxygen atoms and the Si atom can form a saturated or unsaturated heterocyclic ring system.

 

   In formula II, alkyl radicals are to be understood as meaning straight-chain or branched radicals having 6 to 18 carbon atoms.



   In particular, straight-chain and branched alkyl radicals with 1 to 8 carbon atoms form the alkyl part of alkoxy, alkylthio, di- and tri-alkylammonium or alkoxycarbonyl substituents of an alkyl radical or of the phenyl radical.



   Haloalkyl radicals in formula II are Al exchanged for radicals of alcohols of the formulas VII, VIII, IX R'1011 (Vii) R ', OR (VIII) R130H (LX).



   If X in the starting material of the formula III is bromine, low molecular weight alkanols can also be used to replace the radicals —O — CO — R4 in formula VI.



     If none of the radicals R'1, R'2 and R'3 are identical to
EMI8.1
 the preparation of the new ß-haloethyl-silanes of the formulas I and II can be carried out according to a variant of the process by adding an ß-haloethyl-trichlorosilane of the formula III with one, two or three equivalents of one of the alcohols of the formulas VII, VIII or IX converts, and when using ß-bromoethyl-trichlorosilane as the starting material, low molecular weight alkanols with less than 6 carbon atoms can also be used for the reaction.



   In formula III, X denotes chlorine or bromine, R4 in formulas IV and V has the meaning given under formula I, and R'1, R'2 and R'3 in formulas VII, VIII and IX have the meaning given under formula II.



   Since the 3 chlorine atoms of the starting material of the formula III are exchanged in stages during the reaction, intermediate products, namely dichlorosilanes and monochlorosilanes of the formulas, can of course be used
EMI8.2
 are isolated during the synthesis or as impurities from the crude end product of the formula I or II.



   The compounds (b) were encompassed by the general formulas I and II and also show biological, plant growth-regulating properties.



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



   To achieve complete conversion, the alcohols, carboxylic acids and carboxylic acid anhydrides used as reactants, used in excess, can also serve as solvents or diluents.



   Furthermore, in some cases it may be necessary to add an acid-binding agent to the reaction mixture.



  For this purpose, tertiary amines such as trialkylamines, eg. B. triethylamine, pyridine and pyridine bases, dialkylanilines, etc. in question.



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



   The following examples serve to illustrate the preparation of some new active ingredients of the agent according to the invention. The following tables summarize further active ingredients of the formula I of the agent prepared in the way described in the examples.



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



   Example 1 a) 40.8 g of 2-chloroethyl-trichlorosilane are dissolved in 71.5 g of acetic anhydride and left to stand for 21 hours at room temperature. The reaction product is evaporated in vacuo. 44.6 g of 2-chloroethyl-tris- (acetyloxy) -silane are obtained, b.p .: 85-88 "/ 0.1 Torr, nD20 = 1.6687 (compound 1)
Calc .: 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 (acetyloxy) -silane are dissolved in 40 ml of absolute benzene. At 50-55, 10.8 g of benzyl alcohol in 20 ml of absolute benzene are added within 60 minutes. The mixture is stirred for 41/2 hours at 50-55 ".



  The reaction mixture is evaporated in vacuo and 14.3 g of 2-chloroethyl- (benzyloxy-diacetyloxy) -silane are obtained, b.p .: 125-127 / 0.001 Torr, now 20 = 1.4840 (compound 2)
Calc .: C 49.3 H 5.4 Cl 11.2 Si 8.9
Found: C 49.4 H 5.4 Cl 11.7 Si 8.9
Example 2
26.9 g of 2-chloroethyl-tris (acetyloxy) -silane obtained according to Example la are dissolved in 40 ml of absolute benzene.



  At 50-55 ", 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 41/2 hours at 50-55. The reaction mixture is evaporated in vacuo and 20.2 g of 2-chloroethyl ( di-benzyloxy) - (acetyloxy) -silane, b.p .: 164-166 / 0.005 torr, nD25 = 1.5218 (compound 3).



   Calc .: C 59.3 H 5.8 Cl 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-trichlorosilane are dissolved in 150 ml of absolute diethyl ether. At -5 to -10 ", 22.7 g of 4-chlorobenzyl alcohol are added over the course of 5 minutes, followed by 12.6 g of absolute pyridine, dissolved in 50 ml of absolute ether, over the course of 30 minutes. The mixture is stirred for a further hour at 0 and then 18 hours under reflux.



   The reaction mixture is filtered, the filtrate is washed twice with water, dried and evaporated in vacuo. 23.5 g of 2-chloroethyl-tris- (4'-chlorobenzyl oxy) -silane are obtained, b.p .: 200-210 / 0.01 Torr, nD20 = 1.5636 (compound 4), calc .: C 53.5 H 4.3 Cl 27.5 Si 5.4 Found: C 53.4 H 4.3 Cl 27.8 Si 5.6
Example 4
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 at the same temperature over the course of one hour.

   The mixture is then stirred for one hour at 0 ", 2 hours at room temperature and 18 hours under reflux. It is then filtered, the filtrate is quickly washed with ice-cold water, dried and evaporated in vacuo. 21.5 g of 2-chloroethyl-tris are obtained - [3'-chloro-butenyl- (2 ') - oxy] -silane, b.p .: 145-150 / 0.05 torr, nD20 = 1.4912 (compound 5).



   Calc .: 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
Example 5 (preparation of an intermediate product)
59.4 g of 2-chloroethyl-trichlorosilane are dissolved in 750 ml of absolute diethyl ether. At -5 to 100, a mixture of 34.9 g of hexane (1) -ol and 23.7 g of absolute pyridine, dissolved in 250 ml of absolute ether, is added within one hour. The mixture is then stirred 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) -silane, boiling point: 69-72 / 0.1 Torr, are obtained.



   Calc .: 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 2-chloroethyl-trichlorosilane are dissolved in 750 ml of absolute diethyl ether. At -5 to 100, a mixture of 69.7 g of hexane (1) -ol and 47.5 g of absolute pyridine, dissolved in 250 ml of absolute ether, is added within one hour. The mixture is then stirred for 12 hours at room temperature. It is then filtered and the filtrate is evaporated in vacuo.

   After fractional distillation, 32.5 g of 2-chloroethyl (dihexyloxy-chloro) silane, bp: 97-102 "/ 0.001 Torr, nD20 = 1.4423 (compound 6) compounds of the formula are obtained
EMI9.1
   Table I.
EMI10.1


<tb> No. <SEP> R1 <SEP> = <SEP> R2 <SEP> = <SEP> R3 <SEP> X <SEP> Physical <SEP> data
<tb> <SEP> Fp; <SEP> Kp / Torr; <SEP> nD
<tb> <SEP> 7 <SEP> Aethyl <SEP> Cl <SEP> Kp: <SEP> 80 <SEP> - <SEP> 81/14
<tb> <SEP> 8 <SEP> Aethyl <SEP> Br <SEP> Kp: <SEP> 83 <SEP> - <SEP> 4/14 <SEP>
<tb> <SEP> 9 <SEP> n-Propyl <SEP> Cl <SEP> Kp: <SEP> - <SEP> 55 <SEP> - <SEP> 60 / 0.1
<tb> <SEP> 10 <SEP> Isopropyl <SEP> Cl <SEP> Kp: <SEP> 110 <SEP> - <SEP> 113/14
<tb> <SEP> 11 <SEP> n-butyl <SEP> Cl <SEP> Kp: <SEP> 83 <SEP> - <SEP> 85 / 0.1 <SEP>
<tb> <SEP> 12 <SEP> Isobutyl <SEP> Cl <SEP> Kp:

   <SEP> 93 <SEP> - <SEP> 97 / 0.8 <SEP>
<tb> <SEP> 13 <SEP> sec.Butyl <SEP> Cl <SEP> Kp: <SEP> 80 <SEP> - <SEP> 83 / 0.5
<tb> <SEP> 14 <SEP> n-Pentyl <SEP> Cl <SEP> kp: <SEP> 108 <SEP> - <SEP> 112 / 0.1
<tb> <SEP> 15 <SEP> 2-methyl-butyl <SEP> Cl <SEP> Kp: <SEP> 115 <SEP> - <SEP> 118 / 0.2
<tb> <SEP> 16 <SEP> 3-methyl-butyl <SEP> Cl <SEP> Kp: <SEP> 96 <SEP> - <SEP> 100 / 0.1 <SEP>
<tb> <SEP> 17 <SEP> Hexyl <SEP> Br <SEP> Kp: <SEP> 145 <SEP> - <SEP> 50 / 0.01 <SEP>
<tb> <SEP> 18 <SEP> 2-ethylhexyl <SEP> Cl <SEP> nD20 = 1.4480
<tb> <SEP> 19 <SEP> 1-methyl-heptyl <SEP> Cl <SEP> nD20 = 1.4460
<tb> <SEP> 20 <SEP> Octyl <SEP> Cl <SEP> Kp: <SEP> 165 <SEP> - <SEP> 70 / 0.001
<tb> <SEP> 21 <SEP> Octyl <SEP> Br <SEP> Kp:

   <SEP> 165 <SEP> - <SEP> 70 / 0.005 <SEP>
<tb> <SEP> 22 <SEP> 1-methyl-4-ethyl-hexyl <SEP> Cl <SEP> nD20 = 1.4500
<tb> <SEP> 23 <SEP> Decyl <SEP> Cl <SEP> nD20 = <SEP> 1.4458
<tb>
EMI11.1


<tb> No. <SEP> R1 <SEP> = <SEP> R2 <SEP> = <SEP> R3 <SEP> X <SEP> Physical <SEP> data
<tb> <SEP> Fp; <SEP> Kp / Torr; <SEP> nD
<tb> 24 <SEP> Undecyl <SEP> Cl <SEP> nD20 = 1.4511
<tb> 25 <SEP> Dodecyl <SEP> Cl <SEP> nD20 = 1.4545
<tb> 26 <SEP> Dodecyl <SEP> Br <SEP> nD20 = 1.4582
<tb> 27 <SEP> tetradecyl <SEP> Cl <SEP> nD20 = 1.4543
<tb> 28 <SEP> Hexadecyl <SEP> Cl <SEP> nD20 = 1.4540
<tb> 29 <SEP> Octadecyl <SEP> Cl <SEP> + <SEP> Fp: <SEP> 33 <SEP> - <SEP> 36 <SEP>
<tb> 30 <SEP> Octadecyl <SEP> Br <SEP> | <SEP> Fp:

   <SEP> 35 <SEP> - <SEP> 36 <SEP>
<tb> 31 <SEP> 2-chloroethyl <SEP> Cl <SEP> Kp: <SEP> 123 <SEP> - <SEP> 26 / 0.001 <SEP>
<tb> 32 <SEP> 6-chlorohexyl <SEP> Cl <SEP> Kp: <SEP> 210 <SEP> - <SEP> 15 / 0.03
<tb> 33 <SEP> 2-methoxyethyl <SEP> Cl <SEP> Kp: <SEP> 103 <SEP> - <SEP> 105 / 0.05
<tb> 34 <SEP> 2-ethoxyethyl <SEP> Cl <SEP> Kp: <SEP> 122 <SEP> - <SEP> 125 / 0.005
<tb> 35 <SEP> 2-butyloxyethyl <SEP> Cl <SEP> nD20 = 1.4495
<tb> 36 <SEP> 2-allyloxyethyl <SEP> Cl <SEP> Kp: <SEP> 140 <SEP> - <SEP> 145 / 0.001
<tb> 37 <SEP> 2- (1-methylethenyloxy) ethyl <SEP> Cl <SEP> nD20 = 1.4397
<tb> 38 <SEP> 2-propyloxyethyl <SEP> Cl <SEP> Kp: <SEP> 134 <SEP> - <SEP> 138 / 0.005
<tb> 39 <SEP> 2- (1-methylethyloxy) ethyl <SEP> Cl <SEP> Kp:

   <SEP> 125 <SEP> - <SEP> 128 / 0.005
<tb> 40 <SEP> 2-hexyloxyethyl <SEP> Cl <SEP> nD20 = 1.4501
<tb> 41 <SEP> 2-ethylthioethyl <SEP> Cl <SEP> Kp: <SEP> 195 <SEP> - <SEP> 200 / 0.005
<tb> 42 <SEP> 2-octylthioethyl <SEP> Cl <SEP> nD20 = 1.4895
<tb> 43 <SEP> 1-phenylethyl <SEP> Cl <SEP> nD20 = 1.5361
<tb> 44 <SEP> 3-phenylpropyl <SEP> Cl <SEP> nD20 = 1.5340
<tb> 45 <SEP> 2-phenoxyethyl <SEP> Cl <SEP> nD20 = 1.5460
<tb> 46 <SEP> 2-propenyl <SEP> Cl <SEP> Kp: <SEP> 95 <SEP> - <SEP> 100 / 0.2
<tb> 47 <SEP> 2-butenyl <SEP> Cl <SEP> Kp: <SEP> 100 <SEP> - <SEP> 15 / 0.2
<tb> 48 <SEP> 2-butenyl <SEP> Br <SEP> Kp: <SEP> 1.15 <SEP> - <SEP> 20 / 0.01 <SEP>
<tb>
EMI12.1


<tb> No. <SEP> R1 <SEP> = <SEP> R2 <SEP> = <SEP> R3 <SEP> X <SEP> Physical <SEP> data
<tb> <SEP> Fp; <SEP> Kp / Torr;

   <SEP> nD
<tb> <SEP> 49 <SEP> 3,7-dimethyl-2-octenyl <SEP> Cl <SEP> nD20 = 1.4707
<tb> <SEP> 50 <SEP> 10-Undecenyl <SEP> Cl <SEP> nD20 = 1.4606
<tb> <SEP> 51 <SEP> 9-octadecenyl <SEP> Cl <SEP> nD20 = 1.4645
<tb> <SEP> 52 <SEP> 3,7-dimethyl-2,6-octadienyl <SEP> Cl <SEP> nD20 = 1.4682
<tb> <SEP> 53 <SEP> 2-propynyl <SEP> Cl <SEP> Kp: <SEP> 94 / 0.35
<tb> <SEP> 54 <SEP> 2-propynyl <SEP> Br <SEP> Kp: <SEP> 115 <SEP> - <SEP> 20 / 0.005 <SEP>
<tb> <SEP> 55 <SEP> 3-Hexinyl <SEP> Cl <SEP> Kp: <SEP> 170 <SEP> - <SEP> 5 / 0.005
<tb> <SEP> 56 <SEP> 1-ethynylbutyl <SEP> Cl <SEP> nD20 = 1.4715
<tb> <SEP> 57 <SEP> 3-chloro-2-butenyl <SEP> Cl <SEP> Kp:

   <SEP> 145 <SEP> - <SEP> 50 / 0.005
<tb> <SEP> 58 <SEP> 3-phenyl-2-propenyl <SEP> Cl <SEP> nD20 = 1.5832
<tb> <SEP> 59 <SEP> 3-phenyl-2-propenyl <SEP> Br <SEP> nD20 = 1.5882
<tb> <SEP> 60 <SEP> 3-cyanoethyl <SEP> Cl <SEP> nD20 = 1.4696
<tb> <SEP> 61 <SEP> ethoxycarbonyl-methyl <SEP> Cl <SEP> nD20 = 1.4492
<tb> <SEP> 62 <SEP> 1-ethoxycarbonyl (1-methyl) - <SEP> Cl <SEP> Kp: <SEP> 154 <SEP> - <SEP> 58 / 0.3
<tb> <SEP> methyl
<tb> <SEP> 63 <SEP> butoxycarbonyl-methyl <SEP> Cl <SEP> nD20 = 1.4480
<tb> <SEP> 64 <SEP> Cyclohexyl <SEP> Cl <SEP> Kp: <SEP> 165 <SEP> - <SEP> 170 / 0.001
<tb> <SEP> 65 <SEP> Cyclohexylmethyl <SEP> Cl <SEP> Kp:

   <SEP> 180 <SEP> - <SEP> 190 / 0.001
<tb> <SEP> 66 <SEP> Cyclohexylmethyl <SEP> Br <SEP> nD20 = <SEP> 1.4833
<tb> <SEP> 67 <SEP> 3-Cyclohexylpropyl <SEP> Cl <SEP> nD20 = 1.4782
<tb> <SEP> 68 <SEP> 3,4-dimethylcyclohexyl <SEP> Cl <SEP> nD20 = 1.4746
<tb> <SEP> 69 <SEP> 3,5-dimethylcyclohexyl <SEP> Cl <SEP> nD20 = 1.4673
<tb> <SEP> 70 <SEP> 4-tert-butylcyclohexyl <SEP> Br <SEP> nD20 = 1.4695
<tb> <SEP> 71 <SEP> (-) Bornenyl <SEP> Cl <SEP> nD20 = 1.4890
<tb> <SEP> 72 <SEP> 6,6-dimethylbicyclo [3.1,1,] hept- <SEP> Cl <SEP> nD20 = 1.4687
<tb> <SEP> -2-en-2-ylethyl
<tb> <SEP> 73 <SEP> Benzyl <SEP> Cl <SEP> Kp: <SEP> 190 <SEP> - <SEP> 200 / 0.001
<tb>
EMI13.1


<tb> <SEP> r. <SEP> R1 <SEP> = <SEP> R2 <SEP> = <SEP> R3 <SEP> X <SEP> Physical <SEP> data
<tb> <SEP> Fp: <SEP> Kp / Torr;

   <SEP> nD
<tb> 20
<tb> <SEP> 74 <SEP> Benzyl <SEP> Br <SEP> nD20 = <SEP> 1.5612
<tb> <SEP> 75 <SEP> 4-chlorobenzyl <SEP> Cl <SEP> Kp: <SEP> 200 <SEP> - <SEP> 20 / 0.01
<tb> <SEP> 76 <SEP> 4-chlorobenzyl <SEP> Br <SEP> nD20 = 1.5757
<tb> <SEP> 77 <SEP> 4-methoxybenzyl <SEP> Cl <SEP> nD20 = 1.5224
<tb> <SEP> 78 <SEP> 2,4-dichlorobenzyl <SEP> Cl <SEP> nD20 = 1.6637
<tb> <SEP> 79 <SEP> 4-methylbenzyl <SEP> Cl <SEP> nD20 = 1.5433
<tb> <SEP> 80 <SEP> Phenyl <SEP> Cl <SEP> nD20 = 1.5623
<tb> <SEP> 81 <SEP> 4-chlorophenyl <SEP> Cl <SEP> nD20 = 1.5769
<tb> <SEP> 82 <SEP> 3-chlorophenyl <SEP> Cl <SEP> nD27 = 1.5262
<tb> <SEP> 83 <SEP> 3,4-dichlorophenyl <SEP> Cl <SEP> nD27 = 1.5257
<tb> <SEP> 84 <SEP> 3,5-dichlorophenyl <SEP> Cl <SEP> nD27 = 1.5268
<tb> <SEP> 85 <SEP> 4-bromophenyl <SEP> Cl <SEP> nD27 = 1.5418
<tb> <SEP> 86 <SEP> 4-methoxyphenyl <SEP> Cl <SEP> nD20 = 1,

  5620
<tb> <SEP> 87 <SEP> 4-methoxyphenyl <SEP> Br <SEP> ¯20¯ <SEP> 1.5641
<tb> <SEP> 88 <SEP> 3-methoxyphenyl <SEP> Cl <SEP> nD20 = 1.5590
<tb> <SEP> 89 <SEP> 4-butyloxyphenyl <SEP> Cl <SEP> nD20 = 1.5307
<tb> <SEP> 90 <SEP> 4-tert-butylphenyl <SEP> Cl <SEP> Fp: <SEP> 75 <SEP> - <SEP> 77
<tb> 91 <SEP> 3-methylphenyl <SEP> Cl <SEP> nD27 = 1.5385
<tb> <SEP> 92 <SEP> 3-methylphenyl <SEP> Br <SEP> nD20 = 1.5490
<tb> <SEP> 93 <SEP> 3,4-dimethylphenyl <SEP> Cl <SEP> nD27 = 1.4935
<tb> <SEP> 94 <SEP> 3-formylphenyl <SEP> Cl <SEP> Fp: <SEP> 98 <SEP> - <SEP> 101
<tb> <SEP> 95 <SEP> 4-cyanophenyl <SEP> Cl <SEP> Fp: <SEP> 106 <SEP> - <SEP> 111
<tb> <SEP> 96 <SEP> 4-ethoxycarbonylphenyl <SEP> Cl <SEP> m.p .: <SEP> 112 <SEP> - <SEP> 114
<tb> <SEP> 97 <SEP> 3-ethoxycarbonylphenyl <SEP> Cl <SEP> Fp:

   <SEP> 65 <SEP> - <SEP> 70
<tb>
EMI14.1


<tb> <SEP> ¯ <SEP> ¯ <SEP> r <SEP> ffi
<tb> <SEP> No. <SEP> 1 <SEP> 2 <SEP> 3 <SEP> X <SEP> X <SEP> Physical <SEP> data
<tb> <SEP> Fpf <SEP> Kp / Torrs <SEP> nD
<tb> <SEP> LI
<tb> <SEP> 98 <SEP> ÖLoCH2- <SEP> C1 <SEP> Kp: <SEP> 195 <SEP> - <SEP> 200 / 0.001
<tb> <SEP> 99 <SEP> u <SEP> CH2- <SEP> C1 <SEP> Kp: <SEP> 152 <SEP> - <SEP> 154 "/ 0.001
<tb> <SEP> 100 <SEP> S <SEP> CH2- <SEP> Cl <SEP> 23 <SEP> 1.5771
<tb> <SEP> 101 <SEP> u <SEP> CH2- <SEP> C1 <SEP> nD5 = <SEP> 1.4727
<tb> <SEP> 2 <SEP> D
<tb> 102 <SEP> CH <SEP> W <SEP> Cl <SEP> C1 <SEP> nD = <SEP> 1.4695
<tb> <SEP> CH3 <SEP> CII <SEP> 2
<tb> <SEP> CH3
<tb> <SEP> 103 <SEP> cm:

   <SEP> oe <SEP>> <SEP> CH <SEP> - <SEP> C1 <SEP> nD = <SEP> 1.4712
<tb>
EMI15.1


<tb> <SEP> No. <SEP> R1 <SEP> = <SEP> R2 <SEP> = <SEP> R3 <SEP> = <SEP> -CO-R4 <SEP> X <SEP> Physical <SEP> Data
<tb> <SEP> R4 <SEP> is:
<tb> <SEP> 104 <SEP> Methyl <SEP> Br <SEP> Kp: <SEP> 120 <SEP> - <SEP> 122 / 0.06
<tb> <SEP> 105 <SEP> Methyl <SEP> Cl <SEP> Kp: <SEP> 85 <SEP> - <SEP> 88 / 0.1
<tb> <SEP> 106 <SEP> Aethyl <SEP> Cl <SEP> Kp: <SEP> 102 <SEP> - <SEP> 104 / 0.05
<tb> <SEP> 107 <SEP> Aethyl <SEP> Br <SEP> Kp:

   <SEP> 115 <SEP> - <SEP> 125 / 0.002 <SEP>
<tb> <SEP> 108 <SEP> isopropyl <SEP> Cl <SEP> nD20 = 1.4313
<tb> <SEP> 109 <SEP> Pentyl <SEP> Cl <SEP> nD20 = 1.4286
<tb> <SEP> 110 <SEP> 1-methylpentyl <SEP> Cl <SEP> nD20 = 1.4290
<tb> 111 <SEP> 1-ethylpentyl <SEP> Cl <SEP> nD20 = 1.4325
<tb> <SEP> 112 <SEP> Heptyl <SEP> Cl <SEP> nD25 = 1.4376
<tb> <SEP> 113 <SEP> Octyl <SEP> Cl <SEP> nD20 = 1.4332
<tb> <SEP> 114 <SEP> Undecyl <SEP> Cl <SEP> Fp: <SEP> 42 <SEP> - <SEP> 44
<tb> <SEP> 115 <SEP> Undecyl <SEP> Br <SEP> Fp: <SEP> 44 <SEP> - <SEP> 470
<tb> <SEP> 116 <SEP> Tridecyl <SEP> Br
<tb> <SEP> 117 <SEP> Pentadecyl <SEP> Cl <SEP> Fp: <SEP> 45 <SEP> - <SEP> 50 <SEP>
<tb> <SEP> 118 <SEP> Heptadecyl <SEP> Cl <SEP> Fp:

   <SEP> 54 <SEP> - <SEP> 57
<tb> <SEP> 119 <SEP> 2-propenyl <SEP> Cl <SEP> nD20 = 1.4484
<tb> <SEP> 120 <SEP> l-propenyl <SEP> Cl <SEP> Fp <SEP> = <SEP> 24 <SEP> - <SEP> 27 <SEP>
<tb> <SEP> 121 <SEP> 2-propenyl <SEP> Br <SEP> nD20 = 1.4621
<tb> <SEP> 122 <SEP> 9-decenyl <SEP> Cl <SEP> nD20 = 1.4480
<tb> 123 <SEP> 1,3-pentadienyl <SEP> Cl <SEP> Fp: <SEP> 116 <SEP> - <SEP> 1200 <SEP>
<tb> 124 <SEP> 8,11-heptadecadienyl <SEP> Cl <SEP> nD20 = 1.4705
<tb> <SEP> 125 <SEP> 2-chloroethyl <SEP> Cl <SEP> nD20 = 1.4681
<tb> <SEP> 126 <SEP> 1-bromopentyl <SEP> Cl <SEP> nD2- = 1.4513
<tb> <SEP> 127 <SEP> 10-bromodecyl <SEP> Cl <SEP> Fp:

   <SEP> 49 <SEP> - <SEP> 50
<tb>
EMI16.1


<tb> No. <SEP> R1 <SEP> = <SEP> R2 <SEP> = <SEP> R3 <SEP> = <SEP> -CO-R4 <SEP> X <SEP> Physical <SEP> data
<tb> <SEP> R4 <SEP> is:
<tb> 128 <SEP> 10-bromodecyl <SEP> Br <SEP> Fp: <SEP> 48 <SEP> - <SEP> 50
<tb> 129 <SEP> cis-2-chloroethenyl <SEP> Cl <SEP> mp: <SEP> 250
<tb> 130 <SEP> cis-2-chloroethenyl <SEP> Br <SEP> Fp: <SEP> 55 <SEP> - <SEP> 58 <SEP>
<tb> 131 <SEP> Phenylmethyl <SEP> C1 <SEP> Fp: <SEP> 74 <SEP> - <SEP> 78 <SEP>
<tb> 132 <SEP> Phenylmethyl <SEP> Br <SEP> Fp: <SEP> 20 <SEP> - <SEP> 30 <SEP>
<tb> 133 <SEP> 2-phenylethyl <SEP> Cl <SEP> Fp: <SEP> 35 <SEP> - <SEP> 39 <SEP>
<tb> 134 <SEP> 4-chlorophenylmethyl <SEP> CI <SEP> Fp: <SEP> 99 <SEP> - <SEP> 103 <SEP>
<tb> 135 <SEP> 3-methylphenylmethyl <SEP> Cl <SEP> Fp:

   <SEP> 57 <SEP> - <SEP> 60 <SEP>
<tb> 136 <SEP> 3- (4'-methoxyphenyl) -ethyl <SEP> Cl <SEP> mp: <SEP> 98 <SEP> - <SEP> 102
<tb> 137 <SEP> 4-ethoxycarbonylbutyl <SEP> Cl
<tb> 138 <SEP> 3-oxobutyl <SEP> Cl <SEP> nD20 = 1.4590
<tb> 139 <SEP> 3-oxobutyl <SEP> Br <SEP> nD20 = 1.4841
<tb>
EMI17.1


<tb> <SEP> No. <SEP> lll <SEP> - <SEP> R2 <SEP> 1: 3 <SEP> CO-R, = <SEP> CO-R4
<tb> <SEP> R4 <SEP> is <SEP> X <SEP> PizysS <SEP> aliscllc <SEP> is:
<tb> <SEP> 140 <SEP> S-Pìwe.nyl-5 <SEP> c), o <SEP> -o ': onLy1 <SEP> Cl <SEP> Fp: <SEP> 73-75
<tb> <SEP> 20
<tb> <SEP> 141 <SEP> 2-Aetho'tyathyl <SEP> Cl <SEP> n20 <SEP> = <SEP> 1,4365
<tb> <SEP> 142 <SEP> 3 <SEP> 3 "1) henoaiypl <SEP> opyl <SEP> Cl <SEP> Bp: <SEP> 58-60
<tb> <SEP> 1431 <SEP> 2,4-dich] .orepheno: symethyl <SEP> Cl <SEP> Fp:

   <SEP> 1400
<tb> <SEP> 144 <SEP> 2nd, <SEP> 4-dichloropbeno: .yraetl <SEP> yl <SEP> 13r <SEP> Fp: <SEP> 137 <SEP> -138
<tb> <SEP> 145 <SEP> 2- <SEP> (4 <SEP> to- <SEP> 1-Chlorphcnyl) -l-athenyl <SEP> Cl
<tb> <SEP> 146 <SEP> 2.Phcny1-i-.atheny1 <SEP> Cl <SEP> Fp: <SEP> 128-130
<tb> <SEP> 147 <SEP> 2-P1'-enyi-l-ätbenyl <SEP> Br <SEP> FI>: <SEP> 129-131
<tb> <SEP> 148 <SEP> 2 (31.4 <SEP> -Dj.chlorphenyl) - <SEP> I
<tb> <SEP> ¯ithc.nyl. <SEP> C1 <SEP> Fp: <SEP>> 23) 50
<tb> <SEP> 149 <SEP> 2 <SEP> w <SEP> re <SEP> 1-Mcthoxyphcnyl-1-Ethenyl <SEP> C1 <SEP> Fp:

   <SEP> 1780
<tb> <SEP> 150 <SEP> Cyclo1exyhnthy1 <SEP> C1 <SEP> n20 <SEP> = <SEP> 1, <SEP> S1494
<tb> <SEP> 151 <SEP> C5cloheXylmet <SEP> h <SEP> r> r <SEP> i; 90 <SEP> = <SEP> 1.4592
<tb> <SEP> 152 <SEP> CycLolicxyl. <SEP> l <SEP> C1 <SEP> n20 <SEP> 3, <SEP> 1.4578
<tb> <SEP> 153 <SEP> Cyclopi: opyi <SEP> C1 <SEP> n20 <SEP> - <SEP> J <SEP> 4515
<tb> 154 <SEP> 3-Cyclola <SEP>; e.nyl <SEP> C1 <SEP> n90 <SEP> - <SEP> 1 <SEP> 4740
<tb> <SEP> 155 <SEP> 3- <SEP> B1: <SEP> la <SEP> =
<tb> <SEP> 156 <SEP> i <SEP> C8551 <SEP> Q1 <SEP> n? 0 <SEP> D <SEP> 5632.
<tb> 156 <SEP> Iicnyl <SEP> cl <SEP> 20
<tb> <SEP> = <SEP> '- <SEP> i,) E> 32
<tb> <SEP> 157 <SEP> 4 <SEP> Chlorpllenyl <SEP> F1i: <SEP> Ep: <SEP> 233
<tb> <SEP> 158 <SEP> 4-Meho'yphcnyl <SEP> 1 <SEP> Bit <SEP> p: <SEP> 177J.780
<tb> <SEP> 159 <SEP> 4-ethyl.phcnyl <SEP> C1 <SEP> Fp:

   <SEP> 165-170
<tb> <SEP> 16Q <SEP> CS <SEP> Br
<tb> <SEP> 161 <SEP> C <SEP> Br <SEP> Fp: <SEP> 123-126
<tb> <SEP> 162 <SEP> Bit <SEP> Fp: <SEP> l23l25o
<tb> <SEP> 163 <SEP> LlN) L <SEP> Ci
<tb> Table III
EMI18.1


<tb> <SEP> No. <SEP> R1 <SEP> R2 <SEP> R3 <SEP> = <SEP> CO-R4 <SEP> X <SEP> Physical
<tb> <SEP> R4 <SEP> is:
<tb> <SEP> 166 <SEP> Benzyl <SEP> = <SEP> R3 <SEP> Methyl <SEP> Cl <SEP> Kp: <SEP> 126 <SEP> - <SEP> 27 / 0.001 <SEP>
<tb> <SEP> 167 <SEP> Benzyl <SEP> = <SEP> R3 <SEP> Methyl <SEP> Br <SEP> Kp: <SEP> 140-143 / 0.01 <SEP>
<tb> <SEP> 168 <SEP> Benzyl <SEP> Benzyl <SEP> Methyl <SEP> Cl <SEP> Kp: <SEP> 164-166 / 0.005
<tb> <SEP> 169 <SEP> Aethyl <SEP> Aethyl <SEP> Methyl <SEP> Cl <SEP> Kp: <SEP> 62-65 / 0.01
<tb> <SEP> 170 <SEP> Pentyl <SEP> Pentyl <SEP> Methyl <SEP> Br <SEP> Kp:

   <SEP> 104-110 / 0.001 <SEP>
<tb> <SEP> 171 <SEP> Octyl <SEP> = R3 <SEP> Methyl <SEP> Cl <SEP> Kp: <SEP> 115-120 / 0.02
<tb> <SEP> 172 <SEP> Octyl <SEP> Octyl <SEP> Methyl <SEP> Cl <SEP> Kp: <SEP> 150-152 / 0.005 <SEP>
<tb> <SEP> 173 <SEP> 2-butynyl <SEP> 2-butynyl <SEP> methyl <SEP> Cl <SEP> Kp: <SEP> 108-110 / 0.02 <SEP>
<tb> <SEP> 174 <SEP> 2-butenyl <SEP> 2-butenyl <SEP> methyl <SEP> Cl <SEP> Kp:

   <SEP> 94-98 / 0.001
<tb> <SEP> 175 <SEP> 4-chlorine
<tb> <SEP> benzyl <SEP> = <SEP> R3 <SEP> Aethyl <SEP> Cl <SEP> nD20 = 1.4940
<tb> <SEP> 176 <SEP> 4-chlorine <SEP> benzyl <SEP> = <SEP> R3 <SEP> Aethyl <SEP> Br <SEP> # <SEP> nD20 = 1.5042
<tb> <SEP> 177 <SEP> 3.7-Dime
<tb> <SEP> ethyl-7
<tb> <SEP> @etenyl <SEP> <SEP> = <SEP> R3 <SEP> Aethyl <SEP> Cl <SEP> nD20 = 1.4525
<tb> <SEP> 178 <SEP> 4-methoxy <SEP> benzyl <SEP> = <SEP> R3 <SEP> Aethyl <SEP> Cl <SEP> nD20 = 1.4890
<tb> Table IV
EMI19.1


<tb> No. <SEP> R1 <SEP> R2 <SEP> R3 <SEP> X <SEP> Anion <SEP> Physical
<tb> I <SEP> data
<tb> <SEP> CH3 \ 63 <SEP> (3
<tb> 179 <SEP> CH3 <SEP> H <SEP> Hexyl <SEP> Hexyl <SEP> Cl <SEP> Cl <SEP> Fp:

   <SEP> 25 <SEP> - <SEP> 35 <SEP>
<tb> <SEP> CH3 / 4
<tb> <SEP> 180 <SEP> -CH2CH2- <SEP> Benzyl <SEP> Benzyl <SEP> Cl <SEP> Cl <SEP> n20 <SEP> = <SEP> 1> 5212
<tb> CP <SEP> D
<tb> Table V compounds in which R1 and R2 together with the neighboring atoms form a @Si-containing heterocycle).
EMI20.1


<tb>



   <SEP> No. <SEP> connection <SEP> physical <SEP> data
<tb> <SEP> OC, H13
<tb> <SEP> CII <SEP> CB2 <SEP> - <SEP> 0 \ I
<tb> <SEP> 181 <SEP> \ <SEP> CH3 \ (<SEP> 3C <SEP>, ski <SEP> - <SEP> CH2-CH2-C1 <SEP> Kp: <SEP> 115-1200 / 0.005
<tb> <SEP> CII <SEP> C11 <SEP> - <SEP> 0
<tb> <SEP> 3 <SEP> 2
<tb> <SEP> 0
<tb> 182 <SEP> ll2 <SEP> 1 <SEP> D25 <SEP> - <SEP> 1.5233
<tb> <SEP> II
<tb> <SEP> OC2 <SEP> s
<tb> <SEP> L
<tb> <SEP> OC, HII.
<tb>



   <SEP> 183 <SEP> i <SEP> C5Hll <SEP> hD = <SEP> 1.4718
<tb> <SEP> CO- <SEP> 0? C.Hll <SEP> 20 = <SEP> 1> 4537
<tb> <SEP> 184 <SEP> $ i <SEP> COO / S <SEP> -CH2-C112-Cl <SEP> nD
<tb> <SEP> 0
<tb> <SEP> 185 <SEP> () 0 {00; s'i-CII2-C112-Cl <SEP> CC6H13 <SEP> nD = <SEP> 1.4400
<tb> <SEP> C0
<tb> <SEP> 186 <SEP> Si <SEP> - <SEP> CN <SEP> -CH2'CZ <SEP> and <SEP>, 4502
<tb> <SEP> OC6H13
<tb> Table VI Compounds of the formula I in which Y is chlorine.
EMI21.1


<tb>



  No. <SEP> R1 <SEP> = <SEP> R2 <SEP> X <SEP> Physical <SEP> data
<tb> 187 <SEP> Hexyl <SEP> Cl <SEP> Kp: <SEP> 97 <SEP> - <SEP> 102 / 0.001
<tb> 188 <SEP> Hexyl <SEP> Br <SEP> nD20 <SEP> 1.4532
<tb> <SEP> 189 <SEP> Octyl <SEP> Cl <SEP> nD20 = 1.4479
<tb> <SEP> 190 <SEP> 2-butenyl <SEP> Cl <SEP> nD20 = 1.4678
<tb> <SEP> 191 <SEP> 3-hexinyl <SEP> Cl <SEP> nD20 = 1.4764
<tb> 192 <SEP> 6-chlorohexyl <SEP> Cl <SEP> nD20 = 1.4707
<tb> <SEP> 193 <SEP> 2-ethoxyethyl <SEP> Cl <SEP> Kp:

   <SEP> 87 <SEP> - <SEP> 92 / 0.001 <SEP>
<tb> <SEP> 194 <SEP> 3-phenylpropyl <SEP> Cl <SEP> nD20 = 1.5192
<tb> <SEP> 195 <SEP> Dodecyl <SEP> Cl <SEP> nD20 = 1.4564
<tb> <SEP> 196 <SEP> Cyclohexyl <SEP> Cl <SEP> nD20 = 1.4836
<tb> <SEP> 197 <SEP> Cyclohexylmethyl <SEP> Cl <SEP> nD20 = 1.4766
<tb> <SEP> 198 <SEP> Benzyl <SEP> Cl <SEP> nD20 = 1.5265
<tb> <SEP> 199 <SEP> 4-chlorobenzyl <SEP> Cl <SEP> nD20 = 1.5552
<tb> <SEP> 200 <SEP> 4-methylbenzyl <SEP> Cl <SEP> nD20 = 1.5343
<tb> <SEP> 201 <SEP> 4-methoxybenzyl <SEP> Cl <SEP> nD20 = 1.5455
<tb> <SEP> 202 <SEP> 3-methylphenyl <SEP> Cl <SEP> nD20 = 1.5372
<tb> <SEP> 203 <SEP> 3-methoxyphenyl <SEP> Cl <SEP> nD20 = 1.5486
<tb>


    

Claims (1)

PATENT CLAIMS I. Agent for regulating plant development, characterized in that there is at least one β-haloethyl silane of the formula I as the active component EMI22.1 contains, in the Y chlorine or a residual OR3, X chlorine or bromine, R1, R2 and R3 independently of one another are alkyl radicals, by halogen, alkoxy, alkenyloxy, phenyl, phenoxy, cyano, cycloalkyl, cycloalkenyl, alkylthio, alkoxycarbonyl, by at least one heterocyclic radical and / or by di- and tri-alkylammonio-substituted alkyl radicals, alkenyl , Phenylalkenyl, haloalkenyl, alkynyl, cycloalkyl and cycloalkenyl radicals, optionally phenyl radicals monosubstituted or polysubstituted by cyano, nitro, alkyl, halogen, haloalkyl, alkoxy, alkylthio, alkanoyl and / or alkoxycarbonyl, optionally by alkyl, Alkoxy and / or halogen are mono- or polysubstituted benzyl radicals, one or more of the symbols R1, R2 and R3 also denote the group - C C! "means in which R4 represents an alkyl, oxoalkyl, alkenyl or alkynyl radical, a haloalkyl or haloalkenyl radical, an alkyl radical substituted by cycloalkyl, phenyl or phenoxy or an alkenyl radical substituted by cycloalkyl or phenyl, where the Phenyl radicals can be substituted by alkyl, alkoxy and / or halogen, furthermore for a phenyl-oxoalkyl, an alkoxyalkyl, an alkoxycarbonylalkyl, a cycloalkyl or cycloalkenyl radical or a phenyl radical optionally substituted by halogen, lower alkyl or alkoxy and finally for a 5 or 6-ring membered heterocyclic radical, also R, and R2 together with the adjacent oxygen atoms and the Si atom can form a saturated or unsaturated heterocyclic ring system. II. Use of the agent according to claim I to improve the abscission of fruits and leaves, to accelerate ripening and to promote the flow of resin in trees.