DE2149680A1 - Concrete tub used for regulating plant growth - Google Patents

Description

AGRIPAT S.A.

CH-4000 Base! 21 (Switzerland / Switzerlanc!)

Dr. F. Zumstein Sr. - Dr. E. Ä3smartn ** I ^ VWUU

Dr. R. Koenigsberger - Dipf. Phys. R. Holzbauer

Dr. F. Ztirnsi & m jun.

Patent attorney "

8 Munich 2, BräuhausMrcße 4 / lit

5-3415 / APT / 1 + 2

Means for regulating plant growth

The present invention relates to new means and methods for regulating plant growth using of ß-Halogenäthylsilanen as active ingredients, also new ß-haloethylsilanes and process for the preparation these silanes.

The ß-haloethylsilanes contained in the new agents as active ingredients correspond to the formula I:

'0 - R ₁
X-CH ₂ - CH ₂ - Si -0 - R ₂ (i)

I γ

In this formula:

X chlorine or bromine

Y chlorine or the remainder -OR ₃ ,

R, f R _? and Ro independently of one another are alkyl radicals

Halogen, alkoxy, alkenyloxy, phenoxy, cycloalkyl, alkylthio, alkoxycarbonyl, by a heterocyclic radical and / or alkyl radicals substituted by di- and tri-alkylammonio,

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Alkenyl or haloalkenyl, alkynyl, cycloalkyl, optionally by cyano, nitro, alkyl, haloalkyl, alkoxy, alkylthio, alkanoyl and / or alkoxycarbonyl or polysubstituted phenyl radicals, optionally one or more times by alkyl, alkoxy and / or halogen substituted benzyl radicals;

one or more of the symbols R,, R "and R-, can also be the Group -COR, in which R, represents an alkyl, alkenyl or alkynyl radical, a haloalkyl or haloalkenyl radical, an alkyl or alkenyl radical substituted by cycloalkyl or phenyl, where phenyl is substituted by alkyl, alkoxy and / or halogen may be substituted, furthermore for an alkoxyalkyl, an alkoxycarbonylalkyl, a benzoylalkyl or a phenyl radical, which latter can optionally be substituted by halogen, lower alkyl or alkoxy and finally for one 5- or 6-membered heterocyclic radical.

R _{1 and} R ", also with the meaning of -COR", can, together with the neighboring atoms, also form a silicon-containing saturated or unsaturated heterocyclic ring system.

Alkyl radicals in formula I are straight-chain or branched ones To understand radicals with 1 to 18 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, η-butyl, sec-butyl, n-hexyl, n-octyl, n-dodecyl, n-octadecyl, etc. In particular the straight-chain and branched alkyl radicals with 1 to 8 carbon atoms form the alkyl substituents or the alkyl part of alkoxy, alkylthio, di- and tri-alkylammonio or alkoxycarbonyl substituents an alkyl radical or a phenyl radical. Haloalkyl radicals are alkyl radicals with 1 to 6 carbon atoms, which can be substituted by fluorine, chlorine and / or bromine, such as trifluoromethyl, 2-chloroethyI, 6-chlorohexyl etc. Alkenyl radicals in the formula I understood straight-chain or branched radicals with 3 to 18 carbon atoms, e.g. propenyl, butenyl, octenyl, decenyl, heptadecenyl Leftovers. These alkenyl residues can be one or more times by Halo-

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conditions such as fluorine, chlorine, bromine and / or iodine may be substituted. Alkenyl radicals with 3 to 6 carbon atoms form the alkenyl part of alkenyloxy residues. Alkynyl radicals preferably have 3 to 8 carbon atoms in a straight chain, such as 2-propynyl, 2-butynyl or 3-hexynyl. Among cycloaliphatic residues are to be understood as mono- or polycyclic cycloalkyl or cycloalkenyl radicals with 3 to 12 carbon atoms, such as e.g. Cyclopropyl, Cyclopentyl, Cyclopentenyl, Cyclohexenyl, BicycJbheptyl, Etc.

5- or 6-membered heterocyclic radicals R, or as substituents of alkyl radicals R ,, R _? and R ~ can contain 1 or heteroatoms, in particular nitrogen and / or oxygen, heterocyclic ring systems containing the Si atom, which are formed by the radicals R and R2 including the -COR / type, can be saturated or unsaturated; the hydrocarbon bond is therefore alkylene or alkenylene.

As anions of the di- and tri-alkylammonio radicals (which can be regarded as salt forms of a dialkylamino radical) are in particular those of hydrohalic acids, alkylsulfonic acids and alkyl phosphoric acids.

The ß-Hala'thylsilane of the formula I influence the growth of above and below ground parts of plants in different ways, they are not phytotoxic in the usual use 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 various parts of the plant. It is known that the plant itself is also in different stages of development in untereil! odl i cm mass Acthylon produces, in particular

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before and during the ripening process of the fruit and at the end of the vegetation period when the fruit and leaf peel off. Since influencing ripening, fruit detachment and leaf detachment by chemical substances for fruit, citrus fruit, pineapple and tree wo11 cultivation has economic importance, one looked for compounds with which one could achieve such effects, without causing any damage to the treated plants. So are different classes of substances in the meantime became known, with which individual such, growth-influencing effects could be achieved, however, their range of activity 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 the South African patent no. 68/1036 ß- Halogenäthylphosphonic acid derivatives are described as active ingredients regulating plant growth. These compounds decompose in and on the plant with the release of ethylene and are therefore similar to ethylene in terms of their effect and range of effects. Due to 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 application range of these active ingredients with regard to phytotoxic effects. In addition, the storage of such sensitive active ingredient concentrates is associated with difficulties.

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

US Patent 3,183,076 describes α-chloroethyl-methyldialkoxy-silanes, which are used to promote germination, leaf peeling, etc. can.

The present invention relates to new agents containing ß-haloethylsilanes as active ingredients which have a stimulating or retarding effect on plant growth in the various stages of plant development. Due to the very good stability of the active ingredients of the formula I, these agents need, in addition to the usual carriers, Distribution agents, light and oxidation stabilizers No stabilizing acid addition is necessary and is therefore applicable without restriction. With the new means, vegetative plant growth and germination are influenced, the flower formation, the fruit development and the training. promotion of separation tissues. In monocots there was an increase in tillering and branching with a simultaneous decrease in length growth. Besides that the supporting tissue of the stems of the treated plants was strengthened. The formation of unwanted stinginess in different types of plants it is very strongly reduced. Furthermore, rubber trees are becoming a major failure of latex uss stimulates, an effect that is great economic Has meaning. As experiments have shown, the rooting of seedlings and cuttings, as well as the formation of tubers promoted for potatoes. In addition, dormant rhizomes sprout at the same time, which is particularly important

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with various perennial weeds such as couch grass, Johnsongrass and Cyperus, which can then be easily destroyed or contained by herbicides. The germination capacity of Seeds, such as seed potatoes and legumes, are encouraged at lower concentrations and prevented at higher concentrations. 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 the number of flowers. This effect plays a particularly important role in pineapples. If all the bushes bloom at the same time, so the harvesting of the bushes can be compared within one . short time. With cucurbits there is a shift in the sex differentiation in favor of the female flowers.

Tests also showed that fruit trees thinned out blossoms and fruit. Continue to be e.g. in apples, pears, peaches, tomatoes, bananas and pineapples accelerates fruit ripening and coloration and improved. Through the formation of separation tissue the fruit and leaf abscission is made much easier. This is of great economic importance for the mechanical ^ see harvest, e.g. of citrus fruits or cotton. at Ornamental plants such as chrysanthemums, rhododendrons, carnations and roses are defoliated in 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 stage of development of the plant and the application concentration. But these factors are again different depending on the type of plant and the desired effect. So you will for examplex7ei.se lawns during treat the entire growing season; Ornamental plants, in which, for example, the intensity and number of flowers are to be increased before the flower system is formed; Plants whose fruits are used respectively. be recycled

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immediately after flowering or at a corresponding distance before harvest. The application of the active ingredients takes place in the form of solid or liquid means both above ground Plant parts as well as in the ground or on the ground. Application to the above-ground parts of the plant is preferred, for which solutions or aqueous dispersions are best suited. For the treatment of the growth substrate (of the soil), besides solutions and dispersions, dusts, granulates and grit are also suitable.

The plant growth-regulating effect of the inventions measured Means can often be favorably influenced by the addition of organic or inorganic acids or bases, such as 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 onto branches with good fruit hangings from various orange trees as solutions in concentrations of 0.2% - 0.4 % . After 14 days, the experiments were carried out according to that of WC Wilson and CH. Hexidershott developed method, see Proc. At the. Soc. Hoard. Sc. 9p , - · 123-129 (1967) evaluated. Here, the force to be used to remove a fruit is determined in kg.

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Active ingredient: concentration Force in kg 2-chloroethyl-tris- (ethoxy) - 0.2 % 4.5 silane 0.4% 1.5 2-chloroethyl-tris- (octyl- 0.2 % 3.7. oxy) silane 0.4 % * 2-chloroethyl-tris- (benzoxy) - 0.2 % * silane 0.4 % * 2-chloroethyl-tris- (dodecyl- 0.2 % 4.7 oxy) silane 0.4 % 1.1 control 8.6

*) The fruits hanging on the tree could be left like this easily remove that no measurement could be made.

Equally good and significant values were found with
Means containing the following compounds scored:

2-chloroethyl 2-chloroethyl-2-chloroethyl 2-chlorosfhylsilane

2-chloroethyl 2-chloroethyl-2-chloroethyl- 2-chloroethyl-2-chloroethyl 2-chloroethyl-2-chi or al: hy] -

• tris- (2'-chloroethoxy) -silane ■ tris- [butenyl- (2 ') -oxy] -silane tris- [propenyl- (2 ') - oxy] -silane tris- [3' -chlorobutenyl- (2 ') - oxy] -

tris (octadecyloxy) silane tris [butynyl (2 ') oxy] silane tris [hexynyl (3 ') oxy] silane tris- (6'-chlorohexyloxy) -silane tris- (4'-methoxy-benzoxy) -silane tris- (2 ', 4' -dichlorbo.nzoxy) -silane tris- (4'-chlorobenzoxy) -silane 209816/1770

- Sir -

,, uu, * 2H9680

On bean leaf segments it was observed that the 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 during 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 abscesses that occurred (= constriction of the stem at the abscission zone on the leaf side). The evaluation was carried out according to a grading system of 1-9, whereby Grade 9 = 0 and Grade 1 = 8 corresponds to absenteeism.

Active ingredient Need
ID card
1. en
rectification
2.. - 1 Rating after
6 days 2-bromoethyl-tris- 1 1 1 (benzoxy) silane 1 2-chloroethyl-tris- 1 1 1 (4'-chlorobenzoxy) -silane 1 2-chloroethyl-tris- 1 1 1 (octadecyloxy) silane 2-bromoethyl-tris- 1 1 [butenyl (2 ') oxy] silane 2-chloroethyl-tris- (4'- 1 1 methoxyphenoxy) -silane 2-chloroethyl-tris- 1 1 (carbobutoxyrnethoxy) - silane

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/ 2U9680

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'-chlorobenzoxy) -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- (benzoxy) -silane
2-chloroethyl-tris- (l'-carbäthoxyäthyloxjO -silan 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 ' -dimethylocteny1- (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.

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"2U9680

The acceleration of ripening was demonstrated on tomato plants in the following way:

Tomato plants of the Fournaise variety were taken in the open air Pulled plastic film. After reaching a height of The tip of the shoots was cut off 1.5 m from the plants. When the first fruits turned reddish in color, the plants became Sprayed over with aqueous preparations made from emulsion concentrates of the active ingredients mentioned below. There were 4 Plants treated with 1.5 It spray mixture, the one in the Brlihe active ingredient contained a concentration of 2000 ppm resp. 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 lowest umbels are harvested. The sums of the yield amounts obtained here are as follows Table summarized:

Active ingredient amount of effort
(ppm) Ripe fruit yield
from 3 harvests % of total
harvest Weight in kg 61.2
71.5 2-chloroethyl-tris (octyl-
oxy) silane 2000
4000 4.05
5.76 73.7
75.9 2-chloroethy1-tris (benz-
yloxy) silane 2000
4000 5.66
6.26 85.2
84.3 2-chloroethyl-tris (3'-
chlorobutenyl- (2 ') -oxy) -
silane 2000
4000 5.92
6.50 63.4
75.3 2-chloroethyl-tris (butene
yl- (2 ') -oxy) -silane 2000
4000 5.03
6.06 70.6
87.7 2-chloroethyl-tris (4'-
methoxy-benzyloxy) silate 2000
ι 4000 5.50
7.30 62.9
82.4 2-chloroethyl-tris (4'-
chlorobenzyloxy) silane 2000
4000 3.37
6.80 77.7
85.2 2-Ch] oräthyl-tris (hexi-
nyl- (3 ') - oxy) -silane 2000
4000 5.32
5.94 52.0 unresponsive] to control 1 c 3.41

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A 2U9680

The flow of resin associated with the release of latex from rubber trees can be related, was stimulated on 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 on 4 different
Trees repeated..4 weeks after application, the expelled Har ?; pr> rfp - »- nt- nnrl weighed. T) i ρ -f ni gPTirfp Tab P. 11 e gives average values in grams of resin per treated branch.

Active ingredient Amount of resin in grams , 2-bromoethyl-tris (ethoxy) -silane 0.37 2-chloroethyl-tris (4'-methoxy-
phenoxy) silane 1.81 2-chloroethyl-tris (propynyl- (2 ') -
oxy) silane 0.53 2-chloroethyl-tris (4'-chlorobenzyl-
oxy) silane 0.52 2-chloroethyl-tris (hexynyl- (3 ') -
oxy) silane 0.85 Control (untreated) 0

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The agents according to the invention are produced in a manner known per se by intimately mixing and grinding active ingredients of the general formula I with suitable ones Carriers, optionally with the addition of dispersants or solvents which are inert towards the active ingredients.

Active ingredient concentrates dispersible in water, i.e. wettable powders, pastes and emulsion concentrates are active ingredient concentrates that contain Water can be diluted to any desired concentration. They consist of active ingredient, carrier, given if the active ingredient stabilizing additives, surface-active substances and anti-foaming agents and given if solvents. The concentration of active substances in these Average is 0.5-80%.

The wettable powders and pastes are obtained by mixing the active ingredients with dispersants and powdery carriers in suitable Devices mixed and ground to homogeneity. For example, the following are used as carriers Question:

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Kaolin, talc, bolus, loess, chalk, limestone, lime grit, Ataclay, dolomite, diatomaceous earth, precipitated silica, earth alkali 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 meal, Wood flour, kiss shell flour, cellulose powder, residues of plant extractions, activated charcoal, etc., 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 as well as alkali, ammonium and alkaline earth salts of ligninsulphonic acid, further alkylarylsulphonates, Alkali and alkaline earth metal salts of dibutylnaphthalene sulfonic acid, fatty alcohol sulfates, such as sulfated salts Hexadecanols, heptadecanols, octadecanols and salts of sulfated fatty alcohol glycol ether, the sodium salt of oleyl methyl tauride, ditertiary acetylene glycols, dialkyldilaurylammonium chloride and fatty acid alkali and Alkaline earth salts.

These mixtures can also contain additives stabilizing the active substance and / or nonionic, anionic active substances and cation-active substances are added, for example, the adhesive strength of the active ingredients on plants and Improve plant parts (adhesives and adhesives) and / or ensure better wettability (wetting agent). For example, the following can be used as adhesives:

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ÄgnpatS.Ä. -

/ ς 2H9680-

Olein-ralk mixture, cellulose derivatives (methyl cellulose, . Carboxymethyl cellulose), hydroxyethylene glycol ether of Mono- and dialkylphenols with 5-15 ethylene oxide residues per molecule and 8-9 carbon atoms in the alkyl residue, lignin sulfonic acid, their alkali and alkaline earth salts, polyethylene glycol ethers (Carbowaxe), fatty alcohol polyglycol ethers with 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, Urea formaldehyde condensation products as well as latex products. The active ingredients are mixed, ground and sieved with the additives listed above And it happens that with wettable powders the solid portion has a grain size of 0.02 to 0.04 and with pastes of Does not exceed 0.03 mm.

For the production of emulsion concentrates and pastes, disYgants are used, as described in the preceding Sections listed were organic solvents and water used. Examples of solvents are used the following in question:

Ketones, benzene, xylenes, toluene, dimethyl sulfoxide and im Mineral oil fractions boiling in the range from 120 ° to 350 °. The solvents must be practically odorless, not phytotoxic, and be inert to the active ingredients.

Furthermore, the agents according to the invention can be used in Form of solutions are used .. For this purpose, the active ingredient bzv7. are several active ingredients of the general formula I dissolved in suitable organic solvents, solvent mixtures or water. As an organic solvent can aliphatic and aromatic hydrocarbons, their chlorinated derivatives, e alky! naphthalenes, mineral oils

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ÄgnpaiS.Ä. - Eat -

can be used alone or as a mixture with one another. The solutions should contain the active ingredients in a concentration range from 1 to 20% included.

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

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

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granules

The following substances are used to produce 5% granules:

5 parts of 2 ~ chloroethyl-tris- (2'-chloro-

* ethoxy) - silane,

0.25 parts of epichlorohydrin, 0.25 parts of cetyl polyglycol ether , 3.50 parts of polyethylene glycol ("Carbowax"), parts of kaolin (grain size 0.2-0.8 ram).

The active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone, then polyethylene glycol is added and cetyl polyglycol ether added. The solution obtained in this way is sprayed onto kaolin and then the acetone evaporates in vacuo.

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Wettable powder

To produce a) 40% and b) 50%, c) 25 7oigen and d) a 10% wettable powder are the following Ingredients 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 champagne chalk - hydroxyethyl

cellulose mixture (1: 1), 20 parts 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 naphthalenesulfonic acid formaldehyde

^ Condensate,

0.5 parts of carboxymethyl cellulose sols,

5 parts neutral potassium aluminum silicate j

62 parts of kaolin

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

silane

3 parts mixture of the sodium salts of saturated fatty alcohol sulfates, 5 parts of naphthalenesulfonic acid formaldehyde

Condensate,
82 parts of kaolin.

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The active ingredients are intimately mixed with the additives in suitable mixers and adjusted accordingly Grind mills and rollers. This gives wettable powders which, with water, form suspensions of any desired concentration let it dilute. Such suspensions are used, for example, to remove undesirable stinging instincts, for tillering lawns; for rooting seedlings and cuttings, etc.

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Emulsion concentrate

For the production of 25% emulsion concentrates will

a) 25 parts of 2-chloroethyl-tris ~ (benzoxy) -silane,

5 parts mixture of nonylphenol polyoxy

ethylene, and calcium dodecylbenzene sulfonate,
70 parts of xylene.

b) 25 parts of 2-chloro "ethyl ~ tris- (ethoxy) -silane, W 10 parts of a mixture of nonylphenol polyoxy-

ethylene and calcium dodecylbenzenesulfonate,
65 parts of cyclohexanone

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

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

The ß-bromoethyl silanes of the formula I in which X is bromine means are new connections.

Furthermore, ß-chloroethyl silanes of the narrower formula II

0 - R ^

Cl -CH-CH ₉ -Si-OR ¹ (H) 2 2, 2

Y
also new, not yet described compounds.

In the formula II of the new compounds mean

Y chlorine or a residue -OR'n,

R'J ^ R ¹ 2 and

R 'independently of one another each have an alkyl radical

6 to 18 carbon atoms, one by halogen, alkoxy, alkenyloxy, alkylthio, alkoxycarbonyl, Phenoxy, cycloalkyl through a heterocyclic radical and / or through a di- or tri-alkylammonio group substituted alkyl radical, an alkenyl or haloalkenyl, an alkynyl, a cycloalkyl radical,

one optionally by cyano, alkyl, haloalkyl, Alkoxy, alkylthio, alkanoyl and / or alkoxycarbonyl monosubstituted or polysubstituted Phenyl residue,

a benzyl radical which is optionally monosubstituted or polysubstituted by alkyl, alkoxy and / or halogen; one or more of the symbols R ,, R «and R- can also represent the group R / -CO- in which R, for an alkyl, alkenyl or alkynyl radical, a haloalkyl or haloalkenyl radical, a alkyl or alkenyl radical substituted by cycloalkyl or phenyl, where phenyl is substituted by alkyl,

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Alkoxy and / or halogen may be substituted, for an alkoxyalkyl, an alkoxycarbonylalkyl, a benzoylalkyl or an optionally halogen-substituted lower alkyl or alkoxy Phenyl radical or a 5- or 6-membered heterocyclic radical;

R ¹ . and R ¹ "- also in the meaning of -COR ^ can, together with the neighboring atoms, also form a Si-containing saturated or unsaturated heterocyclic ring system.

Alkyl radicals in the formula II are straight-chain or branched radicals with 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 an alkyl radical or the phenyl radical.

Haloalkyl radicals are alkyl radicals with 1 to 6 carbon atoms, which are replaced by fluorine, Chlorine and / or bromine may be substituted. An alkenyl radical which is optionally substituted by halogen has 3 up to 18 carbon atoms and an alkynyl radical 3 to 8 carbon atoms.

Form alkenyl radicals with 3 to 6 carbon atoms the alkenyl part of alkenyloxy residues. Among cycloaliphatic Residues are mono- and polycyclic cycloalkyl and cycloalkenyl radicals with 3 to 12 carbon atoms to understand.

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2U968Q

The production of the new ß-haloethyl silanes present Invention is made by adding a ß-haloethyltrichlorosilane of formula III

X - Qi ₀ - CH ₉ - Si - Cl (III)

2 2 3 ^v

with three equivalents of an acid of the formula IV

R ₄ -C- OH (IV)

Il

or of a carboxylic acid anhydride of the formula V

R ₄ -COCR ₄ (V)

H U

0 0

to a compound of the formula VI

X - CH ₉ - CH ₂ - Si - (0 - C - R ₄ ) ₃ (VI)

Il

converts and, if desired, gradually one, two or three of the residues

- 0 - C - R ₄

Il

against residues of alcohols of the formulas VII, VIII, IX R '-, ΟΙΙ (VII)

R ' ₂ 0H (VIII)

Il ' ₃ 0H (IX) exchanged.

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" ²⁴ " 2U9680

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-R, can be used in Formula VI.

Is none of the residues R'-j> R'o and R '~ identical to

- C - R ₄ ,

Il

can produce the new 0-haloethyl silanes of the formulas I and II are carried out according to a variant of the process by using a ß-haloethyl-trichloro-silane of the formula III with each one, two or three equivalents of one of the alcohols of the formulas VII, VIII or IX, where, when using ß-Bromoethyl-trichlorosilane as a starting material also low molecular weight Alkanols with fewer than 6 carbon atoms can be used for the reaction.

In formula III, X denotes chlorine or bromine, R, in formulas IV and V has the formula I, and R'-. » R'o and R'o in the formulas VII, VIII and IX those under formula II given meaning.

Since in the implementation according to the invention, the exchange of the 3 chlorine atoms of the starting material of the formula III takes place in stages, intermediate products, namely dichloro and monochlorosilanes of the formulas

Cl

^ Cl _? /

X-CH ₂ -CH ₂ -Si. and X-CH ₂ -CH-Si-OR

OR ₁ OR ₂

Ca) (b)

during the synthesis or as impurities from the crude End product of the formula I or II are isolate.

By the way, the compounds (b) were different from the general ones Formulas I and II also encompass and show biological, plant growth-regulating properties.

209816/1770

2H9680

The process is preferably carried out in the presence of. η inert breathing and / or diluents carried out. Aprotic solvents, such as. for example aliphatic and aromatic hydrocarbons; e.g. hexane, cyclohexane, Benzene, toluene, xylene, halogenated hydrocarbons, such as chlorinated ethylene, carbon tetrachloride, Chloroform, chlorobenzene, also ether and "ethereal Compounds such as diethyl ether, tetrahydrofuran, etc.

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

Furthermore, in some cases it may be necessary to add an acid-binding agent to the reaction mixture. In particular, tertiary amines such as

TrialkylcJtiiine, e.g. triethylamine, pyridine and pyridine bases, Dialky! Aniline, etc. in question.

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

The following examples serve to illustrate the process according to the invention. In the mind The following tables are more based on the examples described way produced new ß-haloethyl-silanes of formulas I and II combined.

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

209816/1770

2U9680

example 1

a) AO, 8 g of 2-chloroethyl-trichlorosilane are dissolved in 71.5 g of acetic anhydride dissolved and left to stand closed for 21 hours at room temperature. The reaction product is evaporated in vacuo. 44.6 g of 2-chloroethyl-tris- (acetyloxy) -silane are obtained, Kp: 85 - 88 ° / 0.1 Torr, n ^ ° - 1.6687 (compound 1)

Ber .: Found:

C. 35.8 36.0 H 4.8 4.7 Cl 13.20 13.4 Si 10.4 10.5

b) 26.9 g of 2-chloro'ciChyl-tris- (acetyloxy) -silane were dissolved in 40 ml dissolved in absolute benzene. At 50 - 55 ° 10.8 g of benzyl alcohol become added in 20 ml of absolute benzene within 60 minutes. The mixture is stirred for 4 1/2 hours at 50-55 °. The Reak The ion mixture is evaporated in a vacuum and obtained 14.3 g of 2-chloroethyl "(benzylo :: -: y ~ diacetyloxy) ~ silane, Kp: 125 - 127 ° / E, OO1 Torr, n ^ ° - 1.4840 (compound 2)

Ber .: Found:

C. 49.3 49.4 H 5.4 5.4 Cl 11.2 11.7 Si 8.9 8.9

209816/1770

2U9680

Example 2

26.9 g of 2-chloroethyl-fcris- (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 4 \ hours at 50 - 55 °. The reaction mixture is evaporated in vacuo and 20.2 g of 2-chloroethyl-Cdibenzyloxy-acetyloxy) -silane are obtained. Kp: 164 - 166 ° / 0.005 Torr, n ^ ⁵ = 1.5218 (compound 3).

Ber .: Found:

3 C. 59.3 59 ₃ 4 H 5.8 5.6 Cl 9.7 10.2 Si 7.7 8.0 Example

10.5 g of 2-chloroethyl-trichlorosilane are absolute in 150 ml DiUtIiVl: -t: hco- fealöst. At -5 ° to -10 °, 22.7 g are obtained 4-chlorobenzene alcohol was added within 5 minutes and then within 30 minutes 12.6 g of absolute pyridine, dissolved in 50 ml of absolute ether. Man stirs stirs for another hour, at 0 ° and then for 18 hours under reflux.

The reaction mixture is filtered, the filtrate twice washed with VJasser, dried and evaporated in vacuo. 23.5 g of 2-chloroethy1-tris- (4'-chlorobenzoxy) -silane are obtained, Kp: 200 ° - 210 ° / 0.01 Torr, n! ^ = 1.5636 (compound 4)

209816/1770

2U9680

Ber .: Ge f.

C. 53 5 53 , 4 H 4, 3 4th , 3 Cl 27 5 27 ,8th- Si ' 5, 4th 5 , 6

Example 4

16.9 g of 3-chloro-buten- (2) -ol are in 150 ml of absolute Dissolved diethyl ether. One cools down to »10 ° to -5 °, gives 12.6 g of absolute pyridine are added and a solution of 10.5 g of 2-chloroethyl-trichlorosilane is then added dropwise over the course of one hour in 50 ml of absolute diethyl ether at the same temperature. The mixture is then stirred for one hour at 0 °, ' 2 hours at room temperature and 18 hours under reflux, then it is filtered, the filtrate quickly with ice-cold water washed, dried and evaporated in vacuo. 21.5 g of 2-chloroethyl-tris- [3'-chloro-butenyl- (2 ') - are obtained

D 20

oxy] -silane, bp: 145 ° - · 15Ο ° / Ο, Ο5 Torr, n? _n = 1.4912.

(Compound 5).

Ber .: Found:

C. 41.2 41.6 H • 5.4 5.4 Cl 34.8 34.9 Si 6.9 6.6-

209816/1 770

2H9680

Example 5 (preparation of an intermediate product)

59.4 g of 2-chloroethyl-trichlorosilane are in 750 ml of absolute
Dissolved diethyl ether. At -5 ° to -10 ° a mixture of 34.9
g hexane (1) oil and 23.7 g absolute pyridine, dissolved in 250 ml
absolute ether, added within an 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 are obtained,
Bp: 69 ° -72 ° / E.1 Torr.

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. A mixture of 69.7 g is obtained at -5 ° to -10 °
Hexane-Cl) oil and 47.5 g of absolute pyridine, dissolved in 250 ml of absolute ether, were 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 are obtained,

Kp: 97 ° - 102 ° / 0.001 Torr, n ^D = 1.4423 (compound 6)

209816/1770

Compounds of the formula

-, 30 -

0 - R ₁

X - CHo «■ CHo" - Si - 0 - R

O -

Table I.

No. Κι - Rq ~ Ro X Physical data ^F P_L Kp / Torr; n ^. , 7th Aethy1 Cl Kp: 80 - 81 ° / 14 8th Aethy1 Br Bp: 83 - 4 ° / 14th 9 Hexyl Br Bp: 145-50 ° / 0.01 10 Octyl Cl Kp: 165 - 70 ° / 0.00l 11 Octyl Br Kp: 165-70 ° / 0.005 12th Dodecyl Cl _n 2 ° = 1.4545 13th Dodecyl Br nj ~ ° - 1.4582 14th Octadecyl Cl Mp: 33-36 ° 15th Octadecyl Br M.p .: 35-36 ° 16 2-chloroethyl Cl Kp: 123-26 ° / 0.001 17th 6-chlorohexyl Cl Bp: 210-15 ° / 0.03 18th 2-methoxyethyl Cl Kp: 103-105 ° / 0.05 19th 2-Ae thoxy'ci thy 1 Cl Bp: 122-125 ° / 0.005 20th 2-butyloxyethyl Cl n £ = 1.4495 21 2-allyloxyethyl Cl Kp: 140-145 ° / 0.001 22nd 2-ethylthioethyl Cl Bp: 195-200 ° / 0.005 23 2-octylthioSthyl Cl n £ ^U = 1.4895 24 3 - Ph e ny 1 pr ο ρ} '1 Cl ngo = 1.5340 25th 2 - Phenoxyä * thy 1 Cl ng ⁰ = 1.5460 26th 2-propenyl Cl Kp: 95-100 ° / 0.2 27 2-butenyl Cl Kp: 110-15 ° / 0.2

209816/1770

No. R ₁ «R ₂ - R ₃ 209 X Phy alkaline data - 20 ° / 0.0l 28 2-butenyl bi- Kp: 115 - 1.4707 29 3,7 - dimethyl-2-octenyl Cl 20th
ⁿ D / 0.35 30th 2-propynyl Cl Kp: 94 ° - 20 ° / 0.005 31 2-PropJ.nyl Br Kp: 115 - 5 ° / 0.005 32 3-IIexinyl Cl Kp: 170 - 50 ° / 0, 005 33 3 - CI11 or - 2 - ■ bu ϋ ο ny 1 Cl Kp: 145 5832 34 3 "} ^J henyl-2-propenyl Cl ngO = 1, 5882 35 3 - Γη c ny 1 - 2 - pi: op e ny 1 Br _n 20 = 1, 4696 36 3-cyanoethyl Cl ⁿ D = 1, 4492 37 Ethoxycarbonyl-methyl Cl _n 20
ⁿ D = I ₅ - 58 ° / E, 3 38 1-ethoxycarbonyl (1-methyl)
methyl Cl Kp: 154 4480 39 Butoxycarbonyl-methyl Cl _n 20 = I ₅ - 170 ° / 0.001 40 Cyclohexyl Cl Kd: 165 - 190 ° / O ₅₀₀₁ 41 Cy c 1 oh exy 1 me thy 1 Cl Kp: 180 4833 42 Cycl ohe:; y methyl Br 20th = 1, - 200 ° / 0.001 43 Benzyl Cl Kp: 190 - 1.5612 44 Benzyl Br ⁿ D ° - 20 ° / 0.0l 45 4 ~ Ch 1 or b e η zy 1 Cl Kp: 200 = 1.5757 46 4-chlorobenzyl Br 4 ° - 1.5224 47 L \ --Mo-thoxybenzyl Cl ¹¹ D = 1.6637 48 2,4-dichlorobenzyl Cl = 1.5433 49 4-methylbeii2yl Cl 20th
ⁿ D - 1.5623 50 Phenyl Cl «1.5769 51 4 - Ch lor ph α ny 1 Cl ⁿ D ^? - 1.5262 52 3-chlorophenyl Cl ⁿ D = 1.5257 53 3,4-dichlorophenyl Cl _n 20 = 1.5268 54 3,5-dichlorophenyl Cl ⁿ D = 1.5418 55 4 ~ Broraphc.nyl Cl _n 20
ⁿ D
_n 20 - = 1.5620 56 A-methoxyphenyl Cl = 1.5641 57 4 - Hoxyphenyl Br = 1.5590
= 1.5307 58
59
LJ 3-M'Lho;: ypicnyl
4-Knty] o;: ypliC! Tiyl Cl
Cl 3 16/171 Ό

2U9680

Mr. R ₁ «R ₂ = R ₃ X Physical data 60 4-tert-butyl phenyl Cl FP: 75-77 ° 61 3 "methyl! Phenyl Cl nj? ⁷ = 1.5385
tip = 1.5490 62 3-methylpheny1 Br ng ⁷ = 1.4935 63 3 j 4 - D ime t hy 1 ph eny 1 Cl M.p .: 98-101 ° 64 3-formy! Phenyl Cl M.p .: 106-111 ° 65 4 ■ - Cyanopheny 1. Cl M.p .: 112-114 ° 66 4-Acthoxycarbonylpheny1 ■ Cl M.p .: 65-70 ° 67 3-ethoxycarbonylpheny1 Cl Kp: 195-200 ° / 0.001 " 68 O,- Cl Bp: 152-154 ° / 0.001 69 Cl 23
n ^ = 1.5771 70 Cl n ^ ⁵ =, 1.4727 71 Cl I I \ s / Xc / -CH ₂ " -CH ₂ - _.CH ₂ -

209816/1770

Table II

Ur R ₁ = R ₀ = R _Q - "CO-R / . χ Physical data J- /. JH R ^ is: Br Bp: 120-122 ° / O ₅ 06 72 methyl Cl Kp: 85-88 ° / 0.1 73 methyl Cl Bp: 102-104 ° / 0.05 74 Aethy1 Br Kp: 115-125 ° / O, OO2 75 Aethy1 Cl n ^ ⁰ = 1.4286 It Pentyl Cl M.p .: 42-44 ° 11 Undecyl Br Mp: 44-47 ° 78 Undecyl Cl Mp: 54-57 ° 79 Heptadecyl Cl tip = 1.4484 80 2-propenyl Cl Cl = 24-27 ° 81 1-propenyl Br nJ5 = 1.4621 82 2-propenyl Cl nj? ⁰ = 1.4480 83 9-decenyl Cl np ^{0 to} 1.4705 84 8,11-heptadecadienyl Cl n ^ ⁰ = 1.4681
ng ⁰ =. 1.4513 85 2-chloroethyl Cl Mp: 49-50 ° 86 1-bromopentyl Cl Mp: 48-50 ° 87 10 ~ bromodecyl Br Mp: 25 ° 88 30-bromodecyl Cl Mp: 55-58 ° 89 ice-2-chloroethenyl Br M.p .: 74-78 ° 90 cis-2-chloroethenyl Cl Mp: 20-30 ° 91 Pheiiy! Methyl Br M.p .: 35-39 ° 92 Phony! Methyl Cl M.p .: 99-103 ° 93 2-phenylethyl Cl M.p .: 57-60 ° 94 4-chlorophenylmethyl Cl M.p .: 98-102 ° 95 3-methylphenyl methyl Cl 96 3- (4 '»methoxypbenyl) ethyl Cl. njT ^; = 1.4590
ng ⁰ = 1.4841 97 4-aothoxycarbony! Butyl Cl 98 3 ~ 0xobutyl Br 99 3-0: cobutyl

209816/1770

No. R ₁ = R ₀ = R ₀ = -CO-R, 2UbÖ Ί ö X Physical data 1 / - J Η
R / is: Cl M.p .: 73-75 ° 100 5 ~ phenyl-5-oxo-pentyl Cl n ² , ⁰ = 1.4365 101 2-ethoxyethyl Cl M.p .: 58-60 ° 102 3-phenoxypropyl Cl Mp: 140 ° 103 2,4-dichlorophenoxymethyl Br Mp: 137-138 ° 104 2 j 4-dichlorophenoxymethyl Cl 105 2- (4'-chlorophenyl) -l-ethhenyl Cl Mp: 128-130 ° 106 2 «Pheny1-1-etheny1 Bl- Mp: 129-131 ° 107 2-phenyl-1-ethenyl 108 2- (3'j4'-dichlorophenyl) -1- CI M.p .:> 235 ° ethenyl Cl Mp: 178 ° 109 2- (4'-methoxyphenyl-1-'ethhenyl Cl n20 = 1.4494
ng ⁰ = 1.4592 110 Cyclohexy! Methyl Br ng ⁰ = 1.4578 111 Cyclohexy! Methyl Cl n ^ ° = 1.4515 112 Cyclohexyl Cl , nj ~ ° = 1.4740
ng ⁰ = 1.4807
nj ° = 1.4630 113 Cyclopropyl Cl 114 3-cyclohexenyl Br η§ ° = 1.5e-3Z 115 3-cyclohexeny1 Cl Mp: 233 ° 116 2-cyclopentenyl Br Mp: 177-178 ° 117 2-cyclopentenyl Cl M.p .: 165-170 ° 113 Phenyl Br 119 4-chlorophenyl Br Mp: -123-126 ° 120 4-methoxyphenyl Cl 121 4-methylphenyl Br Mp: 123-125 ° 122 α Br 123 I ι Br 124 N) / " Cl 125 / 17 7 0 1 \ s / ~

2U9680

Table III

No. ^R l R ₂ R- = CO-R, X Physical data R, is: 126 Benzyl = R ₃ methyl Cl Bp: 126-27 ° / O _{5 OOl} 127 Benzyl -R ₃ methyl Br Bp: 140-143 ° / O, oil 128 Benzyl Benzyl methyl Cl Bp: 164-166 ° / O, OO5 129 Aethy1 Ethyl methyl Cl Bp: 62-65 ° / O, oil 130 Pentyl Pentyl methyl Br Bp: 104-110 ° / 0.001 131 Octyl methyl Cl Kp: 115-120 ° / 02 132 Octyl Octyl. methyl Cl Bp: 150-152 ° / 0.005 133 2-butynyl 2-butynyl methyl Cl 134 2-butenyl 2-butenyl methyl Cl Bp: 94-98 ° / 0.001 135 4-chlorine benzyl = R ₃ Ethyl Cl n ^ ⁰ = 1.4940 136 4-chlorine benzyl = R ₃ Ethyl Br ■ nJ5 ° = 1.5042 137 3.7 dim ethyl-7- oci "c · iiy 1 -R ₃ Ethyl Cl nJ5 ° = 1.4525 138 4-methoxy benzyl -R ₃ Ethyl Cl ng ⁰ = i, 4890
■

20981 6/1 770

2U9680

Table IV

No. R. j. R ₂ ^R 3 X Anion Physical CH ₃ (ϊ-
^ IJCH ₂ CH ₂ -
^t - ' ^il 3H j data 139 CH ₃ θ
^JV N-CH ₂ CH ₂ - Hexyl Hexyl Cl ci ^e M.p .: 25-35 ° 140 CH _{3 H} Benzyl Benzyl Cl ci ^e n ^ ° = 1.5212

20981 6/1770

Table V

Compounds in which R ₁ and R 2 form together with the neighboring atoms of a Si-containing heterocycle).

No.

link

Physical data

141

142

143

144

145

146

- o.i

i - CH ₂ -CH ₂ -Cl

lh

■ \

\ 0-Si-CH-CH ₀ -Cl

OC ₀ H ₁ -Z _>

C0-0 _y

CO-O

Si-CH ₀ -CH ₀ -Cl

OC ₁ -H ₁₁ • CO-O ^ I 5

^ Si-CH ₀ -CH ₀ -Cl

/ ²

CO-O

30-0 I.

Si-CH ₉ -CH ₀ -Cl / ^II

: o-o

co-

Si

CH ₂ -CII ₂ -Cl

Bp: 115-120 ° / 0.005

= 1.5233

209816/1 770

Claims (11)

2H9680 claims 1) means for regulating plant growth, characterized in that that there is at least one ß-haloethyl silane as the active ingredient of formula I. 0 - R ₁ 1 ^X X - CH ₉ - CH ₉ - Si - 0 - R (I) contains, in the Y chlorine or a radical -OR ₀ , X chlorine or bromine, R ,, R ₉ and Ro independently of one another are alkyl radicals, through halogen, Alkoxy, alkenyloxy, phenoxy, cycloalkyl, alkylthio, Alkoxycarbonyl, by heterocyclic radicals and / or alkyl radicals substituted by di- and tri-alkylammonio, Alkenyl, haloalkenyl, alkynyl and cycloalkyl radicals, optionally by cyano, nitro, alkyl, Haloalkyl, alkoxy, alkylthio, alkanoyl and / or ^ Alkoxycarbonyl mono- or polysubstituted phenyl radicals, benzyl radicals which are optionally monosubstituted or polysubstituted by alkyl, alkoxy and / or halogen, one or more of the symbols R 1, R ₉ and Ro also denote the group -CO - means in which R ^ is an alkyl, alkenyl or alkynyl radical, a haloalkyl or haloalkenyl radical, one by cycloalkyl or phenyl-substituted alkyl or alkenyl radical, where phenyl can be substituted by alkyl, alkoxy and / or halogen, also for an alkoxyalkvl-, an alkoxycarbonylalkyl-,. a benzoylalkyl or one optionally substituted by halogen, lower alkyl or 209816/1770 Alkoxy-substituted phenyl radical and finally a 5- or 6-membered heterocyclic radical, furthermore R ₁ and R _9, also in the meaning of -CÖR ,, together with the adjacent atoms can form a Si-containing saturated or unsaturated heterocyclic ring system. 2) means according to claim 1, characterized in that it as active ingredient a ß-halo-ethylsilane of the formula X-CH ₉ - CH ₉ - Si- (OR ₁ ) O (Ia) contains where X is chlorine or bromine and R ₁ denotes an optionally halogenated alkyl or alkenyl radical, an alkynyl radical or a benzyl radical which can optionally be substituted one or more times by lower alkyl or alkoxy and / or halogen. 3) means according to claim 1, characterized in that it as active ingredient a ß-haloethylsilane of the formula X-CH ₂ - CH ₂ - Si; OR ₂ (Ib) ^0R 3 contains where X is chlorine or bromine, and R, R ₉ / Ro independently of one another alkyl radicals _/ alkyl radicals substituted by halogen, alkoxy, alkenyloxy, phenoxy, cycloalkyl, alkylthio, alkoxycarbonyl and / or trialkylammonio, alkenyl-haloalkenyl, alkynyl and cycloalkyl radicals, optionally by cyano, nitro ,. Alkyl, haloalkyl, alkoxy, alkylthio, alkanoyl and / or alkoxycarbonyl.substituted or polysubstituted phenyl radicals, optionally monosubstituted or polysubstituted by alkyl, alkoxy and / or halogen . B e η ζ y .1 rest: e means η, 209816/1770 2U9680 one or more of the symbols R-, R "and R ₀ also represent the group -COR ₄ can mean in which R, for an alkyl, alkenyl or alkynyl radical, a haloalkyl or haloalkenyl radical, an alkyl or alkenyl radical substituted by phenyl, where phenyl is substituted by alkyl, Alkoxy and / or halogen can be substituted, furthermore for an alkoxyalkyl, alkoxycarbonylalkyl, a benzoylalkyl or a alkyl radical substituted by cycloalkyl. 4) Method of regulating plant growth, thereby marked that plants and plant parts or the wax ™ turns substrate of plants with ß-haloethyl silanes of the formula I of claim 1 treated. 5) Use of / 3-haloethylsilanes of the formula I of claim 1 and the formula Ia of claim 2 to improve the abscission of fruit and leaves, to accelerate ripening and to promote the flow of resin in trees. 6) New .ß-Bromoethyl-silanes of the formula / ^OR 1 Br - CH ₀ - CH ₉ - Si - OR ₀ 2 Z ι Z wherein Y, R .. and R "are as defined under formula I of claim 1 are. 7) New ß-chloroethyl-silanes of the formula OR ' Cl - CH ₀ - CH ₀ - Si - OR '(II) 2 /. ι I where Y is chlorine or the radical -0R ' _o , and P.'. R ' _o and R \ have the same meanings as R ₁ , R ₀ , R "under ^J 2098 16/1770 ^l " ³ - 2U9680 Formula I of claim 1, with the proviso, however, that unsubstituted alkyl radicals which stand for the symbols R ¹ , R '"and R' ~ have 6 to 18 carbon atoms. 8) A method for the preparation of .beta.-bromoethyl-silanes of the For ^mel Br - CH ₂ - CH ₂ - Si - wherein Y, R, and R ~ as defined under formula I of claim 1 are, characterized in that one ß-bromoethyl-trichlorosilane with at least 2 equivalents, preferably with 3 equivalents, of an acid of the formula IV R ₄ -CO-OH "(IV) or a carboxylic anhydride of the formula V R, - CO - 0 - CO - R, (V) to a compound of the formula Br - CH ₂ - CH ₂ - Si - (O-CO-R ^ Y ¹ converts, wherein Y ^{1 is} chlorine or the radical -OCOR, and. If desired, one, two or all three radicals-0-CO-R present are exchanged for radicals of alcohols of the formulas R, OH, R ₂ OH and / or RoOH, in which R 1, R 2 and R 4 are defined as in claim 1 are, excluding the meaning -CO-R ,. 9) Process for the production of ß-bromoethylsilanes of the Forms] 209816/1770 - 42 - - 2U9680 OR ₁ JL Br - CH ₂ - CH ₂ - Si ' wherein Y, R, and R _{9 are} as defined under formula I of claim 1, but none of the radicals has the meaning of -CO-R, characterized in that ß-bromoethyl-trichlorosilane with a total of at least two, preferably with a total of 3 Equivalents of one or more alcohols of the formulas R, OH, R ₂ OH and / or R ₃ OH are reacted where R, R ₂ and R- are as defined above and in claim 1, that is, excluding the meaning -COR. 10) Process for the production of new ß-chloroethyl-silanes of formula II Cl - CH ₉ - CH ₉ - Si OR '(II) ZZi Z wherein Y is chlorine or the radical -OR * - and R '-,>R' ₉ and R 'are as defined in claim 7, characterized in that ß-chloroethyl-trichlorosilane with at least 2 equivalents, preferred wise with 3 equivalents of an acid of the formula IV R ₄ -CO- OH CIV) or a carboxylic anhydride of the formula V R ₄ -CO-O-CO-R ₄ (V) to a compound of the formula Cl - CH ₂ - CH ₂ - Si - (O-CO-R ₄ ) ₂ Y ¹ 209816/1770 converts, in which Y ^{1 is} chlorine or the radical -0-CO-R ₄ , and ge If necessary, one, two or all three radicals -0-CO-R ^ present are gradually exchanged for radicals of alcohols of the formulas R ^ OH, R ' ₂ ^0H and / or R ¹ ^ OH, in which R ¹ -, R' _o and R 'are as defined in claim 7, excluding the meaning -COR ,. 11) Process for the production of new ß-chloroethylsilanes // of the formula II Cl - CH ₀ - CH ₀ - Si OR '(II) 2 2, 2 wherein Y is chlorine or the radical -OR'o, and R '^ R' ₂ and R '^ are as defined in claim 7, but none of the radicals has the data ^ c- "-COR, characterized in that one ß-Chloräthyltrichlor-silane with a total of at least two, preferably with a total of three equivalents of one or more alcohols of the formulas R ¹ , OH, R ' _o OH and / or R'-OH, where R ¹ ,, R' _o and R ¹ ^ as above, that is, excluding the meaning -COR, as defined in claim 7. FO 3.3 ^r 3 'jK / kö 209816/1770 ] 3. Septe-ib.r 1971