DD213346A5 - 28-METHYL BRASSINOSTEROID DERIVATIVES CONTAINING GROWTH REGULATORY EFFECT ON PLANTS - Google Patents

Abstract

The invention relates to novel 28-methyl-brassinosteroid derivatives containing growth regulators for plants of the general formula I in which Z is the group -CO-CH deep 2- or -OC-CH deep 2-, R deep 2, R deep 3 and R deep 22 are the same or different and each represents hydrogen or an acyl radical, but at least one of these radicals is an acyl radical, or, if R is lower-22 hydrogen or an acyl radical, R deep 2 and R 3 deep together the groups C = O or C high X deep Y in which X is hydrogen, C is deep 1-C deep 4-alkyl or C is deep 1-C deep 3 -alkoxy and Y is hydrogen, C deep 1-C deep 4-alkyl, C deep 1-C deep 3-alkoxy or aryl, in mixture with carriers and / or auxiliaries.

Description

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Field of application of the invention;

The invention relates to novel agents with growth-regulating action for plants for use in agriculture.

Characteristic of the known technical solutions

Compounds with growth-regulatory effects are already known and sometimes even introduced in practice.

From the pollen of oilseed rape a plant growth promoting steroid - the brassinolide - was isolated and the structure elucidated (S & M, D. Grove et al., Hature Vol. 281, 216 (1979)). The growth regulatory activity of this compound is but not satisfactory ·

Aim of the invention

The aim of the invention is the provision of new agents with strong growth-regulating effect *

Explanation of the essence of the invention

The object of the invention is to develop novel brassinosteroid derivatives with plant growth-regulating properties which are superior to the known constitutional analog brassinolide.

This object is achieved by an agent which is characterized by a content of at least

-a-

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a compound of the general formula

in the

Z are the groups -CO-GH ₀ -

or -0-G-GH

0 -

represents,

R ₂ , R and R _{22 are the} same, or different and each represents hydrogen or an aeyl radical, but where at least one of these radicals is an acyl radical or, if R _{00 is} hydrogen or an acyl radical, Rp and R "together denote groups

or

in which X is hydrogen, G ₁ -substituted, Cj-C ^

or G ₁ -G ₃ -alkoxy and Y represents WasserG ₁ -G-AIkOXy or aryl.

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The compounds of the present invention occur as geometric isomers with -ORp and -OR-cis 2 cn , 3 ^ or cis 2β, 3β oriented and having OR ₂₂ and OH ₂₃ cia 22R, 23R configuration or ice 22S, 23S configuration Isomers and their mixtures are also part of the subject of the invention.

The compounds according to the invention are outstandingly suitable for regulating plant growth in various crop plants and, in their spectrum of activity and in their compatibility, surprisingly exceed the initially mentioned product of the same mode of action »

The compounds according to the invention are able to promote the vegetative growth of crop plants, but also to inhibit them in certain concentration ranges. · In addition, it is possible to achieve certain additional income by influencing the generative phase ·

In general, the substances act on the membrane system in crops and change its permeability to various substances »

Under certain conditions, they may have an anti-stress effect.

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

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Inhibition of vegetative growth in woody and herbaceous plants, for example on roadsides, railroad tracks and others, to prevent too much growth. Growth inhibition in cereals to prevent storage or kinking, in cotton to increase the yield.

Influence on the branching of vegetative and generative organs in ornamental and crop plants for the propagation of flower buds or in the case of tobacco and lomates "'for the hejamtang of lateral shoots"

Improvement of fruit quality, for example a sugar content increase in sugar cane, sugar beets or fruit and a more even ripeness of the harvest, which leads to higher yields »

Increasing the resistance against stress, for example against climatic influences, such as cold and drought, but also against the phytotoxic effects of chemicals »

Influencing the latex flow in Gusunip plants «

Training of parthenocarp fruits, male sterility and sex influence are also possible applications.

Control germination of seeds or budding buds.

Defoliation or influence of the fruit case for the relief of sneezes »

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

In general, the amounts of treatment per unit of application are from 0.001 to 1 kg of active ingredient per hectare; if appropriate, higher application rates can also be used.

The application time depends on the application target and the climatic conditions »

The compounds according to the invention are distinguished by the effect described in particular those in which, in the abovementioned general formula IZ, the groups -CO-CH ₀ - or -O-C-CH ₀ -

H * - ti <-

0 0

represents,

R ₂ , R_. and Rp _{2 are the} same or different and each represents hydrogen or an acyl radical, but at least one of these radicals is an acyl radical, or, if R _{22 is} hydrogen or an acyl radical, R ₂ and R, together form the groups

C = O or ^ C

represent in the

X is hydrogen, C -C -alkyl or C -C -alkoxy and Y is hydrogen CCalkyl CCAlkOXy or aryl

mean, C ₁ -C 4 -alkyl, C ₁ -C 4 -alkoxy or aryl,

As aryl radicals may be mentioned the pormyl radical, the C ^ C ^ -Alkyi-CO-Reate ,. the ₂₇ C 1 -C 6 -alkyl-CO-Reate and the aryl-GO radicals such as, for example, acetoxy, methoxyacetoxy, ethoxyacetoxy, propionyloxy-butyryloxy, valeryloxy, pentanoyloxy, hexanoyloxy, heptanoyl

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oxy, dimethylaoetoxy, diethylacetoxy, benzyloxy and phenylacetoxy

As C ..- G. Alkyl radicals are, for example, methyl, ethyl, propyl, Isopropyl, butyl, sec-butyl, tert-butyl and chloromethyl; C, -C ~ alkoxy radicals are, for example, methoxy, ethoxy and propoxy; As aryl radicals are finally beneimexi Haphthyl, phenyl, 2-chlorophenyl, 3-Ghlorphenyl, 4-chlorophenyl, 2,6-dichlorophenyl, 2,4-dichlorophenyl ₉ 3> 4-BiGhlorphenyl, 2,4,6-Triohlorphenyl, 4- * bromophenyl, 2,4-dibromophenyl, ^2,6-D ibromphenyl, 2,4,6-tribromophenyl, 2-S'luorphenyl, 3-Sluorphenyl, 4-5'luorphenyl, 2,4-difluoro-phenyl ^ ,. 2-methylphenyl, 3-methylphenyl, 4-methylphenyl ,. 3,4-Bimethyl: 1-phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,4-bioxymethylenephenyl, 2-phenoxyphenyl, 3-phenoxyphenyl, 2-nitrophenyl and 3-hitrophanyl

The compounds of the invention may be used either alone, in admixture with each other or with other active ingredients. Optionally defoliants, pesticides or pesticides may be added according to the desired purpose *

If broadening of the spectrum of action is intended, other biocides may also be added. For example, the herbicidally active compound partners are those active substances which have been used in Weed Abstracts, Vol. 31, 1981 under the title List of Common Names and Abbreviations employed for currently used In addition, non-phytotoxic agents may be used

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with herbicides and / or growth regulators can result in a synergistic increase in activity, such as wetting agents, emulsifiers, solvents and oily additives.

The active compounds according to the invention or mixtures thereof are expediently used in the form of preparations, such as powders, scattering agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and optionally of wetting agents, tackifiers, emulsifiers. and / or dispersing aids, used ·

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethylsulfoxide, dimethylformamide, and furthermore maleic-oil fractions.

solid supports are mineral earths, for example, tonsil, silica gel, talc, kaolin, ataclay, limestone, silicic acid and vegetable products, for example flours,

Surfactants are mentioned. for example, calcium lignosulfonate, polyoxyethylene-alkylphenol ethers, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and their salts *

The proportion of the active substance (s) in the various preparations can vary within wide limits. For example, the compositions contain about 10 to 80 percent by weight of active compound, about 90 to 20 percent by weight of liquid or solid carriers and optionally up to 20 percent by weight of surface-active substances,

* a 4 / / 4 - ι

- ο "

The application of funds can be done in the usual way, sum. Beiapiel with water as a carrier in Spritzbrühmengen of about 100 to 1000 liters / ha _o Sine application of funds in the so-called low-volume or ultra-low Yolume method is just as possible as their application in Porm of so-called microgranules.

For the preparation of the preparations, for example, the. following components are used:

A. SpritZOver

a) 80% by weight of active ingredient 15% by weight of kaolin

5 percent by weight of surfactants based on the sodium salt of N-methyl-N-oleyl-taurine and

the calcium salt of lignosulfonic acid. 15

b) 50% by weight of active ingredient

kO weight percent clay minerals 5 weight percent cell pitch 5 weight percent surfactants on the

Base of a mixture of the calcium salt of lignin

sulfonic acid with Alkylphenolpolyglykoläthem.

c) 20% by weight of active ingredient

70 weight percent clay minerals

5% by weight cell pitch

5 percent by weight surfactants based on a mixture of the calcium salt of Li-gninsulfonsäure with Alkylphenolpolyglycolätheam.

d) 5% by weight of active ingredient

Tonsil 80% by weight Tonsil 10% by weight Zellpech 5% by weight surfactants on the

Base of a fatty acid condensation product. 35

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B. emulsion concentrate.

20% by weight of active ingredient 40% by weight of xylene 35% by weight of dimethyl sulfoxide 5% by weight mixture of nonylphenylpolyoxyethylene or calcium dodecylbenzenesulfonate

G « paste

45% by weight of active ingredient 5% by weight of sodium aluminum silicate 15% by weight of cetyl polyglycol ether with S mole of ethylene oxide

2 weight percent spindle oil 10 weight percent polyethylene glycol 23 pounds of water.

The novel compounds according to the invention can be prepared, for example, by reacting compounds of the general formula

HO

HO

HO

II

a) with Garbonsäureanhydriden optionally in the presence of a catalyst,

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b) optionally with boron trifluoride etherate dissolved in an organic solvent,

c) with ^ riäthylorthoessigsäureester optionally in the presence of a catalyst dissolved in an organic solvent or

d) with acetophenone in perchloric acid

and the desired process products isolated in a conventional manner.

They are starting products 28-methyl-brassinolides, are prepared from stigmasterol, for example as described in Steroids, 39 (1982).

Auaführungsbeiapiel

The invention is explained in more detail below with reference to some examples. The following examples illustrate the preparation of the compounds according to the invention,

EXAMPLE 1

embedded image 2a, 3a, 22S, 23S-tetrahydroxy-2 ^l! i-ethyl-7-oxa-3-homo-5acholestan-6-one were dissolved in 10 ml of pyridine, cooled to 0 C, treated with 0.5 ml of acetic anhydride and stirred at -5 to 0 ° C for 5.5 hours , It was then precipitated in ice water, the product was filtered off with suction, washed with water, dried and chromatographed on silica gel. After recrystallization from acetone-hexane gives 810 mg of 2a-acetoxy-3a, 22S, 233-trihydroxy-2 ^z iäthyl-7-oxa-B - homo-5ot-cholestan-6-one, m.p .: 125 C

I 54 / / 4 - 1 -Ί1-

EXAMPLE 2

Ig 2α, 3 <ζ, 22S, 23S-tetrahydroxy-2 * i-ethyl-7-oxa-B-hofiozo-5acholes-tan-6-o, were dissolved in 10 ml of pyridine, cooled to 0 ° C and admixed with 1 ml of acetic anhydride added and stirred at 0 C for 7 hours. It was then precipitated in ice-water, filtered off with suction, washed with water and dried. Chromatography on silica gel (gradient elution with chloroform-acetone) gives 320 mg of 2a, 3a-diacetoxy-22S, 23S-dihydroxy-2 ^/ i-ethyl-7-oxa-B-homo-5a-cholestan-6-one, m.p. .: 120 ° C and 535 mg of 2-a _t 22S-diacetoxy-3a, 23S-dihydroxy-2 * i-ethyl-7-oxa-B-homo-5a-cholestan-6-one, m.p .: ΐΛ6 ° 0 ,

EXAMPLE 3

210 mg of 2a, 3a, 22R, 23R-tetrahydroxy-2 ^z i-a-Chyl-7-oxa-8-homo-5a-cholestan-6-one were reacted as described in Example. 1 Obtained after recrystallization from acetone-hexane 170 mg of 2a-acetoxy-3a, 22R, 23R-trihydroxy-24-ethyl-7-oxa-B-homo-5 cc-cholestane-6-one, m.p .:

EXAMPLE

500 mg of 2α, 3α, 223,23S-tetrahydroxy-2-yl-ethyl-6-oxa-B ~ homo-5a-cholestan-7-one were reacted analogously to Example 1. Recrystallization from methylene chloride-isopropyl ether to obtain 385 mg of 2a-acetone-3a, 22S, 23S-trihydroxy-2 ^/ i-ethyl-6-oxa-B-homo-5a-cholestan-7-one, mp.: 198-200 ^O C.

EXAMPLE 5

Ig 2a, 3a, 22S, ^{23S-tetrahydroxy-2, for} i-ethyl-6-oxa-3-homo-5acholestan-7-one were prepared as described in Example 2, reacted and separated. This gives 290 mg of 2a, 3 <2-diacetoxy-22S, 2 3 S-dihydroxy-2 ^ i-ethyl-1-6-oxa-B-homo-5a-choles tan-7-one, mp.: 135 ° C and 56Ο mg of 2a, 22S-diacetoxy-3a, 23S-dihydroxy-2α-i-ethyl-6-oxa-B-homo-5a-cholestan-7-one, m.p .: 152C.

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EXAMPLE 6

500 mg 2ß, 3ß, 22S, 23S-tetrahydroxy-2 ^z i-äxhyl-7-oxa-B-homo-5cc-cholestan-6-one (m.p .: 182 I83-C) were acetylated -As in Example 1 describe , There are thus obtained ethylsiloxy-3β-acetoxy-2β, 22S, 23S-trihydroxy-24-ethyl-7-oxa-B-homo-5a-cholestan-6-one, m.p .: 166-162 ° C.

EXAMPLE 7

3OO mg 2a, 3 <2,22S, ^{23S-tetrahydroxy-2, for} i-ethyl-7-oxa-B-homo-5cc-cholesxan-6-one l of pyridine were dissolved in 3 ^m, cooled to 0 ° C and treated with 0.6 ml of V.aleriansäureanhydrid added. It was stirred for 10 hours at 0 C, precipitated in ice water, washed with water and dried. The crude product was chromatographed on silica gel and the obtained 2a-valeryloxy 3, 22S, 23S-trihydroxy ^^ - ethyl ^ -oxa-B-homo-Sa-cholestan-o on recrystallized from acetone-hexane, mp.: 100-105 C.

Analog were produced:

2a-heptanoyloxy-3a, 22.R, 23R-trihydroxy-24-ethyl-7-oxa-B-homo 5a-cholestan-6-one, m.p. 85-87C

2a-Dime thy lac and oxy-3 <z, 22S, 2.3S-trihydroxy-2 ^ -äthyi-7-oxa-3-homo-5 <z-cholestan-6-one, m.p .: 121-122.5 C

2a-butyryloxy-3α, 22S, 23S-trihydroxy-2 ^z t-ethyl-6-oxa-3-homo-5a-cholestan-7-one, m.p .: 92-9 ^{1 0} ^ C

2a-diethylacetoxy-3a, 22S, 23S-trihydroxy-2H-ethyl-7-oxa-3-homo-5a-cholestan-6-one, m.p. 113-115C

EXAMPLE 8

300 mg of 2a, 3α, 22S, 23S-tetrahydroxy-24-ethyl-7-oxa-B-homo-5a-cholestan-6-one were dissolved in 3 ml of fyridine, cooled to OC and treated with 1 ml of valeric anhydride. The mixture was stirred at 0 C for 20 hours, precipitated in ice-water, washed with water and dried. After chromatography on silica gel (gradient elution with chloroform-acetone) to obtain 120 mg 2c, 3a-DivaJary.lcxy-22S, 2 3S-dihydroxy-2 ^z iäthyl-7-oxa-B-homo-5a-cholestan ~ 6 ~ one, Mp: 109-110 ° C and 160 m _; 2a, 22S-DivaJaryloxy-3a, 23S-dihydroxy-2 ^ -ethyl-7-oxa-B-homo-5a-cholestan-6-one _f m.p .: 123,5-13O ° C

Analog were produced:

2a, 3a-dihexanoyloxy-22S, 23S-dihydroxy-2 ^z i-ethyl-7-oxa-B-homo-5a-cholestan-6-one, mp .: 88-9O ° C

2a, 223-dihexanoyloxy-3,3,2,3-dihydroxy-2-i-ethyl-7-oxa-B-homo-5a-cholestan-6-one, m.p .: 117-120 ° C

EXAMPLE 9

500 mg of 2a, 3a, 22R, 23R-Tetrahyd2-oxy-2 ^z i-ethyl-7-oxa-B-homo-5a-cholestan-6-one were dissolved in 5..ml pyridine, cooled to 0 ° C, with 0.3 ml, Athoxyessigsäureanhydrid and stirred at -5 to 0 C for 6 hours. After working up and isolation, as described in Example 1, 310 mg of 2a-ethoxyacetoxy-3a, 22R, 23H-trihydroxy-2 ^/ i-ethyl-7-oxa-B-homo-5a-cholestan-6-one, m.p. : l32-l83 ° C.

EXAMPLE 10

Ig 2a, 3a, 22S, 23S-Tetrahydrüxy-2 ⁱ i-ethyl-7-oxa-B-homo-5acholestan-6-one were added in 100 ml of tetrahydrofuran and 100 ml of acetone with 0.5 ml boron trifluoride etherate and at -5 to OC for 30 minutes. After adding 1 ml of pyridine

It was concentrated in vacuo, precipitated with water, filtered off with suction and washed with water. After Urakristallisation from acetone to obtain 731 mg 2α, 3a-isopropylidenedioxy-22S, 23S-dihydroxy-2 ⁱ i-ethyl-7-oxa-B-homo-5a-cholestan-6-one, mp .: 198-201 ⁰ C. ,

Analog were produced:

2α, 3a-isopropylidenedioxy-22S, 23S-dihydroxy-2- ⁱ -ethyl-6-oxa-B-homo-5a-cholestan-7-one, m.p .: 211-213 ° C

2ß, 3ß-isopropylidenedioxy-225,23S-dihydroxy-2 ^£ i-ethyl-7-oxa-B-homo-5a-cholestan-6-one, m.p .: l89-191 ° C

EXAMPLE 11

1 g of 2a, 3a, 225, 23S-tetrahydroxy-2M: -ethyl-7-oxa-B-homo-5c: - cholestan-6-one were in 100 ml of 3enzol with 1.5 ml Triäthylorthoessigsäureester and 5 mg of p-toluenesulfonic acid added and stirred for 30 minutes at room temperature. After addition of

2 drops of pyridine was concentrated in vacuo, diluted with methylene chloride, washed with water and evaporated. The crude product was triturated with isopropyl ether to give 720 mg of amorphous 2a, 3a (1-ethoxyethylenedioxy) -22S, 23S-dihydroxy-2-hydroxy-ethyl-7-oxa-B-homo-5a-cholestan-6-one diastereomeric mixture.

Analog were produced:

2a, 3a- (1-Xthoxy-propylidendioxy) -22S, 23S-dihydroxy-2 ^z i-ethyl-7-oxa-B-homo-5a-cholestan-6-one, amorphous

2a, 3α- (1- methoxymethylenedioxy ) -22R, 2 3R-dihydroxy-2- ⁱ -ethyl-7-oxa-B-homo-5a-cholestan-6-one, m.p .: 96-99 ° C

2SS, 3ß- (1-ethoxy-ethylenedioxy) -22S, 23S-dihydroxy-2 ⁱ i-ethyl-7-oxa-B-homo-5a-cholesxan-6-one, mp .: 8 ^ -87 C

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EXAMPLE 12

200 mg of 2α, 3α, 22S, 23S-tetrahydroxy-2 ^/ i-ethyl-7-oxa-B-homo-5a-cholestan-6-one were added in 2 ml of acetophenone with 0.01 ml of 72% perchloric acid and 16 Stirred hours at room temperature. Subsequently, 0.1 ml of pyridine was added and on silica gel chromatographies. By gradient elution with toluene-ethyl ester 120 mg of amorphous 2a, 3 were - (1-methyl-l-phenyl-methylenedioxy) -22S, ^{23S-dihydroxy-2-z} i äthyly-oxa-B-homo-pc-cholestane -ö-on as a diastereomeric mixture.

Analog were produced:

2a, 3a (1-methyl-1-phenyl-methylenedioxy) -22S, 2,3S-dihydraxy

EXAMPLE 13

200 mg of 2a, 3a-22S, 23S-Te-cahydroxy-24-yl-6-oxa-B-homo-5a-cholestan-7-one were dissolved in 7 ml of diethylcarbonau and 2 ml of tetrahydrofuran after addition of 15 mg of sodium methylate Heated to 130 ° C (bath temperature) for 2.5 hours. After cooling, the mixture is neutralized with acetic acid and evaporated in vacuo. The residue is dissolved in chloroform-acetone, filtered through silica gel, and the filtrate is concentrated. Recrystallization from acetone-hexane 155 mg of 2α, 3α-carbonyldioxy-22S, ^{23S-dihydroxy-2-z} i ärhyl-6-oxa-3-homo-5acholestan-7-one, mp .: 2 ^ 2.5 -2 ^ 4 ⁰ C

Analog were produced:

2a, 3 <2-carbonyldioxy-22Pv, 2 3R-dihydroxy-2- ⁱ -ethyl-6-oxa-B-homo-5cc-cholesan-7-one, m.p .: 216-217 ° C

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5EI5PIEL 1 k

200 mg of 2a, 3a-22S, 23S-tetrahydroxy-2 ^ i-äthyI-6-oxa-B-homo-5a-cholestan-7-one are dissolved in. K ml of tetrahydrofuran, 1 ml hinzugefügx benzaldehyde, to -13 ° C. and 0.2 g of a perchloric acid solution (prepared from 0.5 ml of 0% perchloric acid in 1.5 ml of tetrahydrofuran). It is stirred for 15 minutes at -15 ° C, neutralized with pyridine, diluted with chloroform and chromatographed on silica gel. With chloroform-acetone (1: 1) 153 mg of amorphous 2α, 3α-Benzylidendioxy-22S, 23S-dihydroxy-2 ^z t-ethyl-6-oxa-B-homo-5acholestan ^ -7-one eluted.

Analog were produced:

2a, 3a-benzylidenedioxy-22R, 2 3R-dihydroxy-2 ^/ i-ethyl-7-oxa-3-homo-5a-cholestan-6-one

2a, 3a-Benzylidendioxy-22S, 23S-dihydroxy-2 ^z i-ethyl-7-oxa-3-homo-5a-cholestan-6-one.

ho mo - 5 α - c ho read on 6 - ο η.

The compounds of the invention are generally crystalline dyes and odorless substances which are sparingly soluble in water, conditionally soluble in aliphatic hydrocarbons such as petroleum ether, hexane, pentane and cyclohexane, readily soluble in halogenated hydrocarbons such as chloroform, methylene chloride, carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene and xylene, ethers, xie diethyl ether, tetrahydrofuran and dioxane carboxylic acids such as acetonitrile, ketones such as acetone, alcohols such as methanol and ethanol, carboxylic acid amides such as dimethylformamide and sulfides such as dimethyl sulfoxide.

The following examples illustrate the possible uses of the compounds according to the invention, which took place in the form of the above-mentioned preparations.

254,774-t

EXAMPLE 15

Growth support for bush beans

Bush beans of the variety "Pinto" were grown in the climatic chamber at 25 C and 90% humidity under the action of light with a high level of intensity Lm range of 66Onm and a very low proportion in the range of 730 mn.

After 6 days of cultivation, 10 and 20 ng were added. solubilizing compounds in solvents applied to the developing second intemode.

3 days after the application, the extension of the internodes was measured and the percent elongation was determined in comparison with the control.

The table contains the results of this experiment.

Compounds of the invention Percentage promotion 10 ^ g 50

2a-acetoxy Yes, 22S, 23S-trihydroxy-24-ät: hyl-3-homo-7-oxa-5 ^r --c holes tan-6-one

22-acetoxy-3g, 2'2R, 2 3R-trihydroxy-24-t hy 1 - 7 - ο xa - B - ho mo - 5 cc - c holest an - 6 - ο η

2a, 22S-diacetoxy-3a, 23S-dihydoxy-24-ethyl-7-oxa-B-homo-5g: -cholestane-ο-η η

2α, 3 <2-diacetoxy-22S, 23S-dihydroxy-24-ethyl-7-oxa-B-homo-5'-cholestan-6-one

2a-VaJ = ryioxy- 3a , 22S, 2 3S -crihydroxy-4-ethyl-7-OXa-B-JiOmO ^ c: -cholestane-β-ο η COMPARATIVE

2a, 3a, 223.2 3S-Tetrahydroxy-24-ethyl-B-homo-7-oxa-5o-cholestan-6-one 4- (3-indolyl) -butyric acid

control

285 39 209 380 51 304 114 100 215 > 323 279 57 323 114 38 100

The findings show that the compounds according to the invention under the stated test conditions effect a more intense stretching than the comparison means and the control.

In contrast, the comparison means cause only a more or less strong promotion of thickness growth which in part even led to a compression of the internodes

3EI5PIEL 16

Growth inhibition in cucumbers

Cucumber seeds were germinated under greenhouse conditions in aqueous emulsions of the compounds to be tested in a concentration of 0.01% by weight.

After 6 days, the length of the radicles and shoots became

measured.

The table contains the percent inhibition of growth in the concentration range indicated.

Compounds of the invention Percent inhibition of root shoot growth

2a-Acetoxy-3 a, 22S, 23S-trihydroxy

24-ay 1-B-homo-7-oxa-5c: -c ho Ie sx

6-on. 38 28

2a-acetoxy-3 <x, 22R, 2 3R-trihydroxy-2 ² * - ^> ethyl-7-oxa-B-homo-5 <2-cholesan-6-one 50 28

2a, 22S-diacetoxy-3a, 2 3S-dihydroxy-2 ⁱ iäthyl-7-oxa-B-homo-5 <2 choiestan-6-one 63 0

2a, 3a-diacetoxy-22S, 2S3-dihydroxy-2H-ethyl-7-oxa-B-homo-5a-cholestan-6-one. 100 56

2aVa ^ ryloxy3a, 22S, 2 3S-crihydroxy-2- ⁱ -ethyl-7-oxa-3-homo-5cc-cholestan-6-one 75 56

Control 100 100

The compounds according to the invention have a markedly inhibiting effect on growth in the abovementioned experimental setting.

Growth regulators for plants

Claims (2)

invention claim 1, growth regulators for plants, characterized by a content of at least one compound of the general formula H ₂ O R ₃ O in the
Z the groups -CO-CH ₀ - Il <- or -Q-C-CH 0 represents, R ₂ , R ₃ and R _{22 are the} same or different and each represents hydrogen or an acyl radical, but at least one of these radicals is an acyl radical, or, if R _{22 is} hydrogen or an acyl radical,
R ₀ and Ro together the groups O or represent in the "" "" '' Χ is hydrogen, C 1 -C 4 -alkyl or O-C ₃ -alkoxy and Y is hydrogen, C ₁ -C -alkyl, C ₁ -C ₃ -alkoxy or aryl, mixed with inert and / or hilly open ' 2. Means according to item 1, characterized in that they are used for influencing the vegetative and generative growth in legumes, in particular soybean.