DD152467A5 - MEANS FOR REGULATING PLANT GROWTH - Google Patents

Abstract

1. An agent for regulating plant growth, characterized by the content of a triazolyl ether of the formula (I) see diagramm : EP0025516,P9,F3 where R**1 , R**2 and R**3 denote alkyl, alkenyl or alkynyl, each of which is unsubstituted or substituted by from 1 to 3 halogen atoms, and R**2 and R**3 may additionally denote hydrogen, X denotes halogen or phenyl, n denotes the integers 0 to 3, and Z denotes CH2 , or a salt thereof which is tolerated by plants.

Description

'Regulating plant growth regulation &% 0 ** sy? / "·

Field of application of the invention . · The new funds can be used in agriculture as growth regulators.

Characteristic of the Known Technical Solutions It is known that 2-chloroethyltrimethylammonium chloride, CCC, (J, Biol. Chem. 235 , 475 (I960) plant has growth-regulating properties in cereals and other crop plants (US Pat 156 544) It is likewise known that triazolyl alcohols (DE-OS 27 37 489, 24 07 143) influence plant growth.

When using the known plant growth regulating agents, the effect is often insufficient, especially at low application rates and concentrations.

OBJECT OF THE INVENTION The object of the invention is the development of plant growth regulators with improved efficacy in crops. '

Explanation of the essence of the invention . The invention is based on the object, new chemical

Compounds with the plant growth regulating Wirk-. to provide a sense of well-being.

^V Y It has been found that plant growth regulating agents, the triazolyl ethers of the formula I

_ 2 _ ^: OZ OO5O / O34O14

(X) n

in the

12 3

R, R and R are an alkyl radical _{s is} an alkenyl radical or a

12 3 alkynyl radical, where R, R and R may each be substituted by 1 to 2 3 3 halogen atoms and R or R ^ additionally represents hydrogen, if Z is CHp, in which X is halogen or phenyl, η is the numbers 0 to 3 and Z are CHp or oxygen or contain the phytophysiologically acceptable salts of these triazolyl ethers (eg the hydrochlorides, bromides, sulfates, nitrates, oxalates, acetates, formates, phosphates), have strong phytochemical properties and have the properties described in DE-OS

27 37 489 and DE-OS 24 07 143 described substances are superior in their effect.

12 3

R, R and R are, for example: methyl, ethyl,

Propyl, η-butyl, t-butyl, isobutyl, 3-methylbutyl, 2-methylbutyl, n-pentyl, allyl, crotyl, methallyl, 3-methyl-buten-2-yl-1, 1-buten-4-yl , Propargyl, 2-butyn-1-yl, 2,3-di-25. chlorallyl, vinyl.

X is, for example, chlorine, bromine, iodine, fluorine, phenyl.

Surprisingly, the compositions of the invention have a much stronger plant growth-regulating effect than the known 2-chloroethyl-trimethylammonium chloride, which is a recognized good effective substance of the same mode of action.

The agents interfere with the metabolism of the plants and are therefore growth regulators.

- 3 - 0.2. 0050/034011]

Pure mode of action of plant growth regulators "'applies according to the experience that an active compound can exert one or several different actions on plants. The effects of the compounds depend essential

% From the time of application, based on the stage of development of the seed or plant, and on the amounts of active substance applied to the plants or their surroundings, and on the method of administration. In any case, growth regulators should positively influence the crop plants in the desired manner.

Plant growth regulating substances can be used for example for the inhibition of vegetative plant growth. Growth inhibition of this kind is of economic interest, inter alia, for grasses, since attenuation of grass growth can be achieved, for example. reduce the frequency of grass clippings in ornamental gardens, parks and sports facilities or on roadsides. Also of importance is the inhibition of the growth of herbaceous and woody plants on roadsides and in the vicinity of power lines or, more generally, in areas where heavy vegetation is undesirable.

It is also important to use growth regulators to inhibit grain length growth, as it reduces the risk of crop rotation ("storage") before harvesting or eliminates it altogether. In addition, growth regulators in crops can cause a stalk reinforcement, which also counteracts storage.

An inhibition of vegetative growth allows for many crops a denser planting of the culture, so that an additional yield based on the soil surface can be achieved. , '

u. j

- 4 - ^: OZ 0050/034014

Another mechanism that increases yield with growth ^inhibitors is based on the fact that nutrients benefit flower and fruit formation to a greater degree, while

the vegetative growth is restricted. 5

Growth regulators can often be used to promote vegetative via. This is of great benefit when harvesting the vegetative plant parts. Promoting vegetative growth, however, can also simultaneously promote generative growth, so that e.g. more or-bigger fruits come to the training.

In some cases, increases in yield can also be achieved through an intervention in the plant metabolism, without any noticeable changes in vegetative growth. Growth regulators may also cause a change in the composition of the plants, so as to bring about a better quality of the harvested products. For example, it is possible to increase the sugar content in sugar beet, sugarcane, pineapple and citrus fruits, or to increase the protein content in soya or cereals.

Under the influence of growth regulators, parthenocaper fruits may form. Furthermore, the sex of the flowers can be influenced.

With growth regulators, the production or the outflow of phytochemicals can be positively influenced. An example is the stimulation of latex flow in gum trees.

During the growth of the plant, the use of growth regulators can also cause lateral branching

_ 5 - O.Z. OO50 / 03401M

'"propagated a · chemical breaking of the apical dominance advertising ^n. This is of, for example, interest in the propagation of cuttings from P.flanzen. However, it is also possible to inhibit the growth of side shoots, for example to at Täbakpflanzen. 5 after decapitation training to prevent side shoots and thus promote leaf growth.

Under the influence of growth regulators, the leaves of plants can be controlled so that a leaf

10 * tern of the plants is achieved at a desired time. Such defoliation is of interest for providing mechanical harvesting, e.g. in wine or cotton, or to reduce transpiration at a time when the plant is to be transplanted.

By using growth regulators, premature fruit can be prevented. However, it is also possible, the fruit case, -. in fruit, in the sense of a chemical thinning to a certain extent too.

promote. Growth regulators may also serve to reduce the force required to detach the fruits from crops at the time of harvesting so as to enable mechanical harvesting or facilitate manual harvesting. ,

Growth regulators can also be used to accelerate or retard the ripeness of the crop before or after harvesting. This is of particular advantage because it can bring about an optimal adaptation to the needs of the market. Furthermore, growth regulators in some cases improve fruit colouration. In addition, with the help of growth regulators, a temporal concentration of the maturity can be achieved. This creates the prerequisites for e.g. with tobacco, tomatoes or coffee,

- 6 -: O. Z. 0050/03 ^ 014

a complete mechanical or manual harvest can be made in just one operation.

The use of growth regulators can also influence the seed or bud rest of the plants, ie the endogenous annual rhythm, so that the plants, such as e.g. Pineapples or ornamental plants in nurseries to germinate, sprout or flower at a time when they normally show no readiness to do so.

Growth regulators can also be used to delay the budding of buds or the germination of seeds, e.g. to avoid damage from late frosts in areas prone to frost.

Growth regulators can also produce halophilia (salt tolerance) in crop plants. This creates the conditions for cultivating plants on saline soils

can be. ,

With growth regulators, a frost and dry resistance can be induced.

The triazolyl ethers of the formula I in which R ¹ , R, R, Z, X and η have the abovementioned meanings are prepared by reacting the partially known triazolyl alcohols of the formula II in which R, R, Z, X and η den have the abovementioned meanings, with alkylating agents RY of the formula III in which R has the abovementioned meanings _: , and Y is a nucleofugic group, eg Cl, Br, J, OSO ₃ R, CH 1 -CgH ₁ J-SO ₃ , CH ₃ O-CgH ₁₁ -SO ₃ .

O. Z. OO5O / O34O14

, HO

(X) n

R ¹ Y '

III

R ¹ O

/ ^N -N

R- / 7 ~ ^ (X) n Z - //

The triazolyl alcohols of the formula II are known in some cases (DE-OS 23 24 010, 27 37 489). The previously unknown compounds of formula II can be prepared by known methods in a simple manner by, for example, the known TriazoIyIketone of formula IV (DE-OS 22 01 Ο63, 26 38 470) in a known manner with reducing agents such as NaBHh, .Hp / Catalyst reacts or by bringing the TrazoIyIketone of formula IV with metal alkyls of the formula V to the reaction.

(X) n

R ² -M

(X) n

IV

Metal alkyls of the formula V are, for example: ethylmagnesium bromide, methylmagnesium bromide, allylmagnesium bromide, proparylmagnesium bromide, vinylmagnesium bromide, ethynylmagnesium chloride, vinylmagnesium chloride, methylmagnesium iodide, butyl lithium, sodium methyl. The compounds of the formula II are obtained by adding to a solution of the metal alkyl compound V in a suitable solvent, eg Diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane is added dropwise to the Triazolylketon of Formel.IV and then possibly heated to reflux ·

O. Z. OO5O / O34O14

The following information explains the preparation of fertilizer of formula (II): to 137.5 ml of a 1.6 molar solution of vinylmagnesium chloride in tetrahydrofuran is added dropwise at 20 to 35 ° C a solution of 29, 4 g of bis (chlorophenoxy) o- (i, 2,4-triazol-1-yl) -pinacolone are stirred for 5 hours at 40 to 45 ° C., and then, with ice cooling, 150 ml of water are added dropwise ml 20 #iger aqueous ammonium chloride solution, the organic phase separated. the aqueous phase is extracted twice with ^ 150 ml of ether. the combined organic phases are washed with 150 ml $ 20 aqueous NH _2, Cl solution and twice with 50 ml of water, dried over Na ₂ SO ₄ and concentrated.

The residue crystallizes on trituration with n-pentane, recrystallization of cyclohexane / ethyl acetate gives 12 g of 4- (4-chlorophenoxy) -2,2-dimethyl-4- (1,2-triazol-1-yl) 3-vinyl-butan-3-ol, mp 153 ° C.

Examples of compounds of formula II are shown in Table 1 below.

£ 3 SWt

OO5O / O34O14

table

(X) n

(X) n

Mp.

t-butyl

η η tt it

'' X; ., Il IS Ilm tt "'it. ·. Η" it it tiIf 5? tt ft ti it

CH ₃ -CH = CH /

-CsCH

CH ₂ CH = CH ₂

-CH = CHj CH,

-CH

CHp-CK =

CH,

-CH = CH ₂

-C = CH

-C ₂ H ₅

CH ₂ CH = CH ₂

CH ₂ C-CH

^nC 4 ^H 9 CH ₃

-CH = CH ₂

CH ₃

-CH = CH ₅

'CH,

O O O O

O O O O O O O O

CH ₂ CH.

CH. CH, CH,

CH, CH. CH,

4-Cl

4-Cl

4-Cl

4-Cl

4-Cl

WCl

4-Cl

2,4-Cl

2,4-Cl

4-Br

4-Br

4-Cl

4-Cl

4-Cl

4-Cl

4-Cl

4-Cl

4-Cl

2,4-Cl

2,4-Cl

.4-

160 153

176-179

148-151

ffe C. ^ "* a # ⁵ C ₅ * #

- 10 - 0.2. OO5O / O34Oill

R ³ It R ² H ₂ Z (X) η Mp. ti CH ₂ '4-Br It H CH ₂ 4-Cl 11 H CH ₂ 2,4-Cl ft H CH ₂ 4-Br H CH ₂ O ₂ H ₅ CH ₃ 0 4-C1 99-100 C ₂ H 0 4-Cl

Further starting compounds for the preparation of the triazolyl ethers of the formula I are, for example, the following alkylating agents of the formula III: methyl bromide, methyl iodide. Dimethylsulfate, FSO, CH ,, ethyl br.omide, ethyl iodide ,. Allyl bromide, Allyloodid bromopropane ^ "^ propyl-lbhl propyl, isobutyl, n-butyl bromide _s / isobutyl, 2" methyl "butylbroraid _3-i-Iiethyl butylbr'Offii (i _i Pentylbro mid, CH ₃ -C ₆ H ₂₁ -SO ₃ CH ₃ , CH-C ₆ H ₄ -SO ₃ C ₂ H ₅ .

The compounds of formula I are obtained by adding to a solution of the compounds of formula II in a suitable solvent, e.g. Tetrahydrofuran, dioxane, methyl tert-butyl ether, dimethylformamide, dimethylacetamide in the presence of a suitable base such as .Diisopropylethylamin, Lithiumdiisopropylainid, - Buty! Lithium, sodium hydride, the alkylating agent of formula III. dripped and possibly heated at atmospheric pressure or elevated pressure.

Also suitable for the alkylation of the alcohols of the formula II is the phase transfer method (E.V. DehmloW; Angew. Chem.), 521 to 533 (1.977)).

The following instructions illustrate the preparation of the compounds of Formula I.

 35

- 11 - O.Z. OO5O / O34O14

Regulation 1 . , , ^Ί

To a suspension of 1.25 g of NaH in 80 ml of tetrahydrofuran is added dropwise a solution of 12.4 g of 2,3,3-trimethyl-1- (4-chlorophenoxy) -l- (l, 2,4-triazolo- l-yl) -butan-2-ol in 80 ml of tetrahydrofuran. The mixture is stirred for 3 hours at room temperature and added dropwise 6.3 g of iodomethane. After stirring for 24 hours, 200 ml of water are added dropwise. It is extracted twice with 150 ml of ether. The organic phase is washed three times with 50 ml of water, with Na ₂ SO ₁ . dried and concentrated. This gives 12.8 g of lp-chloro-phenoxy-2-methoxy-2,3,3-trimethyl-l- (l, 2,4-triazol-1-yl) -butane (active ingredient No. 24).

Elemental analysis: ( ^c i6 ^H 22 ° 2 ^N 3 ^C1 ^ 323.8

Calculates C 59.4; H 6.9 N 13.0 Cl 11.0 Found C 59.4 H 6.9 N 12.7 Cl 10.6

NMR (CDCl ₃ , cT values): 1.00 (s, 9H), I, 16 (s, 3H), 3.32 (s, 3H), 6.10 (s, IH), 6.82 (d, J = 11 Hz, 2H), 7,12. (d, J = 11Hz, 2H), 7.90 (s, IH), 8.38 (s, IH).

Rule 2 * ·

To a suspension of 1.6 g of sodium hydride in 80 ml of tetrahydrofuran at 50 to 60 ° C 14.7 g of 1-p-chlorophenyl-4,4-dimethyl-2- (l, 2j4-triazol-l-yl) - pentane-3-ol in 70 ml of tetrahydrofuran was added dropwise. The mixture is heated for 2 hours to reflux, added dropwise 6.5 g EthyLbromid and further heated for 5 hours to reflux. After again 6.5 g of ethyl bromide. added and heated to reflux for 5 hours, 150 ml of water are added dropwise. It is extracted three times with 100 ml of ether. The combined ether phases are washed three times. 50 ml of water, over Na ₂ SO ^

- 12 - O.Z. 0050/034014

^r dried and concentrated. Chromatography of oily ^Ί

Crude Produkt.s over silica gel with CHpCl ₂ gives 6.5 g lp-chlorophenyl-4 ^ -dimethyl - ^ - ethoxy - ^ - (1 _J 2,4 - triazole ^ L - -yl) pentane. Matches IO6 to 108 ° (active ingredient no. 2).

  ''. '

Vorsc hrift 3

To a suspension of 1.6 g of sodium hydride in 100 ml of tetrahydrate is added dropwise a solution of 15 _s 4 g of 1-chlorophenyl-3,4,4-trimethyl-2- (l, 2,4-triazole-1 »Yl) -pentan-3 ™ ol in 100 ml tetrahydrofuran« Warm to reflux for 2 hours. After cooling, 8.5 g ~ iodomethane are added dropwise. The mixture is heated for 5 hours to reflux, 200 ml of water are added, extracted three times with 100 ml of ether, the combined organic phases are washed three times with 50 ml of water, dried and concentrated. From petroleum ether crystallize 9.5 g of lp-chlorophenyl-3,4,4-trimethyl-3-methoxy-2- (l, 2,4-triazol-1-yl) -pentane, mp. 125 to .127 ° ( Active ingredient No. 15).

·

In an analogous manner, the compounds of Table 2 are accessible.

O. Z. 0050/034014

R ¹ Q

(X) n

table 2 R ² t-Bu Z (X) n Mp. ° C Active substance no. R ¹ H t-Bu CH ₂ 4-Cl 1 CH H t-Bu CH ₂ 4-Cl 106-108 2 \ s ill-- H t-Bu CH ₂ 4-Cl 3 nC H ₇ H t-Bu CH ₂ 4-Cl 4 H t-Bu CH ₂ 4-Cl 105-107 5 CH ₂ CH = CH ₂ H t-Bu CH ₂ 4-Cl 98-100 6 CH C = CH H- t-Bu t-Bu CH ₂ 4-Cl 7 CH ₂ CCl = CHCl H H t-Bu CH ₂ CH ₂ 2,4-Cl ₂ 2,4-Cl ₂ 90-95 8 9 OH ₃ CH ₂ CH = CH ₂ H t-Bu CH ₂ 2,4-Cl ₂ 10 CH ₂ C = CH H t-Bu CH ₂ 11 CH ₃ H t-Bu CH ₂ 12 CH ₂ CH = CH ₂ H t-Bu CH ₂ 13 ^nC o ^H o H t-Bu CH 4-Br 14 • • CH ₃ t-Bu 4-Cl 125-127 15 CH ₃ CH ₃ t-Bu CH ₂ 4-Cl 16 C ₂ H ₅ CH ₃ t-Bu CH ₂ 4-Cl 17 CH ₂ CH = CH ₂ CH ₃ t-Bu CH ₂ 4-Cl 18 CH C = -CH -CH = CH ₂ t-Bu CH ₂ 4-Cl 19 ^CH 3- -CH = CH ₂ t-Bu CH ₂ 4-Cl 20 C ₂ H ₅ -CH = CH ₂ t-Bu CH ₂ 4-Cl 21 CH ₂ CH = CH ₂ -CH = CH ₂ t-Bu CH ₂ 4-Cl 22 CH ₂ C ' ^S CH -C = XH t-Bu CH ₂ 4-Cl 23 CH ₃ CH ₃ t-Bu 0 4-Cl oil 24 CH ₃ CH ₃ 0 4-Cl 25 C ₂ H ₅

O. Z. OO5O / O34O14

2025

'"Drug no.

R ^£

(X) n

C. C

26 CH ₂ CH = CH ₂ CH ₃ t-Bu 0 4-Cl oil 27 CH ₂ CsCH CH ₃ t-Bu 0 4-Cl 28 CH ₃ -CH = CH ₂ t-Bu 0 4-Cl 96-98 29 ' C ₂ H ₅ -CH = CH ₂ t-Bu 0 4-Cl 30 CH ₂ CH = CH ₂ -CH = CH ₂ t-Bu 0 4-Cl oil 31 CH ₂ C = CH -CH = CH ₂ t-Bu 0 4-Cl 32 CH ₃ -C = CH t-Bu 0 4-Cl 33 -CH · CH ₃ t-Bu 0 4-Br 34 CH- CH, t-Bu 0 35 ^2H 5 mJ H t-Bu CH ₂ 2,4-Cl ₂ 102-104 36 ^CH 3 H t-Bu CH ₂ ^C 6 ^H 5 37 • CH ₂ CH = CH ₂ H t-Bu CH ₂ ^C 6 ^H 5 38 CH ₃ CH ₃ t-Bu CH ₂ ^C 6 ^H 5 39 CH ₂ CH = CH ₂ CH ₃ ' t-Bu CH ₂ ^C 6 ^H 5 40. CH ₃ CH ₃ t-Bu 0 ^C 6 ^H 5 41 CH ₂ CH = CH ₂ CH ₃ t-Bu 0 ^C 6 ^H 5 42 CH ₃ . CH ₃ CH ₃ 0 4-Cl oil 43 , CH ₃ C ₂ H ₅ C ₂ H ₅ 0 4-Cl 44 CH ₂ CH = CH ₂ CH ₃ CH ₃ 0 4-Cl

t-Bu = tertiary-butyl

30 .., 35

- 15 - ^: OZ 0050/034014

• "The new products may be available in common formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules.The forms of application are strictly in accordance with the purposes for which they are intended to ensure a fine and even distribution of the active substance The formulations are prepared in known manner, for example by stretching the active ingredient with solvents and / or excipients, if appropriate using emulsifiers and

] Q. Dispersants, although in the case of the use of water as a diluent, other organic solvents may be used as auxiliary solvents. As auxiliaries are essentially in question: solvents such as aromatics (eg xylene, benzene), chlorinated aromatics

"J (e.g., chlorobenzenes), paraffins (e.g., petroleum fractions), alcohols (e.g., methanol, butanol), amines (e.g., ethanolamine, dimethylformamide), and water; Carriers such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed

2Q silicic acid, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates); and dispersants such as lignin, spent liquors and methylcellulose.

The compositions generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90.

The application rates are in the manner of the desired effect 2Q between 0.01 and 3, but preferably between 0.01 and 1 kg of active ingredient per hectare. , _:

The compositions or the ready-to-use preparations prepared therefrom, such as solutions, emulsions, suspensions, powders, dusts, pastes or granules are known in the art

- 16 - ° · ^ζ · ΟΟ5Ο / Ο34Ο14

For example, by spraying, atomizing, dusting, scattering, pickling or pouring.

Examples of such preparations are:

Execution examples.

I. 90 parts by weight of the active compound 1 is mixed with 10 parts by weight of N-methyl-oc-pyrrolidone and obtains a solution which is suitable for use in the form of very small drops.

II. 20 parts by weight of the active ingredient 2 are dissolved in a mixture of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water to obtain an aqueous dispersion containing 0.02 wt. $ Of the active ingredient.

III. 20 parts by weight of the active ingredient 3 are dissolved in a mixture consisting of 40 parts by weight of cyclohexane, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight contains 0.02 wt. % Of the active ingredient.

IV. · 20 parts by weight of the active ingredient 4. Are dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction u of boiling point 210 to 280 ° C and 10 parts by weight

- 17 - O.Z. OO5O / O34O14

** of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring and finely dispersing the solution in'100.000 parts by weight of water gives an aqueous dispersion which comprises 0.02.% Containing the active ingredient.

V. 20 parts by weight of the active ingredient 1 are the with

3 parts by weight of the sodium salt of Dilsobutylnaphthalin-cis-sulfonic acid, 17 parts by weight of the

] Sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered:! Silica gel mixed well and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water to obtain a spray mixture containing 0.1 wt.% Of the active ingredient.

VI. 3 weight of the active ingredient 2 are intimately mixed with 97 parts by weight of finely divided kaolin. This gives a dust containing 3 wt.% Of the active ingredient.

VII. 30 parts by weight of the active ingredient 3 are mixed with a mixture of 92 parts by weight of powder

, Silica gel and 8 parts by weight of paraffin oil, the. sprayed onto the surface of this silica gel. intimately mixed. This gives a preparation of the active substance with good adhesion * '' * ability. , ·; , :. . - ·: ·:. , ·. ; ··.

VIII. 40 parts by weight of the active ingredient 4 with 10 parts of sodium salt of a phenol sulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and *. 48 parts of water intimately mixed. You get a •. stable aqueous dispersion. By diluting with 100,000 parts by weight% gives an aqueous dispersion _and 0.04 wt. V / he active ingredient contained contains.

"18 - O. Z. 0050/034014

^r IX. 20 parts of the active compound 1 are intimately mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of phenolsulfonic acid-forcnaldehyd condensate and 68 parts of a paraffinic mineral oil. This gives a stable oily dispersion.

The agents according to the invention may also be present together with other active substances in these application forms, e.g. Herbicides, insecticides, growth regulators and fungicides, or mixed with fertilizers and applied.

To determine the growth-regulating property of the test substances, test plants were grown on sufficiently cultivated substrate in plastic vessels of about 12.5 cm in diameter.

The substances to be tested were sprayed onto the plants in aqueous preparation (post-emergence method). The observed growth-regulating effect was determined by stature height measurement at the end of the experiment. The measured values thus obtained were related to the growth height of the untreated plants. The reference substance used was CCC.

The color intensity of the leaves increased concurrently with the reduction in elongation. The increased chlorophyll content also leads to increased photosynthesis and therefore increased yields. '

The individual data can be found in the following tables.

O. Z. OO5O / O34O14

^r comparison substance:

CH ₃ Duration of test: - Summer rape "Petronova" Duration of test: - cl * % 100 % te te OO OO 3 4 Active ingredient no. Mg active substance / Gef. 1.5 6 post-emergence; Active ingredient no. Mg active substance / Gef. 1.5 6 91 91 100 , 9, 6 0 2 CCC CH _O N _O CH * -CH _O -C1 Jl. t ^ CH ₃ untreated 1.5 6 untreated te Ul 20 days 74 67 83, 78, , 7, 8 5 3 Summer rape "Cosa" CCC (known) 1.5 6 CCC (known) 1.5 6 Growth heights cm 79 62 76, 66, • inco I post-emergence; 5 24 1.5 6 20.7 73, 61, 6 26 19.0 19.0 73, 58, 28 15.5 14.0 16.5 13.0 20 days Growth heights cm 20.4 17.0 16.0 15.5 13.5 15.0 12.5 15.0 12.0.

CS ₃ . &. "Sas? ^ ^ ®

20 - * O.Z, 0050/034014

"" Tomato "Little Red Riding Hood"

post-emergence; duration of test mg active substance / Gef. rag active ingredient / Gef. : 45 days 100 100 5 Active ingredient no. - - 100 92.9 97.0 96.3 untreated 1.5 6 1.5 6 - Growth heights cm % 69.6 66.5 97.7 72.3 CCC (known) 1.5 6 1.5 6 .- 23 83.8 73.7. 10 2 1.5 6 23 21.4 Tomatoes "Sonata" Kachauflaufverfahren; duration of test 16.0 15.3 Vheight heights cm % 15 Active ingredient no. 34.6 untreated : 50 days 33.6 33.3 CCC (known) 33.8 25.0 20 5 29.0 25.5 6 25

- 21 - O. Z. OO5O / O34O1-1 »

^r salad "Lüneburg · Ice"

post-emergence; Duration of the experiment: 26 days 18.5 100 Active ingredient no. 17.5 17.0 94.6 91.9 untreated mg active substance / Gef. Growth heights cm % 14.5 14.0 78.4 75.7 CCC (known) 12.5 12.3 67.6 66.5 2 13.3 10.8 71.9 58.4 5 6 - 0.7.5 1.5 0.75 1.5 0.75 1.5 0.75 1.5

Claims (1)

.223 397 - 22 - 'O.Z. OO5O / O34O14 ^r invention claim Plant growth regulating agent characterized by a content of a solid or liquid carrier and a triazolyl ether of the formula (X) η '1OO in which R , R and R are alkyl, alkenyl or alkynyl radicals which are substituted by 1 to 3 halogen atoms 2 3 where R or R can also be hydrogen, when Z is CH, in the
X is halogen or phenyl
η the numbers 0 to 3 and
Z is CH ₂ or an oxygen atom or a plant physiologically acceptable salt of these compounds.