CA1125533A

CA1125533A - Plant growth regulators containing triazolyl ethers as active ingredients

Info

Publication number: CA1125533A
Application number: CA289,835A
Authority: CA
Inventors: Friedrich Linhart; Bernd Zeeh; Klaus Gutsche; York Hartleben; Johann Jung; Bruno Wuerzer
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 1976-11-06
Filing date: 1977-10-28
Publication date: 1982-06-15
Also published as: NL7711953A; PL103464B1; DE2650831A1; DK491077A; FR2369796B1; SU685128A3; CS194820B2; PL201906A1; DD131834A5; JPS5359031A; BE860493A; SE7712332L; GB1593687A; FR2369796A1

Abstract

ABSTRACT OF THE DISCLOSURE:
The invention is concerned with a composition for influencing the growth of plants, which contains a compound of the formula

Description

112S53;~

~ rhe present invention relates to plant growth regulators containing triazolylalkyl ethers as active ingredients, and the use of these compounds for influencing plant growth.
It is known (U.S. 3,156,544) that (2-chloroethyl)-trimethyl-ammonium chloride has growth-regulating properties.
It can, for instance, be used to influence plant growth, especially to inhibit vegetative growth in some cereals and other crops.
However, the action of this compound is frequently insufficient, it can only be applied to a relatively small number of crop plants, and it is rapidly inactivated when applied to the soil over a fairly long vegetation period.
We have now found that compounds of the formula , (R )n ~ /~CH-CH ~ I, where Rl denotes unsubstituted or chloro-substituted unsaturated alkyl of 3 to 5 carbon atoms, 4-chlorobenzyl or 2,4-dichlorobenzyl, R2 denotes hydrogen or alkyl of 1 to 4 carbon atoms, R3 denotes fluoro, chloro, bromo, methyl, trifluoromethyl, phenyl or alkoxy of 1 to 3 carbon atoms, and n denotes one of the integers 0. 1, 2 and 3, the radicals R3 being indentical or different `when n = 2 or 3, and their salts, are excellently suited for influencing plant growth. The present invention therefore provides compositions for influencing plant growth which contain these compounds or acid addition salts thereof in an amount ranging from 0.5 to 90% by weight based on the total weight of the composition, in admixture with a solid or liquid carrier.
The acid addition salts correspond to the general formula R2 o R1 (R )n HS
-CH-CH ~ II, 1125e~33 O ZO 32,271 where R1, R2, R3 and n have the above meanings and E~S denotes any organic or inorganic acid capable of forming salts with compounds Or the formula Io Examples of suitable acids are sulfuric acid, nitric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, acetic acid, propionic acidg butyric acid, benzoic acid and dodecylbenzene-sulfonic acidO
The salts of the formula II may be prepared by simple addition of the acids HS to the compounds of the formula I, if desired in a solventG t The compounds inhibit the growth of unwanted plants better than the prior art (2-chloroethyl)-trimethylammonium chloride, and are also effective in crops in which the prior art compound has no effect~
The following table contains examples of active ingredients of the formulae I and II:

llZ55;33 TABLE
No. R R2 (R )n HS m.p.(C)

2 -CH2-CH=CH2 H 4-Cl HNO3 97 - 98 2a -CH2-CH=CH2 H 4-Cl HCl 133 - 135

3 -CH2-CH=CH2 H 4-Br HCl 142 - 145

4 -CH -CH=CH H 4-Br HNO3 99 - 100 -CH2-CH=CH2 H 3-Br HNO3 119 - 120 - 10 6 -CH2-CH=CH2 H 2,4-C12 3 7 -CH2-CH=CH2 H 2,4-Cl HCl 110 - 112 8 -CH2-CH=CH2 H 2,4-Cl ~ nD2 = 1.5568 9 - -CH -CH=CH H 2 4-Cl H C -C H -SO H paste -CH2-CH=CH2 H 2,4-C12 1/2 H2C2O4 102 - 103 11 -CH2-CH=CH2 H H HNO3 96 - 98 12 -CH2-CH=CH2 H 4-OCH3 HNO3 120 - 121 13 -CH2-CH=CH2 H 3,4,5-(OCH3)3 HNO3 135 - 136 : 14 -CH2-CH=CH2 H 2,3,4-(oCH3~3 HNO3 134 - 135 -CH2-CH=CH2 H 2,4-(OCH3)2 HNO3 126 - 127 16 2 CH CH2 -(CH2)3-cH3 4-Cl HNO3 132 - 133 17 2 CH CH2 -(CH2)3-cH3 4-Br HNO3 143 - 144 18 -CH -CH=CH -CH 4-Br - b.p. (0.0~ mm) 2 2 3 . 152-153 19 -CH2-CH=CH2 -CH3 4-Br 3 20 -CH2-CH=CH2 -CH3 2,5-(OCH3)2 HNO3 115 - 116 22 -CH2-C--CH H 4-Cl HNO3 109 - 110 23 -CH2-C-CH H 3-Br HNO3 113 - 114 24 -CH2-C--CH H 4-Br HNO3 119 - 120 25 -CH2-C-CH H 2 4-Cl HNO3 128 26 -CH2-C-CH H 2,4-(OCH3)2 HNO3 136 - 137 27 CH C-CH H 2,3,4-(OCH3)3 HNO3 128 - 129 28 -CH2-C-CH H 3,4,5-(OCH3)3 HNO3 135 - 136 ~l2~ 3 TABLE 1 (cont'd) No Rl R2 (R )n HS m.p,(C) 30.C 2 -~CH2)3-CH3 4-Cl HNO3 121 - 123 31 -CH2-CH=CH-CH3 H 4-F HNO3 111 - 112 32 -CH2-CH=CH-CH3 H 4-Cl HNO3 107 - 109 33 -CH2-CH=CH-CH3 H 3-Br HNO3 110 - 112 34 -CH2-CH=CII-CH3 H 2,4-Cl ~INO3 115 35 -CH2-C--C-CH3 H 2 4-Cl HNO3 133 - 134 36 -CH ~ Cl H 4-Br HNO3 146 - 147 37 -CH -CH=CH H 4-CH3 HNO3 122 - 123 38 -CH ~ ( 2)3 3 HNO3 146 - 147 39 -CH2-CH=C H 2,4-Cl HNO3 133 - 134 ~CH3 46 -CH2-CH=C ~ H 2,4-Cl HNO3 141 - 143 47-CH2-CH=CH2 H 4-Cl 112S~ oOzO 32,271 The compounds of the formula I may easily be prepared by reaction of alkall metal salts of the formula ~ ~ -CH-CH ~ (R3)n III, where R2, R3 and n have the above meanings and Me denotes sodium or potassium, with a compound of the formula x-Rl IV, where R1 has the above meanings and X denotes chloro, bromo, iodo, methosulfate or toluenesulfonate, preferably chloro, bromo and iodoO
The alkali metal salts of the formula III are readily obtained from 1-aryl-2-triazolylalkanols of the formula (R3)n N~ -CH-CH~,~/ V
by reaction with strong bases such as alkali metal hydride and alkali metal amide, or with lower alkali metal alcoholates; in the latter case, the lower alcohols which form have to be removed by azeotropic distillation. It is generally not necessary to isolate the alkali metal salts of the formula III. They may be further reacted with compounds of the Pormula IV in an inert solvent, eOgO, toluene, xylene, tetrahydrofuran or dimethylformamide, immediately after having been prepared.
The preparation of alcohols of the formula V is known (German Laid-Open Application DOS 2,431,407)o Depending on the conditions under which the reactions are carried out, the compounds are obtained either in the form of the free bases I or their salts IIo The salts may be converted in conventional manner into the free bases, e.g,, by reaction with an alkali such as sodium or potassium hydroxide, sodium or potassium carbonate, ammonia, etcO The compounds as bases may be converted into the valuable - from the application point of view - acid addition salts by reaction with acids, eOgO, inorganic

- 5 -1~25~3 OOZo 32,271 acids~ such as hydrochloric acid, hydrobromic acld, hydriOdic acid, sulfuric acid~ nitric acid and phosphoric acid, or organic acids) such as acetic acid, propionic acid3 butyric acid, glycolic acid, benzoic acid and toluenesulfonic acid, or higher alkylbenzenesul-fonic acids such as dodecylbenzenesulfonic acidO
The following characteristic examples, ;n which all parts are by weight, are intended to illustrate3 and not restrict, the method of manufactureO
EXAMPLE
At 50C, a solution of 20 parts of 1-(2,4-dichlorophenyl)-2-~ ,2',4'-triazolyl-(1'~ -ethanol in 50 parts of anhydrous dimethyl-formamide is dripped into a suspension o~ 502 parts of 80% sodium hydride in 110 parts of tetrahydrofuran. After refluxing for 2 hours while stirring, 15.8 parts of 3-bromopropene is dripped inO After stirring for 1 hour at 50C, water is added and extraction carried out with ether. With ice cooling, 98% nitric acid is added dropwise to the extract. 19 parts of crystals precipitate out, which, when recrystallized from ethyl acetate, give 12 parts of 1-(2,4-dichloro-phenyl)-1-allyloxy-2- C~2~4~-triazolyl-(l~ -ethane as hydro-nitrate; m.p.: 129C.

2.7 parts of 1-(4-bromophenyl)-2- rl',2',4'-triazolyl-(1')]-ethanol and 0O5 part of sodium hydride are stirred with each other in dimethylformamide until no more gas evolves. With ice cooling, 0.7 part of allyl chloride in 20 parts of dimethylformamide is dripped inO After stirring for 1 hour at room temperature, water is added, the aqueous phase is extracted with ethyl acetate, the extract is concentrated and dissolved in ethanolJ and a solution of hydrogen chloride in isopropyl ether is added~ The solution which is obtained is concentrated, ether is added, and the precipitate is recrystallized from a mixture of isopropyl ether and isopropanol.
There is obtained 1~6 parts of 1-allyloxy-1-(4-bromophenyl)-2-~',2',4'-triazolyl-(1')~-ethane as hydrochloride; mOp~: 142-145C.

~1;Z5533 The compositions according to the invention are suitable for influencing plant growth. In particular, they may be used as growth regulators, and have a particularly good action on Cruciferae, especially rape, and specifically winter rape.
The superior action of the active ingredients of the compositions according to the invention over the prior art compounds and their enrichment of the art is impressively demonstrated by the influence on the growth of winter rape.
Various winter rape varieties giving high-quality oils tend to lose prematurely in the fall - without the influence of cold - their inhibition to flower, and to enter the generative phase. Such plants are particularly sensitive to frost. Furthermore, the vegetative development is neglected when the plant enters the generative phase, with the result that in the following spring too few leaves have developed; as a consequence for example, photosynthesis suffers. The aim is therefore to keep the rape plants in the vegetative development stage before the winter frosts set in, in spite of the good supply of nutrients and favorable growth conditions. At the same time, the premature development of too luxuriant a foliage (which is destroyed anyway be frost) should be avoided.
We have now found that the compositions according to the invention, especially those containing compound no. 4 in the table above, enable the growth of the crop plant rape to be regulated in the abovementioned manner.
In other crops, too, e.g., winter cereals, especially winter barley, it is advantageous for the plants, after treatment with the compositions of the invention, to be well tillered in the fall, but for them not to enter the winter with too luxuriant a growth. This is a prophylactic-~lZ5~i33 measure against the increased sensitivity to frost and - due to the relatively small amount of foliage - various diseases.
The compositions according to the invention are therefore preferably appliedin the fall and winter. Furthermore, growth-regulating effects have also been achieved in various other crops and also wild-- 7 a -~1;Z~33 O.ZO 32,271 growing species, and are described below.
1- L~-aryl-~-(alkenyloxy)-ethy~ -imidazoles are known (German Laid-Open Application DOS 2,063,857) whose chemical structure is similar to that of the active ingredients to be employed in accor-dance with the invention, and which have fungicidal and bactericidal properties~ Representatives of these compounds were synthesized and included in the examples for comparison purposes, even though the publication makes no mention of a growth-regulating action in higher plantsO A prior art triazolyl derivative (German Laid-Open Appli-cation DOS 2,407,143) was also examined; however, as it contains a phenoxy radical and a C group its chemical structure differs con-o siderably from that of the compounds to be employed in accordance with the invention.

NoO Prior art compounds ~ r . 3 I ~
41 Cl-CH2-CH2-N~ -CH3 Cl U.S. 3,156,544 CH3 , O-CH2 -CH=CH2 42 N~N-CH2-CH ~ Br . HN03 German Laid-Open Application (DOS) 2,o63,857 O-CH2-CH=CH2 43 N ~N-CH2-CH ~ Cl . HN03 German Laid-Open Application (DOS) 2,o63,857 O-CH2-CH=CH2 44 N~ N-CH2-lH ~ Cl . HN03 German Laid-Open Application (DOS) Cl 2,o63,857 N O CH
~ \ ., , 3 N~N-CH-C-C-CH3 German Laid-Open O CH3 Application (DOS) Cl _ 8 - 2,407,143 112553~3 O.Z~ 32,271 The following examples, carried out in the greenhouse with at least partially controlled environmental conditions, and in the open, illustrate the use Or the com~osltions according to the invention.

A) Greenhouse experiments Test method a The test plants, separated by species, were sown in small paraffined paper cups having a volume Or 200 cm3. The substrate was a minerally fertilized sandy loam containing 1.5% humus and having a pH Or 508. In the preemergence treatment (PRE), the chemical sub-stances were applied immediately after sowing to the still unswollenseeds which were only lightly covered with soil. In the postemergence treatment (POST) or leaf treatment, the test plants were first grown to a height of 3 to 10 cm, depending on the growth shape, before they were treated. The test substances were applied by means Or atomizing nozzles in water as the distribution medium. Depending on the temperature requirements of the plants, the experiments were set up in the warmer or cooler part Or the greenhouse. The experi-ments were carried out over a period Or several weeks. The duration depended on the development Or the individual species and their growth potential in the small containers. Assessment was visual, on a O to 100 scale, O denoting no change in growth, 100 denoting in-hibition equivalent to destruction Or the plants. Growth height measurements are given in cm (cf. Tables 4 and 5).
Test method b In a different method (Neubauer system) the test plants were sown in a peat substrate supplied with sufficient nutrientsO The - active ingredients were applied in aqueous solution or dispersion at various rates to the soil and to the foliage. In the soil treatment, the active ingredients were sprayed on to the surface of the soil 3o on the day the seeds were sown; in the foliage treatment, the com-pounds were applied in conventional manner by spraying at a growth height of the plants of approx. 8 cm. During the growth period of 18 days, the plants treated with the comp~sitions according to the , - 9 _ ` llZ5S3~ OOZJ 32,271 `
invention exhibited a distinctly lower growth height compared with the untreated control, which was confirmed by subsequent measurements.
From each series, 100 plants were measured The imidazole compounds used for comparison exhibited no action at all (cfo Tables 9 and 10).

B) Vegetation experiment in accordance with the Mitscherlich system To ascertain the effect of the treatment with the various agents according to the invention on monocotyledons under conditions approximating to those in the open, a vegetation experiment was carried out with spring barley in large (10 liter) vesselsO The plants were grown in a sandy loam, fertilized with 1.5 g of N as ammonium nitrate and 1 g of P205 as secondary potassium phosphate.
The active ingredients were applied as an aqueous solution or dis-persion to the surface of the soil (after sowing) by means of a pipette. N-2-chloroethyl-N,N,N-trimethylammonium chloride (no. 41) used as comparative compound was, however, applied to the foliage at a growth height of the plants of approx. 28 cm, as it is known of - this compound when applied to the soil over a fairly long vegetation period that it is rapidly inactivated (cf. Table 11).

C) Experiments in the open Small plots were laid out with the predominant aim of studying the development of winter rape varieties under the influence of a composition according to the invention. The composition was applied to the foliage a few weeks after sowing with the aid of a tractor-driven plot sprayO Water was the carrier medium for the finely divided active ingredientO The observation period extended from the time of treatment through the winter and frost period up to commencement of flowering. The development stage of the plants was recorded at various intervals (cfo Tables 12, 13 and 14)~

Results The greenhouse experiments and those in the open show that the compositions according to theinventionespecially those containing active ingredient noO 4, have a growth-regulating action on numerous plant species from the most widely varying botanical families (Table 4).

B

1~553~ o~ z ~ 32,271 Visually, a reduction in growth height was recorded, the value of which must be interpreted individually from species to species The action of the closest comparative compound with regard to function, 2-chloroethyl trimethylammonium chloride (noO 41),was equalled or exceeded. This applies particularly with respect to the large number of plant species which reacted to treatment~ith c~sitions according to the invention, whereas they only reacted slightly, or not at all, to the comparative co~und (rrables 4, ~, 9, lO, ll, 12, 13 and 14)~ -Other prior art compounds (nos. 42 - 45), employed because of their structure for comparison purposes, had an inferior action (Tables 5, 6 and 7). It should be pointed out that the compounds with an imidazolyl radical which are the closest with regard to chemical structure have not been described as plant growth regulators.
A particularly outstanding property Or the cQmpositions according to the inventior is their specific influence on the growth Or winter rapeO Vegetative growth was checked and premature entry into the generative stage prevented, thus ensuring better overwintering and yield chances for the plants. At the same time, unwanted plants occurring in rape crops were inhibited in their growth to su¢h an extent that they were unable to outgrow the crop plants deliberately inhibited in their growth; they were thus insignificant as com-petitors.
The action on cereals was also noteworthy, as, inter alia, the experiment in Tables 4 and 11 (barley) shows.

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~L125533 Table 4 - Influence on the growth of various test plants by different active ing:redients~ postemergence treatment in the greenhouse -Species Amount of active Growth height in cm inyredientCompound no. 4 Compound No.41 kg/ha Euphorbia 0+ 27 27 geniculata 1,0 24 25 2,0 25 28 4,0 24 25 Hordeum 0 16 16 vulgare 0,5 15 16 2,0 11 15 4,0 10 14 -Medicago 0 27 27 sativa 0,5 25 - 26 1,0 21 25 2,0 18 24 4,0 15 22 Secale cereale 0 70 0,25 52 0,5 49 , 1,0 48 -- 2,0 46 Triticum 0 31 31 aestivum 0,5 23 28 1,0 21 30 2,0 20 26 4,0 14 21 + = untreated control 1~55~33 . o\'~ .
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E~ O ~ ~ ~ Lr ~r ~0)~0 ~ ~ ~ ~ o Table 6 - Influence on the growth of rape; soil treatment (Neubauer system) Compound no.Application rate Plant height kg/ha cm relative untreated - 17,8 100 42 3,00 17,8 100 12,00 17,8 100 - 43 3,00 17,7 100 12,00 17,8 100 44 3,00 17,8 100 12,00 17,8 100 4 3,00 15,5 87 12,00 13,9 78 38 3,00 16,4 92 12,00 14,0 79 Table 7 - Influence on the growth of rape; leaf treatment (Neubauer system) Compound no.Application rate Plant height kg/ha cm relative 20untreated - 15,8 100 42 1,50 15,8 100

6,00 15,8 100 43 1,50 15,8 100 : 6,00 15,8 100 44 1,50 15,8 100 6,00 . 15,8 100 37 1,50 15,5 98 6,00 12,0 76 l~Z553~3 Table 8 - Influence on the growth of mustard; soil treatment (Neubauer system) Compound no.Application rate Plant height kg/ha cmrelative untrea-ted - 15,0 100 41 3,00 14,5 97 12,00 13,0 87 2 3,00 15,0 100 12,00 11,5 77 2a 3,0Q 15,0 100 12,00 10,1 67

7 3,00 14,9 99 12,00 12,0 80 12 3,00 13,2 88 12,00 13,0 87 .

Table 9 - Influence on the growth height of oats; soil treatment (Neubauer system) Compound no.Application rate Plant height kg/ha cmrelative 20untreated - 30,0 10 41 3,00 28,0 93 12,00 25,4 84 -2 3,00 20,7 69 12,00 19,8 66 2a 3,00 23,4 78 12,00 18,9 63 12 3,00 24,0 80 12,00 18,9 63 11~55313 Table 10 - Influence on the growth height of rye; soil treatment (Neubauer system) Compound no.Application rate Plant height kg/ha cm relative untreated - 32,0 100 41 3,00 32,0 100 12,00 29,9 93 2 3,00 29,5 92 12,00 25,5 90 2a 3,00 28,5 89 12,00 25,6 80 12 3,00 28,7 90 12,00 25,6 80 .

Table 11 - Influence on the growth height of barley;
vegetation experimen-t - soil treatment (Mitscherlich system) Plant height Compound no.Application rate kg/ha cm relative untreated - 55 100 41+) 3,00 52 95 _ 2 0,75 52 95 - 3,00 42 76 7 0,75 52 95 3,00 46 84 12 0,75 54 98 3,00 52 95 18 0,75 53 96 3,00 49 89 +) leaf treatment ~ 17 -Commencement of ~lowering normal for all varieties ~ and application rates a a a) o o o ~n o o o n o o o u~ o o o a~ ~ o o ~ a~ o o a~ ~ o o o ' ~ O O O
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li25S33 oOzO ~2,271 The use of the compositions according to the invention as growth regulators is no-t, however, limited to these exarllples.
The compositions accor~ing t~ th~ invention may ke used m the-fonm of conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The forms of application depend entirely on the purpose for which the agents are being used; in any case they should ensure a fine and uniform distribution of the active ingredientO The formulations are prepared in known manner, e.gO, by extending the active ingredient with solvent and/or carriers, employing if desired emulsifiers and dispersants; if water is used as diluent, other organic solvents may also be employed as auxiliary solventsO The main additives which are suit-able are solvents such as aromatics (e.g., xylene, benzene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., petroleum fractions), alcohols (e.g., methanol, butanol), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as natural flours (e.g., kaolins, aluminas, talc, chalk) and synthetic rock flours (e.g., highly disperse silicic acid, silicates);
emulsifiers such as non-ionic and anionic emulsifiers (e.g., poly-oxyethylene fatty alcohol ethers, alkyl sulfonates), and dispersantssuch as lignin, sulfite waste liquors and methyl cellulose.
Generally, the formulations contain from 0.1 to 95, preferably from 0.5 to 90, % by weight of active ingredient.
The formulations, or the ready-to-use preparations made there-from (solutions, emulsions, suspensions, powders, dusts, pastes or granules), are employed in conventional manner, e.g., preemergence, postemergence or as seed dressingsO
The application rates vary depending on the effect desired, and are from 002 to 5 or more, preferably, however, from 005 to 2, kg ' 30 of active ingredient per hectare.

The compositions according to the invention may, in these application forms, also be mixed and applied with other active ingredients, e~g., herbicides, insecticides, growth regulators and fung;cides, and with f ~J

li2S533 o o z t 32,271 fertilizers~ When mixed with growth regulators~ the spectrum ofaction is often increasedO In the case of some growth regulator mix-tures synergistic effects also occur, iOeO, the effectiveness Or the combination product is greater than the sum of the actions of its individual componentsO

90 parts by weight of compound 4 is mixed with 10 parts by weight of N-methyl-~-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

20 parts by weight of compound 2 is dissolved in a mixture con-sisting of 80 parts by weight Or xylene, 10 parts by weight of theadduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecyl-benzenesulfonic acid, and 5 parts by weight Or the adduct of 40 moles of ethylene oxide to 1 mole oP castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly dis-tributing it therein, an aqueous dispersion is obtained containing 0002% by weight oP the active ingredient.

20 parts by weight of compound 3 is dissolved in a mixture con-sisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil.
By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0O02% by weight of the active ingredient.

20 parts by weight of compound 4 is dissolved in a mixture con-sisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280C, and 10 parts by weight of the adduct of 40 moles of ethylene oxide ` ~125S33 oOzO 32,271 to 1 mole of castor oilO By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredientO

20 parts by weight of compound 5 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-~-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer millO By uniformly distributing the mixture in 20,000 parts by weight Or water, a spray liquid is obtained containing 0.1% by weight of the active ingredient.

3 parts by weight of compound 6 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained con-taining 3% by weight of the active ingredient.

30 parts by weight of compound 7 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and

8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

40 parts by weight of compound 8 is intimately mixed with 10 parts of the sodium salt of a phenolsulfonic acid-urea-formal-dehyde condensate, 2 parts of silica gel and 48 parts of water. A
stable aqueous dispersion is obtained. Dilution in 100,000 parts by weight of water gives an aqueous dispersion containing 0004 wt% of active ingredientO

20 parts of compound 9 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alco-~12553,3 OOZo 32,271 hol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts Or a paraffinic mineral oil. A stable oily dispersion is obtainedO

Claims

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A composition for influencing the growth of plants, which contains an, active compound of the formula (I) where R1 denotes unsubstituted or chloro-substituted unsaturated alkyl of 3 to 5 carbon atoms, 4-chlorobenzyl or 2,4-dichlorobenzyl, R2 denotes hydrogen or alkyl of 1 to 4 carbon atoms, R3 denotes fluoro, chloro, bromo, methyl, trifluoromethyl, phenyl or alkoxy of 1 to 3 carbon atoms, and n denotes one of the integers 0, 1, 2 and 3, the radicals R3 being indentical or different when n = 2 or 3, or an acid addition salt thereof, in admixture with a solid or liquid carrier, said composition containing from 0.5 to 90% by weight of active compound based on the total weight of the composition.

2. A composition for influencing the growth of plants, which contains 1-allyloxy-1-(4-bromophenyl)-2-(1,2,4-triazolyl-1)-ethane or an acid addition salt thereof, in admixture with a solid or liquid carrier, said composition containing from 0.5 to 90% by weight of active compound based on the total weight of the composition.

3. A process for influencing the growth of plants, wherein the plants or the soil are treated with from 0.2 to 5kg per hectare of a compound of the formule I, where R1 denotes unsubstituted or chloro-substituted unsaturated alkyl of 3 to 5 carbon atoms, 4-chlorobenzyl or 2,4-dichlorobenzyl, R2 denotes hydrogen or alkyl of 1 to 4 carbon atoms, R3 denotes fluoro, chloro, bromo, methyl, trifluoromethyl, phenyl or alkoxy of 1 to 3 carbon atoms, and n denotes one of the integers 0, 1, 2 and 3, the radicals R3 being indentical or different when n = 2 or 3, or an acid addition salt thereof.

4. A process for influencing the growth of plants, wherein the plants or the soil are treated with from 0.2 to

5 kg per hectare of 1-allyloxy-1-(4-bromophenyl)-2-(1,2,4-triazolyl-1)-ethane or an acid addition salt thereof.