WO1986007237A1

WO1986007237A1 - Plant growth regulating compositions and process for regulating plant growth

Info

Publication number: WO1986007237A1
Application number: PCT/HU1986/000037
Authority: WO
Inventors: József KARSAI; Endre SEBESTYÉN; Sándor GAÁL; Iván GÁRDI; Károly SIKI; György KISS
Original assignee: Mém Növényvédelmi És Agrokémiai Központ
Priority date: 1985-06-05
Filing date: 1986-06-05
Publication date: 1986-12-18
Also published as: HUT41205A; HU196887B; DK46187D0; FI870441A; BR8606711A; EP0229098A1; FI870441A0; DK46187A

Abstract

Composition for regulating the growth of cultivated plants mainly of cereals, papilionaceae, sunflower, cotton and maize comprising as active ingredient 0.1-90% by mass of a compound of general formula (I) wherein R1, R2 and R3 are the same or different and stand for C1-C16 straight or branched alkyl or C2-C16 alkenyl and Y stands for a nonphytotoxic anion, preferably halogen and an inert solid or liquid carrier or a solvent and optionally a surfactant and/or dispersing agent and/or an additive influencing favourably the activity; and to the process for regulating the growth of cultivated plants.

Description

Plant growth regulating compositions and process for regulating plant growth

The present invention relates to plant growth compositions containing benzyl trialkyl ammonium salta and a process for regulating the growth of planta.

The benzyl trialkyl ammonium salta can be characterized by the general formula

(I)

wherein R¹, R², R³ are the same or different C_{1 -}C_{1 6} alkyl ,

C₂-C₁₆ alkeny l, isoalkyl, isoalkenyl, Y represents a non-phytotoxic anion.

The compounds of the general formula I can be prepared by methods known per se , e. g. by the following reaction scheme:

The compounds of the general formula I can be prepared by reacting the appropriate benzyl halide ( preferably chlorid or bromide) with the corresponding substituted trialkyl amine in the presence of a solvent at 20-150 °C or benzyl dialkyl amine and alkyl halide are reacted in a solvent or without any solvent according to the following reaction scheme:

The various benzyl trialkyl ammonium salts have been prepared since the second half of the last century.

Ladenburg and Struve described in 1877 the preparation of benzyl triethyl ammonium chloride and -iodide by heating triethyl amine and benzyl chloride in a closed tube at 100 °C (Berichte der Deutach. Chem. Ges. 10 p 312).

Collie and Schryver prepared benzyl trimethyl ammonium chloride in 1891 by heating trimethyl amine and benzyl chloride to boiling in abs. ethanol (J. Chem. Soc. 57, 778). Emde wrote an article about the preparation of the same compound (Archiv der Pharmazie, 247 - p 358).

Several benzyl trialkyl ammonium salts have been prepared. Authors described two kinds of preparation of the quaternary halogen salts: trialkyl amine is reacted with benzyl halide or benzyl dialkyl amine is reacted with alkyl halide. The first publication of some benzyl trialkyl ammonium halides which we tested, is given hereinbelow.

According to Hildebrandt benzyl trimethyl ammonium bromide is prepared by reacting trimethyl amine and benzyl bromide, whereas benzyl trimethyl ammonium iodide is prepared by reacting benzyl dimethyl amine with methyl iodide (Beitrage zur Chemischen Physiologie und Pathologie, 9, p 4-77).

Plager and Maruel prepared later triethyl benzyl ammonium bromide by reacting benzyl diethyl amine with ethyl bromide in benzene at 100 °C (J. Am. Chem. Soc. 48 /1923/ p. 2697).

Kantor and Hauser prepared benzyl tripropyl ammonium bromide by reacting benzyl bromide with tripropyl amine and benzyl tributyl ammonium bromide is prepared by reacting benzyl bromide with tributyl amine (J. Am. Chem. Soc. 73 /1951/ p. 4122).

According to Marvel, Scott and Amstutz tributyl amine and benzyl chloride are boiled in benzene to produce benzyl tributyl ammonium chloride (J. Am. Chem. Soc. 51 /1929/ p. 3640).

Benzyl triallyl ammonium bromide was prepared by Butler and Bunch (J. Am. Chem. Soc. 71 /1949/ p. 3120) by heating of a mixture of diallyl benzyl amine and allyl bromide in acetophenone.

The anion of the benzyl trialkyl ammonium salts can be not only halogen ion.

Schlegel obtained benzyl trimethyl ammonium perchlorate by crystallizing a molequivalent benzyl trimethyl ammonium chloride and perchloric acid from an aqueous solution (Ber. Deutsch. Chem. Ges. 64 /1931/ p. 1739) and in this article the preparation of benzyl trimethyl ammonium benzene sulfonate is also described by reacting dimethyl benzyl amine with methyl benzene sulfonate in ether.

The plant growth regulating activity of some substituted benzyl trialkyl ammonium salts is known, of. e.g. diethylmethyl- -(2-phenylalkyl) ammonium iodide in US-PS 3 539 632. Tetraisopentyl ammonium bromide and chloride are protected in

US-PS 3 580716, In US-PS 3 923 495 the lower alkyl carboxy benzyl trialkyl ammonium derivative and in US-PS 3 218 356 tributyl-2,4-dichlorobenzyl ammonium chloride are protected. Various tetraalkyl ammonium salts are protected in US-PS

2 740744. Substituted benzyl trialkyl ammonium halides are disclosed in US-PS 2 772 310 and various quaternary ammonium fluorides are protected in US-PS 3 277 118.

Plant growth regulating activity was disclosed for di-, trimethyl (cycloalkyl or alkenyl) ammonium salta in US-P

3 884 670. Chemically and biologically aimilar compounda are claimed in DE-PS 2 415 981. In US-PS 4 343 647 plant growth regulating 3-trifluoromethyl benzyl trialkyl ammonium aalta are deacribed. The plant growth regulating activity of various substituted benzyl trialkyl ammonium and phosphonium- salts has become known also from technical references apart from the patent references mentioned above (Preston and Link /1958/ Plant Physiol. 33. enc. Downing, Pelton and Melton /1964/ Abs. Am. Soc. Horticul. Sci. 25-28 Aug. p. 471. Amherst, Massachusetts, Chamberlain and Wain /1976 Annals of Applied Biology 82, 589-596). Farrabi-Aschtiane, Tayler and Wain /1977/ Ann. Appl. Biol. 85, 277-286 and Lucas, Milboura and Tayler /1977/ Journal of Horticultural Sci. 52, 239-244 found upon examination that a substituted benzyl trialkyl ammonium salt, namely 4-Chloro-benzyl tributyl ammonium bromide showed plant growth regulating activity, i.e. reduced the length of the internode of beans, and the transpiration and increased the crop.

The common feature of the cited technical references and patent literature is, that the substituted benzyl trialkyl ammonium salts are described to reduce the height of the plant, the surface of the leaves, stimulate the flowering, upon their effect the leaves are enriched in chlorophyll, transpiration is reduced and as a result the crop can be increased.

The substituted benzyl trialkyl ammonium salts show, however, the disadvantage of the risky use. They can be applied to the plants by spray only during the very short ontogenesis period of the plants and the dose range within which the plants do not get injured, is very narrow.

Thus inspite of the favourable physiological activity of the compounds mentioned above, they could not become wideapread in the agriculture.

Being aware of the favourable and unfavourable effect of the substituted benzyl trialkylammonium salts on the plants green house and free land tests were carried out with unsubstituted benzyl trialkyl ammonium salts which compounds are known but the plant growth regulating activity thereof has - to our knowledge - not been disclosed. We have unexpectedly found that the unsubstituted benzyl trialkyl ammonium salts caused the increase of the height of the treated plants, the surface of the leaves was not reduced, on the contrary it increased. The chlorophyll concentration of the leaves was unchanged. Both tested compounds stimulated the flowering. In case of the subsutituted benzyl trialkyl ammonium salts this effect compriaea in earlier flowering of the planta, whereas upon the effect of the unsubstituted benzyl trialkyl ammonium salts more flowers were formed on the planta. A significant difference was also found in favour of the compositions of the invention wheny spraying the plants with various doses of the test-compositions in different stages of the ontogenesis. It could be observed that the cultivated planta (such as soybean, winter wheat, sunflower) were more tolerant to the unsubstituted benzyl trialkyl ammonium salts in each phenological stage. J-To crop reduction or phytotoxic symptoms could be observed on the plants upon the spraying with the compositions according to the invention even in case of overdose or when it was not applied in the phenological atage suitable to get optimal effect. Such tolerance was not observed in case of the substituted benzyl trialkyl ammonium salts, though such tolerance is the precondition of the safe use of a compound.

The compounds of the general formula I can be used as plant growth regulators per se or combined with other plant growth regulators applying same simultaneously or separately mainly in case of C₃ plants by spraying it in the vegetative or generative stage of development.

The amount of the compounds of the general formula I is influenced by the species, variety and development stage and condition of the plant and all factors acting upon the plant, all of which are known for someone skilled in the art or can be determined by someone skilled in the art.

The compounds of the general formula I can be preferably used in the vegetative and/or generative development of the plants by spraying them on the foliage at a rate of 50-5000 g/ha. preferably 100-1000 g/ha.

Favourable results can be expected when slightly incorporating the compounds according to the invention into the soil. In order to achieve suitable effect the active ingredient concentration in the capillary root zonenear to the surface 0.5-50 mass unit related to 1 000 000 mass unit soil .

The compounds according to the invention can be used for seed dressing, preferably at a rate of 0.0005 g active ingredient related to 100 kg seeds. When increasing the dosage of the compounds according .to the invention to 2.0 g/100 kg seeds, phytotoxic symptoms can be observed in case of some plants, these symptoms, however, disappear in a later stage of development.

In the compositions according to the invention the concentration of the compounds of the general formula I is in the range of 0.0001-90 % by mass, preferably 0.1-50 % by mass, preferably 10-20 % by mass.

The products which can be directly used, can be prepared from the concentrated compositions by dilution. As the compositions according to the invention, the plant growth regulating compositions influencing the crop quality and quantity admixed prior .to use in a tank or spray equipment and if deaired the diluted compositions are considered too.

The compositions according to the invention are in the agriculture acceptable solid or liquid compositions, the preparation and use of which is possible due to the physical and chemical properties of the active ingredients.

The compositions contain the active ingredients together with in the agriculture acceptable solid or liquid carriers and optionally surfactants. The compositions may further contain additives which favourably effect the activity, such as reduce the decomposition of the active ingredients or make their use easier. Such additives are e.g. protective colloids, thickening agent, substances promoting adhesion, adhesivea, stabilizers of adsorptive solid carriers. As a carrier any natural or artificial organic or inorganic substance can be used which is acceptable in the agriculture.

As a solid carrier clays, talc, gypaum, sugar, salt, soda, chemical fertilizer, synthetic or natural silicates, silicic acid, dolomite, kaolin, vegetable or alga grist, starch etc. can be used. Aa a liquid carrier water, alcohols, esters, ketones, mineral oil fraction, aromatic,aliphatic or cyclic hydrocarbons, halogenated hydrocarbons, halogenated hydrocarbons, dimethylsufoxide etc. can be used. As surfactans emulsifiers, dispersing agents or wetting agents can be used and which can be ionogen or non-ionogen. As examples for the surfactants the salts of lignin sulfonic acid, the salts of phenol sulfonic and naphtalin sulfonic acid, poly- condensates of ethylene oxide and fatty alcohols and fatty acids or fatty acid amides, aryl alkyl sulfonates, substituted phenols, such aa alkyl phenols, aryl phenols can be mentioned. The solid compositions may be in the form of dusts, dusting agents or granulates. The liquid compositions may be in the form of solutions, emulsifiable concentrates, emulsions, suspension concentrates, wettable powders, spray powders or pastes.

The compositions according to the invention can te used together with other plant protecting agents, such as herbicides pesticides, fungicides, antibacterial agents, plant growth regulators and other compositions favourably influencing the amount and quality of the crop.

Generally any such plant protecting agent can be used together with the composition of the invention which is chemically compatible with the unsubstituted benzyl trialkyl ammonium salts and do not influence unfavourably the biological activity of each other.

According to the invention plants are treated with a composition containing unsubstituted benzyl trialkyl ammonium salt alone or simultaneously or subsequently with other pesticides.

The amount of the active ingredients ia chosen so as to achieve the most effective desired regulating effect.

The compositions are applied optionally in diluted form by conventional methods and equipments e.g. by spraying, dusting, vaporization, spreading.

Further details of the invention are illustrated by the following Examples.

The compounds in Table 1 were prepared by methods known per se. The typical preparation routes are shown by Examples. Chloride and bromide salts were prepared by reacting trialkyl amine with the corresponding benzyl halide. The melting point of the compounds correspond to reference data.

Example 1

Benzyl tributyl ammonium chloride A mixture of 92.68 g. (0.5 mole) of tributyl amine and 63.29 g. (0.5 mole) benzyl chloride is boiled for 10 hours in 250 ml of acetonitrile. When the reaction ia completed (thin layer chromatography showed no benzyl chloride traces) the solvent is distilled off in vacuo in a rotatory film evaporator, the obtained white solid is washed with somewhat diethylether and dried in a vacuum drying oven. Thus 148 g. of white microcrystalline substance is obtained (yield: 94.9 %) m.p.: 154-155 °C

Example 2

Benzyl tripropyl ammonium bromide

A mixture of 71.5 g. (0.5 mole) of tripropyl amine and 85.5 g. (0.5 mole) benzyl bromide are boiled for 6 hours in 200 ml. of chloroform. When the reaction is completed the solvent is distilled off in a rotatory film evaporator. Thus 153 g. of white microcryatalline product are obtained, m.p. : 187-188 °C. Similarly were prepared ammonium chloride and bromide compounds in Table 1. Quaternary ammonium iodide compounds were prepared by reacting dialkyl amine and alkyl iodide.

Example 3

Benzyl trimethyl ammonium iodide

27 g. (0.2 mole) of benzyl dimethylamine are dissolved in 200 ml. abs. ethanol and 28.38 g. (0.2 mole) of methyl iodide are added and the reaction mixture is boiled for 5 hours. When the reaction ia completed alcohol ia diatilled off in vacuo on a rotatory film evaporator. Thua 53.2 g. yellowish-white substance are obtained (yield: 96 %).

Some of the product is recrystallized from abs. ethanol, dried in a vacuo drying oven and white crystalline solid is obtained, melting at 179-180 °C (decomposition). Similarly were prepared quaternary ammonium iodide derivatives enlisted in Table 1.

Example 4

Benzyl trimethyl ammonium benzene sulfonate.

27 g. (0.2 mole) of benzyl dimethyl amine and 34.4 g. (0.2 mole) of methyl benzene sulfonate are stirred under boiling in 250 ml ether for 3 days. When the reaction is terminated a great part of the ether is distilled off in vacuo on a rotatory film evaporator, the precipitated white crystalli ne product is filtered off and dried in a vacuo drying oven. 54 g. (88 %) of white crystalline product are obtained. Part of the product is recryatallized from acetone, and the product melts at 135-137 °C Further prepared compounds of the general formula I are contained in Table 1.

Example 5

Water miscible concentrate

25 % by mass of active ingredient of the general formula I e.g. tri-n-propyl benzyl ammonium chloride 5 % by mass of polyoxyethylene/2/ sorbitol-monolaurate /Tuieen 20/ 70 % by mass water 00 % by mass

Example 6

Emulsifiable concentrate

8 % by mass of active ingredient of the general formula I e.g. trimethyl benzyl ammonium chloride 5 % by mass of emulsifier e.g. /4-/1,1,3,3-tetramethyl- -butyl/-phenyl/-hydroxy-poly-/oxy/1,2-ethanediol/ /Triton X-100/ 7 % by mass dimethyl formamide 0 % by mass methylenechloride 0 % by mass

Example 7 Wettable powder 0 % by mass of active ingredient of the general formula I e.g. tri-n-butyl-benzyl ammonium chloride 3 % by mass of dispersing agent, e.g. magnesium lauryl sulphate

3 % by mass of emulsifier, e.g. sodium oleyl methyl tauride

/Arkopon T/

4 % by mass colloidal synthetic silica 0 % by mass Example 8

Dusting agent

5 % by mass active ingredient of the general formula I e.g. triallyl benzyl ammonium bromide 5 % by mass colloidal synthetic silica 90 % by mass talc 100 % by mass

Example 9 Granulate

0.1 % by mass active ingredient of the general formula I e.g. tri-n-butyl ammonium chloride 99.9 % by mass attapulgite type carrier 100 % by mass

Example 10

Testing the effect of tri-n-butyl ammonium chloride through root

To plastic pots of a diameter of 12 cm air dry "chernozem" brown forest-soil was filled. The soil was poured with 50 ml of an aqueous solution of tri-n-butyl benzyl-ammonium chloride. The concentration of the solution changed as follows: 1./ 0 mg/1 tri-n-butyl benzyl ammonium chloride 2./ 0.625 mg/1 of tri-n-butyl benzyl ammonium chloride

(0.03/25 mg active ingredient/pot) 3./ 1.250 mg/1 of tri-n-butyl benzyl ammonium chloride (0.0625 mg active ingredient/pot) 4./ 2.5000 mg/1 of tri-n-butyl benzyl ammonium chloride

(0.125 mg active ingredient/pot)

5./ 5 000 mg/1 of tri-n-butyl benzyl ammonium chloride

(0.25 mg active ingredient/pot)

6./ 10 000 mg/1 of tri-n-butyl benzyl ammonium chloride

(0.5000 mg active ingredient/pot)

7./ 20 000 mg/1 tri-n-butyl benzyl ammonium chloride

(1.000 mg active ingredient/pot)

To each pot 5 sunflowers (Hellanthus annus) were planted, while the soil was filled up to 70 % water capacity.

The pots were placed to climatized chamber, and exposed to light for 16 hours, relative humidity: 75 %, daily temperature: 23 °C, hight temperature: 16 °C. 2 weeks after planting the plants were washed out of the soil. The roots were then soaked in 1/4 diluted Hougland nutrient solution in order to remove the soil particles remaining on the root. The test tubes were sealed with soft polyurethane foam in order to prevent evaporation and to support plants. The test tubes were placed in to sand and kept in shadowed green-house for 48 hours. The plant height and the consumption of the nutrient solution were determined.

Table 2

Effect of tri-n-butyl benzyl ammonium chloride through root on the height and the nutrient solution uptake m

It shows that tri-n-butyl benzyl ammonium chloride acts through the root.

The compound increased the height in a concentration of 625-2500 mg/1 at a rate of 0.003125-0.125 mg active ingredient/pot, and the nutrient uptake was increased simultaneously by the increase of the height and mass.

Byincreasing the concentratbn both the height and the nutrient solution uptake decreased.

Example 11

Testing of tri-n-butyl benzyl ammonium chloride as dressing agent

Pi 3901 hibride maize seeds were dreised with tri-n-butyl benzyl ammonium chloride formulated as given below: 10 % by mass of tri-n-butyl ammonium chloride

5 % by mass of polyoxyethylene (20) sorbitan nonolaurate (Tween 20) 85 % by mass of ethanol Treatments: 1./ untreated control 2./ tri-n-butyl benzyl ammonium chloride 20 mg/100 kg seeds 3./ tri-n-butyl benzyl ammonium chloride 200 mg/100 kg seeds 4./ tri-n-butyl benzyl ammonium chloride 2000 mg/100 kg seeds 5./ tri-n-butyl benzyl ammonium chloride 20 g/100 kg seeds 6./ tri-n-butyl benzyl ammonium chloride 200 g/100 kg seeds

The composition was diluted so as to apply 2 1 solution related to 100 kg seeds. 500 g seeds were dressed with proportionally reduced doses of dressing agent containing the active ingredient in the above given amount.

After drying 25-grains were placed to each Petri-dish of a diameter of 100 mm filled with sand and on the 6. day there after the ratio of germinated grains was calculated. The test was performed 4 times. n

Germination of maize was stimulated at a dose of 200 mg-20 g/100 kg by 25-45 % upon using tri-n-butyl benzyl ammonium chloride. A total inhibition of germination was measured by increasing the date to 200 g/100 kg. Example 12

Post-emergent activity of tri-n-alkyl benzyl ammonium chloride in soybeans under green-house conditions

To plastic pots of diameter of 12 cm air-dry "chernozem" brown forest-soil was filled. To the pots 5 Ewans soy-beans were sown and after emergence only 2 were left, so that approximately similarly developed plants were kept.

The plants were treated with various tri-n-alkyl benzyl ammonium chloride salts in different phenological stages. Phenological stages:

1x 3 leaves stage 2 x 3 leaves stage beginning of budding-flowering. Test compounds:

- tri-methyl benzyl ammonium chloride (M)

- tri-ethyl benzyl ammonium chloride (E)

- tri-n-propyl benzyl ammonium chloride (P)

- tri-n-butyl benzyl ammonium chloride (B) The active ingredients were formulated as follows:

10 % by mass of tri-n-alkyl benzyl ammonium chloride

5 % by mass polyoxyethylene (20) sorbitan monolaurate (Tween 20) 85 % by mass ethanol.

In the test the stock height, shuck number and raw shuck mass were evaluated.

Table 4 Effect of tri-ethyl, n-propyl, n-butyl benzyl ammonium chloride on the tested qualitative characteristics on the basis of a treatment in 1 x 3 leaves stage

Table 5 Effect of tri-ethyl, -n-propyl, n-butyl benzyl ammonium chloride on the tested qualitative characteristics on the basis of a treatment in 2 x 3 leaves stage

Evaluation on the 30th day after treatment. Table 6

Effect of tri-methyl-, -ethyl, -n-propyl, -n-butyl benzyl ammonium chloride on the tested qualitative characteristics at the beginning of the budding-flowering stage when applied by spraying

The evaluation was carried out on the 23rd day after treat- ment. The spray liquid was 500 1/ha in each test. The various tri-n-alkyl benzyl ammonium chloride salts under green-house conditions at the stage of 1 x 3 leaves did not reduce - with the exception of tri-n-butyl benzyl ammonium chloride - the soy-bean height, they rather increased same. The height increase was usually accompanied with the increase of the shuck number and even the raw shuck mass was increased. Out of the various tri-n- -alkyl benzyl ammonium chloride derivatives the activity of tri-n-butyl benzyl ammonium chloride was tested in free-land test under small parcel conditions in soy beans.

Test conditions : Type of soil: green field "chernozem"

Green crop: winter wheat . Chemical fertilization: N 65 kg/ha (ammonium nitrate)

P₂O₅ 110 kg/ha K₂O 178 kg/ha Weed-killing: 2,6-dinitro-N,N-dipropyl-4-trifluoro-

-methyl aniline 1040 g/ha + N-(p-bromo- -phenyl)-N'-methoxy-urea 1000 g/ha Species: Pioneer 1667

Stock number: 320 000 stock/ha

Parcel size: 2 x 10 m

Spray liquid amount: 2201/ha Time of treatment: beginning of budding Treatments: 1./ untreated control 2./ tri-n-butyl benzyl ammonium chloride 125 g/ha 3./ tri-n-butyl benzyl ammonium chloride 250 g/ha

4./ tri-n-butyl benzyl ammonium chloride 500 g/ha

Table 7

Effect of tri-n-butyl benzyl ammonium chloride on soy-bean's crop when applied by spraying at the stage of budding

rep. = repetition

The soy-bean crop was increased by 7 to 17 % by applying tri- -n-butyl benzyl ammonium chloride at a rate of 125-500 g/ha by spraying. A more intensive increase (16-17 %) was observed in case of the lower rate (125-250 g/ha).

Example 13

Effect of tri-n-butyl benzyl ammonium chloride in green- -peas (Pisum satinum) The test was carried out in free-land under small parcel conditions. lest conditions: Type of soil: green field "chernozem" Green crop: sugar-beet Chemical fertilization: N 80 kg/ha (ammonium nitrate)

P₂O₅ 150 kg/ha

K₂O 150 kg/ha Weed-killing: 2,6-dinitro-N,N-dipropyl-4-trifluoro-methyl aniline 780 g/ha

Species : emerald

Stock-number: 580000 stock/ha

Parcel size: 2 x 10 m

Spray liquid amount: 2201/ha

Repetitions: 4

Time of treatment : beginning of flowering Spray liquid was prepared from the composition containing 10 % by mass active ingredient formulated as disclosed in Example 12.

Treatments: 1./ Control

2./ tri-butyl benzyl ammonium chloride 250 g/ha 3./ tri-butyl benzyl ammonium chloride 500 g/ha 4./ tri-butyl benzyl ammonium chloride 1000 g/ha 5./ tri-butyl benzyl ammonium chloride 2000 g/ha 6./ tri-butyl benzyl ammonium chloride 4000 g/ha

Table 8

Effect of tri-n-butyl benzyl ammonium chloride on the green-pea crop when applied by spraying at the beginning of flowering % trol

The table shows that when using tri-n-butyl benzyl ammonium chloride in peas by spraying it at the reate of 500 g/ha at the beginning of flowering the crop is increased by 15-21 %. By further increasing the sprayed liquid a crop reduction is caused.

Example 14

^Testing dimethyl tetradecyl benzyl ammonium chloride The test was carried out in green-house with nettle leated goosefoot (Chenopodim murale). Settle leated goosefoot of average height of 10 cm were planted to pots of a diameter of 12 cm filled with "chernozem" brown forest soil. When the seedlings took root their height was measured and the seedlings were, treated with the following doses of dimethyl tetradecyl benzyl ammonium chloride. 1./ untreated control

2./ dimethyl tetradecyl benzyl ammonium chloride 100 g/ha 3./ dimethyl tetradecyl benzyl ammonium chloride 200 g/ha 4./ dimethyl tetradecyl benzyl ammonium chloride 400 g/ha 5./ dimethyl tetradecyl benzyl ammonium chloride 800 g/ha 6./ dimethyl tetradecyl benzyl ammonium chloride 1600 g/ha. Spray liquid: 500 1/ha

On the 14. day after treatment the height was determined. The extend of the height change for one day is included in the following table 9.

The test was repeated 12 times.

Spray liquid was prepared from the composition containing 10 % by mass of active ingredient formulated as given in Example 12. Table 9

Effect of dimethyl tetradecyl benzyl ammonium chloride on growth intensity of nettle leafed goosefoot (Chenopodium murale) -

^It shows that dimethyl tetradecyl benzyl ammonium chloride acts as plant growth regulator. Up to 400 g/ha rate the daily growth rate of nettle leafed goosefoot (Chenopodium murale) was increased by 21-29 %, whereas by further increasing the dose the extent of growth intensity was by 10-36 % lower than that of the control.

Example 15

Testing the effect of tri-n-butyl-benzyl ammonium chloride (B) and tri-n-propyl benzyl ammonium chloride (P) on cotton (Gossypium hirsitum) The test was performed in green-house on Acala art. The treatments were carried out at the beginning of budding and flowering. Each treatment represented 12 plants each. Treatments: 1./ Untreated control 2./ B 62.5 g active ingredient/ha 3./ B 125 g active ingredient/ha

4./ B 250 g active ingredient/ha Beginning of flowering

1./ untreated control

2./ B 62.5 g active ingredient/ha

3./ B 125 g active ingredient/ha

4./ B 250 g active ingredient/ha

5./ P 62.5 g active ingredient/ha

6./ P 125 g active ingredient/ha

7./ P 250 g active ingredient/ha Spray liguid: 2501/ha. Spray liquid was prepared from compositions formulated as given in Example 12 and containing 10 % by mass of active ingredient. Evaluation was carried out on the 40. day after the first treatment and on the 20. day after the 2. treatment.

Table 10 Effect of tri-n-butyl benzyl ammonium chloride (B) and tri-n- -propyl benzyl ammonium chloride (P) on flower and capsule formation of cotton.

It shows that both compounds display a strong effect on the crop formation of cotton.

Claims

1. Composition for regulating the growth of cultivated plants mainly of cereals, papilionaceae, sunflower, cotton and maize comprising as active ingredient 0.1-90 % by mass of a compound of the general formula

(I)

wherein R¹, R² and R³ are the same or different and stand for

C₁-C₁₆ straight or branched alkyl or C₂-C₁₆ alkenyl and Y stands for a nonphytotoxic anion, preferably halogen and an inert solid or liquid carrier or a solvent and optionally a surfactant and/or dispersing agent and/or an additive influencing favourably the activity.

2. Process for regulating the growth of cultivated plants, mainly cereals, sunflower, papilionaceae, cotton and maize comprising a) treating the plants in the vegetative and/or generative stage of development with a compound of the general formula I - wherein the substituents are as given in claim 1 - at a rate of 50-5000 g/ha, preferably 100-1000 g/ha, or b) treating the soil before or after seeding the seeds or seedlings of the plantsat a rate of 350-2000 g/ha or c) treating the seeds with a compound as given in claim 1 at a rate of 0.02-40 g/100 kg seeds, preferably 0.2-20 g/100 kg seeds.