PLANT GROWTH REGULATING COMPOSITIONS AND PROCESS FOR REGULATING PLANT GROWTH

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 R<1>, R<2> and R<3> 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 g ow h regulating compositions and process for regulating plant growth The present invention relates to plant growth composi¬ tions containing benzyl trialkyl ammonium salta and a proceaa for regulating the growth of planta. The benzyl trialkyl ammonium salta can be characterized by the general formula 1 2 3 wherein R , R , R^ are the same or different C -C, g alkyl , C 2~ σ iβ alken 3 rl » iaoalkyl, isoalkenyl, Y represents a non-phytotoxic anion. The compounds of the general formula I can be prepared by methods known per ae , e. g. by the following reaction acheme: solvent The compounds of the general formula I can be prepared v by reacting the appropriate benzyl halide (preferably chlorid or bromide) with the corresponding substituted trialkyl a ine 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 trie hy1 amine and benzyl chloride in a closed tube at 100 °C (Berichte der Deutach. Che . Ges. 10 £ 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. 7, 778). E de 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 bromi is prepared by reactin " 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, p 4-77). Plager and Maruel prepared later triethyl benzyl ammoniu bromide by reacting benzyl diethyl amine with ethyl bromide in benzene at 100 °C (J. Am. Chem. Soc. £8 /1923/ p. 2697). Kan or 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/ . 4122 ) . According to Marvel, Scott and A stutz tributyl amine and benzyl chloride are boiled in benzene to produce benzyl tributyl ammonium chloride (J. Am. Chem. Soc. 5 , 1 /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 olequivalent 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 sulfonat 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, cf. e.g. diethylmeth -(2-phenylalkyl) ammonium iodide in US-PS 3 539 632. Tetra- isopentyl 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 ai ilar compounda are claimed in DE-PS 2 415 981. In US-PS 4 343 647 plant growth regulating 3-trifluoro ethyl benzyl trialkyl ammonium aalta are deacribed. The plant growth regulating activity of variou substituted benzyl trialkyl ammonium and phosphoniu - 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 /I964/ 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. Bio 85, 277-286 and Lucas, Milboura and Tayler /1977/ Journa 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 g regulating activity, i.e. reduced the length of the inte of beans, and the transpiration and increased the crop. The common feature of the cited technical reference patent literature is, that the substituted benzyl trialk ammonium salts are described to reduce the height of the plant, the surface of the leaves, stimulate the flowerin 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 shor ontogenesis period of the plants and the dose range with which the plants do not get injured, is very narrow. Thus inspite of the favourable physiological activi of the compounds mentioned above, they could not become wideapread in the agriculture. Being aware of the favourable and unfavourable effe of the substituted benzyl trialkylammonium salts on the green house and free land tests were carried out with un substituted benzyl trialkyl ammonium salts which compoun are known but the plant growth regulating activity there 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 con¬ centration of the leaves was unchanged. Both tested compound stimulated the flowering. In case of the subsutituted benzyl trialkyl ammonium salts this effect co priaea in earlier flowering of the planta, whereas upon the effect of the unsubstituted benzyl trialkyl ammonium salts more flowers we formed on the planta. A significant difference was also foun in favour of the compositions of the invention wheny sprayin 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 sub¬ stituted benzyl trialkyl ammonium salts, though such toleran 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 C^ 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 caα 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 preferably 100-1000 g/ha. Favourable results can be expected when slightly in¬ corporating the compounds according to the invention into the soil. In order to achieve suitable effect the active zone ingredient concentration in the capillary root " near 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 in¬ gredient 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 con¬ centration of the compounds of the general formula I is in the range of 0.0001-90 % by mass, preferably 0.1-50 % by mas 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 togeth 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 mak their use easier. Such additives are e.g. protective colloid 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 surfacta e ulsifiers, 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, substitut phenols, such aa alkyl phenols, aryl phenols can be mentione 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 cante used together with other plant protecting agents, such as herbici 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 che¬ mically compatible with the unsubstituted benzyl trialkyl ammonium salts and do not influence unfavourably the biologi activity of each other. According to the invention plants are treated with a composition containing unsubstituted benzyl trialkyl ammoniu 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 for 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 hour 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, .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 alk iodide. Example 3 Benzyl trimethyl ammonium iodide 27 g. (0.2 mole) of benzyl dimethylamine are disso 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 diatille 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. et dried in a vacuo drying oven and white crystalline solid obtained, melting at 179-180 °C (decomposition). Similarl 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 (0.2 mole) of methyl benzene sulfonate are stirred under boiling in 250 ml ether for 3 days. When the reaction is minated a great part of the ether is distilled off in vac on a rotatory film evaporator, the precipitated white cry ne product is filtered off and dried in a vacuo drying ov 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 compound of the general formula I are contained in Table 1. Table I No. R J R' R- Anion Compound Melting point (o"0. ) 1. CH. CH- CH- Cl- Benzyl-trime hyl ammonium chloride 236-239 2. GH. CH- CH- Br- Benzyl-trime hyl ammonium bromide 231-233 3. CH. CH- CH- J- Benzyl trimethyl ammonium iodide 179-180 4. CH. CH- CH- cιo 4 - Benzyl t-dmethyl ammonium perchlorate 125-127 5. CH- CH- CH- gH^SO Benzyl trimethyl ammonium benzole 135-137 sulfonate 6. C 2 H 5 C 2 H 5 01- Benzyl triethy1 ammonium chloride 183-185 G 2 H 5 7. C 2 H 5 C 2 H 5 Br- Benzyl triethyl ammonium bromide 194-195 C 2 H 5 8. C 2 H 5 J- Benzyl triethyl ammonium iodide 168-170 °2 H 5 G 2 H 5 9. n C 3 H 7 ^Λ n°3 H 7 Cl- Benzyl tripropyl ammonium chloride 195-196 10. n C 3 H 7 n C 3 H 7 n°3 H 7 Br- Benzyl tripropyl ammonium bromide 187-188 11. n G 4 H 9 n°4 H 9 n G 4 H 9 Cl- Benzyl tributyl ammonium chloride 154-155 12. n C Λ n C 4 H 9 nC 4 H 9 Br- Benzyl tributyl ammonium bromide 173-175 13. 14. 15. CH- C 2 H 5 J- Benzyl methyl diethyl ammonium iodide 104-111 '2H t /table 1/ No. R R IT Anion Compound Melting point ( 16. CH n C H Q n°4 H 9 G ~ ~ Benzyl methyl dibutyl ammonium chloride 180-182 17. CH CH n G 8 H 17 G1 ~ Benzyl dimethyl octyl ammonium chloride 73-75 18. CH CH -(CH 2 ) 2 -C(CH 3 ) Br- Benzyl dimethyl neopentenyl ammonium bromide 198-200 19 CH ---3 *" CH 2" GH=GH 2 Br ~ Benzyl dimethyl allyl ammonium bromide 98-100 20. CH 3 n G 6 H χ3 n G 6 H 13 G ~~ Benzyl methyl dihexyl ammonium chloride 55-58 21. CH3 CH -CH 2 -CH-/CH 2 -CH Benzyl diraethyl-/2-ethyl-hexyl/-ammonium C 2 H 5 J- iodide 125-127 22. CH n G 8 H 17 n G 8 H 17 ~~" Benzyl methyl dihexyl ammonium chloride 66-68 23. C 2 H 5 C 2 H 5 n C 9 H i9 J * " Benzyl diethyl nonyl ammonium iodide 63-65 24. CH., CH -/CH 2 / 15 -GH Cl- Benzyl dimethyl hexadecyl ammonium chloride 60-63 Example 5 Water iscible 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 e ulsifier e.g. /4-/l,l,3,3-tetramethyl- -butyl/-phenyl/-hydroxy-poly-/o--cy/l,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 su 3 by mass of emulsifier, e.g. sodium oleyl methyl tauri /Ar opon 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 g 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 g 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 cli atized chamber, and exposed to light for Iβ hours, relative humidity: 75 %- daily temperature: -23 °C, hight temperature: 16 °C. 2 weeks after planting the plant 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 Treatment Plant height 16 days after Consumption of nutrie treatment solution cn _ ml _ _ 1. 8.75 100 6.24 100 2. 9.63 112 6.59 106 /table 2/ Treatment Plant height 16 days after Consumption of nutrient . 10.28 120 7.13 114 4. 9.16 107 6.32 101 5. 8.03 94 5.27 84 6. 6.24 73 4.59 74 7. 4.39 . 51 3.62 58 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 2 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 rela 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 afte the ratio of germinated grains was calculated. The test was per formed 4 times. Table 3 Effect of tri-n-butyl benzyl ammonium chloride on the germinatio of maize Treatments Germination % on the 6. day in % of the control 1. 100 2. 100 3. 125 4. 125 5. 145 6. 0 Germination of maize was stimulated at a dose of 200 mg-20 kg by 25-45 % upon using tri-n-butyl benzyl ammonium chloride. A total inhibition of germination was measured by increasing th 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: 1 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 2 85 % by mass ethanol. In the test the stock height, shuck number and raw shuck mass were evaluated. Table 4 Effect oftri-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 Treatment ac¬ Stock he: Lghi t Shuck number f Shuck mass tive ingredient g/ha expressed in % of the control Ξ 50 101.7 117 125 Ξ 100 106.3 115 125 E 200 101.0 112 112 Ξ 400 100.3 121 121 P 50 98.4 82 78 P 100 97.5 109 95 P 200 104.0 111 110 P 400 100.0 113 116 B 50 94.6 91 95 B 100 86.3 111 100 B 200 88.2 121 111 B 400 82.4 85 75 Evaluation on the 34. day after treatment. Table 5 Effect of tri-ethyl, -n-propyl, n-butyl benzyl ammonium chlorid on the tested qualitative characteristics on the basis of a tre ment in 2 x 3 leaves stage Treatment ac- Stock height Shuck number Shuck mass tive ingredient g/ha expressed in % of the control E 62.5 100. 9 99.0 88 E 125 102.6 107.3 113.2 Ξ 250 99.7 99.1 92. 5 Ξ 500 99.7 99.3 94.3 /table.5/ Treatment ac¬ Stock height Shuck number Shuck mass tive ingredient g/ha expressed in % ' < of the control P 62.5 103.1 109-3 125.2 P 125 104.8 107.4 118.9 P 250 103.7 116.3 106.9 P 500 106.6 109.7 104.4 B 62.5 96.2 89.5 81.1 B 125 100.0 115.3 109.6 B 250 106.2 119.3 123.8 B 500 100.0 101.5 98.6 Evaluation on the 30th day after treatment. Table 6 Effect of tri- ethyl-, -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 Treatment active Stock height Shuck number Shuck mass ingredient g/ha . expressed in % of the control H 100 95.9 102.0 111.6 M 400 99.5 106.9 118.5 Ξ 100 99.5 109.8 105.5 E 400' 96.8 98.0 98.6 P 100 99.5 102.5 •109.1 P 400 102.3 95.4 95.1 B 100 100.5 105.6 108.4 B 400 103.2 109.5 110.6 The evaluation was carried out on the 23rd day after trea 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 s -bean height, they rather increased same. The height increase was usually accompanied with the increase of the shuck numbe even the raw shuck mass was increased. Out of the various tr -alkyl benzyl ammonium chloride derivatives the activity of -n-butyl benzyl ammonium chloride was tested in free-land tes under small parcel conditions in soy beans. Test conditions : Type of soil: green field "chernozem" Green crop: winter wheat . Chemical fertilization: U 65 kg/ha (ammonium nitrate) P 2 0 5 110 kg/ha K 2 0178 kg/ha Weed-killing: 2,6-dinitro-ϊT,ΪI-dipropyl-4-trifluoro - ethyl aniline 1040 g/ha + ΪT-(p-bro -phenyD-U'-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 Treatment active Crop t/ha (air-dry weight) Change in % 1 0 4.15 4.20 4.40 4.25 4.25 100 - 2 125 5.01 4.90 4.90 4.85 4.95 116 3 250 5.00 5.03 4.90 4.96 4.97 117 4 500 4.53 4.65 4.50 4.53 4.55 107 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: 1 ~ 80 kg/ha (ammonium nitrate) P 2 0 5 150 kg/ha K2O 150 kg/ha Weed -killing: 2,6-dinitro-N,π-dipropyl-4-trifluoro-met 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. Treat ents: 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 Treatment active Crop t/ha (air-dry weight) Change in ingredient g/ha l.rep. 2.rep. 3.rep. 4.rep, average of the con 1. 00 4.64 4.36 4.58 4.26 4.46 100 2. 250 5.14 5.36 5.07 4.95 5.13 115 3. 500 5.41 5.29 5.60 5.30 5.40 121 4. 1000 4.53 4.29 4.61 4.07 4.37 98 5. 2000 4.01 3.78 4.00 3.85 3.91 87 6. 4000 3-29 3.46 3.35 3.09 3.29 74 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 nesting 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 fille 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 growt intensity of nettle leafed goosefoot (Chenopodium murale ) Treatments active Height/change Difference in % of ingredient g/ha cm x day" 1 the control 1. 0 0.31 100 2. 100 0.38 122 3. 200 0.40 124 4. 400 0.32 103 5. 800 0.28 90 6. 1600 0.20 64 *t shows that dimethyl tetradecyl benzyl ammonium chlorid acts as plant growth regulator. Up to 400 g/ha rate the daily growth rate of nettle leafed goosefoot (Chenopodiu murale) was increased by 21-29 , whereas by further increasing the dose th extent of growth intensity was by 10-36 % lower than that of th control. Example 15 Testing the effect of tri-n-butyl-benzyl ammonium chlorid (B) and tri-n-propyl benzyl ammonium chloride (P) on cott (Gossypiu hirsitu ) The test was performed in green-house on Acala art. The treatments were carried out at the beginning of budding and lowering. 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 compo sitions formulated as given in Example 12 and containing 10 % b 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 for¬ mation of cotton. Phenophase Treatment Flower Capsule Total Difference in % piece/ piece/ piece of the control plant plant Start of 1 3 6 9 100 budding 2 3 4 7 79 3 5 10 15 167 4 4 6 10 111 Start of flowering 1 6 3 9 100 2 4 3 7 78 3 5 5 10 111 4 4 7 11 122 5 2 5 7 78 6 6 8 14 155 7 178 It shows that both compounds display a strong effect on the crop formation of cotton

Claims: CLAIMS 1. Composition for regulating the growth of cultivated plant mainly of cereals, papilionaceae, sunflower, cotton and maize comprising as active ingredient 0.1-90 % by mass of a compound of the general formula wherei tand for G l" G l6 -'k-'aiglrfc or branched alkyl or C -C^g alkenyl and T stand for a nonphytotoxic anion, preferably halogen and an inert soli or liquid carrier or a solvent and optionally a surfactant and/ 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.

Inventors: GAAL SANDOR, GARDI IVAN, KARSAI JOZSEF, KISS GYOERGY, SEBESTYEN ENDRE, SIKI KAROLY, GAAL, SANDOR, GARDI, IVAN, KARSAI, JOZSEF, KISS, GYOERGY, SEBESTYEN, ENDRE, SIKI, KAROLY
Applicants: MEM NOEVENYVEDELMI ES AGROKEMI, MEM NOEVENYVEDELMI ES AGROKEMIAI KOEZPONT
Application year: 1986
Main classification: A01N33
IPC codes: A01N33