DE1792153A1 - Plant growth agent - Google Patents

Description

DR. ELISABETH JUNG, DR. VOLKER VOSSIUS. DIPL.-ING. GERHARD COLDEWEY

a MDNCHEN23 ■ 3 I E O E S8 T RA8SE 26 ■ TE L EFON 34S067 ■ TELEGRAM M-ADRE8SE: IN VE NT / M ONCH EN

July 29, 1968

u, Z,: D 478 FMC 4143 Vo-kä

PMC CORPORATION New York, N.Y., Y, St.A.

^w plant growth agent "

The invention relates to a new plant growth agent that is characterized by a phenylfuroian content.

The structure of phenylfuroxan, also known as phenylfurazan oxide; is not exactly known. The following formulas are currently being discussed

or

The connection has long been known. Your manufacture was written by R. Scholl in Reports of the German Chemical Society "Volume 23 (1Θ90), Page 3490, G. PonJsio, * GazE, ohim. ital. ^ Volume 66 (1936), page 114 and H. Wieland in • Liebig's Annalen der Chemie ^ Volume 424 (1921), page 107

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wrote.

According to the invention it was found that when applying Phenylfuroxan on plants which are either in the growth stage or in the dormant stage, new and unexpected plant growth regulation effects are obtained. "This compound causes the variousetea and atypical reactions in plants, which are not caused by known plant growth agents, ZoB. Phenylfuroxan produces an early strain development and the treated plants produce ripe fruits much earlier than untreated plants, The connection also promotes early help from the plants the compound an effective fruit thinner, the treatment with phenylfuroxane in certain concentrations results in a significant increase in delivery size. The connection promotes also an early termination of the dormant buds. Numerous other interesting and valuable effects on plant growth can be achieved in appropriate treatment with phenylfuroxane Stage of growth, the appropriate concentration and type of treatment. It has been found that virtually all treated plants show some kind of reaction to phenylfuroxane when this compound is applied during certain developmental stages.

According to H. Wieland, "Liebigs Annalen der Chemie] Volume 424 (1921), page 107," Phenylfuroxan can be obtained from Ethynylbensol by treatment with nitrous acid or naoh 9 · Ponzlo "Gazz. chim. ital / jBand 66 (1936), page 114, by implementing

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Phenylglyoxime can be produced with nitrogen tetroxide, phenylglyoxime can according to Ponzio and Avogadrο, ^v Gazz. chim, Ital.'j Volume 53 (1923), page 25. Instructions for the production of phenylfuroxane are given below.

Regulation 1

A solution of 30.0 g of ethynilbenzene in 60 ml of ether and 90 ml of hexane is mixed with the same volume of cold, saturated aqueous sodium nitrite solution. The mixture is kept at 7 to 12 ^° C., and 250 ml of 4-η sulfuric acid are added dropwise at this temperature over the course of 4 hours. The reaction mixture is left to stand for a further hour at this temperature and then the crystals are filtered off. The crystals are washed with water until all of the sodium sulfate has dissolved. The remaining crystals are washed with hexane and ether. Yield 9.0 g Phenylfuroxan from Pp. 109 to 112 ⁰ C.

Regulation 2

A solution of 24 g of hydroxylarain hydrochloride and 48 g of sodium acetate in 75 ml of water is added to a solution of 50 g of phenylglyoxal aldoxime in 150 ml of ethanol. The mixture is heated on the steam bath for 4 hours, then evaporated to almost dryness under reduced pressure and then filtered. The crystals are f 'action crystallized from aqueous ethanol. There are 12.0 g amphi-phenyl jlyoxim of mp. 175-176 ⁰ C and 12.0 g anti-Phenylglyoxim from Pp. Receive from 178 to 180 ⁰ C.

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12 g of amphi-phenylglyoxime are dissolved in 200 ml of anhydrous ether. The solution is ^{cooled to 0} ° C., and at this temperature a mixture of dinitrogen tetroxide and anhydrous nitrogen is introduced into the stirred solution over a period of 2 hours. The reaction mixture is stirred for a further 2 hours, and then the crystals are filtered off. The crystals are washed with anhydrous ether and dried. 8.5 g of phenylfuroxane are obtained which, after recrystallization from benzene, ^{clicks at 109 to HO 0} C,

C ₈ H ₅ N ₂ O ₂ ; calc .: C 59.26, H 3.73 »N 17 * 28; found: C 59.27, H 4.03 _Γ Ν 17.36 «

The examples illustrate the invention.

example 1

Controlling the growth of lima bean plants A mixture of equal parts of silt loam and sandy loam is placed in shallow bowls 7-6 cm high. The seeds of lima beans are then placed about 2.54 cm deep in the ground. The dishes are watered and placed in a greenhouse for 2 weeks until the first three-part leaf spreads. With the exception of a control plant, the plants are then sprayed with a solution of Phenylfuroxan in aqueous acetone in an amount which corresponds to 3.63 kg active ingredient per 0.405 ha _t planting. Both the treated and the untreated plants are kept in the greenhouse while the effect of the treatment is observed. Within 7 days after the treatment, new species formed in the leaf axils of all treated plants

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BAD ORIGINAL * ?; 10 OA3

säl; for leaves that are divided into three parts. This has doubled the three-part leaves in treated plants compared to untreated plants result in this increase in growth was obtained without significant damage to the apical meristems * Usually this type of pro- » liferation in the leaf axils only in plants derived from the vegetative pass to the generative stage, or in plants in which the apical meristem on mechanical or has been chemically damaged or destroyed.

Example 2

Consumption of Tobacco and Bean Plants Similar results were observed in tobacco plants and bean plants of the cultivar Black Valentine.

Phenyl

GemäsB Example 1, the treatment with / furoxane in an amount corresponding to I _5, performed 81-3 * 63 kg / 0.405 ha.

Pure, "each treatment are 4 bean plants in the first three«

sswel
split leaf stage and / 11.4 cm high tobacco plants with 7 to 10 real leaves are used. 19 days later, the following initial biological responses were observed:

The treated bean plants showed new axillary growth and they had 3 to 7 tripartite leaves each Plant while the control plants had 2 to 3 tripartite leaves at this time.

Subsequent observations on the treated plants showed that the flowers and fruit development proceeded normally.

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In the tobacco plants, not only normal new apical growth developed but also all leaf axils developed runner growth. The tobacco control plants and the treated tobacco plants were then grown on cut off the tip to determine the effect of the treatment on the growth of plants, mechanically described below Side shoot growth were induced. After the tips of the plants had been cut off, the control plants were carried out Side shoot growth on all leaf axils, while the treated plants do not have any pronounced reinforcement of the existing ones Showed lateral shoot growth on the more basal leaf axils. All plants, solitary of the control plants, developed a predominant new apical growing stem from the edge of the stem tip, of a further development of side shoot growth suppressed the more basal nodes, these new apicals Stems caused flower formation after several leaves had developed. 22 days after removing the top of the plants a plant treated with 1.81 and 3.63 kg / O, 405 ha, respectively was developed, well-formed flower buds at the tip of the new apical stem. JDIe second slice of the Treatment with 3.63 kg / 0.405 ha had with the flower bud formation started on the 33rd day and the second plant treatment with 1.81 kg / 0.405 ha on the 40th day. The control plants had budding on the 48th day and 54th day, respectively began. All plants bloomed and set normal seed heads.

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Example 3 Effect on blooming of tobacco plants.

The interesting effect of different doses of phenylfuroxane results from the experiments below. Phenylfuroxan in aqueous acetone solution was available as a foliar spray Tobacco plants in quantities corresponding to 0.227 »0.454 and 0.907 kg / 0.405 ha applied. At the time of application, the plants were 3 to 4 inches tall and 9 to 10 inches tall Leaves. The plants were planted in 10.16 cm large pots «. 2 plants were used for each experiment. The following results were obtained «

Side shoot growth started on the second day at all treatment concentrations. «Although new shoot leaf growth developed to a point _? on which a certain leaf shape could be determined, no further development worth mentioning took place. The apical growth of the plants continued. The 0.907 kg / 0.405 ha treatment produced minor necrotic stains on the younger leaves that were present during the treatment period. The lower treatment concentrations showed no apparent phytotoxicity. The 0.227 kg / 0.405 ha treatment required an initial increase in height gain, while the higher treatment concentrations generally inhibited height gain.

29 days after treatment, the plants became larger "" pots implemented. On the 35th day after the treatment, both

Phenyl de plants that received the 0.227 kg / 0.405 ha treatment with / furoxan received well-developed flower buds. On the 40th day continued

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on a plant that received a 0.907 kg / 0.405 ha treatment, Bud formation. On the 47th day, the second plant, which received a 0.907 kg / 0.405 ha treatment with furoxane, continued received, bud formation a. One of the plants that received a 0.454 kg / O, 405 ha treatment had at this time also started budding. The description of all plants at this time is given in Table I.

Table I.

reaction of tobacco plants , I. State on the foliage treatment Plants in
blossom D ο sis II plants
height, cm of the plants 47 days after
the treatment Yes 0.227 kg / 0.405 Ha , ι 73.7 blossoms
bud Yes II 76.2 Yes no 0.454 kg / o _t 405 Ha , I. 48.26 Yes no II 53.3 no no 0.907 kg / 0.405 Ha I. 61.0 Yes Buds open calibrated II 69.9 Yes no Control area » 55.9 Yes no 50.8 no no

Both control plants began to bud on the day 7 days after the observations summarized in Table I ₀

Example 4 Growth control of strawberry plants

Phenylfuroxan in acetone solution according to Example 1 was found in concentrations of 0.113, 0.227 and 0.454 kg / 0.405 ha

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Strawberry plants of the Sparkle variety in the early bud stage upset. The treated plants generally began to form flowers and the subsequent fruit development much more quickly than untreated plants.

example 5 Control of the growth of tomato plants

An aqueous acetone solution that produces 138 ppm phenylfuroxane » held, was planted on 12 individually planted tomato plants in pots California 145-B grade. The Lomato Plants were 8.89 cm high and had 7 to 8 true leaves at the time of treatment. On all the plants were Flower buds hardly recognizable.

The reaction of the plants to the chemical treatment was carried out a month later. The chemical treatment did not reveal any apparent phytotoxicity, but inflorescence development was delayed. The total number of fruit clusters and the total number of tests and flowers on the plants was the same as that of the control plants and the treated plants Plants of the same size as the control plants however had 46 # more fruit with a pressure gauge of 5 mm than the treated plants.

One month after the first treatment, the previously treated plants were treated again with a solution of 138 ppm phenylfuroxane. 26 days later the plants were examined for fruit development. The second treatment increased the fruit development considerably, and the treated plants showed 23 ° k more tests with one

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5 mm in diameter on all control plants. 5 of the treated plants had fruits with a diameter of more than 5 mm on the third and fourth cargo level, while none of the control plants had fruits with a diameter of 5 mm at the second infructescence. These results explain the influence of the application time as well as the dose the type of effect obtained.

Example 6

Effect on the stage of growth for the period of application A further investigation was carried out to determine the various effects of phenylfuroxan on tomato plants

Stages of growth carried out.

Bonny Best tomatoes were sown in flower pots, and after the plants came out, the seedlings were thinned out so that each flower pot contained only one plant. The planting took place at lateral intervals, so that at the time of treatment there were 5 plant wake stages available. A description of these growth stages is given in Table ΙΣ below. Then the plants with an aqueous Acetonlöeung of Phenylfuroxan were 0.1 fl of a wetting agent (PoljroocyÄthylensorbitanmonolaurat) and 5.0 ppm and 50.0 ppm Bbmmfltwcoxma. contained sprayed in an amount corresponding to 2.83 m / 0.405 h *. For each stage of growth and for each treatment were 2 Plants used. 2 plants which had only been sprayed with a 0.1% solution of the wetting agent in aqueous acetone were used as control plants. the

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Plants were placed in the greenhouse one and 50 days examined after treatment. The results are shown in Table IX.

Table II Effect on Fruit Development of Tomato PLANEON

dose

Number, the number of the Pruchtge-Frucht-Fruits ** weight, g stands

Stage of growth (I) * 12th 2 3.7 5.0 ppm 14th 5 11.3 50.0 ppm 14th 0 0.0 control Stage of growth (2) * 15th 1 0.7 5.0 ppm 17th 3 24.2 50.0 ppm 12th 1 8.5 control Stage of growth (3) * 18th 10 270.5 5.0 ppm 16 5 75.3 50.0 ppm 15th 1. 22.2 control Wholesaling stage (4) * 17th 10 300.9 5.0 ppm 10 11 303.2 50.0 ppm 11 7th 261.1 control Growth 8tadiuB 11 10 400.4 5.0 ppm 12th 9 302.2 50.0 ppm 10 8th 435.5 Font roll

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* Growth stage age after sowing,

Weeks

(1) Development of the cotyledons. 1

(2) Two foliage leaves (real leaves)

2 _r 54 «3.17 cm long 2

(3) Three to four real leaves

(third and fourth sheet
If9 - 3.17 cm long; 3

(4) Five to six real leaves 4

(5) Seven to eight real leaves,

smallest buds of the first
Infructescence hardly visible 5

** Fruits more than 5 mm in diameter.

Show the results summarized in Table II results indicate that the fruit development is greatest when Phenylfuroxan is applied in the growth stage (l) _f (3) and (4). The effect is less in the growth stages (2) and (5). In general, the treated plants are morphologically advanced compared to the untreated control plants. This shows that phenylfuroxane promotes the early ripening of tomatoes. The optimal treatment with phenylfuroxan not only increases the number of fruits but also the size of the fruit is increased considerably.

Example 7 End of dormant buds in apple trees

During the growth period, apple trees produce new vegetative buds and fruit buds during the months of July and Auguste These buds are dormant until next spring. To the To eliminate bud dormancy and initiate new growth,

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BATH ORIGINAL

the trees must be exposed to cold temperatures for a certain period of time. The length of this period depends on the variety of apple, but at least 2 months at temperatures averaging below 8.9 ⁰ G are generally required. If the trees are not cooled to the necessary extent _f they develop slowly leaves and irregular flowers, or they do not show any growth * This example illustrates the use of Phenylfuroxan to eliminate dormancy in apple trees not cold temperatures · ren auegesetzt were.

Small, two to three year old Mclntosh apple trees were planted in pots in October before the onset of a prolonged period of low temperature and kept in the greenhouse at temperatures above 15.6 C during the winter. In late April, the leaves and stems were sprayed the trees with an aqueous acetone solution of Phenylfuroxan which contained 0.1 $> of that in Example 6 surfactant and 5.0 and 50.0 ppm Phenylfuroxan, The trees were an average of 66 cm high and they had a trunk diameter at the base of 1.27 cm. The trees retained their leaves from the previous vegetation and had dormant vegetative buds. Two trees were used for each concentration, and two trees sprayed with 0.1 # acetone aqueous solution of the wetting agent were used as controls. The results are shown in Table III.

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D ο s i S. I. 5.0 ppm, II I. 50.0 ppm, II I. Control, II

Table III
Effect on the dormancy of apple trees

Time from the treatment to the new jfaohstum

7 weeks 7 woohen

5 weeks

5 weeks, flowers

no new growth after 6 months · »

no new growth after 6 months

The results compiled in Table III show that Apple can be grown in climates that were previously unsuitable for this.

Example 8

Fruit thinning and increase in fruit size The effect of phenylfuroxan as a thinning agent and for increasing the size of the fruit is explained using cherries and peaches. The following results show that different plant species are influenced somewhat differently by the dose and the time of treatment, but that the regulation of phenylfuroxane is always recognizable.

A 15 ^ solution of phenylfuroxane in a 1 t 1 mixture of ethanol and polyethylene glycol voa molecular weight 500 to 600 was used to prepare solutions containing 50.0 and 500.0 ppm phenylfuroxane. These solutions

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were sprayed on specific branches of 24 year old Windsor cherry trees that were in full bloom. Separate trees were used for each concentration, and repeat treatments were on a branch or a group of branches on the opposite side of the same tree. Branches of a third tree were sprayed with a control sample to determine the effect of the solvent.

Significant rejection of the fruit was observed within 10 days after the treatment with the 500 ppm dose, which 5 weeks later led to a total fruit thinning of 50 #. Treatment of the solution with 50 ppm phenylfuroxane, on the other hand, did not result in fruit thinning, and the fruits on the branches that received this treatment ripened more quickly and the cherries obtained were about 20 % larger than those on the untreated control branches. The results are in (Compiled in Table IV. Results are the average of two replicates 45 days after treatment.

Table IV

Effect of the treatment on fruit set and fruit size

se with cherry trees

Dose starting- final total weight

borrowed fruit set fruit pro

Number of _abBolut d. weight, cherry, blossoms ^aDB0J - ^ut * gg

^f / 0.0 ppm 1823 980 53 2041 2.10 '00, 0 ppm 1869 525 28 921 1.75 control 1844 884 48 1616 1.83

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Similar results were obtained with peaches of the shark variety Virtually complete thinning was achieved on branches obtained with a 500 ppm phenylfuroxane solution treated with complete petal fall «Treatments with solutions containing 50 ppm phenylfuroxane at full petal fall or 8 days after full petal fall produced one Fruit size increase from 18 to 23 # without fruit thinning.

The systemic activity of phenylfuroxan was found on peach trees observed with treated and untreated branches. The untreated branches were protected against drifting Shielded against spray. Those branches near the branches that were treated with the 500 ppm phenylfuroxane solution were not thinned but developed fruits about 23 # larger than those on the distal ones Branches.

Except for the uses described in more detail above there are numerous other interesting and economically important uses for the invention Plant growth agents “This group of representative experiments on different types of plants describes some of the ways phenylfuroxane changes or enhances normal plant development. It can be seen that the application of phenylfuroxan increased development at any of the various stages of wakefulness of plants, whereby the optimal treatment con-

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sentration depend on the respective growth stage of the plant aov / ie on the type and variety of the plant. Repeated treatment of the plants offers further possibilities for plant growth regulation. For example, the plant growth agent can be used in the early stages of growth to produce early flower formation, and a second application for flowering can further intensify fruit development * Bs can both delay and accelerate it plant growth and maturity can be achieved. The natural rest not only of fruit trees but also of potato tubers and flower bulbs Z ₀ B ₀ can be interrupted by the use of phenylfuroxane. “Early fruits, flowers and vegetables can be preserved and the annual yield can be increased. Controlled ripening can facilitate mechanical harvesting. Garden crops and crops can be improved. The success of grafting can be improved with grafting. The shape of flowers can be improved by encouraging the emergence of rare shoots »There are other uses for the botanist«

For all application concerns, of course, an effective one should be The amount and concentration of phenylfuroxane used to achieve the desired result, with the growth stadiura in the respective plant must be observed muse «The same plant can be treated once or several times for the same or different purposes«

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The treatment of the plants with phenylfuroxane can be carried out physically, for example by immersion treatment of the tubers, bulbs or cuttings or, for example, by treating the leaves, bark or trunks or by treating the soil. The active ingredient can be used in various fora. For example, together with auxiliary substances and carriers, such as are usually used to facilitate the dispersion of active substances for use in agriculture. Here, the known fatsache into account _t that the formulation and mode of application may affect a chemical agent and its activity in a particular type of application · To Phenylfuroxan example, can a solution or dispersion in aqueous or non-aqueous media, as dusts, ale wettable powders, emulsifiable concentrate or granules can be processed depending on the type of application. The plant growth agent of the invention can be applied as a spray, dipping agent, stowage agent or granulate at the site of the desired wachate regulationc. The plant growth agent of the invention can contain from 0.0005 to 95% by weight or more of the active ingredient. The active ingredient can be used in amounts that are less than 0.22? kg to more than 90.7 kg / 0.4-05 ha.

Dusts are mixtures of the active ingredient with finely divided solid substances such as talc, attapulgite, kieselguhr other organic or inorganic solids that serve as dispersants and carriers for the active ingredient. These finely divided solids have a «

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average part size less than about 50 microns. A typical dust suitable for the purposes of the invention contains 1.0 part phenylfuroaan and 99 »0 Share talc.

Wettable powders are in the form of finely divided particles, which can be easily dispersed in water or other dispersants. The wettable powders are applied to the plant Applied either as a dry dust or as an emulsion in water or another liquid. Typical Carriers for wettable powders are e.g. fuller's earth, kaolin clays, silica and other highly absorbent, easily wettable ones inorganic diluents. Wettable powders are generally made to be about 5 to 80 56 Active ingredient included, depending on the absorption capacity of the Carriers. They usually also contain a small amount of a hardening, dispersing or emulsifying agent. For example, a usable wettable powder contains 20.8 parts Phenylfuroxan, 77.9 parts palmetto clay and 1.0 part sodium lignosulfonate and 0.3 part of a sulfonated aliphatic polyester as a wetting agent.

Other suitable preparations for treating plants are the emulsifiable concentrates, i.e. homogeneous liquid or pasty masses which can be dispersed in water or other media are. These preparations can consist of phenylfuroxane with a liquid or solid emulsifier, or they can also use a liquid carrier such as xylene, high-boiling aromatic heavy gasoline, isofuron or others

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contain non-volatile organic solvents. For the treatment of plants, these concentrates are dispersed in water or other liquids and generally sprayed onto the area to be treated. The concentration of this active ingredient depends on the type of application. In general, the preparations contain $ 0.0005 to $ 95> active ingredient.

Typical wetting agents, dispersants or emulsifiers, as used for agricultural preparations, are, for example, the alkyl and alkylarylsulfonates and _{sulfates and their sodium salts 3,} polyethylene oxides, sulfonated oils, fatty acid esters of polyhydric alcohols and other surface-active compounds. If a wetting agent is used _for it is generally present in an amount of 1 to 15 Grew "- # of the preparation before.

Other suitable preparations are simple solutions of the active ingredient in a solvent in which the active ingredient is completely soluble at the desired concentration, such as acetone or other organic solvents. Granules relatively coarse grain size are of particular value for use from the air to penetrate cover crop, The plant growth agents of the invention can also be used from aerosols in conjunction with a low boiling propellant.

The crop protection agents of the invention may contain other known agricultural chemicals such as Ineekticide, Fungicide. Nematocides and fertilizers. Except

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They can also contain certain plant hormones, such as native auxins, anti-auxins, gibereilins and kinins, in order to achieve increased growth regulation effects. For example , the combination of phenylfuroxane with indolyl-3-acetic acid produces a synergistic increase in the growth of coleoptiles in maize.

The terms "plant" and "plant growth" relate to dormant and actively growing plants, as well as to roots, tubers, bulbs, seeds, cuttings, etc., ie to plants in the same stage of development and each size ₀

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Claims (3)

~ 22 godfather η tansprilciti 1., Plant growth medium, gekenaaeieb.net by a content of pbenylfuroxane. 2. Vegetable ingredients according to claim 1 »characterized by a content of O, OOO5 to 95 Phenylfuroxane and an inert milling material, 3. Plant growth agent according to claim 1, characterized by a content of 0.0005 to 95 phenylfuroxane _f an inert liquid $ Sräger © toff and a wetting agent, 4-. Plant growth agent according to claim 3 to 5 * characterized by an additive content of a natural or synthetic auxin, antiauiin _5, one or more Giberellinen or Kininea, 109847/1921