DD140966A1 - MEANS FOR REGULATING PLANT GROWTH - Google Patents

Abstract

The agents affect metabolic and growth processes in Plants and parts of plants. To reduce the defects, the known Solutions to achieve such effects have become agents developed, which increase and stabilize crop yields possess broad spectrum of action. They are marked by a content of substituted imidazolecarboxylic acid anilides of general formula I. In this formula, R-j, R2, R3, R4 is hydrogen, hydroxy, alkyl, aralkyl and optionally substituted aryl; Ar is optionally substituted aryl and for n 0 or 1. The funds reduce the tendency to grain in grain and affect the flowering and fruiting of cucumbers and tomatoes. - Formula -

Description

The invention relates to novel agents for regulating metabolic and growth processes in plants and parts of plants.

Characteristic of the known technical solutions

Due to the current state of the art, it is possible to specifically intervene in the plant processes, as confirmed by the application of already known artificial substances such as chloroquat, etephone, succinic acid dimethyl hydrazide and maleic hydrazide. "

Artificial regulators of plant metabolism and growth can attack at the most diverse receptors and in

Depending on the stage of development of the seed of the plant and the plant parts, the type of application, the Anwendungszeitpuxikt of the concentration and the formulation of the active ingredient trigger different reactions »This results in a variety of applications ·

In this way, the processes of germination can be targeted, promoted or inhibited. "In addition to general morphological changes in plants, length and thickness growth can also be controlled. Furthermore, the vegetative and generative bud formation, the flowering process, to influence the sexual detenation and to achieve parthenocarp effects,

In addition, processes of fruit formation, fruit ripeness, fruit and leaf fall, and senescence and yield alternation must be regulated.

For example, it has already been proposed in GB Patent 1352 100 to use "2-imidazolylcarbonylbenzoic acids to regulate plant growth." The compounds described there are relatively difficult to access and have only a limited range of action, the patent specification contains only detailed information on the use of these compounds on the inhibition of grain length growth and defoliation. The scope is therefore very limited.

The known plant growth regulators have, in part, economic shortcomings, which are due to high application rates, expensive raw materials or limited scope, or do not meet toxicological requirements due to residues and consequent delays,

Object of the invention

The aim of the invention is the rationalization of crop production, in particular the increase and stabilization of crop yields, by providing such agents for regulating metabolic and growth processes in plants and plant parts which have a broad spectrum of activity and their economy, toxicology and other properties Deficiency of the known remedies diminish ^

Explanation of the essence of the invention 'Technical problem

It is an object of the invention to provide, by further modification of the imidazole structure, new active agents for plant growth regulators which can find as broad a practical application as possible.

Features of the invention

It was found that imidasclcarbonsäureanilide the general formula

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in which η is O or 1 and in which for β hydrogen, hydroxyl, alkyl, aralkyl and optionally substituted aryl for Ep hydrogen, hydroxyl, alkyl and optionally substituted aryl, for R-methyl, benzyl and optionally substituted aryl, for R ^ _ Hydrogen and alkyl and Ar may be optionally substituted aryl, are suitable for the regulation of metabolic and growth processes in plants and parts of plants.

As an example of imidazolecarboxanilides which can be used according to the invention, the compounds compiled in Table 1 can be prepared by methods known in principle (Journal of Chemistry J (1970), 211} Liebigs Annalen der Chemie 1974, 1399? DT-OS 2324893! Chemical Abstracts 8 ^ 1641742), namely

** N (3) -oxides of hydroxyimidazole-2-carboxylic acid anilides (N-I-30) from C-hydroximinoketones (<< - diketone-monoximes) and the oximes of glyoxylic acid anilides

- N (3) -oxides of 1-hydroxy-4 (5) -ethyl-ethylazazole-5 (4) -carboxylic acid anilides (Nos. 3 to 59) of bis-hydroximinoacetoacetanilides and aldoximes

* »1-Hydroxy-4-methyl-imidazole-5-carboxylic acid anilides (Nos. 60-81) from α-hydroximinoacetoacetanilides, aldehydes and ammonium acetate

** N (3) oxides of 1-alkyl (aryl) -2-aryl-4-methylimidazole-5-carboxylic acid anilides (Nos. 82-106) from α-hydroxyiminoacetoacetanilides, alkyl (aryl) amines and aldehydes ( except formaldehyde)

(Nos. 107-128) are α-hydroxirainoacetoacetanilides, alkyl (aryl) amines and formaldehyde

Imidazole-2-carboxylic anilides (Kr.129-136), imidazo1-4 (5) -carboxylic anilides (He 137-142) and 1-alkyl (aryl) -imidazole 4-carboxylic anilides (# 143-153) from the above N-oxides or 1-hydroxy compounds by reduction.

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The preparation of the individual connection types is illustrated by the following embodiments 1-7,

The agents of the invention are useful for regulating metabolic and growth processes in plants and plant parts according to the various requirements of the practice. reversible and provide a valuable enrichment of the art. Depending on their application, the erfindungsgeiaäßen means in the form of solutions, emulsions, suspensions, powders, pastes, dusts and scattering agents or optionally granules are present. These formulations are prepared in a known manner »

The agents according to the invention trigger different physiological reactions in the plant organism depending on the concentration, the time of application, the sequence of application and the development of the different plant species.

Thus, the agents of the invention can induce sproßverkürzende and stabilizing effects. This allows, inter alia, an application of these funds to reduce the tendency of crops in cereals «Furthermore, they are suitable for sexual rooting in cucumbers and increase the fruit set in tomatoes, resulting in an increased yield performance. In addition, the agents according to the invention bring about a limitation of the formation of stinging impurities in tobacco and Toeiate and a blooming influence and upset in asters.

The gowns according to the invention are preferably applied in active substance concentrations of 10 to 10% by weight. They can be combined with one another and / or used in combination with other agents for biological process control and in conjunction with plant protection and pest control agents and other agrochemicals.

The following examples are intended to illustrate the compound without limiting it. The names of the substances are given in Table 1.

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embodiments

The following examples illustrate the invention without restricting it »

Example 1; 101.1 g of diacetylmonoxime and 164.2 g of isonitrosoacetanilide in 1 l of methanol are refluxed to the nearest solution, and then with vigorous cooling with ice-water for 3 hours, a vigorous stream of hydrogen chloride is introduced. The reaction mixture is left overnight and is subsequently evaporated in a rotary evaporator. To the solid residue is added 1 1 of water, stirred well and the pIMiert with dilute * NaOH to 5 to 6 a. Then it is sucked off, washed thoroughly with water and dried on clay. The dry product is again stirred with 500 ml of cold acetone ^ sucked off again and dried. This gives 190.6 g (77 $ 0 slightly brownish 1-hydroxy - ^ - _t 5 ^l -diinethyliinidazol ~ 2-carbon-Eäureanilid ~ N (3) oxide of melting point 217-219 ° C. Recrystallised from glacial acetic acid with the addition of water, it melts at 222-224 ° C. (No. 1, Table 1)

Example 2: The solution of 10.3 g-isonitrosoacetoacetanilide and 7.15 g of octanaloxin in 100 ml of methanol is saturated with dry HCl while cooling and allowed to stand over Kacht »Then the solvent is removed in a rotary evaporator. The residue is dissolved in 100 ml of 2 N NaOH, the solution is stirred for 15 minutes with 5 g of activated charcoal, filtered and dripped to the filtrate with stirring and cooling to pH Uert 5-6 half-concentrated hydrochloric acid »Then it is filtered off with suction, washed with water and drying on Toris Recrystallization from toluene gives 8.5 g (51 $) of 1-hydroxy-2-n-heptyl-4 (5) -methylimidazole-5 (4 -) -carboxylic acid anilide-N (3) -oxide Shape of brownish leaflets} Melting point 157 ° CV (No. 33j Table 1)

-6- 210 2

Example 3? The solution of 10.3 g of isonitrosoacetoacetanilide, 5 g of benzaldehyde and 15 g of ammonium acetate in 100% glacial acetic acid is refluxed for 3 hours. After cooling, the reaction mixture is stirred slowly into a solution of 50 S sodium acetate in 400 ml Water. The precipitated product is filtered off, washed with water, dried and recrystallized from dilute DMF. This gives 8.0 g (pi <fy 1-hydroxy-2-phenyl-4-methylimidazole-5-carboxylic acid anilide in the form of colorless needles, mp 265-268 ° C. (No. 6iy Table 1)

Example Al 10.3 g of isohitroseacetoacetanilide, 5t3 of benzaldehyde and 5j of 35% of benzylamine are dissolved in 100 ml of glacial acetic acid and the solution is refluxed for 3-4 hours. The cooled reaction solution is then added dropwise in 3OO ml of semi-concentrated aqueous ammonia. It is suctioned off, washed thoroughly with water and dried on clay. Yield of crude 1-benzyl-2-phenyl-5 & ethylimidazole-4-carboxylic acid anilide N (3) oxide 18.15 g (95 $) ' Colorless flakes of toluene; Melting point 211-212 ° C. (No. 85, Table 1)

Example 5 Dissolve 10.3 g of isonitrosoacetoacetanilide, 3t? g n-butylamine and 10 ml of formalin in 100 ml of alcohol, heated under reflux for 2 hours and then concentrated in a rotary evaporator. When the residue is treated with ether, crystallization takes place. This gives 7.65 g (55 S) of 1-n-butyl-5-methylimidazol-2-one-4-carboxylic acid anilide, which crystallized from dilute alcohol in the form of colorless leaves; Melting point I56-158 ° CV (No. 108, table 1)

Example 6i The solution of 10.3 S oC-isonitrosoacetoacetanilide, '6 »15 g of p-anisidine and 10 ml of formalin in 100 ml of glacial acetic acid is refluxed for 2 hours, then concentrated a little and then added dropwise with stirring and cooling in 3OO ml semi-concentrated ammonia. It is filtered off with suction, washed with water and dried on clay. Yield of crude ip ^ methoxyphenyl ^^ c zol ~ 2-one ~ 4 ~ carboxylic acid anilide 13.4 g (83%) of dilute Aiko colorless needles and leaflets; Melting point 230-231 ° C »(No. 111, Table 1)"

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Example: 10 g of zinc dust are added in portions to the boiling solution of 17.5 g of in-4-anilinocarbonyl-5-methyliimidazole-N (3) oxide (Kr. 81) in 100 ml of glacial acetic acid. After heating for 6 hours under reflux and allowed to stand the cooled reaction mixture overnight. It is then filtered and the filtrate is added dropwise slowly with stirring in 400 ml 15 fAge M solution. The crude imidazole is filtered off with suction, washed with water, dried and crystallized from dilute alcohol. This gives 12.0 g (? 2 ^) of 1-n-butyl-2-phenyl-5-methylimidazole, 4-carboxylic acid anilide in Fora colorless leaves; Melting point 112 113 * 5 ° C (No. 144, Table 1).

Example 8: Cotyledon test

From pregerminated radish seeds cotyledons are removed and the fresh weight of 10 pieces each bestiraat. Subsequently, the Kotelydonen remain for several days in test solution (concentrations 10 10, 10 percent by weight) under continuous light before he, neute fresh weight determination takes place. The differences between the initial and final weight are determined. "The values obtained are related to those of the water control and the kinetin (10 *" ^% by weight). The results printed as equivalent values are calculated as follows.

Cotyledon weight in test solution - cotyledonous wt, in aquadest cotyledonous weight in kinetin solution - cotyledon gels. in Aquadest

If the equivalent value is 1, the tested substance corresponds in its effect to kinetin; If the value is 0, the substance is ineffective. (Table 2)

Example 9 * White Coleoptile Cylinder Test Coleoptile leaves separated from wheat germinating rings are mixed with the agents of the invention of different concentrations

• "1 -6 '"' r>

(10 to 10 GeV.-SS active substance) for about 20 hours at 25 C incubated. At the end of the experiment the longitudinal growth of the individual coleoptile plants is determined. The values thus obtained

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are related to those of control and standard (indolylbutyric acid IBS)

X-K A'quival devalued =,. _,

X s value of the test substance

K.i Belativwert der Wasserkontrolle A = Eelativwert of the IBS standard

Negative X equivalent values indicate that the tested substance inhibited the stretch growth (Table 3).

Example "1Oi Stalk stabilization and tillering at

Grain

The test plants are summer wheat (Triticum aestivum) variety Ramses', "summer rye (Seeale cereale) variety Petka and spring barley (Hordeum vulgare) variety Elgina" The sowing of the mentioned cereals occurs in 5 cm - Neuca pots with soil · The preparations become in two Applied to different plant stages »Seed treatment (S): 24-hour swelling of the seeds in the test solution.

4-leaf stage treatment (C): Spraying seeds at 600 l / ha. In pickling, application was also made in the seedling (A), 2-leaf (B) and A-leaf (C) stages. Ten plants are used per concentration and application. The concentration levels were 10 °, 10 ** and 10% by weight of active substance. "" The evaluation takes place in the flowering stage. Half-length, Halradickey total green mass and number of halves per plant are determined as measured values and the values are converted to the uA-treated control (s 100 fS) . CCC and Ethrel serve as reference substances ". The results are summarized in Tables 5 and 5

Example 11: Halmstabilisierung in cereals (tube test) are used as test plant spring wheat seedlings of the "Hatri" and summer barley variety "Trurapf" ^r The cultivation of the plants takes place in test tubes with an appropriate nutrient solution. ^"1

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After 14 days (2-leaf stage) the preparations are applied by dipping the individual plants.

Per concentration and application .10 plants are used,

The concentration levels are 10 and 10 percent by weight of active substance. The measured values are determined as the length of the pseudo-protozoa between 1 and 2, the leaf blade and the fresh mass of the plants, and the values are calculated on the untreated control (= 100 ° C. The results are summarized in Table 6,

Example I2i Blooming inhibition, compression and Geiztriebhemmung in tobacco To determine the bloom inhibition and growth inhibition tobacco plants of the variety "Canella" (Nicotians tabaeum var »undulata) in the sosette stage (2-4 leaf stage) siit with an application rate of 600 l / ha in the concentrations of 10, 10 and 10 weight percent, active substance treated. The further cultivation takes place in the greenhouse at ca, 22 C, the evaluation takes place, if all plants bloom. The number of flowers and the height of the plant are determined in relation to the control,. , To determine the Geiztriebhemnung the plants are applied at the beginning of flowering after removing the inflorescences by dropping the preparation solution in the leaf axes. The evaluation is carried out as the lateral drive length of the control is 10 - 15 era. The number of side shoots is determined in relation to the control (Table 7).

Example 13? Sexdetermination und.Stauchung with cucumber. Iia Greenhouse cultivated cucumber plants of the varieties "Trix", and "Vorgebirgstraube" (Cucunis sativus) are sprayed pot-wet in 2 "to 4 * leaf stage with the test solution. Number of female flowers (fruit shoots) and plant length are determined in relation to the control (Table 8).

Example 14ϊ Flowering infestation and compression.with asters

Potted Astsrpflanzen (Callistephus sinensis L.), the sort "Karmesin" are sprayed with a stature height of 5 - 7 cm with 6OO l / ha. The concentrations of the test solutions are 10 °, 10 and 10 percent by weight of active substance _e

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Cultivation takes place under greenhouse conditions or in the foil "skin" 8 weeks after the treatment, the growth and the side shoot count are determined in relation to the control (Table 9)

Example 15 · Influencing the fruit set and the plow drive *

inhibition of tomatoes. *

For the determination, tomato plants (Lycopersicon esculentum) of the variety "Harzfeuer" or "Grit" are treated with a preparation solution in the concentrations 10 °, 10, 10, 10 ** ^ usd 10, if at the first bloom state etv / a 2 flowers are open. The further cultivation takes place in the greenhouse, foil tent and in the summer in the field. After 9 weeks, the evaluation is carried out by counting and weighing the fruit in relation to the control, The evaluation of the Geiztriebheramung takes place 4 to 9 weeks after the application by counting the Goiztriebe (Table 10);

', in which η is O or 1;

R is hydrogen, hydroxy, alkyl, aralkyl and optionally substituted aryl;

Rp is hydrogen, hydroxy, alkyl and optionally substituted aryl;

R 'is methyl, benzyl and optionally substituted aryl; R. for hydrogen and alkyl

and Ar is unsubstituted or substituted aryl in a mixture of customary carriers, fillers and auxiliaries or solvents

2 "Plant growth regulating agent according to item 1, characterized in that it is used to prevent crop tilting in cereals

3 'Plant growth regulating agent according to point 1, characterized in that it is used to influence flowering and fruiting' ''

Kierzu ".l3 ropes tables

Table 1

CONA ^

CO) -N

VerbiHduags ** ^R 1 ^R 2 ·? 3 VCH R ₃ H Ar StellgW * - a Synth> Melting - "* Out NRV VCH ₃ H H CONR ₄ Ar according to puakt prey VCH H example <° c) <$) 1 OH VCH 5-CH. , US US " ^C 6 ^H ₅ 2 1 1 222-24 77 2 3 OH OH VCH ₃ VCH VJI VJI US US > J VJ V H 3-CH ₃ C ₆ H ₄ VCH ₃ C ₆ H ₄ ro ro 1 1 1 1 I85-8? 248-51 69 82 4 , OH VCH ₃ 5-CH ₃ H 2-ClCgH ₄ 2 1 1 2OI-O3 63 5 6 7 > OH OH OH VCH ₃ VCH ₃ 5-CH ₃ 5 -CH ₃ 5-CH ₃ H 3-ClCgH ₄ VClC ₆ H ₄ , VBrCgH ₄ CVl CJ CVl 1 1 1 1 1 1 186-88 24V46 253-54 66 75 71 8th OK VCH ₃ 5-CH ₃ H VCH ₃ OC ₆ H ₄ 2 1 1 217-19 81 9 OH VCH ₃ 5-CH ₃ H 3-CF ₃ C ₆ H ₄ 2 1 1 193-96 80 * | 10 OH VCH 5-CH ₃ H 2, VCl ₂ C ₆ H ₃ 2 1 1 221-23 75 11 OH VCH 5-CH ₃ H . 2,5-Cl ₂ C ₆ H ₃ 2 1 1 233-35 77 12 OH VCH 5-CH ₃ H 2-CH ₃ -VClC ₆ H ₃ 2 1 1 238-40 80 years 13 OH 5-CH ₃ H · 3-Cl ~ VCH, CGH 2 1 1 23Ο-32 ^: ' 76 14 OH 4-CH ₃ 5-CH ₂ C ₆ H ₅ H ^C 6 ^H 5 2 1 1 220-21 85 '15 , OH. VCH 5-CH ₂ CgH ₅ H 2-ClC ₆ H ₄ 2 1 ^V 1 180-82 51 16 OH VCH 5-CH ₂ CgH ₅ H VClCgH ₄ 2 1 i 200-02 79 17 OH 5-CH ₂ C ₆ H ₅ H VBrC ₆ H ₄ 2 1 1 21V1? 84 18 OH 5-CGH ^C 6 ^H 5 2 1 1 193-96 68 19 · · OH 5-CGH 2 1 1 212-15 77 20 OH 5-CgH ₁ - 2-CICaHa 2 1 1 178-80 45

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210 212 - * -

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Table 3, sheet 2

210 212

substance

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Bestockuagsförderuag with cereals number shoots {% to K)

substance weight / A W o B i ζ β r. S C, G β T S t ® , R- 0 g g β a - "* .92 Ser. No. It. volume ^ C- S C S C Tab, 1 100 130 o (t) o (t) , 92 , 1 .. 10 ° 120 100 '100 oct) 140 100 83 5 χ ίο "" ¹ 100 100 - 100   100 " ΙΟ "" ¹ 100 120 100 109 100 115 5 χ 1O ~ ² 110 100 ' 100 100. 10 ~ ² ' 100 100 100 127 130 108 5 χ 10 ~ ³ ι

D = Haladick © C% to K) L = Halmläag © ^{! T} M = Green Mass "

Table 5. Page

Stalk stabilization at Gotreid ·

Substaaz weight / D A M W e i ζ e η M D C M D S M D C L M Ser. No. lfci, · Volumea-% 84 L B 71 89 L 101 0 L 0 (t) 0 0 o (t) Tab. 1 4 10 ° 79 D L 77 96 0 111 92 82 92 1 5 χ 1O ~ ¹ 88 91 89 77 96 100 100 99 80 122 88 100 99 10 ~ ¹ 94 102 91 88 116 100 95 109 5 χ ίο " ² 103 100 98 102 85 145 191 110 80 142 1o4 94 107 10 * " ² 10? 109 102 114 90 97 91 120 5 χ 10 * " ³ 89 96 102 '

D ». Haladicke L a Halmiang M ». Grüamasse

to K)

Table 5 »page 2

' S G 6 Ϊ M S t i D O C M D S R oo g © a 94 C M weight / D L o (t) 94 L 105 90 L 91 L 99 Volume-% 0 0 107 10? 98 144 107 93 M [D 94 105 85 10 ° 97 99 116 98 113 110 10? 95 35 95 99 10 ~ ¹ ' 119 96 96 106 102 103 ΙΟ " ² 104

D = blade thickness (.% To K) L = blade placement ♦♦ M = green pocket © ^M

-36-

210 212

Table 6

Halm stabilization in cereals (Röhrßtest) (  · % for control) Dimensions barley Mass (% to K) wheat 100 103 growth 104 100 Verbiadungs- weight / growth 103 97 120 105 88 100 Number Lf d ^ Nrν It. Tabi 1 Volume-% 103 93 83 100 105 110 112 108 60 10 ° ΙΟ * ¹ 10? 97 95 95 125 110 94 94 61 10 ° 90 100 104 104 105 95 107 10 ° ΙΟ " ¹ 97 112 100 93 110 10 ° "- ¹ . 100 114 64 (tox 93 11? 10 ° 81 100 34 10 ° 81 86 40 10 ° 10 "" ¹

Table 7

Blühheia munfl « upset and stinging inhibition in tobacco {% for control)

connection weight / α 10 ° number of flowers plant height Seiteiatrieb * - number volume ^ 10 ** ¹ number (% to K) Ser. No. 10 ^c It. Tab. 1 10 ° 1 ΙΟ " ¹ , 0 (t) 0 (t) 10 ~ ² 80 90 10 ° 100 90 60 -o- ¹ 40 44 64 -o- ² 70 113 64 10 ° 80 123 75 61 ΙΟ " ¹ 100 118 60 10 " ² 100 132 64 10 ° 90 113 79 108 1O- ^1: 80 91 49 ΙΟ "* ² 90 121 102 10 ° 70 97 72 34 ΙΟ "' ¹ 111/100 80 10 * " ² 111/50 54 111/100 63 40 111 111 111

210 212

Table 8 SexdetermJBatioH and Stauchuag with cucumber

substance ". D 60 weight / 1 10 ° (% to 2> 0 Kojatrolle) Ser. Nrν Voluiaea-jS 10 * " ¹ Fruchtaasatz 77 ItY Tab ΙΟ " ² 62 1 61 Variety "Trix" 10 ° 147 -o- ¹ 132 107 ΙΟ " ² 2) variety 'Planting length 10 ° 100 "ο " ¹ 100 ¹ > - ² ^ 18 108 ΙΟ " ² . 67 112 101 10 ° 167 112 96 "ο " ¹ 100 '• Vorgebirgstraube " 110 ΙΟ- ² 100 10 ° 133 ΙΟ " ¹ 100 117 ΙΟ " ² 67 10 ° 100 10 "* ¹ 100 34 ΙΟ " ² .100 10 ° 147 ₁₀ -1 221 40 ΙΟ " ² 132 10 ° 140 10 "* ¹ 125 MO ** ² 125 10 ° 167 133 100 * 55 80 128 114 105 98 108 105 81 82 90 100 87 102 112 128 95 114 106 106 92 99 91 92 91

Table 9 Flow influence and compression at Astera

substance weight / (Jo for control) 'Planting & cages Runner · * Ser. NRV Voluraoß-% Blühbegina number It. Tab, 1 • - 92 76 1 10 ° 102. 100 95 10 ~ ¹ 99 136 162 10 ~ ² 95 100 90 89 86 * 60 10 ° 10 " ¹ 81 I 74 ... 124 142. - '? ΙΟ " ² 75 93 131 107 10 ° 75 92 114 117 ίο- ¹ 1O ** ² 76 80 -89 122 108 io ° · 76 106 131 10 " ¹ . 84 99 117 ΙΟ- ² 77 97 .107 110 ' 10 ° 101 90 97 10 ^ ¹ 99 10? 129 ΙΟ " ² 9? 108 90 117 10 ° 89 120 117 ₁₀ -1 , 104- 118 138 ΙΟ " ² 94 115 152 34 '10 ° 109 93 11? 10 "* ¹ 108 101 128 ΙΟ- ² 102 103 124 AO 10 ° 101 ·. 94 86 105 121 I38 10 " ² 102

212

Table 10

Effects of fruit set and Geiztriebhemmuag with tomato

substance weight / - 10 ° ¹ ^ Ha 10 ° (% to the komtrolla) - 2) ₅₉ mass 84 Seiteatriebzahl I • / Lfd * NrI Voluiaea- $ S ΙΟ ' ¹ 1O * " ¹ fruit set 90/85 113 It, Tab. 1 • ίο * ² 10 " ² 103/90 95 119 1 10 "* ^{3 10} ~ ^{3 1)} 92/97 114 / 11Σ 109 114 ΙΟ " ⁴ 10 ° 108/93 32 107 10 * " ¹ 107/99 C 54 ΙΟ * "* ² 114 60 10 " ³ 112 rit 97 10 ° rzfeuer 50 117 1O " ¹ 137 115 • ITO 10. 116 113 10 " ³ 109 113 78 34 43 66 62 9 1 40 45 106 86 112

Claims (1)

Claim of invention. ,. , 1, plant growth regulating agent, characterized by a content of Iiaidazolcarbonsäureaniliden the formula ' ⁴ .CONAr (O) -N