DE2356368A1 - N,N-di-substd. amide plant growth regulators - contg. N,N-di-(4-hydroxy-3-,6-dioxo-hexahydropyrazin-4-yl-acetyl)-amide gp(s) - Google Patents

Abstract

Organic cpds. contg. the gp. of formula (I) (i.e. N,N-di- 4-hydroxy-3,6-dioxo-hexahydro-pyridazin-4-yl-acetyl -amid- e, referred to subsequently ad N,N-di-Q-amide) of its tautomers are new The cpds. (II) are plant-growth accelerators effective with monocotyl and dicotyl plants, which can be used for stunting the growth of grasses, with ornamental plants, for increasing the vegetation time of vegetables and with hedges and bushes. They have high solubility in water and can be applied as conc. aq. solns. Stunting effect is rapid, and the cpds. persist for a long time in open ground.

Description

prov. no. 7334 NA

CF. Spieß & Sohn Frankfurt / M., November 9, 1973

6719 Kleinkarlbach DrOz / MSchu.

and .

North German Affinerie 2000 Hamburg

N, N-Di _r / 4-hydroxy-3, 6-dioxohexanydro-pyridazinyl- (4) -acetyi / -

amide

The invention relates to N, N-di- / ^ - hydroxy-S, 6-dioxohexahydropyrida zinyl- (4) -acetyl / - amides, these are compounds with the group

Process for the preparation of these compounds as / ie application these compounds to regulate plant growth.

In DT-OS 1 542 989 and DT-OS 2 132 466 are means for Influence on plant growth described the specific

50 9 820/1089 \ - ² "

Derivatives of the 4-Ifydroxy-3, 6-dioxohexahydro-pyridazinyl- (4) -acetyl amide represent. Although these compounds have good effects, they have the disadvantage that they are in the form of solutions experience decomposition when standing in the air and in light and thus their full effect only lasts for a comparatively short time.

It has now been found that in particular a much longer lasting full effect in the control of plant growth can be achieved if the fiction, contemporary new organic chemical Connections come into use.

With the present invention, therefore, organic-chemical Links suggested that the grouping

CO

exhibit. Due to the possibility of enolization of the two 3, 6-dioxo-hexahydro-pyridazinyl radicals, the compound can also be used in exist in the corresponding various tautomeric forms.

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In these compounds the free valence of nitrogen can be reduced by the various organic as well as inorganic residues, occupied be. · "" - "" "..

Particularly suitable connection groups and individuals falling under them are (for the individual concrete connections, for the sake of simplicity the 4-hydroxy-3,6-dioxohexahydro-pyridazinyl- (4) -acetyl radical is denoted by Q):

Compounds in which the free valence is caused by hydrogen, the cyano or the hydroxyl group is occupied;

Compounds in which the free valence is occupied by an amino group is;

This group includes the compounds with the designation N, N-Di- (Q) -N \ N'-dimemyl-hydrazide and N, N, N ', N'-tetra- (Q) -hydrazide.

Compounds in which the free valence is replaced by a straight or branched chain alkyl radical with 1 to 16 carbon atoms, preferably 4 to 7 C atoms, is occupied;

This is z. B. to the compounds with the designation N, N-di- (Q) -pentylamide; N, N-di- (Q) -butylamide; N, N-di (Q) isopentylamide; N, N-di (Q) hexylamide; N, N-di (Q) octylamide; .N ₁ N-di- (Q) -dodecylamide; N, N-di- (Q) _2 / -oxo-propionic acid ethyl ester-S'-amide; N ^ iN'-tri-iQJ-ethylenediamide; N, N, N ', N'-tetra (Q) ethylenediamide; Ν, Ν, Ν ', N / -Tetra- (Q) -hexamethylene diamide; Ν, Ν, Ν ', N "tetra- (Q) -dipropylenetriamide; Ν, Ν, Ν', N", N '* -penta- (Q) -dipropylenetriamide.

Compounds in which the free valence is replaced by an alicyclic Remainder is occupied;

'■. . . ■■■ '- ■■' - 4 -

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This is z. B. to the connections with the designation N, N-di- (Q) -cyclohexylamide; N, N-di- (Q) -cyclohexanone-2'-methylene amide.

Compounds in which the free valence is occupied by an aromatic ring or an aromatic ring system; This is z. B. to the compounds with the designation N, N-Di- (Q) -anilide and N, N-Di- (Q) -2'-carboxy-anilide.

Compounds in which the free valence is occupied by an aralkyl radical is;

This is e.g. the connection with the name N, N-di- (Q) -benzylamide.

Compounds in which the N, N-di- (Q) -amid group is the amino group replaced one amino acid;

These are, for example, the connections with the designation N, N-di- (Q) -glycine; N, N-Di- (Q) -D, L-alanine; Di- (Q) -L (+) - arginine; Tetra- (Q) -L (+) - arginine; Hexa- (Q) -L (+) - arginine; N, N-Di- (Q) -L-tyrosine; N, N-Di- (Q) -DL-ethionine.

Compounds in which the N, N-di- (Q) -amide grouping is the amido group replaced by an acid amide or thio acid amide; These are, for example, the connections with the designation Ν, Ν, Ν ', N'-tetra- (Q) -ureide; N, N-Di- (Q) -N ', N'-dimethyl ureide; N, N-di (Q) phenylureide; Ν, Ν, Ν'-tri- (Q) -phenylureid; N, N'-Di- (Q) -nitros o-methyl ureide; Ν, Ν, Ν ', N'-tetra- (Q) -thioureid; N, N'-di- (Q) -trimethylene-thioureid; Tetra (Q) biuret; Penta (Q) biuret; Penta (Q) guanidide; N, N-di (Q) malonyl guanidide; Tetra (Q) biguanide; Hepta- (Q) -biguanide

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- 5 -.- ■■. ■: - ■ -

Compounds in which the free valence is replaced by an AcyLrest of a organic acid is replaced;

These are, for example, the connections with the designation N, N-di (Q) acetamide; N, N-di- (Q) -carbamic acid ethyl ester; N, N, N-tri- (Q) -amide.

Hydrogen atoms on the carbon, nitrogen or oxygen of the substituent can in turn be substituted again. About that In addition, connections can also be obtained that support the grouping

--At the

contained two or more times in the molecule. You can do connections obtained with asymmetrical or symmetrical formula. In the latter case, a general formula can apply:

■ .- ■ - 6 -

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fr / ⁰ ^

if Z ⁷ /

/ ^c ~ ^c

»■■ ^c -

c * »

Again, there are numerous substitution options. For example, the radical R can be formed by the following groups

be educated:

- (CH ₀ ) -, in which "n" is an integer from 1 to 16, Δ η

an aromatic group such as a phenylene group or

-CO-, -CS-, -C-, -CONR ₄ -CO-, -C-NR ₄ -C ₁ -, -CO-CO-, f} R ₄ ⁴ KR ₄ N «| ·

where in the case of several radicals R these can be identical or different and hydrogen or a 4-hydroxy-3, 6-dioxohexahydro-pyridazinyl- (4) -acetyl radical mean.

Due to the possibility of enolization of the 3,6-dioxohexahydro ~ pyri = The substances still have an acidic character and can be used as dazinyl residues form salts with weak bases. Strong bases make the amide ' group split.

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The salts, too, insofar as they can be prepared, have growth-influencing properties and can be used for the same purposes as the N, N-di- / 4-hydroxy-3,6-dioxohexahyäro-pyridazinyl- (4) -acetyl J-amide itself.

The process forming part of the invention for the preparation of the Compounds happens in such a way that an amine or an amide, the another two "hydrogen atoms on nitrogen has two moles of 4-Hydro = xy-3,6-dioxo-hexahydro-pyridäzinyi- (4) acetic acid or else a 4-Hydroxy-3, 6-dioxorrhexahydro-pyridazmyl- (4) -acetic acid amide, the still carries a hydrogen atom on the amide nitrogen atom, with one mole 4-Hydroxy-3,6-dioxo-hexahydro-pyridazinyl- (4) -acetic acid each is reacted by heating in an aqueous medium.

Compounds with two or three identical acyl radicals on a nitrogen atom are known in individual cases. Their production is only through complex and detour procedures possible. It must therefore be surprising that the preparation of the compounds according to the invention is possible by simply boiling in an aqueous medium, i.e. that under the same reaction conditions under which a molecule of 4-hydroxy-3,6-dioxohexahydro-pyridazinyl- (4I-acetic acid) was obtained with an amine or ajnide reacts a second and - if one of ammonia goes out - even a third molecule of 4-hydroxy-3, Ö-dioxohexahydro-pyridazinyl- (4) -acetic acid can be made to react. This is undoubtedly one for the 4-hydroxy-3, 6-dioxo = hexahydro-pyridazinyl- (4) -acetic acid peculiar chemical reaction.

To prepare the compounds according to the invention, the known amides of 4-hydroxy-3,6-dioxo-hexahydro-pyridazinyl-, - (4) -acetic acid even further with 4-hydroxy-3,6-dioxohexahydro-pyridazinyl- (4) -acetic acid implement, provided the nitrogen atom of the amide group

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another hydrogen atom carries. In this further implementation will then this hydrogen atom is also replaced by the 4-hydroxy- -3,6-dioxo-hexahydro-pyridazinyl- (4) -acetyl radical and compounds are obtained in which the nitrogen atom is two 4-hydroxy-3,6-dio>: o-hexahydro-pyridazinyl- - (4) -acetyl radicals.

If one goes in the simplest case from the 4-hydroxy — 3,6— dioxo-hexahydro-pyridazinyl ~ (4) -acetic acid amide itself

off, the two hydrogen atoms still present on the amide nitrogen atom can be combined into one Reaction or in succession through the 4-hydroxy-3,6-dioxo-hexahydro-pyridazinyl- (4) -acetyl radical replace, whereby in this special case a compound is obtained which has three 4-kydroxy-3,6-d5.oxo-hexahydro-pyridazinyl ~ (4) -acetyl radicals.

The N, N-di-J4-hydroxy-3,6-dioxo-hexahydro-pyridazinyl- (4) -acetyl-amides can be quite generally produce on the way that one ^ an amine or an amide, the on the nitrogen atom still carries two hydrogen atoms 2v; one mole of 4-hydroxy-3,6-dioxo-hexahydro-pyridazinyl- (4) acetic acid reacted by heating in an aqueous medium.

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Since the 4-hydroxy-3,6-dioxoh.exahydro-pyriäazinyl- (4) acetic acid by boiling citric acid with hydrazine hydrate. 'Can be produced in an aqueous medium is therefore also the Possibility given by adding in the same vessel the appropriate amount of an amine and further boiling the corresponding N, N-Di-J4-hydroxy-3,6-aioxöhexahydro- -pyridazinyl- (4) -acetyl 7-amide.

If there are two primary amine groups or two amide groups in a molecule, each of them can with two molecules of 4-hydroxy-3,6-dioxohexahydro- -pyridazinyl- (4) -acetic acid react and the corresponding N, N-di- [4-hydroxy-3,6-dioxohexahydro-pyridazinyl- (4) -acetyl] - -amides form.

The compounds of the invention are useful as growth regulators best for. They surpass those in DT-OS 1 542 989 and compounds described in DT-OS 2 132 466 are still gaining strength and reliability, especially when used outdoors an advantage is. The percentage of growth inhibition is behind four weeks generally very high. This occurs as a side effect sometimes observed, undesirable brown discoloration, e.g. in grass, only rarely and to a lesser extent.

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In the substances according to the invention, the strength is the Effect and duration of effect depend on the concentration and the time of application. In general inhibit the substances in a wide range of application concentrations the growth of the plants, so that those treated with the compounds according to the invention Plants show a smaller growth. After a certain time, which is longer, the greater the amount of W5.rksubstanz the plants will grow normally again. Only with a relatively high application concentration ■ Tration, slight damage can also occur, which, however, grows together again later.

The substances according to the invention have the advantage that when used to inhibit grasses or plants die.Hemmung sets in exceptionally quickly and in

Depending on the amount used, it also lasts longer outdoors than with the substances listed in DT-OS 2 132 466.

The substances according to the invention can be used to regulate growth in both monocotyledonous and also use on dicotyledonous plants. The good effect on dicotyledon plants is noticeable.

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The substances according to the invention can be based on their properties Use it to keep grass low in order to save mowing as well as in the cultivation of ornamental plants and vegetables to extend the growing season. In addition, the Substances, depending on concentration and time of application, have an additional Be-r for many plants treated with them Congestion (rooting) and branching. Another possible application consists, for example, of keeping hedges and bushes short along the streets in order to save on the hassle of cutting.

It should be emphasized that some of the substances according to the invention have a considerably good solubility own in water. This enables them to produce highly concentrated, aqueous solutions to produce the substances required for the application particularly with regard to leaf uptake and transport in the plant, appear particularly favorable. The substances are quickly removed from both plants . taken up via the leaves and also through the roots and then in the plants both acropetal and basipetal onward transport! location.

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The use of the compounds according to the invention for The purpose of influencing the growth of the plants is preferably done by treating them Plants with an aqueous solution of the substances. The plants can be sprayed with such an aqueous solution, can be sprayed or poured.

The compounds can also be in emulsion or suspension, as well as in a mixture with pulverulent, inert, solid carriers such as silica, talc and attaclay can be used.

The agents containing the substances according to the invention can be anionic, cationic and nonionic, surface-active Substances are added, e.g. to achieve better distribution or better wetting. There are for example soaps, alkyl and aryl sulfonates, quaternary ammonium salts, sugar esters, poly-

Glykolester called The addition of a surface-active Means has a significant increase in effectiveness result.

The funds can be used for the purpose of saving labor or for the purpose of increasing effectiveness with other means of plant protection, such as

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Insecticides, selective herbicides, as well as with Fertilizers or with; use a combination of other growth regulators.

The invention is illustrated by examples for the preparation and purification of individual compounds, which, however, have general validity and for which only the type of amine to be used or amides must be varied, as well as examples of the use of the compounds for regulating plant growth in more detail and for example explained. . ;

Since the compounds exist in 8 tautomeric forms can, among which there are equilibria, it is very difficult to keep them absolutely pure. In addition nor that the enol forms with metals, such as iron, form strongly colored enolates. Because of this, the compounds if they still have traces of contaminating Substances preserved, colored pale yellow. But in an absolutely pure state most of them are colorless, like that Example of the purification of N, N-Di-L4-hydroxy-3,6-dioxohexahydro-pyridazihyl- (4) shows acetyl / cyclohexylamide.

For TLC (thin-layer chromatogram) investigation of N, N-di- / 4-hydroxy-3,6-dioxo-hexahydro-pyridazinyl- (4) -acetyl / amides, 2.ul of a 2% solution are analyzed SIL NH-R UV pre-fabricated film from Macherey & Nagel in Düren applied. The foils are developed in Butanbl / Eisessig / VJasser 80: 20: 20 as a flow agent, while working with chamber saturation.
The running distance is 13 cm. To identify the

^.: '■■■■■■ ■ "■: ^V:: - 14 -

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Stains are then viewed on the films in UV light sprayed with 0.5% dimethylaminobenzaldehyde solution and then dried 10 times at 110 ° in a drying cabinet. The amides show up as yellow, orange or red spots. It is so easy to show whether the substances are uniform and in particular whether they are free

of the starting substance "4-Hydrojq: -3,6-dioxo-hexahydro- -pyridazinyl- (4) -acetic acid.

The compounds have an acidic character and can therefore be determined in a back titration with lye. Here Depending on the temperature or the time, different equivalent values are obtained as most of the amides are broken down in lye when they are boiled. Where it was possible are in the table both values are given.

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example 1

N, N-Di-j_4-hydroxy-3,6-dioxohexahydro-pyridazinyl- (4) -acetyl / -amide.

94 g of 4-hydroxy-S ^ -dioxohexahydro-pyridazinyl- (4) - -acetic acid, mixed with 70 ml of water and this 25 g conc. Amonia given. The mixture is then gently refluxed on the infrared heating bath for 4 hours Boiling heated. The solution is then concentrated to dryness in vacuo in a rotary evaporator at 50.degree. The dry residue is digested with ether to remove impurities to remove. The substance is then im Desiccator after-dried.

There are 93.4 g of the N, N ~ Di-jr4-hydroxy-3,6- -dioxohexahydro-pyridazinyl- (4) / - amides as yellowish colored, crystalline substance with a melting point of 89-90 ° C obtain.

Back titration equivalent found: 180.58

calc .: 178.5

Back titration after 15 min of boiling equivalent found: 91.1

calc .: 89.25

Example 2

N, N-Di- £ 4-hydroxy-3,6-dioxohexahyclropyriaazinyl- (4) -

- acetyl / - amide.
· »/

: -... "■ - ■■■ - '' ■ '"; ■■ - 16 -

50982 0/108 9

75.2 g of 4-hydroxy-3,6-dioxohexahydropyridazinyl- (4) - acetic acid and 74.8 g of 4-hydroxy-3,6-dio>: ohexahydropyridazinyl- (4) Acetic acid amide with 120 ml V7asser - offset. The mixture is heated to gentle boiling under reflux on the infrared heating bath for 4 hours.

The solution is then concentrated to dryness in vacuo in a rotary evaporator at 50.degree. The dry residue is digested with ether to remove impurities. The substance is then dried in a desiccator for a short time.

There are 143 g of the N, N-di- [4-hydroxy-3,6-dioxohe3cahydro- -pyridazinyl- (4) -acetyl / -amids in the form of a yellowish crystalline substance obtained, which melts at 89-90 C.

Back titration equivalent found: .180.4

calc .: 178.5

Back titration after 15 'boiling equivalent found i 86.3

calc .: 89.25

Example 3

N, N, N-tri- £ 4-hydroxy-3,6-dioxohexahydro-pyridazinyl- (4) - - acetyl / amide.

17 g of 10 ^ iges ammonia are diluted with 50 ml of water and added 56.4 g of 4-hydroxy-3,6-dioxohexahydro-pyridazinyl- (4) -acetic acid. The mix will

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at reflux on the infrared heating bath for 4 hours to the heated to a gentle boil; Then the solution is in vacuo concentrated to dryness in a rotary evaporator at 50 ° C. The dry residue is digested with ether and then dried in a desiccator. The DC investigation shows that the substance is uniform.

There were 52 g of the N, N, N-Tri-J_4-hydroxy-3,6- -dioxohexahydro-pyridazinyl- (4) -acetyl] -amides obtained as a yellowish-colored, crystalline substance with a melting point of 75.degree. .

Back titration equivalent found: lS $, 2: • calc .: 175.65

Back titration after 15 'boiling equivalent found s 83.42

calc .: 87.83

Example 4

N, N-Di- | 4-hydroxy-3,6-dioxohexahydro-pyridazinyl- - (4) Acetyl] cyclohexylamide.

37.6 g ^ -hydroxy-S ^ ö-dioxohexahydro-pyridazinyl- - (4) acetic acid and 9.9 g of cyclohexylamide are mixed with 50 ml of Viasser. The mixture is softened for 4 hours on the reflux condenser on the infrared heating bath

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Boiling heated. Thereafter, the mixture is concentrated in vacuo in a rotary evaporator at 50 ⁰ C to dryness.

The residue is digested with ether to remove impurities

to remove. The substance is then dried in a desiccator.

There were 42 g of the N, N-Di- | _4-hydroxy-3,6-dioxohexahydropyridazinyl- (4) -acetyl] - Cyclohexylamids in the form of a yellowish colored, crystalline substance with a Mp of 65 ° C obtained.

Back titration equivalent found: 212.54

calc .: 219.5

Back titration after 15 »boiling. Equivalent found: 119.84

calc .: 109.75

Example 5

Purification of N, N-Di-I4-hydroxy-3,6-dioxohexahydropyridazinyl- (4) -acetyl I -cyclohexylamide.

Oj 43.9 g N, N-Di-I 4-hydroxy-3,6-dioxohexahydro-

pyridazinyl (4) acetyl! -cyclohexylamid are in 100 ml

-J

Dissolved in water. The solution of 11.1 g of calcium chloride in 30 ml of water is added with stirring. The solution is then filtered through a fluted filter. The solution of 8.0 g of NaOH in 50 ml is added to the filtrate

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Water * The precipitate is filtered off with suction and the residue with 30 ml of ice-cold water on the Washed nutsche. The residue will then still be Put moist in a flask and add 120 ml of water offset. To this end, the solution of 12.6 g of oxalic acid dihydrate in 50 ml of water is added. The mixture becomes 20 * heated to boiling under reflux on the infrared heating bath. They are then left sealed overnight stand and suck off the precipitation on the other day. The filtrate is used in a rotary evaporator at 50 ° C Concentrated to dryness, the dry residue digested with ether and dried for a short time in a desiccator.

This gives 16 g of N, N-Di-JjJ-hydroxy-3,6-dioxohexahy dro -pyr ida ζ iny 1 - (4) -a cety ifcyclohexylamids as a pale yellow colored crystalline substance with a Mp 67 ° C.

Back titration after 15 * boiling Equivalent found: 105.8

ber .: 109, IS

100 g N, N-I> i- | 4-hydroxy-3,6-dioxohexahydro * -pyridazinyl - - (4) -acetyl / -cyclchexylamide are dissolved in 250 ml of water. The mixture is made with the addition of 5 g Clarocarbon F briefly heated to the boil and suctioned off while hot. Another 5 g Clarocarbon F are added to the filtrate

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and the mixture as treated above. This is repeated until the mixture is colorless. The reaction is carried out in the dark if possible, with pistons and The feeding bottle is wrapped in aluminum foil. The colorless solution is in a TQflon flask in a vacuum at 50 C to Concentrated to dryness.

There were 27.4 g of the N, N-Di

pyridazinyl- (4) -acetyl / -cyclohexylamide in the form of a colorless crystalline substance with a melting point of 67 ° C. was obtained.

Back titration after 15 · boiling equivalent found: 1O7.8

calc .: 109.75

A TLC examination shows that the substance is uniform and that there are no impurities from the starting substances contains.

Cy 17 g of N, N-Di- | _4-hydrGxy-3,6 "dioxohexahydro ~ pyriaazinyl · - - (4) -acetyl! -Cyclohexylamide are placed in a Soxleth thimble and extracted with methanol in a Soxleth apparatus for 6 hours. The methanolic solution is then in vacuo

concentrated to dryness in a rotary evaporator at 50.degree. 11.9 g of the N, N-di-14-hydroxy-3,6-dioxo-hexahydro- -pyridazinyl- (4) -acetyIJ-cyclohexylamids with a Mp 69 ° C. A TLC study shows that the substance is free of 4-hydroxy-3,6-dio'xo-hexahydro- -pyridazinyl- (4) -acetic acid.

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ück titration equivalent found: 221

\. berV: 219.5 '

Back titration after 15 'boiling Equivalent found: 109.08

calc .: 109.75

The compounds according to the invention can be

speaking one of the for the K, N-Di-! 4-hydroxy-3,6- -dioxo-hexahydro'-pyridazinyl- (4) -acetylj -cyclphexylamide methods a, b or c specified, method c for compounds with: aromatic character is particularly favorable, while it is less suitable for compounds based on aliphatic amines and only gives a poor yield there.

In Table 1 are the formula under consecutive numbering as well as the abbreviated chemical names of the manufactured Compiled substances.

Table 2 lists the physical properties, analysis data and the percentage growth inhibition determined after 15 or 28 days for the substances identified in Table 1. The individual data relate to substances that have not been cleaned to the last. For the The percentage inhibition was determined in / in / pots per 6 wheat plants with 10 ml of a 0.5% aqueous solution of the various Treated substances. The lengths of the stalk were measured after 15 and 28 days and from it that which occurred after the time of treatment

5 0 9 & 2 0 / TO 89 V ;; ■

Growth determined. The percentage inhibition was calculated according to the formula:

Percentage inhibition = 100-100 χ growth of the treated plants

Increase in untreated

calculated.

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games 1-45

"Raas", N-Di-li-t

^ inyl-W -a = et _y £ | -cyc given procedure, the compounds of numbers 1-45 were prepared. :. '■; ■

. . . ■■ ^: - 24

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Table 1

he"! O CQ OO

O OO to

substance
¹ No. • 3 Q stands here as an abbreviation
HN ^y PCS ² " for grouping
with the chemical name:
4-Hydroxy-3, S-dioxD-hexahydro-pyridazinyl- (4) -acetyl- 1
j a Q ^ N j 5 ^ N - H 1
i
6th ^QV N - CH _o CH _o dH _? CH _? CH ₃ ^QV N -WW ' ^QX N Q _x
O ^ ■ - ^ b- f ^ U OLJ f ^ t-J Oj ₁ 1 OLJ Qf ₁ , ι N ₁ N ₁ N-TrL- (Q) -amide i \ E, N — Di- (q) -amid '' ■ '-' N, N-di- (Q) -pentylamide N, N-di- (Q) -butylamide N, N-Di-C Q) -isopentylamide N ₁ N-Di- (Q) -hsxy.lnm id

co

co cn CT) co

OO

Table 1

substance
No.

Q is an abbreviation for the grouping

with the chemical name: A-Hydroxy-S ^ dioxa-hexahydro-pyridazinyl-CA ^ -acetyl-

Q-

CH ₃ N, N-Di-C Q.) -

CH ₃ N, N-Di-fQ) -dodecylamide

u ~

\ J ¹ N, N-Di-CQ) -anilide

10

N-

■ / ~ X

■ ·. / QC1ÖH N j N-Di - (- g) -? ' -carboxy-aniiid

11

Q-

N, N-Di-CQ) benzylamide

CD CO CD CX)

. N-CH

N, N-Di - (■ (i) -cyc

Tabel 1 Q is an abbreviation for the grouping
/ HN-C ^ f ^ _ _CQ _.
HN P \ ni- £ " ¹ ^ of ^the chemical name:
\ n ~~ CH
'O *' ² . ^ -Hydroxy-ajS-dioxQ-hexahydro-pyridazinyl-CAj-acetyl- N, N-Di- (o) -cyclohexanone-P'-methylene-amide substance
No. N, N-Di- (Q) -hydroxylamide ■ ' 509 8 20 / 13th ^ N - OH
^Q N, N-di- (Q) -cyanamide 1089 14th
, Q _x .
^ N-C = N ' ^v . ■ ·. ■. '·;. · ■ N _J N-Di ^ (Q) -acetamide '"· · 15th Q _x .
N - COCH "
Q ^ · Ethyl N, N-di- (Q) -carbamic acid 16 Q _x
. N - GOO C ₀ H-
q / ^ ^b N, N-Di- (n) -? ' -oxo-propionriMurRäthylentsr-3'-amide 17th . N - CH ₅ - CO - COO CoHp
q / ^ ^ ° 18th

cn cn co

Tabel

pi ο co

substance
* No:
■ Q is an abbreviation for the grouping
· '' ■■■ ■■■ ■■ '■■ .. /? '''■■■' ■■ ■ '·' ■■
_/ HN-CvT ^ _CH _ _CQ _.
HN pxnu ² with the chemical. Description: .
Xc- Or ¹ /, ' ■■ "■■ -
- Q * · ² · · ^ -Hydroxy-ae-dioxo-hexahydro-pyridazinyl-iAj-acetyl- '. " ¹ '■''■'''
N, N-Di- (Q) -glycine "·, ■ 19th ■■. Q \ '' '' ■ ■ N ₁ N-Di- (Q) -D, L-alanine. ? 0 Q _v / ^CH 3 ι:
^ N-CH
, Q ' ■' ■ ^X COOH ■ '■''■. · · ■ '' ■■■■ ■ '■''': ■ ■■ '■■■ ■, ■' ■ ' ^: ■■ .. ■■■. ■ '.
Dl-Cal-LC + l-arginine • 21 ^X N - C - NH - (CH_) "- CH-COGH
.; ..,. ■ Q ^ ".- ■■:" ■ - :, ■■ '■. . ■ ■ _ ■■ '■ Tetra- (Q) -L (+} - arginine.. ^: ■ ■■:, '■ ■, -,. ■ '■ ^2? ' ■■■■■■. ■■■. ■■., M ^ J2
, _rt NH ■■■■: ■> N ^
Qv 'π I -
. > N - C 1 - NH - (CH ") - CH - COQH
"" Q ^; ,, ■ V ²³ ..; ■ ■ ': ... Hexa- (Q) -L (+) - arginine ? 3 : ■: ■; ■. '^ ■■. ■ ■ ■■■■■ .. ti · ■ "Q ■, ■■■
■ 'ck 51? Ϊ
^x NCN - (CH ₀ ) - gh; - ^ cdöh ■
N, N-Di- (Q) -L-tyro3in · '' ■■■ ' Pa Q Q. '
HO-f Λ — CH _? - CH- CODH

Table I. Q is an abbreviation for the grouping
Ώ
.HN-C <^ ₀ UP ₀ .. ·
.. · HN. ^ CH ^ " ¹ ^ * of ^{the cnsm} ^ ^ian name:
'■ (f 2 .. 4-Hydroxy-3,6-dioxQ-hexahydrO "-pyridazinyl-C4) -acetyl · - M, N-Di-C Q) -DL-mthionine substance
No. QQ
J '
■ CH-S-DL-CH, -CH-COOH N.N.N'-Tri-CQl-Ethylenediamide '' Ui ? 5 Q _n '/ Q N, N, N ', N'-tetra (Q) ethylenediamide σ
co
OO
ro
ο
■ ν. Q _n / Q
M-CH-CH * -Ν
Q ^ ^N Q.. ...
Ν, Ν, Ν ¹ , N'-Tetra-Cal-hexamethylene-diamide ': —Λ
σ
OO
<0 Q \ · / Q ' N _f N, N ^l , N "-Tetra- (Q) -dipropylf; ntriannide N — CCH -) - NH- (CH _O ) "- Ν;
q / " ^3. · ^{? 3 N} Q N, N, N ', N ", N" -penta- (θ) -dipropylenetriarnid _Q /.· ·? 3 ^J P 3. ^N \ _g 30th

co ⁰⁰ I

co cn σϊ co

'Table 1

substance
No. Q stands here as an abbreviation
ΓΗ. V, W \ ^^^, C
''. Φ 2 for grouping
. '■' ■ '. ■ with the chemical name:'
^ 'r'rlydrpxy-3, S-dioxo-hexahydro-pyridaZinyl-: C4) -acety1-i N, N-Di-CQ) -N ', N'-dimethyl-hydrazide / 31. ; ■■ ;. _y N -N _n . ■ N.NjN'jN'-Tetra-C ^ -hycirazid;,; ';';':';:'^{■; ';'.}' : ''', V "'''■;" ■ '■' V ■■ '■' ^Q x ^:
>^; : Ν
■■ '■■ ^Q I. ' , " ■" ■■■■■■■■■. '; ■ '■ ■■.!. ■■ - ■ ^; · .: ''^'■.'. ■ ■ '' ■■, ^{..;;, 1} Z, ■ ■; '' ,, ■ '■' ■. '■: ■■ ,,' ■ ',' ■ '■' ■
■ ^: 'ϊν ·' ^! '',. ■■■■■ '": ■ ^;; ' ^: '■ ■ ■". ' . ■ '■ ■■>■■;'■■; ■■ ': ^v , ■', "■ ■ '■ ..' ■ .. ■■ ,, '■'"'■■. ■. ■■ .: '''^;'; ■ ': ■ ^ν ,' ■ ■ ■ ■
■ I. -Τ-: CG * ■, '.. ■ · ■■■ .. ■:, ■■. ■ .- ,,, .. ■ .. ■■■■ ■. ■■,,,. ......... .
,. ... ...,, ...... ■. . ,. . ..... ,,. ,,,. ,. ■ ■> ■ ... ·.
. ■■ .. ■■ '·''■ · -. ■; ■ ·, ■ '■ ■■. ■■ · ■■ ■. . ■■. : ■. ■ '■, ■■. ■■. ■■■ .. ■ ■.
N ^ N-Dx-Cq) -N _'t N'-dimethyl-ureide, _\::: ""'■■ 34 "■■' ■ · ' ^Q ' v
■■■■■; ■ '. > -ν
... -. _: -Q <- - co, - ■ 'Γ''.'^.-''-''.'- o. ^1. ' ¹ : ': "^' ^ '''"■■' ■: ■■ ' ^: .'. '. ■'^!; '■'. ^% '. '■■' ■ ·: '. . '■■''.■' ■ '■'''
N, N-Di-CQ) phenylureide _;
, ■ ■, '■ ■. ■■■■' ■ '' ■ '..' ■ ', ■,' ■ '. ■'. . ,; . ■, '
■ '''ι','''■''' I ', "'>'' ■■■ ■:
'' / 35; ■ ■■
s · ' ^! · '■''■■ . '■■■■ :: , Ρ \
; . ·. ■ Q ^, ) ■ '■' ■ ': "■■ :.' N, N, N'-Tri- (Qj-phenylurisld · ■■ ',., ...
■ '. ■. ■ ■' .. ■■■■ '■ ■■. ■■■■'"'■ ! ■, ■■■■■.
! '■■: ^ f N
■ - co- *
V ^GH 3 ■. . . ■ ' Q '..

Ca> C »

i table 1

,
substance
¹ No. I. Q is an abbreviation for the grouping
. .0 ■
¹ ^ · P \ nu ^ ^m ^ ^{t of the} chemical name: '·
\ q _ Q ^ / ^un . ■ = ·
'0 * ² ·. 4-Hydroxy-3 _l 6 ~ dioxa-hexahydro-pyridazinyl- (4) -acetyl- N, N · Di (Q) -nitroso-methyl-ureide 37 Q .CH
. · ^ N- CO-N ^. ·
Q ^ ^ NQ N, N, N ¹ , N'-tetra- (Q) -thioureide 38 ^ NC -N ^
(T ' ^X Q N, N'-di- (Q) -trimethylene-thioureid
! I.
! -39 T etra- (Q) -b iu ret 40 Q _x . / Q
n-co-nh-co-n.
q / ^s q. Penta (Q) biuret 41 Q _x f / Q
^ N-CO-N -CO -N
Q ⁷ · ■ Well PBnta- (Q) -gu.anid.id - / Q
_y IM— CN
c / "^ q

Tabel • 1 ■ N, N-Di- (Q) -maloenyl-guanidide ". substance
No. Q is an abbreviation for dia grouping
, ■ 0.
.. HN., ^ \ R \ ß -with the chemical name:
\ c - CH ^
· ■ ■ '' d * ² ·· a-Hydroxy-aje-dioxo-hexahydro-pyridazinyl - ^ - acetyl- Tetra (Q) biguanide OI . 43
• Q _n ^ ^N - ^co \
Q ^y ^ NH-CO ^ Hepta- (Q) -biguanide
1 09820 / 44 NH NH _
Q \ It Il / ^Q
) n — c — nh —c —n _v • '' '' ' M 08 9 ■
45 ^Q \ ¥ _v Il / ^Q
; nc ~ n - c— n ^. . · • • * «

• • colour solubility BACKITRATION • ber.
found 175.67
185 ,? . after 15 min
Cook .Weight PERCENTUALS • 47 ,? OJ
CTl consistency yellowish 1. in H _? 0
unl in C ₀ H-OH without
Cook 178.5
180.58 Equiv 87.83
83.4? HEKMJNG AFTER
DAYS "33, C cn
Approx
σ>
OO substance
No. Krist. "
M.p. 75 ° "yellowish ' '1. in HpO
unl in CpH ₅ OH Mol. '
weight ber.
found '89,? 5
86.8 50.0 1 Krist.
M.p. 89-90 ° yellowish 1. in H _? 0
l. in C "H _C OH little ber.
found ber.
found S.
106.75
97.31: 50.0 3?, 7 ? Krist.
M.p. 70 ° yellowish
• 1. in H ₂ O
1. Little in CpH ₅ OH ber.
found ber.
found 103,? 5
105.5 33.0 15.9 3 Krist. hygrosc.
M.p. 70-100 ° ' yellowish 1. in HpO
l. in C ₇ HJDH little ·: 146.47
158.49 ber.
found 106.75
99.71 46.7 5?, 8 4th Krist.
M.p. 78 ° yellowish 1. in HpO
l. little in CpHgOH ber.
found 109.85
130.63 35.5 5 Krist.
Fn. 60 ° ber.
, gef · 38 ,? 6th 50.0

«Under foaming

Tabs! Is 2

BACKITRATION

without cooking

after 15 min of boiling

PERCENTAGE INHIBITION BY DAYS

substance
No.

consistency

colour

solubility

Mole weight

Equiv. Weight

Krist. M.p. 75 °

yellowish

unl.in HO
I. in G ₀ H ₅ OH

ber.? 33.74 ? 08.83

ber. 77.91 found. 8?, 05

40.0

? '5.0

Krist. Mp 90 °

yellowish·

unl. in H _? 0

1. in G ₀ H-OH
P 5

ber. 131,? 5 found. 1? 5.33

47.1

■ 3?, 6

Krist. M.p. 78 °

yellowish

1. in HpO
1. in C ₀ Hp ₅

,little

over,? 16.5 found. ? 09.4S '

ber. 108,? 5 found. 93.44

? 9, B.

10.9

10

Krist, fn. 84

faint gray

1. in H _? 0
unl.in C ₀ H ₁ JDH

calc. 159.0 found 119.65

ber. 95.4 found 78.97

35.3

13.9

11

crystal "mp. 65 °

yellowish

1. in
l.in

little

calc. 111.75 found. 11?, 3

66.0

66.0

K) CaI Ol

Krist. .

Footnote 69 °

yellowish

1. in H _? 0

1. Little in C _n H-OH

ber.? 19.5 found PI ¹ P ₁ S *

ber. 109.75 119.84

66.0

33.0

+ ■ under foaming

Tgbeils 2 • colour solubility BACKITRATION 116,? 5
118.9 after £ 1
Cook 114.9 PERCENTUALS • 21 Λ consistency brownish unl.ir F _O 3
1.3 η C ₀ H-OH little without
Cook · 186.5
168.7 95.6
87.5 INHIBITION AFTER
DAILY 50 O Krist. ·
Fp. 5 ° 1. in H _? O
unl. in C ₀ H ₅ OH Mole.
weight 1? 7.33 ■ 99.75
88.61 ? 5 " Krist.
Fo. 96 ° yellowish 1. in H _? 0
unl. ϊη C ₀ H-OH ber.
• found 133, Ό "
148,? 9 3 min . 85.8
81.03. 35.1 50 ι O Krist.
M.p. 70 ° yellowish 1. in H _? 0
unl in C ₀ H ₅ OH ber.
found Ίθ7,? 5,
108.91 Equiv. Weight 78.5
77.98 6?,? 33 , 0 Krist,
Fn, 79 ° yellowish 1. in H _? 0
unl.in C _o H _r 0H ber.
found 157.0
168.74 ' 36.7. 33 , 0 substance
No. kri st.
Pp. 58 ° brownish 1. in H _? 0
unl.in C ₀ H ₁ JDH • ber.
found ber.
found 6?, P , 0 13th Krist.
Pn. 105 ° ber.
found ber.
found 33.0 14th ber.
found ber.
found 33.0 15th ber.
found ber. 18th

«Under foaming

Table · p ο • consistency - • solubility BACKITRATION without
Cook after 15 min
Cook weight ¹ PERCENTAGE • ? 0, 5 • ,! NSPEC Krist. ·
M.p. 61 ° colour 1. in HpO
unl.in C _n H-OH Mole.
weight Equiv. 103.75
98.9 INHIBITION AFTER
DAYS 17, M.
/ α 'dance'
No, Krist.
Fp. 8 ° yellowish 1. in HpO
'unl in C ₀ H-OH ber. 138.3
found 13?, 0 ber.
found 107.25
105.73 33, 0 ε- ¹ B. Krist.
Fo. 105 ° .yellow 1. in HpO ber. 143.0
found 156.5? ber.
found 128, <5
1? 6.0? . 29.4 17, 1 20th ■ 'Krist.
Mp. 120 ° yellowish 1. in HpO
unl in CpH-OH ber.? 57.0
found ? 09.54 ber.
found 106.75
105.79 48.6 9, 8th Krist.
Mp. 120 ° .yellowish '1. in H _? 0
unl in C ₀ H-OH
ei O ■ '' about,
found 99.5
87.8? . 66.0 31 8th Krist.
. M.p. 145-150 ° yellowish 1. in H ₀ O
unl in CpH ₅ OH ber. 149.26,,
found 146.26 ber.
. found 104 ,?
94.9? 37.8- 23 yellowish ber. 173.67
found 151.64 ber.
• ^; found 43.2 24 37.8

uritar ranks

5098 20/1089

Table 2

• • • colour - solubility RtJCKTITRATIHN without
. Cook after 15 min
Cook Not PERCENTUALS t • 33, 0 * consistency yellowish unl. in HgO
l. in CLH ₅ OH little Mole.
weight Equiv. 167.7
173.08 INHIBITION AFTER
DAYS 33, 0 Svbi :dance Krist. "
M.p. 98 ° . yellowish 1. in HpO
unl in CpH ₅ OH ber. 251.5
found ? 03.85 ber.
found 95.0
98.8 Q 33 0 » Krist.
M.p. 110 ° yellowish 1. in HpO
unl in CpH ₅ OH b'er. ^;
found 9? , · 5
107.6 66.0 39 , 6 ? 6 Krist.hygrosk.
Mp. 1? 5 ° ⁺ yellowish 1. in HpO
l. in CpH ₅ OH less ber.
found 99.5
105.9? 66.0 33 , 0 O ? 7 . 'Krist.
M.p. 79 ° . yellowish l.in HpO
unl in CpH ₅ OH ber. 13?, 7 *
found 148.75 ber.
found 101.3
93.5. 33.0. 33 , 0 SE
r " 2Θ Krist.
Mp. 66 ° yellowish 1. in HJD
unl.in C "H_OH found
ber. 98.1 6?,? · ~ a
ίτι 29 Krist.hygrosk.
Mp. 11S ⁰⁺ · ber. 33.0 30th 33.0

with foaming; ^ O ^ 9T2TT7 ~ tu b

Table 2

BACKITRATION

without kitchens

after 15 min of boiling

PERCENTAGE INHIBITION BY DAYS

substance
No.

consistency

colour

solubility

Mole weight

Equiv. Weight

28 '

31.

Krist. M.p. 63 ^C.

brownish

1. in
unl.in

ber. 200.0 found 144.78

ber. 100.0 found 90.88

53.3

55.6

3?

Krist, hygrosc. M.p. 135 ° ⁺

yellowish

1. in H _? 0
unl.in C ₂

, 0H

ber. 89.0 found 88 ,?

50.0

55.6

33

34

Krist. M.p. 67 ^C.

yellowish

1. in H _? Q
unl.in C ₂ H

ber. 9?, 5 f. 88.15

Krist. Fp. 7? ^C.

yellowish.

1. in H _? 0
unl in CpH

ber. 85.6 found 85.0

59.4

46.7

3? _t 6

41.7

35

Krist. M.p. 75-eO ^c

yellow-brown

unl.in H _p 0

unl.in

calc. 158.7, found 151.53

ber. 95,? found 100.26

33.0

33.0

CD CO OD

36.

Krist. Fp. 118 '

ο +

yellowish

unl.in H _? 0
unl.in C _? HJ

OH

ber. 1? 9.0 f. 1? 4.0

ber. 9?,? 9 found. 98.1

66.0

66.0

+ «Under foaming

50 9 820/1089

TaDeIlS 2 • substance
No. consistency colour solubility BACK TITRATIDN without
Cook after 15 min
Cook PERCENTUALS
INHIBITION AFTER
DAYS 36, fi O
Π 37 Krist.
M.p. 71 ° brownish 1. in H _? 0
unl.irt C ₅₁ H ₅ OH Mole.
weight Equiv. Weight • 30 _v 9 »
O
D.
O 38 Krist
M.p. 70 ° yellowish 1. in H ₂ O
unl.in O ₅ H ₅ OH ber. 110.75
found 117.8. , calc. 88.6
found 81, ?? 47.5 33.0 39 Krist.
Fp. V, qP yellowish ■ 1. in H ₂ O
• unl.in CpH ₅ OH ber. 84.0
found , 8?, 59 46.7 74 ,? 40
O Krist.
M.p. 78 ° yellowish, 1. in H _? 0
unl in C ₂ H ₅ OH ber. 91; 8
found 96.9 33.0 45.3 y
< Z 41
>
f Krist.
Mp 90 ° yellowish '1. · in H ₂ O
unl in C ₀ H-OH • ber. ' 111.85
found 111.88 '■' t 68.9 ■
36.4 ω
Ό
ro /, ο
πη.
α Krist ,. .
M.p. 74 ° greenish 1. in H _? 0
unl in CpH ₅ OH ber / 136.14
found 14?, 41 ber. 95.3
found 94,? 1 64.4 ber. 90.9
found 90.8? ber. 113.63
• found 111.85 55.0

+ «■ frothing untarely

509820/1 089

Table 2 > • * colour solubility • RlJCKTITRATinN without
Cook 155.7
131.37 after 15
Cook min • 77,? 5
8?, 48 PERCENTUALS ? 5, c
I. consistency yellowish 1. in H _? 0
unl in CH ₅ OH Mole.
weight 130,? 7
138.05 Equiv. Weight 111.6
ii0.9? INHIBITION AFTER
DAYS •? 5, D * krisfc.
Fp. 1Γ ^ν 5 •yellowish 1. in H _? 0
unl.in C _? H _g OH ber.
. gef; ber.
, found 9? J?
98.0 ? 9.6 substance
No. Krist.
Mp. 7 ° -75 ° yellowish 1. in H "0
unl in Cj ₃ H ₅ OH ber. • about *
found 43.3 43 Krist.
M.p. 70 ° • ber.
found 6?,? UA • 51.1 • ORIGIN . 45 · M INSPECTED 1
i
1
j

LO CD CO

foaming up

Claims (56)

Patent claims 1. Organic chemical compounds with the grouping (N, N-Di- ^ 4-hydroxy-3, 6-dioxo-hexahydro-pyridazinyl- (4) -acetyl / ■ amide = N, N-Di-Q-amide) or tautomeric forms thereof. 2. A compound according to claim 1, in which the free valence is replaced by hydrogen, the cyano or hydroxyl group is occupied. 3. Compound according to claim 1, wherein the free valence by a Amino group is occupied. 4. A compound according to claim 3 with the designation N, N-Di- (Q) -N ', N'-dimethyl-hydrazide. 509820/1089 5. A compound according to claim 3 with the designation Ν, Ν, Ν ', Ν'-tetra (Q) hydrazide. 6. The compound of claim 1, wherein the free valence by a straight or branched chain alkyl radical with 1-16 carbon atoms, preferably 4-7 carbon atoms, is occupied. 7. A compound according to claim 6 with the designation N ₁ N-Di- (Q) - pentylamide. 8. A compound according to claim 6 with the designation N, N-Di- (Q) - butylamide. 9. A compound according to claim 6 with the designation N, N-di- (Q) _r isopentylamide. 10. A compound according to claim 6 with the designation N, N-Di- (Q) - hexylamide. 11. A compound according to claim 6 with the designation N, N -di (Q) -octylamide. 12. A compound according to claim 6 with the designation N, N-di- (Q) -dodecylamide. - 13. A compound according to claim 6 with the designation N, N-di- (Q) -2'-oxo-propionic acid ethyl ester-3'-amide. 14. A compound according to claim 6 with the designation N, N, N'-tri- (Q) - ethylenediamide. - 42 - 50982 071089 .. 15th A compound as claimed in claim 6 , which is N, N, N ^J , N'-tetra (Q) ethylenediamide. 16. A compound according to claim 6 with the designation N, N, Ni N 'tetra- (Q) -hexamethylene-diamide . 17. A compound according to claim 6 with the designation Ν, N, N ', N ^J ' - Tetra - (Q) - dip propylene triamide. 18. A compound according to claim 6 with the designation Ν, Ν, Ν 'JSf' *, N ^J penta- (Q) - dirpopylenetriamide. 19. The compound of claim 1, wherein the free valence by a alicyclic radical is occupied. 20. A compound according to claim 19 with the designation N, N-Di- (Q) - cyclohexylamide. 21. A compound according to claim 19 with the designation N ₁ N, -di (Q) -cyclohexanone-2'-methylene-amide. 22. A compound according to claim 1, in which the free valence is occupied by an aromatic ring or aromatic ring system is. 23. A compound according to claim 22 with the designation N, N, -Di- (Q) - anilide. 24. A compound according to claim 22 with the designation N, N, -Di- (Q) -2 ' -carboxy-anilide. - 43 - 509820/1089 25. The compound of claim 1, wherein the free valence by an aralkyl radical is occupied. 26. A compound according to claim 25 with the designation benzylamide. 27. Compound according to Claim 1, in which the N, N-Di- (Q) -amid group replacement of the amino group of an amino acid. 28. A compound according to claim 27 with the designation N, N-Di- (Q) - glycine. 29. A compound according to claim 27 with the designation N, N-Di- (Q) - DjpL-alanin. 30. A compound according to claim 27 with the designation Di- (Q) -L (+) - ar ginin. 31. A compound according to claim 27 with the designation Tetra- (Q) - L (+) - arginine. 32. Compound according to claim 27 with the designation hexa- (Q) -L (+) arginine. 33. A compound according to claim 27 with the designation N, N-di- (Q) -L-tyrosine. 34. Compound according to claim 27 with the designation Ν, Ν-Di-fjQ) - DL-ethionine. 509 820/1089 35. Compound according to claim 1, _{wherein the N 1} N-di- (Q) -amid- Grouping the amido group of an acid amide or thio acid amide replaced. 36. A compound according to claim 35 with the designation Ν, Ν, Ν ', Ν'- Tetra (Q) ureide. 37. Compound according to claim 35 with the designation N ₁ N-Di- (Q) - N ', N' -dimethyl ureide. 38. Compound according to claim 35 with the designation N, N-Di- (Q) - phenylureid. 39. Compound according to claim 35 with the designation N ₁ N, N '-Tri- (Q) -phenylureide. 40. A compound according to claim 35 with the designation N, N '-Di- (Q) - nitroso-methyl-ureide. 41. Compound according to claim 35 with the designation N, N ₁ N ', N'- Tetra- (Q) -thiour oath. 42. A compound according to claim 35 with the designation N ₁ N * -di (Q) -trimethylene-thioureide. 43. A compound according to claim 35 with the designation tetra- (Q) -biuret. 44. Compound according to claim 35 with the designation penta (Q) - biuret. - 45 - 5098 20/1089 45. Compound according to claim 35 with the designation penta (Q) - guanidid. 46. Compound according to claim 35 with the designation N, N, -Di- (Q) - malonyl guanidide. 47. Compound according to claim 35 with the designation Tetra- (Q) - biguanid. . 48. A compound according to claim 35 with the designation hepta- (Q) -biguanide. 49. Compound according to claim 1, wherein the free valence by a Acyl residue is replaced by an organic acid. 50. A compound according to claim 49 with the designation N ₁ N-di- (Q) -acetamide. 51. Compound according to claim 49 with the designation N, N-Di- (Q) - carbamic acid ethyl ester. 52. A compound according to claim 49 with the designation Ν, Ν, Ν-tri-. (Q) -amide. 53. - ^ Compound according to claim 1, in which the N, N-di- (Q) -amid- group tion occurs two or more times. - 46 - 509820/1089 54. Process for the preparation of N, N-di- / ^ - hydroxy-3, 6-dioxo- hexahydro-pyridazinyl- (4) -acetyl ~ / - amides, thereby characterized in that an amine or an amide which still carries two hydrogen atoms on the nitrogen has two moles 4-Hydroxy-3,6-dioxo-hexahydro-pyridazinyl- (4) -acetic acid is reacted by heating in an aqueous medium. 55. Process for the preparation of Ν, Ν-di- / 4-hydroxy-3, 6-dioxohexahydro-pyridazinyl- (4) -acetyl ~ I -amides, characterized in that a 4-hydroxy-3, 6-dioxo -hexahydro pyridazinyl- (4) -acetic acid amide, which still has a hydrogen atom on the amide component, with one mole of 4-hydroxy-3,6-dioxo-hexahydro-pyridaviinyl- (4) -acetic acid is reacted by heating in an aqueous medium. 56. Use of the compounds according to claims 1-53 for regulating plant growth. 509820/1 089