MEANS FOR THE ADJUSTMENT OF PLANT GROWTH

The invention concerns means for the adjustment of plant growth. They contain partly well-known Plperazin derivatives than active substances. It is already become known that certain Piperazin derivatives possess therapeußsehe effectiveness (see J.Amer. Pharm. Ate. 46, S.279 to 289 and brit. Patent specification Nr.901, 187). Further it is become known that certain 2-Halogenäthyl-triaIkylammenium-halogenide exhibits pflanzenwuehsreguäerende Eigenschaßen (see USA Patentsehrift Nr.3, 15 6, 554 or auehdeutsehe laying out writing 1,642,215). The-work-gnaw these materials is however, particularly with low expenditure quantities and - kenzentratienen, not always satisfying. It was found that the partial well-known Piperazin derivatives of the general formula RI n 2 R in soft Rl, R2 and R-S independently for if necessary suhstituiertes alkyl, gegebenenfaI [s substituted alkenyl, AlkinyI, Cycloalkyl or fiir in the ArylteiI substituted Aralkyl to stand if necessary and for whole numbers from 0 to 4 stands for n, strong pflanzenwuchsreguHerende characteristics to exhibit. The subject of the invention is from there a means to the ReguIierung of the Pflanzenwachstnms that by the fact it is characterized that it a Piperazin derivative of the general formula (i) beside Streekmitteln and/or or carrier means and/or or oberfläehenaküven means and different active substances contains if necessary. Surprisingly invention in accordance with tBen Piperazin derivatives show containing means one raise-borrowed higher pflanzenwuehsreguHerende effect than from state of the art well-known (2-Chloräthyl) - - tri methyl ammonium chloride, which is a recognition well effective material of same mode of action. The erflndungsgemäßen 1VitteI represents thus a valuable enrichment of the technology. The Piperazin derivatives contained in the erfiodungsgemäßen means are by the general formula (I) clearly defined. In the formula (I) stands E1 preferably for geradkettiges or branched alkyl oderAlkenyl mlt up to 4 throat material atoms, whereby everyone can be ert this Alkyloder Alkeaylreste by Hydroxyi, carboxyl and/or Methylcarbonyl substi. 1 2 stands preferably for geradket iges or branched alkyl with 6 to 18 carbon atoms, geradsinniges or branched alkenyl with 6 to 18 carbon atoms, in particular with 8 to 12Kohlenstoffatomen, geradke iges or branched Alkinyl with 6 to 18 carbon atoms, furthermore for Cycloalkyl with 3 to 8 throat material atoms as well as for in the Aryiteil by halogen and/or alkyl with 1 to 6 carbon atoms substituted Aralkyl with 6 to 10 carbon atoms imArylteil and for 1 or 2 carbon atoms if necessary in the Alkylteil.B3 stands in the formula (I) preferably for geradsinniges or branched alkyl with 1 to 6 Koh] as well as enstoffatomen for geradsinniges oderverzweigtes alkenyl with 2 to 6 Kohienstoffatoman. In the formula (I) preferably stands A for the whole numbers of i or 2. As examples of usable the according to invention active substances are in detail mentioned: 1-Methyl -4-hexyl-piperazin, 1-Methyl-4-heptyl-piperazin, 1-1Viethyl-4-octyl-piperazin, 1-Methyl-4-nonyl-piperazin, 1-Methyl-4-deeyl-piperazin, 1-Methyl-4-undeoyl-piperazißl-Methyl-4-dodecyl-piperazia, 1-Mehhyl-4-trideeyl-piperazin, 1-1V e hyl-4-tetradecyl-piperazin, 1 - {etbyl-4-peatadecyl-piperazin, 1-Methyl-4-hexadeoyl - plperazin, 1-1VIethyl-4-heptacetyl-piperazin, 1-Methyl-4-octadecyl-piperazin, 1-1V ethyl-4-undec-10-enyl - piperazin, 1-1VIethyl-4-octadec-9-enyl-piperazin, 1 - Methyl4 octadeca-9, 12-dienyi-piperazin, 1-Äthyl -4-hexyl-piperazin, 1 - Ätbyl4 heptane piperazin, 1-Äthyl-4-oetyl-piperazin, 1-Äthyl-4-nonyl-piperazin, 1-Äthyl-4-decyl-piperazin, 1-Äthyl-4-undecyl-piperazin, 1-Äthyl-4-dodecyi-piperazin, 1thyi-4-tridecyl - piperazin, 1-Äthyl-4-tetradecyl-piperazin, 1-Äthyl-4-pentadecyl-piperazin, 1-Äthyl-4-hexadecyl-piperazin, lthyl-4-heptadeeylpiperazin, 1 - Ä hyl4 oetadecyi-piperazin, I - Äthyl4 unden-10-enyl-plperazin, 1-Äthyl-4-eotadec-9-enyl-piperazin, 1-Methyl-4-benzyl-piperazin, l-Methyl (4-pentylhenzyl) - plperazin, I, 3-Di-methyl-4-oetyl-piperazin, 1, 3-Di-methyl-4-de yl-piperazin, 1, 2, 5-Trimethyl-4-decyl-piperazin. Usable the according to invention materials are partly admit (see J. Amer. Pharm.Assoe. 46, P. 279 to 289 and brit. Patentsohrift Nr.30 I87). Their use for the adjustment of plant growth is however new. Particulars verwenäbaren of the according to invention materials are new; they can be manufactured however in simple way in well-known procedures. One e.g. receives it, if one forms a) a Piperazin of the general! B1 _ n \ NH \ (S3) n in which R! , 1 3 and n the meaning indicated above has, with a connection of the general formula eT) a2 _ x, (III) into which R2 the meaning indicated above and X has stands for halogen or p-Toluolsulfonyl, if necessary in presence of an inert solvent, preferably however in absence of a solvent, at temperatures between 20 and 150°Cumsetzt and from the salts by treatment with a sänrebindenden means, as for example aqueous alkali hydroxide, developing thereby, which connections of the formula (1) sets free, or if one b) a Piperazidid of the general formula O I \ II _ i 4 1 1 - N numerical control (R3) n in which I l, R3 and n those above and B4 for if necessary more substituter it alkyl, if necessary substituted alkenyl, AlkinyI or for Aralkyl substituießes in the aryl part have indicated meaning e.g. stand if necessary, with an l edukHensmittel, like Lithiumalanat, in an inert solvent, as e.g. tetrahydrofurane converts, at temperatures between 0 and 100°C, or if one c) of nitriles of the general formula l “- CN, (v) into which B4 the meaning specified above has, also in situ manufactured Divinylaminen of the general formula 2, ° N-- T1 (vD in which Bi, B3 and n the meaning indicated above have, in presence of an inert organic solvent, like e.g. dimethylformamide, as well as in presence of a hydrogenation catalyst, as e.g. Baney nickel, under a hydrogen printing from 50 to 250 at temperatures between 50 and 200°C hydrogenated (see brit. Patent specification Nr.901, 187) o the Piperazine of the formula (left), usable at the time of the execution of the procedure (A) as basic materials, are to a large extent admits (see “Handbook OF Chemlstry and Physics”, 45 th. Edition, S.O. 479). Those so far yet do not vorbesehriebenen basic materials of the formula (II) after-well-known Mefhodendarstellen leaves itself (see USA patent specification Nr.2, 525.223 and Nr.2, 636, 032). As examples of the Piperazine of the formula (II) are in detail mentioned: 1Methyl-piperazin, 1, 2, 5-Trimethyl-piperazia, 1-Äthyl-piperazin and 1-Isopropyl-piperazin. With derDurehführung the procedure (A) the connections of the formula ([IL), usable as reaction components, are likewise admits (vglo Chen. Second., S.636 to 647; Chem. seconds., so 644 to 054; German realm Reich Nr.695 062 and Nr.567 014; J. Amer. Chen. Second. 55, P. 1578; brit. Patent specification Nr.565, 452 as well as USA patent specification Nr.1, 950, 827). As examples of connections of the formula (III) are in detail mentioned: 1-Chlorhexan, 1-Chlorheptan, 1-Chloroctan, 1-Chlornonan, 1-Chlordecan, 1-Chlorundeean, 1-Chlordodeean, 1-Chlortrideean, 1-Chlortetradecan, 1-Chlorpentadecan, 1-Chlorhexadecan, 1-Chlorheptadecan, 1-Chloroctadecan, benzyle chloride and ChlormethylnaphthaHn as well as the enüsprecheuden bromine connections. With that through ihrung the procedure (A) one uses preferably 1 mol of a connection of the formula OH on 1 mol of a Piperazins of the formula gl)). A Überoder Unterschreiümg of indicated stoichiometric conditions is possible, brings however no substantial yield improvement. During the heart filling usable of the according to invention materials in the procedure (A) the reaction products result after terminated conversion first in the form of salts. To the isolation freieu of the connections of the formula (I) e.g. over-laminates one the salts with solvents, like ethers, organic with water not misehbaren, polar, Cyclohexanol or Isobuhanol, deletes then an equivalent quantity of an aqueous alkali hydroxide solution in addition, vibrated, separates the organic phase and removes the solvent. At the time of the execution of the procedure 0o) as AusgangsstoffeverwendbareuPiperazididederFormel (IV) are partly admits (see USA Patentschrif Nr.3, 147, 261). Those so far yet before describe again connections of the formula (IV) cannot be represented according to well-known in principle methods. One e.g. receives it, by one a Säureehlorid of of the general formula R4 - coCl, (v) in which R4 indicated the meaning the above has with a Piperazin of the formula (IL) converts. The Säurechloride of the formula (front spar) are admit (see Ber. 17, P. 1378; Ber. 23, S.2385; Ber. 31, P. 2348; Helv. Chim. Acta 22, S.89; Recueil of the Travaux Chimiques of the Pays Bas 18, 8th 253 and J. Amer. Chen. 8oc. 66, 8,287). With derDurchfühnmg the procedure (C) of usable nitriles of the formula (V) are likewise admits (see J. prak Chen., S.634; Ber. 12, 8.1888; Liebigs arm. Chen. 495, P. 110; Comptes Rendues 213, S.270; J. Amer. Chen. Second. 58, S.348; ibid. 59, S.987; ibid. 64; P. 1362; ibid. 64, 8.1517; ibid. 66, S.362 and BI. Second. Chim. Belg. 42, S.179). In situ production of Divinylaminen of the formula (VI) is already admits (see a Britisher patent specification Nr.901, 187). Usable the according to invention active substances intervene in the metabolism of the PfIauzen and can be used therefore as growth modulators. For the impact of plant growth modulators it is valid after the past experience that an active substance can have or also several different effects on plants. The effects of the materials hang essentially off of the time of application, related to the development stage of the seed or the plant as well as of the active substance quantities yielded on the plants or their environment and of the kind of the application. In each case growth modulators are to positively affect the Kulturpflanzeu in desired way. Plant-stature-adjusting materials can be used e.g. for the inhibition of vegetative plant growth. A such stature inhibition is among other things with grasses of economic interest, because by one absorption of the grass growth the frequency of the Grasschnit±einZiergärteu, Parkund sports site can be e.g. reduced or at edges of road. From B edeutnng also the inhibition of the stature of krautigen and holzigen plants at Straßeurändern and in close proximity to Überlandleitungeu is or completely general in ranges, within which a strong vegetation is unwanted. Important also the use from growth modulators is to the inhibition of length growth with grain, because by a Halmverkürznng the danger of the Umknickens of storing ") the plants before the harvest is reduced or eliminated perfectly. In addition köunen growth modulators with grain a Halmverstärknng cause, which likewise works against storing. An inhibition of vegetative growth permits with many cultivated plants a closer cultivation to the culture, so that a increment-referred to the floor space can be obtained. A further mechanism of the Erüragssteigerung with Wuchshemmeru is based on that the nutrients benefit in stronger measure Blütenund fruit formation, while vegetative growth is limited. With growth modulators frequently also a promotion of the vegetative Waehstums lets itself obtain. This is very useful, if the vegetative plant parts are harvested. In addition, a promotion of vegetative growth can lead at the same time to a promotion of the generaüven Waehstums, so that e.g. more or larger fruits come to the training. Increased returns can be achieved in some cases also by an interference in the vegetable Stoffwechsei, without mderungen themselves vegetative growth make noticeable. Furthermore Waehstumsregula oren can a change of the composition of the plants cause” around so a better quality of the harvest products to cause. Like that it is for example possible, the content of sugars in sugar beets, Zuckerrohr, to increase pineapple as well as Citrusfrüchten or the protein content in soy or Ge - treide to increase. Under the influence of growth modulators it can come to the training of parthenokarper fruits. Furthermore the sex of the blooms can be affected. MitWachstumsregulaturen lets itself positively affect also production or the discharge of secondary plant materials. As example the stimulation of the Latexflusses is mentioned with Gummibäumen. During the growth of the plant also the lateral bypass can by a chemical refraction of the Apika by use of WachstumsreguIatoren [dominance to be increased. To it e.g. exists. Interest during the cutting stecklingsvermehrung of plants. IT is however also possible to restrain the Waehstum of the Seitentrlehe to e.g. prevent in order with tobacco plants after the Dekapitierung the training from side impulses to and to promote thus sheet growth. Under the influence of growth modulators the sheet existence can be steered by plants in such a way that a Entbläßern of the plants is reached at a desired time. A such Entlaubung is of interest, around a mechanical Beernlnng, Zoß. with wine or cotton to facilitate or lower around the transpiration at one time, on which the plant is to be transplanted. By use of growth modulators the premature Fruehtfall lets itself prevent. It is however also possible, fruit-resounds - e.g. with fruit - in the sense of a chemical thinning out up to a certain extent to promote. Growth modulators can also serve in order to decrease with cultivated plants at the time the harvest Kraft necessary for the replacement of the fruits, so that a mechanical Beerntung of the plants is made possible and/or a manual Beernümg is facilitated. With growth modulators furthermore a Beschleuaignng or also a delay that-ripe of the harvested crop before or after the harvest lets themselves reach. This is from special advantage, because thereby an optimal adjustment lets itself cause to the needs of the market. Further know Wachsi msregulatoren in some cases the fruit from colouring to improve. In addition assistance of growth modulators also a temporal concentration the ripe one can be obtained. Thus the conditions for are created that e.g. with tobacco, tomatoes or coffee, a complete mechanical or manual Beerntung in only one processing step can be made. $5 DurehAnwendung vonWaehstumsregulatoren can also Samenoder bud peace plants, thus endogenous Jahresrhythmik, affected, so that the plants, how e.g. pineapple or ornamental plants germinates, drives out or flowers in market gardens, at one time, at which normalerweisehiezukeine readiness show it. With Waehstumsregulatoren it can be also achieved that drove out by buds or those germinating of seeds one retards to e.g. avoid in order in frostgefä'nrdeten areas a damage by late frosts. Waehstumsregulatoren can produce also a HalophiIie with cultivated plants. Thus the conditions for are created that a Kultiviernng can be accomplished by plants on salzhaltigen grounds. M_it growth modulators can be induced also Frostund drying resistance with plants. Those according to invention einzusetzendea active substances can be transferred into the usual formulations, like solutions, emulsions, suspensions, powders, pastes and granulates. These are manufactured in well-known way, e.g. ° by mixing the active substances with Streekmittein, thus liquid solvents, under pressure standing liquefied gases and/or firm carrier materials, if necessary using oberfläehenaktiven means, thus emulsifying means and/or dispersing agents and/or foam-producing 1Vli teln. In case of the use of water as stretching means e.g. also organic solvents can be auxiliarysolvent-used as. As liquid solvents are essentially applicable: Aromatics, like xylene, toluol, benzene or alkyl naphtha LINE, atomic ones or chlorinated aliphatic hydrocarbons, like chlorine benzene, chlorine ethylens or dichloromethane, aliphatisehe Kohlenwasserstofle, like Cyelohexan or paraffins, ehlorierte e.g. Erdöifraktionen, alcohols, like butanol or glycol their ether and ester, Ketone, like Aeeton, Methylä ylketon, Methylisobutylketon or CyeIohexanon, strongly polar solvents, like dimethylformamide and Dimethylsulfoxyd, as well as water; with liquefied gaseous Streckmittela or carrier materials such liquids are meant, yield at normal temperature and under normal print gaseously are, e.g. Aeroscl propulsion gases, like Diehlordifluormethan or Triehlorfluormethan; as firm of carrier materials: natural Gestsinsmehle, like Kaoline, aluminas, talcum powder, chalk, quartz, Attapulgit, l Iontmorillonit, or Dlatomeenerde, and synthetic powdered minerals, like hochdisperse silicic acid, Alumininmoxyd and silicate; as emulsifying means: nichtionogene and anionische Emulgntoren, like Polyoxyäthylen fatty acid esters, Pclyoxyäthylen Fettalkohol ethers, e.g. alkyl aryl polyglykol ethers, Alkylsulfonate, alkyl sulfates and Arylsulfonate; as D spergiermitteh e.g. lignin, Sulfitablaugenund MethFlcellulose. The active substances can be present in the formulations in mixture with other well-known active substances, like fungicides, fnseldizide, Akarizide and herbicides, as well as in mixture with fertilizers. The formulations contain generally between 0,1 and 95 Gew. - Active substance, preferably I0 between 0, 5 and 90 Gew. - %. The active substances can be used as such, in form of their formulations or the application forms, like ready for use solutions, prepared from it, smulgierbare concentrates, emulsions, foams, Suspensichert, Spritzpulver, pastes, soluble powders, Stäuhemittel and granulates. Application is done in usual way, e.g. via pouring, spraying, spraying, scattering, types of dust, foamings, to coat or dieWirkstoffzubereiümg or denWirkstoff even into the ground inject Begasen etc. it is possible furthermore to yield the active substances in the Ultra Low volume procedure plants or plant parts with the active substance preparation or the active substance. Also the seeds of the plants can be treated. The Wirkstoffkonzentraßoneu can do within a larger range varies werden.lm general used one concentrations from 0,00005 to 2%, preferably ven 0, 0001 to 0,5%.Ferner turns one generally per hectare of floor space 0.01 to 50 kg, prefers 0, 05 to 10k active substance on. For the Anweadungszeit it is valid that the application of the Wachshlmsregulatoren in a preferential period is made, whose exact demarcation depends on the climatic and vegetative Gegebenheitsn. The materials which can be used according to invention exhibit not only very good plant growth-adjusting characteristics, but possess beyond that also fungicides effectiveness. They are suitable e.g. to fighting against Apfelschorf. In the following examples those activity of the materials which can be used according to invention is represented as growth modulators, without to-locking the possibility of further application than Wachstumsregnlatoren. Example 1: Stature inhibition/beans solvents: 10 Gew. - Parts methanol emulsifying agent: 2 Gew. - Parts of PL Sorbitan Monolaurat for the production of one zweckmäßigenWirkstoffzubereiümg one mixes 1 Gew. - TeiI active substance with the indicated quantities of solvents and emulsifying agent and fills up with water to the desired concentration. Young Botmenpflanzen is dripping wet sprayed in the stage, in which the primary sheets are fully unfolded, with that Wirkstoffzubereiümgen. After 2 weeks the increase is measured and the stature inhibition in o of the increase of the control plants is computed. 100% the stop of the Wachsamst and 0% a Wachstam mean according to that the untreated Kontrolipflanzen. Active substances, active substance concentrations and results come out from the following table A: Table A stature inhibition/beans i active substance - (control) CHSN numerical control 2 H25 (I) 70% CH3N NC8 HIz \ __/30% CHS - N N \/ -- Ci0 H21 (i,) CH3 J \ - numerical control H \/n 2 (5) CHS - N N \/- C to hands 35 (7) CHS - N n/Cis H27 Wi rkstoffkonzentration in % 0, 05 O, 05 0.05 O, 05 0, 05 stature inhibition in % of control of B0 B e i s pi e 1 2: Stature inhibition with chrysanthemums solvents: 10 Gew. - Parts methanol emulsifying agent: 2 Gew. - Parts of PL Sorbitan Monolaurat for the production of an appropriate Wirkstoffzubereiümg one mixes 1 Gew. - Partial active substance with the indicated quantities of solvents and emulsifying agent and fills up with water to the wishing concentration. Chrysan hemensteekllnge of approximately 10 cm height, are dripping wet sprayed with the active substance preparations. As soon as the untreated control plants reached a Wuehshöhe of approximately 40 cm, the increase is measured with all plants and the stature inhibition in % of the increase of the control plants computes. 100% the stop of growth and 0% a Waehstum mean according to that of the untreated control plants. Active substances, active substance concentrations and results come out from the following table B. Table B stature inhibition with chrysanthemums active substance - (control) clcE - - (admits) H3C - N n \ _j C 2 H25 C1C) Wirkstoffkonzenoration in % 0.10 stature inhibition in % of control of 0.10 lO0 B egg s pi e i 3: Stature inhibition with soy beans solvents: 10 Gew. - Parts methanol emulsifying agent: 2 Gew. - To active substance-preparation-mix parts of PL Sorbitan Monolaurat ZurHerstellung of an appropriate one 1 Gew. - Part active substance with the indicated quantities of solvents and emulsifying agent and fills up with water to the desired concentration. Young soy bean plants are dripping wet sprayed in the stage, in which the first Folgoblätter is unfolded, mitden Wirkstoffzubereiümgen. After 2 weeks the increase is measured and the stature inhibition in % of the increase of the Kontrollpflauzen is computed. 100% the stop of growth and 0% a growth mean according to that of the untreated control plants. Active substances, active substance concentrations and results come out from the following table C. Table C stature inhibition with soy beans active substance - (control) c1-- CH2 - Ct {2 - N (CH3) 3 c1 0 admits) of /w \ eH3_. /Nc14 (9) CHùN! --XN - CH = CH (s) of CH3 - N n/C0 Hi9 CH3 - N NCio H21 - H CH3 _/N -- Ci1 23 (lo) Wirkstoffkonz entration in % 0, 05 0, 05 0, 05 O, 05 stature inhibition in % of control of 9O B e i s p i e 1 4: Inhibition of the growth of side impulses with tobacco solvent: 10 Gew. - Parts methanol emulsifying agent: 2 Gew. - Parts of PL Sorbitan Monolaurat ZurHerstellung of one zweokm£ßigenWirkstoffzubereitung one mixes 1 Gew. - Part active substance with the indicated quantities of solvents and emulsifying agent and fills up with water to the desired concentration. The branch points of approximately 50 cm high tobacco plants are broken off. On the following day the plants with the Wirkstoffzubereiümgen are dripping wet sprayed. After 3 weeks become the side impulses, which see during this time to have formed, herausgebroehen. The entire side impulses of a treatment are weighed. The weight of the side impulses of the treated plants is compared with that the untreated control plant. Mean 100% inhibition the absence of side impulses and 0% a Waehstum according to that of the control plants. Active substances, active substance concentrations and results come out from the following table D. Table D inhibition of the growth of side impulses with tobacco active substance - (control) CH3 - N numerical control H \ ___/12 (1) m % CH3 - N n \ ____/C8 REAR ONE? /-- \ i 30% CH3 - N \ __/NC10 (11) m CHs n pCn H23 ¢5) CHS - N n _/C s H27 (6) Wirkstoffkonzentraßon in % 0, 0B 0.20 O, 05 O, O, 05 O, O, inhibition of the side growth of sprout in % of control of 38 86 manufacture before s chriften: 1) H3 C - N n - CHS \ __/(CHB) ii 100 g (1 mol) 1-Methylpiperazin are heated up to 100°C and shifted in three portions with altogether 204, 5 g (2 mol) Dodecylchlorid. After 15minütiger Reaktfensdauer one gives firm sodium hydroxide in several portions to 40 g (1 mol) in addition and lets 2 h with 140 bis150°C react. Subsequently, one separates the reaction product from the firm inorganic arrears, by filtering the Reakfionsgemisch hot. One extracts the inorganic arrears twice with ever 200 ml benzene, separates the benzene phase, restricts and adds the arrears verb-borrowing thereby to the main filtrate. The Produktwirdeinerfraktäonierten Destillatäon subjected. One receives in this way 177 g (66% of the theory) at 1-Methyl-4-dodecyl-piperazin from the boiling point 90 to 115°C with 0, 01 Terr. 2) /m \ H C-N n (CHe) S-CHS s _/100 g (1 mol)! - Methylpiperazin and 176, 5 g (1 mol) Decylchlorid are heated up at an outside temperature of 150°C so for a long time unterl ü kfluß, until simmering of the Reaktionsgemisehes is terminated. After the cooling the firm product with a mixture from 40 g (1 mol) is out-vibrated sodium hydroxide in 500 mI water and 500 ml to ISO butanol. One separates the organic phase, confines and-extracts the arrears remaining thereby also petroleum ether after the evaporation of the petroleum ether solution receives one 180 g (75% of the theory) at 1-Methyl-4-decyl-piperazin in dürmschichtchromatographisch pure form. The IR spectrum of the l of saktiensproduktes show no NH-gang. In the mass spectrum the molecule peak appears with m/e = 240. n 0= 1, to 4595 NP'0 1 = 110 to 115°Co iä the following table 1 in the regulations 3 to 7 specified connections in appropriate way in the procedure (A) are received. Table 1 HsC n 2-E regulation and/or connection No. 3 4 6 7 example 8: R2 -- (CH2) 7 -- Ctt3 - (CH2) s - CHs -- (CH2)! 0 CH3 - (CH) 2 - CH -- (CH2)! 6 - CPI3 Brechungsind NO 1, 4592 1.4868 1, 4597 boiling point kp. in °C Sehmelzpunkt Fp. Kp. = 110 et/0, 3 torr of kp. = 115eC kp. = 115eC/0,1 peat Fp.= 20 ms 25ec Fp. = 58°C H3C-N n (CH2) 9-CH=CH2 \ __/a solution of 34, 6 g (0, 13 mol) Undec-10-en-säure (4-methyl) - plperazidid in 150 ml absolute tetrahydrofurane into a suspension by 5, 7 g (0, le mol) IAthiumalanat in 150 is introduced in drops ml absolute tetrahydrofurane. After terminated addition that is heated up lqeaktionsgemisch 8 h under lqückfluß. To the Aufarbeituag one lets the Beaktionsgemiseh up tree temperature cooling, drips then successively 6 ml to water, 6 ml one 15%igen aqueous sodium hydroxide solution and 18 ml water under agitating in addition. Subsequently, one sucks the failed precipitation off, washes the Filtcrrückstand with tetrahydrofurane and restricts the filtrate. The arrears remaining thereby are extracted with petroleum ether. Afterwards mau the Petrelätherphase separates and distills the solvent off. One receives in this way 26, 2 g (80% of the theory) at 1-NIethyl-4-undec-10-enyl-piperazin in form of a colorless oil. In the IR spectrum of the product no more appears the broad, strong amide gang at 1640 cm-1, but a narrow, sharp gang with same Wellenzahl, which suggests the presence of a oleflnischen double bond. The mass spectrum shows the molecule peak with m/e = 252. Analysis: Computed: N= 11.1% found: N = II, 2%. The purity of the insulating product lets itself confirm dünnschichtehromatographisch in simple way. Representation of the output product: C - \ Inc. (cHpù - cù: eHù o - 12 - Nr°339930 into a solution of 110 g (1.1 mol) 1-Methyl-piperazin in 600 ml ISO butanol with 0 to 10 degrees under agitating 202, 5 g (1 mol) Undec-10-ensäurechlorid introduced in drops for the transformation thereby of the developing salt into free and EN 10-EN acid (4-methyl) - piperazidid one vibrates the Beaktionsgemisch with 0°C with an aqueous well iumhydroxydlösung, which contains 40 g (1 mol) sodium hydroxide. Subsequently, the organic phase is separated and restricted. After the drying process with a pressure of 0,1 peat and at a temperature of 100°C one receives the Undec! 0-en-säure (4-methyl) - piperazidid as dünnschichtchromatographisch pure product in nearly quantitative yield. The IR-Spetdrum of the product points a strong tertiary amide gang! 640 cm-i up. = 1, 4882. Regulation 9: /m \ H3 C - N n - CHS \/(CH2) is in 8 procedures described in example becomes by Beduktionvon Myristinsäure (4-methyl) - - piperazidid the 1-Methyl-4etradecyl-piperazin received as product from the boiling point 140 bis1450C with 0,1 torr. nE= 1, 4638. The Myristinsäure (4-methyl), needed as Ausgangspredukt - piperazidid according to the method indicated in the example 8 by conversion from Myristinsäurechlorid with 1-Methyl-piperazin one receives. Fp. = 33 to 34°C. 10) in \ the CHS - N numerical control H \/s Is/numerical control H CH3 - N CHS -- N NO H mixture in inBeispiel 8 descriptive procedures will receive by Bedukäon from “Versaticsäure-911” - (4-methyl) - piperazidid, a mixture above of the by formula designated Piperazine. ni O= 1, 4652 as output problem needed “Versatiesäure-91! ” - (4-methyl) - piperazidid becomes according to the method indicated in the example 8 by conversion of “Versaticsäure-911” - chloride with 1-Methyl-piperazin receive. Kp. = 125 to 135°C/0, 2 torr. 11) 3°-d \ t numerical control H (o%) \ i 8 IY mixture /-- \ (30%) Hs C -- N \ __/C! o H2 after i in Beispie! 8 descriptive procedures becomes by Reduktien of Kokosfettsäure (4-methyl) - - piperazidid a mixture above of the by formula designated Piperazine received. Kp. = 105 to 115°C/0, 2 torr of n = 1, 4590. Necessary Kokesfettsäure (4-methyl) aIsAusgangsprodukt - piperazidid mixture erhältman by the fact that one vonKekesfettsäuren with the Destillaßon as advance resulting mixture treated with Thionylchlorid and the product isolated thereby then according to the method described in the example 8 with 1-Methyl - piperazin converts. The IR spectrum of the product isolated in form of an oil shows an intensive gang of a tertiary - I of amide with 1640 cm