CS256566B1 - A method of producing a plant growth stimulator and / or regulator - Google Patents

A method of producing a plant growth stimulator and / or regulator Download PDF

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CS256566B1
CS256566B1 CS851381A CS138185A CS256566B1 CS 256566 B1 CS256566 B1 CS 256566B1 CS 851381 A CS851381 A CS 851381A CS 138185 A CS138185 A CS 138185A CS 256566 B1 CS256566 B1 CS 256566B1
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butyrolactone
regulator
chlorination
plant growth
stimulator
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CS851381A
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Czech (cs)
Slovak (sk)
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CS138185A1 (en
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Vendelin Macho
Jozef Hudec
Frantisek Halmo
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Vendelin Macho
Jozef Hudec
Frantisek Halmo
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Priority to CS851381A priority Critical patent/CS256566B1/en
Priority to CS872938A priority patent/CS261190B1/en
Priority to CS872937A priority patent/CS293787A1/en
Publication of CS138185A1 publication Critical patent/CS138185A1/en
Priority to CS877136A priority patent/CS261449B1/en
Publication of CS256566B1 publication Critical patent/CS256566B1/en

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Abstract

Stimulátor a/alebo regulátor rastu rastlín na báze organických halogénzlúčenín sa vyrába substitučnou katalytickou alebo nekatalytickou chloráciou ^-butyrolaktónu pri teplote 80 až 200 °C až do dosiahnutia indexu lomu nD25 = 1,4700 až 1,4780 (1,4755 až 1,4760. Z produktu chlorácie sa oddělí chlorovodík a připadne neskonvertovaný χ-butyrolaktón a/alebo sa produkt chlorácie zmydelní alebo neutralizuje zlúčeniou alkalického kovu. Sposob je vhodný pre výroby biologicky aktívnych látok v chemickom priemysle.A plant growth stimulator and/or regulator based on organic halogen compounds is produced by substitution catalytic or non-catalytic chlorination of χ-butyrolactone at a temperature of 80 to 200 °C until a refractive index nD25 = 1.4700 to 1.4780 (1.4755 to 1.4760) is reached. Hydrogen chloride and possibly unconverted χ-butyrolactone are separated from the chlorination product and/or the chlorination product is saponified or neutralized with an alkali metal compound. The method is suitable for the production of biologically active substances in the chemical industry.

Description

256566256566

Vynález sa týká výroby stimulátora aleboregulátora rastu rastlín, resp. výroby účin-ných komponentov stimulátorov alebo re-gulátorov rastu na báze organických halo-génzlúčenín, s využitím substitučně] chlo-rácie. V polnohospodárskej a lesnej praxi sa uždávnejšie úspěšně aplikujú mnohé zlúčeni-ny ako fyziologicky účinné látky typu auxi-noidov, kinínov i retardantov napriek tomu,že biochemická podstata ich posobenia jestále ešte predmetom různých hypotéz [Au-dus J. J.: Plant Science Monographs. Lon-don-New York (1963); Turecka R. Ch., Po-lykarpova F. Ja.: Vegetatiinnoe rozmnože-nie rasteni] s primeneniem stimulátorovrosta, Moskva (1966)]. Přitom rastové re-gulátory majú rožne štruktúry [Appel P.,Natr. L.: Biochem Physiol. Pfl. 1976, 169;Wegler R.: Chemie der Pflanzenschutz undShadlingsbekámpfungsmittel, Band 4. Sprin-ger Verlag, Berlin-Heidelberg-New York(1977)]. Známa ]e kyselina jantárová akostimulátor rastu rastlín a vysvetlenie bio-chemického účinku pQsobenia pomocoukvantovej biochemie [Blagoveščenski] A. V.,Rachmanov R. R.: Jantarnaja kislota i povy-šenie urožaev, Taškent (1966); Blagoveščen-skij A. V., Rachmanov R. R.: Biochimičeska-ja príroda povyšenija urožajnosti s pomoš-čju jantarno] kisloty. Izdatefstvo Moskovs-kogo Gusudarstvennogo Universiteta, Mos-kva (1970)], ako a] organické kaly z ano-dické] oxidácie hliníka, obsahujúce hlavněkyselinu jantárovú (čs. autorské osvedče-nie 229 411). Ďalej maleínanhydrid, kyseli-na maleinová, je] soli i estery (čs. autor-ské osvedčenie 226 318), ako a] vedfajšieprodukty z výroby cyklohexanónu oxidácioucyklohexánu (čs. autorské osvedčenie220 936 ap.). Účinným rastovým regulátoremmá byť a] dichlórizomaslová kyselina a jejsoli (USA pat. 2 823 232), pričom známy jea] spůsob je] přípravy (Prieber: Bull. Soc.Chem. France 1954, str. 199).The present invention relates to the production of a plant growth stimulator and a plant growth regulator, respectively. the production of active components of stimulators or growth regulators based on organic halogens, using substitution chlorination. Many compounds such as physiologically active substances such as auxinides, kinins and retardants have been successfully applied in agricultural and forestry practice, despite the fact that the biochemical nature of their activities is still subject to various hypotheses [Au-J.J.J. Plant Science Monographs. Lon-don-New York (1963); Turkey R. Ch., Po-Lykarpova F. Ja .: Vegetatiinnoe Growth] with Stimulation of Stimulators, Moscow (1966)]. Here, growth regulators have spit structures [Appel P., Natr. L .: Biochem Physiol. Pfl. 1976, 169; Wegler R .: Chemie der Pflanzenschutz und Shadlingsbekamffungsmittel, Band 4. Sprinter Verlag, Berlin-Heidelberg-New York (1977)]. Succinic Acid Growth Growth Acid is known and an explanation of the biochemical effect of the effect of quantum biochemistry [Blagoveshchenski] A.V., Rachman R.R .: Jantarnaya kislota i povyusi urozaev, Tashkent (1966); Blagoveshchenskij A. V., Rachman R. R., Biochimicheska-ja priroda povysenija urozajnosti s pomos-cju jantarno] kisloty. Izdatefstvo Moskovs-kogo Gusudarstvennogo Universiteta, Moskva (1970)], as and] organic slurries from the a-dical] oxidation of aluminum, mainly containing succinic acid (Czechoslovakia Certificate No. 229 411). Further, maleic anhydride, maleic acid, is both salts and esters (U.S. Pat. No. 226,318), as well as byproducts from the production of cyclohexanone oxidation cyclohexane (Czechoslovakia Certificate 220 936, etc.). An effective growth regulator is α] dichloroisobutyric acid and its salts (U.S. Pat. No. 2,823,232), which is well known in the art (Prieber: Bull. Soc. Chem. France 1954, page 199).

Uvedené i ďalšie známe regulátory a sti-mulátory rastu rastlín sú zaujímavé, čorazvačšmi nachádzajú uplatnenie v praxi, alepochopitelné, ešte stále v dostatočne] mie-rc neriešia potřeby intenzívnej polnohospo-dárskej rastlinnej výroby a pestovania le-sov. A tak sortiment účinných stimulátorova regulátorov rastu rastlín sa rozšiřuje ocfalšie, spůsobom výroby podlá tohto vyná-lezu. Pódia tohto vynálezu sposob výroby sti-mulátora a/alebo regulátora rastu rastlínako aj účinných komponentov stimulátorova/alebo regulátorov rastu, na báze hlavněorganických halogénzlúčenín sa uskutečňu-je tak, že χ-butyrolaktón sa substitučně ne-katalyticky alebo katalyticky chlóruje priteplote 80 až 200 °C až do dosiahnutia inde-xu lomu nD25 = 1,4700 až 1,4780, výhodné1,4755 až 1,4760. Z produktu chlorácie saoddělí chlorovodík a připadne neskonver- tovaný χ-butyrolaktón a/alebo sa produktchiorácie zmydelní a/alebo neutralizuje zlú-čeninou alkalického kovu, s výhodou uhli-čitanom alebo hydrouhličitanom. Výhodou spůsobu výroby stimulátora a/a-lebo regulátora rastu rastlín pódia tohto vy-nálezu je realizovatelnost v jednom tech-nologickom stupni s dobrými výťažkami,dokonca na typovom zariadení. Nevyžadujesi náročnň izoláciu. Potom surovinová do-stupnost, nízká energetická náročnost aprakticky bezodpadovosť celého procesu.These and other well-known plant growth regulators and stabilizers are of interest; they find their application in practice, but they are still not sufficient to meet the needs of intensive agricultural crops and lees. Thus, the range of potent plant growth stimulator regulators is expanding more frankly, according to the invention. According to the present invention, a process for the production of a stabilizer and / or a growth regulator for plants and effective growth stimulator / regulator components based on mainly organic halogen compounds is carried out in such a way that ω-butyrolactone is substituted or unatalystically catalytically chlorinated at 80 to 200 ° C until the refractive index nD25 = 1.4700 to 1.4780, preferably 1.4755 to 1.4760. Hydrogen chloride is removed from the chlorination product and optionally unconverted ω-butyrolactone and / or the productification is saponified and / or neutralized with an alkali metal compound, preferably carbonate or bicarbonate. An advantage of the method of producing the plant growth stimulator and / or the plant growth regulator of the present invention is the feasibility in one technological stage with good yields, even on a type plant. You do not require heavy insulation. Then the raw material availability, the low energy demand and the virtually waste-free process.

Produktami chlorácie χ-butyrolaktónu súhlavně a-chlór-y-butyrolaktón, a,a‘-dichlór--/-butyrolaktón, kyselina χ-chlórmaslová akyselina α,χ-dichlórmaslová. Z reakčnéhoproduktu je však vhodné izolovat a recirku-lovať nezreagovaný χ-butyrolaktón. Neutra-lizáciou alebo zmydelnením produktov chlů-rácie, či už uhličitanmi alebo hydrouhliči-tanmi alkalických kovov alebo pri nižšíchteplotách aj hydroxidmi alkalických kovov(je třeba dbát, aby nedošlo k dechlorácii,či k dehydrochlorácii produktov chlorácieχ-butyrolaktónu] vznikájú příslušné alkalic-ké soli. Tie podobné, ako prvotné produktychlorácie možno aplikovat vo formě rozto-kov, najma zriedených vodných roztokov okoncentrácii 1 . 10~3 až 1 . 10~5 = hmot.,ale tiež vo formě disperzií, emulzií, připad-ne spolu s inými organickými látkami, pes-ticídmi, hnojivami, zvlášť kvapalnými ap.Možno ich aplikovat' aj rozprašováním lensamotných účinných komponentov; vhodnéich je spájat s aplikáciou pesticídov, hnojívalebo konzervantov. Na impregnáciu zrna vpríprave osiv, sa móže aplikovat dokoncaaj vo formě prášku, pričom k impregnáciidojde vlastně až v půdě po zasiatí. Vhodnéje přitom využívat nezanedbatelný účinokstimulátora a/alebo regulátora rastu rastlín. V prípadoch katalytickej chlorácie χ-bu-tyrolaktónu sa používajú obvyklé haloge-načné katalyzátory, ako sú Lewisove kyse-liny, ale tiež oxid antimonitý, chlorid anti-monitý ap. Z produktu chlorácie je vhodnéoddělit chlorovodík, ktorý by sťažoval ma-nipuláciu so stimulátorom, resp., reguláto-rem rastu, sposoboval koróziu ap. Produktchlorácie možno připadne stabilizovat, na-příklad přísadou 1 až 3 % močoviny alebohexymetyléntetraamínu.Chlorination products of ω-butyrolactone are mainly α-chloro-γ-butyrolactone, α, α-dichloro-β-butyrolactone, ω-chlorobutyric acid and α, ω-dichloromethane. However, unreacted γ-butyrolactone is preferably isolated and recirculated from the reaction product. By neutralization or saponification of the chlorination products, whether alkali metal carbonates or bicarbonates, or with lower temperatures, alkali metal hydroxides (care must be taken to avoid dechlorination or dehydrochlorination of the chloro-butyrolactone chlorination products), the corresponding alkali salts are formed Those similar to the primary products of chlorination may be applied in the form of solutions, in particular dilute aqueous solutions, by concentrating from 1 to 10 -5% by weight, but also in the form of dispersions, emulsions, optionally together with other organic substances. They can also be applied by spraying lens-active active ingredients, suitable to be combined with the application of pesticides, fertilizers or preservatives.For impregnation of the seeds in seed preparation, they can be applied in the form of a powder, in fact in the soil after sowing činokstimulátora and / or plant growth regulators. In cases catalytic chlorination χ-butyl tyrolaktónu using conventional halogenating catalysts such as Lewis KYSE oxyacid, but also antimony trioxide, antimony trichloride ap. From the chlorination product, it is appropriate to separate the hydrogen chloride, which would make it difficult to handle the stimulator, respectively the growth regulator, to cause corrosion and the like. Optionally, the chlorination products can be stabilized, for example by the addition of 1 to 3% of urea or hexymethylenetetraamine.

Pri zmydelňovaní produktu chlorácie jetřeba dbát, aby nedošlo z něho k odštiepe-niu chlóru. Preto je vhodné neutralizovat azmydelňovať produkt chlorácie pri teplote0 až 50 °C.In the case of saponification of the chlorination product, care must be taken that chlorine is not removed. Therefore, it is desirable to neutralize and saponify the chlorination product at 0 to 50 ° C.

Spůsob výroby podl'a tohto vynálezu jemožné uskutečňovat diskontinuálne, polo-pretržite alebo kontinuálně. Neskonverro-vaný χ-butyrolaktón je vhodné recyklovat. Ďalšia charakteristika sposobu výroby aužitkových vlastností stimulátora a/aleboregulátora rastu rastlín, vrátane dřevin jezřejmá z príkladov.The process of the invention can be carried out discontinuously, semi-continuously or continuously. Unconverted χ-butyrolactone should be recycled. Another characteristic of the method of producing and utilizing the properties of the plant growth stimulator and / or regulator, including woody plants, can be seen from the examples.

25B5BB 6 Příklad 125B5BB 6 Example 1

Podlá známej metodiky [A. Murina a íní:Biológia 35, 937 (1980)] sa stanovuje klíči-vost a dížka korienkov kukuřice odrody TO440 a podl'a metodiky Hojčuša [R. Hojčuš ainí: Návody na cvičenia z fyziologie rastlín,Příroda, Bratislava (1981)] klíčivost a díž-ka hypokotylu jarného jačmeňa odrody O-pál v závislosti od koncentrácie vodnéhoroztoku chlórovaného χ-butyroiaktónu. Sa-motný chlórovaný χ-butyrolaktón má totozloženie (v % hmot.): a-chlór-y-butyrolak-tón — 26,4; a,a‘-dichlór-y-butyrolaktón ~12,7; χ-butyrolaktón — 12,6; α,χ-dichlór-maslová kyselina = 31,4; χ-chlórmaslovákyselina = 13,4. Získané výsledky sú zhr-nuté v tabulke 1 a sú aritmetickým prisme-rom troch opakovaní. Súčasne sa v trojtýž-dennom pokuse pod světelnou rampou s po-dobnými variantami preveruje účinok vodného roztoku chlórovaného χ-butyrolaktó-nu. Postupuje sa tak, že do malých nádob s obsahom po 200 g zeminy a 200 g přepra-ného křemičitého piesku s rovnakým hno-jením sa vyseje po 30 zrn jarného jačme-ňa Opál a po vzídení sa vyjednotí na početdc 20 rastlín. Zrno sa použije ako také mo-řené v destilované] vodě (kontrola) alehomořené vo vodných roztokoch chlorované-ho χ-butyrolaktónu roznej koncentrácie. Mo-ří sa 50 g zrna v 60 cm3 vodného roztokupočas 24 h. V tých variantoch, kde zrno ne-bolo mořené, aplikuje sa na rastliny po 7dňoch od vzklíčenia postrek roztokmi chlo-rovaného χ-butyrolaktónu roznej koncen-trácie, ako aj neutralizovaného v dávke 5cm3 na nádobu. Každý variant má 4 opako-vania. Dosiahnuté výsledky zhrnuté v ta-buTke 1 sú aritmetickým priemerom získa-ných hodnot. Statistické zhcdnotenie sa ro-bí analýzou variantnosti. Ako optimálna zhlediska klíčivosti zrn, dlžkv korienkov, a-ko aj hypokotylu je koncentrácia roztoku3 . 10"3 % hmot.According to the known methodology [A. Murina et al.: Biology 35, 937 (1980)] identifies the keyness and length of the corn root of the TO440 variety and according to the Hojčuš [R. Hojčuš ainí: Instructions for Exercises in Plant Physiology, Nature, Bratislava (1981)] germination and the length of the spring barley of barley O-pál variety depending on the concentration of the aqueous solution of chlorinated χ-butyroiactone. The chlorinated ω-butyrolactone alone has the following composition (in% by weight): α-chloro-γ-butyrolactone - 26.4; α, α-dichloro-γ-butyrolactone ~ 12.7; χ-butyrolactone - 12.6; α, ω-dichloro-butyric acid = 31.4; χ-chlorobutyric acid = 13.4. The results obtained are summarized in Table 1 and are the arithmetic ratio of three replicates. At the same time, the effect of an aqueous solution of chlorinated ω-butyrolactone is examined under a light ramp with similar variants in a three-week experiment. In this way, 30 grains of spring Opal barley are seeded in small containers containing 200 g of soil and 200 g of powdered quartz sand with the same spreading, and after emergence, they are seeded in a number of 20 plants. The grain is used as such in distilled water (control) but in aqueous solutions of chlorinated ω-butyrolactone of varying concentration. 50 grams of grain in 60 cm 3 of aqueous 24-hour spinning time are possible. In those variants where the grain has not been pickled, sprayed solutions of chlorinated ω-butyrolactone of various concentrations as well as neutralized by application are applied to the plants 7 days after sprouting. 5 cm 3 per container. Each variant has 4 repetitions. The results obtained in Table 1 are the arithmetic mean of the values obtained. Statistical analysis is followed by a variance analysis. The optimal concentration of germination, root length, and hypocotyl is the concentration of the solution. 10 "3 wt.

Tabulka 1Table 1

Druh a koncentrácia vodného roztokuf°/o hmot.]Type and concentration of aqueous solution (w / w)

Hmotnost nadzemnejhmoty jarného jačmeňa — sušina [%] zrno mořené postrek porastuWeight of barley spring weight - dry matter [%] grain pickled crop spray

Kontrola (destilovaná voda) 100,0 — Kyselina a-naftyloctová o konc. 3 . 10-3 % 115,7 115,1 o konc. 3 . 10 _4 % 111,1 110,8 Vodný roztok chlórovaného χ-butyrolaktónu o koncentrácii 3 .10-1% 89,7 90,9 3.10"2 % 106,0 105,1 3.ΙΟ’3 % 126,6 128,4 3 . 10“4 % 118,2 120,7 3 . 10"5% 124,6 125,0 Preukaznosť P 0,05 14,54 rozdielov P 0,01 19,44 2SSS68Control (distilled water) 100.0 - α-Naphthylacetic acid conc. 3. 10-3% 115.7 115.1 o conc. 3. 10 _4% 111.1 110.8 Aqueous solution of chlorinated χ-butyrolactone at a concentration of 3.10-1% 89.7 90.9 3.10 "2% 106.0 105.1 3.ΙΟ3% 126.6 128, 4 3 .10 "4% 118.2 120.7 3.10" 5% 124.6 125.0 Evidence P 0.05 14.54 Differences P 0.01 19.44 2SSS68

Variant Končen- Úroda zrna Úroda slamy Počet Hmotnost 1000 Úroda sena trácia [°/o] L%] produktívnycň zrn (HTZ) [%] [% odnoží [%] hmot.] 1983 1984 1983 1984 [%]Variation - Harvest of grain Harvest of straw Number Weight 1000 Harvest of hay Throw [° / o] L%] Productive grains (HTZ) [%] [% offshoots [%] weight] 1983 1984 1983 1984 [%]

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Claims (2)

1. Spósob výroby stimulátora a/alebo regulátora rastlín, ako aj účinných komponentov stimulátorov a/alebo regulátorov rastu, na báze hlavně organických halogénzlúčenín, vyznačený tým, že χ-butyrolaktón sa substitučně nekatalyticky alebo katalyticky chlóruje pri teplote 80 až 200 °C až do dosiahnutia indexu lomu nD 25 = 1,4700 až 1,4780, s výhodou 1,4755 až 1,4760, zProcess for the production of a stimulator and / or a plant regulator as well as active components of a stimulator and / or a growth regulator, based mainly on organic halogen compounds, characterized in that χ-butyrolactone is substituted non-catalytically or catalytically chlorinated at 80 to 200 ° C reaching a refractive index n D 25 = 1.4700 to 1.4780, preferably 1.4755 to 1.4760, z YNÁLEZU produktu chlorácie sa oddělí chlorovodík a připadne neskonvertovaný χ-butyrolaktón a/alebo sa produkt chlorácie zmydelní a/alebo neutralizuje zlúčeninou alkalického kovu.According to the invention of the chlorination product, hydrogen chloride and optionally unconverted β-butyrolactone are separated and / or the chlorination product is saponified and / or neutralized with an alkali metal compound. 2. Spůsob podlá bodu 1, vyznačujúci sa tým, že neutralizácia sa převede s výhodou uhličitanom alebo hydrogénuhličitanom.2. Method according to claim 1, characterized in that the neutralization is preferably carried out with a carbonate or a bicarbonate.
CS851381A 1985-02-27 1985-02-27 A method of producing a plant growth stimulator and / or regulator CS256566B1 (en)

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CS851381A CS256566B1 (en) 1985-02-27 1985-02-27 A method of producing a plant growth stimulator and / or regulator
CS872938A CS261190B1 (en) 1985-02-27 1987-04-25 Plants' growth stimulator and/or regulator
CS872937A CS293787A1 (en) 1985-02-27 1987-04-25 Stimulator a/alebo regulator rastu rastlin
CS877136A CS261449B1 (en) 1985-02-27 1987-10-05 Plant growth stimulator and / or regulator

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CS851381A CS256566B1 (en) 1985-02-27 1985-02-27 A method of producing a plant growth stimulator and / or regulator

Publications (2)

Publication Number Publication Date
CS138185A1 CS138185A1 (en) 1987-09-17
CS256566B1 true CS256566B1 (en) 1988-04-15

Family

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Family Applications (4)

Application Number Title Priority Date Filing Date
CS851381A CS256566B1 (en) 1985-02-27 1985-02-27 A method of producing a plant growth stimulator and / or regulator
CS872938A CS261190B1 (en) 1985-02-27 1987-04-25 Plants' growth stimulator and/or regulator
CS872937A CS293787A1 (en) 1985-02-27 1987-04-25 Stimulator a/alebo regulator rastu rastlin
CS877136A CS261449B1 (en) 1985-02-27 1987-10-05 Plant growth stimulator and / or regulator

Family Applications After (3)

Application Number Title Priority Date Filing Date
CS872938A CS261190B1 (en) 1985-02-27 1987-04-25 Plants' growth stimulator and/or regulator
CS872937A CS293787A1 (en) 1985-02-27 1987-04-25 Stimulator a/alebo regulator rastu rastlin
CS877136A CS261449B1 (en) 1985-02-27 1987-10-05 Plant growth stimulator and / or regulator

Country Status (1)

Country Link
CS (4) CS256566B1 (en)

Also Published As

Publication number Publication date
CS293787A1 (en) 1988-05-16
CS713687A1 (en) 1988-06-15
CS261190B1 (en) 1989-01-12
CS138185A1 (en) 1987-09-17
CS293887A1 (en) 1988-06-15
CS261449B1 (en) 1989-02-10

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