CS250876B1 - Agent for encreasing the content of sugar - Google Patents

Agent for encreasing the content of sugar Download PDF

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CS250876B1
CS250876B1 CS755584A CS755584A CS250876B1 CS 250876 B1 CS250876 B1 CS 250876B1 CS 755584 A CS755584 A CS 755584A CS 755584 A CS755584 A CS 755584A CS 250876 B1 CS250876 B1 CS 250876B1
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Czechoslovakia
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inspection
methyl
hydrogen
alkyl
sugar
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CS755584A
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Czech (cs)
Slovak (sk)
Inventor
Viktor Sutoris
Vladimir Sekerka
Jan Halgas
Pavol Bajci
Vaclav Konecny
Stefan Varkonda
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Viktor Sutoris
Vladimir Sekerka
Jan Halgas
Pavol Bajci
Vaclav Konecny
Stefan Varkonda
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Application filed by Viktor Sutoris, Vladimir Sekerka, Jan Halgas, Pavol Bajci, Vaclav Konecny, Stefan Varkonda filed Critical Viktor Sutoris
Priority to CS755584A priority Critical patent/CS250876B1/en
Publication of CS250876B1 publication Critical patent/CS250876B1/en

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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

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Problém zvyšovania obsahu cukrov v rastlinách produkujúcich cukor je relativné rozpracovaný. Zvlášť bola v tomto smere věnovaná pozornost použitiu rastových stimulátorov. Obsah cukru v rastlinách produkujúcich cukor hol zvyšovaný aplikáciou auxiinoidov, ako:The problem of increasing the sugar content of sugar-producing plants is relatively solved. Particular attention has been paid to the use of growth promoters in this regard. Sugar content in sugar producing plants hol increased by application of auxiinoids such as:

kyselinou (S-inídolyloctovou (IAA), kyselinou jS-indolyl-y-maslovou (IBA) a kyselinou a-naftyloctovou na cukrovú řepu (Audus L. J.: Planí growth suhstances, Planí Science Monographs., London, New York, 1963, Willemont C.: 1960, Rev. d‘Oka, Montreal, 34, 5, Mitchell J. W., Martin W. E.: Bot. Gaz. 99, 569 (1937), Stuart N. W.: Bot. Gaz. 100, 298' (1938), Andrejeva R. A.: Udobr. i urožaj sv. 1, 8, 27—31 (1957) (a na obiloviny), Brunsetter B. G„ Myers A. T., Mitchell J. W„ Stewarrt W. S., Kaufman M. W.: Bot Gaz. 199, 268 (1948), Tomas 1. A., Atkims B. D., Ware S. M„ Bidwell R. G. S.: Can. Johr. Botany, 1 523 (1972)], giberelínov na cukrovú řepu [Kuli U.: Botamische Studien 19 (1972), Somfalvy E., Ausch K.: Kiserletugyi Kozlemények, 53, A, 1 (1900), Čkanikov D. I.: Agrochimija 3 (1971)], pšenicu [Brian P. W., Eleon G. W., Hemming H. G., Radley M., J. Sci. Food Agric. 5, 002 (1954)], kukuricu, hrách [Kuli U.: Botanische Studien 19 (1972)] a zemiaky [Lowell P. H„ Booth A.: New Phytol., 66, 4 (1967)].acid (S-inidolylacetic acid (IAA), β-indolyl-γ-butyric acid (IBA) and α-naphthylacetic acid for sugar beet (Audus LJ: Wild growth suhstances, Wild Science Monographs., London, New York, 1963, Willemont C) : 1960, Rev. d'Oka, Montreal, 34, 5, Mitchell JW, Martin WE: Bot Gaz, 99, 569 (1937), Stuart NW: Bot Gaz, 100, 298 '(1938), Andrejeva RA 1: 8, 27-31 (1957) (and for cereals), Brunsetter B.G. Myers AT, Mitchell J.W. Stewarrt WS, Kaufman MW: Bot Gaz. 199, 268 (1948) ), Tomas A., Atkims BD, Ware S. M. Bidwell RGS: Can. Joh. Botany, 1,523 (1972)], Gibberellins for sugar beet [Kuli U .: Botamische Studien 19 (1972), Somfalvy E ., Ausch K .: Kiserletugyi Kozlemenyek, 53, A, 1 (1900), Ckanikov DI: Agrochimija 3 (1971)], wheat [Brian PW, Eleon GW, Hemming HG, Radley M., J. Sci. 5, 002 (1954)], corn, peas [Kuli U .: Botanische Studien 19 (1972)] and potatoes [Lowell P. H. Boot h A .: New Phytol., 66, 4 (1967)].

Ďalej holi použité retardanty ako 1,2-dihydropyridazin-3,6-dion (tzv. hydrazid kyseliny maleinovej, MH) na cukrovú řepu [Kailirnin F. L., V. P. Jastrembovič N. J., Marežiskij J. G., Sarnaekaja V. V., MeíniČuh J. P.:Also used are retardants such as 1,2-dihydropyridazine-3,6-dione (maleic hydrazide, MH) for sugar beet [Kailirnin F.L., V.P. Jastrembovic N.J., Marežiskij J.G., Sarnaekaja V.V., Meinnihuh J.P .:

Regenerácia metabolizma rast. kletki, 61 (1973)] a zlúčeniny typu N-substituovaných oxobenzotiazolínov a oxabénzolínov (D* Amigo J. ].: US patent č. 4 227 915 (1978), Ref. Ž. Biol. 1981, 7 C, 426, D‘ Amigo L. J.: US patent č. 4 187 097 (1977), Ref.: Ž. Biol. 1980, 9 G, 290, D‘ Amigo J. J.: US patent číslo 4 149 871 (1977), Ref. Ž. Biol. 1979, 11 (II), 11G. 335).Regeneration metabolism growth. kletki, 61 (1973)] and compounds of the type N-substituted oxobenzothiazolines and oxabenzolines (D * Amigo J.] .: US Patent No. 4,227,915 (1978), Ref. Biol., 1981, 7C, 426, D. Amigo LJ: U.S. Patent No. 4,187,097 (1977), Ref .: J Biol 1980, 9G, 290, D Amigo JJ: U.S. Patent No. 4,149,871 (1977), Ref. 1979, 11 (II), 11G, 335).

V čs. AO č. 237 706 je chráněný prostriedok na zvyšovanie obsahu cukru obsahujúci ako účinná látku 3-R-substituovaný benzotiazóliumhalogenid vzorca (II)In MS. AO č. 237 706 is a protected sugar-enhancing agent containing 3-R-substituted benzothiazolium halide of formula (II) as active substance

R znamená metyl, alkyl, propargyl, benzyl, metoxykarbonylmetyl, etoxykarbonylmetyl, alyloxykarbonylmetyl, propargyloxykarbonylmetyl, izopropoxykarbonylmetyl,R is methyl, alkyl, propargyl, benzyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, allyloxycarbonylmethyl, propargyloxycarbonylmethyl, isopropoxycarbonylmethyl,

X znamená chlór, bróm a metosulfátovú skupinu.X is chlorine, bromine and metosulfate.

Teraz sa zistilo, že substituované benzotiazóliové soli všeobecného vzorca (I) •SsIt has now been found that substituted benzothiazolium salts of formula (I) • Ss

;.,Í ''N';., '' N '

0) v ktorom0) in which

R1 znamená alkyl Cl až Cio, allyl, propargyl cr2-RR 1 is alkyl Cl to CIO, allyl, propargyl, C-R 2 R

Y kdeY kde

-l2 znamená vodík, alkyl Ci až C3,-L 2 represents hydrogen, alkyl Cl to C3.

R3 znamená vodík, metyl, chlór,R 3 is hydrogen, methyl, chloro,

R4 znamená metyl, halogén, metoxy-, nitro-, kyano-, sulfonamido-, metoxysulfoskupion, naftylmetyl,R 4 represents methyl, halogen, methoxy, nitro, cyano, sulfonamido, methoxy sulfonyl, naphthylmethyl,

R5 znamená vodík, alkyl Cl až C4, alkyl, propargyl, beznyl,R 5 is hydrogen, C 1 -C 4 alkyl, alkyl, propargyl, beznyl,

R6 znamená vodík, metyl, halogén, metoxy-, nitro-, acetylamínoskupinu,R 6 represents hydrogen, methyl, halogen, methoxy, nitro, acetylamino,

R7 znamená vodík, metyl,R 7 is hydrogen, methyl,

R5 spolu s R7 a dusíkom připadne tvoříR 5 together with R 7 and nitrogen optionally form

5- alebo 6-členný heterocyklický kruh, připadne obsahujúci tiež atom kyslíka,A 5- or 6-membered heterocyclic ring, optionally containing an oxygen atom,

Y znamená kyslík, síru,Y means oxygen, sulfur,

Z znamená kyslík, síru, —NR7—, m znamená 0 až 2, n znamená 0 až 2, o znamená 1 alebo 2,Z is O, S, -NR 7 -, m is 0-2, n is 0-2, o is 1 or 2,

X znamená halogén, najma chlór, bróm, jód, CH3SO4, zvyšujú obsah cukru v rostlinách produkujúcich cukor.X is halogen, especially chlorine, bromine, iodine, CH 3 SO 4, increase the sugar content of sugar-producing plants.

Syntéza a struktura zlúčenín vzorca (I) je známa (Sutoris V., a kol., Chem. zvěsti 37, 653 /1983/, Halgaš J. a kol., Chem. zvěsti 37, 663 /1983/, Halgaš J. a kol., Chem. zvěsti 37,799 /1983/).The synthesis and structure of the compounds of formula (I) is known (Sutoris V., et al., Chem. Rumor 37, 653 (1983), Halgas J. et al., Chem. Rumor 37, 663 (1983), Halgaš J. and et al., Chem.

Zlúčeniny podta vynálezu je možné použit vo formě posťreku ako emulziu, suspenziu.a pod. za použitia organických rozpúšíadiel nereagujúcich s látkami podta vynálezu, výhodné za použitia vody v koncentrácii IQ-15 až 10_1 mól, s výhodou v rozmedzí 10'13 až 102 mól.The compounds of the invention may be used in the form of a spray as an emulsion, suspension, and the like. for solvents using organic non-responsive to the agents of the invention, preferably using water at a concentration of IQ -15 to 10 _1 moles, preferably in the range of 10 '13 to 10 2 mol.

Nasledujúce příklady objasňujú, ale neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the scope of the invention.

PřikladlEXAMPLE

Na oibrúsené semená cukrovej řepy, vyprané v tečúcej vodě (3 hodiny) bolo posobené v molárnych koncentráciácb skúmanými látkami 18 h. V osvettovanom kultivačnom boxe v perlíte bola vypěstovaná skupina rastlín. Před vlastným testováním hol počet rastlín zredukovaný na 5 rovnoměrných jédincov.For ground sugar beet seeds, washed in running water (3 hours), they were seeded at molar concentrations with the test substances for 18 hours. A group of plants were grown in an enlightened cultivation box in the nacre. Prior to testing, the number of plants was reduced to 5 even plants.

Po 10 dňoch kultivácie. bola vyhodnotená hladina cukrov v segmentoch listov modifikovanom metodou podta Kliku ),, Nováka V. a Gregora A.: Praktikum fytocenológie, ekologie, iklimatológie a pódoznalectva,After 10 days of cultivation. the level of sugars in leaf segments modified by the method according to Klik), Novak V. and Gregory A .: Phytosociology, Ecology, Iclimatology and Podoscience was practiced,

Nakl. ČSAV, Praha 1954. Kvantita cukrov holá stanovená spektrofotometrioky a přepočítaná na koncentrácie kalibračnej křivky glukózy. Pokusné súlbory boli porovnávané s kontrolným súborom rastlín.Loading. ČSAV, Praha 1954. Quantities of bare sugars determined by spectrophotometry and converted to glucose calibration curve concentrations. The test sets were compared with a control set of plants.

Výsledky pokusu sú uvedené v tabuEce 1.The results of the experiment are shown in Table 1.

Tabulka 1Table 1

Anlíkácia na list cukrovej řepy, hodnotené antronovou metodouSugar beet leaf appraisal, anthropically evaluated

Zlúičenína ipodla vynálezu mól. dm3 glukózaThe compound of the invention is mol. dm 3 glucose

X °/o stredná_ chyba SxX ° / o medium_ error Sx

3-metylbenzotiazollumbromlld 3-metylbenzotiazollumbromlld Kontrola 5 X ΙΟ3 lid-3 10-4 107 10’11 10-13Control 5 X ΙΟ 3 lid- 3 10-4 10 7 10 '11 10-13 100,00 128.75 126.75 .121,82 107,97 124,28 158,71 100.00 128.75 126.75 .121.82 107.97 124.28 158.71 !± 1+ Ψ l-H '± ! ± 1+ Ψ l-H '± 11,59 1,92 2,90 1,98 3,24 5,08 5,31 11.59 1.92 2.90 1.98 3.24 5.08 5.31 3,4-dimetylbenzotiazolíum- 3,4-dimetylbenzotiazolíum- Kontrola inspection 10.0,00 10.0,00 + + 12,15 12.15 bromid bromide 5 X ΙΟ3 5 X ΙΟ 3 137,25 137.25 + + 5,56 5.56 HO“3 HO “ 3 125,60 125.60 '+ '+ 1,08 1.08 10~4 10 ~ 4 122,78 122.78 + + 0,81 0.81 10’7 10 ' 7 74,67 74.67 + + 2,72 2.72 ío-11 ío- 11 91,46 91,46 + + 4,45 4.45 10~13 10 ~ 13 74,50 74.50 '+ '+ 8,58 8.58 3,4-idimetyilibenzO’tiazoliumjodřd 3,4-idimetyilibenzO'tiazoliumjodřd Kontrola inspection 100,00 100.00 + + 4,95 4.95 5 X ΙΟ’3 5 X ΙΟ ' 3 135,25 135.25 + + 3,42 3.42 ΙΟ'3 3 ' 3 114,57 114.57 '+ '+ 5,52 5.52 10-4 10-4 114,85 114.85 '+ '+ 2,00 2.00 10~7 10 ~ 7 97,09 97.09 + + 3.34 3:34 10-11 10- 11 99,80 99.80 + + 6,83 6.83 10~13 10 ~ 13 93,17 93.17 ± ± 1,75 1.75 3-metyil-4-chlórbenzotiazolium- 3-Methyl-4-chlórbenzotiazolium- Kontrola inspection 100,00 100.00 !+ ! + 6,35 6.35 bromid bromide 5 X ΙΌ“3 5 X ΙΌ “ 3 106,24 106.24 4,3,0 4,3,0 ΙΟ3 ΙΟ 3 111,10 111.10 + + 4,37 4.37 10'4 10 ' 4 82,04 82,04 + + 7,20 7.20 10~7 10 ~ 7 112,25 112.25 '± '± 6,86 6.86 ίο-11 ίο- 11 84,53 84.53 '± '± 5,96 5.96 10-13 10-13 80,67 80.67 2,45 2.45 3-metyl-4-chlórbenzotiazolium 3-methyl-4-chlórbenzotiazolium Kontrola inspection 100,00 100.00 ,+ + 1,74 1.74 jodid iodide 5 X ΙΟ3 5 X ΙΟ 3 157,97 157.97 ± ± 2,05 2.05 ΙΟ3 ΙΟ 3 154,03 154.03 4,55 4.55 10-4 10-4 137,04 137.04 ,± , ± 3,65 3.65 10'7 10 ' 7 105,6'6 105,6'6 li when 1,65 1.65 io-11 io- 11 83,26 83.26 i and 1,91 1.91 10-13 10-13 75,57 75.57 í s 1,17 1.17 3-metyl-4-chlórbenzotiazolium 3-methyl-4-chlórbenzotiazolium Kontrola inspection 100,00 100.00 i and 6,04 6.04 metosulfát methosulfate 5 X ΙΟ3 5 X ΙΟ 3 128,83 128.83 '± '± 3,35 3.35 10-3 10-3 122,69 122.69 ί ί 3,93 3.93 HO4 HO 4 132,01 132.01 i and 2,81 2.81 TO“7 TO “ 7 130,94 130.94 i and 5,56 5.56 TO-11 TO -11 130,24 130.24 ί ί 4,90 4.90 10-13 10-13 84,46 84.46 i and 3,94 3.94 3,6-dimetylbenzotiazolium- 3,6-dimetylbenzotiazolium- Kontrola inspection 100,00 100.00 + + 4,44 4.44 bromid bromide 5 X ΙΟ“3 5 X ΙΟ “ 3 135,49 135.49 i and 2,04 2.04 10-3 10-3 127,25 127.25 í-(- I - (- 2,23 2.23 ΙΟ4 ΙΟ 4 111,03 111.03 EE EE 3,22 3.22 107 10 7 108,19 108,19 rt rt 2,39 2.39 TO11 TO 11 104,64 104,64 H- H 2,00 2.00 10-13 10-13 100,42 100.42 i and 1,50 1.50

Zlúčenina podlá vynálezu A compound of the invention mól. dm-3 mole. dm -3 glukóza X % glucose X% 'i 'i středná chyba Sx mean error S x 3,6-dimetylbenzotiazoliumjodid 3,6-dimetylbenzotiazoliumjodid Kontrola inspection 100,00 100.00 + + 2,52 2.52 5 X 103 5 X 10 3 151,74 151.74 4- 4 0,88 0.88 10'3 10 ' 3 130,51 130.51 4- 4 4,11 4.11 10- 4 10- 4 118,38 118.38 + + 2,49 2.49 10-7 10- 7 96,24 96,24 + + 3,24 3.24 ÍO“11 ÍO '11 104,82 104.82 2,62 2.62 10-13 10-13 107,00 107.00 i and 3,31 3.31 3-metyl-6-chlórbenzotiazolium- 3-methyl-6-chlórbenzotiazolium- Kontrola inspection 100,00 100.00 + + 2,52 2.52 bromid bromide 5 X ΙΌ“3 5 X ΙΌ “ 3 112,36 112.36 ;+ , + 2,44 2.44 10-3 10- 3 109,30 109.30 1,09 1.09 ÍO4 ÍO 4 109,47 109,47 + + 2,20 2.20 10~7 10 ~ 7 95,55 95.55 2,16 2.16 ,10-11 , 10-11 84,82 84,82 '4- '4 2,33 2.33 10-13 10-13 79,96 79,96 + + 2,45 2.45 3-metyl-6-chIórbenzotiazolium- 3-methyl-6-chIórbenzotiazolium- Kontrola inspection 100,00 100.00 4 4 1,11 1.11 jodid iodide 5 X TO3 5 X TO 3 121,50 121.50 4- 4 0,68 0.68 103 10 3 106,81 106.81 + + 1,31 1.31 10- 4 10- 4 106,90 106.90 '+ '+ 1,03 1.03 107 10 7 110,84 110.84 0,96 0.96 1011 10 11 106,92 106.92 ,4- , 4- 1,11 1.11 1013 10 13 99,17 99.17 ± ± 0,99 0.99 3-alylbenzotiazoliumlbromid 3-alylbenzotiazoliumlbromid Kontrola inspection 100,00 100.00 4- 4 4,01 4.01 7 X ÍO'3 7 X 10 ' 3 179,69 179.69 4- 4 2,70 2.70 10 ~3 10 ~ 3 142,40 142.40 + + 3,85 3.85 10“7 10 “ 7 117,75 117.75 + + 0,89 0.89 10-13 10- 13 105,87 105.87 ± ± 1,29 1.29 3-karboxymetyIbenzotiazolíum- 3-karboxymetyIbenzotiazolíum- Kontrola inspection 100,00 100.00 '+ '+ 2,87 2.87 bromid bromide 5 X ÍO3 5 X IO 3 119,17 119.17 5,17 5.17 10-3 10- 3 111,17 111.17 '+ '+ 1,94 1.94 10~4 10 ~ 4 121,50 121.50 4- 4 2,63 2.63 10-7 10- 7 1012,55 1,012.55 4- 4 2,44 2.44 10-11 10- 11 103,66 103.66 4- 4 7,96 7.96 10-13 10-13 174,71 174.71 ΈΕ ΈΕ 8,95 8.95 3-metoxykarbonylmetylbeinzo- 3-metoxykarbonylmetylbeinzo- Kontrola inspection 100,00 100.00 11 ' 11 ' 1,40 1.40 tiazoliumbromid thiazolium 5 X 1Ώ3 5 X 1Ώ 3 174,26 174.26 3,40 3.40 10-3 10- 3 157,91 157.91 1 1 1 1 2,05 2.05 ÍO4 ÍO 4 143,66 143,66 1 » 1 » 1,48 1.48 io-7 io- 7 115,18 115.18 fp fp 2,83 2.83 10-11 10- 11 111,77 111.77 1,57 1.57 1013 10 13 111,32 111.32 4~ 4 ~ 1,13 1.13 3 - e toxykarb o ny lm ety lb enzotia- 3 - e toxycarbonynylbenzzothia- Kontrola inspection 100,00 100.00 4- 4 3,70 3.70 zoliumbromid tetrazolium bromide 5 X 10“3 5 X 10 “ 3 158,81 158,81 '4- '4 3,15 3.15 10~3 10 ~ 3 142,11 142.11 '4- '4 2,21 2.21 10-4 10- 4 110,96 110,96 Ψ Ψ 2,59 2.59 io-7 io- 7 110,51 110,51 3,42 3.42 10-11 10-11 102,29 102.29 4- 4 3,79 3.79 10-15 10-15 104,91 104.91 i and 3,36 3.36 3-propoxykarbonylmetylbenzo- 3-propoxykarbonylmetylbenzo- Kontrola inspection 100,00 100.00 '4- '4 4,17 4.17 tiazoliumbromid thiazolium ÍO’2 ÍO ' 2 158,71 158.71 4- 4 4,53 4.53 8 X 10~3 8 X 10 ~ 3 153,78 153.78 4- 4 5,91 5.91 5 X 10~3 5 X 10 ~ 3 138,25 138.25 '4- '4 4,66 4.66 ilO“3 ILO "3 121,59 121.59 4- 4 4,36 4.36 10“7 10 “ 7 117,00 117.00 4J 4 J 1,94 1.94 10-13 10-13 118,18 118.18 Ψ Ψ 1,28 1.28

Zlúičenina -podlá vynálezu Compound of the Invention mól. dm~3 mole. dm ~ 3 glukóza X % glucose X% + + středná chyba sx mean error with x 3-izopropoxykarbonylmetyl- 3-izopropoxykarbonylmetyl- Kontrola inspection 100,00 100.00 + + 1,95 1.95 benzoíiazoliumbromid benzoíiazoliumbromid 5 X ΙΟ“3 5 X ΙΟ “ 3 131,02 131,02 + + 5,88 5.88 TO3 TO 3 126,70 126.70 + + 7,06 7.06 10-4 10-4 90,89 90.89 + + 2,71 2.71 10~7 10 ~ 7 89,63 89.63 .+ . + 1,23 1.23 10-11 10- 11 91,95 91.95 + + 3,18 3.18 10~13 10 ~ 13 85,52 85,52 ,± , ± 7,68 7.68 3-alyloxykarbonylmetyl'benzo- 3-alyloxykarbonylmetyl'benzo- Kontrola inspection 100,00 100.00 + + 3,47 3.47 tiazoliumbromid thiazolium 5 X ΙΟ3 5 X ΙΟ 3 135,32 135.32 .+ . + 2,73 2.73 ΙΟ“3 3 “ 3 146,51 146.51 + + 5,14 5.14 ΙΟ’4 4 ' 4 135,05 135.05 + + 3,00 3.00 10-7 10-7 124,32 124.32 '+ '+ 4,85 4.85 10~n 10 ~ n 127,26 127.26 '+ '+ 1,55 1.55 ίο-13 ίο- 13 115,48 115.48 ± ± 0,88 0.88 3- (3‘-chlónbenzyl) -benzotiazo- 3- (3‘-Chlorobenzyl) -benzothiazole- Kontrola inspection 100,00 100.00 + + 5,81 5.81 liumbromid diphenyltetrazolium bromide 10-3 10- 3 122,21 122.21 4- 4 0,92 0.92 10 ~5 10 ~ 5 125,13 125.13 1,30 1.30 10~7 10 ~ 7 122,33 122.33 + + 1,52 1.52 10-13 10-13 114,19 114.19 + + 2,05 2.05 3- (2‘-chlórbenzyl) benzotiazo- 3- (2‘-Chlorobenzyl) benzothiazole Kontrola inspection 100,00 100.00 + + 2,19 2.19 liumbromid diphenyltetrazolium bromide 10-3 10-3 111,23 111.23 + + 8,81 8.81 HO5 HO 5 108,60 108.60 + + 2,40 2.40 10~7 10 ~ 7 85,54 85.54 3,14 3.14 10-13 10- 13 98,31 98.31 ±  ± 4,66 4.66 3 -bi s zmy lb e-nzot iaz o liu mb r om i d 3 -bi s lm lb e-nzot iaz o liu mb r om i d Kontrola inspection 100,00 100.00 + + 2,10 2.10 10~3 10 ~ 3 189,02 189.02 + + 6,06 6.06 10~5 10 ~ 5 21-5,47 21 to 5.47 + + 5,73 5.73 10~7 10 ~ 7 197,72 197.72 + + 4,58 4.58 10-13 10- 13 204,60 204,60 1,50 1.50 3-izopropylbenzotiazolium- 3-izopropylbenzotiazolium- Kontrola inspection 100,0 100.0 + + 10,82 10.82 bromid bromide 103 10 3 142,8 142.8 + + 4,81 4.81 ΙΟ4 ΙΟ 4 139,-6 139 -6 + + 6,11 6.11 ΙΟ“7 7 “ 7 96,4 96.4 + + 4,21 4.21 10-11 10- 11 89,2 89.2 + + 1,36 1.36 10-13 10- 13 90,6 90.6 + + 2,88 2.88 3-decylbenzotiazoliumbromid 3-decylbenzotiazoliumbromid Kontrola inspection 100,0 100.0 + + 9,82 9.82 io-3 io- 3 122,6 122.6 + + 1,52 1.52 ΙΟ4 ΙΟ 4 12-9,2 12-9.2 + + 3,41 3.41 10“7 10 “ 7 100,6 100.6 + + 1,22 1.22 10“11 10 “ 11 111,2 111.2 + + 0,90 0.90 1013 10 13 106,3 106.3 ± ± 4,11 4.11 3 -p rop argyl-b e nzotiazolium- 3-petroleum-benzene-thiazolium- Kontrola inspection 100,0 100.0 + + 2,11 2.11 bromid bromide |10~3 10 ~ 3 131,2 131.2 + + 4,12 4.12 ΙΟ“4 4 “ 4 128,4 128.4 + + 3,11 3.11 ÍO’7 ÍO ' 7 100,9 100.9 + + 0,62 0.62 10-11 10- 11 90,6 90.6 '+ '+ 0,48 0.48 IO-13 IC-1 3 98,2 98.2 + + 1,22 1.22 3- (N-propargylkarbonylmetyl) - 3- (N-propargylcarbonylmethyl) - Kontrola inspection 100,0 100.0 + + 3,10 3.10 benzotiazoliumbromid benzotiazoliumbromid ÍO“3 ÍO “ 3 119,6 119.6 2,11 2.11 ÍO’4 4 ' 116,8 116.8 + + 3,62 3.62 ÍO“7 ÍO ' 7 100,4 100.4 + + 2,64 2.64 ÍO“11 ÍO '11 98,2 98.2 + + 1,44 1.44 10-43 10-43 106,1 106.1 '+ '+ 0,88 0.88

Zlúčenina [podía vynálezu Compound [of the invention mól. dm-3 mole. dm -3 glukóza X °/o glucose X ° / o ± ± středná chyba Sx mean error Sx 3- (N,N-dimetyltiokarbamoyl- 3- (N, N-dimethylthiocarbamoyl- Kontrola inspection 100,0 100.0 + + 1,22 1.22 metyl jbenzotiazoliumbroinid methylbenzothiazoliumbroinide io-3 io- 3 132,8 132.8 + + 3,24 3.24 10 4 10 4 131,4 131.4 + + 4,11 4.11 10-7 10- 7 112,6 112.6 + + 0,94 0.94 ,10-11 , 10-11 106,2 106.2 + + 1,22 1.22 10-13 10- 13 108,4 108.4 + + 1,66 1.66 3- (N,N-dietyl'ditiokarbamoyl- 3- (N, N-diethyl'dithiocarbamoyl- Kontrola inspection 100,0 100.0 + + 1,14 1.14 metyl jbenzotiazoliumbromild methylbenzothiazolium bromide 10-3 10- 3 132,4 132.4 + + 2,44 2.44 10-4 10- 4 138,6 138.6 + + 6,11 6.11 10~7 10 ~ 7 122,4 122.4 + + 3,26 3.26 10-11 10- 11 106,1 106.1 + + 1,22 1.22 10-13 10- 13 92,4 92.4 EE EE 0,91 0.91 3- (N,N-dibutylkarbamoylme- 3- (N, N-Dibutylcarbamoylme- Kontrola inspection 100,0 100.0 + + 4,11 4.11 tyl ] benzotiazoliumibr omid tyl] benzothiazolium lime omid 10~3 10 ~ 3 122,4 122.4 + + 3,26 3.26 ío-4 ío- 4 128,2 128.2 + + 1,88 1.88 10~7 10 ~ 7 110,1 110.1 + + 2,44 2.44 ίο-π ίο-π 108,4 108.4 + + 1,49 1.49 10-13 10- 13 112,8 112.8 ± ± 0,98 0.98 3-(N-fenylkarbamoylmetyl)- 3- (N-phenylcarbamoylmethyl) - Kontrola inspection 100,0 100.0 + + 0,98 0.98 benzotiazoliumbromid benzotiazoliumbromid io-3 io- 3 104,2 104.2 + + 1,41 1.41 ÍO“4 ÍO “ 4 111,8 111.8 + + 2,11 2.11 10~7 10 ~ 7 122,6 122.6 +' + ' 0,6'6 0,6'6 ío-11 ío- 11 100,1 100.1 + + 1,22 1.22 * * 10-13 10- 13 111,2 111.2 ί ί 3,00 3.00 3-(N-/3-metylf enyl/karbamoyl- 3- (N- (3-methylphenyl) carbamoyl- Kontrola inspection 100,0 100.0 1,94 1.94 metyl jbemzotiazoliumbromid methyl jbemzothiazolium bromide 10“3 10 “ 3 138,4 138.4 + + 2,11 2.11 10-4 10- 4 128,2 128.2 + + 1,21 1.21 10~7 10 ~ 7 106,2 106.2 + + 3,16 3.16 ÍO11 ÍO 11 90,1 90.1 + + 5,11 5.11 10-13 10- 13 101,1 101.1 ± ± 2,01 2.01 3- (N-/2-chlórf enyl/karbamoyl- 3- (N- (2-chlorophenyl) carbamoyl- Kontrola inspection 100,0 100.0 + + 0,94 0.94 metyl jbenzotiazoliumlbromiid methylbenzothiazolium bromide 10“3 10 “ 3 131,2 131.2 + + 2,12 2.12 10-4 10- 4 124,2 124.2 + + 3,17 3.17 10~7 10 ~ 7 120,4 120.4 + + 1,68 1.68 ío-11 ío- 11 109,1 109.1 + + 2,10 2.10 ÍO17 ÍO 17 90,6 90.6 + + 1,10 1.10 3-(N-/4-metoxyfenyl/karbamo- 3- (N / 4-methoxyphenyl / karbamo- Kontrola inspection 100,0 100.0 +' + ' 1,66 1.66 ylmetyl) benzotiazoliumbromid ylmethyl) benzothiazolium bromide 10 3 10 3 111,6 111.6 3,11 3.11 104 10 4 122,4 122.4 + + 2,02 2.02 10“7 10 “ 7 106,2 106.2 + + 1,11 1.11 ÍO11 ÍO 11 48,4 48.4 + + 6,81 6.81 ÍO13 ÍO 13 96,1 96.1 + + 4,24 4.24 3- (N-/4-nitrof enyl/karbamoyl- 3- (N- (4-nitrophenyl) carbamoyl- Kontrola inspection 100,0 100.0 + + 2,41 2.41 metyl) benzotiazoliumbromid methyl) benzothiazolium bromide 10“3 10 “ 3 138,2 138.2 + + 1,48 1.48 10-4 10- 4 131,4 131.4 + + 0,82 0.82 10-7 10- 7 102,4 102.4 + + 4,11 4.11 10-11 10- 11 90,2 90.2 + + 2,55 2.55 10-13 10- 13 98,4 98.4 ± ± 1,10 1.10 3- (N-/4-aoetylamínofenyl/kar- 3- (N- (4-Aethylamino-phenyl) -car- Kontrola inspection 100,0 100.0 + + 0,88 0.88 bamoylmetyl jbenzotiazolium- bamoylmethyl jbenzothiazolium- 103 10 3 124,'8 124, "8 + + 2,47 2.47 bromid bromide 10 “4 10 “ 4 131,8 131.8 + + 3,28 3.28 io-7 io- 7 111,6 111.6 + + 1,41 1.41 ío-11 ío- 11 119,8 119.8 + + 2,17 2.17 1013 10 13 108,1 108.1 + + 1,19 1.19

Zlúčenina podía vynálezu A compound of the invention mól. dm~3 mole. dm ~ 3 glukóza X % glucose X% i and středná chyba Sx mean error S x 3-(N-/3,4-dichlórfenyl/karba- 3- (N- / 3,4-dichloro-phenyl / carbamoyl Kontrola inspection 100,0 100.0 + + 2,72 2.72 moylmetyl Jbenzotiazolium- moylmethyl Jbenzothiazolium- ,10~3 , 10 ~ 3 106,8 106.8 4“ 4 ' 0,91 0.91 bromid bromide 10-4 10- 4 118,2 118.2 4,18 4.18 107 10 7 100,2 100.2 + + 3,22 3.22 10-11 10- 11 90,8 90.8 + + 1,48 1.48 10-13 10-13 102,4 102.4 + + 2,46 2.46 3- (N-metyl-N-fenylkarbamoyl- 3- (N-methyl-N-phenylcarbamoyl- Kontrola inspection 100,0 100.0 + + 2,29 2.29 metyl) benzotiazoliumbromid methyl) benzothiazolium bromide IO-3 IO -3 141,8 141.8 4,87 4.87 IO4 IO 4 126,1 126.1 + + 6,12 6.12 107 10 7 104,2 104.2 + + 1,47 1.47 10“11 10 “ 11 102,1 102.1 + + 2,20 2.20 10-13 10- 13 104,7 104.7 + 1 + 1 4,11 4.11 3-pyrolidinylkarbonylmetyl- 3-pyrolidinylkarbonylmetyl- Kontrola inspection 100,0 100.0 zt zt 4,82 4.82 benzotiazoliumbromid benzotiazoliumbromid 103 10 3 129,8 129.8 2,76 2.76 10~4 10 ~ 4 126,2 126.2 + + 1,77 1.77 10-z 10- z 103,2 103.2 + + 0,88 0.88 10~u 10 ~ u 111,6 111.6 4“ 4 ' 4,82 4.82 10-13 10- 13 100,8 100.8 + + 1,44 1.44 3-morfolinokarbonylmetylben- 3-morfolinokarbonylmetylben- Kontrola inspection 100,0 100.0 7,22 7.22 zotiazoliumbromid zotiazoliumbromid 10-3 10- 3 137,2 137.2 + + 2,11 2.11 10-4 10- 4 128,4 128.4 + + 4,74 4.74 10'7 10 ' 7 119,2 119.2 + + 3,41 3.41 10“11 10 “ 11 122,4 122.4 + + 0,98 0.98 - - 10-13 10- 13 111,1 111.1 ± ± 2,10 2.10 3- (N-cyklohexylkarbanoylme- 3- (N-cyclohexylcarbanoylme- Kontrola inspection 100,0 100.0 + + 1,46 1.46 tyljbenzotiazoliumbromid tyljbenzotiazoliumbromid io-3 io- 3 127,2 127.2 4“ 4 ' 2,08 2.08 10~4 10 ~ 4 120,1 120.1 + + 2,98 2.98 10~7 10 ~ 7 111,6 111.6 4“ 4 ' 4,72 4.72 10-11 10- 11 118,2 118.2 + + 7,28 7.28 ’ 10-13 10- 13 106,1 106.1 ± ± 1,14 1.14 3-(2-nitr obenzyl)-6-metylben- 3- (2-nitro-benzyl) -6-methyl-benzene Kontrola inspection 100,0 100.0 + + 2,68 2.68 zotiazoliumbromid zotiazoliumbromid 10-3 10 -3 129,8 129.8 + + 1,47 1.47 10-4 10- 4 119,1 119.1 +' + ' 1,98 1.98 IO-7 IO -7 102,2 102.2 + + 7,11 7.11 10-n 10-n 106,8 106.8 + + 4,88 4.88 10-13 10- 13 99,7 99.7 ± ± 1,72 1.72 3-(4-ibrómbenzylJ-6-metylben- 3- (4-ibrómbenzylJ-6-metylben- Kontrola inspection 100,0 100.0 + + 2,27 2.27 z ot ia z ol iu mbr omi d z ot ia z ol iu mbr omi d IO“3 IO ' 3 148,2 148.2 + + 3,01 3.01 10‘4 10 ' 4 137,1 137.1 + + 2,72 2.72 10“7 10 “ 7 112,1 112.1 + + 1,17 1.17 10-11 10- 11 109,8 109.8 + + 0,88 0.88 10-13 10- 13 111,7 111.7 ± ± 2,11 2.11 3- (4-f luorbemzyl) -6-metylben- 3- (4-fluorobenzyl) -6-methylbenzyl Kontrola inspection 109,0 109.0 +' + ' 1,19 1.19 zotiazoliumbromid zotiazoliumbromid IO-3 IO -3 152,2 152.2 + + 2,27 2.27 10~4 10 ~ 4 148,7 148.7 + + 3,18 3.18 107 10 7 121,2 121.2 +' + ' 1,72 1.72 10-n 10-n 100,4 100.4 + + 0,87 0.87 10-13 10-13 111,2 111.2 + + 2,01 2.01 3- (4-me toxyb enzyl) - 6-mety 1 - 3- (4-Methoxybenzyl) -6-methyl Kontrola inspection 100,0 100.0 + + 9,0,2 9,0,2 benzotiazoliumbromid benzotiazoliumbromid 10-3 10 -3 158,2 158.2 + + 1,22 1.22 10-4 10- 4 150,4 150.4 +’ + ' 1,78 1.78 10-7 10 -7 140,2 140.2 + + 6,22 6.22 10-n 10-n 118,6 118.6 4,10 4.10 IO-» IO- » 112,8 112.8 + + 2,81 2.81

Zlúěenina podlá vynálezu Compound of the Invention mól. dm-3 mole. dm -3 glukóza X % glucose X% ± ± středná, chyba Sx medium, error Sx 3-(4-,kyano'benzyl)-6-metyl'be'n- 3- (4, kyano'benzyl) -6-metyl'be'n- Kontrola inspection 100,0 100.0 + + 2,74 2.74 zotiazoiliuitíbromid zotiazoiliuitíbromid ícr3 ícr 3 162,8 162.8 + + 1,02 1.02 lQ-4 LQ-4 148,7 148.7 + + 7,47 7.47 io-7 io- 7 150,2 150.2 3,18 3.18 1Q-U Q1-U 111,2 111.2 + + 2,16 2.16 10-Í3 10-I3 106,2 106.2 ± ± 1,72 1.72 3-(4-sulfanoylbenzyl)-6-matyl- 3- (4-sulfanoylbenzyl) -6-matyl- Kontrola inspection 100,0 100.0 + + 7,82 7.82 benzotiazoliumbromid benzotiazoliumbromid 10-3 10- 3 127,1 127.1 + + 2,41 2.41 10-4 10-4 122,4 122.4 + + 3,88 3.88 10-7 10 -7 111,9 111.9 + + 0,78 0.78 ío-11 ío- 11 112,2 112.2 + + 1,17 1.17 10“13 10 “ 13 100,6 100.6 ± ± 2,01 2.01 3- (1-naftylme tyl) -B-metylben- 3- (1-naphthylmethyl) -B-methylbenz- Kontrola inspection 100,0 100.0 + + 6,81 6.81 zotiazoliumbromid zotiazoliumbromid ÍO“3 ÍO “ 3 118,7 118.7 3,18 3.18 10-4 10-4 114,2 114.2 + + 2,44 2.44 10-7 10- 7 100,1 100.1 + + 1,22 1.22 1011 10 11 102,4 102.4 + + 1,77 1.77 10-13 10- 13 90,7 90.7 ± ± 2,11 2.11 3- (3,4-idichlórbenzyl) -6 -metyl- 3- (3,4-idichlorobenzyl) -6-methyl- Kontrola inspection 100,0 100.0 7,22 7.22 benzatiazoliumbromid benzatiazoliumbromid ÍO-3 ÍO- 3 148,7 148.7 + + 5,12 5.12 10-4 10- 4 151,2 151.2 + + 1,72 1.72 10~7 10 ~ 7 122,4 122.4 + + 1,47 1.47 ío-11 ío- 11 118,7 118.7 + + 3,81 3.81 ío-13 í - 13 102,2 102.2 ·+ · + 1,17 1.17 3-feinetyl-6-mety,])be.nzotiazo- 3-feinetyl-6-methyl,]) be.nzotiazo- Kontrola inspection 100,0 100.0 + + 5,21 5.21 liumbromid diphenyltetrazolium bromide ÍO“3 ÍO “ 3 124,8 124.8 + + 2.21 2.21 10-4 10- 4 122,8 122.8 + + 0,84 0.84 10-7 10- 7 111,4 111.4 + + 1,22 1.22 10-u 10-u 108,6. 108.6. 2,71 2.71 10-13 10- 13 117,2 117.2 + + 1,92 1.92

Claims (1)

PREDMETSUBJECT VYNALEZUWe claim: Prostriedok na zvyšovanie obsahu cukrov v rostlinách prolukujúcich cukor na báze substituovaných 3-R-bemzotiazoliových solí vyznačujúci sa tým, že ako účinnú látku Obsahuje substituovanú benzotiazoliovú sol' všeobecného vzorca IA composition for increasing the sugar content of sugar-pricking plants based on substituted 3-R-bemzothiazolium salts, characterized in that it contains, as active ingredient, a substituted benzothiazolium salt of the formula I R2 znamená vodík alebo· alkyl s 1 až 3 atómami uhlíka,R 2 is hydrogen or • alkyl of 1 to 3 carbon atoms, R3 znamená vodík, metyl alebo chlór,R 3 is hydrogen, methyl or chloro, R4 znamená metyl, halogen, metoxyskuipinu, nitroskupinu, kyanoskupinu, sulfooamidoskupinu, metoxysulfoskupinu, naftylmetyl,R 4 is methyl, halo, metoxyskuipinu, nitro, cyano, sulfooamidoskupinu, metoxysulfoskupinu, naphthylmethyl, R5 znamená vodík, alkyl s 1 až 4 atómami uhlíka, allyl, propargyl, benzyl alebo zvyšok vzorca v ktorom v ktoromR 5 is hydrogen, alkyl of 1 to 4 carbon atoms, allyl, propargyl, benzyl or a radical of formula in which: R1 znamená alkyl s počtom 1 až 10 atómov uhlíka, alkyl, propargyl, žvyšolk vzorca (CH?) ί'η.R 1 represents an alkyl of 1 to 10 carbon atoms, alkyl, propargyl, a radical of formula (CH 2) n '. -(/? Prrl ;- (/? P rrl ; alebo — (CH2)n—C—Z—R5 II γor - (CH2) n —C — Z — R 5 II γ R6 znamená vodík, metyl, halogén, metoxyskupinu, nitroskupinu, acetylamínoskupinu,R 6 is hydrogen, methyl, halogen, methoxy, nitro, acetylamino, R7 znamená vodík, metyl, pričom R5 spolu s R7 a dusíkom připadne tvoří 5- alebo 6-členný heterocyklický kruh, připadne obsahujúici tiež atom kyslíka,R 7 is hydrogen, methyl, wherein R 5 together with R 7 and nitrogen optionally form a 5- or 6-membered heterocyclic ring, optionally containing an oxygen atom, Y znamená O alebo S, 'Z znamená O, S alebo —NR7—, ni a n sú celé čísla 0 až 2, o znamená 1 alebo· 2 a X znamená halogén, predovšetkým chlór, 'bróm alebo jód, CH3SO4, a to· v koncentrácii 10-15 až 10_1 mól, s výhodou v rozmedzí 10-13 ,až 10-2 mól.Y is O or S, Z is O, S or — NR 7 -, n and n are integers from 0 to 2, o is 1 or 2 and X is halogen, especially chlorine, bromine or iodine, CH 3 SO 4, namely · at 10 -15 to 10 _1 moles, preferably in the range of 10 -13 to 10 -2 mol. v ktoromin which
CS755584A 1984-10-05 1984-10-05 Agent for encreasing the content of sugar CS250876B1 (en)

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CS755584A CS250876B1 (en) 1984-10-05 1984-10-05 Agent for encreasing the content of sugar

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2444517C2 (en) * 2006-01-27 2012-03-10 Бейджинг Моликьюл Сайенс Энд Текнолоджи Ко., Лтд Novel salts of substituted 5-member azacycle and use thereof in treating protein ageing related diseases

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2444517C2 (en) * 2006-01-27 2012-03-10 Бейджинг Моликьюл Сайенс Энд Текнолоджи Ко., Лтд Novel salts of substituted 5-member azacycle and use thereof in treating protein ageing related diseases

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