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