CS272749B1 - 3-/2-hydroxyethyl/-6-nitro-2-benzothiazolinone - Google Patents
3-/2-hydroxyethyl/-6-nitro-2-benzothiazolinone Download PDFInfo
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- CS272749B1 CS272749B1 CS569789A CS569789A CS272749B1 CS 272749 B1 CS272749 B1 CS 272749B1 CS 569789 A CS569789 A CS 569789A CS 569789 A CS569789 A CS 569789A CS 272749 B1 CS272749 B1 CS 272749B1
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 229930002875 chlorophyll Natural products 0.000 claims abstract description 16
- 235000019804 chlorophyll Nutrition 0.000 claims abstract description 16
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims abstract description 16
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- MWEVBWFZLWVZQJ-UHFFFAOYSA-N 3-(2-hydroxyethyl)-6-nitro-1,3-benzothiazol-2-one Chemical compound C1=C([N+]([O-])=O)C=C2SC(=O)N(CCO)C2=C1 MWEVBWFZLWVZQJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 230000008635 plant growth Effects 0.000 claims abstract description 3
- 230000012010 growth Effects 0.000 claims description 16
- 240000008042 Zea mays Species 0.000 claims description 14
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 7
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 6
- 235000005822 corn Nutrition 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 241000195493 Cryptophyta Species 0.000 claims description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 5
- 235000009973 maize Nutrition 0.000 claims description 5
- 240000009108 Chlorella vulgaris Species 0.000 claims description 4
- 235000007089 Chlorella vulgaris Nutrition 0.000 claims description 4
- 230000004936 stimulating effect Effects 0.000 claims description 4
- 241000195628 Chlorophyta Species 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 2
- 238000003359 percent control normalization Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 235000015097 nutrients Nutrition 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 244000052616 bacterial pathogen Species 0.000 claims 1
- 238000012136 culture method Methods 0.000 claims 1
- 239000003501 hydroponics Substances 0.000 claims 1
- 238000005286 illumination Methods 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 230000000885 phytotoxic effect Effects 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract description 3
- QITPMSSAFSZYOP-UHFFFAOYSA-N 6-nitro-3h-1,3-benzothiazol-2-one Chemical compound C1=C([N+]([O-])=O)C=C2SC(O)=NC2=C1 QITPMSSAFSZYOP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000001963 growth medium Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- -1 S-nitro-2-benzothiazolinone Chemical compound 0.000 description 3
- 235000007244 Zea mays Nutrition 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- GLRHCXKQSXFQHY-UHFFFAOYSA-N 5-nitro-3h-1,3-benzothiazol-2-one Chemical compound [O-][N+](=O)C1=CC=C2SC(=O)NC2=C1 GLRHCXKQSXFQHY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000195649 Chlorella <Chlorellales> Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002789 length control Methods 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
3-/2-Hydroxyetyl/-6-nitro-2-benzotiazolinón (57) Bol připravený doteraz neznámy 37/2-hydroxYetyl/-6-nitro-2-benzotiazoli~ nón. Syntéza uvedenej zlúčeniny sa uskutečňuje reakciou draselnéj soli/5-nitro-2-benzotiazolinónu 3 etylénchlórhydrinom v zmesi etanolu a vody za varu. Zlúčenina je stimulačně účinná na rast rastlin a zelených rias, ako aj na syntézu chlorofylu.3- (2-Hydroxyethyl) -6-nitro-2-benzothiazolinone (57) The hitherto unknown 37/2-hydroxyethyl] -6-nitro-2-benzothiazolinone was prepared. The synthesis of said compound is carried out by reacting the potassium salt of 5-nitro-2-benzothiazolinone with 3 ethylene chlorohydrin in a mixture of ethanol and water at boiling. The compound has a stimulatory effect on the growth of plants and green algae as well as on the synthesis of chlorophyll.
CS 272749 BlCS 272749 Bl
-ft-ft
CS 272 749 BlCS 272 749 Bl
Predmetom vynálezu je 3-/2-hydroxyetyl/-6-nitro-2-benzotiazolinon,The present invention provides 3- (2-hydroxyethyl) -6-nitro-2-benzothiazolinone,
3-Subatítuované deriváty 6-nitro-ž-benzotiazolinonu prajavili účinnost ako regulátory rastu rastlin /ďÁmico 3.0. US pat. 4 282 023 /1381/? Sidóová? Ε., tílanáríkavá, V», Mitterhauszerová, Íl-.*a Králová? K·/ PV «564-88/ a ako herbicidy /0 Amico 0.0. US pat. 4 185 990 /1980//.3-Substituted 6-nitro-β-benzothiazolinone derivatives have proven to be effective as plant growth regulators / D'Amico 3.0. US Pat. 4,282,023 / 1381 /? Sidóová? Ε., Tílanáríkavá, V », Mitterhauszerová, Íl -. * And Králová? K · (PV 56 564-88) and as herbicides (0 Amico 0.0). US Pat. No. 4,185,990 (1980) //.
Teraz sne zistili, že doteraz neznáma zlúčenina vzorcaNow they have found that a hitherto unknown compound of formula
,C=0C = 0
CHg-CHg-OH stimuluje rast a syntézu chlorofylu rias Chlorella vulgaris a rast korenov a stonisk, ako je nárast čerstvaj hmoty u kukuřice.CHg-CHg-OH stimulates the growth and synthesis of chlorophyll of Chlorella vulgaris and the growth of roots and stalks such as the growth of fresh matter in maize.
Súčasne bol zlatěny sposob přípravy uvsdenej zlúčeniny \reakciou draselnej soliAt the same time, the preparation of said compound by the reaction of the potassium salt was golden
S-nitro-2-bsnzotiazolinónu s etylénchlórhydrínom v zmesi etanolu a vody za varu.S-nitro-2-benzothiazolinone with ethylene chlorohydrin in a mixture of ethanol and water at boiling.
Nasledujúce příklady bližšie osvetlujú?' ale nijako naobmedzujú přípravu a vlastnosti zlúčeniny podlá vynálezu.The following examples illustrate in more detail? ' but do not limit the preparation and properties of the compound of the invention.
Přiklad 1Example 1
Příprava 3-/2-hydroxyetyl/-6-nitro-2-benzotiazolinónuPreparation of 3- (2-hydroxyethyl) -6-nitro-2-benzothiazolinone
6-Nitro-2-benzotiazolinón /5?9 g, 0/03 mol/ bol rozpuštěný za varu v roztoku hy3 3 droxidu draselného /2/0 g/ 0/03 mol/ v zmesi etanolu /20 cm / a vody /10 cm /. K roztoku sa přidal etylénchlórhydrín /3/0 g/ 0/036-mol/ a reakčná zmes sa refluxovala 3 hodiny a potom sa odstavila cez noc pri 5 °C. Z roztoku sa vylúčil produkt s t.t. 150 až 15S °C v množstve S,05 g /84/0 %/.6-Nitro-2-benzothiazolinone (5-9 g, 0/03 mol) was dissolved under boiling in a solution of potassium hydroxide (2/0 g / 0/03 mol) in a mixture of ethanol (20 cm) and water (10 g). cm /. To the solution was added ethylene chlorohydrin (3/0 g / 0/036-mol) and the reaction mixture was refluxed for 3 hours and then left overnight at 5 ° C. The product with m.p. 150 DEG-15 DEG C. in an amount of 5.05 g (84%).
Vzorka pre analýzu bola přečištěná kryštalizáciou z octanu stylového za použitia aktivneho uhlia/ čím sa získal čistý 3-/2-hydroxyetyl/-S-nitro-2-benzotiazolinon s t.t. 160 až 162 °C« M.h, » 240/24The sample for analysis was purified by crystallization from stylic acetate using activated carbon to give pure 3- (2-hydroxyethyl) -S-nitro-2-benzothiazolinone, m.p. 160 DEG-162 DEG C. «M.h,» 240/24
Pre CgH8N204S vypočítané % i C 45/00 Η 3?36 N 11/66 S 13?35 zistené % : 44/99 3/32 11/77 13,64For C g H 8 N 2 0 4 S calculated% i C 45/00 Η 3? 36 N 11/66 N 13? 35 found%: 44/99 3/32 11/77 13,64
Příklad 2Example 2
Účinok 3-/2-hydroxyetyl/«6-nitro-2-benzotiazolinónu na rast a syntézu chlorofylu zelených riasEffect of 3- (2-hydroxyethyl) -6-nitro-2-benzothiazolinone on the growth and synthesis of chlorophyll green algae
Tabulka k přikladu 2Table for example 2
Vplyv zlúčeniny podlá vynálezu na rast a obsah syntetizovaného chlorofylu rias Chlorella vulgarisEffect of compound of the invention on growth and content of synthesized chlorophyll of Chlorella vulgaris
CS 272 749 BlCS 272 749 Bl
Riasy Chlorella vulgaris sa pěstovali stacionárnou kultiváciou pri teplote 25 i 1 °0 pri svetelnom režime 16 hodin světlo, 8 hodin tma, v kultivačnom médiu podlá Setlíka /Šetlík I.: Annual Report of Algolog. Lab. for 1967, 71-140, Třeboň 1968/. Testovaná látka sa přidávala do kultivačného média v roztoku dimetylformamidu /celkový obsah rozpúštadla v kultivačnom médiu bol 1 %/ a ten istý objem rozpúštadla sa přidával ku kontrolným vzorkám. Kultivačně banky sa inokulovali přesným objemom homogénnej suspenzie rias.Algae of Chlorella vulgaris were grown by stationary cultivation at both 25 ° C and 10 ° C at 16 hours light, 8 hours dark, in a culture medium according to Setlík / Šetlík I .: Annual Report of Algolog. Lab. for 1967, 71-140, Trebon 1968 /. The test substance was added to the culture medium in dimethylformamide solution (total solvent content in the culture medium was 1%) and the same volume of solvent was added to the controls. Culture flasks were inoculated with an exact volume of homogeneous algae suspension.
Ro 7 dennej kultivácii sa objem kultivačného média doplnil destilovanou vodou na povodný objem /vyrovnanie odparu vody/ a v suspenzii buniek sa merala absorbancia pri 660 nm /úměrná množstvu buniek rias/ a obsah chlorofylu po jeho extrakcii di metylformami dnm z odcentrifúgovaných . buniek rias /Inskeep W.P., Bloom P.R.: Plant Physiol. 77/2/, 483-5, 1985/.In a 7-day cultivation, the volume of the culture medium was made up to the original volume with distilled water (equalizing the water evaporation) and absorbance at 660 nm (proportional to the number of algal cells) and chlorophyll content were extracted after centrifugation. algae cells / Inskeep W.P., Bloom P.R .: Plant Physiol. 77 (2), 483-5 (1985).
Zlúčenina podlá vynálezu stimulovala rast a syntézu chlorofylu rias Chlorella vulga-5 -13 -3 ris v koncentračnom rozmedzí 1.10 ' až 1.10 J mol.dm . Stimulačná účinnosC, vyjádřená percentuálně vzhladom na hodnoty zistené v súčasné kultivovaných kontrolných vzorkách, je uvedená v tabulke k příkladu 2.Compounds of the invention stimulate growth and synthesis of chlorophyll of algae Chlorella vulga 5 -13 -3-ris a concentration range of 1.10 "to 1.10 mol.dm J. The stimulatory activity, expressed as a percentage of the values found in the current cultured control samples, is shown in the table of Example 2.
Příklad 3 °Example 3 °
Test fytotoxicity zlúčeniny podlá vynálezu a jej vplyvu na nárast čerstvej hmoty, aj obsahu syntetizovaného chlorofylu v nadzemnej časti kukuřice /Zea mays L./Phytotoxicity test of the compound according to the invention and its effect on the growth of fresh mass and the content of synthesized chlorophyll in the above-ground part of maize (Zea mays L.)
Tabulka a) k příkladu 3Table a) to Example 3
Vplyv zlúčeniny podlá vynálezu na prolongačný rast koreňov a stoniek kukuřice (Zea maysEffect of Compound of the Invention on Prolongation Growth of Corn Roots and Stems (Zea mays
I./ po 72 hodinovej inkubácii v trne, vyjádřený v percentách kontrolnej vzorkyI. / after 72 hours of thorn incubation as a percentage of control
Pytotoxicita zlúčeniny podlá vynálezu sa hodnotila meranim prolongačného rastu kořena a stonky kukuřice /Zea mays L./ /Murín, A., Koleková, A., Váchová, M. a Bagula, Š., Biológja /Bratislava/ 35, 937 (1980), Sekerka, V. a Sutoris, V., Polnohospodárstvo 31.Pytotoxicity of the compound of the invention was evaluated by measuring the prolongation growth of corn root and stems (Zea mays L.) / Murin, A., Kolekova, A., Vachova, M. and Bagula, S., Biologja / Bratislava / 35, 937 (1980) , Sekerka, V. and Sutoris, V., Agriculture 31.
872 (1985)/.872 (1985)].
Semená kukuřice sa napučiavali vo vodných roztokoch zlúčenin podlá vynálezu o koncentrácii 1.10“5 ag mol.dm24 hodin, potom sa uložili na filtračný papier navlhčený příslušnými roztokmi testovaných koncentrácii a předkličovali sa v trne po dobu 72 hodin při izbovej teplote, pričom stočené válce filtračného papiera boli umiestnené v perforovaných polyetylénových sáčkoch /ČSC 46 0610/. Po uplynutí tejto doby sa merala dížka koreňov a nadzemnej časti rastliny. Výsledky sa vyhodnocovali v percentách kontrolnej vzorky. Vzhladom na nízku rozpustnost zlúčeniny podlá vynálezu vo vodě, sa testované koncentrácie připravovali z jej roztoku v N.N' dimetylformamide o koncentráciiCorn seeds were swelled in aqueous solutions of the compounds of the invention at a concentration of 1.10-5 and g mol.dm24 hours, then deposited on filter paper moistened with appropriate solutions of the test concentrations and precleaned in a mandrel for 72 hours at room temperature, paper were placed in perforated polyethylene bags (CSC 46 0610). After this time, the length of the roots and aboveground part of the plant was measured. Results were evaluated as a percentage of control. Because of the low water solubility of the compound of the invention, the concentrations tested were prepared from its solution in NN 'dimethylformamide at a concentration of
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS569789A CS272749B1 (en) | 1989-10-09 | 1989-10-09 | 3-/2-hydroxyethyl/-6-nitro-2-benzothiazolinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS569789A CS272749B1 (en) | 1989-10-09 | 1989-10-09 | 3-/2-hydroxyethyl/-6-nitro-2-benzothiazolinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS569789A1 CS569789A1 (en) | 1990-05-14 |
| CS272749B1 true CS272749B1 (en) | 1991-02-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS569789A CS272749B1 (en) | 1989-10-09 | 1989-10-09 | 3-/2-hydroxyethyl/-6-nitro-2-benzothiazolinone |
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| Country | Link |
|---|---|
| CS (1) | CS272749B1 (en) |
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1989
- 1989-10-09 CS CS569789A patent/CS272749B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS569789A1 (en) | 1990-05-14 |
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