CS231212B1 - 2-R-3-R1 substituted benzothiazolium salt derivatives and processes for their preparation - Google Patents
2-R-3-R1 substituted benzothiazolium salt derivatives and processes for their preparation Download PDFInfo
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Abstract
Vynález sa týká nových látok 2^R-3-R substituovaných derivátov benzotiazóliových solí všeobecného vzorca I /■ (+) Podstata spdsobu přípravy látok podl’a vynálezu spočívá v tom, že derivát 2-R- -oenzotiazolu obecného vzorca II "2·θ—£ ” (ID reaguje so zlúčeninou obecného vzorca III r’x (III) Látky podl*e vynálezu mčžu nájsť uplatnenie ako agrochemikálie.The invention relates to new substances 2^R-3-R substituted derivatives of benzothiazolium salts of general formula I /■ (+) The essence of the method of preparing the substances according to the invention lies in the fact that the derivative of 2-R- -oensothiazole of general formula II "2·θ—£ ” (ID reacts with a compound of general formula III r’x (III) The substances according to the invention can find application as agrochemicals.
Description
231212 2
Vynález sa týká 2-R-3-R1 substituovaných derivátov benzotiazóliových solí obecnéhovzorce I
kde R znamená vodík, metyl; R1 znamená vodík, metyl, alyl, propargyl, butyl, etoxykarbonylmetyl, propoxykarbonylmetyl, alyloxykarbonylmetyl, benzyl, O / R znamená 4-metyl, 4-chlor, 6-metyl, 6-chlor a X znamená brómidovú, jódidovú, metylsulfátovú a hydrogensulfátovú skupinu a spSsobu leh přípravy. 2-R-3-R^-substituované benzotiazóliové soli a spčsob ich přípravy sú predmetomautorského osvedčenia č. 223 426. 2-R-3-R'-substituované deriváty benzotiazóliových solí podlá vynálezu nie sú v litera-tuře doteraz popísáné. Podobné žtúdiu biologickej účinnosti benzotiazóliových solí nebolado súčasnej doby věnovaná pozornost a len málo práč v tomto zmysle nachádzame u 2-substituo-vaných benzotiazóliových solí (Kendall J., Edwards H. D.: USA pat. 2 412 819; Chea. Abstr. 41. 5041 (1947); Garmalce D. L., Paris G. X., Komlossy J., Chambers C. H.,, Mc Grae R. C.: J. Med. Chem. 12.30 (1969)). Převážná část práč je věnovaná kondenzačným reakciám metylovej,resp. metylénovej skupině v polohe 2 s karbonylovými zlúčeninami a štúdiu priebehu reakclea reakčného prostredia (Deady 1. W.: Aust. J. Chem. 26. 1949 (1973); Deady L. W., Davis M.,Homfeld S., Aust. J. Chem. 27. 1917, 1221, (1974); Loches P., Meheux P., Neal J.: Bull.
Soc. Chim. Fr. 1968, 1093; Charbeurne D. J., Nunn A. J.: J. Chem. Soc. 1969, 4498).
Podstata spčsobu přípravy 2-R-3-R' substituovaných derivátov benzotiazóliových solipodl’a vynálezu spočívá v tom, že derivát 2-R-benzotiazólu obecného vzorca II, «ΜίθΰϊR (ID, o kde R a R majú význam uvedený hoře, reaguje so zlúčeninou obecného vzorca III, r’x (III), kde R1 a X majú význam uvedený hoře, v prostředí organických rozpúStadiel ako sú alifa-tické ketony s 1 až 4 atómami uhllka a dlmetylformamid, pri teplote 90 až 60 °C po dobu9 až 24 hodin.
Uvedená reakciu naznačuje nasledovná schéma:
kde R, r', R^ a x' je hoře uvedené 3 231212 Přikladl Všeobecný postup kvarternizácie benzotiazólu: 0,05 mol substituovaného benzotiazólua 0,06 mol halogénderivátu, resp. alkylsulfátu sa rozpustí v 12 ml bezvodej zmesi dimetyl-formamidu a acetonu (2:1). Reakčná zmes sa zahrieva na vodnom kúpeli s teplotou 50 až 60 °CAk po dvoch h nezačne krystalizovat kvartérna sol·, malé množstvo zmesi sa v skúmavke pre-myje petroléterom, potom acetónom a sklenou tyčinkou sa vyvolá kryštalizécia. Krystalickálátka sa vráti do reakčnej zmesi a pokračuje sa v zahrievaní óalšie 4 h. Po ochladeni sasol· odsaje, premyje bezvodým acetónom a krystalizuje z bezvodého tetrahydrofuránus 1 až 2 % metanolu. Výsledky elementérnej analýzy a fyzikálno-chemické konstanty syntetizovaných zlúčenínI - XVII sú uvedené v tabuTke 1. Látky podl’a vynálezu sú účinné ako inhibitory rastu.
Rastové testy boli realizované autormi modifikovanou metodou na modelovom objekteVika siata. Tento model bol vybraný pre vysokú homogenitu v klíčivosti semien a rastekllčencov. V sérii pokusov bola hl'adaná korelácia medzi štruktúrou, molaritou a biolo-gickou aktivitou. Příklad 2 bližšie osvetl’uje spfisob testovania zlúčenín I až XVII na inhibičnúúčinnost. Příklad 2 )
Semená Viky siatej sa nechajú klíčit v Petriho miskách v termostate v trne, pri 25 °C.
Klíčence po 48 h rastu boli exponované v molárnych roztokoch substituovaných benzetiazólío-i 2 vých solí, kde R, R , R a X podl’a všeobecného vzorce je uvedené v I až XVII tab. 1v koncentračnej škále 10”’^ až 10-’ M. Po 24 h inkubácii bol stanovený prírastok predTžo-vacieho rastu korenov. Pri každom stanovení bol uskutočnený aj rastový efekt v kontrolnejsérii. Šířka pokusného a kontrolného súboru, ako aj signifikantnosť medzi súbormi bolistanovené biometricky.
Ako Standard bol testovaný 2-chlóretyltrimetylamóniumchlorid (CGG). Výsledky inhi-bičného účinku zlúčenín I až XVII sú uvedené v tabuTke 2. 231212 4
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FokraSovanie tabulky
tA, OJ - to rn t—1 <7t ’Φ OJ OJ «a ,M Ol OJ 63 63 • >63 >63 • O >N O O *4 >64 P (0 (0 co CO <0 • 0 H O OJ σ\ σ» to O m c**· ·— OJ o co m to t- ’Φ O >N (0 OJ OJ Ol . 0 to to f* 0 0 Ot tO to to 10 lO to to f* S> XI)tí a oj ot C*~ Ol OJ O — f* OJ <- r*- «- 10 4) tO "Φ t- 10 10 t> 0 — OJ e* r- O <7\ 0 «- +>3£ a *« ·» Λ ~ u\ 0- to CO Ol OJ «— »— O\ « «. * 0 0 σ\ σ> O O\ 0 0 r— r~ σ\ Ot co w— «— e— «— N \ XD s pa Ή. — 0 Φ OJ to OJ "Φ ’Φ tO' 0 c- o- t* o\ t- 0 KJ# ia 10 «- 0 »- 0 01 «- μ· n Ol OJ co Ol m oj Ř s> Sot to ia 10 to *Φ ·φ ’Φ ’Φ ’Φ ’Φ ’Φ o r* Φ φ φ »- 00 t- Ol a to <J\ — co to to OJ — cq v- Ol 0 Ol OJ <x> a a a 1*1 v- Φ Φ φ m (0 5 m m 10 10 m m m m ’Φ Φ ’Φ φ φ co a 01 tO to m t- 10 m a c- ť- a f- co tO — 0 OJ 0 to cq OJ ΡΊ OJ r- a - to to to Ol ΓΊ Ol «“ r- ř- co od o> <A ř* t* t* t* <0 co to to M· *3· Μ- n m ’Φ ’Φ ’Φ ’Φ ’Φ IA 10 ΙΑ tO Λ tO ’ί· 10 ’Φ ia LA • Ol to OJ OJ 01 01 01 a ^J· Ol to 0 φ a 0 0 lO t* <n m J— Ol 01 Ol OJ Ol m m co m ΡΊ co co Ol 0 a co a a OJ OJ 0» >>o ω 0 0 0 co a fi Φ co a 0 a a a a * 0 a f-t a a & á tS á á a m ca to OJ ’Φ φ 3 > 00 W5 a a a a a a a a 0 m OJ m to lA o 0 0 0 0 o 0 O 1 X b k h k & © ta a a a a a a ro a o as a 1 OJ to co « H a O 1 OJ OJ 0 a a as 1 a » to aT o II o II to cn a a 10 8 0 0 a Ol OJ Ol 0 a a a 0 g 0 Ol 8 IA a IA a «a II 0 a 0 tO to Pí 0 σ» 0 0 O 0 0 0 Ol a Ol Ol OJ OJ Ol OJ a ’Φ a a a a a a « o o 0 0 o 0 0 /*> a 0 0 M a a a a a a H M * w H > H H n H H W H ► > > M H X X X X X X X »O 6 231212 Názov zlúčeniny: I Benzotiazóliumhydrogensulfát II 3-Metyl-4-metylbenzotiazóliumjodid III 3-Metyl-4-metylbenzotiazóliumbromid IV 3-Metyl-4-chlórbenzotiazóliummetosulfát V 3-Metyl-4-chlórbenzotiazóliumbromid VI 3-Metyl-6-chlórbenzotiazóliummetosulfát VII 3-Alylbenzotiazóliumjodid VIII 3-Alyl-4-metylbenzotiazóliumbromid IX 3-Alyl-6-metylbenzotiazóliumbromid X 3-Propargyl-6-nietylbenzotiazóliumbromld XI 3-Butylbenzotiazóliumbromid XII 3-Etoxykarbonylmetyl-6-chlórbenzotiazóliumbromid XIII 3-Propoxykarbonylmetyl-6-chlórbenzotiazóliumbromid XIV 3_Alyloxykarbonylmetylbenzotiazóliumbromid XV 3-Alyloxykarbonylmetyl-6-metylbenzotiazóliumbromid XVI 2-Metyl-3-benzylbenzotiazóliumbromid XVII 3-Benzyl-6-metylbenzotiazóliumbromid
Tabulka 2
Inhibičný účinok syntetizovaných zlúčenín podl’a vynálezu Číslo R R1 R2 X- Inhibicia (mm) M I II H H H CH3 H 4-CH3 HSO4 I 22,35 14,55 10'3 10‘3 III IV H H gh3 CH3 4-CH3 4-C1 Br ch3so4 14,60 19,20 10-3 10-3 10"3 v H CH, 4-C1 Br 19,15 VI VII VIII H H H CH3 CH2CH=CH2 ch2ch=ch2 6-C1 H 4-CHj ch3so4 I Br 5,65 20,00 7,40 10“3 10-3 10-3 IX H GH2CH=CH2 6-CH3 Br „ 10,00 ,0"3 10“’ 10“3 X XI H H ch2c=ch C4H9 H H Br Br 30,20 16,70 XII XIII H H CH2COOC2H5 C^C^COOCjfty 6-C1 H Br Br 9,80 2,00 10-3 10-13 XIV H ch?cooch;)ch=ch2 H Br 12,35 10-3 XV H gh?cooch?ch»gh2 6-CH3 Br 8,60 10-3 XVI gh3 ch2c6h5 H Br 3,00 10-5 XVII H ch2c6h5 6-CH3 Br 10,30 10“3
Standard: 2-ehlóretyltrimetylamóniumchlorid (CCG) 3,85 10-3 Látky podl’a vynálezu m6žu nájsť Široké uplatnenie v laboratórnej chemickej analýzea chemickom priemyšle, ale aj ako agrochemikálie.
231212 2
The invention relates to 2-R-3-R1 substituted benzothiazolium salt derivatives of general formula I
wherein R is hydrogen, methyl; R 1 is hydrogen, methyl, allyl, propargyl, butyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, allyloxycarbonylmethyl, benzyl, O / R is 4-methyl, 4-chloro, 6-methyl, 6-chloro and X is bromide, iodide, methylsulfate and hydrogen sulfate groups and the preparation process. The 2-R-3-R 6 -substituted benzothiazolium salts and the method for their preparation are the subject of Certificate No. 223 426. The 2-R-3-R'-substituted benzothiazolium salt derivatives of the present invention are not yet described in the literature. A similar study of the biological efficacy of the benzothiazolium salts or of the present day attention and little in this regard is found in the 2-substituted benzothiazole salts (Kendall J., Edwards HD: U.S. Pat. No. 2,412,819; Chea. Abstr. 41, 5041 ( Garmalce DL, Paris GX, Komlossy J, Chambers CH, Mc Grae RC, J. Med Chem, 12.30 (1969). The major part of the washing machine is devoted to the condensation reactions of methyl, respectively. methylene group at position 2 with carbonyl compounds and study of reaction medium reaction (Deady 1st W. Aust. J. Chem. 26, 1949 (1973); Deady LW, Davis M., Homfeld S., Aust. J. Chem 27, 1917, 1221, (1974), Loches P., Meheux P., Neal J .: Bull.
Soc. Chim. Fr. 1968, 1093; Charbeurne DJ, Nunn AJ: J. Chem. Soc. 1969, 4498).
The process for preparing 2-R-3-R 'substituted benzothiazolium salt derivatives according to the invention is characterized in that the 2-R-benzothiazole derivative of the general formula II, «ΜίθΰϊR (ID, o where R and R are as defined above, reacts with a compound of formula III, r'x (III), wherein R 1 and X are as defined above, in an organic solvent environment such as aliphatic ketones of 1 to 4 carbon atoms and dlmethylformamide, at 90 to 60 ° C for 9 to 24 hours.
The following scheme suggests the following response:
wherein R 1, R 2, R 4 and R 3 'are as defined in 231212 Example 1 General procedure for the benzothiazole quaternization: 0.05 mol of substituted benzothiazole and 0.06 mol halogeno derivative, respectively. The alkyl sulfate was dissolved in 12 mL of an anhydrous mixture of dimethylformamide and acetone (2: 1). The reaction mixture is heated in a 50-60 ° C water bath, and after two hours the quaternary salt does not crystallize, a small amount of the mixture is washed with petroleum ether, then with acetone and a glass rod to crystallize. The crystalline product is returned to the reaction mixture and heating is continued for a further 4 h. After cooling, the sassol is suctioned off, washed with anhydrous acetone and crystallized from anhydrous tetrahydrofuran to 1-2% methanol. The results of the elemental analysis and the physico-chemical constants of the synthesized compounds I-XVII are shown in Table 1. The compounds of the invention are effective as growth inhibitors.
Growth tests were carried out by the authors by a modified method on the model object Vika siata. This model was chosen for high homogeneity in seed germination and seedlings. In a series of experiments, a correlation was found between structure, molarity and biological activity. Example 2 further illustrates the method of testing compounds I to XVII for potency inhibition. Example 2)
Seeds of Sika seed are germinated in Petri dishes in a thermostate in a thorn, at 25 ° C.
Germs after 48 h growth were exposed in molar solutions of substituted benzethiazolium salts, where R, R, R and X according to the general formula are given in I to XVII tab. 1 in a concentration range of 10 µM to 10 µM. After 24 h incubation, the increase in preload growth of the roots was determined. A growth effect in the control series was also performed for each assay. The width of the test and control sets as well as the significance between the sets was biometrically determined.
2-Chloroethyltrimethylammonium chloride (CGG) was tested as a standard. The results of the inhibitory effect of compounds I to XVII are shown in Table 2. 231212 4
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Table Filling
,, - to to to 1 1 1 1 1 OJ OJ OJ OJ OJ 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 63 to »O mccccc OJccc · · · · · · · · · · · · · · · · · · · · · · · · í j j C * * OJ OJ O O O O O O O O O O O O O O O O - - - - "" 10 10 10 10 10 10 10 10 10 10 10 10 OJ A CO Ol Ol Ol Ol Ol Ol Ol Ol Ol----------co co co co co co co co co co co co co co «- N XD s pa - - 0 Φ to to""" Φ '''''0 0 0 0 0 0 0 J J J J J J J J J Co co 10 10 * 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 t- t- t- q q q q q q -Ol Ol Ol x ((((tO tO tO tO tO tO tO tO tO tO tO tO tO tO tO tO tO what - 0 OJ OJ OJ 0 «« «r co r r r--------· · · · · · · · 10- nm 'Φ' Φ 'Φ' Φ 'Φ IA 10 LA Ι' 10 '' • • • • • • • • • • • LA Ol to 01 01 01 01 01 J · to φ 01 0 0 0 — mm mm mm mm mm mm mm mm mm mm mm mm mm 01 01 01 01 01 ω ω 0 aaaa * 0 and ft aa & tS á φ>>3> 00 W5 aaaaaaaa 0 m OJ m to lA o 0 0 0 0 o 0 O 1 X bkhk & Aaaaaa ro aa a 1 o a o o o o o o o o o 0 aa a 1 o o aT o o o o o 0 o 0 a o 10 o 0 0 a o o o 0 aaa 0 g 0 o 8 aa a 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0/0> 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 H> HH n HHWH ►>> MHXXXXXXX »O 6 231212 Compound Name: I Benzothiazolium Hydrogen Sulfate II 3-Methyl-4-methylbenzothiazolium iodide III 3-Methyl-4-methylbenzothiazolium bromide IV 3-Methyl-4-chlorobenzothiazolium methoxide S 3-Methyl-4-chlorobenzothiazolium bromide VI 3-Methyl-6-chlorobenzothiazolium methosulfate VII 3-Allylbenzothiazolium iodide VIII 3-Allyl-4-methylbenzothiazolium bromide IX 3-Allyl-6-methylbenzothiazolium bromide X 3-Butylbenzothiazolium bromide XII 3-Ethoxycarbonylmethyl-6-chlorobenzothiazolium bromide XIII 3 -Propoxycarbonylmethyl-6-chlorobenzothiazolium bromide XIV 3-Allyloxycarbonylmethylbenzothiazolium bromide XV 3-Allyloxycarbonylmethyl-6-methylbenzothiazolium bromide XVI 2-Methyl-3-benzylbenzothium zolium bromide XVII 3-Benzyl-6-methylbenzothiazolium bromide
Table 2
Inhibitory effect of the synthesized compounds of the invention R 1 R 2 R 2 X- Inhibition (mm) MI II HHH CH 3 H 4-CH 3 HSO 4 I 22.35 14.55 10'3 10'3 III IV HH gh3 CH3 4-CH3 4- C1 Br ch3so4 14.60 19.20 10-3 10-3 10 "3 in H CH, 4-Cl Br 19.15 VI VII VIII HHH CH3 CH2CH = CH2 ch2ch = ch2 6-C1 H4-CH3 ch3so4 I Br 5,65 20,00 7,40 10 “3 10-3 10-3 IX H GH2CH = CH2 6-CH3 Br“ 10,00, 0 ”3 10“ 10 ”3 X XI HH ch2c = ch C4H9 HH Br Br 30.20 16.70 XII XIII HH CH2COOC2H5 C ^ C ^ COOCjfty 6-Cl H Br Br 9.80 2.00 10-3 10-13 XIV H chochoch;) ch = ch2 H Br 12.35 10 -3 XV H gh? Cooch? Ch »gh2 6-CH3 Br 8.60 10-3 XVI gh3 ch2c6h5 H Br 3.00 10-5 XVII H ch2c6h5 6-CH3 Br 10.30 10 '3
Standard: 2-chloroethyltrimethylammonium chloride (CCG) 3.85 10-3 The compounds of the invention may find wide application in the laboratory chemical analysis and chemical industry, but also as agrochemicals.
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| CN105461654A (en) * | 2015-12-01 | 2016-04-06 | 南京林业大学 | Benzothiazole ionic liquid and preparation method as well as application thereof |
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| CN105461654A (en) * | 2015-12-01 | 2016-04-06 | 南京林业大学 | Benzothiazole ionic liquid and preparation method as well as application thereof |
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| Publication number | Publication date |
|---|---|
| CS68882A1 (en) | 1984-03-20 |
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