CS233443B1 - 2-alkoxycarbonylmethyltio-3-alkylebenzotiazoline salts and method of its production - Google Patents

Abstract

The present invention provides a method for preparing novel substances 2-alkoxycarbonylmethylthio-3-alkylbenzothiazolium salts of formula I wherein R is methoxy, ethoxy, propoxy, isopropoxy, allyloxy; Ir represents methyl, ethyl, allyl, propyl, butyl, benzyl and X "mean bromine. The nature of the method for preparing substances according to the invention of the invention consists in the fact that the 3-R-2-derivatives -benzothiazolline, where K 'is the same as in formula I, they react with XCHgCOR, where R and X is the same as in Formula I in the environment organic solvents such as nitromethane, lower aliphatic ketones, tetrahydrofuran and acetonitrile at 18 ° C to 85 ° C for 2 to 96 hours. The compounds of the invention are effective as stimulators or plant growth inhibitors.

Description

The invention relates to 2-alkoxycarbonylmethylthio-3-alkylbenzothiazolium salts of the general formula I

N - R ¹ sch ₂ cor wherein K represents methoxy, ethoxy, propoxy, isopropoxy, allyloxy;

R ¹ is methyl, ethyl, allyl, propyl, butyl, benzyl and

X is bromine and epdsob of preparation.

Synthesis of banzotlazole salts using benzothiazole and 2-alkylbenzothiazole, reep.

Attention was paid to the 4- or 5-substituted benzothiazole in the works (Sutoria V, Halgai J., Sekerka V .: AO 223 426j Halgas J., Sutoria V, Sekerka V .: PV 7434-82; Sutoria V. , Halgai J., Sekerka Vs PV 688-82). Prepared bezothiazolium salts pre-exerted dampening effects (Sutoria V, Sekerka V, Halgai J .: 225 008) Antlmlobic activity on Staphylococcue O * bacteria (Sutorie V, Foltinova P., Halgai J .: PV 8540-82) and increases sugar content in eukor producing plants (Sutoria V., Sekerka V., Halgaš J.,

Bajči P, PV 2928-82).

The preparation of 2-alkylthio-3-alkylalkylbenzothiazolium salts has hitherto been addressed in the context of the Stem of their stability (Sexton WA: J. Chem. Soc. 1939, 470; Bradlov HL, Vanderwerf CA: J. Org. Chem. 16,11143 ( 1951); Bellenson B., Hamer FH: J. Chem. Soc. It has been found that the reaction of 2-alkylthiobenzothlasoles with an alkyl halide whose alkyl group is different from the alkyl group in the alkylthiobenzotlazole results in the interchange of alkyl groups and the synthesis products as a mixture of quaternary salts (Fry DJ, Kendall JD: J. Chem. Soc. 1951, 1). 716). It is believed that the exchange of alkyl groups is due to the formation of a transient eulfonium compound (Hoore C.Q., Wight E. S .: J. Chem. Soc. 1952, 4,237). When the alkyl groups are the same, weak and uniform product of the quaternary salt. The structurally definable 2-alkylthio-3-alkylbenzothiasol salts can be prepared by treating the alkyl halides with 3-alkyl-2-benzothiazolinothiones, which can be prepared by heating 2-alkylthiobenzotlazole in the presence of iodine. Pretayk is dependent on the nature of the alkyl and the reaction time (Sexton, V. A., J. Chem. Soc. 1939, 470; Hoore C.O., tfalght E. S., J. Chem. Soc. 1952, 4,237). The formation of 3-eubetituated-2-thioxobenzotlazoline compounds has been found in the study of the llichael and Mannich reactions of 2-mercaptobenzothiazole (Halaea, A.F., Smlth, O.E.P .: J. Org., Chea. 36, 636 (1971)) e.g. and methyl vinyl ketone, acrylonitrile, vinyl phenyl ketone, 2- and 4-vinylpyridine and the like. The 2-alkoxycarbonylmethyltlo-3-alkylbenzothiazolium salts of the present invention have not been described in the literature to date. Similar stamina of biological efficacy has not been paid attention within a timely period.

The process for the preparation of the compounds according to the invention consists in that the derivatives of 3-R ¹ -2-benzothiazolinothione of the formula II

where R ¹ is the same as in formula I, and XCHgCOR, where R and X is the same as in formula I in the environment of organic surfactants such as nitromethane, lower aliphatic ketones, tetrahydrofuran and aeetonltr11, at 18 to 85 ° C for 2 to 96 hours. The reaction is indicated by the following scheme:

(eg, xch, co) wherein R, R ¹ and X are as defined above.

General procedures for quaternization of 3-R ¹ -2-benzothiasolinothione.

EXAMPLE

0.02 moles of 3-substituted-2-benzothiazolintion and 0.025 moles of the corresponding bromoacetic acid dietary salt e are dissolved in 15-1 nitroethane. The reaction mixture is allowed to stand at 8 to 23 ° C for 96 hours. The precipitated quaternary salt was crystals washed with tetrahydrofuran and methanol (3: 1) or washed with acetone.

Example 2

0.02 mol of 3-substituted-2-benxothiazolintion and 0.025 mol of inc. The bromoacetic acid smear was dissolved in 15 ml of nitromethane. The reaction mixture was heated at 65-70 ° C for 2 hours. When the product did not crystallize upon cooling, ether (5 ml) was added. The crystalline fraction aa was washed on the filter with acetone or crystallized from tetrahydrofuran / methanol (~ 3: 1).

Example 3

0.02 mol of 3-8-substituted-2-benzotlasolintlone and 0.03 mol prial. of a salt of bromoacetic acid aa is dissolved in 15 ml of acetone or tetrahydrofuran. The reaction mixture was heated at 65-70 ° C for 20 hours. After cooling, the crystalline fraction was washed with acetone. Example 4

Dissolve 5.1 e (0 * 02 mol) of 3-benzyl-2-benzothlazolintione and 0.03 mol of the corresponding bromoacetate ester in 25 ml of nitroethane. The reaction mixture aa is heated at 80-85 ° C for 96 hours. The precipitated quaternary salt was crystallized with taken up with tetrahydrofuran and methanol (3: 1).

The results of the elemental analysis according to the invention and the physico-chemical constants of the synthesized compounds are shown in Table 1.

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Explanation:

C 2-MethoxycarbonylBethylthio-3-ethylbensothiasolium bromide

II 2-Ethoxycarbonylmethylthio-3-methylbenzothiasolabroaid

III * 2-Fropoxycarbonylaethylthio-3-ethylbesothiasolium bromide

IV 2-Ixopropoxycarbonylaethylthio-3-methylbenzothiasolumbroaid

V 2-Allyloxycarbonylmethyltlo-3-methylbenzothiazolium bromide

VI 2-Methoxycarbonylmethylthio-3-ethylbenzotlasolium bromide

VII 2-methoxycarbonylmethyltlo-3-ethylbenzothiazolium bromide

VIII 2-Propoxycarbonylaethylthio-3-ethylbenzothiazoliumabroaid

IX 2-Isopropoxycarbonylmethylthio-3-ethylbenzothiazolium bromide

X 2-Allyloxycarbonylmethylthio-3-ethylbenzothiasolium bromide

XI 2-Methoxycarbonylaethylthio-3-propylbenzothiazolium bromide

XII 2- (6-methoxycarbonylaethylthio-3-propylbensothiasolium bromide)

XIII 2-Fropoxycarbonylmethylthio-3-propylbenzothiasolumbroald

XIV 2-Isopropoxycarbonylmethylthio-3-propylbenzothiaxiolumbroaid

XV 2-Allyloxycarbonylmethylthio-3-propylbenzothiazolium bromide

XVI · 2-Methoxycarbonylmethyltlo-3-allylbenzothiazolium bromide

XVII 2-Ethoxycarbonylmethylthio-3-allylbensothiazoliumumbroaid

XVIII 2-Methoxycarbonylmethyltlo-3-butylbenxotlasolium bromide

XIX 2-Ethoxycarbonylaethyltlo-3-butylbenzothiazoliumumbroald

XX 2-Fropoxycarbonylmethylthio-3-butylbenzothesolium bromide

XXI 2-Allyloxycarbonylaethylthio-3-butylbenzothiazolium bromide

XXII 2-Methoxycarbonylmethyl -lo-3-benzylbenzothlazolium bromide.

XXIII 2-methoxycarbenylmethylthio-3-benzylbenzothiazolium bromide 1 H-NMR spectra were recorded on a TESLA BS 487 A instrument at 80 MHz in deuterated trifluoroacetic acid, internal standard hexaaethyldisiloxane.

Unwrought 1 H NMR chemical shifts of 6-2-alkylthio-3-alkylbenzothiazolium salts aynthesized according to the invention m - aultiplet q - quartet s - singlet p - quintet d - doublet sex - sextet t - triplet h - septet

I. 2-Methoxycarbonylmethylthio-3-methylbenzothiazolium bromide:

7.2 to 7.9 (a, 4 H, ar.), 3.88 (s, 3 H, and N-CH 2), 4.19 (s, 2 H, -S-CH ₂ -), 4.80 (s, 3H,

-o-ch ₃ ).

II. 2-ethoxycarbonylmethylthio-3-metylbenzetiasóliumbroaid:

7.2 to 7.9 (m, 4 H, ar.), 3.87 (s, 3 H, 5 s-CH), 4.16 (s, 2H, -S-CH ₂ -) 4 01 (q, 2 U, O-CHj-), 0.95 (t, 3H, CH _3).

III. 2-propoxykarbonylaetyltlp-3-metylbenzotiasóliUBbromid:

7.2-7.9 (m, 4H, ar.), 3.87 (s, 3H, n-CH3), 4.18 (s, 2H, -S-CH3-), 93 (t, 2 H, -O-GH ₂ -), 1.36 (sex, 2H, _--CH2 -), 0.65 (t, 3H, CH _3).

IV. 2-izopropoxykarbonylmetyltlo-3-aetylbenzotiaxóliumbromid:

7.2-7.9 (m, 4H, ar.), 3.86 (s, 3H, 1H-CH3), 4.13 (s, 2H, -S-CH2-), 85 (h, 1H, -CH3), 0.96 (d, 6H, -CH3).

V. 2-Allyloxycarbonylmethylthio-3-methylbeneothiazolium bromide:

7.2 to 7.9 (m, 4 H, ar.), 3.88 (s, 3H, 5H-CH _3), 4.20 (s, 2H, -S-CH ₂ -) 4 , 43 (d, 2H, _-O-CH2 -), 5.5 (m, 1H, »CH), 5.0 (m, 2H, _CH2).

VI. 2-aetoxykarbonylaetyltio-3-etylbenzotiasóliuBbro * id:

7.2 and 7.9 (a, 4H, ar.), 4.38 (q, 2H, S-CH3-), 1.25 (t, 3H, -CH3), 4.20 (t, 3H, -CH3-) · 2 H

-S-CH _{3 -} , 3.56 (s, 3 H, -O-CH ₃ ).

VII. 2-etoxykarbonylaetyltlo-3-etylbenzotiazóliuabroaid:

7.2 and 7.9 (a, 4H, ar.), 4.38 (q, 2H, -A-CH3-), 1.25 (t, 3H, -CH3), 4.21 ( a, 2 B,

-S-CH ₂ -), 4.03 (q, 2H, -OCH ₂ -), 0.98 (t, 3 H, -CH 3).

. VIII. 2-propoxykarbonylaetyltio-3-etylbenzotiazóllumbroaid:

7.2 to 7.9 (a, 4H, ar.), 4.40 (q, 2H, s-CH3), 1.25 (t, 3H, -CH3 ₎ , 4.24 ( a, 2 H,

_-S-CH2 -), 3.94 (t, 2H, _-O-CH2 -), 1.38 (sex, 2H, _--CH2 -), 0.63 (t, 3H, - CH).

IX. 2-lzopropoxykarbonylmetyltio-3-etylbenzotiazóliumbronid:

7.2 to 7.9 (and, R H, ar.), 4.38 (q, 2H, »i-CH ₂ -), 1.23 (t, 3H, -CH), 4.15 ( s, 2 H,

_-S-CH2 -), 4.81 (h, 1H, CH '), 0.98 (d, 6H, -CH).

X. 2-Allyloxycarbonylaethylthio-3-ethylbenzothiazoliumabroaid:

7.2 to 7.9 (s, 4 H, ar.), 4.43 (s, 4H, Si-CH ₂ -, _-0-CH2 -), 1.25 (t, 3H, - CO 3), 4.23 (s, 2 H, -S-CH ₂ -), 5.5 (a, 1 H, 2 -CH-).

XI. 2-metoxykarbonylmetyltio-3-propylbenzotiazóliuabromid:

7.2 to 7.9 (s, 4 H, ar.), 4.28 (t, 2H, »i-CH ₂ -), 1.70 (sex, 2H, -CHgr) and 0.73 (t, 3H,

CH _3), 4.20 (s, 2H, _-S-CH2 -), 3.59 (s, 3 H, -OC).

XII. 2-ethoxycarbonylmethylthio-3-propylbenzotiazóliuabroaid :.

7.2-7.9 (a, 4H, ar.), 4.29 (t, 2H, s1-CH2-), 1.70 (sex, 2H, -CH. -), 0, 73 (t, 3H,

-CH ₃ ), 4.20 (s, 2H, -S-CH ₂ -), 4.02 (q, 2H, -O-CH ₂ -), 0.95 (t, 3 H, -O- CH ₃ ).

XIII. 2-propoxykarbonylaetyltio-3-propylbenzótiazóliumbroaid:

7.2-7.9 (a, 4H, ar.), 4.29 (t, 2H, [alpha] -CH3-), 1.70 (sex, 2H, -CHg-), 0.70 ( t, 6 H,

CH _3), 3.93 (t, 2 H, -O-CH ,, -), 1.36 (sex, 2H, _--CH2 -).

XIV. 2-isopropoxycarbonylaethylthio-3-propylbenzothiazolium bromide: i_

7.2 to 7.9 (a, 4 H, ar.), 4.28 (t, 2 H, W-CH ₂ -), 1.69 (sex, 2 H, -CH 2 -), 0 70 (t, 3H,

-Cl 4), 4.16 (s, 2H, -S-CH ₂ -), 4.85 (h, 1H, -O-CH 2 -), 0.94 (d, 6 H, -CH ₃₎ ).

XV. 2-alyloxykarbonylaetyltio-3-propylbenzotiazóliumbromld:

7.2 to 7.9 (s, 4 H, ar.), 4.30 (t, 2H, = i-CH ₂ -), 1.70 (sex, 2H, -C -), 0 73 (t, 3H,

-CH ₃ ), 4.23 (s, 2H, -S-CH ₂ -), 4.43 (d, 2H, -O-CH ₂ -), 5.5 (a, 1 H, »CH- ), 5.0 (s, 2H, _CH2).

XVI. 2-metoxykarbonylmetyltio-3-alylbenzotiazóliumbroaid:

7.2 to 7.9 (s, 4H, ar), 5.0 (s, 4 H, »i-CH ₂ -,-CH₂), 5.5 (s, 1H, -CH); 4.20 (s, 2H, _-S-CH2 -), 3.56 (s, 3 H, _-0-CH3).

XVIII. 2-aetoxykarbonylmetyltio-3-butylbenzotiazóliumbromid:

7.2 to 7.9 (s, 4 H, ar.), 4.33 (t, 2H, »S-CH ₂ -), 1.7 (s, 2H, _-CH2 -), 1 , 2 (s, 2H, CH ₂ "-), 0.63 (t, 3H, CH _3), 4.20 (s, 2H, _-S-CH2 -), 3.56 ( s, 3 H, -O-CH3).

XIX. 2-etoxykarbonylaetyltio-3-butylbenzotiazóliuabroaid:

7.2 to 7.9 (a, 4H, ar.), 4.31 (t, 2H, sft-CHg-), 1.6 (a, 2H, -CHg), 1.3 to 0 5 (a, SH, -CH ₂ -, -CH ₃ ), 4.19 (s, 2H, -S-CH ₂ -), 4.02 (q, 2H, -O-CH ₂ - ).

XX. 2-propoxykarbonylaetyltio-3-butyÍbenzotiazóliuabroaid:

7.2 to 7.9 (s, 4 H, ar.), 4.35 (t, 2H, _Si-CH2 -), 1.8 to 1.0 (s, 6 H, _-CH2 - ), 0.63 (t, 6H, CH _3), 4.26 (s, 2H, _-S-CH2 ~), 3.94 (t, 2H, O-CHg-).

23J443 8

XXI. 2-alyloxykarbonylmetyltio-3-butylbenzotiazóliumbromld:

7.2-7.9 (m, 4H, ar.), 4.33 (t, 2H, 3-CH ₂ -), 1.6 (m, 2H, -CH ₂ -), 1 1 (m, 2H, -CH 2 -), 0.63 (t, 3 H, -CH 2), 4.24 (a, 2H, -S-Cl 2 -), 4.43 (d, 2 H, -O-CH 2 -), 5.5 (· 1 H, CH 2),

5.0 (a, 2H, -O ').

XXII. 2-metoxykarbonylmetyltlo-3-bensylbenzotiasólluabraBld:

7.2 to 7.9 (m, 4 H, ar.), 5.52 (t, 2H, _{5 ft-CH2} -), 4.25 (s, 2H, _-S-CH2 ~) .

XXIII. 2-etoxykarbonylmetyltlo-3-benzylbensotiaBÓliuBbroBÍd:

7.2-7.9 (m, 4H, ar.), 5.52 (t, 2H, [alpha] -CH3-), 4.25 (a, 2H, -S-CH2).

The substances according to the invention are effective as stimulators or inhibitors of plant growth. The bastion tests were carried out by the authors using a codified method on the vetch. Example 4 illustrates how to test the compounds of the invention for stimulatory and inhibitory activity.

Example 4

Grape wolf seeds germinated in Petrl dishes in a thermostate in a thorn at 25 ° C. Germs after 48-hour growth were exposed in molar solutions of 2-R-3-R'-substituted benzothiazolium salts, where R, R * and X- according to the general formula are given in I to XXIII, Table 1 in a 10 ° C concentration rock. ⁶ to 10 ^-1 mol.dm ^-3 . P ₀ 24 hours was determined inkubácle príraatok the extension of root growth. For each assay, a raster affection was also performed in the control series, the width of the test and control sets, and the significance between sets was determined biometrically.

Beta-indulylacetic acid (IAA), 2,4-difluorophenoxyacetic acid (2,4-D) and 2-chloroacetyltrimethylammonium chloride (CCC) were tested as standards. The results of the stimulatory and inhibitory effect of the synthesized compounds of the invention are shown in Table 2.

TabuTka2

Stimulatory and inhibitory effect of the synthesized compounds of the invention

fiíslo R r ' X stimulation + Bua mol.dm ^-3 inhibition · -a - mol.dm ' I II OCH ₃ OC ₂ H5 CH ₃ CH ₃ , 1 br br 7.15 4.05 io ^'1 10' ^{7 13 '13} III OC3Í4 CH ₃ br 3.55 IV OC ^ -i CH ₃ br 5.50 10 “ ⁹ . 10 ' ³ in OCH ₂ CH ₃ CH ₃ ch ₃ br , 0- ⁷ 5.15 VI VII OCH ₃ C ₂ H5 c ₂ h ₅ 0 ₂ Π ₅ br br 3.85 4.9 10- ' ³ VIII OC ₃ H7 .¾¾ br 21.60 10 ^-3 IX OCjtty-i C ₂ H5 br 2.00 10-5 1.50 10 ^'13 10 ^- ' ³ X and ₉ ch-ch ₂ ^C 2 ^H 5 br 4.30 XI OCH ₃ 5¾ br XII oc ₂ H5 5H7 br 1.55 10 ^-7 XIII 00 ₃ Η7 br 2.55 10 ^{9 9} 10 ~ ⁿ 10 ^-13 XIV OC ^ -i ^C 3 '7 br 3.80 XV och ₂ ch «ch ₂ · * 3 * 1 br 1.20 XVI OCH. CH, CH-CH, br 13.40 10- ³

Continuation of Table 2

Number R r ' X " stimulation + ^ Om mol.da "^ of inhibiting - w M XVII oc ₂ H5 ch ₂ ch »ch ₂ br XVIII OCitj, ^C 4 ^H 9 br 6.45 10 XIX • <* 2®5 c ₄ h ₉ br 3.10 10 ⁷ XX ^C 4 «9 br 23.70 10 XXI och ₂ ch «ch ₂ c ₄ h ₉ br 1.25 10 ⁹ 1.65 10 XXII och ₃ ch ₂ c ₆ h ₅ br 4.10 10 ' XXIII OC ₂ H5 br 6.00 10

Standard:

beta-indolylacetic acid (HA) 3.1 10 "^ 2,4-dichlorophenoxyacetic acid (2,4-D) 4.95 10" ®

2-chloroethyltrimethylamenium chloride (CCC) 3? 85 10?

Claims (3)

A 2-alkoxycarbonylmethylthio-3-alkylbenzothiazolium salt of the general formula I (I) wherein R represents a methoxy-, ethoxy-, propoxy- isopropoxy-, allyloxy group; r 'is methyl, ethyl, allyl, propyl, butyl, benzyl and X' is bromo. 2. A method according to claim 1, characterized in that the 3-R ^, -2-benzothiazolinone clone of formula II (II) where r1 is the same as in formula I, reacts β XCHgCOR, where R and X are the same as in formula Even in organic solvents such as nitromethane, lower aliphatic ketones, tetrahydrofuran and acetonitrile at 18 to 85 ° C for 2 to 96 hours.