SU849728A1 - 1-(buten-3-yl)-3-arylbenzo /f/ quinolines showing fungicide activity - Google Patents

Abstract

G- (Buten-3-ip) -3-arstbenzo (f) KHINOLINA general formula H2C-CH CH2 CH where, p -, OCH3, p-Br, o-OH, showing fungicidal activity. SL

Description

This invention relates to new chemical compounds of the benzo (- | -) quinoline series, namely, 1- (buten-3-yl) -3-arylbenzo () quinine of the general formula H C-CH-CHa-Gl d where, n-OCH5, p-B4, o-OH, which show fungicidal activity and can be used as chemical plant protection agents. Benzoquinoline derivatives are known to exhibit biological activity. Thus, the known anti-viral activity of the quaternary benzo () quinoline salts of the general formula HzC is where, n-F, n-Br, n-OCH ,, o-OH; . ,,.,.,,; , S04, Br, C104-L1. The closest to the proposed substance is the quaternary salt of ben30 () quinoline of the formula (CHAN4QhHC HC which has the properties of the regulator of the growth of the green mass of wheat and barley in the hydroponic method 51) equal to 0.40 mg per 1 kg of seeds, green mass is 128% by weight compared with the control. The purpose of the invention is to expand the arsenal of the medium affecting a living organism. The goal is achieved by new compounds - 1- (butene-3-sp ) - 3-arylbenzo () quinolines, obtained by catalytic condensation of arylidene-2 naphthylamine with allyl acetone. and IR spectra: P-mea r 1. The reaction mass of 2.31 g (0.01 mol) benzylidene-2 naphtylamine, 3.92 g (0.04 mol) of allyl acetone, 40 ml of zanol, 20 drops of nitrobenzene and 8 drops of concentrated hydrochloric acid vayut with stirring at a bath temperature of 60-70 C for 2 hours. After cooling, the precipitate Filter inrush, treated with 25% aqueous ammonia, washed with water and recrystallised from propan-2-ol. 1.2 g (39%) of 1- (buten-3-yl) -3 phenyl benzo (f) quinoline are obtained. M.p. 102103 ° C. Found,%: C 89.26; H 6.17; N 4.61. Sag N, s N. Calculated,%: C 89.28; H 6.19; N 4.52. 1- (Buten-3-yl) -3-phenylbenzo (f) quinoline is a white crystalline substance, readily soluble in alcohols, acetone, chloroform, carbon tetrachloride, dimethylformamide, dimethyl sulfoxide. Example 2. The reaction mass of 2.61 (0.01 mol) h - methoxybenzide iden - 2-naphtylamine, 3.92 g. (0.04 mol) of allylacetone, 40 ml of ethanol, 20 drops of nitrobenzene and 8 drops of concentrated hydrochloric acid are heated in an ampoule at 100 ° C for 5 hours. After cooling, the precipitated precipitate is filtered, treated with 25% aqueous ammonia, washed water and recrystall-. Is licensed from propan-2-ol. 1.2 g (35%) of 1- (buten-3-yl) -3 (p-methoxyphenyl) benzo) quinoline are obtained; mp. 111-112s. Found,%: C 85.19; H 6.24; N 4.12. 014.%, N0, Calculated,%: C 84.91; H 6.24; N 4.12. 1- (Wuten-3-yl) -3 - (- methoxyphenyl) benzo (i) quinoline is a white crystalline substance, well soluble in alcohols, acetone, chloroform, carbon tetrachloride, dimethylformamide, dimethyl sulfoxide. PRI me R 3. The reaction mass. from 3.10 g (0.01 mol) of h-bromobenzyl Icene-2-naphthylamine, 3.92 g (0.04 mol) of allyl acetone-, 80 ml of ethanol, 20 drops of nitrobenzene and 8 drops of concentrated hydrochloric acid on. they are heated with stirring at a bath temperature of 2 hours. After cooling, the precipitated precipitate is filtered off, treated with 25% aqueous ammonia, washed with water and recrystallized from propan-2-ol. 1.9 g (49%) of 1- (butene-3-Sh1) -3- (p-bromo phenyl) -benzo (1) quinoline are obtained, mp.109p c. Found,%: C, 71.17; H 4.98; Br 20.48; N 3.51. Cgj H, nd BrN S: C 71.14; H 4.68; Calculated, Br 20, -58; N- 3.60. 1- (Buten-3-yl) -3- (p-bromophenyl) benzo (i) quinoline is a white crystalline substance: the colors are readily soluble in alcohols, acetone, chloroform, tetrachloride, dimethylformamide, dimethyl sulfoxide. PRI me R 4. The reaction mass of 2.47 g (0.01 mol) o-hydroxybenzylidene-2-naphthylamine, 3.92 g (0.04 moles) of allyl acetone, 5 ml dimethylformamide, 8 drops of concentrated hydrochloric the acids are heated with stirring for 5 hours. After cooling, the precipitated precipitate is filtered off, recrystallized from prop. an-2-ol. Obtain 0.8 g (25%) of 1- (buten-3-yl) -3- (o-hydroxyphenyl) benzo (i) quinoline, so pl. 97-98 C. Found,%: C 84.62; H 5.79; N 4.13. C N. Calculated,%: C 84.88; H 5.90; N.4,30. 1- (Butene-3-yl) -3- (o-hydroxyphenyl) benzo (t) quinoline is a yellow crystalline substance, readily soluble in alcohols, acetone, chloroform, carbon tetrachloride, dimethylformamide, dimethyl sulfoxide ,. Tests of biological activity are shown. that the synthesized compounds exhibit fungicidal activity. The test results are shown in the table.

.NgS NS-NgS-NgS

, NgS NS-NgS-NgS

92

Vocv,

100

Vsr

10.0

State

.N C-NgS

TMTD (reference ,.

tetramethylthiuram disulfide)

Table continuation

Growth Suppression Z

bacteria

chitseli gri ba

Botrytic

Xanthomocinerea nas malvacearum

100

100

100

Claims (1)

G- (Buten-3-yl) -3-arylbenzo) quinolines of the general formula showing fungicidal activity.