Studies on Synthesis and Biological Activities of 2( 1 H21,2,42 Triazol212yl)2 2Arylthioethyl Substituted Phenyl Ketones
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1 , ACTA CHIMICA SINICA Vol. 60, 2002 No. 7, ( 1 H21,2, )2 2 ( ) Ξ Ξ 22(1 H21,2, ) (2) 1,42, 3,,. R 1, R 1 = (CH 3 ) 3 C, R 1 = Ar, Ar., 1,42,, Studies on Synthesis and Biological Activities of 2( 1 H21,2,42 Triazol212yl)2 2Arylthioethyl Substituted Phenyl Ketones CHEN, Wen2Bin ZHANG, Yao2Mou J IN, Gui2Yu Ξ ( State Key Laboratory of Elemento2Organic Chemistry, Institute of Elemento2Organic Chemistry, Nankai University, Tianjin ) Abstract The title compounds (3) have been prepared by 1,42nucleophilic addition of 22(1 H21,2,42triazol2 12yl ) 222propen212one with substituted thiophenol or heterocyclic compounds containing mercapto group. Structures of these compounds were characterized by elemental analysis, 1 H NMR and IR spectral data. The results of biological evaluation reveal that most of the compounds possess good fungicidal activities. The study of the relationship of structure and activity indicates that substituent R 1 has significant effect on biological activities of the compounds. Compounds 3 exhibit higher activity against Puccinia recondita in wheat when R 1 is (CH 3 ) 3 C, than when R 1 is Ar, while the substituents on group Ar have little effect on activities. Keywords triazole, 1,42nucleophilic addition, synthesis, biological activities,, 3,,, Scheme 1.., 1 [1 4 ],,, 1. 1 [5,6 1,42, ] 1 H NMR AC2P200,TMS, Ξ E2mail : com Received December 21, 2001 ; revised March 1, 2002 ; accepted April 4, (No ).
2 1304 Vol. 60, 2002 Scheme 1 MgSO 4, /, 3 (R 1 = Ar), 7818 % 9515 %., 1179 g (0101 mol) 22(1H2 1, 2, )24, (R 1 = (CH 3 ) 3 C) mol 30 ml, h,, 3 [ R 1 = (CH 3 ) 3 C], 7719 % 9516 %. 1 H NMR IR, 1, 2.,CDCl 3. MT23 C/ H/ N 2. IR NICOLET 5DX. X ,,. 2, [ R 1 = (CH 3 ) 3 C] 20 g (0115 mol) 2 (1) [ R 1 = Ac 2 O, 22(1 H21,2, )24,42 (CH 3 ) 3 C],33 ml 37 %,15 ml (2) [ R 1 = ( CH 100 ml, 4 h, 3 ) 3 C ]. 2,, 20 g (R 1 = Ar),Ogata [8 ] 2, 6717 %. (1) N, N, N, N 2 (TMDAM) 75 ml,, ( X 1 = Cl, Y = 44 % ;X h, 1 = F, Y = 26 %). 2,., 1,, / 133 Pa, 1210 g,, 6710 % (R 1 = Ar) 50 ml 2(1 H21,2, ) (1) ( R 1 = Ar) 0101 mol,30 ml, 0145 g (01015 mol), HCl,, 2 h,,,, 6214 % 6911 % ml (1 H21,2, ) (2) (R 1 = Ar) 110 mmol, 10 ml,, 112 mmol, 1 2 h, 20 ml 5 % NaOH,, 10 ml 3, , R 1 = (CH 3 ) 3 C, [7 ], 21 H21,2, )23, (1),
3 No. 7 : 2(1 H21,2, ) HCl,pH,.,, 1 115, 2 3 h,. 2 1 H NMR , 2, 1,42,,. R 1 ( t2bu Ar), R 1 = (CH 3 ) 3 C, 2 R 1 = Ar,,, (30 40 ), R 1 = Ar,,, [9 ],, R 1, R 2., HCl. 3 1 H ph 3 4,pH, NMR IR, 1, Table 1 The data of compounds 3 m. p. / Yield/ R 1 R 2 % 3a 42ClC 6 H 4 42ClC 6 H b 42ClC 6 H 4 42FC 6 H c 42ClC 6 H 4 42CH 3 C 6 H d 42ClC 6 H 4 C 6 H e C 6 H 5 42ClC 6 H f C 6 H 5 42CH 3 C 6 H g C 6 H 5 42FC 6 H h C 6 H 5 C 6 H i 42FC 6 H 4 C 6 H j 42FC 6 H 4 42CH 3 C 6 H k 42FC 6 H 4 42ClC 6 H l 42FC 6 H 4 42FC 6 H m 42BrC 6 H 4 42ClC 6 H Elemental analyses ( %, Calcd. ) C H N (53. 97) (3. 44) (11. 11) (56. 43) (3. 59) (11. 62) (60. 42) (4. 48) (11. 75) (59. 39) (4. 08) (12. 23) (59. 39) (4. 08) (12. 23) (66. 87) (5. 26) (13. 00) (62. 39) (4. 28) (12. 84) (66. 02) (4. 85) (13. 59) (62. 39) (4. 28) (12. 85) (63. 34) (4. 69) (12. 32) (56. 43) (3. 60) (11. 62) (59. 13) (3. 77) (12. 17) (48. 28) (3. 08) (9. 94)
4 1306 Vol. 60, 2002 m. p. / Yield/ R 1 R 2 % 3n (CH 3 ) 3 C C 6 H o (CH 3 ) 3 C 42ClC 6 H p (CH 3 ) 3 C 42CH 3 C 6 H q (CH 3 ) 3 C CH 2 C 6 H Thick 3r (CH 3 ) 3 C R 3 liquid s (CH 3 ) 3 C R t (CH 3 ) 3 C R u (CH 3 ) 3 C R Thick 3v (CH 3 ) 3 C R 7 liquid w (CH 3 ) 3 C R x (CH 3 ) 3 C R P Elemental analyses ( %, Calcd. ) C H N (62. 25) (6. 62) (14. 52) (55. 63) (5. 60) (12. 98) (63. 33) (6. 98) (13. 85) (63. 33) (6. 98) (13. 85) (66. 85) (8. 08) (11. 69) (56. 40) (6. 63) (21. 92) (57. 63) (6. 95) (21. 00) (58. 36) (5. 99) (22. 68) (57. 00) (6. 00) (21. 00) (59. 35) (6. 29) (21. 86) (55. 47) (5. 24) (16. 17) 2 3 IR 1 H NMR Table 2 IR and 1 H NMR data of compounds 3 IR ( / cm - 1, KBr) C O C N (Tr) C H (Tr) 1 H NMR (CDCl 3 / TMS), J H2H (Hz) 3a , b , (d, J = 7105, 2H, CH 2 S), 6124 (t, 1H, CH), (m, 4H, C 6 H 4 ), (m, 4H, C 6 H 4 ), 8113 (s, 1H, TrH), 9161 (s, 1H, TrH) (m, 2H, CH 2 S), (m, 1H, CH), (m, 4H, C 6 H 4 ), (m, 4H, C 6 H 4 ), 7198 (s, 1H, TrH), 8183 (s, 1H, TrH)
5 No. 7 : 2(1 H21,2, ) IR ( / cm - 1, KBr) C O C N (Tr) C H (Tr) 1 H NMR (CDCl 3 / TMS), J H2H (Hz) 3c , d , e , f , g , h , i , j , k , l , m , n , (s, 3H, CH 3 ), 3159 (dq, 2H, CH 2 S), 6106 (q, 1H, CH), (m, 4H, C 6 H 4 ), (m, 4H, C 6 H 4 ), 8103 (s, 1H, TrH), 8199 (s, 1H, TrH) 3163 (dq, 2H, CH 2 S), 6101 (q, 1H, CH), 7130 (s, 5H, C 6 H 5 ), (m, 4H, C 6 H 4 ), 7192 (s, 1H, TrH), 8152 (s, 1H, TrH) 3161 ( dq, 2H, CH 2 S), 6105 ( q, 1H, CH), (m, 4H, C 6 H 4 ), (m, 5H, C 6 H 5 ), 7192 ( s, 1H, TrH), 8152 (s, 1H, TrH) 2133 (s, 3H, CH 3 ), 3159 (dq, 2H, CH 2 S), 6108 (q, 1H, CH), (m, 4H, C 6 H 4 ), (m, 5H, C 6 H 5 ), 7199 (s, 1H, TrH), 8176 (s, 1H, TrH) 3165 ( d, J = 6184, 2H, CH 2 S), 6124 ( t, 1H, CH), (m, 9H, C 6 H 5, C 6 H 4 ), 8113 ( s, 1H, TrH), 9151 (s, 1H, TrH) 3164 (dq, 2H, CH 2 S), 6111 (q, 1H, CH), , , (m, 10H, 2 C 6 H 5 ), 7197 ( s, 1H, TrH), 8174 (s, 1H, TrH) 3167 ( d, 2H, J = 7108, CH 2 S), 6118 ( t, 1H, CH), , , ( m, 9H, C 6 H 4, C 6 H 5 ), 8106 (s, 1H, TrH), 9126 (s, 1H, TrH) 2133 (s, 3H, CH 3 ), 3161 (dq, 2H, CH 2 S), 6104 (q, 1H, CH), , (m, 8H, 2 C 6 H 4 ), 7199 (s, 1H, TrH), 8163 (s, 1H, TrH) 3164 (dq, 2H, CH 2 S), 6114 (q, 1H, CH), , , (m, 8H, 2 C 6 H 4 ), 8102 ( s, 1H, TrH), 9102 (s, 1H, TrH) 3163 ( d, 2H, J = 5165, CH 2 S), 6117 ( t, 1H, CH), , , (m, 8H, 2 C 6 H 4 ), 8104 (s, 1H, TrH), 9111 (s, 1H, TrH) 3164 ( dq, 2H, CH 2 S), 6111 ( q, 1H, CH), (m, 4H, C 6 H 4 ), (m, 4H, C 6 H 4 ), 8102 ( s, 1H, TrH), 9101 (s, 1H, TrH) 1105 ( s, 9H, ( CH 3 ) 3 C), ( m, 2H, CH 2 ), (t, 1H, CH), (m, 5H, C 6 H 5 ), 7191 (s, 1H, TrH), 8125 (s, 1H, TrH)
6 1308 Vol. 60, 2002 Compd1 IR ( / cm - 1, KBr) C O C N (Tr) C H (Tr) 1 H NMR (CDCl 3 / TMS), J H2H (Hz) 3o , p , ( s, 9H, ( CH 3 ) 3 C), ( m, 2H, CH 2 ), (t, 1H, CH), (m, 4H, C 6 H 4 ), 7188 (s, 1H, TrH), 8116 (s, 1H, TrH) 1101 (s, 9H, (CH 3 ) 3 C), 2128 ( s,3h,ch 3 ), (m, 2H, CH 2 ), (t, 1H, CH), (m, 4H, C 6 H 4 ),7188 (s, 1H, TrH), 8116 (s, 1H, TrH) 3q , ( s, 9H, ( CH 3 ) 3 C), ( m, 2H, CH 2 ), 3161, 3163 ( d, 2H, CH 2 ), (t, 1H, CH), (m, 5H, C 6 H 5 ),7190 (s, 1H, TrH), 8111 (s, 1H, TrH) 3r , s , t , (s, 9H, (CH 3 ) 3 C), 1130 (s, 9H, (CH 3 ) 3 C) (m, 2H, CH 2 ), 3159, 3161 ( d, 2H, CH 2 ) (t, 1H, CH), (m, 4H, C 6 H 4 ),7189 (s, 1H, TrH), 8132 (s, 1H, TrH) 1118 (s, 9H, (CH 3 ) 3 C), 2139 (s, 6H, 2 CH 3 ), (m, 2H, CH 2 ), (q, 1H, CH), 6174 (s, 1H,C 4 HN 2 ), 7191 (s, 1H, TrH), 8125 (s, 1H, TrH) 1117 ( s, 9H, (CH 3 ) 3 C), 2113 ( s, 3H, CH 3 ), 2143 ( s, 6H, 2 CH 3 ), (m, 2H, CH 2 ), (m, 1H, CH), 7192, 8133 (ds, 2H, 2 TrH) 3u , (s, 9H, (CH 3 ) 3 C), 2103 (s, 3H, CH 3 ), (m, 2H, CH 2 ), (t, 1H, CH), (m, 5H, C 6 H 5 ), 7190 (s, 1H, TrH), 8144 (s, 1H, TrH) 3v , ( s, 9H, (CH 3 ) 3 C), 2103 ( s, 3H, CH 3 ), 3164 ( s, 3H, OCH 3 ), (d, 2H, CH 2 ), (t, 1H, CH), (m, 4H, C 6 ), 7194 (s, 1H, TrH), 8154 (s, 1H, TrH) 3w , (s, 9H, (CH 3 ) 3 C), 2102 (s, 3H, CH 3 ), (m, 2H, CH 2 ), 5115 (s, 2H, CH 2 ), (t, 1H, CH), (m, 5H, C 6 H 5 ), 7179 ( s, 1H, TrH), 8136 (s, 1H, TrH) 3x , ( s, 9H, ( CH 3 ) 3 C), ( m, 2H, CH 2 ), (q, 1H, CH), (m, 4H, C 7 H 4 NS), 7190 (s, 1H, TrH), 8144 (s, 1H, TrH)
7 No. 7 : 2(1 H21,2, ) cm - 1, C H 3100 cm - 1,,, C N 1510 cm - 1, 3, 1480 cm - 1, 2 R 1 = Ar, 3f.. 80 %,, 3 ( ),, 3b, 3k,, CH 2 A ; R 1 = t2bu, ABX AB, 3, [10 ], 90 %,, ;, 60 % 90 % Table 3 The fungicidal activities against Puccinia recondita in wheat of compounds 3 (500) / % / % / % / % 3a 10 3g 20 3m 10 3s 100 3b 20 3h 40 3n 100 3t 100 3c 10 3i 20 3o 20 3u 100 3d 0 3j 10 3p 100 3v - 3e 0 3k 50 3q 0 3 w f 80 3l 30 3r 80 3x Table 4 The fungicidal activities of compounds 3 / % (500) (50) 3a b P c d k m Table 5 The fungicidal activities against R. Solani in rice of some compounds 3 (500) / % / % / % 3f p u k q v m s w n t x 62. 8
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