Synthesis and Biological Activities of 1,2,4-Triazole Schiff Bases Containing Pyrazole Rings†

doi:10.7503/cjcu20150036

Abstract

Abstract:

An important class of compounds formed by 1,2,4-triazole and its derivatives were reported to exhibit a broad spectrum of biological activities. And pyrazole derivatives usually have antifungal, anticancer and herbicidal activities. The compounds containing 1,2,4-triazole and pyrazole would provide better biological activities simultaneously according biological activity of the superposition principle. In the present work, a series of novel 1,2,4-triazole Schiff bases containing pyrazole rings was synthesized by multistep reactions. Their structures were characterized by IR, ¹H NMR,¹³C NMR, HRMS, elemental analyses and X-ray diffraction techniques. The biological activities of the target compounds for the against four vegetable pathogens containing Gibberll nicotiancola, Gibberlla saubinetii, Fusarium oxysporium f. sp. niveum and Pythium solani were evaluated. The preliminary results indicated that most of the compounds exhibit relatively good antifungal activities, especially compounds G9, G10 and G15 showed better biological activity than triazolone.

Key words: Triazole, Pyrazole, Schiff base, Biological activity

CLC Number:

O626

TrendMD:

WANG Zijian, SUN Xiaohong, LIU Yuanfa, CHEN Bang, SHEN Shengqiang, JIN Ruyi, MA Haixia. Synthesis and Biological Activities of 1,2,4-Triazole Schiff Bases Containing Pyrazole Rings^†[J]. Chem. J. Chinese Universities, 2015, 36(7): 1315.

Figures/Tables 4

Scheme 1 Synthetic routes of compounds G1—G15

Table 1 Appearance, melting points, yields, HRMS, IR and elemental analysis data of compounds G1—G15

Compd.	Appearance	m.p./℃	Yield(%)	HRMS(ESI) [M+Na]⁺ (calcd.), m/z	IR(KBr), $ν ˙$ /cm^-1	Elemental analysis (%, calcd.)
Compd.	Appearance	m.p./℃	Yield(%)	HRMS(ESI) [M+Na]⁺ (calcd.), m/z	IR(KBr), $ν ˙$ /cm^-1	C	H	N
G1	White solid	242.2—242.7	65.3	365.1246 (365.1283)	3423(N—H), 3041(=C—H), 1583(C=N), 1352(C=S), 1415, 1495, 1583(C=C)	56.67 (56.14)	5.13 (5.26)	24.87 (24.56)
G2	Light yellow solid	243.5—244.2	72.1	364.1438 (364.1413)	3434(N—H), 3021(=C—H), 1585(C=N), 1369(C=S), 1430, 1482, 1529(C=C)	56.83 (56.30)	5.21 (5.57)	29.01 (28.74)
G3	Light yellow solid	254.6—255.8	66.4	369.0792 (369.0757)	3415(N—H), 3039(=C—H), 1594(C=N), 1341(C=S), 1428, 1486, 1556(C=C)	51.88 (52.02)	4.65 (4.34)	24.72 (24.28)
G4	White solid	249.7—250.4	58.7	349.1322 (349.1314)	3435(N—H), 3024(=C—H), 1598(C=N), 1344(C=S), 1419, 1486, 1554(C=C)	58.54 (58.90)	5.31 (5.52)	25.26 (25.77)
G5	White solid	273.2—274.1	70.6	351.1093 (351.1106)	3431(N—H), 3035(=C—H), 1588(C=N), 1346(C=S), 1422, 1485, 1552(C=C)	54.54 (54.88)	5.01 (4.88)	25.34 (25.61)
G6	White solid	244.3—245.5	66.5	381.1236 (381.1212)	3429(N—H), 3028(=C—H), 1592(C=N), 1348(C=S), 1422, 1483, 1541(C=C)	53.72 (53.63)	5.28 (5.03)	23.74 (23.46)
G7	Light yellow solid	246.1—247.3	68.1	425.1458 (425.1474)	3418(N—H), 3031(=C—H), 1594(C=N), 1346(C=S), 1420, 1471, 1562(C=C)	53.42 (53.73)	5.85 (5.47)	21.13 (20.90)
G8	White solid	238.5—239.3	55.2	381.1230 (381.1212)	3424(N—H), 3033(=C—H), 1588(C=N), 1452(C=S), 1418, 1477, 1548(C=C)	53.72 (53.63)	5.12 (5.03)	23.71 (23.46)
G9	Light yellow solid	99.6—100.5	74.4	425.0872 (425.0859)	3430(N—H), 3029(=C—H), 1594(C=N), 1356(C=S), 1426, 1471, 1566(C=C)	44.42 (44.78)	3.65 (3.48)	27.62 (27.86)
G10	Yellow solid	248.3—249.4	57.3	380.1032 (380.1008)	3432(N—H), 3033(=C—H), 1594(C=N), 1347(C=S), 1424, 1464, 1553(C=C)	50.71 (50.42)	4.42 (4.20)	27.86 (27.45)
G11	Yellow solid	199.5—200.8	64.7	353.1042 (353.1063)	3433(N—H), 3029(=C—H), 1596(C=N), 1350(C=S), 1423, 1471, 1563(C=C)	54.77 (54.55)	4.32 (4.55)	25.23 (25.45)
G12	White solid	230.2—231.5	59.2	349.1323 (349.1314)	3419(N—H), 3032(=C—H), 1588(C=N), 1348(C=S), 1426, 1478, 1544(C=C)	59.16 (58.90)	5.62 (5.52)	25.83 (25.77)
G13	Yellow solid	203.4—204.7	78.5	369.0795 (369.0757)	3438(N—H), 3027(=C—H), 1591(C=N), 1366(C=S), 1419, 1444, 1558(C=C)	52.32 (52.02)	4.32 (4.34)	24.56 (24.28)
G14	White solid	208.7—210.2	77.4	335.1088 (335.1157)	3423(N—H), 3035(=C—H), 1595(C=N), 1344(C=S), 1422, 1453, 1565(C=C)	57.88 (57.69)	5.31 (5.13)	27.11 (26.92)
G15	Yellow solid	240.5—242.3	67.9	387.0642 (387.0673)	3432(N—H), 3027(=C—H), 1589(C=N), 1355(C=S), 1422, 1471, 1561(C=C)	49.32 (49.45)	3.69 (3.85)	23.12 (23.08)

Table 1 Appearance, melting points, yields, HRMS, IR and elemental analysis data of compounds G1—G15

Compd.	Appearance	m.p./℃	Yield(%)	HRMS(ESI) [M+Na]⁺ (calcd.), m/z	IR(KBr), $ν ˙$ /cm^-1	Elemental analysis (%, calcd.)
Compd.	Appearance	m.p./℃	Yield(%)	HRMS(ESI) [M+Na]⁺ (calcd.), m/z	IR(KBr), $ν ˙$ /cm^-1	C	H	N
G1	White solid	242.2—242.7	65.3	365.1246 (365.1283)	3423(N—H), 3041(=C—H), 1583(C=N), 1352(C=S), 1415, 1495, 1583(C=C)	56.67 (56.14)	5.13 (5.26)	24.87 (24.56)
G2	Light yellow solid	243.5—244.2	72.1	364.1438 (364.1413)	3434(N—H), 3021(=C—H), 1585(C=N), 1369(C=S), 1430, 1482, 1529(C=C)	56.83 (56.30)	5.21 (5.57)	29.01 (28.74)
G3	Light yellow solid	254.6—255.8	66.4	369.0792 (369.0757)	3415(N—H), 3039(=C—H), 1594(C=N), 1341(C=S), 1428, 1486, 1556(C=C)	51.88 (52.02)	4.65 (4.34)	24.72 (24.28)
G4	White solid	249.7—250.4	58.7	349.1322 (349.1314)	3435(N—H), 3024(=C—H), 1598(C=N), 1344(C=S), 1419, 1486, 1554(C=C)	58.54 (58.90)	5.31 (5.52)	25.26 (25.77)
G5	White solid	273.2—274.1	70.6	351.1093 (351.1106)	3431(N—H), 3035(=C—H), 1588(C=N), 1346(C=S), 1422, 1485, 1552(C=C)	54.54 (54.88)	5.01 (4.88)	25.34 (25.61)
G6	White solid	244.3—245.5	66.5	381.1236 (381.1212)	3429(N—H), 3028(=C—H), 1592(C=N), 1348(C=S), 1422, 1483, 1541(C=C)	53.72 (53.63)	5.28 (5.03)	23.74 (23.46)
G7	Light yellow solid	246.1—247.3	68.1	425.1458 (425.1474)	3418(N—H), 3031(=C—H), 1594(C=N), 1346(C=S), 1420, 1471, 1562(C=C)	53.42 (53.73)	5.85 (5.47)	21.13 (20.90)
G8	White solid	238.5—239.3	55.2	381.1230 (381.1212)	3424(N—H), 3033(=C—H), 1588(C=N), 1452(C=S), 1418, 1477, 1548(C=C)	53.72 (53.63)	5.12 (5.03)	23.71 (23.46)
G9	Light yellow solid	99.6—100.5	74.4	425.0872 (425.0859)	3430(N—H), 3029(=C—H), 1594(C=N), 1356(C=S), 1426, 1471, 1566(C=C)	44.42 (44.78)	3.65 (3.48)	27.62 (27.86)
G10	Yellow solid	248.3—249.4	57.3	380.1032 (380.1008)	3432(N—H), 3033(=C—H), 1594(C=N), 1347(C=S), 1424, 1464, 1553(C=C)	50.71 (50.42)	4.42 (4.20)	27.86 (27.45)
G11	Yellow solid	199.5—200.8	64.7	353.1042 (353.1063)	3433(N—H), 3029(=C—H), 1596(C=N), 1350(C=S), 1423, 1471, 1563(C=C)	54.77 (54.55)	4.32 (4.55)	25.23 (25.45)
G12	White solid	230.2—231.5	59.2	349.1323 (349.1314)	3419(N—H), 3032(=C—H), 1588(C=N), 1348(C=S), 1426, 1478, 1544(C=C)	59.16 (58.90)	5.62 (5.52)	25.83 (25.77)
G13	Yellow solid	203.4—204.7	78.5	369.0795 (369.0757)	3438(N—H), 3027(=C—H), 1591(C=N), 1366(C=S), 1419, 1444, 1558(C=C)	52.32 (52.02)	4.32 (4.34)	24.56 (24.28)
G14	White solid	208.7—210.2	77.4	335.1088 (335.1157)	3423(N—H), 3035(=C—H), 1595(C=N), 1344(C=S), 1422, 1453, 1565(C=C)	57.88 (57.69)	5.31 (5.13)	27.11 (26.92)
G15	Yellow solid	240.5—242.3	67.9	387.0642 (387.0673)	3432(N—H), 3027(=C—H), 1589(C=N), 1355(C=S), 1422, 1471, 1561(C=C)	49.32 (49.45)	3.69 (3.85)	23.12 (23.08)

Table 2 1H NMR and 13C NMR data of compounds G1—G15

Compd.	¹H NMR(DMSO, 400 MHz), δ	¹³C NMR(DMSO, 100 MHz), δ
G1	2.01(s, 3H, Py—CH₃), 2.21(s, 3H, Py—CH₃), 3.72(s, 3H, OCH₃), 5.77(s, 1H, pyrazole), 5.31(s, 2H, CH₂), 7.12—7.82(m, 4H, phenyl), 9.52(s, 1H, CH =N)	164.65, 163.26, 162.21, 147.64, 147.19, 140.55, 130.32, 126.89, 115.17, 105.42, 52.35, 42.98, 13.64, 11.13
G2	2.32(s, 3H, Py—CH₃), 2.52(s, 3H, Py—CH₃), 6.06(s, 1H, pyrazole), 5.57(s, 2H, CH₂), 14.20(s, 1H, SH), 7.11—7.93(m, 4H, phenyl), 9.48(s, 1H, CH=N)	164.71, 162.52, 148.24, 147.80, 147.31, 140.39, 130.74, 123.32, 113.25, 105.36, 43.61, 26.88, 13.57, 11.23
G3	2.03(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.72(s, 1H, pyrazole), 5.33(s, 2H, CH₂), 14.13(s, 1H, SH), 7.46—7.76(m, 4H, phenyl), 9.72(s, 1H, CH=N)	163.96, 162.13, 147.73, 147.29, 140.38, 136.58, 131.26, 130.19, 129.43, 105.52, 43.33, 13.68, 11.15
G4	2.02(s, 3H, Py—CH₃), 2.21(s, 3H, Py—CH₃), 3.67(s, 3H, Ph—CH₃), 5.76(s, 1H, pyrazole), 5.38(s, 2H, CH₂), 14.11(s, 1H, SH), 7.23—7.61(m, 4H, phenyl), 9.87(s, 1H, CH=N)	164.82, 162.32, 147.56, 147.30, 143.63, 140.37, 130.17, 129.71, 129.18, 105.46, 43.08, 21.74, 13.74, 11.08
G5	2.01(s, 3H, Py—CH₃), 2.21(s, 3H, Py—CH₃), 10.15(s, 1H, OH), 5.71(s, 1H, pyrazole), 5.34(s, 2H, CH₂), 14.12(s, 1H, SH), 7.14—7.45(m, 4H, phenyl), 9.97(s, 1H, CH=N)	164.21, 162.37, 160.17, 147.82, 147.21, 140.58, 129.89, 126.11, 116.25, 105.61, 42.89, 13.35, 11.09
G6	2.02(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 3.83(s, 1H, Ph—CH₃), 5.76(s, 1H, pyrazole), 5.32(s, 2H, CH₂), 13.97(s, 1H, SH), 7.19—7.51(m, 3H, phenyl), 9.86(s, 1H, CH=N), 10.07(s, 1H, OH)	164.35, 162.41, 151.71, 148.08, 147.92, 147.34, 140.27, 126.94, 123.11, 117.25, 114.68, 105.56, 53.67, 43.12, 13.60, 11.14
G7	2.02(s, 3H, Py—CH₃), 2.25(s, 3H, Py—CH₃), 3.37, 3.76, 3.85(s, 3H, OCH₃), 5.79(s, 1H, pyrazole), 5.34(s, 2H, CH₂), 7.16—7.18(m, 2H, phenyl), 9.67(s, 1H, CH=N)	163.85, 161.91, 151.12, 147.92, 147.22, 141.63, 140.81, 128.34, 106.71, 105.46, 55.62, 55.49, 43.27, 13.39, 11.08
G8	2.02(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 3.85(s, 1H, Ph—CH₃), 5.78(s, 1H, pyrazole), 5.32(s, 2H, CH₂), 13.99(s, 1H, SH), 7.15—7.40(m, 3H, phenyl), 9.80(s, 1H, CH=N), 10.04(s, 1H, OH)	164.18, 161.97, 152.09, 150.13, 147.81, 147.23, 140.66, 123.32, 121.87, 120.45, 118.79, 105.38, 54.26, 43.09, 13.29, 11.26
G9	2.03(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.75(s, 1H, pyrazole), 5.33(s, 2H, CH₂), 7.23—7.61(m, 3H, Phenyl), 9.97(s, 1H, CH=N)	164.16, 162.42, 151.68, 149.57, 147.87, 147.23, 140.62, 133.19, 131.41, 127.48, 118.36, 105.72, 43.37, 13.32, 10.95
G10	2.02(s, 3H, Py—CH₃), 2.21(s, 3H, Py—CH₃), 5.77(s, 1H, pyrazole), 5.35(s, 2H, CH₂), 14.10(s, 1H, SH), 7.44—7.68(m, 4H, phenyl), 9.94(s, 1H, CH=N)	163.98, 162.12, 148.76, 147.73, 147.27, 140.61, 135.34, 134.62, 130.73, 124.34, 123.27, 105.47, 43.58, 13.69, 11.11
G11	2.02(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.79(s, 1H, pyrazole), 5.37(s, 2H, CH₂), 14.08(s, 1H, SH), 7.50—7.74(m, 4H, phenyl), 9.95(s, 1H, CH=N)	164.35, 163.31, 162.67, 147.69, 147.13, 140.78, 135.28, 130.83, 125.17, 118.01, 114.24, 105.27, 42.98, 13.81, 11.06
G12	2.02(s, 3H, Py—CH₃), 2.21(s, 3H, Py—CH₃), 3.64(s, 3H, Ph—CH₃), 5.76(s, 1H, pyrazole), 5.36(s, 2H, CH₂), 14.13(s, 1H, SH), 7.21—7.63(m, 4H, phenyl), 9.85(s, 1H, CH=N)	164.11, 161.87, 147.18, 146.84, 139.93, 138.51, 133.46, 131.95129.02, 128.98, 126.06, 105.05, 42.67, 20.82, 13.29, 10.63
G13	2.03(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.73(s, 1H, pyrazole), 5.34(s, 2H, CH₂), 7.44—7.72(m, 4H, phenyl), 9.74(s, 1H, CH=N)	162.34, 161.89, 147.74, 147.27, 140.32, 135.36, 134.38, 131.48, 130.62, 128.18, 127.98, 105.54, 43.21, 13.72, 11.07
G14	2.02(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.77(s, 1H, pyrazole), 5.36(s, 2H, CH₂), 14.09(s, 1H, SH), 7.21—7.73(m, 5H, phenyl), 9.66(s, 1H, CH=N)	164.56, 161.95, 147.98, 147.23, 140.15, 134.05, 131.23, 129.42, 128.37, 105.71, 43.42, 13.69, 11.10
G15	2.03(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.79(s, 1H, pyrazole), 5.32(s, 2H, CH₂), 14.11(s, 1H, SH), 7.46—7.68(m, 3H, phenyl), 10.58(s, 1H, CH=N)	164.18, 162.41, 161.07, 147.88, 147.12, 140.28, 135.41, 134.71, 125.25, 118.13, 113.47, 105.63, 43.47, 13.52, 10.89

Table 2 1H NMR and 13C NMR data of compounds G1—G15

Compd.	¹H NMR(DMSO, 400 MHz), δ	¹³C NMR(DMSO, 100 MHz), δ
G1	2.01(s, 3H, Py—CH₃), 2.21(s, 3H, Py—CH₃), 3.72(s, 3H, OCH₃), 5.77(s, 1H, pyrazole), 5.31(s, 2H, CH₂), 7.12—7.82(m, 4H, phenyl), 9.52(s, 1H, CH =N)	164.65, 163.26, 162.21, 147.64, 147.19, 140.55, 130.32, 126.89, 115.17, 105.42, 52.35, 42.98, 13.64, 11.13
G2	2.32(s, 3H, Py—CH₃), 2.52(s, 3H, Py—CH₃), 6.06(s, 1H, pyrazole), 5.57(s, 2H, CH₂), 14.20(s, 1H, SH), 7.11—7.93(m, 4H, phenyl), 9.48(s, 1H, CH=N)	164.71, 162.52, 148.24, 147.80, 147.31, 140.39, 130.74, 123.32, 113.25, 105.36, 43.61, 26.88, 13.57, 11.23
G3	2.03(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.72(s, 1H, pyrazole), 5.33(s, 2H, CH₂), 14.13(s, 1H, SH), 7.46—7.76(m, 4H, phenyl), 9.72(s, 1H, CH=N)	163.96, 162.13, 147.73, 147.29, 140.38, 136.58, 131.26, 130.19, 129.43, 105.52, 43.33, 13.68, 11.15
G4	2.02(s, 3H, Py—CH₃), 2.21(s, 3H, Py—CH₃), 3.67(s, 3H, Ph—CH₃), 5.76(s, 1H, pyrazole), 5.38(s, 2H, CH₂), 14.11(s, 1H, SH), 7.23—7.61(m, 4H, phenyl), 9.87(s, 1H, CH=N)	164.82, 162.32, 147.56, 147.30, 143.63, 140.37, 130.17, 129.71, 129.18, 105.46, 43.08, 21.74, 13.74, 11.08
G5	2.01(s, 3H, Py—CH₃), 2.21(s, 3H, Py—CH₃), 10.15(s, 1H, OH), 5.71(s, 1H, pyrazole), 5.34(s, 2H, CH₂), 14.12(s, 1H, SH), 7.14—7.45(m, 4H, phenyl), 9.97(s, 1H, CH=N)	164.21, 162.37, 160.17, 147.82, 147.21, 140.58, 129.89, 126.11, 116.25, 105.61, 42.89, 13.35, 11.09
G6	2.02(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 3.83(s, 1H, Ph—CH₃), 5.76(s, 1H, pyrazole), 5.32(s, 2H, CH₂), 13.97(s, 1H, SH), 7.19—7.51(m, 3H, phenyl), 9.86(s, 1H, CH=N), 10.07(s, 1H, OH)	164.35, 162.41, 151.71, 148.08, 147.92, 147.34, 140.27, 126.94, 123.11, 117.25, 114.68, 105.56, 53.67, 43.12, 13.60, 11.14
G7	2.02(s, 3H, Py—CH₃), 2.25(s, 3H, Py—CH₃), 3.37, 3.76, 3.85(s, 3H, OCH₃), 5.79(s, 1H, pyrazole), 5.34(s, 2H, CH₂), 7.16—7.18(m, 2H, phenyl), 9.67(s, 1H, CH=N)	163.85, 161.91, 151.12, 147.92, 147.22, 141.63, 140.81, 128.34, 106.71, 105.46, 55.62, 55.49, 43.27, 13.39, 11.08
G8	2.02(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 3.85(s, 1H, Ph—CH₃), 5.78(s, 1H, pyrazole), 5.32(s, 2H, CH₂), 13.99(s, 1H, SH), 7.15—7.40(m, 3H, phenyl), 9.80(s, 1H, CH=N), 10.04(s, 1H, OH)	164.18, 161.97, 152.09, 150.13, 147.81, 147.23, 140.66, 123.32, 121.87, 120.45, 118.79, 105.38, 54.26, 43.09, 13.29, 11.26
G9	2.03(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.75(s, 1H, pyrazole), 5.33(s, 2H, CH₂), 7.23—7.61(m, 3H, Phenyl), 9.97(s, 1H, CH=N)	164.16, 162.42, 151.68, 149.57, 147.87, 147.23, 140.62, 133.19, 131.41, 127.48, 118.36, 105.72, 43.37, 13.32, 10.95
G10	2.02(s, 3H, Py—CH₃), 2.21(s, 3H, Py—CH₃), 5.77(s, 1H, pyrazole), 5.35(s, 2H, CH₂), 14.10(s, 1H, SH), 7.44—7.68(m, 4H, phenyl), 9.94(s, 1H, CH=N)	163.98, 162.12, 148.76, 147.73, 147.27, 140.61, 135.34, 134.62, 130.73, 124.34, 123.27, 105.47, 43.58, 13.69, 11.11
G11	2.02(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.79(s, 1H, pyrazole), 5.37(s, 2H, CH₂), 14.08(s, 1H, SH), 7.50—7.74(m, 4H, phenyl), 9.95(s, 1H, CH=N)	164.35, 163.31, 162.67, 147.69, 147.13, 140.78, 135.28, 130.83, 125.17, 118.01, 114.24, 105.27, 42.98, 13.81, 11.06
G12	2.02(s, 3H, Py—CH₃), 2.21(s, 3H, Py—CH₃), 3.64(s, 3H, Ph—CH₃), 5.76(s, 1H, pyrazole), 5.36(s, 2H, CH₂), 14.13(s, 1H, SH), 7.21—7.63(m, 4H, phenyl), 9.85(s, 1H, CH=N)	164.11, 161.87, 147.18, 146.84, 139.93, 138.51, 133.46, 131.95129.02, 128.98, 126.06, 105.05, 42.67, 20.82, 13.29, 10.63
G13	2.03(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.73(s, 1H, pyrazole), 5.34(s, 2H, CH₂), 7.44—7.72(m, 4H, phenyl), 9.74(s, 1H, CH=N)	162.34, 161.89, 147.74, 147.27, 140.32, 135.36, 134.38, 131.48, 130.62, 128.18, 127.98, 105.54, 43.21, 13.72, 11.07
G14	2.02(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.77(s, 1H, pyrazole), 5.36(s, 2H, CH₂), 14.09(s, 1H, SH), 7.21—7.73(m, 5H, phenyl), 9.66(s, 1H, CH=N)	164.56, 161.95, 147.98, 147.23, 140.15, 134.05, 131.23, 129.42, 128.37, 105.71, 43.42, 13.69, 11.10
G15	2.03(s, 3H, Py—CH₃), 2.22(s, 3H, Py—CH₃), 5.79(s, 1H, pyrazole), 5.32(s, 2H, CH₂), 14.11(s, 1H, SH), 7.46—7.68(m, 3H, phenyl), 10.58(s, 1H, CH=N)	164.18, 162.41, 161.07, 147.88, 147.12, 140.28, 135.41, 134.71, 125.25, 118.13, 113.47, 105.63, 43.47, 13.52, 10.89

Table 3 Biological test results of compounds G1—G15 against four vegetable pathogens

Compd.	EC₅₀ value/(g·L^-1)								EC₉₅ value/(g·L^-1)
Compd.	Gibberlla nicotiancola		Gibberlla saubinetii		F.o.f.sp. niveum^*		Pythium solani		Gibberlla nicotiancola		Gibberlla saubinetii		F.o.f.sp. niveum^*		Pythium solani
G1	0.92		2.67		1.13		0.12		7.28		12.60		21.80		11.83
G2	0.14		0.10		1.40		0.23		5.54		2.90		23.34		10.42
G3	0.40		0.06		6.54		0.83		3.31		2.03		24.32		7.54
G4	0.65		2.43		1.86		0.87		7.22		14.23		25.33		10.28
G5	0.73		2.33		1.71		0.27		12.05		18.23		26.70		11.63
G6	2.06		2.02		0.63		1.03		6.66		14.81		27.22		9.57
G7					3.48		45.78
G8	1.05		2.12		3.09		0.21		6.41		12.70		26.19		8.40
G9	0.10		0.04		0.01		0.07		1.12		0.31		7.18		1.06
G10	0.13		0.12		0.02		0.09		1.82		0.35		16.47		2.36
G11	0.02		0.02		0.03		0.08		1.43		0.38		18.09		4.21
G12
G13		0.97		0.42		2.57		0.12		2.11		0.59		20.11		4.75
G14												212.60
G15		0.05		0.05		0.04		0.67		1.35		0.26		9.38		1.44
Triazolone		0.13		0.02		0.03		0.01		1.89		0.39		20.01		2.35

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