1
TABLE 3. H NMR Spectral Data (CDCl3/TMS) of Compounds 3a-f, 4a-d,
7a-d and 8
Com-
pound
Chemical shifts, δ, ppm (J, Hz)
8.13 (1H, d, J = 1.6, Ar); 7.42 (1H, dd, J = 8.7, 1.6, Ar); 7.34 (1H, d, J = 8.7, Ar);
7.16 (2H, d, J = 8.5, Ar); 6.90 (2H, d, J = 8.5, Ar); 4.19 (2H, s, CH2); 3.80 (3H, s,
OCH3); 3.17(2H, q, J = 7.5, CH2); 1.34 (3H, t, J = 7.5, CH3)
3a
3b
3c
8.13 (1H, s, Ar); 7.40 (1H, d, J = 8.6, Ar); 7.33 (1H, d, J = 8.6, Ar); 7.15 (2H, d, J = 8.3,
Ar); 6.89 (2H, d, J = 8.3, Ar); 4.19 (2H, s, CH2); 3.80 (3H, s, OCH3); 3.11 (2H, t, J = 7.5,
CH2); 1.82-1.76 (2H, m, CH2); 0.99 (3H, t, J = 7.3, CH3)
8.12 (1H, d, J = 1.8, Ar); 7.39 (1H, dd, J = 8.6, 1.8, Ar); 7.32 (1H, d, J = 8.6, Ar);
7.15 (2H, d, J = 8.6, Ar); 6.88 (2H, d, J = 8.6, Ar); 4.18 (2H, s, CH2); 3.79 (3H, s, OCH3);
3.13 (2H, t, J = 7.6, CH2); 1.77-1.69 (2H, m, CH2); 1.44-1.35 (2H, m, CH2); 0.93 (3H, t,
J = 7.4, CH3)
7.97 (1H, d, J =2.1, Ar); 7.39 (1H, d, J =8.7, Ar); 7.25-7.28 (1H, m, Ar);
7.14-7.17 (2H, m, Ar); 6.87-6.91 (2H, m, Ar); 4.19 (2H, s, CH2); 3.80 (3H, s, OCH3);
3.18 (2H, q, J = 7.5, CH2); 1.34 (3H, t, J = 7.5, CH3)
3d
3e
3f
8.83 (1H, s, Ar); 8.13 (1H, d, J = 8.8, Ar);7.45 (1H, d, J = 8.8, Ar);7.09 (2H, d, J = 7.8,
Ar); 6.81 (2H, d, J = 7.8, Ar); 4.16 (2H, s, CH2); 3.71 (3H, s, OCH3); 3.14 (2H, q, J = 7.2,
CH2); 1.29 (3H, t, J = 7.5, CH3)
8.92 (1H, d, J = 2.2, Ar); 8.24 (1H, m, Ar); 7.55 (1H, m, Ar); 7.18 (2H, d, J = 8.6, Ar);
6.90 (2H, m, Ar); 4.26 (2H, s, CH2); 3.80 (3H, s, OCH3); 3.71 (2H, t, J = 7.6, CH2);
1.83 (2H, q, J = 7.5, CH2); 1.02 (3H, t, J = 7.4, CH3)
8.12 (1H, d, J = 1.6, Ar); 7.42 (1H, dd,J = 8.7, 1.6, Ar);7.37 (1H, d, J = 8.7, Ar);
7.10 (2H, d, J = 8.2, Ar); 6.80 (2H, d, J = 8.2, Ar); 5.05 (1H, br. s, OH); 4.18 (2H, s, CH2);
3.18 (2H, q, J = 7.5,CH2),1.34 (3H, t, J = 7.5, CH3)
4a
4b
4c
4d
7a
8.12 (1H, d, J = 1.6, Ar); 7.42 (1H, dd,J = 8.6,1.6, Ar); 7.33 (1H, d, J = 8.6, Ar);
7.08 (2H, d, J = 8.4, Ar); 6.78 (2H, d, J = 8.4, Ar); 5.35 (1H, s, OH);4.18 (2H, s, CH2);
3.12 (2H, t, J = 7.5, CH2); 1.84-1.75 (2H, m, CH2); 0.99 (3H, t, J = 7.5, CH3)
8.11 (1H, s, Ar); 7.41 (1H, d, J = 8.5, Ar); 7.33 (1H, d, J = 8.5, Ar); 7.07 (2H, d, J = 7.7, Ar);
6.78 (2H, d, J = 7.7, Ar); 5.43 (1H, s, OH); 4.18 (2H, s, CH2); 3.14 (2H, t, J = 7.5, CH2);
1.76-1.70 (2H, m, CH2); 1.42-1.37 (2H, m, CH2); 0.93 (3H, t, J = 7.3, CH3)
7.97 (1H, d, J = 2.1, Ar); 7.40 (1H, d, J = 8.7, Ar); 7.25-7.28 (1H, m, Ar);
7.17-7.14 (2H, m, Ar); 6.91-6.87 (2H, m, Ar); 5.25 (1H, br. s, OH); 4.18 (2H, s, CH2);
3.18 (2H, q, J = 7.5, CH2); 1.34 (3H, t, J = 7.5, CH3)
7.87 (1H, s, Ar); 7.28 (2H, dd, J = 8.5, 8.2, Ar); 6.98 (2H, d, J = 7.7, Ar); 6.77 (2H, d,
J = 7.7, Ar); 4.95 (1H, t, J = 6.9, CH); 3.75 (3H, s, OCH3); 3.19-3.14 (1H, m, CH2);
3.06-3.01 (1H, m, CH2); 2.58-2.49 (1H, m, CH2); 2.47-2.38 (1H, m, CH2); 2.12 (1H,
br. s, OH); 1.03 (3H, t, J = 7.4, CH3)
7.87 (1H, s, Ar); 7.31 (1H, d, J = 8.6, Ar); 7.25 (1H, d, J = 8.1, Ar); 7.01 (2H, d, J = 7.7,
Ar);6.79 (2H, d, J = 7.7, Ar); 4.95 (1H, t, J = 6.8, CH); 3.76 (3H, s, OCH3);
3.21-3.15 (1H, m, CH2); 3.06-3.01 (1H, m, CH2); 2.54-2.39 (2H, m, CH2);
2.08 (1H, br.s, OH); 1.60-1.51 (1H, m, CH2); 1.48-1.39 (1H, m, CH2); 0.85 (3H, t, J = 7.2, CH3)
7b
7c
7d
8
7.86 (1H, s, Ar); 7.31 (1H, d, J = 8.6, Ar); 7.24 (1H, d, J = 8.1, Ar); 7.02 (2H, d, J = 7.7, Ar);
6.77 (2H, d, J = 7.7, Ar); 4.99 (1H, t, J = 6.8, CH); 3.78 (3H, s, OCH3); 3.27-3.25 (1H, m, CH2);
3.14-3.10 (1H, m, CH2); 2.55-2.43 (2H, m, CH2); 1.98 (1H, br.s, OH);
1.50-1.47 (2H, m, CH2); 1.35-1.21 (1H, m, CH2); 0.87 (3H, t, J = 7.2, CH3)
7.95 (1H, d, J =2.1, Ar); 7.35 (1H, d, J = 8.7, Ar); 7.27-7.25 (1H, m, Ar); 7.16-7.14 (2H,
m, Ar); 6.90-6.86 (2H, m, Ar); 4.94 (1H, t, J = 6.9, CH); 3.78 (3H, s, OCH3);
3.18-3.13 (1H, m, CH2); 3.07-3.02 (1H, m, CH2); 2.56-2.45 (1H, m, CH2);
2.46-2.39 (1H, m, CH2); 2.10 (1H, br. s, OH); 1.08 (3H, t, J = 7.4, CH3)
7.79-7.75 (1H, m, Ar); 7.19 (2H, dd, J = 8.5, 8.2, Ar); 6.85 (2H, d, J = 7.6, Ar);
6.60 (2H, d, J = 7.7, Ar); 5.88 (1H, s, OH); 4.94-4.83 (1H, m, CH); 3.08 (1H, s, CH2);
2.97-2.95 (1H, m, CH2); 2.41-2.34 (2H, m, CH2); 2.09 (1H, br. s, OH);
1.12 (2H, d, J = 6.9, CH2); 0.82-0.75 (3H, m, CH3)
Compounds 3a-d and 4a-d were tested in the primary laboratory screening for fungicidal, herbicidal,
and insecticidal properties. The tests showed that the hydroxy ethanones 4a-d exhibited fungicidal activity,
whereas ketones 3a-c showed insecticidal activity.
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