1-Amino-3,4-dialkylnaphthalene-2-carbonitriles as fungicides
6.8Hz), 7.78 ꢀd, 1H, J=8.5Hz), 7.97 ꢀd, 1H,
J=8.5Hz); 13C NMR d ꢀppm): 13.7, 14.7, 26.1,
91.9, 118.4, 120.9 ꢀ2C), 121.5, 124.9, 125.0, 128.8,
135.3, 138.0, 147.3.
2.2.13 3-Phenyl-2-propylhex-1-en-1, 1-dicarbonitrile
(12k: R1=R2=n-C3H7)
From 5-phenyloctan-4-one;16 bp 144±149°C at 2
hPa. IR ꢀKBr) n ꢀcmÀ1): 3092, 3066, 3029, 2961,
2937, 2872, 2228, 1580, 1492, 1464, 1454, 1084,
752, 701. 1H NMR d ꢀppm): 0.85 ꢀt, 3H, J=7.1),
0.86±0.97 ꢀm, 1H), 1.00 ꢀt, 3H, J=7.3Hz), 1.27±1.40
ꢀm, 2H), 1.37±1.47 ꢀm, 1H), 1.84±1.92 ꢀm, 1H),
2.00±2.08 ꢀm, 1H), 2.24±2.30 ꢀm, 1H), 2.33±2.39
ꢀm, 1H), 4.33 ꢀt, 1H, J=7.6Hz), 7.24±7.39 ꢀm, 5H).
13C NMR d ꢀppm): 13.9, 14.6, 20.7, 23.5, 33.2, 34.7,
51.7, 85.8, 112.0, 112.3, 127.9 ꢀ2C), 128.2, 129.1
ꢀ2C), 137.5, 187.7.
2.2.9 2-Ethyl-3-phenylpent-1-en-1, 1-dicarbonitrile
(12i: R1=R2=C2H5)
From 4-phenylhexan-3-one;15 bp 134±138°C at 3.5
hPa. IR ꢀKBr) n ꢀcmÀ1): 3092, 3067, 3029, 2973,
2940, 2879, 2232, 1580, 1492, 1464, 1448, 1379,
1090, 764, 707. 1H NMR d ꢀppm): 0.86 ꢀt, 3H,
J=7.6Hz), 1.02 ꢀt, 3H, J=7.6Hz), 1.90±2.01 ꢀm,
1H), 2.06±2.17 ꢀm, 1H), 2.29±2.38 ꢀm, 1H), 2.38±
2.47 ꢀm, 1H), 4.24 ꢀt, 1H, J=7.6Hz), 7.24±7.40 ꢀm,
5H). 13C NMR d ꢀppm): 12.0, 13.9, 24.2, 25.6, 53.6,
85.9, 111.8, 112.3, 127.9 ꢀ2C), 128.1, 129.1 ꢀ2C),
137.3, 189.0.
2.2.14 1-Amino-3,4-dipropylnaphthalene-2-
carbonitrile (3b)
Colourless crystals ꢀfrom ethanol). IR ꢀKBr) n ꢀcmÀ1):
3481, 3356, 3237, 3084, 2961, 2925, 2872, 2217,
1630, 1574, 1504, 1485, 1450, 1435, 1391, 1166,
1084, 758, 670. 1H NMR d ꢀppm): 1.08 ꢀt, 3H,
J=7.3Hz), 1.24 ꢀt, 3H, J=7.3Hz), 1.57±1.66 ꢀm,
2H), 1.65±1.74 ꢀm, 2H), 2.84±2.93 ꢀm, 4H), 4.97
ꢀbrs, 2H, NH2), 7.47 ꢀdd, 1H, J=8.4, 6.8Hz), 7.56
ꢀdd, 1H, J=8.6, 6.8Hz), 7.79 ꢀd, 1H, J=8.4Hz), 7.96
ꢀd, 1H, J=8.6Hz); 13C NMR d ꢀppm): 14.4, 14.5,
24.3, 24.4, 30.1, 36.9, 92.3, 118.5, 121.1, 121.6,
124.9, 125.1, 127.6, 128.8, 134.6, 136.6, 147.2.
2.2.10 1-Amino-3,4-diethylnaphthalene-2-carbonitrile
(2b)
Colourless crystals ꢀfrom ethanol). IR ꢀKBr) n ꢀcmÀ1):
3475, 3381, 3249, 3080, 2967, 2925, 2867, 2198,
1636, 1611, 1567, 1508, 1436, 1228, 1170, 758, 670.
1H NMR d ꢀppm): 1.24 ꢀt, 3H, J=7.5Hz), 1.31 ꢀt,
3H, J=7.6Hz), 2.94 ꢀq, 2H, J=7.6Hz), 2.99 ꢀq, 2H,
J=7.5Hz), 4.95 ꢀbrs, 2H, NH2), 7.49 ꢀdd, 1H, J=8.4,
6.8Hz), 7.61 ꢀdd, 1H, J=8.6, 6.8Hz), 7.80 ꢀd, 1H,
J=8.4Hz), 8.00 ꢀd, 1H, J=8.5Hz); 13C NMR d
ꢀppm): 15.3, 15.4, 20.9, 25.6, 91.8, 118.4, 121.1,
121.6, 124.9 ꢀ2C), 127.3, 128.9, 134.4, 137.7, 147.3.
2.2.15 3-Phenylpent-1-en-1, 1-dicarbonitrile (12n:
R1=C2H5, R2=H)
From 2-phenylbutanal;17 bp 110±112°C/2 hPa. IR
ꢀKBr) n ꢀcmÀ1): 3042, 2968, 2935, 2884, 2236, 1598,
1493, 1454, 1080, 742, 700. 1H NMR d ꢀppm): 0.97
ꢀt, 3H, J=7.4Hz), 1.84±1.99 ꢀm, 2H), 3.84 ꢀdt, 1H,
J=11.0, 7.5Hz), 7.33 ꢀd, 1H, J=11.0Hz), 7.22±7.48
ꢀm, 5H). 13C NMR d ꢀppm): 11.7, 27.9, 50.9, 88.6,
110.7, 111.9, 127.5 ꢀ2C), 128.2, 129.5 ꢀ2C), 138.2,
170.8.
2.2.11 3-Phenyl-2-propylpent-1-en-1, 1-dicarbonitrile
(12j: R1 =C2H5, R2=n-C3H7)
From 3-phenylheptan-4-one;14 bp 128±134°C at 1.5
hPa. IR ꢀKBr) n ꢀcmÀ1): 3090, 3067, 3029, 2961,
2937, 2872, 2228, 1580, 1492, 1468, 1454, 1084,
764, 743, 700. 1H NMR d ꢀppm): 0.84 ꢀt, 3H,
J=7.2Hz), 0.87±0.98 ꢀm, 1H), 1.01 ꢀt, 3H,
J=7.4Hz), 1.31±1.42 ꢀm, 1H), 1.90±2.00 ꢀm, 1H),
2.06±2.16 ꢀm, 1H), 2.22±2.28 ꢀm, 1H), 2.32±2.38
ꢀm, 1H), 4.21 ꢀt, 1H, J=7.6Hz), 7.24±7.39 ꢀm, 5H).
13C NMR d ꢀppm): 12.0, 14.5, 23.4, 24.3, 34.6, 53.6,
86.0, 112.0, 112.4, 127.9 ꢀ2C), 128.2, 129.1 ꢀ2C),
137.4, 187.5.
2.2.16 1-Amino-4-ethylnaphthalene-2-carbonitrile (4c)
Colourless crystals ꢀfrom ethanol). IR ꢀKBr) n ꢀcmÀ1):
3488, 3431, 3387, 3243, 3061, 2961, 2925, 2866,
2195, 1636, 1608, 1495, 1436, 1150, 758. 1H NMR d
ꢀppm): 1.31 ꢀt, 3H, J=7.5Hz), 2.94 ꢀq, 2H,
J=7.5Hz), 4.96 ꢀbrs, 2H, NH2), 7.15 ꢀs, 1H), 7.53
ꢀdd, 1H, J=8.3, 6.8Hz), 7.63 ꢀdd, 1H, J=8.6,
6.8Hz), 7.83 ꢀd, 1H, J=8.3Hz), 7.98 ꢀd, 1H,
J=8.6Hz); 13C NMR d ꢀppm): 14.5, 25.0, 89.4,
118.9, 121.8, 122.4, 124.1, 124.7, 125.8, 128.7,
130.5, 134.3, 146.8.
2.2.12 1-Amino-4-ethyl-3-propylnaphthalene-2-
carbonitrile (3a)
Colourless crystals ꢀfrom ethanol). IR ꢀKBr) n ꢀcmÀ1):
3481, 3356, 3237, 3080, 2961, 2925, 2867, 2217,
1
1630, 1574, 1508, 1483, 1435, 1391, 763, 680. H
NMR d ꢀppm): 1.09 ꢀt, 3H, J=7.3Hz), 1.24 ꢀt, 3H,
J=7.5Hz), 1.65±1.74 ꢀm, 2H), 2.85±2.90 ꢀm, 2H),
2.98 ꢀq, 2H, J=7.5Hz), 4.45 ꢀbrs, 2H, NH2), 7.47
ꢀdd, 1H, J=8.6, 6.8Hz), 7.61 ꢀdd, 1H, J=8.6,
6.8Hz), 7.80 ꢀd, 1H, J=8.4Hz), 7.99 ꢀd, 1H,
J=8.6Hz); 13C NMR d ꢀppm): 14.4, 15.4, 21.0,
24.4, 34.4, 92.3, 118.5, 121.2, 121.6, 124.9 ꢀ2C),
127.3, 128.9, 134.3, 136.2, 147.2.
2.2.17 3-Phenylhex-1-en-1, 1-dicarbonitrile (12o:
R1=n-C3H7, R2=H)
From 2-phenylpentanal;18 bp 126±132°C/3 hPa. IR
ꢀKBr) n ꢀcmÀ1): 3029, 2967, 2935, 2872, 2239, 1598,
1496, 1454, 756, 700. 1H NMR d ꢀppm): 0.95 ꢀt, 3H,
J=7.4Hz), 1.26±1.37 ꢀm, 2H), 1.80±1.93 ꢀm, 2H),
3.95 ꢀdt, 1H, J=11.0, 7.5Hz), 7.33 ꢀd, 1H,
J=11.0Hz), 7.21±7.42 ꢀm, 5H). 13C NMR d ꢀppm):
Pest Manag Sci 57:625±632 ꢀ2001)
629