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Chemical and Biological Technologies in Agriculture

Table 2 1H NMR (400 MHz) and 13C NMR (100 MHz) for compounds 1–5 (CDCl3)

From: Larvicidal activity of the black pepper, Piper nigrum (Fam: Piperaceae) extracts on the cattle tick, Rhipicephalus australis (Acari: Ixodidae)

(1) PELLITORINE (m/z = 223,1936—C14H25NO)

(2) HOMOPELLITORINE (m/z = 237,2092—C15H27NO)

(3) PIPYAQUBINE (m/z: 333,3031—C22H39NO)

Position

δ1H / I / m / J (Hz)

δ13C

Position

δ1H / I / m / J (Hz)

δ13C

Position

δ1H / I / m / J (Hz)

δ13C

1 (C = O)

–

166.33

1 (C = O)

–

166.42

1 (C = O)

–

165.9

2

5.74 / 1H / d / 15.2

121.51

2

5.7 / 1H / d / 14.9

121.67

2

6.22 / 1H / d / 14.8

118.7

3

7.17 / 1H / dd / 15; 10

141.26

3

7.15 / 1H / dd / 15.1; 10

141.35

3

7.19 / 1H / dd / 10.5; 4.3

142

4

6.07 / 2H / m

128.06

4

6.1 / 1H / dd / 15.6; 9.5

128.17

4

6.15 / 1H / dd / 15.1; 10.8

129.01

5

143.15

5

6.03 / 1H / dd / 15.3; 6.2

143.26

5

6.03 / 1H / m

143.1

6

2.12 / 2H / q / 6.9

32.78

6

2.1 / 2H / dd / 13.2; 6.6

32.97

6

2.1 / 2H / q / 7.2

33.1

7

1.39 / 2H / m

31.23

7

1.25 / 6H / m

29.08

7—16

1.2—1.31 / 20H / m

29—32

8

1.28 / 4H / m

28.34

8

28.6

17

1.4 / 2H / m

22.8

9

22.33

9

22.5

18

0.9 / 3H / t

14.31

10

0.86 / 3H / t / 6.8

13.86

10

0.85 / 3H / m

14.08

   
      

1'-4'

3.47—3.58 / 4H / m

43–47

NH

5.59 / 1H / brs

–

NH

5.4 / 1H / brs

–

2'-3'

1.55—1.62 / 4H / m

24.8—26.8

1'

3.14 / 2H / t / 6

46.84

1'

3.14 / 2H / t / 6.5

46.9

   

2'

1.78 / 1H / m

28.49

2'

1.38 / 1 H / t / 6.7

31.75

   

3'

0.9 / 6H / d / 6.8

19.99

3'

1.77 / 2H / sept. / 6.7

28.81

   

4'

4'

0.9 / 6H / d / 6.6

20.13

   
   

5'

20.13

   

(4) N-isobutyl-2,4,12(E,E,Z)-octadecatrieamide (m/z = 333,5512—C22H39NO)

5) N-isobutyl-2,4-eicosadienamide (m/z: 363,6202—C24H45NO)

Position

δ1H / I / m / J (Hz)

δ13C

Position

δ1H / I / m / J (Hz)

δ13C

1 (C = O)

–

166.6

1 (C = O)

–

167 (HMBC)

2

5.75 / 1H / d / 15.2

121.9

2

5.72 / 1H / d / 15

121

3

7.18 / 1H / dd / 15.1; 10

141.4

3

7.17 / 1H / dd / 15.1; 9.9

141

4

6.1 / 1H / dd / 14.9; 9.8

128.4

4

6.1 / 1H / dd / 15; 9.6

128

5

6.02 / 1H / dd / 15.5; 6.4

143.3

5

6.03 / 1H / dd / 15.2; 6.4

143

6

2.11 / 2H / q

33.15

6

2.12 / 1H / q

32.18

7

1.38 / 2H / t / 6

29; 29.92; 29.52; 29.35

7

1.54 / 2H / t / 7.2

29

8

1.22–1.31 / 12H / m

8–19

1.23 / 24H / s

29.3–29.9

9

20

0.9 / 3H / d / 6.6

20.37

10

   

11

1.9 / 4H / m

27.11

NH

5.43 / 1H / brs

–

12

5.32 / 2H / t / 5.6

130

1'

3.14 / 1H / t / 6.4

47.19

13

130.1

2'

1.78 / 2 H / sept / 6.8

28.9

14

1.9 / 4H / m

27.36

3'

0.86 / 6H / t / 6.8

14.37

15

1.22–1.31 / 12H / m

28.87

4'

16

32.17

   

17

22.54

   

18

0.86 / 3H / m

14.2

   

NH

5.55 / 1H / brs

–

   

1'

3.13 / 2H / t / 6.4

47.14

   

2'

1.77 / 1 H / sept / 6.8

28.83

   

3'

0.9 / 6H / d / 6.6

20.35

   

4'

   
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