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Table 2 Compounds identified by GC-MS analysis

From: Root exudate profiling of maize seedlings inoculated with Herbaspirillum seropedicaeand humic acids

Retention time (min)

Compound class

Control

HA

H. seropedicae

HA + H. seropedicae

7

14

21

7

14

21

7

14

21

7

14

21

 

Nitrogenous compounds

            

9.575

 3-Butenoic acid, 3-methoxy-4-nitro-, methyl ester, (E)

nd

nd

nd

nd

3.82

nd

nd

nd

nd

nd

nd

nd

14.754

 Benzene, 1-isocyanato-4-methoxy

nd

nd

nd

nd

0.82

nd

nd

0.83

nd

0

nd

nd

20.618

 3,4-Dimethoxy-6-amino toluene

8.54

2.75

0

8.93

4.78

6.08

7.41

5.00

9.70

12.14

5.43

3.35

21.787

 1H-Pyrrole-3-carboxylic acid, 5-formyl-1-(methoxymethyl)-, methyl ester

4.22

nd

nd

nd

1.21

nd

nd

nd

2.65

nd

nd

nd

21.795

 3,4,5-Trimethoxybenzylamine

nd

nd

nd

5.11

nd

nd

3.47

1.18

1.18

4.56

1.21

nd

24.873

 2,5-Dimethoxyphenyl isocyanate

11.41

7.41

0

16.78

13.18

24.30

14.36

10.64

48.74

18.82

24.19

16.91

25.952

 2,4-Dimethoxyphenylamine, N-ethoxycarbonyl-

0.48

nd

nd

0

nd

nd

nd

0.26

0.57

0.68

0.70

nd

26.019

 9H-Purin-6-amine, N,N,9-trimethyl

2.15

nd

nd

1.30

nd

nd

1.97

nd

nd

1.84

nd

nd

26.982

 4-(Diethylamino)salicylaldehyde

nd

nd

nd

nd

nd

nd

nd

nd

2.87

nd

nd

nd

27.134

 2,3,4-Trimethoxyphenylacetonitrile

nd

nd

nd

nd

nd

nd

nd

nd

0.94

nd

nd

nd

28.503

 Bicyclo[2.2.1]heptane-2-acetamide, N-(1,3-dihydro-5,6-dimethoxy-3-oxo-4-isobenzofuranyl)

3.04

nd

nd

4.69

nd

5.30

3.51

nd

13.17

5.26

nd

3.32

28.703

 3,4,5-Trimethoxyphenyl cyanate

nd

nd

nd

nd

2.23

nd

nd

nd

nd

nd

nd

nd

28.709

 Tris(2,4,6-dimethylamino)pyrimidine

nd

nd

nd

nd

nd

nd

nd

1.75

nd

nd

3.34

nd

28.915

 Caffeine

nd

nd

nd

0.48

nd

nd

nd

nd

nd

nd

nd

nd

29.340

 Acetamide, N-[2-(3,4-dimethoxyphenyl)ethyl]

nd

nd

nd

nd

nd

nd

nd

0.89

4.06

nd

nd

nd

29.346

 3-Pyridinecarboxamide, 4-(methoxymethyl)-6-methyl-2-propoxy-

nd

nd

nd

nd

nd

0.53

nd

nd

nd

nd

nd

1.49

29.537

 1,3-Benzenediamine, N,N′-diethyl

nd

nd

nd

nd

0.41

nd

nd

nd

nd

nd

nd

nd

30.534

 Carbonic acid, monoamide, N-(2,4-dimethoxyphenyl)-, butyl ester

nd

nd

9.55

nd

nd

nd

nd

nd

nd

nd

nd

nd

30.774

 3-(2-Ethoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid, ethyl ester

nd

nd

nd

nd

12.62

nd

nd

nd

nd

nd

nd

nd

30.775

 Carbonic acid, monoamide, N-(2,4-dimethoxyphenyl)-, butyl ester

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

6.93

nd

30.801

 Propanamide, 3-amino-N-(2,5-dimethoxyphenyl)-3-(hydroxyimino)-

nd

nd

nd

nd

nd

nd

nd

14.99

nd

nd

nd

nd

26.134

 Phenol, 4-(aminomethyl)-2-methoxy

nd

nd

nd

nd

0.33

nd

nd

nd

nd

nd

nd

nd

30.741

 1,5-Bis[veratrylaminomethyl]-2,6-dihydroxynaphthalene

nd

1.25

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

30.952

 3H-Purin-6-amine, N,N,3-trimethyl

nd

nd

nd

nd

nd

nd

0.61

nd

nd

0.58

nd

nd

31.834

 Benzeneethanamine, N-acetyl-2,3,4,5-tetramethoxy

nd

nd

nd

nd

nd

nd

nd

2.83

nd

nd

nd

nd

32.132

 Acetamide, N-(3,4,5-trimethoxyphenethyl)

nd

nd

nd

nd

nd

nd

nd

nd

0.91

nd

nd

0.40

35.077

 Uridine, 2′-deoxy-3-methyl-3′,5′-di-O-methyl-

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.19

nd

nd

35.926

 Cytidine, N-methyl-, 2′,3′,5′-trimethyl ether

0.62

nd

nd

1.44

nd

nd

1.52

nd

nd

0.55

nd

nd

36.019

 Thymidine, 2′-deoxy-N,O,O-trimethyl-

0.91

nd

nd

1.62

nd

nd

2.24

nd

nd

3.37

nd

nd

37.792

N-[12-Aminododecyl]aziridine

0.52

nd

nd

0.58

nd

nd

0

nd

nd

0.95

nd

nd

41.125

 Adenosine, 2′-deoxy-N,N,O,O-tetramethyl-

nd

nd

nd

0.65

nd

nd

1.60

nd

nd

2.11

nd

nd

42.007

 Adenosine, 3′-amino-3′-deoxy-N,N-dimethyl

nd

nd

nd

0.20

nd

nd

0.46

nd

nd

0.66

nd

nd

  

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

 

Carbohydrate compounds

            

17.168

 1,6-Anhydro-β-d-glucose, trimethyl ether

nd

nd

nd

1.35

nd

nd

nd

0.77

nd

0.83

nd

nd

18

 α-d-Galactopyranoside, methyl 2,3,4,6-tetra-O-methyl

1.74

nd

nd

3.17

nd

nd

0.73

nd

nd

4.24

nd

nd

17.688

 3,4,6-Tri-O-methyl-d-glucose

nd

nd

nd

nd

0.54

nd

nd

0.83

nd

nd

nd

nd

18.1280

 α-Methyl 4-methylmannoside

nd

nd

nd

nd

nd

nd

nd

0.55

nd

nd

nd

nd

21.355

 2,4,5,6,7-Pentamethoxyheptanoic acid, methyl ester

nd

nd

nd

nd

0.33

nd

nd

nd

nd

nd

nd

nd

20.206

 β-d-Glucopyranose, 1,6-anhydro

nd

nd

nd

nd

nd

nd

nd

nd

1.02

nd

nd

nd

28.814

 1,2,3,4-Tetramethylmannose

nd

nd

nd

nd

1.85

nd

nd

1.75

nd

nd

0.58

nd

28.631

 α-d-Mannopyranoside, methyl 2,3,4,6-tetra-O-methyl

nd

nd

3.33

nd

nd

nd

0

nd

nd

nd

nd

0.53

37.425

 α-d-Glucopyranoside, phenyl 2,3,4,6-tetra-O-methyl

nd

nd

nd

nd

41.61

31.93

nd

22.57

nd

nd

5.62

nd

 

Fatty acids as methyl ester

            

26.320

 Tridecanoic acid, 12-methyl-, methyl ester

0.77

nd

nd

0

nd

nd

1.06

1.26

nd

0.80

1.62

nd

26.323

 Methyl tetradecanoate

nd

nd

nd

1.22

nd

nd

nd

nd

nd

0

nd

nd

27.419

 2-Hexadecenoic acid, methyl ester, (E)

nd

nd

nd

0.32

nd

nd

nd

nd

nd

0.37

nd

nd

27.901

 Tridecanoic acid, 12-methyl-, methyl ester

nd

nd

nd

0.28

nd

nd

nd

nd

nd

0

nd

nd

30.133

 Methyl hexadec-9-enoate

1.06

nd

nd

2.94

nd

nd

0.84

nd

nd

0.47

nd

nd

30.181

 9-Octadecenoic acid (Z)-, methyl ester

0

nd

nd

0

nd

nd

nd

nd

nd

0.13

nd

nd

30.625

 Hexadecanoic acid, methyl ester

4.22

2.26

0

7.28

nd

nd

4.05

nd

1.04

3.22

3.31

1.96

30.327

 6-Octadecenoic acid, methyl ester

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.82

nd

34.053

 9-Octadecenoic acid, methyl ester, (E)

1.27

nd

nd

nd

nd

nd

nd

0.73

nd

nd

0.84

nd

34.164

 8-Octadecenoic acid, methyl ester, (E)

0.67

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

34.548

 Octadecanoic acid, methyl ester

0.95

1.11

0

1.36

0.57

nd

2.15

1.61

0.28

1.40

1.60

0.67

38.161

 Eicosanoic acid, methyl ester

nd

nd

nd

0.16

nd

nd

nd

nd

nd

nd

nd

nd

 

Organic acids

            

26.507

 Benzoic acid, 4,5-dimethoxy-2-(4-methoxybenzenesulfonylamino)-

nd

nd

nd

nd

1.31

nd

nd

nd

nd

nd

nd

nd

40.052

 Succinic acid, di(5-methoxy-3-methylpent-2-yl) ester

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.36

nd

nd

43.743

 Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester

nd

nd

nd

nd

nd

nd

nd

0.70

nd

nd

nd

nd

 

Aromatics and phenol derivatives

            

15.817

 2-Methoxy-4-vinylphenol

nd

nd

nd

nd

nd

nd

nd

nd

0.3

0

nd

nd

19.337

 Phenol, 4,6-di(1,1-dimethylethyl)-2-methyl

nd

nd

nd

0.24

nd

nd

nd

nd

nd

0.23

nd

nd

24.653

 Isoelemicin

nd

nd

nd

nd

nd

nd

nd

nd

0.49

0

nd

nd

37.592

 Benzene, (1-methyldodecyl)

0.31

nd

nd

nd

nd

nd

1.98

nd

nd

0.80

nd

nd

41.779

 1,2-Benzenedicarboxylic acid, diisooctyl ester

nd

nd

69.71

nd

nd

nd

1.49

nd

nd

0.44

nd

nd

41.784

 1,2-Benzenedicarboxylic acid, mono(2-ethylhexyl) ester

1.55

nd

nd

nd

nd

2.37

nd

nd

nd

0

nd

7.49

21.512

 Phenol, 2,6-dimethoxy-4-(2-propenyl)

nd

nd

nd

nd

0.25

nd

nd

nd

nd

nd

nd

nd

35.007

 Phenol, 5-methoxy-2,3,4-trimethyl

nd

0

nd

nd

0.22

nd

nd

nd

nd

nd

nd

nd

37.803

 Benzene, (1-methylnonadecyl)

nd

0.78

nd

nd

nd

nd

nd

1.15

nd

nd

1.36

nd

22.015

 Benzoic acid, 4-hydroxy-3,5-dimethoxy

nd

nd

nd

nd

0.21

nd

nd

nd

nd

nd

nd

nd

22.016

 1,2,3,4-Tetramethoxybenzene

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.27

nd

23.399

 Benzoic acid, 3,4-dimethoxy-, methyl ester

nd

nd

nd

nd

0.72

1.41

nd

nd

nd

nd

nd

1.65

25.152

 2-Propenoic acid, 3-(4-methoxyphenyl)-, methyl ester

nd

nd

nd

1.17

1.03

nd

nd

0.65

nd

nd

0.66

nd

26.277

 Benzenepropanoic acid, 3,4-dimethoxy-, methyl ester

nd

nd

nd

nd

nd

5.14

nd

nd

nd

nd

nd

3.27

26.328

 Benzoic acid, 3,4,5-trimethoxy-, methyl ester

nd

nd

nd

0

nd

nd

nd

nd

2.70

nd

nd

nd

29.738

 2-Propenoic acid, 3-(3,4-dimethoxyphenyl)-, methyl ester

0.49

nd

nd

0

2.61

5.02

nd

0.75

4.24

0.23

1.24

3.21

36.154

 2-Propenoic acid, 2-methyl-, dodecyl ester

0

nd

nd

0

nd

nd

nd

nd

nd

0.12

nd

nd

 

Terpenoids and steroids

            

43.074

 17β-Hydroxy-6α-pentyl-4-oxa-5β-androstan-3-one

nd

nd

nd

0.74

nd

nd

0.93

nd

nd

nd

nd

nd

43.412

 Dihydroxyisosteviol

3.88

nd

nd

3.94

nd

nd

5.45

3.95

nd

3.69

0.73

nd

42.582

 Dihydro-isosteviol methyl ester

nd

2.04

nd

nd

0

9.42

nd

nd

nd

nd

nd

17.03

43.332

 Methyl dihydroisosteviol

nd

nd

nd

nd

1.47

nd

nd

nd

nd

nd

nd

nd

43.665

 Isosteviol methyl ester

nd

2.88

nd

nd

4.81

nd

nd

4.90

17.18

nd

4.68

nd

39.849

 5-Cholene, 3,24-dihydroxy-

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.12

nd

nd

43.430

 Patchoulene

nd

nd

nd

0.36

nd

nd

nd

nd

nd

nd

nd

nd

45.538

 Androstan-17-one, 3-ethyl-3-hydroxy-, (5α)

nd

0.78

nd

nd

2.89

nd

nd

1.03

0.50

nd

2.30

nd

42.354

 5α,6α-Epoxy-17-oxo-6β-pentyl-4-nor-3,5-secoandrostan-3-oicacid, methyl ester

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.31

43.091

 5β-Pregnan-17α,21-diol-3,20-dione

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

25.88

43.434

 Pregnan-20-one, (5α,17α)

nd

nd

2.48

nd

nd

nd

nd

nd

nd

nd

nd

nd

 

Alcohols

            

3.974

 Ethanol, 2-(2-methoxyethoxy)

nd

nd

nd

nd

nd

nd

nd

nd

1.18

0.33

nd

nd

6.715

 1-Hexanol, 2-ethyl

1.65

 

7.48

2.71

0.39

1.13

0.86

nd

nd

3.39

nd

1.19

12.925

 Ethanol, 2-phenoxy

nd

nd

nd

nd

nd

nd

nd

nd

0.63

nd

nd

nd

42.010

 9-t-Butyltricyclo[4.2.1.1(2,5)]decane-9,10-diol

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

1.03

nd

 

Unidentified

            

30.542

 

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

3.14

31.625

 

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.74

31.825

 

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

32.184

 

nd

nd

nd

nd

0.79

nd

nd

nd

nd

nd

nd

nd

35.248

 

nd

nd

nd

nd

0.77

nd

nd

nd

nd

nd

nd

nd

38.362

 

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.42

nd

nd

39.253

 

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.09

nd

nd

40.033

 

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.43

nd

40.230

 

nd

nd

nd

0.20

nd

nd

nd

nd

nd

0.37

nd

nd

40.833

 

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.18

40.964

 

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.31

nd

nd

41.908

 

nd

nd

nd

0.49

nd

nd

nd

nd

nd

0.41

nd

nd

42.157

 

nd

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.24

nd

43.746

 

nd

nd

nd

nd

nd

nd

nd

0.43

nd

0

nd

nd

44.305

 

nd

nd

nd

nd

nd

nd

nd

nd

nd

0.27

nd

nd

44.532

 

nd

nd

nd

0

nd

nd

nd

nd

nd

nd

nd

0.45

45.275

 

nd

nd

nd

0.74

nd

nd

0.35

nd

nd

0.89

nd

nd

46.026

 

nd

nd

nd

nd

nd

nd

0

nd

nd

0.11

nd

nd

46.277

 

nd

nd

nd

nd

nd

nd

0

nd

nd

nd

nd

1.72

46.606

 

nd

nd

nd

nd

nd

0.53

0

nd

nd

0

nd

nd

  1. Compound exudates from maize seedlings at different growth stages (7, 14, and 21 days) induced or not (control) by humic acids (HA), Herbaspirillum seropedicae (H. seropedicae), and HA and H. seropedicae. nd, not detected.