Phytotoxic and Nematicidal Components of Lavandula luisieri Luis F. Julio,† Alejandro F. Barrero*,‡ M. Mar Herrador del Pino,‡ Jesús F. Arteaga,§ Jesús Burillo,⊥ Maria Fe Andres,† Carmen E. Díazǁ and Azucena González-Coloma*,† †

‡

§

Instituto de Ciencias Agrarias. Consejo Superior de Investigaciones Científicas. Serrano 115-bis, 28006 Madrid, Spain

Departamento de Química Orgánica, Instituto de Biotecnología, Universidad de Granada, Campus de Fuente Nueva, s/n, 18071 Granada, Spain

CIQSO – Center for Research in Sustainable Chemistry and Department of Chemical Engineering, Physical Chemistry, and Organic Chemistry, Facultad de Ciencias Experimentales, Universidad de Huelva, Campus el Carmen, 21071 Huelva, Spain ⊥

Departamento de Ciencia, Tecnología y Universidad, Centro de Investigación y Tecnología Agroalimentaria de Aragón, Gobierno de Aragón, Avda Montañana, 930, Zaragoza, Spain ǁ

Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas. Avda. Astrofísico F. Sánchez, 3, 38206 La Laguna, Tenerife, Spain

Supporting information List of contents

Figure S1. 1H-NMR spectrum of compound 1 (CDCl3, 500 MHz) Figure S2. 13C-NMR spectrum of compound 1 (CDCl3, 125 MHz) Figure S3. HREIMS of compound 1 Figure S4. 1H-NMR spectrum of compound 2 (CDCl3, 500 MHz) Figure S5. 13C-NMR spectrum of compound 2 (CDCl3, 125 MHz) Figure S6. HREIMS spectrum compound 2 Figure S7. 1H-NMR spectrum of compound 3 (CDCl3, 500 MHz) Figure S8. 13C-NMR spectrum of compound 3 (CDCl3, 125 MHz) Figure S9. HRESI-TOFMS of compound 3 Figure S10. 1H-NMR spectrum of compound 5 (CDCl3, 500 MHz) Figure S11. 13C-NMR spectrum of compound 5 (CDCl3, 125 MHz) Figure S12. HREIMS of compound 5 Figure S13. 1H-NMR spectrum of compound 6a (CDCl3, 500 MHz) Figure S14. 13C-NMR spectrum of compound 6a (CDCl3, 125 MHz) Figure S15. HREIMS of compound 6a Figure S16. 1H-NMR spectrum of compound 7 (CDCl3, 500 MHz) Figure S17. 13C-NMR spectrum of compound 7 (CDCl3, 125 MHz) Figure S18. HREIMS of compound 7 Figure S19. 1H-NMR spectrum of compound 8 (CDCl3, 500 MHz) Figure S20. 13C-NMR spectrum of compound 8 (CDCl3, 125 MHz) Figure S21. HREIMS of compound 8 Table S1. Phytotoxic Effects of L. luisieri extracts Table S2. Antifeedant and Nematicidal Effects of L. luisieri extracts

Figure S1. 1H-NMR spectrum of compound 1 (CDCl3, 500 MHz).

Figure S2. 13C-NMR spectrum of compound 1 (CDCl3, 125 MHz).

Figure S3. HREIMS of compound 1.

O

AcO 2

Figure S4. 1H-NMR spectrum of compound 2 (CDCl3, 500 MHz).

O

AcO 2

Figure S5. 13C-NMR spectrum of compound 2 (CDCl3, 125 MHz).

Figure S6. HREIMS of compound 2.

Figure S7. 1H-NMR spectrum of compound 3 (CDCl3, 500 MHz).

Figure S8. 13C-NMR spectrum of compound 3 (CDCl3, 125 MHz).

Figure S9. HRESI-TOFMS of compound 3.

Figure S10. 1H-NMR spectrum of compound 5 (CDCl3, 500 MHz).

Figure S11. 13C-NMR spectrum of compound 5 (CDCl3, 125 MHz).

Figure S12. HREIMS of compound 5.

Figure S13. 1H-NMR spectrum of compound 6a (CDCl3, 500 MHz).

Figure S14. 13C-NMR spectrum of compound 6a (CDCl3, 125 MHz).

Figure S15. HREIMS of compound 6a.

Figure S16. 1H-NMR spectrum of compound 7 (CDCl3, 500 MHz).

Figure S17. 13C-NMR spectrum of compound 7 (CDCl3, 125 MHz).

Figure S18. HREIMS of compound 7.

Figure S19. 1H-NMR spectrum of compound 8 (CDCl3, 500 MHz).

Figure S20. 13C-NMR spectrum of compound 8 (CDCl3, 125 MHz).

Figure S21. HREIMS of compound 8.

Table S1. Phytotoxic Effects of Lavandula. luisieri extracts Lactuca sativa extract essential oil hexane EtOAc EtOH aqueous organic fraction a

mg/mL

germination

Lolium perenne growth

germination

growth

0.40 0.40 0.40 0.40 100%a

24 h 46.4 ± 13.1b 0b 7.5±2.5b 3.4 ± 3.5b 0.0 ± 0.0b

144 h 100 ± 0.0 20.0 ± 4.1b 85.0 ± 2.9 22.5 ± 7.5b 0.0 ± 0.0b

root 29.4 ± 2.3b na 50.8 ± 9.5b na na

72 h 50.0 ± 18.1b 64.0 ± 20.6 b 100.0 ± 12.6 50.0 ± 11.7 b 0.0 ± 0.0 b

168 h 100 ± 0 84.6 ± 5.4 97.4 ± 5.7 100 ± 0.0 0.0 ± 0.0 b

50%a

0.0 ± 0.0b

12.5 ± 4.8b

na

0.0 ± 0.0 b

0.0 ± 0.0 b

na

na

93.8 ± 10.4

84.9 ± 10.3

90.9 ± 10.2

0.40

22.2 ± 14.3

b

87.5 ± 4.8

122.4 ± 15.0 22.2 ± 19.1

b

leaf root b 68.7 ± 7.0 59.6 ± 5.0 b 82.0 ± 11.3 67.2 ± 8.2 b 71.0 ± 6.5 b 79.4 ± 5.9 b 68.6 ± 10.1 b 80.7 ± 9.5 na na

Dilutions. bp