Electronic Supplementary Information

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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information Bis(ammonium) ionic liquids with herbicidal anions Michał Niemczak a, Rafał Giszter a, Kamil Czerniak a, Katarzyna Marcinkowska b, Filip Walkiewicz a a Department of Chemical Technology, Poznan University of Technology, Poznan, Poland b Institute of Plant Protection - National Research Institute, Poznan, Poland 1

2 Figure S1. 1 H NMR spectrum of 1a (dodecamethylene-1,12-bis(dimethyldecylammonium) di[2-(4-chloro-2-methylphenoxy)propioniate]). C 10 H 21 N N C 10 H CH 3 2

3 Figure S2. 13 C NMR spectrum of 1a (dodecamethylene-1,12-bis(dimethyldecylammonium) di[2-(4-chloro-2-methylphenoxy)propioniate]). C 10 H 21 N N C 10 H CH 3 3

4 Figure S3. 1 H NMR spectrum of 1b (dodecamethylene-1,12-bis(dimethyldecylammonium) di[3.6-dichloro-2-methoxybenzoate]). C 10 H 21 N N C 10 H

5 Figure S4. 13 C NMR spectrum of 1b (dodecamethylene-1,12-bis(dimethyldecylammonium) di[3.6-dichloro-2-methoxybenzoate]). C 10 H 21 N N C 10 H

6 Figure S5. 1 H NMR spectrum of 2a (oxybis(ethylene)bis(dimethyldecylammonium) di[2-(4-chloro-2-methylphenoxy)propioniate]). C 10 H 21 N 2 (CH 2 ) 2 N C10 H 21 6

7 Figure S6. 13 C NMR spectrum of 2a (oxybis(ethylene)bis(dimethyldecylammonium) di[2-(4-chloro-2-methylphenoxy)propioniate]). H 3 C C 10 H 21 N H 3 C N (CH2 ) 2 (CH 2 ) 2 N C10 H 21 H 3 C N 7

8 Figure S7. 1 H NMR spectrum of 2b (oxybis(ethylene)bis(dimethyldecylammonium) di[3.6-dichloro-2-methoxybenzoate]). C10 C 10 H 21 N N H 21 2 (CH 2 ) 2 8

9 Figure S8. 13 C NMR spectrum of 2b (oxybis(ethylene)bis(dimethyldecylammonium) di[3.6-dichloro-2-methoxybenzoate]). C10 C 10 H 21 N N H 21 2 (CH 2 ) 2 9

10 Figure S9. 1 H NMR spectrum of 2c (oxybis(ethylene)bis(dimethyldecylammonium) di[(4-chloro-2-methylphenoxy)acetate]). C 10 H 21 N 2 (CH 2 ) 2 N C10 H 21 10

11 Figure S C NMR spectrum of 2c (oxybis(ethylene)bis(dimethyldecylammonium) di[(4-chloro-2-methylphenoxy)acetate]). C10 C 10 H 21 N N H 21 H (CH2 CH ) 3C10 3 C 2 (CH 2 ) 2 CH C 3 10 H 21 N N H 21 2 (CH 2 ) 2 Figure S11. 1 H NMR spectrum of 2d (oxybis(ethylene)bis(dimethyldecylammonium) di[(2,4-dichlorophenoxy)acetate]). 11

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13 Figure S C NMR spectrum of 2d (oxybis(ethylene)bis(dimethyldecylammonium) di[(2,4-dichlorophenoxy)acetate]). C 10 H 21 N 2 (CH 2 ) 2 C10 N H 21 H 3 C N H 3 C N 13

14 Figure S13. 1 H NMR spectrum of 3a (ethylenebis(oxyethylene)bis(dimethyldecylammonium) di[2-(4-chloro-2-methylphenoxy)propioniate]). C 10 H 21 N 2 N C 10 H 21 (CH 2 ) 2 (CH2 ) 2 14

15 Figure S C NMR spectrum of 3a (ethylenebis(oxyethylene)bis(dimethyldecylammonium) di[2-(4-chloro-2-methylphenoxy)propioniate]). C 10 H 21 N 2 N C 10 H 21 (CH 2 ) 2 (CH2 ) 2 15

16 Figure S15. 1 H NMR spectrum of 3b (ethylenebis(oxyethylene)bis(dimethyldecylammonium) di[3.6-dichloro-2-methoxybenzoate]). C 10 H 21 N N C 10 H (CH 2 ) 2 (CH2 ) 2 16

17 Figure S C NMR spectrum of 3b (ethylenebis(oxyethylene)bis(dimethyldecylammonium) di[3.6-dichloro-2-methoxybenzoate]). C 10 H 21 N N C 10 H CH (CH 2 ) 2 (CH2 ) 2 3 C 10 H 21 N N C 10 H 21 H (CH2 ) 12 3 C (CH 2 ) 2 (CH2 ) 2 CH 3 Figure S17. 1 H NMR spectrum of 3c (ethylenebis(oxyethylene)bis(dimethyldecylammonium) di[(4-chloro-2-methylphenoxy)acetate]). 17

18 Figure S C NMR spectrum of 3c (ethylenebis(oxyethylene)bis(dimethyldecylammonium) di[(4-chloro-2-methylphenoxy)acetate]). C 10 H 21 N 12 N C 10 H 21 (CH 2 ) 2 (CH2 ) 2 18

19 Figure S19. 1 H NMR spectrum of 3d (ethylenebis(oxyethylene)bis(dimethyldecylammonium) di[(2,4-dichlorophenoxy)acetate]). C 10 H 21 N 12 N C 10 H 21 (CH 2 ) 2 (CH2 ) 2 19

20 Figure S C NMR spectrum of 3d (ethylenebis(oxyethylene)bis(dimethyldecylammonium) di[(2,4-dichlorophenoxy)acetate]). C 10 H 21 N 12 N C 10 H 21 (CH 2 ) 2 (CH2 ) 2 20

21 Figure S21. DSC thermogram of 1a 21

22 Figure S22. DSC thermogram of 1b 22

23 Figure S23. DSC thermogram of 2a-2d 23

24 Figure S24. DSC thermogram of 3a-3d 24

25 Figure S25. TGA thermogram of 1a and 1b 25

26 Figure S26. TGA thermogram of 2a-2d 26

27 Figure S27. TGA thermogram of 3a-3d 27

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29 Table S1. Efficacy tests for bis(ammonium) HILs in the greenhouse experiments. Salt CHEAL - Lambsquarters (Chenopodium album L.) SINAL - White mustard (Sinapis alba L.) Fresh weight reduction (%) 2a b c d a b c d MCPA a Dicamba a ,4-D a a the commercial herbicides 29

NJC Accepted Manuscript

NJC Accepted Manuscript This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published