Ionic liquids based on 2-chloroethyltrimethylammonium chloride (CCC) as plant growth regulators

Article abstract of DOI:10.2478/s11532-013-0309-1

Plant growth regulator - 2-chloroethyltrimethylammonium chloride (CCC) was converted into ionic liquid in the metathesis reaction. New forms of CCC as ILs were stable in air as well in contact with water and organic solvents. The biological action of the

Full text of DOI:10.2478/s11532-013-0309-1

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Central European Journal of Chemistry
Ionic liquids based on
2-chloroethyltrimethylammonium
chloride (CCC) as plant growth regulators
Research Article
Tadeusz Praczyk1, Katarzyna Zakrocka1, Danuta Wyrzykowska1,
0LFKDïꢀ1LHPF]DN2, Juliusz Pernak2*
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Received 9 April 2013; Accepted 28 June 2013
Abstract:ꢀ
Plant growth regulator - 2-chloroethyltrimethylammonium chloride (CCC) was converted into ionic liquid in the metathesis reaction. New
forms of CCC as ILs were stable in air as well in contact with water and organic solvents. The biological action of the cation (CCC) in ILs
ZDVꢀSUHVHUYHGꢁꢀ7\SHꢀRIꢀDQLRQꢀGHWHUPLQHGꢀK\GURSKRELFLW\ꢀDQGꢀK\GURSKLOLFLW\ꢀRIꢀWKHꢀZKROHꢀPROHFXOHꢀDQGꢀLWꢀDOVRꢀLQĠXHQFHGꢀWKHꢀELRORJLFDOꢀ
activity of the plant growth regulator. All of the investigated salts retarded growth of winter wheat stems and most of them increased yield
at the same time, when compared to control and standard 2-chloroethyltrimethylammonium chloride.
Keywords: ,RQLFꢀOLTXLGVꢀľꢀ0HWDWKHVLVꢀUHDFWLRQꢀľꢀ$QWLꢁJLEEHUHOOLQVꢀľꢀ&KORUPHTXDWꢀFKORULGH
© Versita Sp. z o.o.
structures, mostly GA5 derivatives [1@ꢁꢀ7KHꢀ¿UVWꢀW\SHꢀRIꢀ
PGRs is widely used in agronomic crops to increase
1. Introduction
Lodging in cereals refers to the displacement of the resistance of cereals to lodging and to reduce excessive
stem from its vertical position and leaning it towards the growth in cotton. Onium-type compounds block the
soil. Stem lodging is usually caused by wind, low stem cyclases copalyl-diphosphate synthase and ent-kaurene
resistance or weight of water accumulated in the mature synthase in the early steps of gibberellins metabolism
ears. Plant growth retardants (PGRs) could be used to [1].
HI¿FLHQWO\ꢀSUHYHQWꢀWKLVꢀDGYHUVHꢀSKHQRPHQRQꢁꢀ
Chlormequat
chloride
–
0RVWꢀ3*5VꢀDSSOLHGꢀLQꢀ¿HOGꢀFURSVꢀLQKLELWꢀJLEEHUHOOLQꢀ 2-chloroethyltrimethylammonium chloride (CCC), is a
(GA) biosynthesis. At present four different types of these compound which possesses one positively charged
inhibitors are known: onium-type compounds, which nitrogen atom and has an activity in reducing longitudinal
have a positively charged ammonium, phosphonium or shoot growth without lowering the plant productivity.
sulphonium group (e.g. chlormequat chloride, mepiquat This quaternary ammonium chloride belongs to a group
chloride, chlorphonium andAMO-1618), compounds with of popular chemical compounds also known as ‘quats’
a N-containing heterocycle (e.gꢁꢀDQF\PLGROꢂꢀÀXUSULPLGROꢂꢀ [2]. Chlormequat chloride was prepared in 1910 [3] and
tetcyclacis, paclobutrazol, uniconazole), structural was described as plant growth regulator by N. E. Tolbert
mimics of 2-oxoglutaric acid (e.g. acylcyclohexanediones in 1960 [4,5]. CCC increases resistance to lodging by
compounds such as prohexadione-Ca and trinexapac- inhibiting cell elongation, as a result producing shorter
ethyl), 16,17-Dihydro-GAs which represent different DQGꢀ VWURQJHUꢀ VWHPVꢁꢀ ,Wꢀ DOVRꢀ LQWHQVL¿HVꢀ FKORURSK\OOꢀ
* E-mail: juliusz.pernak@put.poznan.pl
1816

T. Praczyk et al.
formation and root development and is used to increase
yields in wheat, rye, oats and triticale. Moreover, CCC is
DOVRꢀDSSOLHGꢀWRꢀLQFUHDVHꢀODWHUDOꢀEUDQFKLQJꢀDQGꢀÀRZHULQJꢀ
in some ornamental plants and to increase fruit setting
in pears, olives, vines and tomatoes [6].
2.1.1. Preparation
of
ionic
liquids
with
2-chloroethyltrimethylammonioum cation:
,Qꢀ Dꢀ URXQGꢈERWWRPꢀ ÀDVNꢂꢀ ꢉꢁꢉꢊꢀ PROꢀ RIꢀ VRGLXPꢀ
WHWUDÀXRURERUDWHꢀ ZDVꢀ GLVVROYHGꢀ LQꢀ ꢃꢋꢀ P/ꢀ RIꢀ
distilled water. Then
a
stoichiometric amount of
chloride was
,Qꢀꢃꢄꢄꢅꢀ:RUOGꢀ+HDOWKꢀ2UJDQL]DWLRQꢀFODVVL¿HGꢀ&&&ꢀ
as slightly hazardous - LD50 in rats, mice hamsters
guinea-pigs and monkeys between 200-1000 mg kg-1
of bodyweight indicate its moderate oral toxicity [7].
Maximum residue levels (MRLs) have been established
by European Union commission for CCC accordingly
to its noxiousness. For instance, maximum residue
limits of CCC in food products are 10 mg kg-1 in oat
and pear, 3 mg kg-1 in wheat and rye, and 0.5 mg kg-1
in milk and milk products [8,9]. In 1989 Danielsen et
al. [10] suggested that CCC may negatively affect
mammalian reproduction. More recently, it was shown
that CCC did not affect reproduction in female mice [11]
whereas reproduction in male mice was compromised
[6,10,11]. On the contrary, current reports revealed
that chlormequat chloride could not be proven to be
detrimental to the male pig reproduction [6].
,RQLFꢀ OLTXLGVꢀ ꢆ,/Vꢇꢀ FDQꢀ EHꢀ GH¿QHGꢀ DVꢀ WKHꢀ LRQLFꢀ
compounds consisting of a cation and anion. Their
melting points are low and they exist in a liquid form
below the temperature of 100°C [12-17]. Potentially,
there is a possibility of selection of appropriate ions
to obtain an ionic liquid having the desired properties.
7KLVꢀMXVWL¿HVꢀWKHLUꢀZLGHꢀUDQJHꢀRIꢀDSSOLFDWLRQVꢀDVꢀZRRGꢀ
preservatives, surfactants, disinfectants, antistatic or
softening substances, extractants or media of chemical
reactions. It should be noted that, being non-volatile,
QRQꢈÀDPPDEOHꢀ DQGꢀ WKHUPDOO\ꢀ VWDEOHꢀ WKH\ꢀ SROOXWHꢀ WKHꢀ
environment less than the conventional solvents.
Extensive research has already led to the emergence
of the third generation of ionic liquids. In this group, in
addition to certain physical (I generation) and chemical
(II generation) properties, appears also an expected
biological activity [18,19]. III generation of ILs has
recently expanded to include herbicidal ionic liquids,
that due to their high activity, are novel salts with a high
potential of application [20-22].
2-chloroethyltrimethylammonioum
added and the mixture was stirred for 1 hour at room
temperature. The product, which precipitated as
crystalline, white solid, was separated and washed with
distilled water until no chloride anions were present
in water. Then the product was dried under reduced
pressure at 45oC for 24 h.
,Qꢀ Dꢀ URXQGꢈERWWRPꢀ ÀDVNꢂꢀ HTXLSSHGꢀ ZLWKꢀ Dꢀ GURSSLQJꢀ
funnel, 0.03 mol of sodium (or potassium) salt of acids:
nicotinic, benzoic, salicylic and propionic was dissolved in
30mLofdistilledwater.Thenastoichiometricamountofthe
aqueous solution of 2-chloroethyltrimethylammonioum
chloride was added and the mixture was stirred for
3 hours at room temperature. The water was evaporated
using a rotary evaporator and the residue was dissolved
in isopropanol. The product, deposited in isopropanol
phase, was separated from insoluble inorganic salts.
After removal of isopropanol the product was dried under
reduced pressure at 45oC for 24 h.
,Qꢀ Dꢀ URXQGꢈERWWRPꢀ ÀDVNꢂꢀ HTXLSSHGꢀ ZLWKꢀ UHÀX[ꢀ
condenser and dropping funnel, 0.01 mol of trisodium
phosphate was dissolved in 30 mL of distilled water.
Then a 0.03 mol of 2-chloroethyltrimethylammonioum
chloride was added and the mixture was stirred for
3 hours at room temperature. The water was evaporated
using a rotary evaporator and the residue was dissolved
in methanol. The product, which deposited in methanol
phase, was separated from insoluble inorganic salts.
After removal of methanol the product was dried under
reduced pressure at 45oC for 24 h.
,Qꢀ Dꢀ URXQGꢈERWWRPꢀ ÀDVNꢂꢀ ꢉꢁꢉꢊꢀ PROꢀ RIꢀ
dodecylbenzenesulfonic acid was dissolved in
30 mL of distilled water. Then a stoichiometric amount
of 2-chloroethyltrimethylammonioum chloride was
added and the mixture was stirred for 3 hours at room
WHPSHUDWXUHꢁꢀ7KHꢀSURGXFWꢂꢀZKLFKꢀSUHFLSLWDWHGꢀDVꢀÀRFN\ꢂꢀ
white solid, was separated and washed with distilled
water until no chloride anions were present in water.
Then the product was dried under reduced pressure at
45oC for 24 h.
2. Experimental procedure
ꢀꢁ&KORURHWK\OWULPHWK\ODPPRQLXPꢂ WHWUDÀXRURERUDWHꢂ
1
2.1. General
(1) H NMR (DMSO-d6) į (ppm) 3.21 (s, 9H), 3.91 (t,
1H NMR spectra were recorded on
a
Mercury J = 6.8 Hz, 2H), 4.09 (t, J = 7.1 Hz, 2H); 13C NMR į
Gemini 300 spectrometer operating at 300 MHz with (ppm) 35.9, 53.2, 65.6. Elemental analysis calcd (%) for
tetramethylsilane as the internal standard. 13C NMR C5H13BClF4N (209.42): C 28.68, H 6.26, N 6.69; found:
spectra were obtained with the same instrument at C 28.97, H 6.01, N 6.96.
75 MHz. CHN elemental analyses were performed at A.
Mickiewicz University, Poznan (Poland).
Tris(2-chloroethyltrimethylammonium)
phosphate
(2) 1H NMR (D2O, 298K, 300 MHz) į (ppm) 3.17 (s, 27H),
1817

Ionic liquids based on 2 chloroethyltrimethylammonium
chloride (CCC) as plant growth regulators
3.85 (t, J = 7.2 Hz, 6H), 4.03 (t, J = 6.4 Hz, 6H); 13C NMR (Leicester, UK) unit, under nitrogen. Samples between
(D2O, 298K, 75 MHz) į (ppm) 36.5, 54.0, 66.1; 31P 5 and 15 mg were placed in aluminum pans and heated
NMR (D2O, 298K, 121 MHz) į (ppm) 1.5(s); Elemental from 25 to 120°C at a heating rate of 10°C min-1 and
analysis calcd (%) for C15H39Cl3N3O4P (462.82): C 38.93, cooled with an intracooler at a cooling rate of 10°C min-1
H 8.49, N 9.08; found: C 38.57, H 8.21, N 8.82.
to -100°C. Thermogravimetric analysis was performed
2-Chloroethyltrimethylammonium propionate (3) H using a Mettler Toledo Stare TGA/DSC1 unit (Leicester,
NMR (DMSO-d6) į (ppm) 0.95 (t, J = 6.9 Hz, 3H), 2.29 UK) under nitrogen. Samples between 2 and 10 mg
(q, J = 5.4 Hz, 2H), 3.22 (s, 9H), 3.84 (t, J = 6.7 Hz, 2H), were placed in aluminum pans and heated from 30 to
4.13 (t, J = 7.0 Hz, 2H); 13C NMR į (ppm) 9.7, 27.6, 450°C at the heating rate of 10°C min-1.
35.9, 52.5, 65.7, 180.3. Elemental analysis calcd (%) for
1
C8H18ClNO2 (195.69): C 49.10, H 9.27, N 7.16; found: C
49.48, H 9.03, N 6.89.
2.3. Biological activity
Field trials were performed in 2011 at Experimental
Station in Winna Gora (western part of Poland) on winter
wheat cultivar Zyta, which was cultivated according to
the conventional agricultural practice. The experimental
design was a randomized block with four replications and
the plot size was 16.5 m2. All tested salts were dissolved
in water or alcohol and used at the dose rate of 400 g ha-1
of CCC. The standard product was a growth regulator
containing 2-chloroethyltrimethylammonium chloride
ꢆ&&&ꢇꢀ ±ꢀ$QW\Z\OHJDF]ꢀ 3á\QQ\ꢀ ꢅꢌꢋꢀ 6/ꢁꢀ$OOꢀ WUHDWPHQWVꢀ
ZHUHꢀDSSOLHGꢀDWꢀWKHꢀVWDJHꢀRIꢀWKHꢀ¿UVWꢀGHWHFWDEOHꢀQRGHꢀRIꢀ
wheat growth (BBCH 31) using knapsack sprayer with
;5ꢀꢃꢃꢉꢉꢊꢀÀDWꢈIDQꢀQR]]OHVꢀGHOLYHULQJꢀꢌꢉꢉꢀ/ꢀKD-1 of spray
solution at 0.3 MPa of an operating pressure. Shortly
before harvesting the height of 25 randomly chosen
winter wheat stems were measured within each plot from
the ground to the top of ear. The effect of all tested salts
was compared to the untreated sample. Grain yield from
the plot was harvested using combine harvester. Grain
from experimental plots was weighted and its moisture
was determined. The yield obtained was converted to
t ha-1 taking into account the standard grain moisture
FRQWHQWꢀRIꢀꢃꢍꢎꢁꢀ7KHꢀGDWDꢀIURPꢀ¿HOGꢀWULDOVꢀZHUHꢀDQDO\]HGꢀ
by ANOVA. Tukey’s test was used for the comparison
of averages and LSD was determined on the level of
5%. All calculations were performed using Agriculture
Research Manager (ARM) software.
ꢀꢁ&KORURHWK\OWULPHWK\ODPPRQLXPꢂ EHQ]RDWHꢂ (4)
1H NMR (DMSO-d6) į (ppm) 3.30 (s, 9H), 3.93 (t, J =
6.8 Hz, 2H), 4.19 (t, J = 7.2 Hz, 2H), 7.53 (d, J = 7.7
Hz, 1H), 7.64 (t, J = 7.5 Hz, 1H), 7.98 (dd, J1,2 = 6.8
Hz, J1,3 = 1.2 Hz, 1H) ; 13C NMR į (ppm) 36.9, 53.8,
65.9, 128.2, 128.6, 129.1, 129.3, 131.2, 132.7, 167.3.
Elemental analysis calcd (%) for C12H18ClNO2 (243.73):
C 59.13, H 7.44, N 5.75; found: C 58.86, H 7.23,
N 5.47.
2 - C h l o r o e t h y l t r i m e t h y l a m m o n i u m
ꢀꢁK\GUR[\EHQ]RDWHꢂ (5) 1H NMR (DMSO-d6) į (ppm)
3.18 (s, 9H), 3.80 (t, J = 6.9 Hz, 2H), 4.12 (t, J = 6.9 Hz,
2H), 6.60 (t, J = 8.7 Hz, 1H), 6.62 (d, J = 6.9 Hz, 1H),
7.14 (t, J = 6.3 Hz,1H), 7.68 (dd, J1,2 = 7.5 Hz, J1,3 = 1.8
Hz, 1H); 13C NMR į (ppm) 36.4, 52.7, 65.0, 115.8, 115.9,
120.7, 129.9, 131.3, 163.0, 171.5. Elemental analysis
calcd (%) for C12H18ClNO3 (259.73): C 55.49, H 6.99, N
5.39; found: C 55.73, H 7.22, N 5.04.
2-Chloroethyltrimethylammonium
FDUER[\ODWHꢂ (6) H NMR (DMSO-d6) į (ppm) 3,26 (s,
pyridine-3-
1
9H), 3.87 (t, J = 6.4 Hz, 2H), 4.15 (t, J = 6.5 Hz, 2H),
7.55 (t, J = 7.7 Hz, 1H), 8.41 (dd, J1,2 = 7.4 Hz, J1,3
=
1.6 Hz, 1H), 8.99 (d, J = 5.0 Hz, 1H), 9.23 (s, 1H);
13C NMR į (ppm) 37.1, 53.7, 65.5, 123.5, 131.4, 137.0,
152.4, 155.6, 175.2. Elemental analysis calcd (%) for
C11H17ClN2O2 (244.72): C 53.99, H 7.00, N 11.45; found:
C 53.65, H 7.32, N 11.19.
2 - C h l o r o e t h y l t r i m e t h y l a m m o n i u m
GRGHF\OEHQ]HQHVXOIRQDWHꢂ (7) 1H NMR (DMSO-d6) į 3. Results and discussion
(ppm) 0.88 (t, J = 6.8 Hz, 3H), 1.26 (m, 18H), 1.69 (m,
2H), 2.61 (t, J = 6.3 Hz, 2H), 3.22 (s, 9H), 3.83 (t, J = 7.4 Usinga2-chloroethyltrimethylammoniumchloride(CCC)
Hz, 2H), 4.16 (t, J = 6.5 Hz, 2H), 7.18 (d, J= 6.1 Hz, 2H), as the source of the cation, 7 new quaternary ammonium
7.51 (d, J =6.3 Hz, 2H); 13C NMR į (ppm) 13.9, 22.1, salts were obtained in metathesis reaction (Scheme 1)
25.5, 28.7, 28.8, 29.1, 31.3, 36.2 36.7, 53.1, 65.1, 125.5, with the yield exceeding 90%. As a result, chloride anion
128.0, 137.8, 145.4. Elemental analysis calcd (%) for KDVꢀEHHQꢀUHSODFHGꢀE\ꢀIROORZLQJꢀDQLRQVꢏꢀWHWUDÀXRURERUDWHꢀ
C23H42ClNO3S (448.10): C 61.65, H 9.45, N 3.13; found: (1), phosphate (2), propionate (3), benzoate (4),
C 61.32, H 9.17, N 3.28.
2-hydroxybenzoate
(salicylate)
(5),
pyridine-3-
carboxylate (nicotinate) (6), dodecylbenzenesulfonate
(7). The prepared salts are presented in Table 1.
2.2. Thermal analysis
Thermal transitions of prepared salts were determined They were stable in air as well in contact with water
by DSC, with a Mettler Toledo Stare TGA/DSC1 RUꢀSRSXODUꢀRUJDQLFꢀOLTXLGVꢀDQGꢀZHUHꢀQRQꢈÀDPPDEOHꢁꢀ$Wꢀ
1818

T. Praczyk et al.
l
C
A
N
l
C
l
C
H
H
C
H
H
C
3
3
+
+
X l
C
N
XA
H
3C
C
H
3C
C
3
3
w ere
h
=
a
H N K
, ,
X
Scheme 1. Synthesis of 2-chloroethyltrimethylammonium salts.
Table 1. Prepared salts.
Salt
Anion
Yield [%]
State at room temperature
Solubility in water
1
2
3
4
5
6
7
BF4-
PO43-
97
96
97
94
93
98
96
solid
solid
limited
total
C2H5COO-
liquid
solid
total
C6H5COO-
total
2-HOC6H4COO-
C5H4NCOO-
4-C12H25C6H4SO3-
solid
total
solid
total
grease
insoluble
Table 2. The chemical shifts in 1H NMR.
elevated temperature, the synthesized salts were found
to dissolve in short-chain alcohols and water (except
salt 7 and 1) but not in hexane or ether. Type of anion
determined solubility of the salt in water. CCC is very
soluble only in water and methanol and practically
insoluble in many organic solvents such as isopropanol,
acetone, acetonitrile or chloroform. Through the
exchange reaction of the chloride anion obtained salts
gained a solubility in some organic solvents such as
isopropanol (3-6), acetone (2,4,5,7) and acetonitrile (2-
Salt
Cation – characteristic protons
N(CH3)3
NCH2
ClCH2
1
3.21(s)
3.17(s)
3.22(s)
3.30(s)
3.18(s)
3.26(s)
3.22(s)
3.21(s)
3.91(t)
3.85(t)
3.84(t)
3.93(t)
3.80(t)
3.87(t)
3.83(t)
3.84(t)
4.09(t)
4.03(t)
4.13(t)
4.19(t)
4.12(t)
4.15(t)
4.16(t)
4.12(t)
2
3
4
5
1
5,7).The prepared salts were characterized by H and
13C NMR and elemental analysis. The 1H NMR spectra of
the starting chloride and the other salts indicated various
chemical shifts (Table 2). The differences reached
to 0.13 ppm for N(CH3)3 protons, 0.13 ppm for NCH2
protons and 0.16 ppm for ClCH2 protons, respectively.
Thermal stability of salts 1-7 is presented in the
Table 3. The studied salts were thermally stable between
145°C and 270°C. Such a broad range indicates how
strong was the effect of anion on thermal stability of
synthesized compounds. The most stable proved to be
WHWUDÀXRURERUDWHꢀꢆ1) and dodecylbenzenesulfonate (7).
Salts with the organic anion 3-7ꢀFRXOGꢀEHꢀTXDOL¿HGꢀDVꢀ
ILs , because their melting points were below 100°C.
6
7
CCC
s – singlet, t – triplet, shift in ppm
Table 3. Thermal properties of CCC derivatives.
a
b
c
d
e
Salt
Tg
Tcyst
Tm
Tonset5%
(oC)
Tonset
(oC)
(oC)
(oC)
(oC)
1
-21
---
---
---
---
---
---
---
---
---
209
199
---
256
189
145
175
188
150
270
250
282
228
240
255
233
232
373
254
2
3
-84
---
CCC unlike the
2
chloroethyltrimethylammonium
4
84
99
88
---
WHWUDÀXRURERUDWHꢀ ꢆ1), propionate (3) and salicylate (5)
does not have a glass transition temperature. It also
has no melting point on the contrary to the obtained
salts (1,2,4-6), and is decomposed at a temperature of
250°C.
The newly synthesized forms of CCC retarded
the growth of winter wheat stems. This effect varied
depending on the type of anion. The plants treated
with salts 1-7 were by 2.3 cm to 7.8 cm (3.1-10.4%)
5
15
---
6
7
---
CCC
---
---
a
Tg - glass transition temperature; b
T
– temperature of crystallization; c
cryst
T
- melting point; db7
bꢀbGHFRPSRVLWLRQꢁꢁWHPSHUDWXUHꢁRIꢁꢂꢃꢁVDPSOHꢄꢁe
Tomnset - decompositionotnesemt5%perature of 50% sample
1819

Ionic liquids based on 2 chloroethyltrimethylammonium
chloride (CCC) as plant growth regulators
7KHꢀVWUXFWXUHꢀRIꢀWKHꢀDQLRQꢀDOVRꢀKDGꢀDQꢀLQÀXHQFHꢀRQꢀ
the yield of winter wheat. The yield from the untreated
control amounted to 6.28 t ha-1, while the yield from plots
treated with new forms of CCC ranged from 6.09 to
6.95 t ha-1. ILs 4, 5 and 6 were the most active. The
treatments with ILs provided an increase of yield
by 0.59-0.67 t ha-1 (9.4-10.7%) compared to the
control. Generally it can be concluded that the yield
from treatments with salts containing organic anions
was higher compared to the results obtaining for
salts with inorganic anions. We can say that the best
biological properties exhibited ILs with phenyl anion
(salts 4, 5, 7). None of the new forms of CCC caused
damage to crop plants.
Table 4. 7KHꢀLQĠXHQFHꢀRIꢀVDOWVꢀZLWKꢀꢁꢂFKORURHWK\OWULPHWK\ODPPRQLXP ꢀ
ꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀFDWLRQꢀRQꢀWKHꢀVWHPVꢀOHQJWKꢀDQGꢀ\LHOGꢀRIꢀWKHꢀZLQWHUꢀZKHDWꢃ
Salt
Dose
(kg ha-1)
Stem length
(cm)
Yield
(t ha-1)
1
2
3
4
5
6
7
0.7
0.5
0.6
0.8
0.8
0.8
1.5
68.5 b*
70.0 a
69.2 b
71.9 a
69.5 b
72.6 a
67.1 b
6.26 cde
6.57 bcd
6.09 e
6.95 ab
6.87 ab
6.93 ab
6.65 bc
CCC
0.6
-
70.7 a
74.9 a
6.13 de
(commercial)
Untreated
check
6.28 cde
4. Conclusions
ꢅꢁWKHꢁVDPHꢁOHWWHUꢁLQꢁDꢁFROXPQꢁPHDQVꢁQRꢁVLJQLğFDQWꢁGLIIHUHQFHVꢁEHWZHHQꢁ
treatments
Popular
plant
growth
regulator
-
shorter than the control. Salt 1 and ILs 3, 5, 7 turned 2-chloroethyltrimethylammonium chloride (CCC) can
out to be the most active substances (Table 4) and be converted into ionic liquid in the metathesis reaction.
were more active than the CCC-containing commercial New forms of CCC as ILs were stable in air as well as in
product. Winter wheat plants from the plots treated contact with water and organic solvents. The biological
with these compounds were by 5.4 to 10.4 percent action of the cation in ILs has been preserved. The type
shorter compared to the untreated check and by 1.7 to of anion determines hydrophobicity and hydrophilicity of
5.1 percent shorter as compared to the plants treated the whole molecule and dictates the activity as a plant
with the commercial product. It should be noted that to growth regulator. The positive effect of ILs treatments on
effectively limit the growth of winter wheat, the dose of the yield of winter wheat was noted.
active part (2-chloroethyltrimethylammonium cation)
in ILs was 400 g ha-1 while recommended doses for
present formulation of CCC are between 700 and
Acknowledgements
1400 g ha-1. The higher biological activity, which we
found for the new forms of CCC, made possible the
reduction of their dose, which is highly important from a
point of view of integrated crop protection system.
This work was supported by grant No N N 209 754840
(National Science Centre, Poland).
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