. 2020 Aug 12;68(39):10456–10488. doi: 10.1021/acs.jafc.0c02894

Table 3. Physicochemical Properties of HILs^a.

anion	cation	appearance at 25 °C^b	thermal stability and volatility^c	solubility in water	surface tension at CMC (mN/m)	adsorption in soil (%)	K_OW	refs
MCPA	tebuconazole	liquid	174 °C (T_5%)	insoluble	^d	^d	^d	(40)
MCPA	propiconazole	liquid	259 °C (T_5%)	insoluble	^d	^d	^d	(40)
MCPA	tetraalkylammonium	solids (T_m = 57–90 °C) (alkyltrimethyl-ammonium); solid (T_m = 90 °C) or liquid (dialkyldimethyl-ammonium)	190–212 °C (T_5%) (alkyltrimethyl-ammonium); 205–210 °C (T_5%) (dialkyldimethyl-ammonium)	3.3–10% (w/v) or <3.3% (w/v) (alkyltrimethyl-ammonium); limited (dialkyldimethyl-ammonium)	28.0–37.6 (alkyltrimethyl-ammonium); 26.2–28.0 (dialkyldimethyl-ammonium)	^d	^d	(16,47,49,50)
MCPA	tetraalkylphosphonium	liquid	305 °C (T_5%)	soluble	^d	^d	^d	(16)
MCPA	alkylcyclohexyl-dimethylammonium	liquids or waxes	150–214 °C (T_5%)	^d	31.2–39.4	^d	^d	(55)
MCPA	2-chloroethyl-trimethylammonium	solid (T_m = 94–96 °C)	198 °C (T_5%)	soluble	40.0	^d	^d	(16,56)
MCPA	alkyl[2-(2-hydroxyethoxy)-ethyl]dimethylammonium	liquids	187–205 °C (T_5%)	>10% (w/v)	30.7–36.9	^d	–1.00 to 1.38	(58)
MCPA	quaternary ammonium derivatives of d-glucose	liquids or waxes	164–224 °C (T_5%)	^d	32.6–34.4	^d	^d	(59)
MCPA	alkylbis(n-ethoxylated) methylammonium	solids (T_m = 52–71 °C)	225–230 °C (T_5%)	limited	34.0–38.5	^d	^d	(60)
MCPA	betainium	solid (T_m = 64–66 °C)	234 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(61)
MCPA	N-alkylbetainium	solid (T_m = 37–40 °C) or liquid	159–230 °C (T_5%)	<3.3% (w/v)	31.6–0.31.8	^d	^d	(45)
MCPA	carnitinium	liquid	190 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(61)
MCPA	acetylcholine	solid (T_m = 90–91 °C)	183 °C (T_5%)	>10% (w/v)	33.4	^d	–1.38	(62)
MCPA	[2-(methacryloyloxy)-ethyl]trimethylammonium [2-(acryloyloxy)-ethyl]trimethylammonium	liquids	195–200 °C (T_5%)	>10% (w/v)	^d	^d	^d	(63)
MCPA	dialkanoyloxyethyl-dimethylammonium	wax	208 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(63)
MCPA	derivatives of phenoxy-2-acetoxyethyl-decyldimethylammonium	liquids	^d	^d	^d	^d	^d	(21)
MCPA	1,1-dialkylpyrrolidinium	liquids	128–210 °C (T_5%)	>10% (w/v)	27.4–33.5	^d	^d	(25)
MCPA	4,4-dialkylmorpholinium	solid (T_m = 77–79 °C)	220 °C (T_5%)	soluble	^d	^d	^d	(16)
MCPA	1,1-dialkylpiperidinium	solid (T_m = 39–42 °C)	230 °C (T_5%)	soluble	^d	^d	^d	(16)
MCPA	quaternized DABCO	waxes	215–281 °C (T_5%)	>10% (w/v) or 3.3–10% (w/v)	35.6–38.9	^d	^d	(37)
MCPA	1-alkylpyridinium	liquids	200 °C (T_5%)	limited	^d	^d	^d	(16)
MCPA	bis(ammonium)	waxes	205–210 °C (T_5%)	>10% (w/v) or 3.3–10% (w/v)	^d	^d	^d	(67)
MCPA	bis(ammonium) derivatives of tebuconazole	waxes	209–223 °C (T_5%)	^d	^d	^d	^d	(68)
2,4-D	tebuconazole	wax	204 °C (T_5%)	insoluble	^d	^d	^d	(40)
2,4-D	propiconazole	liquid	239 °C (T_5%)	insoluble	^d	^d	^d	(40)
2,4-D	1,4-dimethylpiperazinium	solid (T_m = 98–100 °C)	3.0% (V)	<30–70% (pH = 5); 70–100% (pH = 7); <30% (pH = 9)	50.6	^d	3.08	(41)
2,4-D	tetraalkylammonium	solids (T_m = 55–74 °C) or waxes (alkyltrimethyl-ammonium); liquids or waxes (dialkyldimethyl-ammonium)	170–218 °C (T_5%) (alkyltrimethyl-ammonium); 204–219 °C (T_5%) (alkyltrimethyl-ammonium)	>10% (w/v) or 3.3–10% (w/v) or <3.3% (w/v) (alkyltrimethyl-ammonium); limited (dialkyldimethyl-ammonium)	28.9–36.8 (alkyltrimethyl-ammonium); 26.6–31.2 (dialkyldimethyl-ammonium)	^d	^d	(44,46−48,52)
2,4-D	tetraalkylphosphonium	liquid	260 °C (T_5%)	soluble	^d	^d	^d	(16)
2,4-D	2-chloroethyl-trimethylammonium	solid (T_m = 92–96 °C)	198 °C (T_5%)	soluble	41.5	^d	^d	(44,48)
2,4-D	alkyl-2-hydroxyethyl-dimethylammonium	solid (T_m = 86–88 °C) or wax	^d	limited or soluble	^d	^d	^d	(46)
2,4-D	quaternary ammonium derivatives of d-glucose	waxes	201–221 °C (T_5%)	^d	31.4–35.5	^d	^d	(59)
2,4-D	alkylbis(n-ethoxylated) methylammonium	solids (T_m = 49–71 °C) liquids or waxes	222–228 °C (T_5%)	>10% (w/v) or 3.3–10% (w/v)	30.4–37.2	^d	^d	(44,46,52,60)
2,4-D	betainium	solid (T_m = 70–72 °C)	237 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(61)
2,4-D	N-alkylbetainium	solid (T_m = 64–66 °C) or wax	171–228 °C (T_5%)	<3.3% (w/v)	31.5–31.7	^d	^d	(45)
2,4-D	carnitinium	wax	165 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(61)
2,4-D	acetylcholine	solid (T_m = 95–97 °C)	189 °C (T_5%)	<3.3% (w/v)	33.0	^d	–1.36	(62)
2,4-D	[2-(methacryloyloxy)-ethyl]trimethylammonium; [2-(acryloyloxy)-ethyl]trimethylammonium	waxes	198–200 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(63)
2,4-D	derivatives of phenoxy-2-acetoxyethyl-decyldimethylammonium	liquids	^d	^d	^d	^d	^d	(21)
2,4-D	1,1-dialkylpyrrolidinium	liquids	126–208 °C (T_5%)	>10% (w/v)	28.4–33.2	^d	^d	(25,46)
2,4-D	4,4-dialkylmorpholinium	liquids or waxes	^d	>10% (w/v) or limited or soluble	^d	^d	^d	(46,73)
2,4-D	1,1-dialkylpiperidinium	liquids or waxes	^d	soluble	^d	^d	^d	(46)
2,4-D	1,3-dialkylimidazolium	liquids or waxes	^d	soluble	^d	^d	^d	(46)
2,4-D	1-alkylpyridinium	wax	^d	soluble	^d	^d	^d	(46)
2,4-D	bis(ammonium)	waxes	210–219 °C (T_5%)	3.3–10% (w/v)	^d	^d	^d	(67)
2,4-D	hexamethylene-1,6-bis(3-methylimidazolium)	wax (T_m = 82–84 °C)	1.9% (V)	<30–70% (pH = 5); freely (pH = 7); 70–100% (pH = 9)	36.8	^d	4.21	(41)
MCPP	tebuconazole	liquid	200 °C (T_5%)	insoluble	^d	^d	^d	(40)
MCPP	propiconazole	liquid	245 °C (T_5%)	insoluble	^d	^d	^d	(40)
MCPP	tetraalkylammonium	liquids or waxes (alkyltrimethyl-ammonium); liquids (dialkyldimethyl-ammonium)	186–194 °C (T_5%) (alkyltrimethyl-ammonium); ^d (dialkyldimethyl-ammonium)	>10% (w/v) or 3.3–10% (w/v) or <3.3% (w/v) (alkyltrimethyl-ammonium); >10% (w/v) (dialkyldimethyl-ammonium)	31.0–38.7 (alkyltrimethyl-ammonium); ^d (dialkyldimethyl-ammonium)	^d	^d	(16,47,51)
MCPP	tetraalkylphosphonium	liquid	307 °C (T_5%)	^d	^d	^d	^d	(16)
MCPP	betainium	liquid	218 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(61)
MCPP	N-alkylbetainium	liquids	185–219 °C (T_5%)	3.3–10% (w/v) or <3.3% (w/v)	31.6–31.7	^d	^d	(45)
MCPP	carnitinium	liquid	181 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(61)
MCPP	acetylcholine	liquid	180 °C (T_5%)	<3.3% (w/v)	33.2	^d	–0.81	(62)
MCPP	[2-(methacryloyloxy)-ethyl]trimethylammonium, [2-(acryloyloxy)-ethyl]trimethylammonium	liquids	190–200 °C (T_5%)	>10% (w/v)	^d	^d	^d	(63)
MCPP	dialkanoyloxyethyl-dimethylammonium	wax	200 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(63)
MCPP	derivatives of phenoxy-2-acetoxyethyldecyl-dimethylammonium	liquids	^d	^d	^d	^d	^d	(21)
MCPP	1,1-dialkylpyrrolidinium	liquids	125–200 °C (T_5%)	>10% (w/v)	28.0–34.4	^d	^d	(25)
MCPP	1,1-dialkylpiperidinium	waxes	192–198 °C (T_5%)	3.3–10% (w/v)	^d	^d	^d	(66)
MCPP	1,3-dialkylimidazolium	liquid	252 °C (T_5%)	soluble	^d	^d	^d	(16)
MCPP	bis(ammonium)	waxes	203–205 °C (T_5%)	3.3–10% (w/v)	^d	^d	^d	(67)
dicamba	[2-(2-hydroxyethoxy)ethyl] ammonium	liquid	0.5% (V); 183 °C (T_5%)	>10% (w/v)	lack of CMC	^d	^d	(39)
dicamba	bis(3-aminopropyl)ammonium	liquid	1.0% (V); 184 °C (T_5%)	>10% (w/v)	lack of CMC	^d	^d	(39)
dicamba	tebuconazole	liquid	218 °C (T_5%)	insoluble	^d	^d	^d	(40)
dicamba	propiconazole	liquid	193 °C (T_5%)	insoluble	^d	^d	^d	(40)
dicamba	8-hydroxyquinolinium	glass	190 °C (T_5%)	^d	^d	^d	^d	(26)
dicamba	(3-aminopropyl)bis(ammonium)	solid (T_m = 76–78 °C)	199 °C (T_5%)	>10% (w/v)	lack of CMC	^d	^d	(39)
dicamba	tetraalkylammonium	solids (T_m = 72–76 °C) or waxes (alkyltrimethyl-ammonium); solids (T_m = 86 °C) or liquids or waxes (dialkyldimethyl-ammonium)	185–187 °C (T_5%) (alkyltrimethyl-ammonium); 178 °C (T_5%) (dialkyldimethyl-ammonium)	<3.3% (w/v) (alkyltrimethyl-ammonium); >10% (w/v) (dialkyldimethyl-ammonium)	36.3–37.1 (alkyltrimethyl-ammonium); ^d (dialkyldimethyl-ammonium)	^d	^d	(26,47,51)
dicamba	alkyl-2-hydroxyethyl-dimethylammonium	liquids or waxes	^d	^d	^d	^d	^d	(26)
dicamba	alkyl[2-(2-hydroxyethoxy)-ethyl]dimethylammonium	liquid or waxes	0.4% (V); 146–185 °C (T_5%)	>10% (w/v)	30.8–38.6	^d	–2.04 to 0.98	(39,58)
dicamba	alkylbis(n-ethoxylated) methylammonium	liquids or waxes	189–200 °C (T_5%)	<3.3% (w/v)	36.5	^d	^d	(26,39)
dicamba	N-alkylbetainium	solid (T_m = 28–30 °C) or liquid	184–200 °C (T_5%)	<3.3% (w/v)	30.4–32.7	^d	^d	(45)
dicamba	acetylcholine	liquid	178 °C (T_5%)	3.3–10% (w/v)	33.8	^d	0.67	(62)
dicamba	[2-(methacryloyloxy)-ethyl]trimethylammonium, [2-(acryloyloxy)-ethyl]trimethylammonium	liquids	187–192 °C (T_5%)	>10% (w/v)	^d	^d	^d	(63)
dicamba	dialkanoyloxyethyl-dimethylammonium	wax	^d	^d	^d	^d	^d	(26)
dicamba	derivatives of phenoxy-2-acetoxyethyldecyl-dimethylammonium	liquids	^d	^d	^d	^d	^d	(21)
dicamba	1,1-dialkylpyrrolidinium	liquid	185 °C (T_5%)	^d	^d	^d	^d	(26)
dicamba	4,4-dialkylmorpholinium	liquids or waxes	185 °C (T_5%)	^d	^d	^d	^d	(26,73)
dicamba	1,1-dialkylpiperidinium	liquids or waxes	188 °C (T_5%)	^d	^d	^d	^d	(26)
dicamba	1-alkyl-4-hydroxy-1-methylpiperidinium	solids (T_m = 91–98 °C) or liquids	0.2–0.3% (V); 186–192 °C (T_5%)	>10% (w/v) or 3.3–10% (w/v)	31.6–38.4	^d	^d	(39)
dicamba	1,3-dialkylimidazolium	liquids	^d	^d	^d	^d	^d	(26)
dicamba	1-alkylpyridinium	liquid	187 °C (T_5%)	^d	^d	^d	^d	(26)
dicamba	bis(ammonium)	waxes	184–195 °C (T_5%)	>10% (w/v) or 3.3–10% (w/v)	^d	^d	^d	(67)
dicamba	bis(ammonium) derivatives of tebuconazole	noncrystalline solids	201–219 °C (T_5%)	^d	^d	^d	^d	(68)
2,4-DP	tetraalkylammonium	liquids (alkyltrimethyl-ammonium); liquids (dialkyldimethyl-ammonium); wax (tetrabutyl-ammonium)	179–189 °C (T_5%) (alkyltrimethyl-ammonium); 165–190 °C (T_5%) (dialkyldimethyl-ammonium); 172 °C (T_5%) (tetrabutyl-ammonium)	<3.3% (w/v) (alkyltrimethyl-ammonium); <3.3% (w/v) (dialkyldimethyl-ammonium); >10% (w/v) (tetrabutyl-ammonium)	28.0–28.7 (alkyltrimethyl-ammonium); 27.1–28.9 (dialkyldimethyl-ammonium); 29.2 (tetrabutyl-ammonium)	^d	0.73–0.98 (alkyltrimethyl-ammonium); 0.63–0.82 (dialkyldimethyl-ammonium) 0.35 (tetrabutyl-ammonium)	(57)
2,4-DP	alkylbis(n-ethoxylated) methylammonium	liquid	221 °C (T_5%)	<3.3% (w/v)	29.1	^d	0.85	(57)
2,4-DP	acetylcholine	liquid	184 °C (T_5%)	<3.3% (w/v)	33.4	^d	0.98	(62)
2,4-DP	1,1-dialkylpiperidinium	solids (T_m = 74–87 °C) or liquids or waxes	191–206 °C (T_5%)	<3.3% (w/v)	^d	^d	–0.57 to 2.15	(65)
4-CPA	derivatives of phenoxy-2-acetoxyethyldecyl-dimethylammonium	liquids	^d	^d	^d	^d	^d	(21)
4-CPA	1,1-dialkylpyrrolidinium	liquids or waxes	123–209 °C (T_5%)	>10% (w/v)	27.5–35.6	^d	^d	(25)
clopyralid	alkylammonium	liquids	^d	0.70–49.6% (w/v) (pH = 5); 0.41–46.3% (w/v) (pH = 7); 0.72 to −45.6% (w/v) (pH = 9)	29.7–58.3	21.6–35.6	^d	(27)
clopyralid	2-benzothiazolammonium	wax	^d	0.90% (w/v) (pH = 5); 0.79% (w/v) (pH = 7); 10.3% (w/v) (pH = 9)	54.6	34.8	^d	(27)
clopyralid	imidazolium	liquid	^d	4.00% (w/v) (pH = 5); 44.0% (w/v) (pH = 7); 4.54% (w/v) (pH = 9)	61.0	32.2	^d	(27)
clopyralid	tetraalkylammonium	liquid	^d	6.0% (w/v) (pH = 5); 11.3% (w/v) (pH = 7); (10.3% (w/v) (pH = 9)	65.5	35.7	^d	(27)
clopyralid	derivatives of phenoxy-2-acetoxyethyldecyl-dimethylammonium	liquids	^d	^d	^d	^d	^d	(21)
pelargonate	tetraalkylammonium	waxes (alkyltrimethyl-ammonium); waxes (dialkyldimethyl-ammonium); liquid (tetrabutyl-ammonium)	171–193 °C (T_5%) (alkyltrimethyl-ammonium); 150–180 °C (T_5%) (dialkyldimethyl-ammonium); 153 °C (T_5%) (tetrabutyl-ammonium)	>10% (w/v) or <3.3% (w/v) (alkyltrimethyl-ammonium); >10% (w/v) or 3.3–10% (w/v) or <3.3% (w/v) (dialkyldimethyl-ammonium); >10% (w/v) (tetrabutyl-ammonium)	^d	^d	^d	(33)
pelargonate	choline	wax	186 °C (T_5%)	>10% (w/v)	^d	^d	^d	(33)
pelargonate	alkylbis(n-ethoxylated) methylammonium	wax	196 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(33)
pelargonate	N-alkylbetainium	wax	146 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(33)
pelargonate	acetylcholine	liquid	188 °C (T_5%)	>10% (w/v)	26.8	^d	1.11	(62)
pelargonate	dialkanoyloxyethyl-dimethylammonium	wax	156 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(33)
pelargonate	quaternized DABCO	liquids	^d	>10% (w/v) or 3.3–10% (w/v) or <3.3% (w/v)	26.1–29.7	^d	^d	(34)
bentazone	tetraalkylammonium	liquid (alkyltrimethyl-ammonium); wax (dialkyldimethyl-ammonium)	^d (alkyltrimethyl-ammonium); ^d (dialkyldimethyl-ammonium)	0.22% (w/v) (pH = 5); 0.23% (w/v) (pH = 7); 0.22% (w/v) (pH = 9) (alkyltrimethyl-ammonium); 3.52% (w/v) (pH = 5); 3.55% (w/v) (pH = 7); 3.48% (w/v) (pH = 9) (dialkyldimethyl-ammonium)	31.3 (alkyltrimethyl-ammonium); 34.8 (dialkyldimethyl-ammonium)	12.8 (alkyltrimethyl-ammonium); 10.3 (dialkyldimethyl-ammonium)	^d	(24)
bentazone	1,3-dialkylimidazolium	liquid	^d	8.59% (w/v) (pH = 5); 8.64% (w/v (pH = 7); 9.00% (w/v) (pH = 9)	34.3	8.7	^d	(24)
bentazone	1-alkylpyridinium	liquid	^d	0.09% (w/v) (pH = 5); 0.09% (w/v) (pH = 7); 0.08% (w/v) (pH = 9)	30.8	10.9	^d	(24)
bromoxynil	alkylammonium	wax (T_m = 97–99 °C)	0.3% (V)	0.01% (w/v) (pH = 5); 0.02% (w/v) (pH = 7); 0.01% (w/v) (pH = 9)	36.4	^d	1.03	(23)
bromoxynil	4-methylmorpholinum	liquid	5.4% (V)	3.63% (w/v) (pH = 5); 3.52% (w/v) (pH = 7); 4.02% (w/v) (pH = 9)	67.9	^d	0.59	(23)
bromoxynil	1-methyl-3H-imidazolium	wax (T_m = 63–65 °C)	4.0% (V)	0.87% (w/v) (pH = 5); 1.34% (w/v) (pH = 7); 2.76% (w/v) (pH = 9)	65.4	^d	0.45	(23)
bromoxynil	1-alkylpyridinium	wax (T_m = 89–91 °C)	0.2% (V)	0.06% (w/v) (pH = 5); 0.05% (w/v) (pH = 7); 0.05% (w/v) (pH = 9)	32.7	^d	0.97	(23)
clodinafop	choline	^d (product not isolated from postreaction mixture)	^d	^d	^d	^d	^d	(8)
diclofop	choline	^d (product not isolated from postreaction mixture)	^d	^d	^d	^d	^d	(8)
fomesafen	tetraalkylammonium	solid (T_m = 86–87 °C) (alkyltrimethyl-ammonium); liquid (dialkyldimethyl-ammonium)	^d (alkyltrimethyl-ammonium); ^d (dialkyldimethyl-ammonium)	0.001% (w/v) (pH = 5); 0.002% (w/v) (pH = 7); 0.002% (w/v) (pH = 9) (alkyltrimethyl-ammonium); 0.34% (w/v) (pH = 5); 0.46% (w/v) (pH = 7); 1.13% (w/v) (pH = 9) (dialkyldimethyl-ammonium)	29.3 (alkyltrimethyl-ammonium); 37.8 (dialkyldimethyl-ammonium)	15.3 (alkyltrimethyl-ammonium); 13.8 (dialkyldimethyl-ammonium)	2.88 (alkyltrimethyl-ammonium); 0.64 (dialkyldimethyl-ammonium)	(32)
fomesafen	1,3-dialkylimidazolium	liquid	^d	0.85% (w/v) (pH = 5); 0.97% (w/v) (pH = 7); 1.20% (w/v) (pH = 9)	34.2	13.6	0.75	(32)
fomesafen	1-alkylpyridinium	wax	^d	0.008% (w/v) (pH = 5); 0.008% (w/v) (pH = 7); 0.008% (w/v) (pH = 9)	31.2	14.1	2.49	(32)
glyphosate	tetraalkylammonium	solids (T_m = 45 °C) or liquids or waxes	148–196 °C (T_5%)	>10% (w/v) or 3.3–10% (w/v) or <3.3% (w/v)	^d	^d	^d	(31)
glyphosate	trialkylsulfonium	liquids	^d	^d	^d	^d	^d	(84)
glyphosate	alkylbis(n-ethoxylated) methylammonium	waxes	155–208 °C (T_5%)	>10% (w/v) or 3.3–10% (w/v)	^d	^d	^d	(31)
glyphosate	4,4-dialkylmorpholinium	wax	140 °C (T_5%)	>10% (w/v)	^d	^d	^d	(31)
iodosulfuron-methyl	acetylcholine	solid (T_m = 74–76 °C)	177 °C (T_5%)	>10% (w/v)	34.1	^d	0.87	(62)
MCPB	1,1-dialkylpiperidinium	liquids or waxes (T_m = 40–64 °C)	154–215 °C (T_5%)	>10% (w/v) or 3.3–10% (w/v) or <3.3% (w/v)	33.5–42.9	^d	^d	(64)
mesotrione	alkylammonium	solids (T_m = 68–97 °C) or waxes	140–179 °C (T_5%)	0.13–0.87% (w/v) (pH = 5); 0.51–1.70% (w/v) (pH = 7); 0.59–1.60% (w/v) (pH = 9)	43.7–57.9	4.5–8.0	0.92–0.97	(38)
mesotrione	1-methylpiperidinium	solid (T_m = 91 °C)	165 °C (T_5%)	1.31% (w/v) (pH = 5); 0.69% (w/v) (pH = 7); 0.88% (w/v) (pH = 9)	43.2	10.0	1.39	(38)
mesotrione	1-methyl-3H-imidazolium	solid (T_m = 96 °C)	153 °C (T_5%)	1.24% (w/v) (pH = 5); 2.21% (w/v) (pH = 7); 1.83% (w/v) (pH = 9)	44.6	7.7	1.42	(38)
mesotrione	tetraalkylammonium	liquids or waxes (T_m = 81–90 °C)	180–219 °C (T_5%)	0.18–2.42% (w/v) (pH = 5); 0.68–4.20% (w/v) (pH = 7); 0.93–4.01% (w/v) (pH = 9)	22.8–55.4	7.4–21.6	1.17–2.37	(38)
mesotrione	1-alkylpyridinium	solid (T_m = 85 °C)	202 °C (T_5%)	0.17% (w/v) (pH = 5); 0.45% (w/v) (pH = 7); 0.49% (w/v) (pH = 9)	27.5	22.6	2.43	(38)
metsulfuron-methyl	tetraalkylphosphonium	liquids	194–195 °C (T_5%)	>10% (w/v) or <3.3% (w/v)	^d	^d	^d	(29)
metsulfuron-methyl	choline	liquid	150 °C (T_5%)	>10% (w/v)	^d	^d	^d	(29)
metsulfuron-methyl	alkylbis(n-ethoxylated) methylammonium	liquid	180 °C (T_5%)	>10% (w/v)	^d	^d	^d	(29)
metsulfuron-methyl	1,1-dialkylpyrrolidinium	liquid	167 °C (T_5%)	>10% (w/v)	^d	^d	^d	(29)
metsulfuron-methyl	4,4-dialkylmorpholinium	solid (T_m = 62–64 °C)	196 °C (T_5%)	>10% (w/v)	^d	^d	^d	(29)
metsulfuron-methyl	1,1-dialkylpiperidinium	liquid	176 °C (T_5%)	>10% (w/v)	^d	^d	^d	(29)
metsulfuron-methyl	1,3-dialkylimidazolium	liquids	182–190 °C (T_5%)	>10% (w/v)	^d	^d	^d	(29)
metsulfuron-methyl	1-alkylpyridinium	liquid	195 °C (T_5%)	3.3–10% (w/v)	^d	^d	^d	(29)
nicosulfuron	tetraalkylammonium	liquids or waxes	^d	0.003–0.059% (w/v) (pH = 5); 0.012–0.064% (w/v) (pH = 7); 0.023–0.083% (w/v) (pH = 9)	14.4–43.9	^d	0.59–1.13	(30)
nicosulfuron	choline	liquid	^d	0.062% (w/v) (pH = 5); 0.046% (w/v) (pH = 7); 0.051% (w/v) (pH = 9)	41.2	^d	0.78	(30)
nicosulfuron	1-alkylpyridinium	liquid	^d	0.004% (w/v) (pH = 5); 0.003% (w/v) (pH = 7); 0.015% (w/v) (pH = 9)	19.7	^d	1.06	(30)
MCPA/dicamba (oligomeric)	alkylbis(n-ethoxylated) methylammonium	liquids or waxes	^d	^d	^d	^d	^d	(43)
MCPA/dicamba (oligomeric)	betainium	wax	202 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(61)
MCPA/glyphosate (oligomeric)	tetraalkylammonium	wax	200 °C (T_5%)	>10% (w/v)	^d	^d	^d	(42)
MCPA/glyphosate (oligomeric)	alkylbis(n-ethoxylated) methylammonium	wax	218 °C (T_5%)	>10% (w/v)	^d	^d	^d	(42)
MCPA/dicamba (DSHIL)	alkyl[2-(2-hydroxyethoxy)-ethyl]dimethylammonium	liquids	183–191 °C (T_5%)	>10% (w/v)	29.6–37.7	^d	–1.57 to 1.13	(58)
MCPA/glyphosate (DSHIL)	tetraalkylammonium	solid (T_m = 15, 40 °C) or wax (alkyltrimethyl-ammonium); liquids (dialkyldimethyl-ammonium)	150–155 °C (T_5%) (alkyltrimethyl-ammonium); 159–160 °C (T_5%) (dialkyldimethyl-ammonium)	>10% (w/v) or <3.3% (w/v) (alkyltrimethyl-ammonium); >10% (w/v) or 3.3–10% (w/v) (dialkyldimethyl-ammonium)	^d	^d	^d	(42)
MCPA/glyphosate (DSHIL)	alkylbis(n-ethoxylated) methylammonium	wax	215 °C (T_5%)	>10% (w/v)	^d	^d	^d	(42)
dicamba/glyphosate (DSHIL)	tetraalkylammonium	solid (T_m = 85 °C)	188 °C (T_5%)	>10% (w/v)	^d	^d	^d	(42)
dicamba/glyphosate (DSHIL)	tetraalkylphosphonium	liquid	177 °C (T_5%)	<3.3% (w/v)	^d	^d	^d	(42)
dicamba/glyphosate (DSHIL)	alkylbis(n-ethoxylated) methylammonium	wax	213 °C (T_5%)	>10% (w/v)	^d	^d	^d	(42)

Herbicides have been ordered in decreasing number of manuscripts. Table does not include salts with melting points greater than 100 °C. T_m, melting point.

Singular form, only one compound; plural form, more than one compound.

T_5%, decomposition temperature of 5% sample; V, volatility rate at 75 °C after 12 h.

Not tested.

Table 3. Physicochemical Properties of HILsa.

Table 3. Physicochemical Properties of HILs^a.