Table 6. Overview of Toxicity Studies on HILsa.
| anion | cation | toxicity and impact on desired plants | ref |
|---|---|---|---|
| MCPA | tebuconazole | at 10 ppm, fungistatic activity against F. culmorum and M. nivale; no damage toward winter wheat (AI 170 g/ha) | (40) |
| MCPA | propiconazole | at 10 ppm, strong inhibition of F. culmorum, M. nivale, B. cinerea, and S. sclerotiorum mycelia growth; no damage toward winter wheat (AI 170 g/ha) | (40) |
| MCPA | tetraalkylammonium | acute oral LD50 for rats, 300 to >2000 mg/kg; AI 200–500 g/ha, winter wheat 7.88–8.28 t/ha (untreated control, 7.40 t/ha) | (16) |
| MCPA | 2-chloroethyl-trimethylammonium | acute oral LD50 for rats, 300–2000 mg/kg; shortening of wheat stems, increased resistance to lodging | (16) |
| MCPA | 2-chloroethyl-trimethylammonium | growth inhibition of winter wheat, 2–6% | (56) |
| MCPA | betainium | acute oral LD50 for rats, 300–2000 mg/kg | (61) |
| MCPA | N-alkylbetainium | acute oral LD50 for rats, 300–2000 mg/kg | (45) |
| MCPA | carnitinium | acute oral LD50 for rats, 300–2000 mg/kg | (61) |
| MCPA | dialkanoyloxyethyl-dimethylammonium | acute oral toxicity LD50 for rats, >2000 mg/kg; acute toxicity 96 h LD50 for rainbow trout, 7–17 mg/L; acute toxicity 72 h ErC50 for green algae, 1.6–1.9 mg/L; immobilization 48 h EC50 of water flea, 0.2–0.5 mg/L | (63) |
| MCPA | quaternized DABCO | S. aureus MIC (2–138 μM), MBC (2–138 μM); S. epidermidis MIC (<1–138 μM), MBC (<1–138 μM); B. subtilis MIC (4–138 μM), MBC (4–138 μM); E. faecalis MIC (7–1104 μM), MBC (7–1104 μM); M. luteus MIC (<1–18 μM), MBC (<1–35 μM); P. aeruginosa MIC (246–2207 μM), MBC (246 to >2207 μM); S. marcescens MIC (442 to >2207 μM), MBC (885 to >2207 μM); P. vulgaris MIC (28 to >2207 μM), MBC (28 to >2207 μM) M. catarrhalis MIC (<1–138 μM), MBC (<1–138 μM); E. coli MIC (30–2207 μM), MBC (30 to >2207 μM); Rh. rubra MIC (4–1104 μM), MFC (4–2207 μM); C. albicans MIC (4–2207 μM), MFC (4–2207 μM) | (37) |
| MCPA | bis(ammonium) derivatives of tebuconazole | fungicidal activity at 10 ppm, S. sclerotiorum 28.3–38.4%, B. cinerea 39.5–81.5%, F. culmorum 60.5–81.5%, F. oxysporum 50.0–63.8%, Colletotrichum sp. 48.2–62.0%, M. nivale, 11.2–52.9%; fungicidal activity at 100 ppm, S. sclerotiorum 98.2–100.0%, B. cinerea 100.0%, F. culmorum 90.6–100.0%, F. oxysporum 97.8–100.0%, Colletotrichum sp. 95.7%, M. nivale 52.5–68.5%; fungicidal activity at 1000 ppm, S. sclerotiorum 99.3–100.0%, B. cinerea 100.0%, F. culmorum 98.6–100.0%, F. oxysporum 100.0%, Colletotrichum sp. 100.0%, M. nivale 91.3–93.8% | (68) |
| 2,4-D | tebuconazole | at 10 ppm, fungistatic activity against F. culmorum and M. nivale; no damage toward winter wheat (170 g of AI/ha) | (40) |
| 2,4-D | propiconazole | at 10 ppm, strong inhibition of F. culmorum, M. nivale, B. cinerea and S. sclerotiorum mycelia growth; no damage toward winter wheat (AI 170 g/ha) | (40) |
| 2,4-D | tetraalkylammonium | AI 450 g/ha, winter wheat, 4.98–10.50 t/ha (untreated control, 4.84–9.32 t/ha); AI 1200 g/ha, winter wheat, 3.45–7.63 t/ha (untreated control, 3.67–6.83 t/ha); crop injury, 16–38% | (52) |
| 2,4-D | alkylbis(n-ethoxylated)-methylammonium | AI 450 g/ha: winter wheat, 5.78–10.26 t/ha (untreated control, 4.84–9.32 t/ha); AI 1200 g/ha: winter wheat, 3.41–7.86 t/ha (untreated control, 3.67–6.83 t/ha); crop injury, 13–21% | (52) |
| 2,4-D | betainium | acute oral LD50 for rats, 300–2000 mg/kg | (61) |
| 2,4-D | 4,4-dialkylmorpholinium | EC50 of microbiota isolated from different environmental niches: river sludge, 104–148 mg/L, garden soil, 113–184 mg/L, agricultural runoff stream, 195–227 mg/L, agricultural soil, 211–260 mg/L, waste repository, 222–277 mg/L | (73) |
| MCPP | tebuconazole | at 10 ppm, fungistatic activity against F. culmorum and M. nivale; no damage toward winter wheat (AI 170 g/ha) | (40) |
| MCPP | propiconazole | at 10 ppm, inhibition of F. culmorum, M. nivale, B. cinerea, and S. sclerotiorum mycelia growth; no damage toward winter wheat (AI 170 g/ha) | (40) |
| MCPP | tetraalkylammonium | EC50 for P. putida, 0.3–8.0 mM; cis–trans 50%,b 0.1–11.0 mM | (51) |
| MCPP | derivatives of phenoxy-2-acetoxyethyldecyl-dimethylammonium | enzymatic activity (GST, SOD, APX, CAT) and quantitative analysis of nonenzymatic factors (GSH and chlorophyll a and b), mutagenic activity of S. typhimurium | (21) |
| dicamba | tebuconazole | at 10 ppm, fungistatic activity against F. culmorum and M. nivale; no damage toward winter wheat (AI 170 g/ha) | (40) |
| dicamba | propiconazole | at 10 ppm, strong inhibition of F. culmorum, M. nivale, B. cinerea, and S. sclerotiorum mycelia growth; no damage toward winter wheat (AI 170 g/ha) | (40) |
| dicamba | tetraalkylammonium | EC50 for P. putida, 0.1–9.8 mM; cis–trans 50%,b 0.1–15.2 mM | (51) |
| dicamba | 4,4-dialkylmorpholinium | EC50 of microbiota isolated from different environmental niches: river sludge, >500 mg/L; garden soil, >500 mg/L; agricultural runoff stream, >500 mg/L; agricultural soil, >500 mg/L; waste repository, >500 mg/L | (73) |
| dicamba | bis(ammonium) derivatives of tebuconazole | fungicidal activity at 10 ppm, S. sclerotiorum 90.9–98.6%, B. cinerea 31.5–50.4%, F. culmorum 58.7–72.5%, F. oxysporum 59.1–67.4%, Colletotrichum sp. 54.7–63.0%, M. nivale 0.0–46.7%, | (68) |
| fungicidal activity at 100 ppm, S. sclerotiorum 97.8–100.0%, B. cinerea 100.0%, F. culmorum 93.8–100.0%, F. oxysporum 97.8–100.0%, Colletotrichum sp. 95.7–97.8%, M. nivale 63.8–92.0% | |||
| fungicidal activity at 1000 ppm, S. sclerotiorum 98.6–100.0%, B. cinerea 100.0%, F. culmorum 100.0%, F. oxysporum 100.0%, Colletotrichum sp. 100.0%, M. nivale 92.0–95.7% | |||
| clopyralid | derivatives of phenoxy-2-acetoxyethyldecyl-dimethylammonium | enzymatic activity (GST, SOD, APX, CAT) and quantitative analysis of nonenzymatic factors (GSH and chlorophyll a and b), mutagenic activity of S. typhimurium | (21) |
| pelargonate | tetraalkylammonium | S. aureus MIC <0.02–2.0 mM, MBC <0.04–7.8 mM; E. coli MIC 0.1–5.6 mM, MBC <0.04 to >5.6 mM; P. aeruginosa MIC 0.6–5.0 mM, MBC 1.2–7.8 mM; C. albicans MIC <0.04–3.2 mM, MFC <0.04 to >3.2 mM; acute oral toxicity LD50 for rats, 300 to >2000 mg/kg; acute toxicity toward rainbow trout (96 h) LC0 7.27 mg/L, LC50 10.58 mg/L, LC100 16 mg/L; growth inhibition of green algae (72 h) EyC10 0.02 mg/L, EyC20, 0.03 mg/L, EyC50, 0.06 mg/L; immobilization of water flea (48 h) EC0 0.125 mg/L, EC50 0.284 mg/L, EC100 0.5 mg/L | (33) |
| pelargonate | alkylbis(n-ethoxylated) methylammonium | S. aureus MIC <0.03 mM, MBC <0.03 mM; E. coli MIC 1.1 mM, MBC 4.3 mM; P. aeruginosa MIC >4.3 mM, MBC >4.3 mM; C. albicans MIC <0.03 mM, MFC <0.03 mM; acute oral toxicity LD50 for rats, 300–2000 mg/kg | (33) |
| pelargonate | N-alkylbetainium | S. aureus MIC 0.3 mM, MBC 2.6 mM; E. coli MIC 1.3 mM, MBC >5.2 mM; P. aeruginosa MIC 5.2 mM, MBC >5.2 mM; C. albicans MIC 0.6 mM, MFC 0.6 mM | (33) |
| pelargonate | dialkanoyloxyethyl-dimethylammonium | S. aureus MIC 2.8 mM, MBC >2.8 mM; E. coli MIC >2.8 mM, MBC >2.8 mM; P. aeruginosa MIC >2.8 mM, MBC >2.8 mM; C. albicans MIC >2.8 mM; MFC >2.8 mM | (33) |
| pelargonate | quaternized DABCO | feeding-deterrent activity (Tdc): adults granary weevil Td = 110.2–190.0; adults confused flour beetle Td = −19.3–98.4; larvae khapra beetle Td = 44.5–175.2; larvae confused flour beetle Td = −11.0–110.5 | (34) |
| MCPA/dicamba (oligomeric) | alkylbis(n-ethoxylated) methylammonium | next generation sequencing, no significant changes in soil microbial diversity | (43) |
a
Table does not include salts with melting points greater than 100 °C. AI, active ingredient; LD50, concentration resulting in 50% lethality; ErC50, concentration resulting in 50% reduction in growth; EC50, half maximal effective concentration; MIC, minimum inhibitory concentration; MBC, minimum bactericidal concentration; MFC, minimum fungicidal concentration; EyCx, concentration resulting in x% reduction in yield. S. aureus, Staphylococcus aureus; S. epidermidis, Staphylococcus epidermidis; B. subtilis, Bacillus subtilis; E. faecalis, Enterococcus faecalis; M. luteus, Micrococcus luteus; P. aeruginosa, Pseudomonas aeruginosa; S. marcescens, Serratia marcescens; P. vulgaris, Proteus vulgaris; M. catarrhalis, Moraxella catarrhalis; E. coli, Escherichia coli; Rh. rubra, Rhodotorula rubra; C. albicans, Candida albicans; S. sclerotiorum, Sclerotinia sclerotiorum, B. cinerea, Botrytis cinerea; F. culmorum, Fusarium culmorum; M. nivale, Microdochium nivale; F. oxysporum, Fusarium oxysporum; P. putida, Pseudomonas putida; S. typhimurium, Salmonella typhimurium.
b
cis/trans 50%, concentration that caused an increase in the trans/cis ratio of unsaturated fatty acids to 50% of the maximum trans/cis level reached at saturating concentrations of the toxicant.
c
Td, the total coefficient of deterrence (151–200, very good deterrents; 101–150, good deterrents; 51–100, medium deterrents; <50, weak deterrents; negative values, attractants).