Table 1.
New metabolites of neonicotinoids and fipronil in addition to those reported by Simon-Delso et al. (2015)
| Parent compound | Metabolites | Formation medium | References |
|---|---|---|---|
| Imidacloprid | Carbonyl derivative, N-{1-[(6-chloropyridin-3-yl)methyl]-(4 or 5)-oxoimidazolidin-2-ylidene}nitramide | D. melanogaster | Hoi et al. (2014) |
| Hydroxy desnitro imidacloprid, (1 or 3)-[(6-chloropyridin-3-yl)methyl]-2-iminoimidazolidin-4-ol | D. melanogaster | Hoi et al. (2014) | |
| Nitenpyram | Deg_01, N-[(6-chloropyridin-3-yl)methyl]ethanamine | Drinking water | Noestheden et al. (2016) |
| Deg_03, N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-N′-methylmethanimidamide | Drinking water | Noestheden et al. (2016) | |
| Deg_04, N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-N′-methylurea | Drinking water | Noestheden et al. (2016) | |
| Deg_14, (E)-N1-[((4 or 5),6-dichloropyridin-3-yl)methyl]-N1-ethyl-N′1-methyl-2-nitroethene-1,1-diamine | Drinking water | Noestheden et al. (2016) | |
| Deg_16, (E)-N′1-[(2-chloropyridin-4-yl)methyl]-N1-[(6-chloropyridin-3-yl)methyl]-N1-ethyl-2-nitroethene-1,1-diamine | Drinking water | Noestheden et al. (2016) | |
| Deg_18, (1E)-N′1-[(2-chloropyridin-4-yl)methyl]-N1-[(6-chloropyridin-3-yl)methyl]-N1-ethyl-2-nitrobut-1-ene-1,1-diamine | Drinking water | Noestheden et al. (2016) | |
| Fipronil | M7, 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-imino-4-oxo-4,5-dihydro-1H-pyrazole-3-carbonitrile | Rat urine | McMahen et al. (2015) |
| M4, 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-nitroso-1H-pyrazol-4-ol | Rat urine | McMahen et al. (2015) | |
| Hydroxylated fipronil sulfone, 5-amino-1-[2,6-dichloro-3-hydroxy-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfonyl]-1H–pyrazole-3-carbonitrile | Fungal degradation (batch reactor) | Wolfand et al. (2016) | |
| Glycosylated fipronil sulfone, 5-amino-1-[2,6-dichloro-3-{[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy}-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfonyl]-1H–pyrazole-3-carbonitrile | Fungal degradation (batch reactor) | Wolfand et al. (2016) | |
| TP3, {(E)-[2,6-dichloro-4-(trifluoromethyl)phenyl]diazenyl}acetonitrile | Photocatalytic degradation in water | Gomes Júnior et al. (2017) | |
| TP4, 5-amino-4-[(trifluoromethyl)sulfonyl]-1H–pyrazole-3-carbonitrile | Photocatalytic degradation in water | Gomes Júnior et al. (2017) | |
| Cycloxaprid | TP1, 9-nitro-1-[(pyridin-3-yl)methyl]-2,3,5,6-tetrahydro-1H-imidazo[1,2-a]azepine-(2 or 3),5-diol | Soil | Liu et al. (2015) |
| TP2, 2,3-dihydroxy-9-nitro-2,3,6,7-tetrahydro-1H-imidazo[1,2-a]azepine-5,8-dione | Soil | Liu et al. (2015) | |
| TP3, 2,3,9-trihydroxyhexahydro-1H-imidazo[1,2-a]azepine-5,8-dione | Soil | Liu et al. (2015) | |
| TP4, 1-{1-[(6-chloropyridin-3-yl)methyl]-(4 or 5)-hydroxyimidazolidin-2-yl}-3-hydroxypropan-1-one | Soil | Liu et al. (2015) | |
| TP5, 1-[(6-chloropyridin-3-yl)methyl]imidazolidine-2-carbaldehyde | Soil | Liu et al. (2015) | |
| TP6, 1-[(6-chloropyridin-3-yl)methyl]-(4 or 5)-hydroxyimidazolidine-2-carboxylic acid | Soil | Liu et al. (2015) | |
| TP7, 2-chloro-8-hydroxy-7,8-dihydro-1,6-naphthyridine-6(5H)-carbaldehyde | Soil | Liu et al. (2015) | |
| TP8, (2Z)-2-(3-hydroxy-1-nitrosopropylidene)-(1 or 3)-[(pyridin-3-yl)methyl]imidazolidin-4-ol | Soil | Liu et al. (2015) | |
| TP9, (2Z)-2-(2-hydroxy-1-nitrosoethylidene)-(1 or 3)-[(pyridin-3-yl)methyl]imidazolidin-4-ol | Soil | Liu et al. (2015) | |
| TP10, (2Z)-2-(2-hydroxy-1-nitrosoethylidene)-1-[(pyridin-3-yl)methyl]imidazolidine-4,5-diol | Soil | Liu et al. (2015) | |
| TP11, 1-[(pyridin-3-yl)methyl]imidazolidine-4,5-diol | Soil | Liu et al. (2015) | |
| M1, (1-(6-chloronicotinyl)-2- nitromethylene-imidazolidine), (nitromethylene)imidazole, (2Z)-1-[(6-chloropyridin-3-yl)methyl]-2-(nitromethylidene)imidazolidin-4-ol | Aerobic soil | Chen et al. (2017) | |
| M2, 1-[(6-chloropyridin-3-yl)methyl]-4-hydroxy-4,5-dihydro-1H-imidazole-2-carboxylic acid | Aerobic soil | Chen et al. (2017) | |
| M3, 1-[(6-chloropyridin-3-yl)methyl]imidazolidine-2,4-diol | Aerobic soil | Chen et al. (2017) | |
| Imidaclothiz | Olefin imidaclothiz, N-{1-[(2-chloro-1,3-thiazol-5-yl)methyl]-1,3-dihydro-2H-imidazol-2-ylidene}nitramide | Soil (microbial) | Liu et al. (2011) |
| Nitroso imidaclothiz, N-{1-[(2-chloro-1,3-thiazol-5-yl)methyl]imidazolidin-2-ylidene}nitrous amide | Soil (microbial) | Liu et al. (2011) | |
| Guanidine imidaclothiz, seco imidaclothiz, N-[(2-chloro-1,3-thiazol-5-yl)methyl]-N″-nitroguanidine | Soil (microbial) | Liu et al. (2011) | |
| Paichongding | 1-((6-Chloropydidin-3-yl)methyl)-7-methyl-8-nitro-5-hydroxy-1,2,3,5,6,7-hexahydroimidazo[1,2-α]pyridine | Soil (microbial) | Cai et al. (2015a, b) |
| 1-((6-Chloropydidin-3-yl)methyl)-7-methyl-8-hydroxy-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-α]pyridine | Soil (microbial) | Cai et al. (2015b) | |
| 1-((6-Chloropydidin-3-yl)methyl)-7-methyl-5-carbonyl-1,2,3,5,6,7-hexahydroimidazo[1,2-α]pyridine | Soil (microbial) | Cai et al. (2015b) | |
| 1-((6-Chloropydidin-3-yl)methyl)-7-methyl-8-amino-1,2,3,5,6,7-hexahydroimidazo[1,2-α]pyridine | Soil (microbial) | Cai et al. (2015b) | |
| 8-Amino-1,2,3,5,6,7-hexahydroimidazo[1,2-α]pyridine | Soil (microbial) | Cai et al. (2015b) | |
| M5, 1-(6-chloropyridin-3-ylmethyl)-7-methyl-8-nitroso-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-α]pyridine | Soil (microbial) | Cai et al. (2015a) | |
| Flooded paddy soil | Li et al. (2016a) | ||
| 1-(6-Chloropyridin-3-ylmethyl)-7-methyl-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-α]pyridine | Soil (microbial) | Cai et al. (2015a) | |
| 1-((6-Chloropyridin-3-yl)methyl)-5,7-diol-8-amino-1,2,3,5,6,7-hexahydroimidazo[1,2-α]pyridine | Soil (microbial) | Cai et al. (2015a) | |
| 1-((6-Chloropyridin-3-yl)methyl)-5,7-diol-8-amino-octahydroimidazo[1,2-α]pyridine | Soil (microbial) | Cai et al. (2015a) | |
| I4, 1-((6-chloropyridin-3-yl)methyl)-2,3-dihydro-5-one-7-methylimidazo[1,2-α]pyridine | Soil (microbial) | Cai et al. (2015a) | |
| Biodegradation in water in dark conditions | Wang et al. (2016) | ||
| I1, M1, 1-(6-chloropyridin-3-ylmethyl)-7-methyl-8-nitro-1,2,3,5,6,7- hexahydroimidazo[1,2-α]pyridin-5-ol | Biodegradation in water in dark conditions | Wang et al. (2016) | |
| Flooded paddy soil | Li et al. (2016a) | ||
| I2, 8-amino-1-(6-chloropyridin-3-ylmethyl)-octahydroimidazo[1,2-α]pyridine-5,7-diol | Biodegradation in water in dark conditions | Wang et al. (2016) | |
| I3, 8-amino-1-(6-chloropyridin-3-ylmethyl)octahydroimidazo[1,2-α]pyridin-7-ol | Biodegradation in water in dark conditions | Wang et al. (2016) | |
| I5, octahydroimidazo[1,2-α]pyridin-8-ylamine | Biodegradation in water in dark conditions | Wang et al. (2016) | |
| I6, 8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-α]pyridine | Biodegradation in water in dark conditions | Wang et al. (2016) | |
| M2, 1-((6-chloropyridin-3-yl)methyl)-7-methyl-5-propoxyoctahydroimidazo[1,2-α] pyridine | Flooded paddy soil | Li et al. (2016a) | |
| M3, 1-(6-chloropyridin-3-ylmethyl)-6,7-methyl-8-nitro-1,2,3,5,6,7- hexahydroimidazo[1,2-α]pyridin-5-ol | Flooded paddy soil | Li et al. (2016a) | |
| M4, 5-hydroxy-7-methyl-1-(pyridin-3-ylmethyl)hexahydroimidazo[1,2-α]pyridin-8(5H)-one | Flooded paddy soil | Li et al. (2016a) | |
| M6, 1-((6-chloropyridin-3-yl)methyl)-2,3-hydroxy-7-methyl-8-nitro-2,3,6,7-tetrahydroimidazo[1,2-α]pyridin-5(1H)-one | Flooded paddy soil | Li et al. (2016a) | |
| M7, 1-(6-chloropyridin-3-ylmethyl)-7-methyl-2,3,6,7-tetrahydroimidazo[1,2-α] pyridin-5(1H)-one | Flooded paddy soil | Li et al. (2016a) | |
| M8, 1-(6-chloropyridin-3-ylmethyl)-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-α]pyridin-2,3-ol | Flooded paddy soil | Li et al. (2016a) | |
| M9, 1-(6-chloropyridin-3-ylmethyl)-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7- hexahydroimidazo[1,2-α]pyridin-6-ol | Flooded paddy soil | Li et al. (2016a) | |
| Sulfoxaflor | X11721061, 1-[6-(trifluoromethyl)pyridin-3-yl]ethan-1-ol | Rice fields and straws | Chung et al. (2017) |
| Plants and animals | Pfeil et al. (2011) | ||
| X117119474, N-[methyl(oxo){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ4-sulfanylidene]urea | Rice fields and straws | Chung et al. (2017) | |
| Soil and plants | Pfeil et al. (2011) | ||
| X11596066, 5-ethyl-2-trifluoromethylpyridine | Animals | Pfeil et al. (2011) | |
| X11579457, 5-[1-(S-methylsulfonimidoyl)ethyl]-2-(trifluoromethyl)pyridine | Soil | Pfeil et al. (2011) | |
| X11519540, 5-[(1-methylsulfonyl)ethyl]-2-(trifluoromethyl)pyridine | Soil and animals | Pfeil et al. (2011) | |
| Flupyradifurone | Difluoroacetic acid (DFA) | Soil, water, plants and animals | O’Mullane et al. (2015) |
| Flupyradifurone-OH, 4-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}-5-hydroxyfuran-2(5H)-one | Animals | O’Mullane et al. (2015) | |
| Flupyradifurone-OH-SA, 3-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}-5-oxo-2,5-dihydrofuran-2-yl hydrogen sulfate | Animals | O’Mullane et al. (2015) | |
| Hippuric acid, [(6-chloropyridine-3-carbonyl)amino]acetic acid | Animals | O’Mullane et al. (2015) | |
| Flupyradifurone-des-difluoroethyl, 4-{[(6-chloropyridin-3-yl)methyl]amino}furan-2(5H)-one | Animals | O’Mullane et al. (2015) | |
| Difluoroethyl-amino-furanone, 4-[(2,2-difluoroethyl)amino]furan-2(5H)-one | Plants and animals | Li et al. (2016b) | |
| O’Mullane et al. (2015) | |||
| (6-Chloro-3-pyridyl)methanol* | Plants | O’Mullane et al. (2015) | |
| 6-Chloronicotinic acid* | Plants | Li et al. (2016b) | |
| O’Mullane et al. (2015) | |||
| Amino-furanone, 4-aminofuran-2(5H)-one | Plants | O’Mullane et al. (2015) | |
| Flupyradifurone-acetic acid, {[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}acetic acid | Plants | O’Mullane et al. (2015) |
*Metabolite common to other neonicotinoids