Table 3.
First-generation metabolites of fipronil in various media and organisms. Metabolites known to be active toward invertebrates or mammals are highlighted in bold
| Parent compound | Metabolites | Formation medium | Reference |
|---|---|---|---|
| Fipronil | Fipronil detrifluoromethylsulphinyl, 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl) pyrazole, MB 45897 | Mammals, soil, plants (photolysis) | FAO fipronil, (Hainzl and Casida 1996); (France 2005) |
| Fipronil-sulfide, 5-amino-1-.[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)thio]-1H-pyrazole-3-carbonitrile, MB45950 | Mammals, soil, plants, water (photolysis) | FAO fipronil; (Bobé et al. 1998); (Aajoud et al. 2003); (France 2005); (Gunasekara et al. 2007) | |
|
Fipronil-sulfone, 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfonyl]-1H-pyrazole-3-carbonitrile, MB 46136 |
Mammals (milk), hens (eggs), soil, plants, water (incl. photolysis) | (Hainzl and Casida 1996); (Hainzl et al. 1998); (Bobé et al. 1998); FAO fipronil, (Tingle et al. 2003); (Aajoud et al. 2003); (France 2005) | |
| Fipronil-desulfinyl, desthiofipronil, 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(1R,S)-(trifluoromethyl)]-1H-pyrazole-3-carbonitrile, MB 46513 | Soil, plants, water (photolysis) | (Hainzl and Casida 1996); (Hainzl et al. 1998); (Bobé et al. 1998); FAO fipronil; (Tingle et al. 2003); (Aajoud et al. 2003); (Gunasekara et al. 2007) | |
| 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole-4-sulfonic acid, RPA104615 | Soil, water (photolysis) | (Tingle et al. 2003); FAO fipronil | |
| 5-amino-3-carbamyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonylpyrazole, RPA105320 | Soil, plants | FAO fipronil | |
| Fipronil-amide, 5-amino-3-carbamyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole, RPA 200766 | Mammals, soil, plants, water (hydrolysis) | (Bobé et al. 1998); (Tingle et al. 2003); (Aajoud et al. 2003); FAO fipronil | |
|
5-amino-3-carbamyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole-3-carboxylic acid, RPA 200761 |
Mammals, soil, plants, water | FAO fipronil; (France 2005) | |
| Various conjugates in urine and bile (RPA 105048, UMET/10, UMET/3, FMET/9, UMET/4, FMET/7, FMET/10, UMET/15) | Mammals | FAO fipronil; (France 2005) | |
| MB 46400 | Mammals, hens (eggs) | FAO fipronil; (France 2005) | |
| RPA 108058 | Mammals, hens (eggs) | FAO fipronil | |
| Ring-opened 106889 | Mammals, hens (eggs) | FAO fipronil | |
| RPA 106681 | Soil | FAO fipronil |