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IRAC 2B phenylpyrazole

Common name fipronil (BSI, E-ISO, (m) F-ISO) IUPAC name (±)-5-amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile
Chemical Abstracts name 5-amino-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(1R,S)-(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile CAS RN [120068–37–3] EC no. 424–610–5 Development codes MB 46030; RPA-030 (both Rhône-Poulenc); BAS 350 I (BASF) Smiles code Nc1c(S(=O)C(F)(F)F)c(C#N)nn1c2c(Cl)cc(cc2Cl)C(F)(F)F
Mol. wt. 437.2 M.f. C12H4Cl2F6N4OS Form White solid. M.p. 203 °C; (tech., 195.5–203 °C) V.p. 2 × 10-3 mPa (25 °C) Kow logP = 4.0 (shake flask method) Henry 2.31 × 10-4 Pa m3 mol-1 (calc.) S.g./density 1.477–1.705 (20 °C) Solubility In water 1.9 (pH 5), 2.4 (pH 9), 1.9 (distilled) (all in mg/l, 20 °C). In acetone 545.9, dichloromethane 22.3, hexane 0.028, toluene 3.0 (all in g/l, 20 °C). Stability Stable in water at pH 5 and 7; slowly hydrolysed at pH 9 (DT50 c. 28 d). Stable to heat. Slowly degrades in sunlight (c. 3% loss after 12 d continuous irradiation); rapidly photolysed in aqueous solution (DT50 c. 0.33 d).
History Discovered by Rhone-Poulenc in 1987. Reported by F. Colliot et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 1, 29). Introduced by Rhône-Poulenc Agrochimie (now Bayer AG) in 1993. Worldwide agricultural and environmental uses acquired by BASF AG (now BASF SE) in 2003. Manufacturers BASF; Anhui Huaxing; Fengle; Fertiagro; Iprochem; Yongan
Biochemistry Insecticide which acts as a blocker of the GABA-regulated chloride channel. Insects resistant or tolerant to pyrethroid, cyclodiene, organophosphorus and/or carbamate insecticides are susceptible to fipronil. Mode of action Broad-spectrum insecticide, toxic by contact and ingestion. Limited xylem systemicity in some monocotyledonous crops. Can be used to control insects when applied as a soil or seed treatment. Good to excellent residual control following foliar application. Uses Control of multiple species of thrips on a broad range of crops by foliar, soil or seed treatment. Control of corn rootworms, wireworms and termites by soil treatment in maize. Control of boll weevils and plant bugs on cotton, diamond-back moths on crucifers, and colorado beetle on potatoes, by foliar application. Control of stem borers, leaf miners, planthoppers, leaf folders/rollers and weevils in rice. Foliar application rates range from 10–80 g/ha; soil treatment rates 100–200 g/ha. Formulation types EC; FS; GR; SC; UL; WG.
Selected products ‘Fiprosun’ (Sundat) ; ‘Prince’ (BASF, Nissan) mixtures ‘Dr. Oryze-Prince’ (+ probenazole + probenazole + probenazole) (BASF, BASF, Hokko, Hokko, Meiji Seika, Meiji Seika) ; ‘Fuji-one Prince’ (+ isoprothiolane) (Nihon Nohyaku, Nihon Nohyaku) Other products ‘Adonis’ (Nufarm Ltd) ; ‘Agenda’ (BASF, Bayer Environmental Science) ; ‘Ascend’ (BASF) ; ‘Blitz’ (BASF) ; ‘Chipco Choice’ (BASF) ; ‘Cosmos’ (BASF) ; ‘Fipridor’ (Vapco) ; ‘Frontline’ (veterinary use) (Merial) ; ‘Gard’ (Nufarm Ltd) ; ‘Garnet’ (Vapco) ; ‘Goliath’ (BASF) ; ‘Icon’ (BASF) ; ‘Maxforce’ (various products, for ants and cockroaches) (Bayer Environmental Science) ; ‘Metis’ (BASF) ; ‘Regent’ (BASF, Nufarm Ltd) ; ‘Termidor’ (BASF) ; ‘Texas’ (BASF) ; ‘Top Choice’ (Bayer Environmental Science) ; ‘Vi-nil’ (Certis UK) ; ‘Violin’ (BASF) ; ‘Taurus’ (Makhteshim-Agan) ; ‘Goldor Bait’ (BASF) mixtures ‘Amistar-Prince’ (rice nursery box) (+ azoxystrobin + azoxystrobin + azoxystrobin) (Nihon Nohyaku, Nihon Nohyaku, Nissan, Nissan, Syngenta, Syngenta) ; ‘ArashiPrince’ (+ orysastrobin) (BASF, BASF) ; ‘Builder Prince’ (+ probenazole) (Hokko, Hokko) ; ‘Delaus-Prince’ (+ diclocymet) (Nissan, Nissan) ; ‘Gazette Prince’ (+ carbosulfan) (BASF, BASF) ; ‘Jumper’ (+ guazatine acetates + triticonazole) (BASF, BASF, BASF) ; ‘Pika Pika’ (+ pyroquilon + isoprothiolane) (Nihon Nohyaku, Nihon Nohyaku, Nihon Nohyaku) ; ‘V-Get Prince’ (+ tiadinil) (Nihon Nohyaku, Nihon Nohyaku) ; ‘Zoom’ (+ triticonazole + guazatine acetates) (BASF, BASF, BASF) ; ‘Standak Top’ (seed treatment) (+ thiophanate-methyl + pyraclostrobin) (BASF, BASF, BASF) Discontinued products ‘KB Guêpes *’ (BASF) mixtures ‘Cardinal *’ (+ aldicarb) (Bayer CropScience, Bayer CropScience) ; ‘Regent Plus *’ (+ aldicarb) (Bayer CropScience, Bayer CropScience) ; ‘Trident *’ (+ aldicarb) (Bayer CropScience, Bayer CropScience)
Product by rp hplc with uv detection (CIPAC Handbook, 2000, J, 60). Residues and metabolites in plants by gc/ECD (Resid. Anal. Methods). In soil by gc/ECD (Environ. Chem. Methods). In water by gc/ECD or lc/ms/ms (ibid.).
In plants, animals and the environment, fipronil is metabolised via reduction to the sulfide, oxidation to the sulfone, and hydrolysis to the amide. In the presence of sunlight, a photodegradate also forms via sulfoxide extrusion. The sulfide, sulfone and photodegradate are known to act at the GABA receptor site, whereas the amide does not. Animals In rats, once absorbed, the distribution and metabolism of fipronil is rapid. Elimination is mainly via the faeces as fipronil and its sulfone. The two major urinary metabolites were identified as conjugates of ring-opened pyrazole products. The distribution of radioactive residues in tissues was extensive after seven days. In goats and hens, the sulfone was the only metabolite identified in tissues. Plants When applied as an incorporated soil treatment to cotton, maize, sugar beet or sunflowers, uptake of fipronil into plants in all cases was low (c. 5%). At crop maturity, the major residue components observed in all plants were fipronil, the sulfone, and the amide. Following foliar application to cotton, cabbage, rice and potatoes, at crop maturity, fipronil and the photodegradate were the major residue components. Soil/Environment Results of lab. and field studies: Readily degraded; major degradates in soil (aerobic) are sulfone and amide, (anaerobic) are sulfide and amide. Photolysis of soil-applied fipronil gives the photodegradate together with sulfone and amide. Koc 427 (Speyer 2.2) to 1248 (sandy loam). Both fresh and aged column leaching studies (5 soils) indicate that fipronil and its metabolites present a low risk of downward movement in soil; this is supported by field dissipation studies. Following soil incorporated in-furrow granular applications, quantifiable residues were confined to the top 30 cm of soil, with no significant lateral movement or residues.
JMPR Mtg. 92 (2001); JMPR Evaln. I 93 (2001); JMPR Evaln. II 82 (1997), 91 (2000). ICSC 1503 (2004). EU Rev. Rep. SANCO/10033/2006; EFSA Sci. Rep. (2006) 65, 1–110. EU Status (1107/2009) Approved, 2007/52/EC.
Oral Acute oral LD50 for rats 92 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000, rabbits 354 mg/kg. Not a skin or eye irritant (OECD criteria). Not a skin sensitiser. Inhalation LC50 (4 h) for rats 0.39 mg/l (tech.; nose only exposure). NOEL (2 y) for rats 0.5 mg/kg diet (0.019 mg/kg b.w.); (18 mo) for mice 0.5 mg/kg diet; (52 w) for dogs 0.2 mg/kg b.w. daily (combined sexes). ADI (JMPR) 0.0002 mg/kg b.w. [2000], group ADI for fipronil and fipronil desulfinyl; (EFSA) 0.0002 mg/kg b.w. [2006]; (EPA) 0.0002 mg/kg b.w. [1994]. Other Non-mutagenic, non-teratogenic; no adverse effect on reproductive performance. Clinical signs of toxicity consistent with the interaction of the molecule at a neurotransmitter receptor were observed in all species tested, but were completely reversible. Toxicity class WHO (a.i.) II EPA (formulation) II EC classification T; R23/24/25, R48/25| N; R50, R53| (concn. dep.)
Birds Acute oral LD50 for bobwhite quail 11.3, mallard ducks >2000, pheasants 31, red-legged partridges 34, house sparrows 1120, pigeons >2000 mg/kg. Dietary LC50 (5 d) for bobwhite quail 49, mallard ducks >5000 mg/kg diet. Fish Acute LC50 (96 h) for bluegill sunfish 85, rainbow trout 248, European carp 430 μg/l. Daphnia LC50 (48 h) 0.19 mg/l; for D. carinata (48 h) 3.8 mg/l. Algae EC50 (96 h) for Scenedesmus subspicatus 0.068 mg/l; (120 h) for Selenastrum capricornutum >0.16, Anabaena flos-aquae >0.17 mg/l. Bees Highly toxic to honeybees, both by direct contact and by ingestion. However, no risk to bees when used as a soil or seed treatment. Worms Non-toxic.

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