Products
FIPRONIL
Insecticide
phenylpyrazole insecticide
NOMENCLATURE
Common name fipronil (BSI, pa E-ISO)
IUPAC name (-5-amino-1-(2,6-dichloro-a,a,a-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] Development codes MB
46030; RPA-030 (both Rhône-Poulenc)
PHYSICAL CHEMISTRY
Mol. wt. 437.2 M.f. C12H4Cl2F6N4OS Form White
solid. M.p. 200-201 ºC; (tech., 195.5-203 °C) V.p.
3.7 × 10-4 mPa (25 ºC) KOW logP = 4.0 (shake flask
method) Henry 3.7 × 10-5 Pa m3 mol-1 (calc.) S.g./density 1.477-1.626
(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).
APPLICATIONS
Biochemistry Insecticide which acts as a potent 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. Moderately systemic and, in some 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 rootworm, wireworms and termites by soil treatment
in maize. Control of boll weevil and plant bugs on cotton, diamond-back moth
on crucifers, Colorado potato beetle on potatoes by foliar application. Control
of stem borers, leaf miners, planthoppers, leaf folder/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.