Fipronil

TC & FORMULATION: 95%TC, 50G/L SC, 200G/L SC

Structure Formula:  

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] 

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.  

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