Title: Cyfluthrin
CAS Registry Number: 68359-37-5
CAS Name: 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid cyano(4-fluoro-3-phenoxyphenyl)methyl ester
Additional Names: (R,S)-a-cyano-4-fluoro-3-phenoxybenzyl-(1R,S)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate; cyfoxylate
Manufacturers' Codes: FCR-1272; BAY FCR 1272
Trademarks: Baythroid (Bayer CropSci.); Renounce (Bayer CropSci.); Tempo (Bayer)
Molecular Formula: C22H18Cl2FNO3
Molecular Weight: 434.29
Percent Composition: C 60.84%, H 4.18%, Cl 16.33%, F 4.37%, N 3.23%, O 11.05%
Literature References: Synthetic pyrethroid insecticide. Commercial product is mixture of 8 isomers, the (1R)-isomers primarily responsible for the bioactivity. Prepn of racemic mixture: R. Fuchs et al., DE 2709264; eidem, US 4218469 (1978, 1980 both to Bayer AG). Prepn of stereoisomers: eidem, EP 22970; eidem, US 4287208 (both 1981 to Bayer AG). Chiral phase HPLC separation of enantiomers: R. A. Chapman, J. Chromatogr. 258, 175 (1983). Metabolism by cell suspension cultures: U. Preiss et al., Chemosphere 13, 861 (1984). Field evaluation against cotton insect pests: J. A. Durant, J. Agric. Entomol. 1, 201 (1984). Review of chemistry, bioactivity and field studies: I. Hammann, R. Fuchs, Pflanzenschutz-Nachr. 34, 121-151 (1981); of formulations and potential uses: W. Behrenz et al., ibid. 36, 127-176 (1983). Review of toxicology and human exposure: Toxicological Profile for Pyrethrins and Pyrethroids (PB2004-100004, 2003) 332 pp.
Properties: Yellowish-brown oil, nD23 1.5511. Soly in water (20°): 1-2 ´ 10-6 g/l. LD50 in male, female rats, male, female mice (mg/kg): 500-800, 1200, 300, 600 orally in Lutrol (Behrenz). LC50 (96 hr) in rainbow trout: 0.0006 mg/l (Hammann).
Index of refraction: nD23 1.5511
Toxicity data: LD50 in male, female rats, male, female mice (mg/kg): 500-800, 1200, 300, 600 orally in Lutrol (Behrenz); LC50 (96 hr) in rainbow trout: 0.0006 mg/l (Hammann)
Derivative Type: (1R,3R,aR)-Form
CAS Registry Number: 85649-12-3
Properties: Colorless oil. [a]D20 -15.0° (c = 1.0 in CHCl3).
Optical Rotation: [a]D20 -15.0° (c = 1.0 in CHCl3)
Derivative Type: (1R,3R,aS)-Form
CAS Registry Number: 85649-15-6
Properties: Crystals, mp 50-52°. [a]D20 +24.5° (c = 1.0 in CHCl3).
Melting point: mp 50-52°
Optical Rotation: [a]D20 +24.5° (c = 1.0 in CHCl3)
Derivative Type: (1R,3S,aS)-Form
CAS Registry Number: 85649-19-0
Properties: Crystals from m-hexane mp 68-69°. [a]D20 -2.1° (c = 1.0 in CHCl3).
Melting point: mp 68-69°
Optical Rotation: [a]D20 -2.1° (c = 1.0 in CHCl3)
Use: Agricultural insecticide. |