Nomenclature
CAS number: 68359-37-5
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic
acid cyano(4-fluoro-3-phenoxyphenyl)methyl ester;
(R,S)-α-cyano-4-fluoro-3-phenoxybenzyl-
(1R,S)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate; cyfoxylate; FCR-1272; BAY FCR 1272; Baythroid (Bayer CropSci.); Renounce (Bayer CropSci.); Tempo (Bayer).
C
22H
18Cl
2FNO
3; mol wt 434.29.
C 60.84%, H 4.18%, Cl 16.33%, F 4.37%, N 3.23%, O 11.05%.
Description and 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).Derivative
(1R,3R,αR)-Form.
Nomenclature
CAS number: 85649-12-3
Properties
Colorless oil. [α]D20 -15.0° (c = 1.0 in CHCl3).Derivative
(1R,3R,αS)-Form.
Nomenclature
CAS number: 85649-15-6
Properties
Crystals, mp 50-52°. [α]D20 +24.5° (c = 1.0 in CHCl3).Derivative
(1R,3S,αS)-Form.
Nomenclature
CAS number: 85649-19-0
Properties
Crystals from m-hexane mp 68-69°. [α]D20 -2.1° (c = 1.0
in CHCl3).Use
Agricultural insecticide.