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Common name cyfluthrin (BSI, draft E-ISO, BAN); cyfluthrine ((f) draft F-ISO)
IUPAC name (RS)-a-cyano-4-fluoro-3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Roth: (RS)-a-cyano-4-fluoro-3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Chemical Abstracts name cyano(4-fluoro-3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (unstated stereochemistry)
CAS RN [68359-37-5] unstated stereochemistry
PHYSICAL CHEMISTRY
Composition Comprises a mixture of four diastereoisomeric pairs of enantiomers:
I (R)-a-cyano-4-fluoro-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate + (S)-a, (1S)-cis-;
II (S)-a, (1R)-cis- + (R)-a, (1S)-cis-;
III (R)-a, (1R)-trans- + (S)-a, (1S)-trans-;
IV (S)-a, (1R)-trans- + (R)-a, (1S)-trans- .
Tech. grade contains: 23-27% diastereoisomer I, 17-21% diastereoisomer II, 32-36% diastereoisomer III, and 21-25% diastereoisomer IV. Mol. wt. 434.3 M.f. C22H18Cl2FNO3 Form Colourless crystals; (tech. is a brown, oily, viscous mass, with crystalline parts). M.p. (I) 64 ºC; (II) 81 ºC; (III) 65 ºC; (IV) 106 ºC; tech., c. 60 ºC V.p. (I) 9.6 ´ 10-4; (II) 1.4 ´ 10-5; (III) 2.1 ´ 10-5; (IV) 8.5 ´ 10-5 (all in mPa, 20 ºC) KOW logP: (I) 6.0; (II) 5.9; (III) 6.0; (IV) 5.9 (all 20 °C) Henry (I) 1.9 ´ 10-1; (II) 2.9 ´ 10-3; (III) 4.2 ´ 10-3; (IV) 1.3 ´ 10-2 (all in Pa m3 mol-1, 20 °C) S.g./density 1.28 (20 ºC) Solubility Diastereoisomer I: In water 2.5 (pH 3), 2.2 (pH 7) (both in mg/l, 20 ºC). In dichloromethane, toluene >200, n-hexane 10-20, isopropanol 20-50 (all in g/l, 20 ºC). Diastereoisomer II: In water 2.1 (pH 3), 1.9 (pH 7) (both in mg/l, 20 ºC). In dichloromethane, toluene >200, n-hexane 10-20, isopropanol 5-10 (all in g/l, 20 ºC). Diastereoisomer III: In water 3.2 (pH 3), 2.2 (pH 7) (both in mg/l, 20 ºC). In dichloromethane, toluene >200, n-hexane, isopropanol 10-20 (all in g/l, 20 ºC). Diastereoisomer IV: In water 4.3 (pH 3), 2.9 (pH 7) (both in mg/l, 20 ºC). In dichloromethane >200, toluene 100-200, n-hexane 1-2, isopropanol 2-5 (all in g/l, 20 ºC). Stability Thermally stable at room temperature. In water, DT50 for diastereoisomer I: 36, 17, 7; II 117, 20, 6; III 30, 11, 3; IV 25, 11, 5 (all in days, pH 4, 7, 9 respectively, 22 ºC). F.p. 107 ºC (tech.)
APPLICATIONS
Mode of action Non-systemic insecticide with contact and stomach action. Acts on the nervous system, with rapid knockdown and long residual activity.
Uses An insecticide effective against many pests, especially Lepidoptera, Coleoptera, Homoptera and Hemiptera on cereals, cotton, fruit and vegetables; also against migratory locusts and grasshoppers. For agricultural uses, applied at 15-40 g/ha. Used against Blattellidae, Culicidae and Muscidae in public health situations, stored products, domestic use and animal health. It has a rapid knockdown effect and long-lasting residual activity.