Beta-cyfluthrin

TC & FORMULATION: 95%TC, 25G/L EC, 2.5% SC

Structure Formula:

NOMENCLATURE

Common name beta-cyfluthrin (BSI, draft E-ISO); beta-cyfluthrine ((f) draft F-ISO); cyfluthrin-beta (Canada)

IUPAC name (RS)-a-cyano-4-fluoro-3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 

Chemical Abstracts name cyano(4-fluoro-3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate 

CAS RN [68359-37-5] unstated stereochemistry  EEC no. 269-855-7 

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: <2% diastereoisomer I, 30-40% diastereoisomer II, <3% diastereoisomer III, and 53-67% diastereoisomer IV.  Mol. wt. 434.3  M.f. C22H18Cl2FNO3  Form Colourless crystals; (tech. is a white powder with slight characteristic smell).  M.p. (II) 81 ºC; (IV) 106 ºC  B.p. decomp. >210 °C  V.p. (II) 1.4 ´ 10-5 mPa; (IV) 8.5 ´ 10-5 mPa (both 20 ºC)  KOW (II) logP = 5.94; (IV) logP = 5.91  Henry (II) 2.9 ´ 10-3; (IV) 3.1 ´ 10-2 (both in Pa m3 mol-1, 20 °C)  S.g./density 1.34 g/cm3 (22 ºC)  Solubility In water: (II) 2.1, (IV) 1.2 (both in mg/l, 20 ºC). In dichloromethane and toluene, both pairs >200 g/l (20 ºC). (II) In hexane 2-5, isopropanol 5-10 (both in g/l, 20 ºC). (IV) in hexane 1-2, isopropanol 2-5 (both in g/l, 20 ºC).  Stability Thermally stable at room temperature. Hydrolysis DT50 (22 ºC) for (II): 117 d (pH 4), 20 d (pH 7), 6 d (pH 9); for (IV): 25 d (pH 4), 11 d (pH 7), 5 d (pH 9). 

APPLICATIONS

Biochemistry Acts on the nervous system of insects, disturbs the function of neurons by interaction with the sodium channel.  Mode of action Non-systemic insecticide with contact and stomach action. Acts on the nervous system, with rapid knockdown and long residual activity.  Uses Insecticide effective against Lepidoptera, Coleoptera, Hemiptera and Homoptera on cotton, fruit, vegetables, cereals and other crops, at 7.5-20 g/ha. Also against migratory locusts and grasshoppers; and in animal health. Formulation types EC; EW; GR; UL; SC.

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