New optically active insecticide - is (plus)-n-2,6-di:fluoro:benzoyl -N'-4-(1,1,2,3,3,3-hexafluoropropoxy) -2,5-di:chloro:phenyl-urea

摘要

The (+)-enantiomer of N-2,6-difluorobenzoyl-N'-(4-(1,1,2,3,3,3-hexafluoropropoxy) -2,5-dichlorophenyl urea of formula (I) and its salts are new. Intermediates of formula (II) and (IV) and (VII) are also new. USE/ADVANTAGE - (I) are used to combat insects of the order Lepidoptera, Coloeptera, Homoptera, Heteroptera, Diptera, Orthoptera, Siphonoptera, Isoptera and Hymemoptera. (I) are active against flies e.g. Musaia domestica and can also be used against plant-damaging insects in ornamental and commercial plants esp. in cotton (e.g. Spodoptera lithoralis and Heliothis virescens) as well as in fruit and vegetable plants (e.g. Laspeyresia pomonella, Leptinotarsa decemlineata and Epilachna varivestis). (I) have a marked activity against ovums and larvae of insects. (I) can also be used against ectoparasites such as Lucilia sericata in house and useful animals e.g. in stables and pastures. (I) have improved plant tolerance and low toxicity to warm blooded animals than known pest-control agents. In an example, to a soln. of 211mg (+)-4-(1,1, 2,3,3,3-hexafluoropropoxy)-2,5-dichloroaniline in 2 ml toluene was added dropwise a soln. of 117mg 2,6-difluorobenzoylisocyanate in 1.96 ml toluene. The mixt. was stirred for 10 hrs. at room temp.. The soln. was evapd. and the residue crystallised from hexane. The ppte. was sepd. and recrystallised from toluene to give 162 mg (I), m.pt. 166 deg.C.