Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1986-03-10
1988-06-28
Reamer, James H.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514640, 564256, 549442, A61K 3130
Patent
active
047539607
DESCRIPTION:
BRIEF SUMMARY
The invention relates to new 4-fluorophenoxy-benzyl ethers of oximes of substituted phenyl halomethyl ketones, to a process for their preparation and to their use as arthropodicides, especially as insecticides and acaricides.
Reference has been made in the literature to a general class of alkyl aryl ketone oxime ethers of the general structure ##STR2## wherein X is one or more substituents, Y is an alkyl group and R-OH is the alcohol component of active pyrethroid esters (Michael J. Bull et al., Pesticide Science, 1980, 11, 249-256). The same reference discloses specifically a limited group of compounds falling within the broad class in which X is 4-chloro, 4-fluoro or 4-methoxy, Y is methyl, ethyl, isopropyl, cyclopropyl or cyclobutyl and R is 3-phenoxybenzyl. Some of these compounds showed insecticidal activity. U.S. Pat. No. 4,079,149 discloses a group of compounds of the same class in which the substituent X is one or two halogen atoms or alkyl or alkoxy groups and Y is inter alia an alkyl group of two or more carbon atoms, optionally substituted with one or more halogen atoms and R is 3-phenoxybenzyl
U.K. Patent Application No. 2,025,407 discloses a similar group of compounds in which R is a 2,6-dihalobenzyl group. Neither of these references, however, discloses any specific compounds in which the group Y is a halogenated alkyl group.
The present invention provides new compounds of the general formula (I) ##STR3## wherein R represents F, Cl, Br, I, ethoxy, methoxy or propoxy and n is an integer between 1 and 5; or R represents 3,4-methylenedioxy; and R.sup.1 represents di- or trichloromethyl, fluorodichloromethyl or trifluoromethyl.
Preferred compounds are those where n=1 and R is in the 4-position on the phenyl ring.
The compounds for formula I can exist in two possible isomeric forms known as E and Z. Both isomeric forms are included in the invention.
The results of tests of insecticidal activity indicate that one isomeric form has significantly greater activity than the other.
The more active isomers of compounds of the formula (I) are distinguished by a powerful insecticidal and acaridical activity. In particular the compounds show powerful activity against cotton bud worm (Heliothis punctigera), an important agricultural pest.
The invention also provides methods for the production of the compounds of the formula I. One method, which is similar to that described in our copending Australian Patent Application No. 83103/82, involves reacting the appropriately substituted ketone or oxime of formula II ##STR4## wherein R, n and R.sup.1 are as defined above, and X is=O with O-(4-fluoro-3-phenoxybenzyl)-hydroxylamine hydrochloride.
This reacton is relatively slow but in some instances may be appreciably accelerated by using temperatures above room temperature. In general the reaction is conveniently carried out by stirring the reactants at the selected temperature and at atmospheric pressure.
Another method, in accordance with the invention, involves reacting the appropriately substituted oxime (formula II; X is =NOH) with 4-fluoro-3-phenoxybenzyl bromide.
The O-(4-fluoro-3-phenoxybenzyl)hydroxylamine hydrochloride can be synthesised from N-hydroxy-phthalimide, 4-fluoro-3-phenoxybenzyl bromide, n-butylamine and HC1 by the method of Kaztreiner, Szilagyi, Kosary and Huszti described in Acta Chemica Academiae Scientarum Hungaricae, 1975, 80, 167-180.
In some compounds the inactive isomer can be partly converted to the active isomer by gently heating it in a polar solvent, e.g. methanol. The isomers can be separated by any conventional method, e.g., high performance liquid chromatography (HPLC).
The active compounds are well tolerated by plants, have a favourable level of toxicity to warm-blooded animals, and can be used for combating arthropod pests, especially insects or acarids, which are encountered in agriculture, in veterinary practice, in forestry, in the protection of stored products and of materials, and in the hygiene field. They are active against normally sensitive and resistant species and agai
REFERENCES:
patent: 4079149 (1978-03-01), Henry
patent: 4474815 (1984-10-01), Holan et al.
"Pyrethrum The Natural Insecticide", Casida (ed.), Ch. 10, pp. 195-210, Academic Press, NY, 1973.
"Naturally Occurring Insecticides", Jacobsen and Crosby, (eds.), Ch. 1, pp. 59-64, Marcel Dekker, Inc., NY 1971.
"Insecticides Action and Metabolism", O'Brien, pp. 167-168, Academic Press, NY 1967.
Holan George
Johnson Wynona M. P.
Rihs Kurt
Dunlena Pty. Ltd.
Reamer James H.
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