Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-08-24
1996-02-06
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514378, 514523, 548236, 548247, 558391, C07C25564, C07D26108, C07D26332, A01N 4374
Patent
active
054896053
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to cyanooxime ethers of the formula I
R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl;
R.sup.2 is a mononuclear to trinuclear aliphatic or aromatic ring system which is bonded via a carbon atom and may contain, in addition to carbon atoms, from one to four nitrogen atoms or from one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, where this ring system may carry from one to five halogen atoms and/or from one to four of the following radicals: cyano, cyanato, thiocyanato, nitro, amino, hydroxyl, carboxyl, -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.15 -alkenyl, C.sub.3 -C.sub.15 -alkenyloxy, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkenyl, C.sub.3 -C.sub.8 -cycloalkoxy, C.sub.5 -C.sub.8 -cycloalkenyloxy, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylcarboxyl, phenoxy-C.sub.1 -C.sub.4 -alkyl, phenylthio-C.sub.1 -C.sub.4 -alkyl or phenylamino-C.sub.1 -C.sub.4 -alkyl, where the aromatic rings in turn may carry from one to five halogen atoms and/or from one to three of the following radicals: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -haloalkylthio, carbon atom and, in addition to carbon atoms, may contain from one to three nitrogen atoms or one or two nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, where this ring system may carry from one to four halogen atoms and/or from one to three of the following radicals: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.3 is unsubstituted or substituted alkyl or an unsubstituted or substituted aliphatic ring system which is bonded via a carbon atom and, in addition to carbon atoms, may contain one or two hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.
The present invention furthermore relates to a process for the preparation of these compounds, to pesticides containing the compounds I and to their use.
The literature discloses cyanooxime ethers as active ingredients for protecting plants and as drugs (fungicides: EP-A 370 629; growth regulators: U.S. Pat. No. 4,451,286; antidotes: EP-A 12 158, EP-A 122 231; insecticides: EP-A 303 934; herbicides: DE-A 28 37 857; drugs: DE-A 28 00 316).
Furthermore, EP-A 463 488 discloses phenylacetic acid derivatives which have oxime ether groups and are suitable for controlling pests and are noteworthy for their fungicidal.
It is an object of the present invention to provide novel compounds suitable for controlling pests.
We have found that this object is achieved by the cyanooxime ethers of the formula I which are defined at the outset. We have also found processes for the preparation of these compounds, pesticides containing these compounds and their use.
The novel compounds are obtained in general by etherifying a cyanooxime of the formula II in a conventional manner, in an inert organic solvent, with a compound III. ##STR1##
In the formula III, X is a nucleofugic leaving group, such as halogen, for example chlorine, bromine or iodine, an aromatic or aliphatic sulfonate, for example p-toluenesulfonate, methanesulfonate or triflate, or carboxylate, such as acetate, in particular chlorine or bromine.
This reaction is usually carried out at from -20.degree. to 100.degree. C., preferably from 20.degree. to 80.degree. C.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xyl
REFERENCES:
patent: 4327213 (1982-04-01), Van Zorge
patent: 4347372 (1982-08-01), Fory et al.
patent: 4363041 (1982-12-01), Lelandais
patent: 4424215 (1984-01-01), Buerstinghaus et al.
patent: 4451286 (1984-05-01), Martin
patent: 4612306 (1986-09-01), Burstinghaus et al.
patent: 4670425 (1987-06-01), Buerstinghaus et al.
patent: 4857524 (1989-08-01), Furukawa et al.
patent: 5055471 (1991-10-01), de Fraine et al.
patent: 5568668 (1986-02-01), Burstinghaus et al.
patent: 5760056 (1988-07-01), Burstinghaus et al.
J. Smiti et al., Arch. Pharm. 304 (1971), 425-429.
Rec. Trav. Chim. Pays-Bas 91 (1972), 711.
J. Org. Chem, 25 (19) (1960).
Harreus Albrecht
Harries Volker
Kardorff Uwe
Koenig Hartmann
Oberdorf Klaus
BASF - Aktiengesellschaft
Gerstl Robert
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