Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...
Patent
1998-09-03
2000-03-07
Geist, Gary
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Radical -xh acid, or anhydride, acid halide or salt thereof...
560 27, 560 35, 564147, 564163, 514619, C07C22928, C07C25138, C07C25152, A01N 3716
Patent
active
060341319
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to diphenyl ethers of the formula I, ##STR2## and to their salts and N-oxides where the substituents and indices have the following meanings: CH.sub.3).dbd.CHOCH.sub.3, C(CONH.sub.2).dbd.CHOCH.sub.3, C(CO.sub.2 CH.sub.3).dbd.NOCH.sub.3, C(CONHCH.sub.3).dbd.NOCH.sub.3 or N(OCH.sub.3)--CO.sub.2 CH.sub.3 ; if x is 2; --C(R.sup.2).dbd.NOR.sup.1 is C.sub.2 -C.sub.3 -alkylene which can be interrupted by an oxygen or sulfur atom or can be linked to the phenyl ring via an oxygen or sulfur atom; different if y is 2 or 3; -haloalkyl or C.sub.1 -C.sub.4 -alkoxy.
The invention furthermore relates to processes and intermediates for the preparation of these compounds and to their use for controlling animal pests and harmful fungi.
BACKGROUND ART
The literature (EP-A 253 213; EP-A 254 426; EP-A 280 185; EP-A 307 103; EP-A 398 692; EP-A 477 631; EP-A 513 580; WO-A 93/15,046) discloses phenyl ethers which have fungicidal, or fungicidal and insecticidal, properties which differ from the compounds according to the invention by their substituents.
It is an object of the present invention to provide compounds with an improved activity and a widened spectrum of action.
DISCLOSURE OF INVENTION
We have found that this object is achieved by the compounds I as defined at the outset. We have furthermore found processes and intermediates for the preparation of these compounds and their use for controlling animal pests and harmful fungi.
Compounds I are accessible via various routes by processes known per se from the literature.
For example, the construction of the group Q is disclosed in the literature cited at the outset and is carried out in general and in particular following the processes described therein.
When synthesizing the compounds I where n is 0, a procedure is usually used in which a phenol of the formula IIa is converted with a halobenzene of the formula IIIa in an inert solvent to give the corresponding ether of the formula IVa and IVa is subsequently reacted with an O-substituted hydroxylamine (R.sup.1 --O--NH.sub.2) or with a salt thereof to give I. ##STR3## Hal in the formula IIIa is a halogen atom, such as fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine or bromine. solvent at from 0.degree. C. to 130.degree. C., preferably 20.degree. C. to 80.degree. C., in the presence of a base.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitrites, such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, as well as dimethyl sulfoxide and dimethylformamide, especially preferably tetrahydrofuran, acetonitrile, dimethyl sulfoxide and acetone. Mixtures of these can also be used.
Suitable bases are, generally, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal hydrides and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal carbonates and alkaline earth metal carbonates, such as lithium carbonate and calcium carbonate, and alkali metal hydrogen carbonates, such as sodium hydrogen carbonate, organometal compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and alkali metal alkoxides and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butanolate and dimethoxymagnesium, moreover organic bases,
REFERENCES:
patent: 5298527 (1994-03-01), Grammenos et al.
patent: 5416068 (1995-05-01), Grammenos et al.
Chem. Absts., vol. 60, No. 9, No. 10731a.
Ammermann Eberhard
Bayer Herbert
Grammenos Wassilios
Grote Thomas
Harreus Albrecht
BASF - Aktiengesellschaft
Davis Brian J.
Geist Gary
LandOfFree
Diphenylethers, process and intermediate products for their prep does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Diphenylethers, process and intermediate products for their prep, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Diphenylethers, process and intermediate products for their prep will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-363739