Pyridyl phenyl and benzyl ethers, process and intermediate produ

Details Pyridyl phenyl and benzyl ethers, process and intermediate produ Pyridyl phenyl and benzyl ethers, process and intermediate produ

1998-08-04

2000-09-05

Rotman, Alan L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514348, 546296, 546300, A01N 4340

Patent

active

061143634

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to pyridyl phenyl and pyridyl benzyl ethers of the formula I ##STR2## and their salts and N-oxides where the substituent and indices have the following meanings: CH.sub.3).dbd.CHOC.sub.3, C(CONH.sub.2).dbd.NOCH.sub.3, C(CO.sub.2 CH.sub.3).dbd.NOCH.sub.3, C(CONCH.sub.3).dbd.NOCH.sub.3 or N(OCH.sub.3)--CO.sub.2 CH.sub.3 ; carbon, oxygen, sulfur or nitrogen atom; -haloalkyl; if x is 2; oxygen, sulfur or nitrogen atom; different if y is 2 or 3; -haloalkyl or C.sub.1 -C.sub.4 -alkoxy.
Furthermore the invention relates to processes and intermediates for the preparation of these compounds and to their use for controlling animal pests and harmful fungi.
Pyridyl phenyl and pyridyl benzyl ethers having fungicidal, or fungicidal and insecticidal, properties and which differ from the compounds according to the invention by the substituent in the pyridyl moiety have been disclosed in the literature (EP-A 254 426; EP-A 278 595; EP-A 299 694; EP-A 363 818; EP-A 350 691; EP-A 398 692; EP-A 407 873; EP-A 477 631; EP-A 513 580; JP-A 04/182,461; WO-A 93/15,046).
It was an object of the present invention to provide compounds with an improved activity and a widened spectrum of action.
We have found that this object is achieved by the compounds I defined at the outset. Furthermore, we have found processes and intermediates for the preparation of these compounds, and their use for controlling animal pests and harmful fungi.
The compounds I are accessible via various routes by processes described per se in the literature.
For example, the synthesis of group Q is disclosed in the literature cited at the outset and is carried out in general and in particular by the processes described therein.
When synthesizing the compounds I, a procedure is usually followed in which a pyridine derivative of the formula IIa is converted with a phenol or a benzyl alcohol of the formula IIIa in an inert solvent to give the corresponding ether of the formula IVa, and IV is subsequently reacted with an O-substituted hydroxylamine (R.sup.1 --O--NH.sub.2) or a salt thereof to give I. ##STR3## L.sup.1 in formula IIa is a nucleophilically exchangeable leaving group such as halogen (eg. fluorine, chlorine, bromine or iodine) or alkyl- or arylsulfonate (eg. methylsulfonate, trifluoromethylsulfonate, phenylsulfonate or methylphenylsulfonate). solvent at from 0.degree. C. to 130.degree. C., preferably 20.degree. C. to 80.degree. C., in the presence of a base. 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, and also dimethyl sulfoxide and dimethylformamide, especially preferably tetrahydrofuran, acetonitrile, dimethyl sulfoxide and acetone. Mixtures of these can also be used. 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 also alkali metal hydrogen carbonates, such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and alkali metal alcoholates and alkaline earth metal alcoholates, such as sodium methanolate, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, moreover organic bases, eg. tertiary amines, su

REFERENCES:
patent: 5523454 (1996-06-01), Brand et al.
patent: 5554578 (1996-09-01), Wenderoth et al.

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