Imino oxyphenyl acetic acid derivatives, methods and intermediat

Details Imino oxyphenyl acetic acid derivatives, methods and intermediat Imino oxyphenyl acetic acid derivatives, methods and intermediat

1998-06-25

1999-11-30

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514357, 514406, 514438, 514459, 514542, 514538, 514619, 514522, 514508, 564163, 560 35, 562869, 558414, 558 7, 558391, 549 75, 549426, 548247, 5483371, 5483751, 546329, 546330, 546334, 544336, C07C25160, A01N 3750

Patent

active

059943599

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to 2-iminooxyphenylacetic acid derivatives of the formula I ##STR2## where the substituents and the index have the following meanings: R.sup.1 is C(CO.sub.2 CH.sub.3).dbd.NOCH.sub.3 (Ia), C(CONHCH.sub.3).dbd.NOCH.sub.3 (Ib), C(CONH.sub.2).dbd.NOCH.sub.3 (Ic), C(CO.sub.2 CH.sub.3).dbd.CHOCH.sub.3 (Id) or C(CO.sub.2 CH.sub.3).dbd.CHCH.sub.3 (Ie); -haloalkyl or C.sub.1 -C.sub.4 -alkoxy; when m is 2; -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, cyclopropyl, C.sub.2 -C.sub.6 -alkenyl, the aromatic rings in these radicals to have attached to them one to three of the following groups: cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, or C(CH.sub.3).dbd.N--Y--R.sup.a where atom or a C.sub.1 -C.sub.6 -alkyl group; heterocyclyl, aryl and hetaryl; heterocyclyloxy, aryloxy and hetaryloxy; R.sup.8 where 1,1-cyclopropyl; atom or a C.sub.1 -C.sub.4 -alkyl group; hetaryloxy, arylthio and hetarylthio; -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 l-alkynyl, C.sub.1 -C.sub.10 -alkylcarbonyl, C.sub.2 -C.sub.10 -alkenylcarbonyl, C.sub.2 -C.sub.10 -alkynylcarbonyl or C.sub.1 -C.sub.10 -alkylsulfonyl; arylsulfonyl or hetarylsulfonyl; the aromatic rings to have attached to them one to three of the following substituents: cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -haloalkoxy; are a four- to eight-membered ring which, besides carbon atoms, may contain one or two oxygen and/or sulfur atoms and/or NH and/or N(C.sub.1 -C.sub.4 -alkyl) groups and whose carbon atoms can have attached to them one of the following substituents: halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -alkoxyimino; hetero atoms;
Moreover, the invention relates to processes and intermediates for the preparation of the compounds I, to compositions comprising them, and to their use for controlling animal pests and harmful fungi.
Phenylacetic acid derivatives for controlling animal pests and harmful fungi have been disclosed in the literature (EP-A 370 629, EP-A 463 488, EP-A 460 575, WO-A 95/21,154, WO-A 95/21,153, WO-A 95/18,789).
It is an object of the present invention to provide compounds which are more powerful inhibitors of mitochondrial respiration and thus have an improved activity against animal pests and harmful fungi.
We have found that this object is achieved by the compounds I defined at the outset. We have furthermore found processes and intermediates for the preparation of these compounds, and compositions which are suitable for controlling animal pests and harmful fungi.
The compounds I can be prepared by various routes, it generally being irrelevant whether the group --O--N.dbd.CR.sup.3 R.sup.4 (also termed "side chain" hereinbelow) or the radical R.sup.1 (also termed "pharmacophore" hereinbelow) is synthesized first, or in which precursor of the "pharmacophore" the "side chain" is coupled with the skeleton. C(CO.sub.2 CH.sub.3).dbd.NOCH.sub.3 (Ia), C(CO.sub.2 CH.sub.3).dbd.CHOCH.sub.3 (Id) or C(CO.sub.2 CH.sub.3).dbd.CHCH.sub.3 (Ie), a procedure is followed in which a benzoic ester of the formula II is converted with an oxime of the formula III in the presence of a base to give the corresponding derivative of the formula IV, IV is hydrolyzed to give the corresponding carboxylic acid IVa, and IVa is subsequently first reacted to give the chloride Va and then the cyanide Vb, Vb is converted into the corresponding .alpha.-ketoester VI via a Pinner reaction, and VI is subsequently converted either corresponding compound Ia [R.dbd.C(CO.sub.2 CH.sub.3).dbd.NOCH.sub.3 ], or corresponding compound Id [R.dbd.C(CO.sub.2 CH.sub.3).dbd.CHOCH.sub.3 ], or corresponding compound Ie [R.dbd.C(CO.sub.2 CH.sub.3).dbd.CHCH.sub.3 ]. ##STR3##
L in formula II is a leaving group conventionally used in nucleophilic aromatic substitution, such as halogen (eg. fluorine, chlorine, bromine

Affiliated with

Also associated with

Rating

Imino oxyphenyl acetic acid derivatives, methods and intermediat does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Imino oxyphenyl acetic acid derivatives, methods and intermediat, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Imino oxyphenyl acetic acid derivatives, methods and intermediat will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1672950