Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-12-23
1999-08-03
Richter, Johann
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514357, 514380, 514384, 514524, 514533, 514534, 514538, 544333, 5462721, 5462724, 548243, 5482632, 5482646, 558 13, 560 35, 564265, A61K 3141, A61K 3142, C07C24908, C07C25152, C07D24912, C07D26112
Patent
active
059325836
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel bis-oxime derivatives of the formula I having a microbicidal, insecticidal and acaricidal action, ##STR2## W is oxygen or sulfur, and the other substituents are defined as follows: R.sub.1 =hydrogen, C.sub.1 -C.sub.4 alkyl; cyclopropyl; C.sub.2 -C.sub.6 alkoxyalkyl; C.sub.3 -C.sub.6 cycloalkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; cyano; C.sub.1 -C.sub.6 alkoxycarbonyl; C.sub.1 -C.sub.6 alkyl-S(O).sub.n ; substituted or unsubstituted aryl-S(O).sub.n ; C.sub.1 -C.sub.6 alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted heteroaryloxy; unsubstituted or mono- to trimethyl-substituted heterocyclyl; substituted or unsubstituted aryl-C.sub.1 -C.sub.6 alkyl; substituted or unsubstituted heteroaryl-C.sub.1 -C.sub.6 alkyl; having 1 to 5 halogen atoms; C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.2 -alkyl; unsubstituted or mono- to trihalo-substituted C.sub.1 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 alkynyl; unsubstituted or mono- to tetrahalo-substituted C.sub.3 -C.sub.6 cycloalkyl-C.sub.1 -C.sub.4 alkyl; -C.sub.6 cycloalkyl; C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl;
In a narrower sense, and as a particularly important subgroup, the invention relates to compounds of the formula I in which A is the structural element ##STR3## in which W is oxygen or sulfur, R.sub.2 is as defined with the exception of halo-(C.sub.1 -C.sub.6)alkyl, and R.sub.1, R.sub.3 and n are as defined above.
Substituents of the optionally substituted aryl, heteroaryl, aryl-S(O).sub.n, aryloxy, heteroaryloxy, aryl-C.sub.1 -C.sub.6 alkyl and heteroaryl-C.sub.1 -C.sub.6 alkyl groups include haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, halogen, nitro, cyano, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted heteroarylthio, unsubstituted, mono- or dihalo-substituted and/or mono- or dimethyl-substituted cyclopropylmethoxy, substituted or unsubstituted C.sub.2 -C.sub.6 alkynyl, unsubstituted or mono- to trihalo-substituted C.sub.2 -C.sub.6 alkenyl and unsubstituted or substituted benzyloxy.
Suitable substituents for the latter aryl and heteroaryl groups are halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl (e.g. CF.sub.3) and C.sub.1 -C.sub.4 haloalkoxy (e.g. --OCF.sub.3).
Suitable substituents for a substituted or unsubstituted C.sub.2 -C.sub.6 alkynyl group located on R.sub.2 =aryl (especially phenyl) are: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl (e.g. CF.sub.3), C.sub.1 -C.sub.4 haloalkoxy (e.g. OCF.sub.3), C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, halogen, nitro, cyano, substituted or unsubstituted phenyl, pyridoyl or benzoyl (the substituents on these six-membered rings possibly being C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 OCF.sub.3 !, C.sub.1 -C.sub.4 alkylthio, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl), and also unsubstituted or C.sub.1 -C.sub.4 acylated or O--C.sub.1 -C.sub.4 alkylated C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.5 alkoxycarbonyl; N,N-di(C.sub.1 -C.sub.4 alkyl)carbamoyl; N--C.sub.1 -C.sub.4 alkyl-N--C.sub.1 -C.sub.4 alkoxycarbamoyl; unsubstituted or halo-substituted cyclopropyloxycarbonyl or C.sub.2 -C.sub.5 alkenyl, which is unsubstituted or substituted by C.sub.2 -C.sub.4 alkoxy and/or halogen; and also five- or six-membered heteroaryl with one or more heteroatoms N, O, S, which can be unsubstituted or substituted by one or more of the substituents halogen, cyano, hydroxyl and also alkyl, alkenyl, alkoxy, alkenyloxy, alkynyloxy having in each case up to 4 carbon atoms.
Each substituent may independently of the others be present 1 to 3 times.
An important subgroup of active substance
O'Sullivan Anthony Cornelius
Trah Stephan
Ziegler Hugo
Zurfluh Rene
Morris Michael P.
Novartis Crop Protection, Inc.
Oswecki Jane C.
Peabody, III John D.
Richter Johann
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