Patent ID: 6069144
Filing Date: 2000-05-30
Classification: A01N,C07D

Abstract:
An N-heterocyclic compound of the formula I ##STR76## or a salt or N-oxide thereof, where the variables have the following meanings:A is an N-heterocycle selected from the group consisting of ##STR77## where the groups R.sup.1 to R.sup.6 and R.sup.24 to R.sup.26 independently of one another are: hydrogen, cyano, nitro, halogen, aminocarbonyl, methylsulfonyl, 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, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl, aryl or aryloxy, where the aryl rings may carry one to three groups selected from: cyano, nitro, halogen, 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, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl and C.sub.1 -C.sub.4 -acyl;m is 0, 1 or 2;Alk is 1,2-ethylidene or 1,3-propylidene, where the hydrogen atoms of these chains may be replaced independently of one another by one of the following groups: C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -haloalkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -haloalkenyl or C.sub.2 -C.sub.8 -alkynyl, where each of these 5 radicals additionally may carry one to three groups selected from: cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, (C.sub.1 -C.sub.4 -alkoxy)carbonyl, C.sub.3 -C.sub.7 -cycloalkyl and C.sub.5 -C.sub.7 -cycloalkenyl; C.sub.3 -C.sub.7 -cycloalkyl and C.sub.5 -C.sub.7 -cycloalkenyl, where these radicals may be partially or fully halogenated or may carry one to three groups selected from: cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl and C.sub.1 -C.sub.4 -alkoxy;X is oxygen or sulfur;Q is aryl, which may carry one to three groups selected from: cyano, nitro, halogen, 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, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl, C.sub.1 -C.sub.4 -acyl, C.sub.1 -C.sub.4 -alkylsulfinyl, C.sub.1 -C.sub.4 -alkylsulfonyl, aryl and aryloxy, where these aryl rings, in turn, additionally may carry one to three substituents selected from: cyano, nitro, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-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, (C.sub.1 -C.sub.4 -alkoxy)carbonyl and C.sub.1 -C.sub.4 -acyl;C.sub.3 -C.sub.7 -cycloalkyl and C.sub.5 -C.sub.7 -cycloalkenyl, where these rings may be partially or fully halogenated or may carry one to three groups selected from: cyano, halogen, 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 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, (C.sub.1 -C.sub.4 -alkoxy)carbonyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.5 -C.sub.7 -cycloalkenyl, aryl and aryloxy, where these aryl rings, in turn, additionally may carry one to three substituents selected from: cyano, nitro, halogen, 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 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, (C.sub.1 -C.sub.4 -alkoxy)carbonyl and C.sub.1 -C.sub.4 -acyl;aryl-C.sub.1 -C.sub.4 -alkyl, where the aryl ring may carry one to three groups selected from: cyano, nitro, halogen, 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 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, (C.sub.1 -C.sub.4 -alkoxy)carbonyl, C.sub.1 -C.sub.4 -acyl, aryl and aryloxy, where these aryl rings, in turn, additionally may carry one to three substituents selected from: cyano, nitro, halogen, 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 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, (C.sub.1 -C.sub.4 -alkoxy)carbonyl and C.sub.1 -C.sub.4 -acyl;with the exception ofa) the compounds V1 to V25 where A is A1 and R.sup.4 is H: No. R.sup.1 R.sup.2 R.sup.3 m Alk X Q  V1 H H H 0 1,2- --O-- phenyl ethylidene V2 H H H 2 1,2- --O-- phenyl ethylidene V3 5-CF.sub.3 H H 0 1,2- --O-- 4-chloro- ethylidene phenyl V4 5-CF.sub.3 H H 0 1,2- --O-- 4-methyl- ethylidene phenyl VS 5-CF.sub.3 H H 2 1,2- --O-- phenyl ethylidene V6 5-CF.sub.3 H H 2 1,2- --O-- 2-chloro- ethylidene phenyl V7 5-CF.sub.3 H H 2 1,2- --O-- 3-chloro- ethylidene phenyl V8 5-CF.sub.3 H H 2 1,2- --O-- 4-chloro- ethylidene phenyl V9 5-CF.sub.3 H H 2 1,2- --O-- 3,4-dichloro- ethylidene phenyl V10 5-CF.sub.3 H H 2 1,2- --O-- 4-methyl- ethylidene phenyl V11 5-CF.sub.3 H H 2 1,2- --O-- 4-methoxy- ethylidene phenyl V12 5-CF.sub.3 H H 2 1,2- --O-- 4-trifluoro- ethylidene methyl- phenyl V13 5-CF.sub.3 H H 2 1,2- --O-- 4-tert- ethylidene butylphenyl V14 H H H 2 1,2- --O-- 3-chloro- ethylidene phenyl V15 H H 3-Cl 2 1,2- --O-- 3-chloro- ethylidene phenyl V16 5-Cl H H 2 1,2- --O-- 3-chloro- ethylidene phenyl V17 6-Cl H H 2 1,2- --O-- 3-chloro- ethylidene phenyl V18 H H 3-CN 2 1,2- --O-- 3-chloro- ethylidene phenyl V19 H H 3- 2 1,2- --O-- 3-chloro- CF.sub.3 ethylidene phenyl V20 H H 3- 2 1,2- --O-- 3-chloro- NO.sub.2 ethylidene phenyl V21 5-NO.sub.2 H H 2 1,2- --O-- 3-chloro- ethylidene phenyl V22 6-CH.sub.3 H H 2 1,2- --O-- 3-chloro- ethylidene phenyl V23 6-OCH.sub.3 H H 2 1,2- --O-- 3-chloro- ethylidene phenyl V24 5- H H 2 1,2- --O-- 3-chloro- COOCH.sub.3 ethylidene phenyl V25 6-CH.sub.3 4- H 2 1,2- --O-- 3-chloro- CF.sub.3 ethylidene phenyl  b) the compound I where A is the N-oxide A1, and where R.sup.1, R.sup.2, R.sup.3, R.sup.4 are H; m is 2, Alk is 1,2-ethylidene; X is --O--; Q is phenyl.