Patent ID: 6265398
Filing Date: 2001-07-24
Classification: A01N,C07D

Abstract:
A compound of formula I ##STR18##in whichR.sup.1 is hydrogen, halogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl or (C.sub.3 -C.sub.5)-cycloakyl;R.sub.2 and R.sub.3 are identical or different and are in each case hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.2 -C.sub.4)-alkenyl, (C.sub.2 -C.sub.4)-haloalkenyl, (C.sub.2 -C.sub.4)-alkynyl, (C.sub.2 -C.sub.4) -haloalkynyl, tri-(C.sub.1 -C.sub.4)-alkylsilyl-(C.sub.2 -C.sub.4)-alkynyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 C.sub.4)-haloalkoxy, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkoxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)-haloalkoxy-(C.sub.1 -C.sub.4)-haloalkyl, halogen, hydroxyl, (C.sub.1 -C.sub.4)-hydroxyalkyl, (C.sub.1 -C.sub.4)-alkanoyl, (C.sub.1 -C.sub.4)-alkanoyl-(C.sub.1 -C.sub.4)-alkyl, (C.sub.2 -C.sub.4)-haloalkanoyl, (C.sub.3 -C.sub.5)-cycloalkyl, (C.sub.4 -C.sub.5)-cycloalkenyl, (C.sub.3 -C.sub.5)-cycloalkoxy, (C.sub.3 -C.sub.5)-halocycloalkyl, (C.sub.4 -C.sub.5)-halocycloalkenyl, cyano, (C.sub.1 -C.sub.4)-cyanoalkyl, nitro, (C.sub.1 -C.sub.4)-nitroalkly, thiocyano, (C.sub.1 -C.sub.4)-thiocyanoalkyl, (C.sub.1 -C.sub.4)-alkoxycarbonyl, (C.sub.1 -C.sub.4)-alkoxycarbonyl-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkoxycarbonyl, (C.sub.1 -C.sub.4)-alkanoyloxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkylthio, (C.sub.1 -C.sub.4)-alkylthio-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)haloalkylthio, (C.sub.1 -C.sub.4)-alkylsulfinyl, (C.sub.1 -C.sub.4)-haloalkylsulfinyl, (C.sub.1 -C.sub.4)- or (C.sub.1 -C.sub.4)-haloalkylsulfonoyl;A is N;X is NH, O or S(O).sub.q where q is 0, 1 or 2;Y.sup.1 Y.sup.2 and Y.sup.3 independently of one another are a group of he formula --O--, --CO--, --CNR.sup.6 --, --S(O).sub.r --, --N(O).sub.1 R.sup.6 -- or CR.sup.7 R.sup.8 where r is 0, 1 or 2 and 1 is 0 or 1 orY.sup.1 or Y.sup.3 replace a direct bond;R.sup.4 is hydrogen of (C.sub.1 -C.sub.4)-alkyl;m is 0or 1;n is 0, 1, 2, 3 or 4;Z is a direct bond, NR.sup.9, O, S(O).sub.s where s is 0, 1 or 2, OSO.sub.2, SO.sub.2 O, NR.sup.10 SO.sub.2, SO.sub.2 NR .sup.11, SiR.sup.12 R.sup.13, U.sup.1 P(W.sup.1)V.sup.1 V.sup.2 or ##STR19##whereU.sup.1, U.sup.2 in dependently of one another are direct bond, NR.sup.14 or O;W.sup.1, W.sup.2 independently of one another are oxygen or sulfur;V.sup.1, V.sup.2, V.sup.3 independently of one another a direct bond, NR.sup.15 or oxygen, whereR.sup.9, R.sup.10, R.sup.11, R.sup.14 and R.sup.15 are identical or different and are in each case hydrogen alkyl, alkoxy, alkanoyl or cycloalkyl;R.sup.5 radicals are substituents which are independent of one another and are halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and it being possible for one or more non-adjacent saturated carbon units in the last-mentioned 5 radicals to be replaced by a carbonyl group or by oxygen, S(O).sub.x where x is 0, 1 or 2, NR.sup.16 or SiR.sup.17 R.sup.18, and wherein these last-mentioned 5 radicals, with or without the above mentioned variations, are optionally substituted by one or more, in the case of fluorine up to the maximum number of identical or different radicals D.sup.1 R.sup.19, orR.sup.5 is aryl or heterocyclyl, it being possible for these two radicals to be unsubstituted or to be substituted by up to three, in the case of fluorine also up to the maximum number of, identical or different radicals D.sup.2 R.sup.20, or two adjacent radicalsZ--R.sup.5 together with the carbon atoms to which they are attached can form a fused cycle having 4 to 6 ring atoms which is carbocyclic or contains hetero ring atoms selected from the group consisting of O, S and N and which is unsubstituted of substituted by one or more radicals selected from the group consisting of halogen, (C.sub.1 -C.sub.4)-alkyl and oxo, orR.sup.6, R.sup.10, R.sup.11 or R.sup.15 independently of one another together with the R.sup.5 which is attached to Z can be form a 4- to 8-membered ring system in which one or two CH.sub.2 groups are optionally replaced by oxygen, S(O).sub.t where t is 0, 1 or 2 or NR.sup.25, whereR.sup.6 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.2 -C.sub.4)-alkenyl, (C.sub.2 -C.sub.4)-haloalkenyl, (C.sub.2 -C.sub.4)-alkynyl, (C.sub.2 -C.sub.4)-haloalkynyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-haloalkoxy, (C.sub.1 C.sub.4)-alkythio, (C.sub.1 -C.sub.4)-haloalkylthio, (C.sub.1 -C.sub.4)-alkanoyl, (C.sub.2 -C.sub.4)-haloalkanoyl, (C.sub.3 -C.sub.5)-cycloalkyl, (C.sub.1 -C.sub.4,)-alkylsulfonyl, (C.sub.1 -C.sub.4)haloalkylsulfonyl, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxycarbonyl;R.sup.7 and R.sup.8 independently of one another are hydrogen, hydroxyl, halogen, cyano, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.2 -C.sub.4)-alkenyl, (C.sub.2 -C.sub.4)-haloalkenyl, (C.sub.2 -C.sub.4)-alkynyl, (C.sub.2 -C.sub.4)-haloalkenyl, (C.sub.3 -C.sub.5)-cycloalkyl, (C.sub.1 -C.sub.4)-alkanoyl, (C.sub.1 -C.sub.4)-haloalkanoyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-haloalkoxy, (C.sub.1 -C.sub.4)-haloalkoxy, (C.sub.1 -C.sub.4)-alkylthio or (C.sub.1 -C.sub.4)-haloalkylthio;R.sup.12 and R.sup.13 independently of one another are (C.sub.1 -C.sub.4)-alkyl or phenyl;R.sup.16 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-alkanoyl;R.sup.17 and R.sup.18 independently of one another are (C.sub.1 -C.sub.4)-alkyl,D.sup.1 and D.sup.2 are in each case independent of one another and are a direct bond, oxygen, S(O).sub.k, SO.sub.2 O, OSO.sub.2, CO, OCO, COO, NR.sup.21, SO.sub.2 NR.sup.21, NR.sup.21 SO.sub.2, ONR.sup.21, NR.sup.21 O NR.sup.21 CO, CONR.sup.21 or SiR.sup.22 R.sup.23 and k is 0, 1 or 2, whereR.sup.21 radicals independently of one another are hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkanoyl or (C.sub.3 -C.sub.5)-cycloalkyl;R.sup.22 and R.sup.23 independently of one another are (C.sub.1 -C.sub.4)-alkyl;R.sup.19 and R.sup.20 independently of one another are hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynl, alkoxyalkyl, haloalkoxyalkyl, alklylthioalkyl, haloalkylthioalkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, aryl, heterocyclyl, aryalkyl or heterocyclyalkyl, the cycloalipathic, aromatic or heterocyclic ring systems in the last-mentioned 8 radicals being unsubstituted or substituted or with one to three, in the case of fluorine also up to the maximum number of, identical or different substituents R.sup.24, orR.sup.19 and R.sup.20, attached to the same carbon atom, together are an oxo group; whereR.sup.24 radicals independently of one another are (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, cyano, nitro or halogen;R.sup.25 independently of one another are hydrogen, (C.sub.1 -C.sub.8)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-alkylthio, (C.sub.3 -C.sub.5)-cycloalkyl, (C.sub.2 -C.sub.4)-alkenyl, (C.sub.2 -C.sub.4)-alkynyl, (C.sub.1 -C.sub.4)-alkanoyl, (C.sub.1 -C.sub.4)-haloalkanoyl, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, phenyl-(C.sub.1 -C.sub.4)-alkyl or phenyl, the phenyl groups independently of one another being unsubstituted or being provided with up to three, in the case of fluorine also up to the maximum number of, identical or different substituents R.sup.26, whereR.sup.26 substituents independently of one another are (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)-alkylthio, halogen or cyano,or a salt thereof.