Patent ID: 6288071
Filing Date: 2001-09-11
Classification: A01N,C07C,C07D

Abstract:
A compound of formula I##STR817##wherein:X is CH or N;Y is O, S, S.dbd.O or NR.sub.5 ;Z is OR.sub.2, SR.sub.2 or N(R.sub.3)R.sub.4 ;n is 0, 1, 2, 3, 4 or 5; orY and Z together form a 5- to 7-membered ring having 2 or 3 hetero atoms O and/or N that is unsubstituted or mono- or poly-substituted by C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halogen, .dbd.O or by cyclopropyl;W is an aldimino or ketimino group selected from the group consisting of group a)##STR818##whereinR.sub.11 and R.sub.12 are each independently of the other hydrogen, cyano, C.sub.1 -C.sub.12 alkyl, halo-C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.12 alkenyl, C.sub.2 -C.sub.12 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, cyclopropylmethyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.12 alkoxyalkyl, C.sub.1 -C.sub.4 alkoxycarbonyl, aminocarbonyl, C.sub.1 -C.sub.4 alkylaminocarbonyl, bis(C.sub.1 -C.sub.4 alkyl)aminocarbonyl, ureidocarbonyl, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkylthioalkyl; an unsubstituted or up to penta-substituted ring having a maximum of 15 ring carbon atoms that may be multi-membered and has from 0 to 3 hetero atoms N, O and/or S, it being possible for the ring to be bonded by a bridge having a maximum of 4 chain atoms and that may be linear or branched and may contain CO, oxygen or sulfur; orR.sub.11 and R.sub.12 together with the common carbon atom are an unsubstituted or up to penta-substituted ring having a maximum of 15 ring carbon atoms that may be multi-membered and has from 0 to 3 hetero atoms N, O and/or S;the possible substituents of all of those groups mentioned for R.sub.11 and R.sub.12 individually or together being selected from C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 haloalkynyl, C.sub.1 -C.sub.4 haloalkoxy, halogen, cyano, cyano-C.sub.1 -C.sub.2 alkyl, cyano-C.sub.1 -C.sub.2 alkoxy, oxo, thioxo, OH, NO.sub.2, SCN, thiocyanomethyl, Si(CH.sub.3).sub.3, NH.sub.2, NH(C.sub.1 -C.sub.4 alkyl), N(C.sub.1 -C.sub.4 alkyl).sub.2, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylcarbonyl, C.sub.1 -C.sub.4 haloalkylcarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 haloalkoxycarbonyl, aminocarbonyl, C.sub.1 -C.sub.4 alkyl-aminocarbonyl, bis(C.sub.1 -C.sub.4 alkylamino)carbonyl, arylaminocarbonyl, arylaminothiocarbonyl, C.sub.1 -C.sub.4 haloalkylcarbonyloxy, C.sub.1 -C.sub.4 alkylcarbonyloxy, C.sub.1 -C.sub.4 alkoxycarbonyloxy, aminocarbonyloxy, C.sub.1 -C.sub.4 alkylaminocarbonyloxy, bis(C.sub.1 -C.sub.4 alkylamino)carbonyloxy, arylaminocarbonyloxy, arylaminothiocarbonyloxy, C.sub.1 -C.sub.4 alkoximinomethyl, --CSNH.sub.2, --SH, C.sub.1 -C.sub.4 alkylthiomethyl, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.1 -C.sub.4 alkylsulfinylmethyl, C.sub.1 -C.sub.4 alkylsulfonylmethyl, phenylsulfinylmethyl, phenylsulfonylmethyl, trifluoromethylsulfonyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, benzyl, phenoxy, phenylthio, benzyloxy and benzylthio;it being possible for the aromatic groups to carry a maximum of 5 further substituents selected from halogen, 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, CN and NO.sub.2, and it being possible for two adjacent substituents of the maximum of 5 substituents to form an aliphatic bridge having a maximum of 5 members, which bridge has from 0 to 2 oxygen atoms and 0 or 1 carbonyl group and may be substituted a maximum of four times by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and/or by a single phenyl group;or wherein##STR819##R.sub.12 is a group e)wherein:R.sub.13 is hydrogen, cyano, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, heteroaryl, heterocyclyl, naphthyl, C.sub.1 -C.sub.6 alkoxy, aryloxy, heteroaryloxy, C.sub.1 -C.sub.6 alkylamino, bis(C.sub.1 -C.sub.6 alkyl)amino, arylamino or heteroarylamino, it being possible for all of the radicals mentioned other than cyano to be unsubstituted or substituted by alkyl, alkoxy, haloalkyl, haloalkoxy, alkylthio, alkylsulfenyl, alkylsulfinyl, halogen, nitro, cyano, aryl, aryloxy, heteroaryl or by heteroaryloxy,or a group f)##STR820##whereinR.sub.15 is C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo-C.sub.1 -C.sub.6 alkoxy, halogen, C.sub.3 -C.sub.6 cycloalkyl unsubstituted or substituted by from 1 to 5 halogen atoms, C.sub.2 -C.sub.6 alkenyl, halo-C.sub.2 -C.sub.6 alkenyl, optionally substituted C.sub.3 -C.sub.6 -alkynyl, cyano, cyano-C.sub.1 -C.sub.2 alkyl, cyano-C.sub.1 -C.sub.2 alkoxy, OH, NO.sub.2, SCN, thiocyanomethyl, Si(CH.sub.3).sub.3, NH.sub.2, NH(C.sub.1 -C.sub.4 alkyl), N(C.sub.1 -C.sub.4 alkyl).sub.2, C.sub.1 -C.sub.4 alkoxymethyl, C.sub.1 -C.sub.4 haloalkylcarbonyl, C.sub.1 -C.sub.4 alkylcarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, aminocarbonyl, C.sub.1 -C.sub.4 alkylaminocarbonyl, bis(C.sub.1 -C.sub.4 alkylamino)carbonyl, arylaminocarbonyl, arylaminothiocarbonyl, C.sub.1 -C.sub.4 alkoximinomethyl, --CSNH.sub.2, --SH, C.sub.1 -C.sub.4 alkylthiomethyl, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.1 -C.sub.4 alkylsulfinylmethyl, C.sub.1 -C.sub.4 alkyl sulfonylmethyl, phenylsulfinylmethyl, phenylsulfonylmethyl, trifluoromethylsulfonyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 haloalkylcarbonyloxy, C.sub.1 -C.sub.4 alkylcarbonyloxy, C.sub.1 -C.sub.4 alkoxycarbonyloxy, aminocarbonyloxy, C.sub.1 -C.sub.4 alkylaminocarbonyloxy, bis(C.sub.1 -C.sub.4 alkylamino)carbonyloxy, arylaminocarbonyloxy, arylaminothiocarbonyloxy, aryl, heteroaryl or heterocyclyl;the aromatic groups in R.sub.15 each independently of the others being unsubstituted or mono- to penta-substituted by C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.6 alkyl, halogen, C.sub.1 -C.sub.6 alkoxy or by halo-C.sub.1 -C.sub.6 alkoxy; tri(C.sub.1 -C.sub.4 alkyl)silyl or di(C.sub.1 -C.sub.4 alkyl)phenylsilyl;wherein when n is greater than 1 the R.sub.15 radicals may be identical or different;Q is a direct bond, C.sub.1 -C.sub.8 alkylene, C.sub.2 -C.sub.6 alkenylene, C.sub.2 -C.sub.6 alkynylene, O, O(C.sub.1 -C.sub.6 alkylene), (C.sub.1 -C.sub.6 alkylene)O, S(.dbd.O)p, S(.dbd.O).sub.p (C.sub.1 -C.sub.6 alkylene) or (C.sub.1 -C.sub.6 alkylene)S(.dbd.O).sub.p ;m is 0, 1, 2, 3, 4 or 5;p is 0, 1 or 2; andR.sub.14 is hydrogen; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl having from 1 to 15 halogen atoms; C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.2 alkyl; C.sub.2 -C.sub.4 alkenyl-C.sub.1 -C.sub.2 alkyl unsubstituted or substituted by from 1 to 3 halogen atoms; C.sub.2 -C.sub.4 alkynyl-C.sub.1 -C.sub.2 alkyl; C.sub.3 -C.sub.6 cycloalkyl unsubstituted or substituted by from 1 to 4 halogen atoms; C.sub.3 -C.sub.6 cycloalkyl-C.sub.1 -C.sub.4 alkyl unsubstituted or substituted by from 1 to 4 halogen atoms; cyano-C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkoxycarbonyl-C.sub.1 -C.sub.4 alkyl; phenyl-C.sub.1 -C.sub.3 alkyl unsubstituted or substituted by halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, cyano, nitro and/or by C.sub.1 -C.sub.4 alkylenedioxy and wherein the phenyl group may be substituted by from 1 to 3 identical or different substituents; phenyl unsubstituted or substituted by one or two substituents, which may be the same or different, selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1 -C.sub.2 haloalkyl having from 1 to 3 halogen atoms, nitro and cyano; or pyridyl unsubstituted or substituted by one or two substituents, which may be the same or different, selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1 -C.sub.2 haloalkyl having from 1 to 3 halogen atoms, nitro and cyano;R.sub.1 is cyclopropyl, C.sub.1 -C.sub.6 alkyl or halo-C.sub.1 -C.sub.6 alkyl;R.sub.2 and R.sub.3 are each independently of the other C.sub.1 -C.sub.6 alkyl or halo-C.sub.1 -C.sub.6 alkyl;R.sub.4 and R.sub.5 are each independently of the other hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy;R.sub.8 and R.sub.9 are each independently of the other hydrogen or C.sub.1 -C.sub.3 alkyl; orR.sub.8 and R.sub.9 together are C.sub.2 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 cycloalkyl;R.sub.21 and R.sub.22 are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy or C.sub.1 -C.sub.8 alkylthio; andR.sub.23, R.sub.24, R.sub.25 and R.sub.26 are each independently of the others hydrogen, halogen, C.sub.1 -C.sub.8 alkyl or C.sub.1 -C.sub.8 alkoxy.