Patent DE-19818732-A1 (DE)
Title: New aryl substituted cyclic ketoenol compounds useful for control of insects and as herbicides
Inventor: LIEB FOLKER
IPC: C07C49/747
Filed: 1998-04-27
Abstract: Cycloalkyl- and (hetero)aryl-phenyl substituted cyclic ketoenols (I) and their intermediates (II) are new. Cycloalkyl- and (hetero)aryl-phenyl substituted cyclic ketoenols of formula (I) are new:  X  = halo; alkyl, alkoxy or alkenyloxy optionally substituted with halo; alkylthio; alkylsulfinyl; alkylsulfonyl; NO2; CN; or optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy; or phenylalkylthio;  Y  = optionally substituted cycloalkyl, aryl or heteroaryl;  W  = H; halo; alkyl, alkoxy or alkenyloxy optionally substituted with halo; NO2; or CN;  Z'  = halo; alkyl, alkoxy or alkenyloxy optionally substituted with halo; NO2; or CN; CKE = group of formula (1)-(6); Q  = N-D; O or S;  A  = H; alkyl, alkenyl, (poly)alkoxyalkyl or alkylthioalkyl optionally substituted with halo; saturated or unsaturated cycloalkyl optionally substituted and optionally containing 1 or more hetero ring atoms; or aryl, aralkyl or heteroaryl optionally substituted with halo, alkyl, haloalkyl, alkoxy, haloalkoxy, CN or NO2;  B  = H; alkyl or alkoxyalkyl; or  A + B + C atom = form a saturated or unsaturated cyclic group optionally substituted and optionally containing 1 or more hetero ring atoms; D = H; optionally substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, (poly)alkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl optionally containing 1 or more hetero ring atoms, aralkyl, aryl, heteroarylalkyl or heteroaryl; or  A + D + N atom = form a saturated or unsaturated cyclic group optionally substituted and optionally containing 1 or more hetero atoms or further hetero atom(s) when CKE is formula (2); or A + Q<1> = form alkanediyl or alkenediyl optionally substituted with optionally substituted alkyl, OH, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl; or Q<1> = H or alkyl; Q<2>, Q<4>, Q<5> and Q<6> = H or alkyl; Q<3> = H; alkyl; alkoxyalkyl; alkylthioalkyl; cycloalkyl optionally substituted and optionally containing S or O in place of 1 CH2; or optionally substituted phenyl; or Q<3> + Q<4> + C atom = form a saturated or unsaturated cyclic group optionally substituted and optionally containing a hetero atom; or G = H or a group of formula (b)-(g): E = metal or ammonium ion; L and M = O or S; R<1> = alkyl, alkenyl, (poly)alkoxyalkyl or alkylthioalkyl optionally substituted with halo; cycloalkyl optionally substituted with halo, alkyl or alkoxy and optionally containing 1 or more ring hetero atoms; or optionally substituted phenyl, phenylalkyl, heteroaryl, phenoxyalkyl or heteroaryloxyalkyl; R<2> = alkyl, alkenyl or (poly)alkoxyalkyl optionally substituted with halo; or optionally substituted cycloalkyl, phenyl or benzyl; R<3>, R<4> and R<5> = alkyl, alkoxy, mono- or di-alkylamino, alkylthio, alkenylthio or cycloalkylthio optionally substituted with halo; or optionally substituted phenyl, benzyl, phenoxy or phenylthio; R<6> and R<7> = H; alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl optionally substituted with halo; or optionally substituted phenyl or benzyl; or  NR<6>R<7> = forms a cyclic group optionally interrupted with O or S.  Independent claims are also included for: (a) the preparation of compounds (I); and (b) intermediates of formula (II):  R  = -CH2-C(O)-N(D)-C(A)(B)(CO2R<8>) ; -CH2-CO-Hal ; or-CH2-C(O)-N(D)-C(A)(B)(CO2H); -CH2-C(O)-N(D)-C(A)(B)(CN) ; -CH2-CO-O-C(A)(B)(CO2R<8>); -CH2CO2H; or -CH2CO2R<8>; B(OH)2 and Y = -CH2-CO2H ; CH(CO2R<8>)(CO-C(A)(B)(S-CH2-Ar)); -C(=C=O)(COHal); -CH(CO2H)2; or-CH(CO2R<8>)2; -CH2-CO-C(Q<1>)(Q<2>)-C(A)(B)(CO2R<8>); -CH2-CO-C(Q<1>)(Q<2>)-C(A)(B)(CO2H); -CH2-CO-C(Q<5>)(Q<6>)-C(Q<3>)(Q<4>)-C(A)(B)(CO2R<8>); -CH2-CO-C(Q<5>)(Q<6>)-C(Q<3>)(Q <4>)-C(A)(B)(CO2H); -CH(CO2R<8>')-CO-C(Q<5>)(Q<6>)-C(Q<3>)(Q<4>)-C(A)(B)(CO2R<8>); R<8> and R<8>'  = alkyl;  Hal  = Cl or Br;  Ar  = phenyl optionally substituted with W.