Patent ID: 6232470
Filing Date: 2001-05-15
Classification: A01N,C07D

Abstract:
A substituted pyrazol-3-ylbenzazole of the formula I ##STR50##where:R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl;R.sup.2 is cyano, 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 -haloalkylthio, C.sub.1 -C.sub.4 -alkylsuffinyl, C.sub.1 -C.sub.4 -haloalkylsulfinyl, C.sub.1 -C.sub.4 -alkylsulfonyl or C.sub.1 -C.sub.4 -haloalkylsulfonyl;R.sup.3 is hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl;R.sup.4 is hydrogen or halogen;R.sup.5 is hydrogen, halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -haloalkoxy;Z is a group --N.dbd.C(XR.sup.6)--O-- or --N.dbd.C(XR.sup.6)--S-- which is bonded to a by the nitrogen, oxygen or sulfur;X is a chemical bond, oxygen, sulfur, --S(O)--, --SO.sub.2 --, --NH-- or --N(R.sup.7)--;R.sup.6 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, cyano-C.sub.1 -C.sub.4 -alkyl, hydroxy-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, cyano-C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -haloalkenyl, C.sub.3 -C.sub.6 -alkynyl, cyano-C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -haloalkynyl, 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.3 -C.sub.4 -alkenyloxy-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkynyloxy-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.8 -cloalkyloxy-C.sub.1 -C.sub.4 -alkyl, amino-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylamino-C.sub.1 -C.sub.4 -alkyl, di(C.sub.1 -C.sub.4 -alkyl)amino-C.sub.1 -C.sub.4 -alkyl, 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 -alkyl, C.sub.3 -C.sub.4 -alkenylthio-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkynylthio-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylsulfinyl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkylsulfinyl-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenyl-sulfinyl-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkynylsulfinyl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylsulfonyl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl-sulfonyl-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenylsulfonyl-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkynylsulfonyl-C.sub.1 -C.sub.4 -alkyl, hydroxycarbonyl- C.sub.1 -C.sub.4 -alkyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl-C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by a cyano or (C.sub.1 -C.sub.4 -alkoxy)carbonyl group, (C.sub.1 -C.sub.4 -alkylthio)carbonyl-C.sub.1 -C.sub.4 -alkyl, aminocarbonyl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylamino-carbonyl-C.sub.1 -C.sub.4 -alkyl, di(C.sub.1 -C.sub.4 -alkyl)aminocarbonyl- C.sub.1 -C.sub.4 -alkyl, di(C.sub.1 -C.sub.4 -alkyl)phosphonyl-C.sub.1 -C.sub.4 -alkyl, (C.sub.1 -C.sub.4 -alkoxy)imino-C.sub.1 -C.sub.4 -alkyl, (C.sub.3 -C.sub.4 -alkenyloxy)imino-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl, phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl, 3- to 7-membered heterocyclyl or heterocyclyl-C.sub.1 -C.sub.4 -alkyl, (C.sub.1 -C.sub.4 -alkyl)carbonyl, (C.sub.1 -C.sub.4 -haloalkyl)carbonyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -haloalkylsulfonyl, hydrogen, cyano, mercapto, amino, halogen, --CH.sub.2 --CH(halogen)-R.sup.8, --CH.dbd.CH--R.sup.8 or --CH.dbd.C(halogen)--R.sup.8, where R.sup.8 is hydroxycarbonyl, (C.sub.1 -C.sub.4 -alkoxy)ycarbonyl, (C.sub.1 -C.sub.4 -alkylthio)carbonyl, aminocarbonyl, C.sub.1 -C.sub.4 -alkylaminocarbonyl, di(C.sub.1 -C.sub.4 -alkyl)aminocarbonyl or di(C.sub.1 -C.sub.4 -alkyl)phosphonyl, with the provisos that if X is a oxygen, sulfur, --NH--, --N(R.sup.7)--, --S(O)-- or --SO.sub.2 --, R.sup.6 is not hydroaen, cyano, mercapto, amino, halogen, --CH.sub.2 --CH(haloaen)-R.sup.8, --CH.dbd.CH--R.sup.8 or --CH.dbd.C(halogen)-R.sup.8, and if X is --S(O)-- or --SO.sub.2, R.sup.6 is not (C.sub.1 -C.sub.4 -alkyl)carbonyl, C.sub.1 -C.sub.4 -haloalkyl)carbonyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl or C.sub.1 -C.sub.4 -haloalkylsulfonyl:R.sup.7 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, cyano-C.sub.1 -C.sub.4 -alkyl, hydroxy-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, cyano-C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -haloalkenyl, C.sub.3 -C.sub.6 -alkynyl, cyano-C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -haloalkynyl, 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.3 -C.sub.4 -alkenyloxy-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkynyloxy-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.8 -cycloalkyloxy-C.sub.1 -C.sub.4 -alkyl, amino-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylamino-C.sub.1 -C.sub.4 -alkyl, di(C.sub.1 -C.sub.4 -alkyl)amino-C.sub.1 -C.sub.C.sub.4 -alkyl, 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 -alkyl, C.sub.3 -C.sub.4 -alkenylthio-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkynylthio-C.sub.1 -C.sub.4,-alkyl, C.sub.1 -C.sub.4 -alkylsulfinyl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.C.sub.4 -haloalkylsulfinyl-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenyl-sulfinyl-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.1 -alkynylsulfinyl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylsulfonyl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.1 -haloalkyl- sulfonyl-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkeny/sulfonyl-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkynylsulfonyl-C.sub.1 -C.sub.4 -alkyl, hydroxycarbonyl-C.sub.1 -C.sub.4 -alkyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl-C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by a cyano or (C.sub.1 -C.sub.4 -alkoxy)carbonyl group, (C.sub.1 -C.sub.4 -alkylthio)carbonyl-C.sub.1 -C.sub.4 -alkyl, aminocarbonyl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alklamino-carbonyl-C.sub.1 -C.sub.C.sub.4 -alkyl, di(C.sub.1 -C.sub.4 -alkyl)aminocarbonyl-C.sub.1 -C.sub.4 -akyl, di(C.sub.1 -C.sub.4 -alkyl)phosphonyl-C.sub.1 -C.sub.4 -alkl, (C.sub.1 -C.sub.4 -alkoyl)imino-C.sub.1 -C.sub.4 -alkyl, (C.sub.3 -C.sub.4 -alkenyloxy)imino-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl; phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl, 3- to 7-membered heterocyclyl or heterocyclyl-C.sub.1 -C.sub.4 -alkyl; where each cycloalkyl, phenyl and heterocyclyl ring in the definitions of R.sup.6 and R.sup.7 is unsubstituted or substituted by one to four substituents selected in each case from the group consisting of cyano, nitro, amino, hydroxyl, carboxyl, 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 -haloalkylthio, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -haloalkylsuffonyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl, (C.sub.1 -C.sub.4 -alkyl)carbonyl, (C.sub.1 -C.sub.4 -haloalkyl)carbonyl, (C.sub.1 -C.sub.4 -alkyl)carbonyloxy, (C.sub.1 -C.sub.4 -haloalkyl)carbonyloxy and di(C.sub.1 -C.sub.4 -alkyl)amino; or R.sup.6 and R.sup.7 together are a 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain which is unsubstituted or substituted by one to four C.sub.1 -C.sub.4 -alkyl groups or one or two (C.sub.1 -C.sub.4 -alkoxy)carbonyl groups, or the agriculturally useful salts of these compounds.