Patent ID: 6191070
Filing Date: 2001-02-20
Classification: A01N,C07D

Abstract:
A pyrimidinone derivative of the general formula: ##STR78##wherein:R.sup.1 is hydrogen or C.sub.1 -C.sub.3 alkyl;R.sup.2 is C.sub.1 -C.sub.3 haloalkyl;R.sup.3 is nitrogen or CH;G is any group of the general formula: ##STR79##wherein:E.sup.1, E.sup.2, E.sup.3, E.sup.4, E.sup.5, E.sup.6, E.sup.7, E.sup.8, E.sup.9, E.sup.10, E.sup.11, and E.sup.12 are independently hydrogen or C.sub.1 -C.sub.3 alkyl; andQ is any group of the general formula: ##STR80##wherein:X is hydrogen or halogen;Y is halogen, nitro, cyano, or trifluoromethyl;Z.sup.1 is oxygen, sulfur, NH, or CH.sub.2 ;n is 0 or 1;R.sup.4 is hydrogen or C.sub.1 -C.sub.3 alkyl;R.sup.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, (C.sub.3 -C.sub.8 cycloalkyl) C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, cyano C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy C.sub.1 -C.sub.3 alkoxy C.sub.1 -C.sub.3 alkyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkoxy}carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, hydroxy C.sub.1 -C.sub.6 alkyl, --CH.sub.2 CON(R.sup.12)R.sup.13, --CH.sub.2 COON(R.sup.12)R.sup.13,--CH(C.sub.1 -C.sub.4 alkyl)CON(R.sup.12)R.sup.13, or --CH(C.sub.1 -C.sub.4 alkyl)COON(R.sup.12)R.sup.13,wherein:R.sup.12 and R.sup.13 are independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, cyano C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkoxy) carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyloxy C.sub.2 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonylamino C.sub.2 -C.sub.6 alkyl, hydroxy C.sub.2 -C.sub.6 alkyl, optionally substituted benzyl, optionally substituted phenyl, or {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkyl}carbonyl C.sub.1 -C.sub.6 alkyl, or R.sup.12 and R.sup.13 are taken together to form trimethylene, tetramethylene, pentamethylene, ethyleneoxyethylene, or ethylenethioethylene; andB is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR.sup.10, SR.sup.10, SO.sub.2 OR.sup.21, N(R.sup.12)R.sup.13, SO.sub.2 N(R.sup.12)R.sup.13,NR.sup.12 (COR.sup.9), NR.sup.12 (SO.sub.2 R.sup.28), N(SO.sub.2 R.sup.28)(SO.sub.2 R.sup.29), N(SO.sub.2 R.sup.28)(COR.sup.9), NHCOOR.sup.11, CONR.sup.12 R.sup.13, CSNR.sup.12 R.sup.13,COR.sup.30, CR.sup.23.dbd.CR.sup.24 COR.sup.30, CR.sup.23.dbd.CR.sup.24 CON(R.sup.12)R.sup.13, CH.sub.2 CHWCON(R.sup.12)R.sup.13,CR.sup.30.dbd.NOR.sup.31, CR.sup.30.dbd.NN(R.sup.12)R.sup.13,CR.sup.30 (Z.sup.2 R.sup.32).sub.2, OCO.sub.2 R.sup.32, OCOR.sup.32, COOR.sup.22, CH.sub.2 OR.sup.10, CR.sup.23.dbd.CR.sup.24 COOR.sup.25, or CH.sub.2 CHWCOOR.sub.25,wherein:R.sup.12 and R.sup.13 are as defined above;W is hydrogen, chlorine, or bromine;Z.sup.2 is oxygen or sulfur;R.sup.9 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.8 cycloalkyl, or C.sub.3 -C.sub.6 alkenyl;R.sup.11 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl, or C.sub.3 -C.sub.6 alkenyl;R.sup.28 and R.sup.29 are independently C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, or phenyl;R.sup.30 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, or C.sub.3 -C.sub.6 alkynyl;R.sup.31 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, cyano C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.2 -C.sub.8 alkylthioalkyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkoxy)-carbonyl C.sub.1 -C.sub.6 alkyl, or {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkoxy}carbonyl C.sub.1 -C.sub.6 alkyl;R.sup.32 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -Cs cycloalkyl, or C.sub.3 -C.sub.6 alkenyl;R.sup.10 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, cyano C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.8 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 haloalkoxy)-carbonyl C.sub.1 -C.sub.6 alkyl, {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkoxy}carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkyl) C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl, --CH.sub.2 COON--(R.sup.12)R.sup.13, --CH(C.sub.1 -C.sub.4 alkyl)COON(R.sup.12)R.sup.13, --CH.sub.2 CON(R.sup.12)R.sup.13, --CH(C.sub.1 -C.sub.4 alkyl)CON(R.sup.12)R.sup.13 (wherein R.sup.12 and R.sup.13 are as defined above), C.sub.2 -C.sub.6 alkenyloxycarbonyl C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 haloalkenyloxycarbonyl C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkynyloxycarbonyl C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 haloalkynyloxycarbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkylthio)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 haloalkylthio)-carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.6 alkenylthio)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.6 haloalkenylthio)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.6 alkynylthio)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.6 haloalkynylthio)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkylthio)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cyclohaloalkylthio)carbonyl C.sub.1 -C.sub.6 alkyl, ((C.sub.3 -C.sub.8 cycloalkyl) C.sub.1 -C.sub.6 alkylthio)carbonyl C.sub.1 -C.sub.6 alkyl, di(C.sub.1 -C.sub.6 alkyl)C.dbd.NO carbonyl C.sub.1 -C.sub.6 alkyl, (optionally substituted benzylthio)-carbonyl C.sub.1 -C.sub.6 alkyl, (optionally substituted phenylthio)-carbonyl C.sub.1 -C.sub.6 alkyl, hydroxy C.sub.2 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyloxy C.sub.2 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonylamino C.sub.2 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl, {(C.sub.1 -C.sub.6 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl}oxycarbonyl C.sub.1 -C.sub.6 alkyl, hydroxy C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 haloalkoxycarbonyl, C.sub.3 -C.sub.8 cycloalkoxycarbonyl, C.sub.3 -C.sub.6 alkenyloxycarbonyl, optionally substituted benzyloxycarbonyl, C.sub.1 -C.sub.6 alkylcarbonyl, optionally substituted benzyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted phenoxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted furyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted furyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted thienyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted thienyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyrrolyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyrrolyloxy C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted imidazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted imidazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyrazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyrazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted thiazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted thiazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted oxazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted oxazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted isothiazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted isothiazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted isoxazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted isoxazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyridyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyridyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyradinyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyradinyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyriaidinyloxy carbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyrimidinyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyridazinyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted pyridazinyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted indolidinyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted indolidinyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted indolyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted indolyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted indazolyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted indazolyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted quinolyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted quinolyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, optionally substituted isoquinolyloxycarbonyl C.sub.1 -C.sub.6 alkyl, or optionally substituted isoquinolyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, or a group of the general formula: ##STR81##wherein:R.sup.14 is hydrogen or C.sub.1 -C.sub.5 alkyl; andR.sup.15 is hydrogen, hydroxyl, or a group of --O--COR.sup.16,wherein:R.sup.16 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, optionally substituted phenyl, optionally substituted benzyl, or C.sub.1 -C.sub.6 alkoxy;or a group of the general formula: ##STR82##wherein:R.sup.17 is hydrogen, halogen, or C.sub.1 -C.sub.6 alkyl; andR.sup.18 is C.sub.3 -C.sub.8 cycloalkyl, benzyl, C.sub.2 -C.sub.10 alkyl with an epoxy group, C.sub.3 -C.sub.8 cycloalkyl C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl C.sub.2 -C.sub.6 alkenyl, carboxy C.sub.2 -C.sub.6 alkenyl, (C.sub.1 -C.sub.8 alkoxy)carbonyl C.sub.2 -C.sub.6 alkenyl, (C.sub.1 -C.sub.8 haloalkoxy)carbonyl C.sub.2 -C.sub.6 alkenyl, {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkoxy}carbonyl C.sub.2 -C.sub.6 alkenyl, (C.sub.3 -C.sub.8 cycloalkoxy)-carbonyl C.sub.2 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkyl substituted with OR.sup.19 and OR.sup.20 on the same carbon atom, C.sub.2 -C.sub.6 alkenyl substituted with OR.sup.19 and OR.sup.20 on the same carbon atom, C.sub.1 -C.sub.6 alkyl substituted with SR.sup.19 and SR.sup.20 on the same carbon atom, or C.sub.2 -C.sub.6 alkenyl substituted with SR.sup.19 and SR.sup.20 on the same carbon atom,wherein:R.sup.19 and R.sup.20 are independently C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, or R.sup.19 and R.sup.20 are taken together to form ethylene optionally substituted with halogen, trimethylene optionally substituted with halogen, tetramethylene optionally substituted with halogen, pentamethylene optionally substituted with halogen, or ethyleneoxyethylene optionally substituted with halogen;R.sup.21 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -Cs cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, or benzyl;R.sup.22 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, cyano C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.8 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 haloalkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkoxy}carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)-carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 haloalkyl)carbonyl C.sub.1 -C.sub.6 alkyl, {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkyl}carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkyl)carbonyl C.sub.1 -C.sub.6 alkyl, {(C.sub.1 -C.sub.6 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl}oxycarbonyl C.sub.1 -C.sub.6 alkyl, hydroxy C.sub.1 -C.sub.6 alkyl, --CH.sub.2 -COON(R.sup.26)R.sup.27, --CH(C.sub.1 -C.sub.4 alkyl) COON(R.sup.26)R.sup.27, --CH.sub.2 CON--(R.sup.26)R.sup.27, or --CH(C.sub.1 -C.sub.4 alkyl)CON(R.sup.26)R.sup.27,wherein:R.sup.26 and R.sup.27 are independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, cyano C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkoxy)-carbonyl C.sub.1 -C.sub.6 alkyl, or {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkyl}-carbonyl C.sub.1 -C.sub.6 alkyl, or R.sup.26 and R.sup.27 are taken together to form tetramethylene, pentamethylene, or ethyleneoxyethylene;R.sup.23 and R.sup.24 are independently hydrogen or C.sub.1 -C.sub.6 alkyl; andR.sup.25 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.8 cycloalkyl, or C.sub.3 -C.sub.6 alkenyl.