Pyrimidinone derivatives and herbicides containing them

A pyrimidinone derivative of the general formula:

• wherein:
• R1 is hydrogen or C1-C3 alkyl;
• R2 is C1-C3 haloalkyl;
• R3 is nitrogen or CH;
• G is any group of the general formula:
• wherein:
• E1, E2, E3, E4, E5, E6, E7, E8, E9, E10, E11, and E12 are independently hydrogen or C1-C3 alkyl;
• and
• Q is any group of the general formula:
• wherein:
• X is hydrogen or halogen;
• Y is halogen, nitro, cyano, or trifluoromethyl;
• Z1 is oxygen, sulfur, NH, or CH2;
• n is 0 or 1;
• R4 is hydrogen or C1-C3 alkyl;
• R3 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, (C3-C8 cycloalkyl) C1-C6 alkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, C1-C4 alkoxy C1-C4 alkyl, C1-C3 alkoxy C1-C3 alkoxy C1-C3 alkyl, carboxy C1-C6 alkyl, (C1-C6 alkoxy)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkoxy}carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, C1-C4 alkylthio C1-C4 alkyl, hydroxy C1-C6 alkyl, —CH2CON(R12)R13, —CH2COON(R12)R13,—CH(C1-C4 alkyl)CON(R12)R13, or —CH(C1-C4 alkyl)COON(R12)R13,
• wherein:
• R12 and R13 are independently hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, cyano C1-C6 alkyl, C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, carboxy C1-C6 alkyl, (C1-C6 alkoxy) carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, (C1-C6 alkyl)carbonyloxy C2-C6 alkyl, (C1-C6 alkyl)carbonylamino C2-C6 alkyl, hydroxy C2-C6 alkyl, optionally substituted benzyl, optionally substituted phenyl, or {(C1-C4 alkoxy) C1-C4 alkyl}carbonyl C1-C6 alkyl, or R12 and R13 are taken together to form trimethylene, tetramethylene, pentamethylene, ethyleneoxyethylene, or ethylenethioethylene;
• and
• B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR10, SR10, SO2OR21, N(R12)R13, SO2N(R12)R13,NR12(COR9), NR12(SO2R28), N(SO2R28)(SO2R29), N(SO2R28)(COR9), NHCOOR11, CONR12R13, CSNR12R13,COR30, CR23═CR24COR30, CR23═CR24CON(R12)R13, CH2CHWCON(R12)R13,CR30═NOR31, CR30═NN(R12)R13,CR30(Z2R32)2, OCO2R32, OCOR32, COOR22, CH2OR10, CR23═CR24COOR25, or CH2CHWCOOR25,
• wherein:
• R12 and R13 are as defined above;
• W is hydrogen, chlorine, or bromine;
• Z2 is oxygen or sulfur;
• R9 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, or C3-C6 alkenyl;
• R11 is hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, or C3-C6 alkenyl;
• R28 and R29 are independently C1-C6 alkyl, C1-C6 haloalkyl, or phenyl;
• R30 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, or C3-C6 alkynyl;
• R31 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, cyano C1-C6 alkyl, C2-C8 alkoxyalkyl, C2-C8 alkylthioalkyl, carboxy C1-C6 alkyl, (C1-C6 alkoxy)carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)-carbonyl C1-C6 alkyl, or {(C1-C4 alkoxy) C1-C4 alkoxy}carbonyl C1-C6 alkyl;
• R32 is hydrogen, C1-C6 alkyl, C3-Cs cycloalkyl, or C3-C6 alkenyl;
• R10 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, benzyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, carboxy C1-C6 alkyl, (C1-C8 alkoxy)carbonyl C1-C6 alkyl, (C1-C6 haloalkoxy)-carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkoxy}carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, (C3-C8 cycloalkyl) C1-C6 alkoxycarbonyl C1-C6 alkyl, —CH2COON—(R12)R13, —CH(C1-C4 alkyl)COON(R12)R13, —CH2CON(R12)R13, —CH(C1-C4 alkyl)CON(R12)R13 (wherein R12 and R13 are as defined above), C2-C6 alkenyloxycarbonyl C1-C6 alkyl, C3-C6 haloalkenyloxycarbonyl C1-C6 alkyl, C3-C6 alkynyloxycarbonyl C1-C6 alkyl, C3-C6 haloalkynyloxycarbonyl C1-C6 alkyl, (C1-C6 alkylthio)carbonyl C1-C6 alkyl, (C1-C6 haloalkylthio)-carbonyl C1-C6 alkyl, (C3-C6 alkenylthio)carbonyl C1-C6 alkyl, (C3-C6 haloalkenylthio)carbonyl C1-C6 alkyl, (C3-C6 alkynylthio)carbonyl C1-C6 alkyl, (C3-C6 haloalkynylthio)carbonyl C1-C6 alkyl, (C3-C8 cycloalkylthio)carbonyl C1-C6 alkyl, (C3-C8 cyclohaloalkylthio)carbonyl C1-C6 alkyl, ((C3-C8 cycloalkyl) C1-C6 alkylthio)carbonyl C1-C6 alkyl, di(C1-C6 alkyl)C═NO carbonyl C1-C6 alkyl, (optionally substituted benzylthio)-carbonyl C1-C6 alkyl, (optionally substituted phenylthio)-carbonyl C1-C6 alkyl, hydroxy C2-C6 alkoxycarbonyl C1-C6 alkyl, (C1-C6 alkyl)carbonyloxy C2-C6 alkoxycarbonyl C1-C6 alkyl, (C1-C6 alkyl)carbonylamino C2-C6 alkoxycarbonyl C1-C6 alkyl, {(C1-C6 alkoxy)carbonyl C1-C6 alkyl}oxycarbonyl C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, C3-C8 cycloalkoxycarbonyl, C3-C6 alkenyloxycarbonyl, optionally substituted benzyloxycarbonyl, C1-C6 alkylcarbonyl, optionally substituted benzyloxycarbonyl C1-C6 alkyl, optionally substituted phenoxycarbonyl C1-C6 alkyl, optionally substituted furyloxycarbonyl C1-C6 alkyl, optionally substituted furyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted thienyloxycarbonyl C1-C6 alkyl, optionally substituted thienyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted pyrrolyloxycarbonyl C1-C6 alkyl, optionally substituted pyrrolyloxy C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted imidazoyloxycarbonyl C1-C6 alkyl, optionally substituted imidazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted pyrazoyloxycarbonyl C1-C6 alkyl, optionally substituted pyrazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted thiazoyloxycarbonyl C1-C6 alkyl, optionally substituted thiazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted oxazoyloxycarbonyl C1-C6 alkyl, optionally substituted oxazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted isothiazoyloxycarbonyl C1-C6 alkyl, optionally substituted isothiazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted isoxazoyloxycarbonyl C1-C6 alkyl, optionally substituted isoxazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted pyridyloxycarbonyl C1-C6 alkyl, optionally substituted pyridyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted pyradinyloxycarbonyl C1-C6 alkyl, optionally substituted pyradinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted pyriaidinyloxy carbonyl C1-C6 alkyl, optionally substituted pyrimidinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted pyridazinyloxycarbonyl C1-C6 alkyl, optionally substituted pyridazinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted indolidinyloxycarbonyl C1-C6 alkyl, optionally substituted indolidinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted indolyloxycarbonyl C1-C6 alkyl, optionally substituted indolyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted indazolyloxycarbonyl C1-C6 alkyl, optionally substituted indazolyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted quinolyloxycarbonyl C1-C6 alkyl, optionally substituted quinolyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, optionally substituted isoquinolyloxycarbonyl C1-C6 alkyl, or optionally substituted isoquinolyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, or a group of the general formula:
• wherein:
• R14 is hydrogen or C1-C5 alkyl;
• and
• R15 is hydrogen, hydroxyl, or a group of —O—COR16,
• wherein:
• R16 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C8 cycloalkyl, optionally substituted phenyl, optionally substituted benzyl, or C1-C6 alkoxy;
• or a group of the general formula:
• wherein:
• R17 is hydrogen, halogen, or C1-C6 alkyl;
• and
• R18 is C3-C8 cycloalkyl, benzyl, C2-C10 alkyl with an epoxy group, C3-C8 cycloalkyl C1-C6 alkyl, C3-C8 cycloalkyl C2-C6 alkenyl, carboxy C2-C6 alkenyl, (C1-C8 alkoxy)carbonyl C2-C6 alkenyl, (C1-C8 haloalkoxy)carbonyl C2-C6 alkenyl, {(C1-C4 alkoxy) C1-C4 alkoxy}carbonyl C2-C6 alkenyl, (C3-C8 cycloalkoxy)-carbonyl C2-C6 alkenyl, C1-C6 alkyl substituted with OR19 and OR20 on the same carbon atom, C2-C6 alkenyl substituted with OR19 and OR20 on the same carbon atom, C1-C6 alkyl substituted with SR19 and SR20 on the same carbon atom, or C2-C6 alkenyl substituted with SR19 and SR20 on the same carbon atom,
• wherein:
• R19 and R20 are independently C1-C6 alkyl, C1-C6 haloalkyl, or R19 and R20 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;
• R21 is C1-C6 alkyl, C1-C6 haloalkyl, C3-Cs cycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, or benzyl;
• R22 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, benzyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, carboxy C1-C6 alkyl, (C1-C8 alkoxy)carbonyl C1-C6 alkyl, (C1-C6 haloalkoxy)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkoxy}carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, (C1-C6 alkyl)-carbonyl C1-C6 alkyl, (C1-C6 haloalkyl)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkyl}carbonyl C1-C6 alkyl, (C3-C8 cycloalkyl)carbonyl C1-C6 alkyl, {(C1-C6 alkoxy)carbonyl C1-C6 alkyl}oxycarbonyl C1-C6 alkyl, hydroxy C1-C6 alkyl, —CH2-COON(R26)R27, —CH(C1-C4 alkyl) COON(R26)R27, —CH2CON—(R26)R27, or —CH(C1-C4 alkyl)CON(R26)R27,
• wherein:
• R26 and R27 are independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, cyano C1-C6 alkyl, C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, carboxy C1-C6 alkyl, (C1-C6 alkoxy)carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)-carbonyl C1-C6 alkyl, or {(C1-C4 alkoxy) C1-C4 alkyl}-carbonyl C1-C6 alkyl, or R26 and R27 are taken together to form tetramethylene, pentamethylene, or ethyleneoxyethylene;
• R23 and R24 are independently hydrogen or C1-C6 alkyl;
• and
• R25 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, or C3-C6 alkenyl.