Production pyridazine herbicides

A carboxylic acid ester of formula (1):

• wherein R is C1-C6 alkyl, R2 and R3 are independently hydrogen or C1-C3 alkyl, and Q is Q-1, Q-2, Q-3, Q-4 or Q-5 of formula (2):
• wherein X is hydrogen or halogen;
• Y is halogen, nitro, cyano or trifluoromethyl;
• Z1 and Z2 are independently oxygen or sulfur;
• n is 0 or 1;
• R4 is hydrogen or C1-C3 alkyl;
• R5 is C1-C6 alkyl, C1-C6 haloalkyl, (C3-C6 cycloalkyl) C1-C6 alkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkenyl, 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, —CH2CON(R12)R13, —CH2COON(R12)R13, —CH(C1-C4 alkyl)CON(R12)R13, —CH(C1-C4 alkyl)COON(R12)R13,C1-C4 alkylthio C1-C4 alkyl or hydroxy C1-C6 alkyl;
• 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, benzyl, 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;
• R6 is C1-C6 alkyl, C1-C6 haloalkyl, cyano, carboxyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl, (C1-C6 alkyl)carbonyloxy C1-C6 alkyl, (C1-C6 haloalkyl)carbonyloxy C1-C6 alkyl or (C1-C6 alkoxy)carbonyl;
• R7 is hydrogen or C1-C6 alkyl;
• R8 is C1-C6 alkyl, C1-C6 haloalkyl, hydroxy C1-C6 alkyl, C1-C4 alkoxy C1-C4 alkyl, C1-C3 alkoxy C1-C3 alkoxy C1-C3 alkyl, (C1-C6 alkyl)carbonyloxy C1-C6 alkyl, (C1-C6 haloalkyl)carbonyl C1-C6 alkyl, carboxyl, carboxy C1-C6 alkyl, (C1-C8 alkoxy)carbonyl, (C1-C6 haloalkoxy)carbonyl, (C3-C10 cycloalkoxy)carbonyl, (C3-C8 alkenyloxy)carbonyl, (C3-C8 alkynyloxy)carbonyl, (C1-C6 alkyl)aminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkyl)amninocarbonyloxy C1-C6 alkyl or di(C1-C6 alkyl)aminocarbonyloxy C1-C6 alkyl;
• B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR1, SR1, SO2OR21, COOR22, CR23═CR24COOR25 or CH2CHWCOOR25;
• W is hydrogen, chlorine or brornine;
• R1 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, benzyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkenyl, 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, 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, benzylthio)carbonyl C1-C6 alkyl, 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, benzyloxycarbonyl, C1-C6 alkylcarbonyl, benzyloxycarbonyl C1-C6 alkyl, phenoxycarbonyl C1-C6 alkyl, furyloxycarbonyl C1-C6 alkyl,furyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, thienyloxycarbonyl C1-C6 alkyl, thienyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, pyrrolyloxycarbonyl C1-C6 alkyl, pyrrolyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, imidazoyloxycarbonyl C1-C6 alkyl, imidazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, pyrazoyloxycarbonyl C1-C6 alkyl, pyrazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, thiazoyloxycarbonyl C1-C6 alkyl, thiazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, oxazoyloxycarbonyl C1-C6 alkyl, oxazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, isothiazoyloxycarbonyl C1-C6 alkyl, isothiazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, isoxazoyloxycarbonyl C1-C6 alkyl, isoxazoyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, pyridyloxycarbonyl C1-C6 alkyl, pyridyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, pyrazinyloxycarbonyl C1-C6 alkyl, pyrazinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, pyrimidinyloxycarbonyl C1-C6 alkyl, pyrimidinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, pyridazinyloxycarbonyl C1-C6 alkyl, pyridazinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, indolidinyloxycarbonyl C1-C6 alkyl, indolidinyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, indolyloxycarbonyl C1-C6 alkyl, indolyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, indazolyloxycarbonyl C1-C6 alkyl, indazolyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, quinolyloxycarbonyl C1-C6 alkyl, quinolyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, isoquinolyloxycarbonyl C1-C6 alkyl, isoquinolyl C1-C6 alkyloxycarbonyl C1-C6 alkyl, or a group of formula (3):
• wherein R14 is C1-C5 alkyl;
• R15 is hydrogen, hydroxyl or a group of —O—COR16;
• R16 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C8 cycloalkyl, phenyl, benzyl or C1-C6 alkoxy, or a group of formula (4):
• wherein R17 is hydrogen, halogen or C1-C6 alkyl;
• 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, 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, C2-C6 alkenyl substituted with SR19 and SR20 on the same carbon atom, carboxy C2-C6 alkenyl, (C1-C8 alkoxy)carbonyl C2-C6 alkenyl, (C1-C8 haloalkoxy)carbonyl C2-C6 alkenyl, {(C1-C4 alkoxy) C2-C4 alkoxy}carbonyl C2-C6 alkenyl or (C3-C8 cycloalkoxy)carbonyl C2-C6 alkenyl:
• R19 and R20 are independently C1-C6 alkyl or C1-C6 haloalkyl, or R19 and R20 are taken together with to form ethylene optionally substituted with halogen, trimethylene optionally substituted with halogen, tetramethylene optionally substituted with halogen, pentamethylene methylene optionally substituted with halogen, or ethyleneoxyethylene optionally substituted with halogen;
• R21 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkenyl 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 haloalkenyl, 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 C1C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkyl}carbonyl C1-C6 alkyl, (C3-C8 cycloalkyl)carbonyl C1-C6 alkyl, —CH2COON(R26)R27, —CH(C1-C4 alkyl)COON(R26)R27, —CH2CON(R26)R27—CH(C1-C4 alkyl)CON(R26)R27, {(C1-C6 alkoxy)carbonyl C1-C6 alkyl}oxycarbonyl C1-C6 alkyl or hydroxy C1-C6 alkyl;
• 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, halogen or C1-C6 alkyl;
• and
• R25 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl or C3-C6 alkenyl.