Patent ID: 6333413
Filing Date: 2001-12-25
Classification: C07C,C07D

Abstract:
A process for producing a pyridazin-3-one derivative of formula (7):##STR21##wherein R.sup.2 and R.sup.3 are independently hydrogen or C.sub.1 -C.sub.3 alkyl, and Q is optionally substituted phenyl comprising ring closing a compound of formula (1) at a temperature of 80.degree. to 250.degree. C., wherein formula (1) is:##STR22##wherein Q is Q-1, Q-2, Q-3, Q-4 or Q-5 of formula (2):##STR23##whereinX is hydrogen or halogen;Y is halogen, nitro, cyano or trifluoromethyl;Z.sup.1 and Z.sup.2 are independently oxygen or sulfur;n is 0 or 1;R.sup.4 is hydrogen or C.sub.1 -C.sub.3 alkyl;R.sup.5 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, (C.sub.3 -C.sub.6 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 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, --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, --CH(C.sub.1 -C.sub.4 alkyl)COON(R.sup.12)R.sup.13, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl or hydroxy C.sub.1 -C.sub.6 alkyl;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, benzyl, 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;R.sup.6 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, cyano, carboxyl, hydroxy C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyloxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 haloalkyl)carbonyloxy C.sub.1 -C.sub.6 alkyl or (C.sub.1 -C.sub.6 alkoxy)carbonyl;R.sup.7 is hydrogen or C.sub.1 -C.sub.6 alkyl;R.sup.8 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, hydroxy 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, (C.sub.1 -C.sub.6 alkyl)carbonyloxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 haloalkyl)carbonyl C.sub.1 -C.sub.6 alkyl, carboxyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.8 alkoxy)carbonyl, (C.sub.1 -C.sub.6 haloalkoxy)carbonyl, (C.sub.3 -C.sub.10 cycloalkoxy)carbonyl, (C.sub.3 -C.sub.8 alkenyloxy)carbonyl, (C.sub.3 -C.sub.8 alkynyloxy)carbonyl, (C.sub.1 -C.sub.6 alkyl)aminocarbonyl, di(C.sub.1 -C.sub.6 alkyl)aminocarbonyl, (C.sub.1 -C.sub.6 alkyl)aminocarbonyloxy C.sub.1 -C.sub.6 alkyl or di(C.sub.1 -C.sub.6 alkyl)aminocarbonyloxy C.sub.1 -C.sub.6 alkyl;B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR.sup.1, SR.sup.1, SO.sub.2 OR.sup.21, COOR.sup.22, CR.sup.23.dbd.CR.sup.24 COOR.sup.25 or CH.sub.2 CHWCOOR.sup.25 ;W is hydrogen, chlorine or bromine;R.sup.1 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 akyl)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, 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 -.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.3 alkenyloxycarbonyl, benzyloxycarbonyl, C.sub.1 -C.sub.6 alkylcarbonyl, benzyloxycarbonyl C.sub.1 -C.sub.6 alkyl, phenoxycarbonyl C.sub.1 -C.sub.6 alkyl, furyloxycarbonyl C.sub.1 -C.sub.6 alkyl, furyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, thienyloxycarbonyl C.sub.1 -C.sub.6 alkyl, thienyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyrrolyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyrrolyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, imidazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, imidazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyrazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyrazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, thiazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, thiazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, oxazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, oxazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, isothiazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, isothiazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, isoxazoyloxycarbonyl C.sub.1 -C.sub.6 alkyl, isoxazoyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyridyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyridyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyrazinyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyrazinyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyrimidinyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyrimidinyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyridazinyloxycarbonyl C.sub.1 -C.sub.6 alkyl, pyridazinyl C.sub.l -C.sub.6 alkyloxycarbonyl C.sub.l -C.sub.6 alkyl, indolidinyloxycarbonyl C.sub.1 -C.sub.6 alkyl, indolidinyl C.sub.l -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, indolyloxycarbonyl C.sub.1 -C.sub.6 alkyl, indolyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, indazolyloxycarbonyl C.sub.1 -C.sub.6 alkyl, indazolyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, quinolyloxycarbonyl C.sub.1 -C.sub.6 alkyl, quinolyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, isoquinolyloxycarbonyl C.sub.1 -C.sub.6 alkyl, isoquinolyl C.sub.1 -C.sub.6 alkyloxycarbonyl C.sub.1 -C.sub.6 alkyl, ora group of formula (3):##STR24##wherein R.sup.14 is C.sub.1 -C.sub.5 alkyl; R.sup.15 is hydrogen, hydroxyl or a group of --O--COR.sup.16 ; 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, phenyl, [optionally substituted] benzyl or C.sub.1 -C.sub.6 alkoxy, ora group of formula (4):##STR25##whereinR.sup.17 is hydrogen, halogen or C.sub.1 -C.sub.6 alkyl; R.sup.18 is C.sub.3 -C.sub.8 cycloalkyl, benzyl, C.sub.2 -C.sub.10 alkyl with an epoxide 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, 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, C.sub.2 -C.sub.6 alkenyl substituted with SR.sup.19 and SR.sup.20 on the same carbon atom, 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 or (C.sub.3 -C.sub.8 cycloalkoxy)carbonyl C.sub.2 -C.sub.6 alkenyl; R.sup.19 and R.sup.20 are independently C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 haloalkyl, or R.sup.19 and R.sup.20 are taken together with 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 -C.sub.8 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.6 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.l -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, --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, --CH--(C.sub.1 -C.sub.4 alkyl)CON(R.sup.26)R.sup.27, {(C.sub.1 -C.sub.6 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl}oxycarbonyl C.sub.1 -C.sub.6 alkyl or hydroxy C.sub.1 -C.sub.6 alkyl;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, halogen or C.sub.1.varies.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.