Patent ID: 6326333
Filing Date: 2001-12-04
Classification: A01N,C07D,C07F

Abstract:
A pyrazolyldioxothiochromanoyl derivative of the formula I ##STR21##where:X is oxygen, sulfur, S.dbd.O, S(.dbd.O).sub.2, CR.sup.4 R.sup.5, C.dbd.O or C.dbd.NR.sup.6 ;R.sup.1 is hydrogen, nitro, halogen, cyano, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.1 -C.sub.6 -alkylsulfinyl, C.sub.1 -C.sub.6 -haloalkylsulfinyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -haloalkylsulfonyl, aminosulfonyl, N-(C.sub.1 -C.sub.6 -alkyl)aminosulfonyl, N,N-di(C.sub.1 -C.sub.6 -alkyl)aminosulfonyl, N-(C.sub.1 -C.sub.6 -alkylsulfonyl)amino, N-(C.sub.1 -C.sub.6 -haloalkylsulfonyl)amino, N-(C.sub.1 -C.sub.6 -alkyl)-N-(C.sub.1 -C.sub.6 -alkylsulfonyl)amino or N-(C.sub.1 -C.sub.6 -alkyl)-N-(C.sub.1 -C.sub.6 -haloalkylsulfonyl)amino;R.sup.2 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -haloalkoxy;R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl or halogen;R.sup.4,R.sup.5 are hydrogen, nitro, halogen, cyano, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.1 -C.sub.6 -alkylsulfinyl, C.sub.1 -C.sub.6 -haloalkylsulfinyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -.sub.6 -haloalkylsulfonyl, N-C.sub.1 -C.sub.6 -alkylamino, N-C.sub.1 -C.sub.6 -haloalkylamino, N,N-di(C.sub.1 -C.sub.6 -alkyl)amino, N-C.sub.1 -C.sub.6 -alkoxyamino, N-(C.sub.1 -C.sub.6 -alkoxy)-N-(C.sub.1 -C.sub.6 -alkyl)amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl; orR.sup.4 and R.sup.5 together form an --O--(CH.sub.2).sub.m --O--, --O--(CH.sub.2).sub.m --S--, --S--(CH.sub.2).sub.m --S-- or --O--(CH.sub.2).sub.n -- chain which may be substituted by one to three radicals selected from the following group: halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -alkoxycarbonyl; orR.sup.4 and R.sup.5 together form a --(CH.sub.2).sub.p -- chain which may be interrupted by oxygen or sulfur and/or may be substituted by one to four radicals selected from the following group: halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -alkoxycarbonyl; orR.sup.4 and R.sup.5 together form a methylidene group which may be substituted by one or two radicals selected from the following group: halogen, cyano, hydroxyl, formyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.1 -C.sub.6 -alkylsulfinyl, C.sub.1 -C.sub.6 -haloalkylsulfinyl, C.sub.1 -C.sub.6 -alkylsulfonyl or C.sub.1 -C.sub.6 -haloalkylsulfonyl;R.sup.6 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -haloalkoxy;l is 0 to 4;m is 2 to 4;n is 1 to 5;p is 2 to 5;R.sup.7 is a compound IIa or IIb ##STR22##whereR.sup.8 is halogen, OR.sup.11, SR.sup.11, SOR.sup.12, SO.sub.2 R.sup.12, POR.sup.12 R.sup.13, OPOR.sup.12 R.sup.13, OPSR.sup.12 R.sup.13, NR.sup.14 R.sup.15, ONR.sup.15 R.sup.15, N-bonded heterocyclyl or O-(N-bonded heterocyclyl), where the heterocyclyl radical of the two lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, 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;R.sup.9 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, hydroxyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -haloalkoxy;R.sup.10 is hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, hydroxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio or C.sub.1 -C.sub.6 -haloalkylthio;R.sup.11 is 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, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.20 -alkylcarbonyl, C.sub.2 -C.sub.20 -alkenylcarbonyl, C.sub.2 -C.sub.6 -alkynylcarbonyl, C.sub.3 -C.sub.6 -cycloalkylcarbonyl, (2-norbornyl)methylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl, C.sub.3 -C.sub.6 -alkynyloxycarbonyl, C.sub.1 -C.sub.6 -alkylthiocarbonyl, C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.3 -C.sub.6 -alkenylaminocarbonyl, C.sub.3 -C.sub.6 -alkynylaminocarbonyl, N,N-di(C.sub.1 -C.sub.6 -alkyl)aminocarbonyl, N-(C.sub.3 -C.sub.6 -alkenyl)-N-(C.sub.1 -C.sub.6 -alkyl)aminocarbonyl, N-(C.sub.3 -C.sub.6 alkynyl)-N-(C.sub.1 -C.sub.6 -alkyl)aminocarbonyl, N-(C.sub.1 -C.sub.6 -alkoxy)-N-(C.sub.1 -C.sub.6 -alkyl)aminocarbonyl, N-(C.sub.3 -C.sub.6 alkenyl )-N-(C.sub.1 -C.sub.6 -alkoxy)aminocarbonyl, N-(C.sub.3 -C.sub.6 -alkynyl)-N-(C.sub.1 -C.sub.6 -alkoxy)aminocarbonyl, di(C.sub.1 -C.sub.6 alkyl)aminothiocarbonyl, C.sub.1 -C.sub.6 -alkylcarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxyamino-C.sub.1 -C.sub.6 -alkyl, N-(C.sub.1 -C.sub.6 -alkylamino)imino-C.sub.1 -C.sub.6 -alkyl or N,N-di(C.sub.1 -C.sub.6 -alkylamino)imino-C.sub.1 -C.sub.6 -alkyl, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, di(C.sub.1 -C.sub.4 -alkyl)amino, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkoxycarbonyl, di(C.sub.1 -C.sub.4 -alkyl)amino-C.sub.1 -C.sub.4 -alkoxycarbonyl, hydroxycarbonyl, C.sub.1 -C.sub.4 -alkylaminocarbonyl, di(C.sub.1 -C.sub.4 -alkyl)aminocarbonyl, aminocarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy or C.sub.3 -C.sub.6 -cycloalkyl;is phenyl, heterocyclyl, phenyl-C.sub.1 -C.sub.6 -alkyl, heterocyclyl-C.sub.1 -C.sub.6 -alkyl, phenylcarbonyl-C.sub.1 -C.sub.6 -alkyl, heterocyclylcarbonyl-C.sub.1 -C.sub.6 -alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, phenylaminocarbonyl, N-(C.sub.1 -C.sub.6 -alkyl)-N-(phenyl)aminocarbonyl, heterocyclylaminocarbonyl, N-(C.sub.1 -C.sub.6 -alkyl)-N-(heterocyclyl)aminocarbonyl, phenyl-C.sub.2 -C.sub.6 -alkenylcarbonyl or heterocyclyl-C.sub.2 -C.sub.6 -alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, 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, phenoxy, heterocyclyl or N-bonded heterocyclyl, where the three lastmentioned substituents for their part may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, 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;R.sup.12, R.sup.13 are 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, C.sub.3 -C.sub.6 -cycloalkyl, hydroxyl, C.sub.1 -C.sub.6 -alkoxy, amino, C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -haloalkylamino, di(C.sub.1 -C.sub.6 -alkyl)amino or di(C.sub.1 -C.sub.6 -haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, di(C.sub.1 -C.sub.4 -alkyl)amino, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkoxycarbonyl, di(C.sub.1 -C.sub.4 -alkyl)amino-C.sub.1 -C.sub.4 -alkoxycarbonyl, hydroxycarbonyl, C.sub.1 -C.sub.4 -alkylaminocarbonyl, di(C.sub.1 -C.sub.4 -alkyl)aminocarbonyl, aminocarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy or C.sub.3 -C.sub.6 -cycloalkyl;are phenyl, heterocyclyl, phenyl-C.sub.1 -C.sub.6 -alkyl, heterocyclyl-C.sub.1 -C.sub.6 -alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, 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;R.sup.14 is 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, C.sub.3 -C.sub.6 -cycloalkyl, hydroxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, amino, C.sub.1 -C.sub.6 -alkylamino, di(C.sub.1 -C.sub.6 -alkyl)amino or C.sub.1 -C.sub.6 -alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals of the following group: cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, di(C.sub.1 -C.sub.4 -alkyl)amino, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkoxycarbonyl, di(C.sub.1 -C.sub.4 -alkyl)amino-C.sub.1 -C.sub.4 -alkoxycarbonyl, hydroxycarbonyl, C.sub.1 -C.sub.4 -alkylamino-carbonyl, di(C.sub.1 -C.sub.4 -alkyl)aminocarbonyl, aminocarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy or C.sub.3 -C.sub.6 -cycloalkyl;is phenyl, heterocyclyl, phenyl-C.sub.1 -C.sub.6 -alkyl or heterocyclyl-C.sub.1 -C.sub.6 -alkyl, where the phenyl or heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, 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;R.sup.15 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.1 -C.sub.6 -alkylcarbonyl;and agriculturally useful salts thereof.