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US 6,143,696 AGranted
Substituted 4-(3-alkenylbenzoyl)pyrazoles
AssigneeBASF SE
InventorsErnst Baumann, Wolfgang von Deyn, Stefan Engel, Regina Luise Hill, Uwe Kardorff, Guido Mayer, Martina Otten, Michael Rack, Joachim Rheinheimer, Matthias Witschel, Karl-Otto Westphalen, Ulf Misslitz, Helmut Walter
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Abstract
4-(3-Alkenylbenzoyl)pyrazoles of the formula I ##STR1## and agriculturally useful salts thereof; processes for preparing the compounds of the formula I; compositions comprising them; and the use of these derivatives or of compositions comprising them for controlling undesirable plants.
Claims9
4-(3-Alkenylbenzoyl)pyrazoles of the formula I ##STR702## where:
- R.sup.1 and R.sup.2 are each hydrogen, nitro, halogen, cyano, thiocyanato, 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 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, --OR.sup.6, --OCOR.sup.7, --OSO.sub.2 R.sup.7, --SH, --S(O).sub.n R.sup.8, --SO.sub.2 OR.sup.6, --SO.sub.2 NR.sup.6 R.sup.9, --NR.sup.9 SO.sub.2 R.sup.7 or --NR.sup.9 COR.sup.7 ;
- R.sup.3 is hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl;
- R.sup.4 and R.sup.5 are each hydrogen, nitro, halogen, cyano, thiocyanato, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.4 -C.sub.6 -cycloalkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkoxy, --COR.sup.10, --CO.sub.2 R.sup.11, --COSR.sup.10, --CONR.sup.10 R.sup.11, --C(R.sup.12).dbd.NR.sup.13, --PO(OR.sup.10)(OR.sup.11), C.sub.1 -C.sub.4 -alkyl which carries a radical from the following group:
- hydroxyl, --COR.sup.10, --CO.sub.2 R.sup.10, --COSR.sup.10, --CONR.sup.10 R.sup.11 or --C(R.sup.12).dbd.NR.sup.13 ;
- heterocyclyl, heterocyclyl-C.sub.1 -C.sub.4 -alkyl (where the heterocyclyl radical of the two last-mentioned radicals is three- to seven-membered, saturated or partially unsaturated, mono- or polycyclic and contains one to three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur), phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl, hetaryl or hetaryl-C.sub.1 -C.sub.4 -alkyl (where the hetaryl radical of the two last-mentioned radicals is aromatic, mono- or polycyclic and may, in addition to carbon ring members, additionally contain one to 4 nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom), it being possible for the last six radicals to be substituted;
- or
- R.sup.4 and R.sup.5 together form a C.sub.2 -C.sub.6 -alkanediyl chain which may be mono- to tetrasubstituted by C.sub.1 -C.sub.4 -alkyl and/or interrupted by oxygen or sulfur or by nitrogen with or without substitution by C.sub.1 -C.sub.4 -alkyl;
- n is 0, 1 or 2;
- R.sup.6 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.2 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl;
- R.sup.7 is C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl;
- R.sup.8 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.2 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl;
- R.sup.9 is hydrogen or C.sub.1 -C.sub.6 -alkyl;
- R.sup.10 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, phenyl or benzyl, it being possible for the last two radicals to be partially or fully halogenated and/or to carry one to three radicals from the following group:
- 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, C.sub.1 -C.sub.4 -alkylcarbonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl;
- R.sup.11 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl;
- or
- R.sup.10 and R.sup.11 together form a C.sub.2 -C.sub.6 -alkanediyl chain which may be mono- to tetrasubstituted by C.sub.1 -C.sub.4 -alkyl and/or interrupted by oxygen or sulfur or by nitrogen with or without substitution by C.sub.1 -C.sub.4 -alkyl;
- R.sup.12 is hydrogen, 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 -alkoxycarbonyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, phenyl or benzyl, it being possible for the last two radicals to be partially or fully halogenated and/or to carry one to three radicals of the following group:
- 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, C.sub.1 -C.sub.4 -alkylcarbonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl;
- R.sup.13 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.3 -C.sub.6 -cycloalkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, phenyl, benzyl or phenyl-C.sub.1 -C.sub.4 -alkoxy, it being possible for the last three radicals to be partially or fully halogenated and/or to carry one to three radicals from the following group:
- 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, C.sub.1 -C.sub.4 -alkylcarbonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl;
- Q is a pyrazole of the formula II ##STR703## which is linked in position 4 and where R.sup.14 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, phenyl or phenyl which is partially or fully halogenated and/or carries 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;
- R.sup.15 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -haloalkylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -haloalkylsulfonyl, phenyl-C.sub.1 -C.sub.4 -alkyl, phenylcarbonyl, phenylcarbonylmethyl, phenoxycarbonyl or phenylsulfonyl, the last five substituents being unsubstituted or the phenyl ring in question being partially or fully halogenated and/or carrying 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;
- R.sup.16 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl;
- and agriculturally useful salts thereof.
24 more elements
Dependencies are inferred from the claim text.