Substituted 2-phenylpyridines
First Claim
Patent Images
1. A substituted 2-phenylpridine of the formula I ##STR93## in which the variables have the following meanings:
- R1 hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C1 -C4 -alkoxy-C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, (C1 -C5 -alkyl)carbonyloxy, (C1 -C5 -haloalkyl)carbonyloxy, SH, C1 -C4 -alkylthio, C1 -C4 -alkylsulfinyl, C1 -C4 -alkylsulfonyl, C1 -C4 -haloalkylthio, C1 -C4 -haloalkylsulfinyl, C1 -C4 -haloalkylsulfonyl, formyl, cyano, hydroxycarbonyl, (C1 -C4 -alkoxy) carbonyl, C1 -C4 -alkoxy(C1 -C4 -alkoxy)carbonyl, (C1 -C4 -haloalkoxy)carbonyl, (C1 -C4 -alkyl(carbonyl, (C1 -C4 -haloalkyl) carbonyl, C1 -C4 -alkoxy(C1 -C4 -alkyl)carbonyl, CONH2, (C1 -C4 -alkyl)aminocarbonyl, di-(C1 -C4 -alkyl)aminocarbonyl, pyrrolidinylcarbonyl, piperidinylcarbonyl morpholinylcarbonyl, nitro, amino, C1 -C4 -alkylamino, di-(C1 -C4 -alkyl)amino, pyrrolidinyl, piperidinyl, morpholinyl, (C1 -C4 -alkyl)carbonylamino, (C1 -C4 -haloalkyl)carbonylamino or C1 -C4 -alkylsulfonylamino;
R2 halogen, cyano, nitro, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, C1 -C4 -alkylthio, or C1 -C4 -haloalkylthio,or together with R1 or with R3 a trimethylene or tetramethylene chain;
R3 hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkoxy-C1 -C4 -alkoxy, hydroxyl, C1 -C4 -haloalkoxy, (C1 -C5 -alkyl)carbonyloxy, (C1 -C5 -haloalkyl)carbonyloxy, SH, C1 -C4 -alkylthio, C1 -C4 -alkylsulfinyl, C1 -C4 -alkylsulfonyl, C1 -C4 -haloalkylthio, C1 -C4 -haloalkylsulfinyl, C1 -C4 -haloalkylsulfonyl, formyl, cyano, hydroxycarbonyl, (C1 -C4 -alkoxy)carbonyl, C1 -C4 -alkoxy(C1 -C4 -alkoxy)carbonyl, (C1 -C4 -haloalkoxy)carbonyl, (C1 -C4 -alkyl)carbonyl, (C1 -C4 -haloalkyl)carbonyl, C1 -C4 -alkoxy-(C1 -C4 C-alkyl)carbonyl, CONH2, (C1 -C4 -alkyl)aminocarbonyl, di-(C1 -C4 -alkyl)aminocarbonyl, pyrrolidinylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, nitro, amino, C1 -C4 -alkylamino, di-(C1 -C4 -alkyl)amino, pyrrolidinyl, piperidinyl, morpholinyl, (C1 -C4 -alkyl)carbonylamino, (C1 -C4 -haloalkyl)carbonylamino or C1 -C4 -alkylsulfonylamino;
R4 halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkoxy, hydroxyl, C1 -C4 -haloalkoxy, (C1 -C5 -alkyl)carbonyloxy, (C1 -C5 -haloalkyl)carbonyloxy, SH, C1 -C4 -alkylthio, C1 -C4 -alkylsulfinyl, C1 -C4 -alkylsulfonyl, C1 -C4 -haloalkylthio, C1 -C4 -haloalkylsulfinyl, C1 -C4 -haloalkylsulfonyl, formyl, cyano, hydroxycarbonyl, (C1 -C4 -alkoxy)carbonyl, C1 -C4 -alkoxy-(C1 -C4 -alkoxy)carbonyl, (C1 -C4 -haloalkoxy)carbonyl, (C1 -C4 -alkyl)carbonyl, (C1 -C4 -haloalkyl)carbonyl, C1 -C4 -alkoxy-(C1 -C4 -alkyl)carbonyl, nitro, amino, C1 -C4 -alkylamino, di-(C1 -C4 -alkyl)amino, pyrrolidinyl, piperidinyl, morpholinyl, (C1 -C4 -alkyl)carbonylamino, (C1 -C4 -haloalkyl)carbonylamino or C1 -C4 -alkylsulfonylamino;
R5 is hydrogen or halogen;
R6 is halogen, cyano, nitro, hydroxyl, trifluoromethyl, C1 -C6 -alkyl or C1 -C4 -alkoxy;
R7 chlorine, bromine, iodine, cyano, nitro, C1 -C8 -alkyl, C2 -C8 -alkenyl, C2 -C8 -alkynyl, C1 -C8 -haloalkyl, C2 -C8 -haloalkenyl, C2 -C8 -haloalkynyl, --(C1 -C8 -alkylene)-O--R8, --(C2 -C8 -alkenylene)-O--R8 -alkenylene-S--R8, --C2 -C8 -alkenylene)-S--R8, --(C2 -C8 -alkylene)-S--R8, --C1 -C8 -alkylene)-SO--R8, --(C2 -C8 -alkenylene)-SO--R8, --(C2 -C8 -alkynylene)-SO--R8, --(C1 -C8 -alkylene)-SO2 --R8, --(C2 -C8 -alkenylene)-SO2 --R8, --(C2 -C8 -alkynylene)-SO2 --R8, --O--R8, --S--R8, --SO--R8, --SO2 --R8, chlorosulfonyl, --SO2 --O--R8, --SO2 --N(R9,R10), --SO2 --NR9 (CO--R12), --N(R9,R10), --NR11 (CO--R12), --NR11 (SO2 --R13), --N(SO2 --R13)(SO2 --R14), --N(SO2 --R13)(CO--R12), --NH--CO--O--R8, --O--CO--NHR9, --O--CO--R12, --NH--CO--NHR9, --O--CS--N(C1 -C4 -alkyl)2, --O--CS--NH2, cyano-C1 14 C4 -alkyl, --CO--R8, --CO--O--N═
C(R26,R27), --CO--O--CH2 --O--N═
C(R30,R31), --CO--O--C(R28,R29)--CH2 --ON═
C(R30,R31), --CO--N(R9,R10), --CS--N(R9,R10), --CO--NH--SO2 --(C1 -C4 -alkyl), isoxazolinylcarbonyl, formyl, --CO--R15, hydroxycarbonyl-C1 -C6 -alkyl, (C1 14 C6 -alkoxy)carbonyl-C1 -C6 -alkyl, --CR15 ═
C(R16)--CHO, --C(R15)═
C(R16)--CO--O--R8, --C(R15)═
C(R16)--CO--N(R9,R10), --C(R15)═
C(R16)--CO--R17, --CH═
N--O--R8, --CH(XR18,YR19), --CH2 --CH(halogen)-CO--O--R8, --CH2 --CH(halogen)-CO--N(R9,R10), --CH2 --CH(halogen)-CO--(C1 -C4 -alkyl), --CH2 --CH(halogen)-CN, --C(C1 -C4 -alkoxy)=N--O--R8, --C(R15)═
C(R16)--C(C1 -C4 -alkoxy)=N--O--R8, --CH═
CH--CH═
CH--CO--O--R8, ##STR94## --C(R15)═
N--O--R8, --CO--OCH═
N--OH, --CO--OCH═
N--O--(C1 -C4 alkyl), --CO--OC(C1 -C4 -alkyl)=N--OH, --CO--OC(C1 -C4 -alkyl)=N--O--(C1 -C4 -alkyl), --CO--O--(CO1 -C4 -alkylene)--CH═
N--OH, --CO--O--(C1 -C4 -alkylene)-CH═
N--O--(C1 -C4 -alkyl), --CO--O--(C1 -C4 -alkylene)-C(C1 -C4 -alkylene)-C(C11 -C4 -alkyl)=N--OH, --CO--O--(C1 -C4 -alkyl)=N--O--(C1 -C4 -alkyl), --(C1 -C8 -alkylene)-O--CO--(C1 -C4 -alkyl), --CH═
C═
CH2, --CH═
C═
CH--(C1 -C4 -alkyl), ##STR95## 5- or 6-membered heteroaryl with one to three hetero atoms selected from a group comprising one or two nitrogen atoms and one oxygen or sulfur atom, it being possible for each heteroaromatic ring atom which can be substituted to carry a radical selected from the group comprising nitro, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio and (C1 -C4 -alkoxy)carbonyl;
R8 hydrogen, C1 -C8 -alkyl, C1 -C8 -haloalkyl, C4 -C7 -cycloalkyl, which in turn can carry one to three C1 -C3 -alkyl radicals, C3 -C6 -alkenyl, C5 -C7 -cycloalkenyl, which in turn can carry one to three C1 -C3 -alkyl radicals, C3 -C6 -haloalkenyl, cyano-C1 -C8 -alkyl, C3 -C6 -alkynyl, C2 -C8 -alkoxyalkyl, 2-tetrahydrofuranyl-C1 -C8 -alkyl, 3-oxetanyl, 3-thietanyl, carboxyl-C1 -C6 -alkyl, (C1 -C8 -alkoxy) carbonyl-C1 -C6 -alkyl, (C1 -C6 -alkoxy)carbonyl-(C3 -C7 -cycloalkyl), C1 -C4 -alkoxy-(C1 -C4 -alkoxy)carbonyl-C1 -C6 -alkyl, cyclopropylmethyl, (1-methylthiocyclopropyl)methyl, --CH(SH)--CO--OH, --CH(SH)--CO--(C1 -C8 -alkoxy), --CH (C1 -C8 alkylthio)-COOH, --CH(C1 -C4 -alkylthio)-CO--(C1 -C8 -alkoxy), --CH2 --CO--N(R9)--R10, --CH(C1 -C4 -alkyl)-CO--N(R9)--R10, --(C1 -C4 -alkyl)2 --CO--N(R9)--R10, --CH2 --CO--N(9)--SO2 --(C1 -C4 -alkyl), --CH(C1 -C4 -alkyl)-CO--N(R9)--SO2 --C(C1 -C4 -alkyl)2 -CO--N(R9)--SO2 --(C1 -C4 -alkyl), --S--CO--NH2,--S--CO--N(C1 --alkyl)-(C1 -C4 -alkyl), CH2 --CO--O--(C1 -C6 -alkylene)-COOH, --CH2 --CO--O--(C1 -C6 -alkylene)-CO--(C1 -C6 -alkoxy), --C(C1 -C4 -alkyl)2 --CO--O--(C1 -C6 -alkylene)-COOH, --(C1 -C4 -alkyl)2 --CO--O--(C1 -C4 -alkylene)--CO--(C1 -C6 -alkoxy), --CH(C1 -C4 -alkyl)-CO--O--(C1 -C6 -alkylene)-COOH, --CH(C1 -C4 -alkyl)-CO--O--(C1 -C6 -alkylene)-CO--(C1 -C6 -alkoxy), C3 -C9 -(α
-alkylalkylidene)iminooxy-C1 -C6 -alkyl, phenyl, phenyl-C1 -C6 -alkyl, phenyl-C3 -C6 -alkenyl, phenyl-C3 -C6 -alkynyl or phenoxy-C1 -C6 -alkyl, where the phenyl ring can in each case be unsubstituted or carry one to three radicals selected from the group comprising halogen, nitro, cyano, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, C1 -C4 -haloalkyl and C2 -C6 -alkenyl;
5- or 6-membered heteroaryl, heteroaryl-C1 -C6 -alkyl, heteroaryl-C3 -C6 -alkenyl, heteroaryl-C3 -C6 -alkynyl or heteroaryloxy-C1 -C6 -alkyl, where the heteroaryl radical in each case contains one to three hetero atoms selected from a group comprising one or two nitrogen atoms and one oxygen or sulfur atom, and it being possible for each heteroaromatic ring atom which can be substituted also to carry a radical selected from the group comprising hydroxyl, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio and C1 -C4 -haloalkyl;
R9 and R10 hydrogen, C1 -C8 -alkyl, C2 -C8 -alkenyl, C3 -C8 -alkynyl, C1 -C8 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C1 -C4 -alkylthio-C1 -C4 -alkyl, cyano-C1 -C8 -alkyl, carboxyl-C1 -C4 -alkyl, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl, (C1 -C6 -alkoxy)carbonyl-(C3 -C7 -cycloalkyl), C1 -C4 -alkylsulfonyl-C1 -C4 -alkyl, C3 -C8 -cycloalkyl, C1 -C6 -alkoxy, (C3 -C6 -cycloalkoxy)carbonyl-C1 -C4 -alkyl, C1 -C4 -alkoxy-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl, phenyl, phenyl-C1 -C4 -alkyl, where the phenyl ring can in each case be unsubstituted or carry one to three radicals selected from the group comprising halogen, nitro, cyano, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, C1 -C4 -haloalkyl and C2 -C6 -alkenyl,5- or 6-membered heteroaryl or heteroaryl-C1 -C4 -alkyl, where the heteroaryl radical contains one to three hetero atoms selected from a group comprising one or two nitrogen atoms and one oxygen or sulfur atom, and it being possible for each heteroaromatic ring atom which can be substituted also to carry a radical selected from the group comprising hydroxyl, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio and C1 -C4 -haloalkyl;
orR9 and R10 together a tetramethylene, pentamethylene or ethyleneoxyethylene chain, it being possible for each chain to carry a (C1 -C6 -alkoxy)carbonyl radical;
R11 hydrogen, C1 -C4 -alkyl, C3 -C6 -alkenyl, C3 -C6 -alkynyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, sodium, potassium, calcium, magnesium, ammonium or ammonium which is substituted by one to four C1 -C4 -alkyl- or benzyl radicals and can carry one to three further C1 -C4 -alkyl radicals;
R12 hydrogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C4 -alkoxy-C1 C4 -alkyl, C3 -C7 -cacloalkyl, which can in turn carry one to three radicals selected from the group comprising halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy and C1 -C4 -alkylthio, phenyl or phenyl-C1 -C6 -alkyl, where the phenyl ring can in each case be unsubstituted or carry one to three radicals selected from the group comprising halogen, nitro, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio and C1 -C4 -haloalkyl;
R13 and R14, independently of one another, C1 -C4 -alkyl, phenyl or thienyl, where the phenyl or thienyl radical can be unsubstituted or carry one to three radicals selected from the group comprising halogen, nitro, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio and C1 -C4 -haloalkyl;
R15, R16 and R17, independently of one another, hydrogen, halogen, C1 -C4 -alkyl, C2 -C4 -alkenyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl or C1 -C4 -alkylthio-C1 -C4 -alkyl;
R18 and R19, independently of one another, C1 -C8 -alkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl or C1 -C8 -haloalkyl;
R20, R21, R22, R23, R24 and R25, independently of one another, hydrogen, cyano, C1 -C8 -alkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, halo -C1 -C8 -alkyl, C1 -C8 -alkoxy, C1 -C4 -alkoxy-C1 -C4 -alkoxy, --CO--O--R8, --CO--N (R9,R10), --CO--R15, --S--R8, --SO2 --R8, --O--CO--R12 or C3 -C7 -cycloalkyl, which can in turn carry from one to three radicals selected from the group comprising halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy and C1 -C4 -alkylthio;
R26 C1 -C6 -alkyl, C1 -C6 -alkylthio, C1 -C6 -alkoxycarbonyl or C1 -C6 -alkoxycarbonyl-C1 -C4 -alkyl;
R27 C1 -C6 -alkyl, trifluoromethyl, C1 -C6 -alkoxy-C1 -C4 -alkyl, C2 -C7 -alkoxycarbonyl-C1 -C4 -alkyl, di-(C1 -C6 -alkoxycarbonyl)-C1 -C4 -alkyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -alkylthio, C1 -C6 -alkanoyl, C1 -C6 -alkoxycarbonyl, 2-furyl or phenyl which can be unsubstituted or in turn carry one to three radicals selected from the group comprising halogen, C1 -C4 -alkyl and C1 -C4 -alkoxy;
orR26 and R27 together with the carbon to which they are bonded a cyclopentane or cyclohexane ring which can in turn carry one to three C1 -C4 -alkyl radicals;
R28 hydrogen or C1 -C4 -alkyl;
R29 hydrogen, C1 -C4 -alkyl, phenyl or benzyl;
R30 hydrogen or C1 -C6 -alkyl;
R31 C1 -C6 -alkyl, C3 -C6 -cycloalkyl or phenyl;
X and Y, independently of one another, oxygen or sulfur;
and the N-oxides of I and the agriculturally utilizable salts of I where these exist,excepting those compounds I where R2 is C1 -C4 -alkoxy and R1 and/orR3 is carboxyl, its salt, ester or amide.
1 Assignment
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Accused Products
Abstract
Substituted 2-phenylpyridines I ##STR1## R1,R3 =H, halogen, alkyl, haloalkyl, alkoxyalkyl, alkoxy, alkoxyalkoxy, OH, haloalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, SH, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, CHO, CN, CO2 H, alkoxycarbonyl, alkoxyalkoxycarbonyl, haloalkoxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxyalkylcarbonyl, CONH2, alkyl-aminocarbonyl, dialkylaminocarbonyl, pyrrolidinyl-carbonyl piperidylcarbonyl, morpholinylcarbonyl, NO2, NH2, alkylamino, dialkylamino, pyrrolidinyl, piperidinyl, morpholinyl, alkylcarbonylamino, haloalkylcarbonylamino, alkylsulfonylamino;
R2 =halogen, CN, NO2, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio; or
R1 +R2 or R2 +R3 =trimethylene or tetramethylene chain;
R4 =halogen, alkyl, haloalkyl, alkoxyalkyl, alkoxy, alkoxyalkoxy, OH, haloalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, SH, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, CHO, CN, CO2 H, alkoxycarbonyl, alkoxyalkoxycarbonyl, haloalkoxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxyalkylcarbonyl, NO2, NH2, alkylamino, dialkylamino, pyrrolidinyl, piperidinyl, morpholinyl, alkylcarbonylamino, haloalkylcarbonylamino, alkylsulfonylamino;
R5 =hydrogen or halogen;
R6 =halogen, CN, NO2, OH, CF3, C1 -C6 -alkyl, C1 -C4 -alkoxy;
R7 =various radicals; and the N-oxides of I and the agriculturally utilizable salts of I where these exist, excepting those compounds I where R2 is C1 -C4 -alkoxy and R1 and/or R3 is carboxyl or the salt, ester or amide thereof.
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Citations
15 Claims
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1. A substituted 2-phenylpridine of the formula I ##STR93## in which the variables have the following meanings:
- R1 hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C1 -C4 -alkoxy-C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, (C1 -C5 -alkyl)carbonyloxy, (C1 -C5 -haloalkyl)carbonyloxy, SH, C1 -C4 -alkylthio, C1 -C4 -alkylsulfinyl, C1 -C4 -alkylsulfonyl, C1 -C4 -haloalkylthio, C1 -C4 -haloalkylsulfinyl, C1 -C4 -haloalkylsulfonyl, formyl, cyano, hydroxycarbonyl, (C1 -C4 -alkoxy) carbonyl, C1 -C4 -alkoxy(C1 -C4 -alkoxy)carbonyl, (C1 -C4 -haloalkoxy)carbonyl, (C1 -C4 -alkyl(carbonyl, (C1 -C4 -haloalkyl) carbonyl, C1 -C4 -alkoxy(C1 -C4 -alkyl)carbonyl, CONH2, (C1 -C4 -alkyl)aminocarbonyl, di-(C1 -C4 -alkyl)aminocarbonyl, pyrrolidinylcarbonyl, piperidinylcarbonyl morpholinylcarbonyl, nitro, amino, C1 -C4 -alkylamino, di-(C1 -C4 -alkyl)amino, pyrrolidinyl, piperidinyl, morpholinyl, (C1 -C4 -alkyl)carbonylamino, (C1 -C4 -haloalkyl)carbonylamino or C1 -C4 -alkylsulfonylamino;
R2 halogen, cyano, nitro, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, C1 -C4 -alkylthio, or C1 -C4 -haloalkylthio, or together with R1 or with R3 a trimethylene or tetramethylene chain; R3 hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkoxy-C1 -C4 -alkoxy, hydroxyl, C1 -C4 -haloalkoxy, (C1 -C5 -alkyl)carbonyloxy, (C1 -C5 -haloalkyl)carbonyloxy, SH, C1 -C4 -alkylthio, C1 -C4 -alkylsulfinyl, C1 -C4 -alkylsulfonyl, C1 -C4 -haloalkylthio, C1 -C4 -haloalkylsulfinyl, C1 -C4 -haloalkylsulfonyl, formyl, cyano, hydroxycarbonyl, (C1 -C4 -alkoxy)carbonyl, C1 -C4 -alkoxy(C1 -C4 -alkoxy)carbonyl, (C1 -C4 -haloalkoxy)carbonyl, (C1 -C4 -alkyl)carbonyl, (C1 -C4 -haloalkyl)carbonyl, C1 -C4 -alkoxy-(C1 -C4 C-alkyl)carbonyl, CONH2, (C1 -C4 -alkyl)aminocarbonyl, di-(C1 -C4 -alkyl)aminocarbonyl, pyrrolidinylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, nitro, amino, C1 -C4 -alkylamino, di-(C1 -C4 -alkyl)amino, pyrrolidinyl, piperidinyl, morpholinyl, (C1 -C4 -alkyl)carbonylamino, (C1 -C4 -haloalkyl)carbonylamino or C1 -C4 -alkylsulfonylamino; R4 halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkoxy, hydroxyl, C1 -C4 -haloalkoxy, (C1 -C5 -alkyl)carbonyloxy, (C1 -C5 -haloalkyl)carbonyloxy, SH, C1 -C4 -alkylthio, C1 -C4 -alkylsulfinyl, C1 -C4 -alkylsulfonyl, C1 -C4 -haloalkylthio, C1 -C4 -haloalkylsulfinyl, C1 -C4 -haloalkylsulfonyl, formyl, cyano, hydroxycarbonyl, (C1 -C4 -alkoxy)carbonyl, C1 -C4 -alkoxy-(C1 -C4 -alkoxy)carbonyl, (C1 -C4 -haloalkoxy)carbonyl, (C1 -C4 -alkyl)carbonyl, (C1 -C4 -haloalkyl)carbonyl, C1 -C4 -alkoxy-(C1 -C4 -alkyl)carbonyl, nitro, amino, C1 -C4 -alkylamino, di-(C1 -C4 -alkyl)amino, pyrrolidinyl, piperidinyl, morpholinyl, (C1 -C4 -alkyl)carbonylamino, (C1 -C4 -haloalkyl)carbonylamino or C1 -C4 -alkylsulfonylamino; R5 is hydrogen or halogen; R6 is halogen, cyano, nitro, hydroxyl, trifluoromethyl, C1 -C6 -alkyl or C1 -C4 -alkoxy; R7 chlorine, bromine, iodine, cyano, nitro, C1 -C8 -alkyl, C2 -C8 -alkenyl, C2 -C8 -alkynyl, C1 -C8 -haloalkyl, C2 -C8 -haloalkenyl, C2 -C8 -haloalkynyl, --(C1 -C8 -alkylene)-O--R8, --(C2 -C8 -alkenylene)-O--R8 -alkenylene-S--R8, --C2 -C8 -alkenylene)-S--R8, --(C2 -C8 -alkylene)-S--R8, --C1 -C8 -alkylene)-SO--R8, --(C2 -C8 -alkenylene)-SO--R8, --(C2 -C8 -alkynylene)-SO--R8, --(C1 -C8 -alkylene)-SO2 --R8, --(C2 -C8 -alkenylene)-SO2 --R8, --(C2 -C8 -alkynylene)-SO2 --R8, --O--R8, --S--R8, --SO--R8, --SO2 --R8, chlorosulfonyl, --SO2 --O--R8, --SO2 --N(R9,R10), --SO2 --NR9 (CO--R12), --N(R9,R10), --NR11 (CO--R12), --NR11 (SO2 --R13), --N(SO2 --R13)(SO2 --R14), --N(SO2 --R13)(CO--R12), --NH--CO--O--R8, --O--CO--NHR9, --O--CO--R12, --NH--CO--NHR9, --O--CS--N(C1 -C4 -alkyl)2, --O--CS--NH2, cyano-C1 14 C4 -alkyl, --CO--R8, --CO--O--N═
C(R26,R27), --CO--O--CH2 --O--N═
C(R30,R31), --CO--O--C(R28,R29)--CH2 --ON═
C(R30,R31), --CO--N(R9,R10), --CS--N(R9,R10), --CO--NH--SO2 --(C1 -C4 -alkyl), isoxazolinylcarbonyl, formyl, --CO--R15, hydroxycarbonyl-C1 -C6 -alkyl, (C1 14 C6 -alkoxy)carbonyl-C1 -C6 -alkyl, --CR15 ═
C(R16)--CHO, --C(R15)═
C(R16)--CO--O--R8, --C(R15)═
C(R16)--CO--N(R9,R10), --C(R15)═
C(R16)--CO--R17, --CH═
N--O--R8, --CH(XR18,YR19), --CH2 --CH(halogen)-CO--O--R8, --CH2 --CH(halogen)-CO--N(R9,R10), --CH2 --CH(halogen)-CO--(C1 -C4 -alkyl), --CH2 --CH(halogen)-CN, --C(C1 -C4 -alkoxy)=N--O--R8, --C(R15)═
C(R16)--C(C1 -C4 -alkoxy)=N--O--R8, --CH═
CH--CH═
CH--CO--O--R8, ##STR94## --C(R15)═
N--O--R8, --CO--OCH═
N--OH, --CO--OCH═
N--O--(C1 -C4 alkyl), --CO--OC(C1 -C4 -alkyl)=N--OH, --CO--OC(C1 -C4 -alkyl)=N--O--(C1 -C4 -alkyl), --CO--O--(CO1 -C4 -alkylene)--CH═
N--OH, --CO--O--(C1 -C4 -alkylene)-CH═
N--O--(C1 -C4 -alkyl), --CO--O--(C1 -C4 -alkylene)-C(C1 -C4 -alkylene)-C(C11 -C4 -alkyl)=N--OH, --CO--O--(C1 -C4 -alkyl)=N--O--(C1 -C4 -alkyl), --(C1 -C8 -alkylene)-O--CO--(C1 -C4 -alkyl), --CH═
C═
CH2, --CH═
C═
CH--(C1 -C4 -alkyl), ##STR95## 5- or 6-membered heteroaryl with one to three hetero atoms selected from a group comprising one or two nitrogen atoms and one oxygen or sulfur atom, it being possible for each heteroaromatic ring atom which can be substituted to carry a radical selected from the group comprising nitro, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio and (C1 -C4 -alkoxy)carbonyl;R8 hydrogen, C1 -C8 -alkyl, C1 -C8 -haloalkyl, C4 -C7 -cycloalkyl, which in turn can carry one to three C1 -C3 -alkyl radicals, C3 -C6 -alkenyl, C5 -C7 -cycloalkenyl, which in turn can carry one to three C1 -C3 -alkyl radicals, C3 -C6 -haloalkenyl, cyano-C1 -C8 -alkyl, C3 -C6 -alkynyl, C2 -C8 -alkoxyalkyl, 2-tetrahydrofuranyl-C1 -C8 -alkyl, 3-oxetanyl, 3-thietanyl, carboxyl-C1 -C6 -alkyl, (C1 -C8 -alkoxy) carbonyl-C1 -C6 -alkyl, (C1 -C6 -alkoxy)carbonyl-(C3 -C7 -cycloalkyl), C1 -C4 -alkoxy-(C1 -C4 -alkoxy)carbonyl-C1 -C6 -alkyl, cyclopropylmethyl, (1-methylthiocyclopropyl)methyl, --CH(SH)--CO--OH, --CH(SH)--CO--(C1 -C8 -alkoxy), --CH (C1 -C8 alkylthio)-COOH, --CH(C1 -C4 -alkylthio)-CO--(C1 -C8 -alkoxy), --CH2 --CO--N(R9)--R10, --CH(C1 -C4 -alkyl)-CO--N(R9)--R10, --(C1 -C4 -alkyl)2 --CO--N(R9)--R10, --CH2 --CO--N(9)--SO2 --(C1 -C4 -alkyl), --CH(C1 -C4 -alkyl)-CO--N(R9)--SO2 --C(C1 -C4 -alkyl)2 -CO--N(R9)--SO2 --(C1 -C4 -alkyl), --S--CO--NH2,--S--CO--N(C1 --alkyl)-(C1 -C4 -alkyl), CH2 --CO--O--(C1 -C6 -alkylene)-COOH, --CH2 --CO--O--(C1 -C6 -alkylene)-CO--(C1 -C6 -alkoxy), --C(C1 -C4 -alkyl)2 --CO--O--(C1 -C6 -alkylene)-COOH, --(C1 -C4 -alkyl)2 --CO--O--(C1 -C4 -alkylene)--CO--(C1 -C6 -alkoxy), --CH(C1 -C4 -alkyl)-CO--O--(C1 -C6 -alkylene)-COOH, --CH(C1 -C4 -alkyl)-CO--O--(C1 -C6 -alkylene)-CO--(C1 -C6 -alkoxy), C3 -C9 -(α
-alkylalkylidene)iminooxy-C1 -C6 -alkyl, phenyl, phenyl-C1 -C6 -alkyl, phenyl-C3 -C6 -alkenyl, phenyl-C3 -C6 -alkynyl or phenoxy-C1 -C6 -alkyl, where the phenyl ring can in each case be unsubstituted or carry one to three radicals selected from the group comprising halogen, nitro, cyano, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, C1 -C4 -haloalkyl and C2 -C6 -alkenyl;5- or 6-membered heteroaryl, heteroaryl-C1 -C6 -alkyl, heteroaryl-C3 -C6 -alkenyl, heteroaryl-C3 -C6 -alkynyl or heteroaryloxy-C1 -C6 -alkyl, where the heteroaryl radical in each case contains one to three hetero atoms selected from a group comprising one or two nitrogen atoms and one oxygen or sulfur atom, and it being possible for each heteroaromatic ring atom which can be substituted also to carry a radical selected from the group comprising hydroxyl, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio and C1 -C4 -haloalkyl; R9 and R10 hydrogen, C1 -C8 -alkyl, C2 -C8 -alkenyl, C3 -C8 -alkynyl, C1 -C8 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C1 -C4 -alkylthio-C1 -C4 -alkyl, cyano-C1 -C8 -alkyl, carboxyl-C1 -C4 -alkyl, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl, (C1 -C6 -alkoxy)carbonyl-(C3 -C7 -cycloalkyl), C1 -C4 -alkylsulfonyl-C1 -C4 -alkyl, C3 -C8 -cycloalkyl, C1 -C6 -alkoxy, (C3 -C6 -cycloalkoxy)carbonyl-C1 -C4 -alkyl, C1 -C4 -alkoxy-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl, phenyl, phenyl-C1 -C4 -alkyl, where the phenyl ring can in each case be unsubstituted or carry one to three radicals selected from the group comprising halogen, nitro, cyano, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, C1 -C4 -haloalkyl and C2 -C6 -alkenyl, 5- or 6-membered heteroaryl or heteroaryl-C1 -C4 -alkyl, where the heteroaryl radical contains one to three hetero atoms selected from a group comprising one or two nitrogen atoms and one oxygen or sulfur atom, and it being possible for each heteroaromatic ring atom which can be substituted also to carry a radical selected from the group comprising hydroxyl, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio and C1 -C4 -haloalkyl;
orR9 and R10 together a tetramethylene, pentamethylene or ethyleneoxyethylene chain, it being possible for each chain to carry a (C1 -C6 -alkoxy)carbonyl radical; R11 hydrogen, C1 -C4 -alkyl, C3 -C6 -alkenyl, C3 -C6 -alkynyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, sodium, potassium, calcium, magnesium, ammonium or ammonium which is substituted by one to four C1 -C4 -alkyl- or benzyl radicals and can carry one to three further C1 -C4 -alkyl radicals; R12 hydrogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C4 -alkoxy-C1 C4 -alkyl, C3 -C7 -cacloalkyl, which can in turn carry one to three radicals selected from the group comprising halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy and C1 -C4 -alkylthio, phenyl or phenyl-C1 -C6 -alkyl, where the phenyl ring can in each case be unsubstituted or carry one to three radicals selected from the group comprising halogen, nitro, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio and C1 -C4 -haloalkyl; R13 and R14, independently of one another, C1 -C4 -alkyl, phenyl or thienyl, where the phenyl or thienyl radical can be unsubstituted or carry one to three radicals selected from the group comprising halogen, nitro, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio and C1 -C4 -haloalkyl; R15, R16 and R17, independently of one another, hydrogen, halogen, C1 -C4 -alkyl, C2 -C4 -alkenyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl or C1 -C4 -alkylthio-C1 -C4 -alkyl; R18 and R19, independently of one another, C1 -C8 -alkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl or C1 -C8 -haloalkyl; R20, R21, R22, R23, R24 and R25, independently of one another, hydrogen, cyano, C1 -C8 -alkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, halo -C1 -C8 -alkyl, C1 -C8 -alkoxy, C1 -C4 -alkoxy-C1 -C4 -alkoxy, --CO--O--R8, --CO--N (R9,R10), --CO--R15, --S--R8, --SO2 --R8, --O--CO--R12 or C3 -C7 -cycloalkyl, which can in turn carry from one to three radicals selected from the group comprising halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy and C1 -C4 -alkylthio; R26 C1 -C6 -alkyl, C1 -C6 -alkylthio, C1 -C6 -alkoxycarbonyl or C1 -C6 -alkoxycarbonyl-C1 -C4 -alkyl; R27 C1 -C6 -alkyl, trifluoromethyl, C1 -C6 -alkoxy-C1 -C4 -alkyl, C2 -C7 -alkoxycarbonyl-C1 -C4 -alkyl, di-(C1 -C6 -alkoxycarbonyl)-C1 -C4 -alkyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -alkylthio, C1 -C6 -alkanoyl, C1 -C6 -alkoxycarbonyl, 2-furyl or phenyl which can be unsubstituted or in turn carry one to three radicals selected from the group comprising halogen, C1 -C4 -alkyl and C1 -C4 -alkoxy;
orR26 and R27 together with the carbon to which they are bonded a cyclopentane or cyclohexane ring which can in turn carry one to three C1 -C4 -alkyl radicals; R28 hydrogen or C1 -C4 -alkyl; R29 hydrogen, C1 -C4 -alkyl, phenyl or benzyl; R30 hydrogen or C1 -C6 -alkyl; R31 C1 -C6 -alkyl, C3 -C6 -cycloalkyl or phenyl; X and Y, independently of one another, oxygen or sulfur; and the N-oxides of I and the agriculturally utilizable salts of I where these exist, excepting those compounds I where R2 is C1 -C4 -alkoxy and R1 and/or R3 is carboxyl, its salt, ester or amide. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15)
- R1 hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C1 -C4 -alkoxy-C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, (C1 -C5 -alkyl)carbonyloxy, (C1 -C5 -haloalkyl)carbonyloxy, SH, C1 -C4 -alkylthio, C1 -C4 -alkylsulfinyl, C1 -C4 -alkylsulfonyl, C1 -C4 -haloalkylthio, C1 -C4 -haloalkylsulfinyl, C1 -C4 -haloalkylsulfonyl, formyl, cyano, hydroxycarbonyl, (C1 -C4 -alkoxy) carbonyl, C1 -C4 -alkoxy(C1 -C4 -alkoxy)carbonyl, (C1 -C4 -haloalkoxy)carbonyl, (C1 -C4 -alkyl(carbonyl, (C1 -C4 -haloalkyl) carbonyl, C1 -C4 -alkoxy(C1 -C4 -alkyl)carbonyl, CONH2, (C1 -C4 -alkyl)aminocarbonyl, di-(C1 -C4 -alkyl)aminocarbonyl, pyrrolidinylcarbonyl, piperidinylcarbonyl morpholinylcarbonyl, nitro, amino, C1 -C4 -alkylamino, di-(C1 -C4 -alkyl)amino, pyrrolidinyl, piperidinyl, morpholinyl, (C1 -C4 -alkyl)carbonylamino, (C1 -C4 -haloalkyl)carbonylamino or C1 -C4 -alkylsulfonylamino;
Specification
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Current AssigneeBASF AG (BASF SE)
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Original AssigneeBASF AG (BASF SE)
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InventorsSchaefer, Peter, Walter, Helmut, Hamprecht, Gerhard, Westphalen, Karl-Otto, Gerber, Matthias, Heistracher, Elisabeth, Klintz, Ralf, Koenig, Hartmann, Rang, Harald, Muenster, Peter
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Primary Examiner(s)DENTZ, BERNARD I
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Application NumberUS08/592,355Time in Patent Office922 DaysField of Search546/334, 546/342, 546/344, 546/345, 504/244, 504/254US Class Current504/244CPC Class CodesC07D 213/30 Oxygen atomsC07D 213/61 Halogen atoms or nitro radi...C07D 265/36 condensed with one six-memb...C07D 409/12 linked by a chain containin...
