6-(2-aminophenyl)picolinates and their use as herbicides

摘要

The present invention relates to novel herbicidally active 6-(2-aminophenyl)picoline derivatives and to processes for preparation thereof. The present invention further provides for the use thereof as a herbicide, especially as a herbicide for selective control of weed plants in useful plant crops, and as a plant growth regulator alone or in combination with safeners and/or in a mixture with other herbicides.

主权项

1. A 6-(2-aminophenyl)picolinate of formula (I)or an agrochemically suitable carboxylic derivative thereof selected from salts, esters, acyl hydrazides, imidates, thioimidates, amidines, amides, orthoesters, acyl cyanides, acyl halides, thioesters, thionoesters, dithiol esters, and nitrile or an agrochemically suitable amino derivative selected from salts, N-oxides, amides, sulfonanamides, and carbamates,
in which n is 0, 1, 2, 3, or 4; R1 is selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxyl, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C4)hydroxyalkyl, (C2-C6)alkoxyalkyl, (C2-C6)halo-alkoxyalkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)alkynyl, (C3-C6)haloalkynyl, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C2-C6)alkenyloxy, (C2-C6)haloalkenyloxy, (C2-C6)-alkynyloxy, (C3-C6)haloalkynyloxy, (C1-C6)alkylthio, (C2-C6)alkylthioalkyl, (C1-C6)halo-alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)alkenylthio, (C2-C6)haloalkenylthio, (C2-C6)alkenylsulfinyl, (C2-C6)haloalkenylsulfinyl, (C2-C6)alkenylsulfonyl, (C2-C6)haloalkenylsulfonyl, (C2-C6)-alkynylthio, (C3-C6)haloalkynylthio, (C3-C6)alkynylsulfinyl, (C3-C6)haloalkynylsulfinyl, (C3-C6)alkynylsulfonyl, (C3-C6)haloalkynylsulfonyl, (C1-C6)alkylamino, (C2-C6)dialkyl-amino, (C2-C6)alkylaminoalkyl, (C2-C6)alkylcarbonyl, (C2-C6)alkoxycarbonyl, (C2-C6)-aminocarbonyl, (C2-C6)alkylaminocarbonyl, (C3-C8)dialkylaminocarbonyl, (C3-C6)-trialkylsilyl, phenyl, phenoxy and 5- or 6-membered heteroaromatic rings, where each phenyl ring, phenoxy ring or 5- or 6-membered heteroaromatic ring may optionally be substituted by one to three R25radicals; or where two adjacent R1 radicals may together form an —OCH2O—, —CH2CH2O—, —OCH2CH2O—, —OCH(CH3)O—, —OC(CH3)2O—,—OCF2O—, —CF2CF2O—,—OCF2CF2O— or —CH═CH—CH═CH— group; R2 is hydrogen, halogen, cyano, nitro, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C6)-alkylamino, (C1-C6)dialkylamino, (C1-C6)thioalkoxy, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)alkynyl; R3 is hydrogen, (C1-C4)alkyl optionally substituted by one or two R6 radicals, (C2-C4)alkenyl optionally substituted by one or two R7 radicals, or (C2-C4)alkynyl optionally substituted by one or two R8 radicals; or R3 is C(═O)R9, NO2, OR10, S(O)2R11, N(R12)R13 or N═C(R14)R15; R4 is hydrogen, (C1-C4)alkyl optionally substituted by one or two R6 radicals, or C(═O)R9; or R3 and R4 together form a —(CH2)4—, —(CH2)5—, —CH2CH═CHCH2— or —(CH2)2O(CH2)2— group which is optionally substituted by one or two R16 radicals; or R3 and R4 together form a ═C(R17)N(R18)R19 or ═C(R20)OR21 group; R5 is hydrogen, halogen, cyano, nitro, formyl, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)alkoxy, (C1-C6)thioalkoxy, (C2-C6)alkoxy-alkyl, (C2-C6)thioalkoxyalkyl; R6, R7 and R8 are each independently selected from halogen, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C1-C3)alkylthio, (C1-C3)haloalkylthio, amino, (C1-C3)alkylamino, (C2-C4)dialkylamino and (C2-C4) alkoxycarbonyl; R9 is hydrogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, phenyl, phenoxy, benzyl or benzyloxy; R10 is hydrogen, (C1-C4)alkyl, (C1-C3)haloalkyl or CHR22C(O)OR23; R11 is (C1-C4)alkyl, (C1-C4)haloalkyl or phenyl optionally substituted by one, two or three radicals selected independently from CH3, Cl and OCH3; R12 is hydrogen, (C1-C4)alkyl or C(═O)R24; R13 is hydrogen or (C1-C4)alkyl; R14 is hydrogen, (C1-C4)alkyl or phenyl optionally substituted by one, two or three radicals selected independently from CH3, Cl or OCH3; R15 is hydrogen or (C1-C4)alkyl; or R14 and R15 together form a —(CH2)4— or —(CH2)5— group; R16 is independently halogen, (C1-C3)alkyl, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C1-C3)alkylthio, (C1-C3)haloalkylthio, amino, (C1-C3)alkylamino, (C2-C4)dialkylamino or (C2-C4)alkoxycarbonyl; R17 is hydrogen or (C1-C4)alkyl; R18 and R19 are each independently selected from hydrogen and (C1-C4)alkyl; or R18 and R19 together form a —(CH2)4—, —(CH2)5—, —CH2CH═CHCH2— or —(CH2)2O(CH2)2— group; R20 is hydrogen or (C1-C4)alkyl; R21 is (C1-C4)alkyl; R22 is hydrogen, (C1-C4)alkyl, (C1-C3)haloalkyl, (C1-C4)alkoxy, phenyl, phenoxy or benzyloxy; R23 is hydrogen, (C1-C4)alkyl or (C1-C4)alkoxy; R24 is hydrogen, C1-C4 alkyl or benzyl; and R25 is, optionally independently of further R25 radicals, selected from halogen, cyano, nitro, (C1-C6)alkyl, (C1-C6)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C3-C4)alkynyl, (C3-C4)haloalkynyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)halo-alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)alkylamino, (C2-C8)dialkylamino, (C2-C4)alkylcarbonyl, (C2-C6)alkoxycarbonyl, (C2-C6)alkylaminocarbonyl, (C3-C8)dialkylaminocarbonyl and (C3-C6)trialkylsilyl.