Patent EP-2471776-A1 (EP)
Inventor: BRUENJES MARCO
IPC: A01N43/40
Filed: 2010-12-28
Abstract: Pyridin-2-yl-propan-dinitrile compounds (I) and their N-oxides, salts or derivatives are new. Pyridin-2-yl-propan-dinitrile compounds of formula (I) and their N-oxides, salts or derivatives are new. R 1>phenyl (optionally substituted by 1-3 R1x), (1-6C)-alkyl (optionally substituted by 1-3 R1y) or (2-6C)alkenyl (optionally substituted by 1-3 R1z); either R1x : phenyl, phenoxy or a 5 or 6-membered heteroaryl ring (all optionally substituted by 1-3 R 2>8>), halo, CN, nitro, amino, (1-6C)alkyl, (1-6C)haloalkyl, (1-4C)hydroxyalkyl, (2-4C)alkoxyalkyl, (2-4C)haloalkoxyalkyl, (2-4C)alkenyl, (2-4C)haloalkenyl, (2-4C)alkynyl, (3-4C)haloalkynyl, OH, (1-4C)alkoxy, (1-4C)haloalkoxy, (2-4C)alkenyloxy, (2-4C)haloalkenyloxy, (2-4C)alkynyloxy, (3-4C)haloalkynyloxy, (1-4C)alkylthio, (1-4C)haloalkylthio, (1-4C)alkylsulfinyl, (1-4C)haloalkylsulfinyl, (1-4C)alkylsulfonyl, (1-4C)haloalkylsulfonyl, (2-4C)alkenylthio, (2-4C)haloalkenylthio, (2-4C)alkenylsulfinyl, (2-4C)haloalkenylsulfinyl, (2-4C)alkenylsulfonyl, (2-4C)haloalkenylsulfonyl, (2-4C)alkynylthio, (3-4C)haloalkynylthio, (3-4C)alkynylsulfinyl, (3-4C)haloalkynylsulfinyl, (3-4C)alkynylsulfonyl, (3-4C)haloalkynylsulfonyl, (1-6C)alkylamino, (2-8C)dialkylamino, (2-6C)alkylcarbonyl, (2-6C) alkoxycarbonyl, (2-6C)alkylaminocarbonyl, (3-8C)dialkylaminocarbonyl or (3-6C)trialkylsilyl; or 2R1x : Rx-OCH 2O-, -CH 2CH 2O-, -OCH 2CH 2O-, -OCH(CH 3)O-, -OC(CH 3) 2O-, -OCF 2O-, -CF 2CF 2O-, -OCF 2CF 2O- or -CH=CH-CH=CH-; R1y : halo, (2-6C)alkenyl, (2-6C)haloalkenyl, (1-3C)alkoxy, (1-2C)haloalkoxy, (1-3C)alkylthio or (1-2C)haloalkylthio; R1z : halo, (1-6C)alkyl, (1-6C)haloalkyl, (1-3C)alkoxy, (1-2C)haloalkoxy, (1-3C)alkylthio or (1-2C)haloalkylthio; R 2>H, F, Cl, B, I, CN, nitro, hydroxy (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (1-4C)alkoxy, (1-4C)haloalkyl, (1-4C)haloalkoxy, SR 6>or N(R 7>)R 8>; R 6>H, (1-4C)alkyl or (1-3C)haloalkyl; R 7>, R 8>H or (1-4C)alkyl; either R 3>H, (1-4C)alkyl (optionally substituted by 1 or 2 R 9>), (2-4C)alkenyl (optional substituted by 1 or 2 R 1>0>), (2-4C)alkynyl (optionally substituted by 1 or 2 R 1>1>), C(=O)R 1>2>, NO 2, OR 1>3>, S(O) 2R 1>4>, N(R 1>5>)R 1>6>or N=C(R 1>7>)R 1>8>; and R 4>H, (1-4C)alkyl (optionally substituted by 1 or 2 R 9>) or C(=O)R 1>2>; or R 3>R 4>-(CH 2) 4-, -(CH 2) 5-, -CH 2CH=CHCH 2-, -(CH 2) 2O(CH 2) 2- (all optionally substituted by 1 or 2 R 1>9>), =C(R 2>0>)N(R 2>1>)R 2>2>or =C(R 2>3>)OR 2>4>; R 9>-R 1>1>halo, (1-3C)alkoxy, (1-3C)haloalkoxy, (1-3C)alkylthio, (1-3C)haloalkylthio, amino, (1-3C)alkylamino, (2-4C)dialkylamino or (2-4C)alkoxycarbonyl; R 5>H, F, Cl, Br, I, CN, nitro, OH, (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (1-4C)alkoxy, (1-4C)haloalkyl, (1-4C)haloalkoxy, (1-4C)alkylthio, (1-4C)haloalkylthio, (1-4C)alkylamino or (1-4C)dialkylamino; R 1>2>H, (1-4C)alkyl, (1-3C)haloalkyl, (1-4C)alkoxy, phenyl, phenoxy or benzyloxy; R 1>3>H, (1-4C)alkyl, (1-3C)haloalkyl or CHR 2>5>C(O)OR 2>6>; R 1>4>(1-4C)alkyl or (1-3C)haloalkyl; R 1>5>H, (1-4C)alkyl or C(=O)R 2>7>; R 1>6>H or (1-4C)alkyl; either R 1>7>H, (1-4C)alkyl or phenyl (optionally substituted by 1-3 CH 3, Cl or OCH 3); and R 1>8>H or (1-4C) alkyl; or R 1>7>R 1>8>-(CH 2) 4- or -(CH 2) 5-; R 1>9>halo, (1-3C)alkyl, (1-3C)alkoxy, (1-3C)haloalkoxy, (1-3C)alkylthio, (1-3C)haloalkylthio, amino, (1-3C)alkylamino, (2-4C)dialkylamino or (2-4C)alkoxycarbonyl; either R 2>0>-R 2>3>H or (1-4C)alkyl; or R 2>1>R 2>2>-(CH 2) 4-, -(CH 2) 5-, -CH 2CH=CHCH 2or -(CH 2) 2O(CH 2) 2-; R 2>4>(1-4C)alkyl; R 2>5>H, (1-4C)alkyl, (1-3C)haloalkyl, (1-4C)alkoxy, phenyl, phenoxy or benzyloxy; R 2>6>H, (1-4C)alkyl or (1-4C)alkoxy; R 2>7>H, (1-4C)alkyl or benzyl; and R 2>8>halo, CN, nitro, (1-6C)alkyl, (1-6C)haloalkyl, (2-4C)alkenyl, (2-4C)haloalkenyl, (3-4C)alkynyl, (3-4C)haloalkynyl, (1-4C)alkoxy, (1-4C)haloalkoxy, (1-4C)alkylthio, (1-4C)haloalkylthio, (1-4C)alkylsulfinyl, (1-4C)alkylsulfonyl, (1-4C)alkylamino, (2-8C)dialkylamino, (2-4C)alkylcarbonyl, (2-6C)alkoxycarbonyl, (2-6C)alkylaminocarbonyl, (3-8C)dialkylaminocarbonyl or (3-6C)trialkylsilyl. Independent claims are included for: (1) an agent comprising (I), active agent other than (I), optionally additives and auxiliary agents; (2) the preparation of (I); and (3) a pyridine compound of formula (II). X : leaving group such as Cl, Br, I or methanesulfonyl. [Image] [Image] ACTIVITY : Herbicide; Plant Growth Regulant. MECHANISM OF ACTION : None given.