Patent EP-2229813-A1 (EP)
Inventor: BRÜNJES MARCO DR
IPC: A01N43/54
Filed: 2009-03-21
Abstract: Pyrimidin-4-yl propane dinitrile compounds (I) or their N-oxide and salts are new. Pyrimidin-4-yl propane dinitrile compounds of formula (I) or their N-oxide and salts are new. R 1>phenyl (optionally substituted with 1-3 of Rx), 1-6C alkyl (optionally substituted with Ry) or 2-6C alkenyl (optionally substituted with 1-3 Rz); R 2>F, Cl, Br, I (all preferred), H, CN, NO 2, OR 5>, SR 6>or N(R 7>)R 8>; either R 3>H, 1-4C alkyl (optionally substituted with 1-2 of R 9>), 2-4C alkenyl (optionally substituted with 1-2 of R 1>0>), 2-4C alkynyl (optionally substituted with 1-2 of 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 with 1-2 of R 9>) or C(=O)R 1>2>; or R 3>+R 4>-(CH 2) 4-, -(CH 2) 5-, -CH 2CH=CHCH 2- or -(CH 2) 2O(CH 2) 2- (all optionally substituted with 1-2 of R 1>9>), or =C(R 2>0>)N(R 2>1>)R 2>2>or =C(R 2>3>)OR 2>4>; R 5>, R 6>H, 1-4C alkyl or 1-3C haloalkyl; R 7>, R 8>H or 1-4C alkyl; R 9>, R 1>0>halo, 1-3C (halo)alkoxy, 1-3C (halo)alkylthio, amino, 1-3C alkylamino, 2-4C dialkylamino or 2-4C alkoxycarbonyl; 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 with 1-3 of 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 (halo)alkoxy, 1-3C (halo)alkylthio, amino, 1-3C alkylamino, 2-4C dialkylamino or 2-4C alkoxycarbonyl; R 2>0>H or 1-4C alkyl; either R 2>1>, R 2>2>H or 1-4C alkyl; or R 2>1>+R 2>2>-(CH 2) 4-, -(CH 2) 5-, -CH 2CH=CHCH 2- or -(CH 2) 2O(CH 2) 2-; R 2>3>H or 1-4C alkyl; 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; R 2>8>halo, cyano, nitro, 1-6C (halo)alkyl, 2-4C (halo)alkenyl, 3-4C (halo)alkynyl, 1-4C (halo)alkoxy, 1-4C (halo)alkylthio, 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; either Rx : phenyl, phenoxy or 5-6 membered heteroaromatic ring (all optionally substituted with 1-3 of R 2>8>), halo, cyano, nitro, 1-6C (halo)alkyl, 1-4C hydroxyalkyl, 2-4C (halo)alkoxyalkyl, 2-4C (halo)alkenyl, 2-4C alkynyl, 3-4C haloalkynyl, OH, 1-4C (halo)alkoxy, 2-4C (halo)alkenyloxy, 2-4C alkynyloxy, 3-4C haloalkynyloxy, 1-4C (halo)alkylthio, 1-4C (halo)alkylsulfinyl, 1-4C (halo)alkylsulfonyl, 2-4C (halo)alkenylthio, 2-4C (halo)alkenylsulfinyl, 2-4C (halo)alkenylsulfonyl, 2-4C alkynylthio, 3-4C haloalkynylthio, 3-4C (halo)alkynylsulfinyl, 3-4C (halo)alkynylsulfonyl, 1-6C alkylamino, 2-8C dialkylamino, 2-6C alkylcarbonyl, 2-6C alkoxycarbonyl, 2-6C alkylaminocarbonyl, 3-8C dialkylaminocarbonyl or 3-6C trialkylsilyl; or two adjacent 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-; Ry : halo, 2-6C (halo)alkenyl, 1-3C alkoxy, 1-2C haloalkoxy, 1-3C alkylthio or 1-2C haloalkylthio; and Rz : halo, 1-6C (halo)alkyl, 1-3C alkoxy, 1-2C haloalkoxy, 1-3C alkylthio or 1-2C haloalkylthio. Independent claims are included for: (1) an agrochemical agent comprising (I), one or more agrochemical active agents that are different from (I), and optionally auxiliary agents and additives; and (2) the preparation of (I). [Image] ACTIVITY : Herbicide; Plant Growth Regulant. MECHANISM OF ACTION : None given.