Title:
ピリミジン−４−イルプロパンジニトリル誘導体、この製造方法ならびに除草剤および植物生長調節剤としてのその使用
Document Type and Number:
Japanese Patent JP5784580
Kind Code:
B2
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.
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Inventors:
Dietrich, Hans Jörg
Ahrenth, Hartmut
Hoffmann, Michael Gerhard
Jan, Datesgen
Huicht, Dieter
Rosinger, Christopher Hiyu
Heuser-Hahn, Isolde
Briuniyues, Marco
Ahrenth, Hartmut
Hoffmann, Michael Gerhard
Jan, Datesgen
Huicht, Dieter
Rosinger, Christopher Hiyu
Heuser-Hahn, Isolde
Briuniyues, Marco
Application Number:
JP2012500129A
Publication Date:
September 24, 2015
Filing Date:
March 13, 2010
Export Citation:
Assignee:
Bayer Intellectual Property GmbH
International Classes:
C07D239/42; A01N43/54; A01N47/02; A01N55/02; A01P13/02; A01P21/00; C07D239/30
Domestic Patent References:
| JP60072808A | ||||
| JP50155624A | ||||
| JP8504414A |
Foreign References:
| WO2005063721A1 | ||||
| WO2007082076A1 |
Attorney, Agent or Firm:
Makoto Ono
Kenkyo Kanayama
Mitsuaki Tsubokura
Kazuki Shigemori
Kenji Ando
Hidehiko Ichikawa
Takahiro Aoki
Yoshie Sakurada
Yousuke Kawasaki
Toshikazu Imato
Yoshikazu Iwase
Yasufumi Shiroyama
Kawaguchi International Patent Office
Kenkyo Kanayama
Mitsuaki Tsubokura
Kazuki Shigemori
Kenji Ando
Hidehiko Ichikawa
Takahiro Aoki
Yoshie Sakurada
Yousuke Kawasaki
Toshikazu Imato
Yoshikazu Iwase
Yasufumi Shiroyama
Kawaguchi International Patent Office