5-aminopyrimidine derivatives and use thereof for combating undesired plant growth

Patent metadata

Field	Value
Publication number	US-9375002-B2
Application number	US-201314387267-A
Country	US
Kind code	B2
Filing date	Mar 27, 2013
Priority date	Mar 29, 2012
Publication date	Jun 28, 2016
Grant date	Jun 28, 2016

Abstract

What is described are compounds of the general formula (I) and agrochemically acceptable salts thereof

and their use in the field of crop protection.

First claim

The invention claimed is:

1. A compound of formula (I) or an agrochemically acceptable salt thereof

in which
R 1 is selected from the group consisting of

cyano (CN), NO 2 , (C 1 -C 3 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkyl sulfoxide, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 1 -C 6 )-alkoxy-carbonyl, amino-carbonyl, mono-((C 1 -C 6 )-alkyl)-amino-carbonyl, di-((C 1 -C 6 )-alkyl)-amino-carbonyl, (C 6 -C 14 )-aryl, (C 6 -C 14 )-aryl-haloalkyl, (C 1 -C 6 )-aryloxy, (C 6 -C 14 )-haloaryl-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkynyl-(C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkynyl-(C 1 -C 6 )-alkyl-(C 1 -C 6 )-alkoxy, and (C 1 -C 6 )-alkyl-(C 2 -C 6 )-alkynyl-(C 1 -C 6 )-alkoxy; and
R 2a and R 2b , each independently of one another, are selected from the group consisting of
hydrogen, halogen, hydroxy, cyano, nitro, C(O)OH, C(O)NH 2 ;
(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-haloalkylcarbonyl, (C 1 -C 6 )-alkylcarbonyloxy, (C 1 -C 6 )-haloalkylcarbonyloxy, (C 1 -C 6 )-alkylcarbonyl-(C 1 -C 4 )-alkyl;
(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-haloalkoxycarbonyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxycarbonyl-(C 1 -C 6 )-haloalkyl;
(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkenylcarbonyl, (C 2 -C 6 )-haloalkenylcarbonyl, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-alkenyloxycarbonyl, (C 2 -C 6 )-haloalkenyloxycarbonyl;
(C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl, (C 2 -C 6 )-haloalkynyloxycarbonyl;
tri-(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl, di-(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl, mono-(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl; phenylsilyl-(C 2 -C 6 )-alkynyl;
(C 6 -C 14 )-aryl, (C 6 -C 14 )-aryloxy, (C 6 -C 14 )-arylcarbonyl and (C 6 -C 14 )-aryloxycarbonyl, each of which may be substituted at the aryl moiety by halogen, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl;
(C 6 -C 14 )-aryl-(C 1 -C 6 )-alkyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxy, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkyl-carbonyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkyl-carbonyloxy, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxycarbonyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxycarbonyloxy;
N—((C 1 -C 6 )-haloalkanoyl)-amino, aminocarbonyl-(C 1 -C 6 )-alkyl, di-(C 1 -C 6 )-alkylaminocarbonyl-(C 1 -C 6 )-alkyl;
N—((C 1 -C 6 )-haloalkanoyl)-amino-carbonyl, mono-((C 6 -C 14 )-aryl)-amino-carbonyl, di-((C 6 -C 14 )-aryl)-amino-carbonyl;
(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkoxy;
(C 3 -C 8 )-cycloalkyl, which may optionally be substituted at the cycloalkyl radical by (C 1 -C 6 )-alkyl or halogen; (C 3 -C 8 )-cycloalkoxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxy, (C 3 -C 8 )-cycloalkylcarbonyl, (C 3 -C 8 )-cycloalkoxycarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkylcarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxycarbonyl, (C 3 -C 8 )-cycloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkoxycarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkylcarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxycarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxycarbonyloxy;
(C 3 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkenyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxy, (C 3 -C 8 )-cycloalkenylcarbonyl, (C 3 -C 8 )-cycloalkenyloxycarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkylcarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxycarbonyl, (C 3 -C 8 )-cycloalkenylcarbonyloxy, (C 3 -C 8 )-cycloalkenyloxycarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkylcarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxycarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxycarbonyloxy;
hydroxy-(C 1 -C 6 )-alkyl, hydroxy-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkyl;
(C 1 -C 6 )-alkylsulfonyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-haloalkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylsulfonyloxy, (C 1 -C 6 )-haloalkylsulfonyloxy, (C 1 -C 6 )-alkylthiocarbonyl, (C 1 -C 6 )-haloalkylthiocarbonyl, (C 1 -C 6 )-alkylthiocarbonyloxy, (C 1 -C 6 )-haloalkylthiocarbonyloxy, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkylcarbonyloxy; (C 4 -C 14 )-arylsulfonyl, (C 6 -C 14 )-arylthio, (C 6 -C 14 )-arylsulfinyl, (C 3 -C 8 )-cycloalkylthio, (C 3 -C 8 )-alkenylthio, (C 3 -C 8 )-cycloalkenylthio, and (C 3 -C 6 )-alkynylthio; and

R 3 is selected from the group consisting of
hydrogen, cyano, C(O)OH, C(O)NH 2 ;
(C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl; and
(C 1 -C 6 )-alkoxycarbonyl; and

R 4 and R 5 , each independently of one another, are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, hydroxy, (C 1 -C 6 )-alkoxy and (C 1 -C 6 )-haloalkoxy; or the radicals R 4 and R 5 together with the carbon atom to which they are attached form a three- to seven-membered ring; and
R 6 and R 7 , each independently of one another, are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 6 -C 14 )-aryl, (C 6 -C 14 )-aryloxy, (C 6 -C 14 )-arylcarbonyl and (C 6 -C 14 )-aryloxycarbonyl; or the radicals R 6 and R 7 together form a (C 1 -C 7 )-alkylene group, which may contain one or more oxygen or sulfur atoms, where the (C 1 -C 7 )-alkylene group may be mono- or polysubstituted by halogen and the halogen substituents in question may be identical or different, and
n is the number 0, 1 or 2 and
R 8 , R 9 , R 10 and R 11 , each independently of one another, are selected from the group consisting of hydrogen, halogen, cyano, C(O)OH, C(O)NH 2 , (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkyloxycarbonyl, (C 1 -C 6 )-alkylaminocarbonyl, (C 1 -C 6 )-di-alkylaminocarbonyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl and (C 2 -C 6 )-haloalkynyloxycarbon

Assignees

• Bayer Ip Gmbh

Inventors

• Minn Klemens
• Hoffmann Michael Gerhard
• Gatzweiler Elmar
• Heinemann Ines
• Haeuser-Hahn Isolde
• Rosinger Christopher Hugh

Classifications

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D239/42

  One nitrogen atom (nitro radicals C07D239/30) · CPC title

• A01N43/54 Primary

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• C07D239/47

  One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title