Diaminotriazine compounds as herbicides

Patent metadata

Field	Value
Publication number	US-9822105-B2
Application number	US-201515305823-A
Country	US
Kind code	B2
Filing date	Apr 22, 2015
Priority date	Apr 23, 2014
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

The present invention relates to diaminotriazine compounds and to their use as herbicides. The present invention also relates to agrochemical compositions for crop protection and to a method for controlling unwanted vegetation.

wherein
A is a fused saturated or unsaturated, 5-, 6-membered carbocycle or a fused saturated or unsaturated, 5-, 6-membered heterocycle;
P is 1 or 2
q is 0, 1, 2 or 3;
R b is inter alia halogen, OH, CN, amino, NO 2 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, etc.;
R 1 is inter alia H, OH, S(O) 2 NH 2 , CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy, etc.;
R 2 is inter alia H, OH, S(O) 2 NH 2 , CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy, etc;
X is a radical selected from the group consisting of
CR 3 R 4 R 5 phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R Ar ; NR 3a R 3b , OR 3c , S(O) k R 3d , k being 1, 2 or 3,

and
including their agriculturally acceptable salts.

First claim

The invention claimed is:

1. A diaminotriazine compound of formula (I)

wherein
A is a fused saturated or unsaturated, 5-or 6-membered carbocycle or a fused saturated or unsaturated, 5-or 6-membered heterocycle having 1, 2 or 3 heteroatoms or heteroatom moieties, selected from the group consisting of O, S, S(O) p , N and NR C as ring members,
wherein the carbocycle and the heterocycle are unsubstituted or carry 1, 2, 3 or 4 radicals R A ;
p is 0, 1 or 2
q is 0, 1, 2 or 3;
R A is selected from the group consisting of halogen, OH, CN, amino, NO 2 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, (C 1 -C 6 -alkoxy)-C 1 -C 6 alkyl, (C 1 -C 6 -alkoxy)-C 1 -C 6 -alkoxy, (C 1 -C 6 -alkoxy)-C 2 -C 6 -alkenyl, (C 1 -C 6 -alkoxy)-C 2 -C 6 -alkynyl, C 1 -C 6 -alkylthio, (C 1 -C 6 -alkyl)sulfinyl, (C 1 -C 6 -alkyl)sulfonyl, (C 1 -C 6 -alkyl)amino, di(C 1 -C 6 -alkyl)amino, (C 1 -C 6 -alkyl)-carbonyl, (C 1 -C 6 -alkoxy)-carbonyl, (C 1 -C 6 -alkyl)-carbonyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkyl, and (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkoxy, wherein the aliphatic and cycloaliphatic parts of the 22 aforementioned radicals are unsubstituted, partly or completely halogenated and wherein the cycloaliphatic parts of the last 4 mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups, it being possible that R A are identical or different, it being possible that two radicals R A which are bound at the same carbon atom may together be =0 or =NR d ;
R b is selected from the group consisting of halogen, OH, CN, amino, NO 2 , C 1 -C6-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, (C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, (C 1 -C 6 -alkoxy)-C 1 -C 6 -alkoxy, (C 1 -C 6 -alkoxy)-C 2 -C 6 -alkenyl, (C 1 -C 6 -alkoxy)-C 2 -C 6 -alkynyl, C 1 -C 6 -alkylthio, (C 1 -C 6 -alkyl)sulfinyl, (C 1 -C 6 -alkyl)sulfonyl, (C 1 -C 6 -alkyl)amino, di(C 1 -C 6 -alkyl)amino, (C 1 -C 6 -alkyl)-carbonyl, (C 1 -C 6 -alkoxy)-carbonyl, (C 1 -C 6 -alkyl)-carbonyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkyl, and (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkoxy, wherein the aliphatic and cycloaliphatic parts of the 22 aforementioned radicals are unsubstituted, partly or completely halogenated and wherein the cycloaliphatic parts of the last 4 mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups, for q =2 or 3 it being possible that R b are identical or different;
R c is selected from the group consisting of H, OH, S(0) 2 NH 2 , CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy, (C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, (C 1 -C 6 -alkyl)-carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)sulfonyl, (C 1 -C 6 -alkylamino)carbonyl, di(C 1 -C 6 -alkyl)aminocarbonyl, (C 1 -C 6 -alkylamino)sulfonyl, di(C 1 -C 6 -alkyl)aminosulfonyl and (C 1 -C 6 -alkoxy)sulfonyl, wherein the aliphatic and cycloaliphatic parts of the 16 aforementioned radicals are unsubstituted, partly or completely halogenated,
R d is selected from the group consisting of H, CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, and (C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, wherein the aliphatic and cycloaliphatic parts of the 8 aforementioned radicals are unsubstituted, partly or completely halogenated;
R l is selected from the group consisting of H, OH, S(O) 2 NH 2 , CN, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, (C3-C6-cycloalkyl)-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy, (C 1 -C 6 -alkoxy )-C 1 -C 6 -alkyl, (C 1 -C 6 alkyl)-carbonyl, (C 3 -C 6 -cycloalkyl)-carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)sulfonyl, (C 1 -C 6 -alkylamino)carbonyl, di(C 1 -C 6 -alkyl)aminocarbonyl, (C 1 -C 6 -alkylamino)sulfonyl, di(C 1 -C 6 -alkyl)aminosulfonyl and (C 1 -C 6 -alkoxy)sulfonyl, wherein the aliphatic and cycloaliphatic parts of the 17 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenyl-C 1 -C 6 -alkyl, phenylsulfonyl, phenylaminosulfonyl, phenylaminocarbonyl, phenyl(C 1 -C 6 -alkyl)aminocarbonyl, phenylcarbonyl and phenoxycarbonyl, wherein phenyl in the last 8 mentioned radicals are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy;
R 2 is selected from the group consisting of H, OH, S(0 ) 2 NH 2 , CN, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, (C3-C6-cycloalkyl)-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy, (C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl (C 1 -C 6 -alkyl)carbonyl, (C 3 -C 6 -cycloalkyl)-carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)sulfonyl, (C 1 -C 6 -alkylamino)carbonyl, di(C 1 -C 6 -alkyl)aminocarbonyl, (C 1 -C 6 -alkylamino)sulfonyl, di(C 1 -C 6 -alkyl)aminosulfonyl and (C 1 -C 6 -alkoxy)sulfonyl, wherein the aliphatic and cycloaliphatic parts of the 17 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenylsulfonyl, phenylaminosulfonyl, phenyl-C 1 -C 6 alkyl, phenoxy, phenylaminocarbonyl, phenyl(C 1 -C 6 -alkyl)aminocarbonyl, phenylcarbonyl and phenoxycarbonyl, wherein phenyl in the last 8 mentioned radicals is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy;
X is a radical selected from the group consisting of
CR 3 R 4 R 5
phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals
R Ar which are identical or different;
NR 3a R 3b ,
OR 3c and
S(O) k R 3d with k being 0,1 or 2 ,

wherein
R 3 is selected from the group consisting of H, halogen, OH, CN, C 1 -C 6 -alkyl, (C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkoxy, and (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkoxy, wherein the aliphatic and cycloaliphatic parts of the 9 aforementioned radicals are unsubstituted, partly or completely halogenated;
R 4 is selected from the group consisting of H, halogen, CN, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy;
R 5 is selected from the group consisting of halogen, CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkenyl and C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, wherein the aliphatic and cycloaliphatic parts of the 7 aforementioned radicals are unsubstituted, partly or completely halogenated;
R 4 and R 5 together with the carbon atom to which they are attached form a moiety selected from the group consisting of carbonyl, thiocarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, three- to six-membered saturated or partially unsaturated heterocyclyl, and the moiety >C═CR x R y , wherein R x and R y are selected from the group consisting of hydrogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl;
R Ar is selected from the group consisting of halogen, OH, CN, amino, NO 2 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, (C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, (C 1 -C 6 -alkoxy)-C 1 -C 6 -al

Assignees

• Basf Se

Inventors

• Major Julia
• Vogt Florian
• Calo Frederick
• Seitz Thomas
• Schachtschabel Doreen
• Newton Trevor William
• Hanzlik Kristin
• Hutzler Johannes
• Kreuz Klaus
• Tresch Stefan

Classifications

• A01N43/76

  1,3-Oxazoles; Hydrogenated 1,3-oxazoles · CPC title

• A01N43/68 Primary

  with two or three nitrogen atoms directly attached to ring carbon atoms · CPC title

• C07D251/18

  with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines · CPC title

• C07D405/12 Primary

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

• C07D405/14 Primary

  containing three or more hetero rings · CPC title