Diaminotriazine compounds and their use as herbicides

Patent metadata

Field	Value
Publication number	US-10029992-B2
Application number	US-201515305827-A
Country	US
Kind code	B2
Filing date	Apr 22, 2015
Priority date	Apr 23, 2014
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

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

wherein
p is 1 or 2;
q is 0, 1, 2 or 3 provided that p+q is 1, 2, 3 or 4;
Q is inter alia a chemical bond, O, S(O) m , CR q1 R q2 , NR q3 , C(O), C(O)O,
Ar is phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R A
R a is inter alia hydrogen, halogen, OH, CN, amino, NO 2 , C 1 -C 6 -alkyl, etc;
R b is inter alia halogen, OH, CN, amino, NO 2 , C 1 -C 6 -alkyl, etc.;
R 1 and R 2 are inter alia H, OH, S(O) 2 NH 2 , CN, C 1 -C 6 -alkyl, 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
p is 1 or 2;
q is 0, 1, 2 or 3 provided that p+q is 1, 2, 3 or 4;
Q is a chemical bond, O, S(O) m , CR q1 R q2 , NR q3 , C(O), C(O)O, CR q1 R q2 —O, S(O) m NR q3 or C(O)NR q3 ,
wherein
m is 0, 1 or 2;
R q1 , R q2 are hydrogen, halogen or C 1 -C 4 -alkyl;
R q3 is H, CN, C 1 -C 6 -alkyl, (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, where the aliphatic parts of the 6 aforementioned radicals are unsubstituted, partly or completely halogenated;

Ar is phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R A which are 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, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkoxy, where the aliphatic and cycloaliphatic parts of the 22 aforementioned radicals are unsubstituted, partly or completely halogenated and where the cycloaliphatic parts of the last 4 mentioned radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups,
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,
it being possible that R A are identical or different;

R a is selected from the group consisting of hydrogen, 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 -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, where the aliphatic and cycloaliphatic parts of the 14 aforementioned radicals are unsubstituted, partly or completely halogenated;
R b 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, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkoxy, where the aliphatic and cycloaliphatic parts of the 22 aforementioned radicals are unsubstituted, partly or completely halogenated and where 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 1 is selected from the group consisting of 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, (C 1 -C 6 -alkoxy)-C 1 -C 6 -alkyl, (C 3 -C 6 -cycloalkyl)-carbonyl, (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, where the aliphatic and cycloaliphatic parts of the 15 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(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 3 -C 6 -cycloalkyl)-carbonyl 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, where the aliphatic and cycloaliphatic parts of the 15 aforementioned radicals are unsubstituted, partly or completely halogenated,
phenyl, phenylsulfonyl, phenylaminosulfonyl, phenylaminocarbonyl, phenyl(C 1 -C 6 -alkyl)aminocarbonyl, phenyl-C 1 -C 6 alkyl, phenoxy, phenylcarbonyl and phenoxycarbonyl,
wherein phenyl in the last 9 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 3 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, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkoxy, where 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 -alkyl, 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, where 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, 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 , where R x and R y are hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;
R Ar 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)

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
• Sisay Mihiret Tekeste

Classifications

• C07D251/18 Primary

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

• A01N43/68

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

• C07D251/48 Primary

  Two nitrogen atoms · CPC title