Diaminotriazine derivatives as herbicides

Patent metadata

Field	Value
Publication number	US-9822082-B2
Application number	US-201515302733-A
Country	US
Kind code	B2
Filing date	Apr 9, 2015
Priority date	Apr 11, 2014
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

The present invention relates to diaminotriazine compounds of the formula (I) 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 phenyl, which is substituted by fluorine in the ortho-position and which may additionally carry 1, 2, 3 or 4 identical or different substituents R A ;
R 1 , R 2 are inter alia H, OH, S(O) 2 NH 2 , CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, etc.
R 3 is selected from the group consisting of 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 -alkyl, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkylamino)carbonyl and di(C 1 -C 6 -alkyl)aminocarbonyl, where the aliphatic and cycloaliphatic parts of the 9 aforementioned radicals are unsubstituted, partly or completely halogenated,
R 4 and R 5 , together with the carbon atom, to which they are bound form a saturated 3-, 4-, 5- or 6-membered carbocyclic radical or a saturated 3-, 4-, 5- or 6-membered heterocyclic radical, where the carbocyclic radical and the heterocyclic radical are unsubstituted, partly or completely halogenated or carry from 1 to 6 C 1 -C 6 -alkyl groups;
including their agriculturally acceptable salts.

First claim

The invention claimed is:

1. A diaminotriazine compound of formula (I)

wherein
A is phenyl, which is substituted by fluorine in the ortho-position and which may additionally carry 1, 2, 3 or 4 identical or different substituents R A 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 -alkyl, (C 1 -C 6 -alkoxy)-C 2 -C 6 -alkenyl, (C 1 -C 6 -alkoxy)-C 2 -C 6 -alkynyl, (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 3 -C 6 -cycloalkyl, (C 3 -C 6 -cycloalkyl)-C 1 -C 4 -alkyl, where the aliphatic and cycloaliphatic parts of the 11 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;
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 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 14 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenyl-C 1 -C 6 -alkyl, phenylsulfonyl, phenylaminosulfonyl, phenylcarbonyl and phenoxycarbonyl,
wherein phenyl in the last 6 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 -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 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 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 14 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenylsulfonyl, phenylaminosulfonyl, phenyl-C 1 -C 6 alkyl, phenoxy, phenylcarbonyl and phenoxycarbonyl,
wherein phenyl in the last 6 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 -alkoxy and C 1 -C 6 -haloalkoxy;

R 3 is selected from the group consisting of 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 -alkyl, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkylamino)carbonyl and di(C 1 -C 6 -alkyl)aminocarbonyl, where the aliphatic and cycloaliphatic parts of the 9 aforementioned radicals are unsubstituted, partly or completely halogenated,
R 4 and R 5 , together with the carbon atom, to which they are bound form a saturated 3-, 4-, 5- or 6-membered carbocyclic radical or a saturated 3-, 4-, 5- or 6-membered heterocyclic radical, where the carbocyclic radical and the heterocyclic radical are unsubstituted, partly or completely halogenated or carry from 1 to 6 C 1 -C 6 -alkyl groups;
including their agriculturally acceptable salts.

2. The compound of claim 1 , wherein A is phenyl, which carries a fluorine atom in the 2-position of the phenyl ring and which further carries 1, 2, 3 or 4 identical or different substituents R A .

3. The compound of claim 2 , wherein R A is halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkynyl or C 2 -C 6 -alkenyl.

4. The compound of claim 3 , wherein A is phenyl, which carries a fluorine atom in the 2-position of the phenyl ring and which further carries 1, 2, 3 or 4 substituents R A selected from the group consisting of F, Cl, Br, CN, CF 3 , methyl, vinyl, ethynyl and cyclopropyl.

5. The compound of claim 4 , wherein A is 2,6-difluorophenyl, 2,3,6-trifluorophenyl, 2,4,6-trifluorophenyl, 2,3,5,6-tetrafluorophenyl or 2,3,4,5,6-pentafluorophenyl.

6. The compound of claim 1 , wherein R 1 is selected from the group consisting of H, CN, C 1 -C 6 -alkyl, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkyl)sulfonyl, C 1 -C 6 -alkoxy, (C 1 -C 6 -alkoxy)carbonyl, (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, where the aliphatic parts of the 10 aforementioned radicals are unsubstituted, partly or completely halogenated,
phenyl, phenylcarbonyl and phenyl-C 1 -C 6 alkyl,
wherein phenyl in the last 3 mentioned radical 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.

7. The compound of claim 1 , wherein R 2 is selected from the group consisting of H, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -haloalkyl)carbonyl, (C 1 -C 6 -alkyl)sulfonyl or (C 1 -C 6 -haloalkyl)sulfonyl.

8. The compound of claim 1 , wherein R 2 is selected from the group consisting of H, CN, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkyl)sulfonyl, C 1 -C 6 -alkoxy, (C 1 -C 6 -alkoxy)carbonyl, (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, where the aliphatic parts of the 10 aforementioned radicals are unsubstituted, partly or completely halogenated,
phenyl, phenylcarbonyl and C 1 -C 6 alkylphenyl,
wherein phenyl in the last 3 mentioned radical 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 -alkoxy and C 1 -C 6 -alkoxy.

9. The compound of claim 1 , wherein R 2 is selected from the group consisting of H, CN, (C 1 -C 6 -alkyl)carbonyl or (C 1 C 6 -alkyl)sulfonyl.

10. The compound of claim 1 , wherein R 1 is H.

11. The compound of claim 1 , wherein R 2 is H.

12. The compound of claim 1 , wherein R 3 is selected from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl.

13. The compound of claim 12 , wherein R 3 is methyl.

14. The compound of claim 1 , wherein R 4 and R 5 , together with the carbon atom, to which they are bound form cyclopropan-1,1-diyl, cyclobutan-1,1-diyl, cyclopentan-1,1-diyl or cyclohexan-1,1-diyl.

15. The compound of claim 1 wherein R 4 and R 5 , together with the carbon atom, to which they are bound form oxiran-2,2-diyl, oxetan-2,2-diyl, oxan-2,2-diyl or oxan-4,4-diyl.

16. The compound of claim 1 , wherein
R 1 is H;
R 2 is H;
R 3 is methyl; and
A is phenyl, which carries a fluorine atom in the 2-position of the phenyl ring and which further carries 1, 2, 3 or 4 identical or different substituents R A .

17. An agrochemical composition comprising a herbicidal active amount of at least one compound of claim 1 and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface-active substances.

18. A method of control

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

• A01N43/68

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

• C07D251/48

  Two nitrogen atoms · CPC title

• C07D251/18 Primary

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