Diaminotriazine derivatives as herbicides

Patent metadata

Field	Value
Publication number	US-10941122-B2
Application number	US-201515302681-A
Country	US
Kind code	B2
Filing date	Apr 9, 2015
Priority date	Apr 11, 2014
Publication date	Mar 9, 2021
Grant date	Mar 9, 2021

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
q is 0, 1, 2 or 3
R a is selected from the group consisting of C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkylthio, (C 1 -C 6 -haloalkyl)sulfinyl, (C 1 -C 6 -haloalkyl)-carbonyl, etc.;
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, etc.;
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, etc.;
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, etc.;
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, etc.;
R 4 is H, halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, 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, etc.; or
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 -cycloalkan-1,1-diyl, ipso-C 3 -C 6 -cycloalkendiyl, three- to six-membered saturated or partially unsaturated ipso-heterocyclodiyl;
including their agriculturally acceptable salts.

First claim

The invention claimed is:

1. A diaminotriazine compound of formula (I)

wherein
q is 0, 1, or 2;
R a is selected from the group consisting of C3-C6-cycloalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, and (C3-C6-cycloalkyl)-C 1 -C 4 -alkoxy;
R b is selected from the group consisting of halogen;
R 1 is selected from the group consisting of H, C 1 -C 6 -alkyl, (C 1 -C 6 -alkyl)carbonyl, and (C 1 -C 6 -alkoxy)carbonyl;
R 2 is selected from the group consisting of H, C 1 -C 6 -alkyl, (C 1 -C 6 -alkyl)carbonyl, and (C 1 -C 6 -alkoxy)carbonyl;
R 3 is selected from the group consisting of H, fluorine, chlorine, C 1 -C 4 -alkyl, and C 1 -C 4 -alkoxy;
R 4 is selected from the group consisting of H, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy, and C 1 -C 6 -haloalkoxy;
R 5 is selected from the group consisting of 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 C1-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; or
R 4 and R 5 together with the carbon atom to which they are attached may form a moiety selected from the group consisting of carbonyl, C 3 -C 6 -cycloalkan-1,1-diyl, ipso-C 3 -C 6 -cycloalkendiyl, three- to six-membered saturated or partially unsaturated ipso-heterocyclodiyl, where the carbocycle and the heterocycle are unsubstituted, partly or completely halogenated or carry from 1 to 6 C 1 -C 6 -alkyl groups, 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;
including their agriculturally acceptable salts.

2. The compound of claim 1 , wherein R b is fluorine.

3. The compound of claim 1 , wherein the moiety

is represented by the moiety

wherein
R a is as defined in claim 1 and wherein R b1 , R b2 and R b3 are identical or different and are hydrogen or have one of the meanings of R b defined in claim 1 .

4. The compound of claim 3 , wherein R b1 , R b2 and R b3 are selected from the group consisting of hydrogen and fluorine.

5. The compound of claim 1 , wherein the moiety

is selected from the group consisting of 2-fluoro-6-(cyclopropyloxy)phenyl, 2-fluoro-6-(cyclobutyloxy)phenyl, 2-fluoro-6-(cyclopentyloxy)phenyl, 2-fluoro-6-(cyclohexyloxy) phenyl, 2-fluoro-6-[(cyclopropyl)methyloxy]phenyl, 2-fluoro-6-[(cyclobutyl)methyloxy]phenyl, 2-fluoro-6-[(cyclopentyl)methyloxy]phenyl, 2-fluoro-6-[(cyclohexyl)methyloxy]phenyl, 2-fluoro-6-prop-2-enoxyphenyl, 2-fluoro-6-prop-2-ynoxyphenyl, 2,3-difluoro-6-(cyclopropyloxy)phenyl, 2,3-difluoro-6-(cyclobutyloxy)phenyl, 2,3-difluoro-6-(cyclopentyloxy)phenyl, 2,3-difluoro-6-(cyclohexyloxy)phenyl, 2,3-difluoro-6-[(cyclopropyl)methyloxy]phenyl, 2,3-difluoro-6-[(cyclobutyl)methyloxy]phenyl, 2,3-difluoro-6-[(cyclopentyl)methyloxy]phenyl, 2,3-difluoro-6-[(cyclohexyl)methyloxy]phenyl, 2,3-difluoro-6-prop-2-enoxyphenyl, 2,3-difluoro-6-prop-2-ynoxyphenyl, 2,4-difluoro-6-(cyclopropyloxy) phenyl, 2,4-difluoro-6-(cyclobutyloxy)phenyl, 2,4-difluoro-6-(cyclopentyloxy)phenyl, 2,4-difluoro-6-(cyclohexyloxy)phenyl, 2,4-difluoro-6-[(cyclopropyl)methyloxy]phenyl, 2,4-difluoro-6-[(cyclobutyl)methyloxy]phenyl, 2,4-difluoro-6-[(cyclopentyl)methyloxy]phenyl, 2,4-difluoro-6-[(cyclohexyl)methyloxy]phenyl, 2,4-difluoro-6-prop-2-enoxyphenyl, 2,4-difluoro-6-prop-2-ynoxyphenyl, 2,5-difluoro-6-(cyclopropyloxy)phenyl, 2,5-difluoro-6-(cyclobutyloxy)phenyl, 2,5-difluoro-6-(cyclopentyloxy)phenyl, 2,5-difluoro-6-(cyclohexyloxy)phenyl, 2,5-difluoro-6-[(cyclopropyl)methyloxy]phenyl, 2,5-difluoro-6-[(cyclobutyl)methyloxy]phenyl, 2,5-difluoro-6-[(cyclopentyl)methyloxy]phenyl, 2,5-difluoro-6-[(cyclohexyl)methyloxy]phenyl, 2,5-difluoro-6-prop-2-enoxyphenyl, 2,5-difluoro-6-prop-2-ynoxyphenyl, 2,3,5-trifluoro-6-(cyclopropyloxy)phenyl, 2,3,5-trifluoro-6-(cyclobutyloxy)phenyl, 2,3,5-trifluoro-6-(cyclopentyloxy)phenyl, 2,3,5-trifluoro-6-(cyclohexyloxy)phenyl, 2,3,5-trifluoro-6-[(cyclopropyl)methyloxy]phenyl, 2,3,5-trifluoro-6-[(cyclobutyl)methyloxy]phenyl, 2,3,5-trifluoro-6-[(cyclopentyl) methyloxy]phenyl, 2,3,5-trifluoro-6-[(cyclohexyl)methyloxy]phenyl, 2,3,5-trifluoro-6-prop-2-enoxyphenyl, 2,3,5-trifluoro-6-prop-2-ynoxyphenyl, 2,4,5-trifluoro-6-(cyclopropyloxy)phenyl, 2,4,5-trifluoro-6-(cyclobutyloxy)phenyl, 2,4,5-trifluoro-6-(cyclopentyloxy)phenyl, 2,4,5-trifluoro-6-(cyclohexyloxy)phenyl, 2,4,5-trifluoro-6-[(cyclopropyl)methyloxy]phenyl, 2,4,5-trifluoro-6-[(cyclobutyl)methyloxy]phenyl, 2,4,5-trifluoro-6-[(cyclopentyl)methyloxy]phenyl, 2,4,5-trifluoro-6-[(cyclohexyl)methyloxy]phenyl, 2,4,5-trifluoro-6-prop-2-enoxyphenyl, 2,4,5-trifluoro-6-prop-2-ynoxyphenyl, 2,3,4-trifluoro-6-(cyclopropyloxy)phenyl, 2,3,4-trifluoro-6-(cyclobutyloxy)phenyl, 2,3,4-trifluoro-6-(cyclopentyloxy)phenyl, 2,3,4-trifluoro-6-(cyclohexyloxy)phenyl, 2,3,4-trifluoro-6-[(cyclopropyl)methyloxy]phenyl, 2,3,4-trifluoro-6-[(cyclobutyl)methyloxy]phenyl, 2,3,4-trifluoro-6-[(cyclopentyl)methyloxy]phenyl, 2,3,4-trifluoro-6-[(cyclohexyl)methyloxy]phenyl, 2,3,4-trifluoro-6-prop-2-enoxyphenyl, and 2,3,4-trifluoro-6-prop-2-ynoxyphenyl.

6. The compound of claim 1 , wherein R 1 is H, C 1 -C 4 -alkyl, or (C 1 -C 4 -alkyl)carbonyl.

7. The compound of claim 6 , wherein R 1 is H.

8. The compound of claim 1 , wherein R 2 is H, C 1 -C 4 -alkyl, or (C 1 -C 4 -alkyl)carbonyl.

9. The compound of claim 8 , wherein R 2 is H.

10. The compound of claim 1 , wherein R 4 is selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, and C 1 -C 6 -haloalkoxy.

11. The compound of claim 1 , wherein R 5 is selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, and C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl.

12. The compound of claim 1 , wherein R 4 and R 5 together with the carbon atom to which they are attached form a moiety selected from the group consisting of C 3 -C 6 -cycloalkan-1,1-diyl, ipso-C 3 -C 6 -cycloalkendiyl and three- to six-membered saturated or partially unsaturated ipso-heterocyclodiyl.

13. The compound of claim 1 , wherein the combination of R 3 , R 4 , and R 5 are as given in the following table, where a merged column for R 4 and R 5 indicates that R 4 and R 5 together with the carbon atom to which they are attached correspond to the specified group:

#
R 3
R 4
R 5

3
F
H
CH 3

4
F
CH 3
CH 3

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

• C07D251/48

  Two nitrogen atoms · CPC title

• A01N43/68

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

• C07D251/18 Primary

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