# US 11,992,012 B2 · Diaminotriazine compounds

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- Number: US 11,992,012 B2
- Document ID: US11992012B2
- Status: Granted
- Kind: B2
- Application number: 17/270,884
- Filed: 2019-09-09
- Published: 2021-06-24
- Granted: 2024-05-28
- Earliest claimed: 2018-09-18
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Danny Geerdink; Florian Vogt; Thomas Zierke; Martin Hartmueller; Trevor William Newton; Klaus Reinhard; Thomas Seitz
- Web page: https://patentgrep.com/patent/US11992012B2

## CPC

- A01N 43/68: with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N 43/76: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01N 43/82: five-membered rings with three ring hetero atoms
- C07D 251/18: with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## 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.

## Claims

### Claim 1

A diaminotriazine compound of formula (I)
wherein
q is 0, 1, 2, or 3
Q is O,
wherein
Ra is selected from the group consisting of halogen, CN, C1-C4-alkyl, and C1-C4-alkoxy, where the radicals are unsubstituted, partly or completely halogenated;
Rb is selected from the group consisting of halogen, CN, C1-C4-alkyl, and C1-C4-alkoxy, where the aliphatic parts of the radicals are unsubstituted, partly or completely halogenated,
for q=2 or 3 it being possible that Rb are identical or different;
R1 is selected from the group consisting of H and C1-C6-alkyl;
R2 is selected from the group consisting of H, halogen, OH, CN, C1-C6-alkyl, (C1-C6-alkoxy)-C1-C6-alkyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkoxy, (C3-C6-cycloalkyl)-C1-C4-alkoxy, where the aliphatic and cycloaliphatic parts of the radicals are unsubstituted, partly or completely halogenated;
R3 is selected from the group consisting of H, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
R4 is selected from the group consisting of halogen, CN, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, C3-C6-cycloalkenyl and C1-C6-alkoxy-C1-C6-alkyl, where the aliphatic and cycloaliphatic parts of the radicals are unsubstituted, partly or completely halogenated;
R3 and R4 together with the carbon atom to which they are attached form a moiety selected from the group consisting of carbonyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, three- to six-membered saturated or partially unsaturated heterocyclyl, and the moiety >C═CRxRy, where Rx and Ry are hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl or CRxRy form a 3 to 6 membered cycloalkyl;
R5 is selected from the group consisting of H and C1-C6-alkyl;
R6 is phenyl, which is unsubstituted or carries 1, 2, 3, 4, or 5 radicals R6A which are selected from the group consisting of halogen, OH, CN, amino, NO2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, (C1-C6-alkoxy)-C1-C6-alkyl, (C1-C6-alkoxy)-C1-C6-alkoxy, (C1-C6-alkoxy)-C2-C6-alkenyl, (C1-C6-alkoxy)-C2-C6-alkynyl, C1-C6-alkylthio, (C1-C6-alkyl)sulfinyl, (C1-C6-alkyl)sulfonyl, (C1-C6-alkyl)amino, di(C1-C6-alkyl)amino, (C1-C6-alkyl)-carbonyl, (C1-C6-alkoxy)-carbonyl, (C1-C6-alkyl)-carbonyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, (C3-C6-cycloalkyl)-C1-C4-alkyl, (C3-C6-cycloalkyl)-C1-C4-alkoxy, where the aliphatic and cycloaliphatic parts of the radicals are unsubstituted, partly or completely halogenated and where the cycloaliphatic parts of the radicals may carry 1, 2, 3, 4, 5, or 6 methyl groups,
it being possible that R6A are identical or different;
R7 and R7′ are independently selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-halogenoalkoxy, and C3-C6-cycloalkyl;
including their agriculturally acceptable salts.

### Claim 2 (depends on 1)

The compound of claim 1, wherein Ra is fluorine or chlorine.

### Claim 3 (depends on 1)

The compound of claim 1, wherein Rb is fluorine, chlorine, bromine, or methyl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Rt is.

### Claim 5 (depends on 1)

The compound of claim 1, wherein
R2 is selected from the group consisting of hydrogen, fluorine, C1-C4-alkyl and C1-C4-alkoxy;
R3 is selected from the group consisting of hydrogen, fluorine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C6-haloalkoxy;
R4 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, and C1-C6-alkoxy-C1-C6-alkyl; or
R3 and R4 together with the carbon atom to which they are attached form a moiety selected from the group consisting of C3-C6-cycloalkyl, C3-C6-cycloalkenyl and three- to six-membered saturated or partially unsaturated heterocyclyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R5 is.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R6A, if present, is selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C3-C6-cycloalkyl.

### Claim 8 (depends on 1)

An agrochemical composition comprising a herbicidal active amount of at least one compound as claimed in claim 1 and at least one inert liquid and/or solid carrier and, optionally, at least one surface-active substance.

### Claim 9 (depends on 1)

A method of controlling unwanted vegetation comprising applying a compound as claimed in claim 1 to a plant for desiccation/defoliation of the plant.