Herbicidal azines

Patent metadata

Field	Value
Publication number	US-9549558-B2
Application number	US-201314437981-A
Country	US
Kind code	B2
Filing date	Oct 22, 2013
Priority date	Oct 24, 2012
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

The present invention relates to azines of formula (I)

wherein the variables are defined according to the description,
processes and intermediated for preparing them, compositions comprising them and their use as herbicides, i.e. for controlling harmful plants and a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one azine of the formula I to act on plants, their seed and/or their habitat.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
A is 2-fluoro-phenyl, which is substituted by one to four substituents selected from the group consisting of halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, OH, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, (C 1 -C 6 -alkyl)sulfinyl, (C 1 -C 6 -alkyl)sulfonyl, amino, (C 1 -C 6 -alkyl)amino, di(C 1 -C 6 -alkyl)amino, (C 1 -C 6 -alkyl)carbonyl and (C 1 -C 6 -alkoxy)carbonyl;
R 1 H, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)sulfonyl or phenylsulfonyl,
wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy;

R 2 H, halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, OH, C 1 -C 6 -alkoxy or C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl;
R 3 H, halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy;
R 4 H, halogen, CN, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; or
R 3 and R 4 together with the carbon atom to which they are attached form a moiety selected from the group consisting of carbonyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl and three- to six-membered heterocyclyl,
wherein the C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl or and three- to six-membered heterocyclyl is unsubstituted or substituted by one to three substituents selected from halogen, CN, C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy; and

R 5 H, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)sulfonyl or phenylsulfonyl,
wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy;

including their agriculturally acceptable salts or N-oxides.

2. The compound of claim 1 , wherein A is 2-fluoro-phenyl, which is substituted by one to three substituents selected from the group consisting of halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, OH, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, (C 1 -C 6 -alkyl)sulfinyl, (C 1 -C 6 -alkyl)sulfonyl, amino, (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.

3. The compound of claim 1 , wherein R 1 and R 5 independently of one another are H, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, (C 1 -C 6 -alkyl)carbonyl or (C 1 -C 6 -alkyl)sulfonyl.

4. The compound of claim 1 , wherein R 2 is H, halogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl.

5. The compound of claim 1 , wherein A is 2-fluoro-phenyl, which is substituted by one to three substituents selected from the group consisting of halogen, CN, C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy.

6. A process for the compound of claim 1 , wherein R 1 and R 5 independently of one another are H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy;
comprising reacting biguanidines of formula (II)

wherein R 1 and R 5 independently of one another are H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy;

with carbonyl compounds of formula (III)

wherein
L 1 is halogen, CN, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyloxy or C 1 -C 6 -alkoxycarbonyloxy;

in the presence of a base.

7. A process for the preparation of the compound of claim 1 , wherein
R 1 and R 5 independently of one another are H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy;
comprising reacting halotriazines of formula (VI),

wherein R 5 is H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy; and
Hal is halogen;

with an amine of formula (V),
A-NHR 1   (V)

wherein R 1 is H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy;

in the presence of a base and a catalyst.

8. A process for the preparation of the compound of claim 1 , wherein
R 5 is CN, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)sulfonyl or phenylsulfonyl,
wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy;

comprising reacting an azine of formula (I), wherein R 5 is hydrogen,
with a compound of formula (IX)
R 5 —X  (IX)

wherein
R 5 is CN, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)sulfonyl or phenylsulfonyl,
wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy; and

X is halogen or oxycarbonyl-C 1 -C 6 -alkyl.

9. A process for the preparation of a compound of claim 1 , wherein
R 1 is CN, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)sulfonyl or phenylsulfonyl,
wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy;

comprising reacting an azine of formula (I), wherein R 1 is hydrogen,
with a compound of formula (X)
R 1 —X  (X)

wherein
R 1 is CN, (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)sulfonyl or phenylsulfonyl,
wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy; and

X is halogen or oxycarbonyl-C 1 -C 6 -alkyl.

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

11. A process for the preparation of herbicidal active agrochemical compositions, which comprises mixing an herbicidally active amount of at least a compound of claim 1 and at least one inert liquid and/or solid carrier and, if desired, at least one surface-active substance.

12. A method of controlling undesired vegetation, which comprises allowing an herbicidally active amount of at least a compound of claim 1 to act on plants, their environment or on seed.

13. A method for the desiccation/defoliation of plants, which comprises allowing at least a compound of claim 1 to act on plants.

14. The method of claim 12 , wherein, in the compound of formula (I), A is 2-fluoro-phenyl, which is substituted by one to three substituents selected from the group consisting of halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, OH, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, (C 1 -C 6 -alkyl)sulfinyl, (C 1 -C 6 -alkyl)sulfo

Assignees

• Basf Se

Inventors

• Newton Trevor William
• Vogt Florian
• Major Julia
• Hanzlik Kristin
• Parra Rapado Liliana
• Kordes Markus
• Seitz Thomas
• Witschel Matthias
• Kreuz Klaus
• Hutzler Johannes
• Evans Richard Roger
• Lerchl Jens

Classifications

• C07D251/22

  to two ring carbon atoms · CPC title

• C07C279/26

  X and Y being nitrogen atoms, i.e. biguanides · CPC title

• A01N43/68 Primary

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

• C07D251/48

  Two nitrogen atoms · CPC title

• C07D251/42 Primary

  One nitrogen atom · CPC title