Herbicidal pyridazinone derivatives

Patent metadata

Field	Value
Publication number	US-9944608-B2
Application number	US-201515325816-A
Country	US
Kind code	B2
Filing date	Jul 10, 2015
Priority date	Jul 17, 2014
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

The present invention relates to herbicidal benzyloxy-substituted phenyl-diones and benzyloxy substituted phenyl-dioxo-thiazinone derivatives of formula (I), as well as to processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, such as broad-leaved dicotyledonous weeds, in crops of useful plants.

First claim

The invention claimed is:

1. A compound of formula (I)

or a salt or N-oxide thereof,
R 1 is selected from the group consisting of C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkoxy, C 1 -C 2 alkoxy-C 1 -C 2 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, cyano-C 1 -C 4 alkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl and C 2 -C 4 haloalkynyl;
R 2 is selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 3 haloalkoxy-C 1 -C 3 alkyl-, C 1 -C 6 alkoxy, C 1 -C 3 alkoxy-C 1 -C 3 alkyl, C 1 -C 3 alkoxy-C 1 -C 3 alkoxy-C 1 -C 3 alkyl-, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 1 -C 6 hydroxyalkyl-, C 1 -C 6 alkylcarbonyl-, C 1 -C 6 alkyl-S(O) m —, amino, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, —C(C 1 -C 3 alkyl)=N—O—C 1 -C 3 alkyl and C 2 -C 6 haloalkynyl;
G is hydrogen, or C(O)R 3 ;
X and Y are each independently hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen;
Z is C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen;
m is an integer of 0, 1, or 2;
n is an integer of 0, 1, 2, 3, 4, or 5;
R 3 is selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, C 1 -C 6 alkyl-S—, —NR 4 R 5 and phenyl optionally substituted by one or more R 6 ;
R 4 and R 5 are independently selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy, or R 4 and R 5 together can form a morpholinyl ring; and,
R 6 is selected from the group consisting of halogen, cyano, nitro, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy and C 1 -C 3 haloalkoxy,
wherein the compound of formula (I) can be in the following tautomeric forms when R 2 is hydrogen and G is hydrogen:

2. The compound according to claim 1 , wherein G is hydrogen or C(O)R 3 wherein R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy, or tert-butoxy.

3. The compound of claim 1 , wherein X is hydrogen, halogen, or C 1 haloalkyl.

4. The compound of claim 1 , wherein Y is hydrogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, or halogen.

5. The compound of claim 1 , wherein X is ortho with respect to the pyrdazinone/pyridazine-dione moiety.

6. The compound of claim 1 , wherein Y is ortho with respect to the benzyloxy moiety.

7. The compound of claim 1 , wherein R 1 is methyl, ethyl, n-propyl, cyclopropyl, propargyl, or C 1 haloalkyl.

8. The compound of claim 1 , wherein R 2 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 3 alkoxy-C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl and C 2 -C 6 haloalkynyl.

9. The compound of claim 1 , wherein R 2 is selected from the group consisting of, methyl, ethyl, cyclopropyl, trifluoromethyl and methoxymethyl.

10. The compound of claim 1 , wherein R 2 is cylcopropyl or methyl.

11. The compound of claim 1 , wherein each Z is independently selected from halogen, methyl, methoxy, and trifluoromethyl.

12. A herbicidal composition comprising a herbicidal compound according to claim 1 and an agriculturally acceptable formulation adjuvant.

13. The herbicidal composition according to claim 12 , further comprising at least one additional pesticide.

14. A method of controlling unwanted plant growth, the method comprising applying a compound of formula (I) as defined in claim 1 to the unwanted plants or to the locus thereof.

Assignees

• Syngenta Participations Ag

Inventors

• Shanahan Stephen Edward
• Burton Paul Matthew
• Egan Benjamin Andrew
• O'Riordan Timothy Jeremiah Cornelius

Classifications

• A01N43/58

  1,2-Diazines; Hydrogenated 1,2-diazines · CPC title

• C07D237/16 Primary

  Two oxygen atoms · CPC title