# US 8,541,594 B2 · Herbicides

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- Number: US 8,541,594 B2
- Document ID: US8541594B2
- Status: Granted
- Kind: B2
- Application number: 12/671,530
- Filed: 2008-07-30
- Published: 2012-02-16
- Granted: 2013-09-24
- Earliest claimed: 2007-08-01
- Assignees: Syngenta Limited
- Applicants: Stephane André Marie Jeanmart; Christopher John Mathews; John Benjamin Taylor; Steve Smith
- Inventors: Stephane André Marie Jeanmart; Christopher John Mathews; John Benjamin Taylor; Steve Smith
- Web page: https://patentgrep.com/patent/US8541594B2

## Abstract

Bicyclic dione compounds, and derivatives thereof, which are suitable for use as herbicides. formula (I)

## Claims

### Claim 1

A compound of formula I
wherein
R1 and R2 are independently of each other hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6haloalkenyloxy, C3-C6alkynyloxy, C1-C4alkoxyC1-C4alkyl, C1-C4alkoxyC1-C4alkoxy, C1-C4alkoxyC1-C4alkoxyC1-C4alkyl, C1-C6alkylthio, C1-C4alkylthioC1-C4alkyl, C1-C4alkylsulfinyl, C1-C4alkylsulfinylC1-C4alkyl, C1-C4alkylsulfonyl, C1-C4alkylsulfonylC1-C4alkyl, hydroxy-C1-C4alkyl, C1-C6haloalkoxyC1-C4alkyl, C3-C6alkenyloxyC1-C4alkyl, C3-C6haloalkenyloxyC1-C4alkyl, C3-C6alkynyloxyC1-C4alkyl, C1-C6cyanoalkyl, C1-C6cyanoalkoxy, C1-C4cyanoalkoxyC1-C4alkyl, hydroxy, C1-C6alkylcarbonyl, carboxy, C1-C6alkoxycarbonyl, C1-C6alkylaminocarbonyl, di-C1-C6alkylaminocarbonyl, tri(C1-C4alkyl)silyl or tri(C1-C4alkyl)silyloxy,
D is optionally substituted C1-C3alkylene,
E is optionally substituted C1-C3alkylene or optionally substituted C2-C3alkenylene,
Het is a an optionally substituted monocyclic or bicyclic heteroaromatic ring; and
G is hydrogen, an alkali metal, alkaline earth metal, sulfonium, ammonium or a latentiating group.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein R1 is hydrogen, C1-C4 alkyl or C1-C4alkoxy.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein R2 is hydrogen or methyl.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein D is C1-C2alkylene or C1-C2alkylene substituted by C1-C3 alkyl or C1-C3alkoxyC1-C3alkyl.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein E is optionally substituted C1-C2alkylene or optionally substituted C2alkenylene.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein Het is an optionally substituted monocyclic 5- or 6-membered nitrogen or sulfur containing heteroaromatic ring.

### Claim 7 (depends on 6)

The compound according to claim 6, wherein Het is a group of the formula R1 to R12
wherein
A designates the point of attachment to the ketoenol moiety,
W1 is N or CR6,
W2 and W3 are independently of each other N or CR4,
W4 is N or CR7,
with the proviso that at least one of W1, W2, W3 or W4 is N,
X is O, S, Se, or NR9,
Z is N or CR10 ,
wherein
R3 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C3-C6 cycloalkyl, C3-C6-halocycloalkyl, C2-C4alkenyl, C2-C4haloalkenyl, C2-C4alkynyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, nitro or cyano,
R4 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C5-C6cycloalkenyl, halogen, C1-C6alkoxy, C1-C6alkoxy-C1-C6alkyl, C1-C6haloalkoxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl or optionally substituted heteroaryloxy,
R5 is hydrogen, C1-C4 alkyl, C2-C3alkenyl, C2-C3alkynyl, C1-C4 haloalkyl or C2-C3 haloalkenyl,
R6 is hydrogen, methyl, halomethyl or halogen
R7 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl or cyano,
R8 is hydrogen, methyl, ethyl, halomethyl, haloethyl, optionally substituted aryl or optionally substituted heteroaryl,
R9 is hydrogen, methyl, ethyl or halomethyl, and
R10 is hydrogen, methyl, ethyl, halomethyl, haloethyl, halogen, cyano or nitro.

### Claim 8 (depends on 7)

The compound according to claim 7, wherein Het is a group of the formula R2
wherein X is sulphur, Z is nitrogen or CR10 and R3, R4 and R10 have the meanings assigned to them in claim 7.

### Claim 9 (depends on 1)

A process for the preparation of a compound of formula (G), which is a compound of the formula I as defined in claim 1, wherein G is hydrogen, Het is a group of the formula R2
wherein A designates the point of attachment to the ketoenol moiety of formula I,
X is O, S, Se, or NR9,
Z is N or CR10,
R9 is hydrogen, methyl, ethyl or halomethyl,
R10 is hydrogen, methyl, ethyl, halomethyl, haloethyl, halogen, cyano or nitro,
R1, R2, E and D have the meaning assigned to them in claim 1,
R3 is CH2R″,
R″ is hydrogen, alkyl or halogenoalkyl, and
R4 is hydrogen, C1-C6alkyl, C1-C6 haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C3-C6 cycloalkyl, C5-C6cycloalkenyl, halogen, C1-C6alkoxy-C1-C6alkyl, C1-C6haloalkoxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl or optionally substituted heteroaryloxy, which comprises the thermal rearrangement optionally in the presence of a suitable solvent and optionally under microwave irradiation of the compound of the formula (H) into a compound of formula (G)

### Claim 10 (depends on 1)

A process for the preparation of a compound of formula (J), which is a compound of the formula I as defined in claim 1, wherein G is hydrogen, Het is a group of the formula R3
wherein A designates the point of attachment to the ketoenol moiety of formula I,
X is O, S, Se, or NR9,
Z is N or CR10,
R9 is hydrogen, methyl, ethyl or halomethyl,
R10 is hydrogen, methyl, ethyl, halomethyl, haloethyl, halogen, cyano or nitro,
R1, R2, E and D have the meaning assigned to them in claim 1,
R3 is CH2R″,
R″ is hydrogen, alkyl or halogenoalkyl, and
R4 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C3-C6 cycloalkyl, C5-C6cycloalkenyl, halogen, C1-C6alkoxy, C1-C6alkoxy-C1C6alkyl, C1-C6haloalkoxy, optionall substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl or optionally substituted heteroaryloxy, which comprises the thermal rearrangement optionally in the presence of a suitable solvent and optionally under microwave irradiation of the compound of the formula (K) into a compound of formula (J)

### Claim 11 (depends on 1)

A method of controlling grasses and weeds in crops of useful plants, which comprises applying a herbicidally effective amount of a compound of formula I, as defined in claim 1, or of a composition comprising such a compound, to the plants or to the locus thereof.

### Claim 12 (depends on 1)

A herbicidal composition comprising:
a compound of formula I according to claim 1; and
a formulation adjuvant.

### Claim 13 (depends on 12)

The composition according to claim 12, which, in addition to comprising the compound of formula I, comprises a further herbicide as mixing partner.

### Claim 14 (depends on 12)

The composition according to claim 12, which, in addition to comprising the compound of formula I, comprises a safener.

### Claim 15 (depends on 12)

The composition according to claim 12, which, in addition to comprising the compound of formula I, comprises a further herbicide as mixing partner and a safener.