# US 5,346,881 A · 2-(bicyclic heterocyclyl)-6-fluoroalkyluracils

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- Number: US 5,346,881 A
- Document ID: US5346881A
- Status: Granted
- Kind: A
- Application number: 08/107,097
- Filed: 1993-08-13
- Granted: 1994-09-13
- Earliest claimed: 1993-08-13
- Assignees: FMC Corporation
- Inventors: George Theodoridis
- Web page: https://patentgrep.com/patent/US5346881A

## CPC

- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

Herbicidal 3-(bicyclic heterocyclyl)-6-fuoroalkyluracils of the formula ##STR1## in which M is fluoroalkyl(C.sub.1-6); R is hydrogen, alkyl(C.sub.1-6), 2-alkynyl(C.sub.3-6); 2-alkenyl(C.sub.3-6,), or cyanoalkyl(C.sub.1-6); R.sup.1 is hydrogen or alkyl(C.sub.1-6); R.sup.2 is hydrogen or alkyl (C.sub.1-6); Y is hydrogen, fluorine, chlorine, or bromine; X is hydrogen, fluorine, chlorine, bromine, cyano, alkyl(C.sub.1-6), or fluoroalkyl(C.sub.1-6); and n is 0 or 1.

## Claims

### Claim 1

A compound of the formula: ##STR4## in which M is fluoroalkyl(C.sub.1-6); R is hydrogen, alkyl(C.sub.1-6), 2-alkynyl(C.sub.3-6); 2-alkenyl(C.sub.3-6,), or cyanoalkyl(C.sub.1-6); R.sup.1 is hydrogen or alkyl(C.sub.1-6); R.sup.2 is hydrogen or alkyl(C.sub.1-6); Y is hydrogen, fluorine, chlorine, or bromine; X is hydrogen, fluorine, chlorine, bromine, cyano, alkyl(C.sub.1-6), or fluoroalkyl(C.sub.1-6); and n is 0 or 1.

### Claim 2 (depends on 1)

A compound of claim 1 in which
M is fluoroalkyl(C.sub.1-3); R is hydrogen, alkyl(C.sub.1-3), 2-alkynyl(C.sub.3-4); 2-alkenyl(C.sub.3-4), or cyanoalkyl(C.sub.1-3); R.sup.1 is hydrogen or alkyl(C.sub.1-3); R.sup.2 is hydrogen or alkyl(C.sub.1-3); Y is hydrogen, fluorine, chlorine, or bromine; X is hydrogen, fluorine, chlorine, bromine, cyano, alkyl(C.sub.1-3), or fluoroalkyl(C.sub.1-3); and n is 0 or 1.

### Claim 3 (depends on 2)

A compound of claim 2 in which M is fluoromethyl or fluoroethyl; R is hydrogen, methyl, ethyl, 2-alkynyl(C.sub.3), 2-alkenyl(C.sub.3), or cyanomethyl; R.sup.1 is hydrogen, methyl, or ethyl; R.sup.2 is hydrogen, methyl, or ethyl; Y is hydrogen, fluorine, chlorine, or bromine; X is hydrogen, fluorine, chlorine, bromine, cyano, methyl, or fluoromethyl; and n is 0 or 1.

### Claim 4 (depends on 3)

A compound of claim 3 in which M is trifluoromethyl or pentafluoroethyl; R is methyl; R.sup.1 is hydrogen, methyl, or ethyl; R.sup.2 is hydrogen, methyl, or ethyl; Y is hydrogen, fluorine, or chlorine; X is chlorine or bromine; and n is 0 or 1.

### Claim 5 (depends on 4)

A compound of claim 4 in which M is trifluoromethyl; R is methyl; R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or methyl; X is chlorine or bromine; Y is hydrogen, fluorine, or chlorine; and n is 0 or 1.

### Claim 6 (depends on 1)

The compound of claim 1 which is 3-(7-chloro-2,2-dimethyl-5-fluoro- 1,3-benzodioxol-4-yl)- 1 -methyl-6-trifluoromethyluracil.

### Claim 7 (depends on 1)

The compound of claim 1 which is 3-(7-bromo-2,2-dimethyl-5-fluoro- 1,3-benzodioxol-4yl)- 1 -methyl-6-trifluoromethyluracil.

### Claim 8 (depends on 1)

The compound of claim 1 which is 3-(8-chloro-1,4-benzodioxan-5-yl)- 1 -methyl-6-trifluoromethyluracil.

### Claim 9 (depends on 1)

The compound of claim 1 which is 3-(8-bromo-6-fluoro-1,4-benzodioxan-5-yl)- 1 -methyl-6-trifluoromethyluracil.

### Claim 10 (depends on 1)

The compound of claim 1 which is 3-(6,8-dichloro-1,4-benzodioxan-5-yl)- 1 -methyl-6-trifluoromethyluracil.

### Claim 11 (depends on 1)

The compound of claim 1 which is 3-(7-chloro-2,2-dimethyl-1,3-benzodioxol-4-yl)- 1 -methyl-6-trifluoromethyluracil.

### Claim 12 (depends on 1)

A composition for controling undesired plant growth comprising an herbicidally effective amount of a compound of claim 1 in admixture with an agriculturally acceptable carrier.

### Claim 13 (depends on 12)

A method for controlling undesired plant growth which comprises applying to a locus where control is desired, an herbically effective amount of the composition of claim 12.