Uracil compounds and use thereof

Details Uracil compounds and use thereof Uracil compounds and use thereof

2001-06-28

2002-06-11

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S312000, C544S314000

Reexamination Certificate

active

06403534

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to uracil compounds and herbicidal compositions comprising them as active ingredients.
2. Description of Related Art
Although numerous herbicides have been commercialized, the weeds that need to be controlled are varied and their germination lasts over a long period. Accordingly, new herbicides are needed that have a higher herbicidal activity and a wide herbicidal spectrum but do not cause phytotoxicity on crops.
U.S. Pat. No. 4,859,229 and WO 95/32952 disclose that certain kinds of phenyluracil compounds have an herbicidal activity. However, uracil compounds having improved herbicidal performance are desired.
The purpose of the invention is to provide compounds having excellent performance as a herbicide.
SUMMARY OF THE INVENTION
As the result of extensive studies seeking compounds having excellent performance as a herbicide, the present inventors have found that uracil compounds represented by the following formula [L] have an excellent performance as a herbicide and have completed the invention. Accordingly, the invention provides uracil compounds (hereinafter, referred to as the present compound) represented by the formula [L]:
wherein A
1
represents amino or C
1
-C
3
alkyl, A
2
represents C
1
-C
3
haloalkyl, X represents hydrogen or halogen, Y represents halogen,
R
1
represents —OR
21
, —ON(R
22
)R
23
, —ON═C(R
24
)R
25
, —SR
26
, —N(R
27
)R
28
, —N(R
29
)OR
30
, —N(R
31
)SO
2
R
32
or —N(R
33
)N(R
34
)R
35
,
(wherein R
21
represents hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
3
-C
6
cycloalkyl, carboxy C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
alkenyloxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
alkynyloxycarbonyl C
1
-C
6
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkyl, benzyl or phenyl (the benzyl and phenyl maybe substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy) or tetrahydrofuryl (the tetrahydrofuryl may be substituted with one or more of hydroxy, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy and C
1
-C
6
alkylcarbonyloxy),
R
22
and R
23
independently represent hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl or benzyl (the benzyl may be substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy),
R
24
and R
25
independently represent hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, benzyl or phenyl (the benzyl and phenyl may be substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy),
R
26
represents hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
3
-C
6
cycloalkyl, carboxy C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
alkenyloxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
alkynyloxycarbonyl C
1
-C
6
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkyl, benzyl or phenyl (the benzyl and phenyl maybe substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy),
R
27
represents hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
3
-C
6
cycloalkyl, carboxy C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
alkenyloxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
alkynyloxycarbonyl C
1
-C
6
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkyl, benzyl or phenyl (the benzyl and phenyl maybe substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy),
R
28
represents hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, benzyl or phenyl (the benzyl and phenyl may be substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy),
R
29
and R
30
independently represent hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl or benzyl (the benzyl may be substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy),
R
31
represents hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, benzyl or phenyl (the benzyl and phenyl may be substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy),
R
32
represents C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, benzyl or phenyl (the benzyl and phenyl may be substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy),
R
33
, R
34
and R
35
independently represent hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, benzyl or phenyl (the benzyl and phenyl may be substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy),
R
2
, R
3
, R
4
and R
5
independently represent hydrogen or C
1
-C
3
alkyl.
The present invention also provides a herbicidal composition comprising, as an active ingredient, such an uracil compound.
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, stereoisomers of the uracil compounds may exist with respect to a double bond or an asymmetric carbon atom. It will be appreciated that the present invention includes individual stereoisomers of the uracil compounds, as well as mixtures thereof.
In the present invention:
With regard to A
1
, C
1
-C
3
alkyl represents methyl, ethyl, propyl or isopropyl.
With regard to A
2
, C
1
-C
3
haloalkyl includes trifluoromethyl, difluoromethyl, fluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-difluoroethyl, 1-fluoroethyl, 2-fluoroethyl and the like.
With regard to R
2
, R
3
, R
4
and R
5
, C
1
-C
3
alkyl represents methyl, ethyl, propyl or isopropyl.
With regard to R
21
, C
1
-C
6
alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl (hereinafter “t” means “tertiary”, unless noted otherwise), pentyl, isopentyl, neopentyl, hexyl and the like;
C
1
-C
6
haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C
3
-C
6
alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C
3
-C
6
alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like;
C
3
-C
6
cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like;
carboxy C
1
-C
6
alkyl includes carboxymethyl, 1-carboxyethyl, 1-carboxy-1-methylethyl and the like;
C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl includes methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-methoxycarbonylethyl,
1-methoxycarbonyl-1-methylethyl, 1-ethoxycarbonylethyl and the like;
C
3
-C
6
alkenyloxycarbonyl C
1
-C
6
alkyl includes allyloxycarbonylmethyl, 1-allyloxycarbonylethyl, 2-allyloxycarbonylethyl, 1-allyloxycarbonyl-1-methylethyl and the like;
C
3
-C
6
alkynyloxycarbonyl C
1
-C
6
alkyl includes propargyloxycarbonylmethyl, 1-propargyloxycarbonylethyl, 2-propargyloxycarbonylethyl, 1propargyloxycarbonyl-1-methylethyl and the like;
C
1
-C
6
alkoxy C
1
-C
6
alkyl includes 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl and the like;
benzyl which may be substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like;
phenyl which may be substituted with one or more of halogen, C
1
-C
6
alkyl and C
1
-C
6
alkoxy includes phenyl, 4-chlorophenyl, p-tolyl, o-tolyl and the like; and
tetrahydrofuryl which may be substituted with one or more of hydroxy, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy and C
1
-C
6
alkylcarbonyloxy includes 3-tetrahydrofuryl, 4-hydroxy-3-tetrahydrofuryl, 4-methoxy-3-tetrahydrofuryl, 4-acetoxy-3-tetrahydrofuryl and the like.
With regard to R
22
and R
23
, C
1
-C
6
alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like;
C
1
-C
6
haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C
3
-C
6
alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and

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