Uracil compounds and use thereof

Details Uracil compounds and use thereof Uracil compounds and use thereof

2002-07-12

2003-12-23

Shah, Mukund J. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C560S017000, C560S021000, C560S029000, C560S030000, C560S043000, C560S045000, C560S047000, C560S048000, C560S358000

Reexamination Certificate

active

06667413

ABSTRACT:

The present invention relates to uracil compounds and use thereof.
An object of the present invention is to provide compounds having excellent herbicidal activity.
Recently, a number of herbicides are commercially available and used. However, since there are many kinds of weeds to be controlled and generation thereof occurs over a long period of time, a herbicide is required having higher herbicidal effect, having wider herbicidal spectrum and causing no problem of phytotoxicity on crops.
U.S. Pat. No. 4,859,229 discloses that certain kinds of phenyluracil compounds have herbicidal activity, however, these phenyluracil compounds do not always have sufficient ability as a herbicide. Also WO 97/01541, and WO 98/41093 disclose that kinds of substituted phenoxyphenyl uracil compounds have herbicidal activity, however, the compounds do not always have sufficient ability as a herbicide.
The present inventors have intensively investigated to find compounds having excellent herbicidal activity, and resultantly, found that uracil compounds of the following formula [I] have excellent herbicidal activity, leading to completion of the present invention. Namely, the present invention provides uracil compounds [I] of the formula [I] (hereinafter, referred to as present compound):
wherein, W represents oxygen, sulfur, imino or C
1
to C
3
alkylimino, Y represents oxygen, sulfur, imino or C
1
to C
3
alkylimino, R
1
represents C
1
to C
3
alkyl or C
1
to C
3
haloalkyl, R
2
represents C
1
to C
3
alkyl, R
4
represents hydrogen or methyl, R
5
represents hydrogen, C
1
to C
6
alkyl, C
1
to C
6
haloalkyl, C
3
to C
6
alkenyl, C
3
to C
6
haloalkenyl, C
3
to C
6
alkynyl, or C
3
to C
6
haloalkynyl, X
1
represents halogen, cyano, or nitro, X
2
represents hydrogen or halogen, and each of X
3
and X
4
independently represents hydrogen, halogen, C
1
to C
6
alkyl, C
1
to C
6
haloalkyl, C
3
to C
6
alkenyl, C
3
to C
6
haloalkenyl, C
3
to C
6
alkynyl, C
3
to C
6
haloalkynyl, C
1
to C
6
alkoxy C
1
to C
6
alkyl, C
1
to C
6
alkoxy, C
1
to C
6
haloalkoxy, C
1
to C
6
alkoxycarbonyl C
1
to C
6
alkoxy or cyano, and herbicides comprising each of these compounds as an effective component.
Further, the present invention also provides aniline compounds [XXXII] of the formula [XXXII]:
wherein, W represents oxygen, sulfur, imino or C
1
to C
3
alkylimino, R
17
represents oxygen or sulfur, R
4
represents hydrogen or methyl, R
5
represents C
1
to C
6
alkyl, C
1
to C
6
haloalkyl, C
3
to C
6
alkenyl, C
3
to C
6
haloalkenyl, C
3
to C
6
alkynyl, C
3
to C
6
haloalkynyl, X
1
represents halogen, cyano, or nitro, X
2
represents hydrogen or halogen, and each of X
3
and X
4
independently represents hydrogen, halogen, C
1
to C
6
alkyl, C
1
to C
6
haloalkyl, C
3
to C
6
alkenyl, C
3
to C
6
haloalkenyl, C
3
to C
6
alkynyl, C
3
to C
6
haloalkynyl, C
1
to C
6
alkoxy C
1
to C
6
alkyl, C
1
to C
6
alkoxy, C
1
to C
6
haloalkoxy, C
1
to C
6
alkoxycarbonyl C
1
to C
6
alkoxy or cyano,
compounds [XXXIV] of the formula [XXXIV]:
wherein, W represents oxygen, sulfur, imino or C
1
to C
3
alkylimino, R
17
represents oxygen or sulfur, R
4
represents hydrogen or methyl, R
5
represents C
1
to C
6
alkyl, C
1
to C
6
haloalkyl, C
3
to C
6
alkenyl, C
3
to C
6
haloalkenyl, C
3
to C
6
alkynyl, or C
3
to C
6
haloalkynyl, R
18
represents C
1
to C
6
alkyl or phenyl, X
1
represents halogen, cyano, or nitro, X
2
represents hydrogen or halogen, and each of X
3
and X
4
independently represents hydrogen, halogen, C
1
to C
6
alkyl, C
1
to C
6
haloalkyl, C
3
to C
6
alkenyl, C
3
to C
6
haloalkenyl, C
3
to C
6
alkynyl, C
3
to C
6
haloalkinyl, C
1
to C
6
alkoxy C
1
to C
6
alkyl, C
1
to C
6
alkoxy group, C
1
to C
6
haloalkoxy, C
1
to C
6
alkoxycarbonyl C
1
to C
6
alkoxy or cyano group, and
compounds [XXXIII] of the formula [XXXIII]:
wherein, W represents oxygen, sulfur, imino or C
1
to C
3
alkylimino, R
17
represents oxygen or sulfur, R
4
represents hydrogen or methyl, R
5
represents C
1
to C
6
alkyl, C
1
to C
6
haloalkyl, C
3
to C
6
alkenyl, C
3
to C
6
haloalkenyl, C
3
to C
6
alkynyl, or C
3
to C
6
haloalkynyl, X
1
represents halogen, cyano, nitro, X
2
represents hydrogen or halogen, and each of X
3
and X
4
independently represents hydrogen, halogen, C
1
to C
6
alkyl, C
1
to C
6
haloalkyl, C
3
to C
6
alkenyl, C
3
to C
6
haloalkenyl, C
3
to C
6
alkynyl group, C
3
to C
6
haloalkynyl group, C
1
to C
6
alkoxy C
1
to C
6
alkyl, C
1
to C
6
alkoxy, C
1
to C
6
haloalkoxy, C
1
to C
6
alkoxycarbonyl C
1
to C
6
alkoxy or cyano,
which are useful as intermediates for producing the present compounds.
In the present invention, the C
1
to C
3
alkylimino represented by W includes methylimino, ethylimino and the like,
the C
1
to C
3
alkylimino represented by Y includes methylimino, ethylimino and the like,
the C
1
to C
3
alkyl represented by R
1
means methyl, ethyl, propyl, isopropyl, the C
1
to C
3
haloalkyl represented by R
1
includes bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 3,3,3-trifluoropropyl and the like,
the C
1
to C
3
alkyl represented by R
2
means methyl, ethyl, propyl, isopropyl,
the C
1
to C
6
alkyl represented by R
5
includes methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl and the like, the C
1
to C
6
haloalkyl represented by R
5
includes bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluoromethyl, pentafluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2,2-trichloroethyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl and the like, the C
3
to C
6
alkenyl represented by R
5
includes allyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-butenyl, 2-butenyl, 3-butenyl and the like, the C
3
to C
6
haloalkenyl represented by R
5
includes 1-chloroallyl, 1-bromoallyl, 2-chloroallyl, 3,3-dichloroallyl and the like, the C
3
to C
6
alkynyl represented by R
5
includes 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-butynyl and the like, the C
3
to C
6
haloalkynyl represented by R
5
includes 3-chloro-2-propynyl, 3-bromo-2-propynyl, 1-fluoro-2-propynyl, 1-chloro-2-propynyl, 1-bromo-2-propynyl, 1-chloro-2-butynyl and the like,
the C
1
to C
6
alkyl represented by R
18
includes methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl and the like,
the halogen represented by X
1
means fluorine, chlorine, bromine, iodine,
the halogen represented by X
2
means fluorine, chlorine, bromine, iodine,
the halogen represented by X
3
and X
4
means fluorine, chlorine, bromine, iodine,
the C
1
to C
6
alkyl represented by X
3
and X
4
includes methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl and the like, the C
1
to C
6
haloalkyl represented by X
3
and X
4
includes bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluoromethyl, pentafluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2,2-trichloroethyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl and the like, the C
3
to C
6
alkenyl represented by X
3
and X
4
includes allyl, 1-methylallyl, 1, 1-dimethylallyl, 2-methylallyl, 1-butenyl, 2-butenyl, 3-butenyl and the like, the C
3
to C
6
haloalkenyl represented by X
3
and X
4
includes 1-chloroallyl, 1-bromoallyl, 2-chloroallyl, 3,3-dichloroallyl and the like, the C
3
to C
6
alkynyl represented by X
3
and X
4
includes 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-butynyl and the like, the C
3
to C
6
haloalkynyl represented by X
3
and X
4
includes 3-chloro-2-propynyl, 3-bromo-2-propynyl, 1-fluoro-2-propynyl, 1-chloro-2-propynyl, 1-bromo-2-propynyl, 1-chloro-2-butynyl and the like, the C
1
to C
6
alko

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