Uracil compounds and use thereof

Details Uracil compounds and use thereof Uracil compounds and use thereof

2001-01-31

2003-03-25

Shah, Mukund J. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S295000, C544S296000, C544S312000, C544S314000, C546S243000, C548S134000, C548S135000, C548S356100, C548S366100

Reexamination Certificate

active

06537948

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.
Currently, a lot of herbicides are commercially available and used, however since there are many kinds of weeds to be controlled and generation thereof ranges over a long period, there is requirement a herbicide which have higher herbicidal effect, have a wide range of herbicidal spectrum, and causes no phytotoxicity on crops.
U.S. Pat. No. 4,859,229, WO92/11244, WO97/01541, WO97/05116, WO98/41093 and the like disclose that certain kinds of phenyluracil compounds have herbicidal activity, however, these phenyluracil compounds do not have sufficient abilities as a herbicide.
The present inventors have intensively studied to find a compound 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 of the formula [I] (hereinafter, referred to as the present compound):
[wherein, Q-R
3
represents a R
3
-substituted group of a 5-membered or 6-membered heterocyclic ring having one or two nitrogen selected from the group consisting of moieties represented by the following formulae
(wherein, this heterocyclic ring may be substituted with at least one kind of substituent selected from the group consisting of halogen, C1 to C6 alkyl, C1 to C6 haloalkyl, C2 to C6 alkenyl, C2 to C6 haloalkenyl, C2 to C6 alkynyl, C2 to C6 haloalkynyl, C1 to C6 alkoxy C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 haloalkoxy, C1 to C6 alkoxycarbonyl C1 to C6 alkoxy, C1 to C6 alkoxycarbonyl C1 to C6 alkyl, cyano, hydroxy, mercapto, oxo and thioxo.), Y represents oxygen, sulfur, imino or C1 to C3 alkylimino, R
1
represents C1 to C3 alkyl or C1 to C3 haloalkyl, R
2
represents C1 to C3 alkyl, R
3
represents carboxy C1 to C6 alkyl, C1 to C6 alkoxycarbonyl C1 to C6 alkyl, C1 to C6 haloalkoxycarbonyl C1 to C6 alkyl, C3 to C6 alkenyloxycarbonyl C1 to C6 alkyl, C3 to C6 haloalkenyloxycarbonyl C1 to C6 alkyl, C3 to C6 alkynyloxycarbonyl C1 to C6 alkyl, C3 to C6 haloalkynyloxycarbonyl C1 to C6 alkyl, OR
7
, SR
8
or N(R
9
)R
10
, X
1
represents halogen, cyano, thiocarbamoyl or nitro, X
2
represents hydrogen or halogen.
{wherein, each of R
7
, R
8
and R
10
independently represents carboxy C1 to C6 alkyl, C1 to C6 alkoxycarbonyl C1 to C6 alkyl, C1 to C6 haloalkoxycarbonyl C1 to C6 alkyl, C3 to C6 alkenyloxycarbonyl C1 to C6 alkyl, C3 to C6 haloalkenyloxycarbonyl C1 to C6 alkyl, C3 to C6 alkynyloxycarbonyl C1 to C6 alkyl, C3 to C6 haloalkynyloxycarbonyl C1 to C6 alkyl, C3 to C8 cycloalkoxycarbonyl C1 to C6 alkyl, C3 to C8 halocycloalkoxycarbonyl C1 to C6 alkyl, C3 to C8 cycloalkenyloxycarbonyl C1 to C6 alkyl, C3 to C8 halocycloalkenyloxycarbonyl C1 to C6 alkyl, C1 to C6 alkoxycarbonyl C1 to C6 alkoxycarbonyl C1 to C6 alkyl, C1 to C8 alkylidenaminoxycarbonyl C1 to C6 alkyl, phenoxycarbonyl C1 to C6 alkyl which may be substituted, phenyl C1 to C4 alkoxycarbonyl C1 to C6 alkyl which may be substituted, C1 to C6 alkoxyaminocarbonyl C1 to C6 alkyl, (C1 to C6 alkoxy)(C1 to C3 alkyl)aminocarbonyl C1 to C6 alkyl, C1 to C6 alkylaminocarbonyl C1 to C6 alkyl, (C1 to C6 alkyl) C1 to C6 alkylaminocarbonyl C1 to C6 alkyl, phenylaminocarbonyl C1 to C6 alkyl which may be substituted, or phenyl C1 to C4 alkylaminocarbonyl C1 to C6 alkyl which may be substituted, and R
9
represents hydrogen or C1 to C6 alkyl.}.], and herbicides containing each of them as an effective ingredient.
In the present invention, as the group represented by Q-R
3
, for example, there are listed groups of the following formulae:
[wherein, R
3
is the same as defined above, each of Z
1
and Z
2
independently represents hydrogen, halogen, C1 to C6 alkyl, C1 to C6 haloalkyl, C2 to C6 alkenyl, C2 to C6 haloalkenyl, C2 to C6 alkynyl, C2 to C6 haloalkynyl, C1 to C6 alkoxy C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 haloalkoxy, C1 to C6 alkoxycarbonyl C1 to C6 alkoxy or cyano (wherein, the halogen represented by Z
1
or Z
2
means fluorine, chlorine, bromine or iodine, and examples of the C1 to C6 alkyl include methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl and the like, examples of the C1 to C6 haloalkyl include 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, examples of the C2 to C6 alkenyl include allyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-butenyl, 2-butenyl, 3-butenyl and the like, examples of the C2 to C6 haloalkenyl include 1-chloroallyl, 1-bromoallyl, 2-chloroallyl, 3,3-dichloroallyl and the like, examples of the C2 to C6 alkynyl include 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-butynyl and the like, examples of the C2 to C6 haloalkynyl include 3-bromo-2-propynyl, 3-iodo-2-propynyl, 1-fluoro-2-propynyl, 1-chloro-2-propynyl, 1-bromo-2-propynyl, 1-chloro-2-butynyl and the like, examples of the C1 to C6 alkoxy C1 to C6 alkyl include methoxymethyl, 2-methoxyethyl, 1-methoxyethyl, 3-methoxypropyl, ethoxymethyl, 2-ethoxyethyl, 3-ethoxypropyl, isopropoxymethyl, 2-isopropoxyethyl and the like, examples of the C1 to C6 alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butyloxy, s-butyloxy, t-butyloxy and the like, examples of the C1 to C6 haloalkoxy include chloromethoxy, bromomethoxy, dichloromethyloxy, trichloromethyloxy, trifluoromethyloxy, 2-fluoroethyloxy, 2,2,2-trichloroethyloxy and the like, examples of the C1 to C6 alkoxycarbonyl C1 to C6 alkoxy include methoxycarbonylmethoxy, ethoxycarbonylmethoxy, propoxycarbonylmethoxy, isopropoxycarbonylmethoxy, 1-methoxycarbonylethoxy, 1-ethoxycarbonylethoxy, 1-propoxycarbonylethoxy, 1-isopropoxycarbonylethoxy, 2-methoxycarbonylethoxy, 2-ethoxycarbonylethoxy, 2-propoxycarbonylethoxy, 2-isopropoxycarbonylethoxy and the like, examples of the C1 to C6 alkoxycarbonyl C1 to C6 alkyl include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-t-butoxycarbonylethyl and the like.).].
Examples of the carboxy C1 to C6 alkyl represented by R
3
include carboxymethyl, 1-carboxyethyl, 2-carboxyethyl and the like, examples of the C1 to C6 alkoxycarbonyl C1 to C6 alkyl include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl and the like, examples of the C1 to C6 haloalkoxycarbonyl C1 to C6 alkyl include chloromethyloxycarbonylmethyl, 2-fluoroethyloxycarbonylmethyl, 2-chloropropyloxycarbonylmethyl, 1-chloro-2-propyloxycarbonylmethyl, 2,2,2-trifluoroethyloxycarbonylmethyl and the like, examples of the C3 to C6 alkenyloxycarbonyl C1 to C6 alkyl include allyloxycarbonylmethyl, 1-methyl-2-propenyloxycarbonylmethyl, 2-methyl-2-propenyloxycarbonylmethyl, 2-butenyloxycarbonylmethyl, 1-allyloxycarbonylethyl, 1-(1-methyl-2-propenyloxycarbonyl)ethyl, 1-(2-methyl-2-propenyloxycarbonyl)ethyl, 2-allyloxycarbonylethyl, 2-(2-methyl-2-propenyloxycarbonyl)ethyl and the like, examples of the C3 to C6 haloalkenyloxycarbonyl C1 to C6 alkyl include 1-chloroallyloxycarbonylmethyl, 1-(1-chloroallyloxycarbonyl)ethyl, 2-chloroallyloxycarbonylmethyl, 1-(2-chloroallyloxycarbonyl)ethyl and the like, examples of the C3 to C6 alkynyloxycarbonyl C1 to C6

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