Uracil compounds and use thereof

Details Uracil compounds and use thereof Uracil compounds and use thereof

2002-01-07

2003-12-16

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S312000, C544S314000

Reexamination Certificate

active

06664214

ABSTRACT:

TECHNICAL FIELD
The present invention relates to uracil compounds and use thereof.
DISCLOSURE OF INVENTION
The subject of the invention is to provide compounds having an excellent herbicidal activity.
As the result of extensive studies conducted for finding out compounds having an excellent herbicidal activity, the inventors of the invention have found the fact that uracil compounds represented by Chemical Formula 2, shown below, have an excellent herbicidal activity and have completed the invention. Therefore, the invention provides an uracil compound (hereinafter, referred to as the compound(s) of the invention) represented by Chemical Formula 2:
wherein W represents oxygen or sulfur; 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 or C
1
- to C
3
-haloalkyl; R
3
represents hydrogen, C
1
- to C
3
-alkyl, phenyl, C
1
- to C
3
-haloalkyl or cyano; R
4
represents hydrogen or C
1
- to C
3
-alkyl; 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; X
2
represents hydrogen or halogen; X
3
and X
4
are independent with each other and each represents hydrogen, halogen, C
1
- to C
6
-alkyl, C
1
- to C
6
-haloalkyl, C
2
- to C
6
-alkenyl, C
2
- 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 or cyano; and n represents an integer of 1 to 4; and a herbicide comprising the same as an active ingredient.
BEST MODE FOR CARRYING OUT THE INVENTION
In the invention, C
1
- to C
3
-alkyl represented by R
1
means methyl, ethyl, propyl or isopropyl; 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;
C
1
- to C
3
-alkyl represented by R
2
means methyl, ethyl, propyl or isopropyl; C
1
- to C
3
-haloalkyl represented by R
2
includes bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 3,3,3-trifluoropropyl and the like;
C
1
- to C
3
-alkyl represented by R
3
means methyl, ethyl, propyl or isopropyl; C
1
- to C
3
-haloalkyl represented by R
3
includes bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 3,3,3-trifluoropropyl and the like;
C
1
- to C
3
-alkyl represented by R
4
means methyl, ethyl, propyl or isopropyl; C
1
- to C
6
-alkyl represented by R
5
includes methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl and the like; C
1
- to C
6
-haloalkyl represented by R
5
includes bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, pentafluoroethyl, 2-fluoroethyl, 2,2,2-trichloroethyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl and the like; 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; C
3
- to C
6
-haloalkenyl represented by R
5
includes 1-chloroallyl, 1-bromoallyl, 2-chloroallyl, 3,3-dichloroallyl and the like; 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; 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;
halogen represented by X
1
and X
2
means fluorine, chlorine, bromine and iodine; halogen represented by X
3
and X
4
means fluorine, chlorine, bromine and iodine; 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; 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; C
2
- to C
6
-alkenyl represented by X
3
and X4 includes vinyl, allyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-butenyl, 2-butenyl, 3-butenyl and the like; C
2
- to C
6
-haloalkenyl represented by X
3
and X
4
includes difluorovinyl dichlorovinyl, 1-chloroallyl, 1-bromoallyl, 2-chloroallyl, 3,3-dichloroallyl and the like; 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; 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; C
1
- to C
6
-alkoxy-C
1
- to C
6
-alkyl represented by X
3
and X
4
includes methoxymethyl, 2-methoxyethyl, 1-methoxyethyl, 3-methoxypropyl, ethoxymethyl, 2-ethoxyethyl, 3-ethoxypropyl, isopropoxymethyl, 2-isopropoxyethyl and the like; C
1
- to C
6
-alkoxy represented by X
3
and X
4
includes methoxy, ethoxy, propoxy, isopropoxy, butyloxy, s-butyloxy, t-butyloxy and the like; and C
1
- to C
6
-haloalkoxy represented by X
3
and X
4
includes chloromethoxy, bromomethoxy, dichloromethyloxy, trichloromethyloxy, trifluoromethyloxy, 2-fluoroethyloxy, 2,2,2-trichloroethyloxy and the like.
From the viewpoint of herbicidal activity, preferred compounds among the compounds of the invention are compounds wherein R
1
is methyl substituted with one or more fluorine (for example, trifluoromethyl, chlorodifluoromethyl, difluoromethyl or the like) or ethyl substituted with one or more fluorine (for example, pentafluoroethyl, 1,1-difluoroethyl or the like), compounds wherein R
2
is methyl, compounds wherein X
1
is chlorine, compounds wherein X
2
is fluorine, or compounds wherein the connecting position of W is 3- or 4-position on the benzene ring. A more preferred compound is methyl 2-[4-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenoxy}methyl)phenoxy]propionate.
While sometimes geometrical isomers originated from a double bond, optical isomers and diastereoisomers originated from (an) asymmetric carbon(s) may exist in the compounds of the invention, the compounds of the invention extends to all of these isomers and mixtures thereof.
Processes for producing the compound of the invention are described below.
The compound of the invention can be produced according to processes including (Production Process 1) to (Production Process 6) described below:
Production Process 1
The compound of the invention can be produced by reacting an uracil compound represented by Chemical Formula 3:
wherein R
1
, R
2
, X
1
and X
2
have the same meaning as above, with a compound represented by Chemical Formula 4:
wherein R
3
, R
4
, R
5
, W, X
3
, X
4
and n have the same meaning as above and R
6
represents a leaving group such as chlorine, bromine, iodine, methanesulfonyloxy, p-toluenesulfonyloxy and the like, in the presence of a base.
Said reaction is usually carried out without solvent or in a solvent; the range of the reaction temperature is 0 to 200° C. and the range of the reaction period is usually a moment to 24 hours.
The amount of the reagents used for the reaction can optionally be varied according to circumstances, while the theoretical amount of the compound represented by Chemical Formula 4 is 1 mole and the amount of the base is 1 mole, based on 1 mole of the uracil compound represented by Chemical Formula 3.
Usable base includes organic bases such as pyridine, quinoline, benzyldimethylamine, phenethyldimethylamine, N-methylmorpholine, 1,8-diaza

Affiliated with

Also associated with

Rating

Uracil compounds and use thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Uracil compounds and use thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Uracil compounds and use thereof will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3181728