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 3-aryldihydrouracils

Details
Inventors: Brouwer, Walter G.; Felauer, Ethel Ellen; Bell, Allyn Roy;
Assignee: Uniroyal Chemical Company, Inc. (Middlebury, CT); Uniroyal Chemical Ltd/Ltee (Don Mills, CA)
Primary Examiner: Shen; Cecilia
Assistant Examiner:
Attorney, Agent or Firm: Karta; Glenn E.

A compound having the structural formula ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.4 alkenyl or trifluoromethyl; R.sup.2 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 --C.sub.4 alkenyl, C.sub.7 -C.sub.10 aralkyl or C.sub.7 -C.sub.10 haloaralkyl; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.2 alkyl; X is halogen; Y is hydrogen, C.sub.1 -C.sub.4 alkyl or halogen; and Z is oxygen or sulfur is disclosed. In addition, a process for forming the compound is set forth. A method for controlling weeds which comprises applying a herbicidally effective amount of the compound recited above is also described. Finally, a composition, useful as a herbicide, including the compound of this invention and a suitable carrier therefor is taught.

DETAILED DESCRIPTION The present invention is directed to a class of compounds having the structural formula ##STR4## where R.
sup.
1 is hydrogen, C.
sub.
1 -C.
sub.
4 alkyl, C.
sub.
3 -C.
sub.
6 cycloalkyl, C.
sub.
3 -C.
sub.
4 alkenyl or trifluoromethyl; R.
sup.
2 is C.
sub.
1 -C.
sub.
4 alkyl, C.
sub.
3 -C.
sub.
6 cycloalkyl, C.
sub.
3 -C.
sub.
4 alkenyl, C.
sub.
7 -C.
sub.
10 aralkyl or C.
sub.
7 -C.
sub.
10 haloaralkyl; R.
sup.
3 is hydrogen or C.
sub.
1 -C.
sub.
4 alkyl; R.
sup.
4 is hydrogen or C.
sub.
1 -C.
sub.
2 alkyl; X is halogen; Y is hydrogen, C.
sub.
1 -C.
sub.
4 alkyl or halogen; and Z is oxygen or sulfur.
Preferably, the compound of the present invention has the structural formula I where R.
sup.
1 is hydrogen, C.
sub.
1 -C.
sub.
2 alkyl or trifluoromethyl; R.
sup.
2 is C.
sub.
1 -C.
sub.
3 alkyl, cyclohexyl, propenyl, C.
sub.
7 -C.
sub.
9 aralkyl or C.
sub.
7 -C.
sub.
9 haloaralkyl; R.
sup.
3 is hydrogen or C.
sub.
1 -C.
sub.
3 alkyl; R.
sup.
4 is hydrogen or methyl; X is fluorine; Y is hydrogen, C.
sub.
1 -C.
sub.
2 alkyl or chlorine; and Z is oxygen.
More preferably, the compound of the present invention has the structural formula I where R.
sup.
1 is hydrogen, methyl or trifluoromethyl; R.
sup.
2 is methyl, isopropyl, cyclohexyl, propenyl or chlorobenzyl; R.
sup.
3 is hydrogen or isopropyl; R.
sup.
4 is hydrogen; and Y is methyl or chlorine.
The meanings of X and Z are those given in the preferred embodiment of the compound of the present invention.
The compound of the present invention, the compound having the structural formula I, where R.
sup.
1, R.
sup.
2, R.
sup.
3, R.
sup.
4, X, Y and Z have the meanings given for the broadest definition of the compound, is prepared in a series of steps which begins with the reaction of a primary amine of the formula R.
sup.
2 NH.
sub.
2 (II) where R.
sup.
2 has the same meanings as those given for the compound having the structural formula I and an unsaturated ester of the formula R.
sup.
1 CH.
dbd.
CHCOOR.
sup.
5 (III) where R.
sup.
1 has the meanings as those given for the compound having the structural formula I; and R.
sup.
5 is C.
sub



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