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 Herbicidal heterocyclic compounds

Details
Inventors: Wenger, Jean; Winternitz, Paul;
Assignee: Hoffmann-La Roche Inc. (Nutley, NJ)
Primary Examiner: Rizzo; Nicholas S.
Assistant Examiner: Shen; Cecilia
Attorney, Agent or Firm: Saxe; Jon S., Gould; George M., Tramaloni; Dennis P.

The invention is concerned with novel C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl and C.sub.3 or 4 -alkynyl enol ethers of 3-aryluracils of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and X are as defined in the specification, their manufacture, weed control compositions which contain such enol ethers as the active substance and the use of the active substances or compositions for the control of weeds. The invention is also concerned with certain novel intermediates, some of which possess herbicidal activity, and with weed control compositions containing such active substances.

DETAILED DESCRIPTION OF THE INVENTION The present invention is concerned with heterocyclic compounds.
namely C.
sub.
1-4 -alkyl.
C.
sub.
2-4 -alkenyl and C.
sub.
3 or .
sub.
4 -alkynyl enol ethers of 3-aryluracils of the general formula ##STR2## wherein R.
sup.
1 signifies C.
sub.
1-8 -alkyl, C.
sub.
2-6 -alkenyl, C.
sub.
2-6 -alkynyl, C.
sub.
2-8 -alkoxyalkyl or a group R.
sup.
2 signifies halogen or cyano, R.
sup.
3 signifies hydrogen or halogen.
R.
sup.
4 signifies hydrogen, fluorine or C.
sub.
1-4 -alkyl.
R.
sup.
5 signifies C.
sub.
1-4 -alkyl or C.
sub.
1-4 -haloalkyl.
R.
sup.
4 and R.
sup.
5 together signify tri- or tetramethylene, R.
sup.
6 and R.
sup.
7 each independently signify C.
sub.
1-4 -alkyl.
m signifies 1 or 2 and X signifies O, O-C(O).
O-C(O)-O or C(O)-O.
The enol ethers in accordance with the invention thus embrace the compounds of the formulae ##STR3## wherein R.
sup.
1 -R.
sup.
5 and X have the significances given above and R signifies C.
sub.
1-4 -alkyl.
C.
sub.
2-4 -alkenyl or C.
sub.
3 or 4 -alkynyl.
The enol ethers in accordance with the invention have herbicidal activity and are suitable as active substances of weed control compositions.
Accordingly, the invention also embraces weed control compositions which contain enol ethers in accordance with the invention as active substances.
a process for the manufacture of these compounds as well as the use of such enol ethers or compositions for the control of weeds.
In the above definitions of the residues R.
sup.
2, R.
sup.
3 and R.
sup.
5 "halogen" per se or "halo" as part of the haloalkyl group embraces fluorine, chlorine, bromine and iodine.
The haloalkyl group (R.
sup.
5) can have one or more similar or different halogen atoms, trifluoromethyl being an example of a multiply halogenated alkyl residue.
The alkyl, alkenyl and alkynyl residues (R, R.
sup.
1, R.
sup.
4, R.
sup.
5, R.
sup.
6, R.
sup.
7) can be straight-chain or branched, and this also applies to the or each alkyl part of the alkoxyalkyl and haloalkyl groups (R.
sup.
1, R.
sup.
5).
A sub-group of enol ethers in accordance with the invention comprises the C



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