3-(5-carboxy-4-substituted-phenyl)-(thio)uracil-esters and salts
AssigneeHoffmann-La Roche Inc.
InventorsJean Wenger, Paul Winternitz
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Abstract
The disclosure is concerned with novel 3-aryluracils of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the significances given in the description, as well as salts thereof and their manufacture, weed control compositions which contain such compounds as active ingredients and the use of the active ingredients or compositions for the control of weeds. The disclosure also concerns certain herbicidally active starting materials and weed control compositions containing these as active ingredients.
Claims21
Compounds of the formula ##STR21## wherein R.sup.1 signifies hydrogen, C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl, C.sub.2-6 -alkoxyalkyl, formyl, C.sub.2-6 -alkanoyl or C.sub.2-6 -alkoxycarbonyl,
- R.sup.2 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl or C.sub.2-6 -alkoxyalkyl,
- R.sup.3 signifies halogen or nitro,
- R.sup.4 signifies hydrogen or halogen,
- R.sup.5 signifies hydrogen, halogen, C.sub.1-4 -alkyl, chloromethyl, bromomethyl, hydroxymethyl, (C.sub.1-5 -alkoxy)methyl, (C.sub.1-5 -alkylthio)methyl, cyano, nitro or thiocyanato,
- R.sup.6 signifies hydrogen, C.sub.1-4 -alkyl or C.sub.1-4 -fluoroalkyl, or
- R.sup.5 and R.sup.6 together signify tri- or tetramethylene in which one methylene can be replaced by oxygen or sulphur and which is optionally substituted with C.sub.1-3 -alkyl, and
- X signifies oxygen or sulphur, with the provisos that (i) R.sup.6 is C.sub.1-4 -alkyl or C.sub.1-4 -fluoroalkyl when R.sup.5 is fluorine and (ii) R.sup.6 is hydrogen or C.sub.1-4 -alkyl and X is oxygen when R.sup.5 is cyano,
- as well as the alkali metal, alkaline earth metal, ammonium and organic base salts of those compounds of formula I in which R.sup.1 and/or R.sup.2 signifies hydrogen.
Compounds of the formula ##STR22## wherein R.sup.1 ' signifies C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl, C.sub.2-6 -alkoxyalkyl, formyl, C.sub.2-6 -alkanoyl or C.sub.2-6 -alkoxycarbohyl,
- R.sup.2 ' signifies C.sub.1-6 -alkyl, C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl or C.sub.2-6 -alkoxyalkyl,
- R.sup.3 signifies halogen or nitro,
- R.sup.4 signifies hydrogen or halogen,
- R.sup.5 signifies hydrogen, halogen, C.sub.1-4 -alkyl, chloromethyl, bromomethyl, hydroxymethyl, (C.sub.1-5 -alkoxy)methyl, (C.sub.1-5 -alkylthio)methyl, cyano, nitro or thiocyanato,
- R.sup.6 signifies hydrogen, C.sub.1-4 -alkyl or C.sub.1-4 -fluoroalkyl, or
- R.sup.5 and R.sup.6 together signify tri- or tetramethylene in which one methylene can be replaced by oxygen or sulphur and which is optionally substituted with C.sub.1-2 -alkyl, and
- X signifies oxygen or sulphur, with the provisos that (i) R.sup.6 is C.sub.1-4 -alkyl or C.sub.1-4 -fluoroalkyl when R.sup.5 is fluorine and (ii) R.sup.6 is hydrogen or C.sub.1-4 -alkyl and X is oxygen when R.sup.5 is cyano.
A weed control composition, characterized in that it contains an effective amount of at least one compound of the formula ##STR23## wherein R.sup.1' signifies hydrogen, C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl, C.sub.2-6 -alkoxyalkyl, formyl, C.sub.2-6 -alkanoyl or C.sub.2-6 -alkoxycarbonyl,
- R.sup.2' signifies hydrogen, C.sub.1-6 -alkyl, C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl or C.sub.2-6 -alkoxyalkyl,
- R.sup.3 signifies halogen or nitro,
- R.sup.4 signifies hydrogen or halogen,
- R.sup.5 signifies hydrogen, halogen, C.sub.1-4 alkyl, chloromethyl, bromomethyl, hydroxymethyl, (C.sub.1-5 alkoxy)methyl, (C.sub.1-5 -alkylthio)methyl, cyano, nitro or thiocyanato,
- R.sup.6 signifies hydrogen, C.sub.1-4 -alkyl or C.sub.1-4 -fluoroalkyl, or
- R.sup.5 and R.sup.6 together signify tri- or tetramethylene in whcih one methylene can be replaced by oxygen or sulphur and which is optionally substituted with C.sub.1-3 -alkyl, and
- X signifies oxygen or sulphur, with the provisos that (i) R.sup.6 is C.sub.1-4 -alkyl or C.sub.1-4 -fluoroalkyl when R.sup.5 is fluorine and (ii) R.sup.6 is hydrogen or C.sub.1-4 -alkyl and X is oxygen when R.sup.5 is cyano
- as well as formulation adjuvants.
Dependencies are inferred from the claim text.