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US 5,516,751 AGranted
Herbicidal 2-(2-imidazolin-2-yl)-benzazoles
AssigneeAmerican Cyanamid Company
InventorRobert F. Doehner, Jr.
Life of this patent
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Abstract
There are provided o-carboxy-(5-oxo-2-imidazolin-2-yl)benzoheterocyclic compounds wherein the fused heterocyclic ring system is a 5-membered ring containing one, two or three nitrogen atoms, derivatives of said benzoheterocyclic compounds and a method for the use therewith to control monocotyledenous and dicotyledenous plant species.
Claims11
A compound having the structure ##STR79## wherein R.sub.1 is hydrogen, di(C.sub.1 -C.sub.4)alkylimino;
- C.sub.1 -C.sub.12 alkyl optionally substituted with one or more of the following:
- C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, halogen, hydroxy, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, nitrophenyl, carboxy, C.sub.1 -C.sub.4 alkoxycarbonyl, cyano or tri(C.sub.1 -C.sub.4)alkylammonium halide;
- C.sub.3 -C.sub.12 alkenyl optionally substituted with one or more of the following groups:
- C.sub.1 -C.sub.4 alkoxy, phenyl, halogen or C.sub.1 -C.sub.4 alkoxycarbonyl,
- C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one or more C.sub.1 -C.sub.4 alkyl groups,
- C.sub.3 -C.sub.16 alkynyl optionally substituted with one or more C.sub.1 -C.sub.4 alkyl groups;
- or a cation;
- R.sub.2 is C.sub.1 -C.sub.4 alkyl;
- R.sub.3 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl;
- and when R.sub.2 and R.sub.3 are taken together with the carbon to which they are attached they may represent C.sub.3 -C.sub.6 cycloalkyl optionally substituted with methyl;
- B is hydrogen, COR.sub.4 or SO.sub.2 R.sub.5 with the proviso that when B is COR.sub.4 or SO.sub.2 R.sub.5, R.sub.1 is other than hydrogen or a cation and R.sub.9 is other than hydrogen;
- R.sub.4 is C.sub.1 -C.sub.11 alkyl, chloromethyl or phenyl optionally substituted with halogen, nitro or C.sub.1 -C.sub.4 alkyl;
- R.sub.5 is C.sub.1 -C.sub.4 alkyl or phenyl optionally substituted with C.sub.1 -C.sub.4 alkyl;
- X, Y and Z are each independently, N, or NR.sub.9 ;
- the ---------- configuration represents either a single bond or a double bond with the proviso that when any of X, Y or Z is NR.sub.9, then the ---------- configuration represents a single bond and with the further proviso that at least one of the ---------- configurations represents a single bond;
- R.sub.9 is hydrogen or C.sub.1 -C.sub.4 alkyl optionally substituted with one hydroxy or one to three halogens, C.sub.1 -C.sub.4 alkoxy groups or C.sub.1 -C.sub.4 alkylthio groups;
- Q is hydrogen, halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkyl optionally substituted with one to three of the following:
- halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, or C.sub.2 -C.sub.4 alkenyl;
- the optical isomers thereof when R.sub.2 and R.sub.3 are not the same;
- the tautomers and geometric isomers thereof and the agriculturally acceptable acid addition salts thereof except when R.sub.1 is a salt-forming cation.
17 more elements
Dependencies are inferred from the claim text.