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US 4,358,307 AGranted
Herbicidal quinoxaline carboxylic acid derivatives
AssigneeICI Australia Limited
InventorsAlexander Serban, Keith G. Watson, Graeme J. Farquharson
Life of this patent
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Abstract
The invention concerns novel compounds of the formula I ##STR1## The compounds are herbicides and in further embodiments the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of compounds of formula I, herbicidal composition containing as active ingredient a compound of formula I, and processes for severely damaging or killing unwanted plants by applying to the plants or to the growth medium of the plants an effective amount of a compound of formula I.
Claims13
A compound of formula I ##STR21## or acid addition salt thereof wherein;
- A, B, D, E, J, U and V are independently chosen from the group consisting of hydrogen, halogen, nitro, cyano, thiocyano, amino, C.sub.1 to C.sub.6 alkylamino, di(C.sub.1 to C.sub.6 alkyl)amino, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl, C.sub.2 to C.sub.6 alkenyl, C.sub.3 to C.sub.7 cycloalkyl, C.sub.1 to C.sub.6 alkoxy, C.sub.1 to C.sub.6 haloalkoxy, C.sub.1 to C.sub.6 alkylthio, C.sub.1 to C.sub.6 alkylsulfinyl, C.sub.1 to C.sub.6 alkylsulfonyl, C.sub.1 to C.sub.6 haloalkylsulfinyl, C.sub.1 to C.sub.6 haloalkylsulfonyl, sulfo, C.sub.1 to C.sub.6 alkoxysulfonyl, sulfamoyl, N-(C.sub.1 to C.sub.6 alkyl) sulfamoyl, N,N-di(C.sub.1 to C.sub.6 alkyl)sulfamoyl, carboxy, (C.sub.1 to C.sub.6 alkoxy)carbonyl, carbamoyl, N-(C.sub.1 to C.sub.6 alkyl)carbamoyl, N,N-di(C.sub.1 to C.sub.6 alkyl)carbamoyl, phenyl, phenoxy, phenylthio, and the groups substituted phenyl, substituted phenoxy and substituted phenylthio wherein in each group the phenyl ring is substituted with from one to three substituents chosen from the group consisting of halogen, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl, C.sub.1 to C.sub.6 alkoxy, nitro and cyano;
- R.sup.1 is chosen from the group consisting of hydrogen, C.sub.1 to C.sub.10 alkyl, C.sub.2 to C.sub.10 alkenyl, C.sub.2 to C.sub.10 alkynyl, C.sub.2 to C.sub.10 alkoxyalkyl, cyanomethyl, (C.sub.1 to C.sub.6 alkoxy)-carbonylmethyl, C.sub.1 to C.sub.10 haloalkyl, formyl, C.sub.2 to C.sub.10 alkanoyl, phenyl, benzyl, benzoyl, and the groups phenyl, benzyl and benzoyl wherein in each group the phenyl ring is substituted with from one to three substituents chosen from the group consisting of halogen, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl, C.sub.1 to C.sub.6 alkoxy, nitro and cyano;
- R.sup.2 is chosen from the group consisting of hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub.2 to C.sub.6 alkenyl, C.sub.2 to C.sub.6 alkoxyalkyl, C.sub.1 to C.sub.6 haloalkyl, acetyl, propionyl, and C.sub.2 to C.sub.6 alkoxycarbonyl;
- R.sup.3 is chosen from the group consisting of hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub.2 to C.sub.6 alkenyl, C.sub.2 to C.sub.6 alkoxyalkyl and C.sub.1 to C.sub.6 haloalkyl, or R.sup.2 and R.sup.3 together may form a methylene, ethylidene, propylidene or isopropylidene group;
- W is chosen from the group consisting of cyano, thiocarbamoyl, ##STR22## and CH.sub.2 Z wherein:
- G is chosen from the group consisting of hydroxy, mercapto, C.sub.1 to C.sub.10 alkoxy, C.sub.1 to C.sub.10 haloalkoxy, C.sub.2 to C.sub.10 alkenyloxy, C.sub.2 to C.sub.10 alkynyloxy, C.sub.1 to C.sub.10 alkylthio, C.sub.2 to C.sub.10 alkenylthio, C.sub.2 to C.sub.10 alkynylthio, C.sub.3 to C.sub.7 cycloalkoxy, C.sub.3 to C.sub.7 cycloalkoxy substituted with one or two C.sub.1 to C.sub.4 alkyl groups, phenoxy, phenylthio, benzyloxy, benzylthio, the group C.sub.1 to C.sub.6 alkoxy substituted with a substituent chosen from the group consisting of C.sub.1 to C.sub.6 alkoxy, amino, cyano, N-(C.sub.1 to C.sub.6 alkyl)amino and N,N-di(C.sub.1 to C.sub.6 alkyl)amino, the groups phenoxy, phenylthio, benzyloxy and benzylthio wherein in each group the phenyl ring is substituted with from one to three substituents chosen from the group consisting of halogen, nitro, cyano, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl and C.sub.1 to C.sub.6 alkoxy, the group OM wherein M is an alkali metal ion, alkaline earth metal ion or an ammonium ion N.sup..sym. R.sup.7 R.sup.8 R.sup.9 wherein R.sup.7, R.sup.8 and R.sup.9 are independently chosen from the group consisting of hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 hydroxyalkyl, phenyl and benzyl, the group --NHSO.sub.2 R.sup.4 wherein R.sup.4 is chosen from C.sub.1 to C.sub.10 alkyl and C.sub.1 to C.sub.10 haloalkyl, and the group --NR.sup.5 R.sup.6 wherein R.sup.5 and R.sup.6 are independently chosen from the group consisting of hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 hydroxyalkyl, C.sub.1 to C.sub.6 haloalkyl, phenyl, and benzyl, and the group --O--N.dbd.R.sup.10 wherein R.sup.10 is a C.sub.1 to C.sub.10 alkylidene group;
- and Z is chosen from halogen, hydroxy, mercapto, C.sub.1 to C.sub.10 alkoxy, C.sub.1 to C.sub.10 haloalkoxy, C.sub.1 to C.sub.10 alkylthio and the group NR.sup.5 R.sup.6 wherein R.sup.5 and R.sup.6 are hereinbefore defined;
- X is chosen from oxygen and sulfur;
- k is chosen from 0 to 1;
- 1 is 0;
- and n is 0, 1 or 2.
8 more elements
Dependencies are inferred from the claim text.