US 4,643,763 A · Herbicidal cyclohexane-1,3-dione derivatives

Abstract

The invention concerns novel compounds of the formula I ##STR1## wherein: m is an integer selected from 1 to 4; n is zero or an integer selected from 1 to 4; x are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino, the group --(CH.sub.2).sub.p C(.dbd.A)Z in which p is zero or one A is oxygen or sulfur, and Z is hydrogen, hydroxy, alkoxy, alkylthio, alkyl, substituted alkyl, amino or substituted amino; the group --NHC(.dbd.B(NR.sup.7 R.sup.8 in which B is oxygen or sulfur and R.sup.7 and R.sup.8 are hydrogen or alkyl; R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation; R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl; R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; and R.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl. The compounds of the invention show herbicidal properties and plant growth regulating properties and in further embodiments the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of the compounds of formula I, compositions containing as active ingredient a compound of formula I, and herbicidal and plant growth regulating processes utilizing compounds of formula I.

A compound of formula I ##STR8## wherein:

m is an integer selected from 1 to 4;
n is zero or an integer selected from 1 to 4;
X, which may be the same or different, are independently selected from the group consisting of:
halogen;
nitro;
cyano;
C.sub.1 to C.sub.6 alkyl;
C.sub.1 to C.sub.6 alkyl substituted with halogen or cyano;
hydroxy;
C.sub.1 to C.sub.6 alkoxy;
C.sub.1 to C.sub.6 alkylthio;
sulfamoyl;
N-(C.sub.1 to C.sub.6 alkyl)sulfamoyl;
N,N-di(C.sub.1 to C.sub.6 alkyl)sulfamoyl;
the group --(CH.sub.2).sub.p C(.dbd.A)Z wherein p is zero or one, A is selected from oxygen and sulfur, and Z is selected from the group consisting of hydrogen, hydroxy, C.sub.1 to C.sub.6 alkoxy, C.sub.1 to C.sub.6 alkylthio, amino, N-(C.sub.1 to C.sub.6 alkyl)amino, N,N-di(C.sub.1 to C.sub.6 alkyl)amino, N-(C.sub.1 to .sub.6 alkanoyl)amino, C.sub.1 to C.sub.6 alkyl, and C.sub.1 to C.sub.6 haloalkyl;
the group --NR.sup.5 R.sup.6 wherein R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub. 2 to C.sub.6 alkanoyl, C.sub.2 to C.sub.6 haloalkanoyl, C.sub.1 to C.sub.6 alkylsulfonyl, and benzoyl;
the group --NHC(.dbd.B)NR.sup.7 R.sup.8 wherein B is selected from oxygen and sulfur and R.sup.7 and R.sup.8 are independently selected from hydrogen and C.sub.1 to C.sub.6 alkyl;
and the group --(CH.sub.2)q-- which bridged two adjacent carbon atoms of the benzene ring and wherein q is an integer selected from 3 or 4;
R.sup.1 is selected from the group consisting of:
hydrogen;
C.sub.2 to C.sub.6 alkanoyl;
benzoyl and substituted benzoyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, nitro, C.sub.1 to C.sub.6 alkyl and C.sub.1 to C.sub.6 alkoxy:
benzenesulfonyl and substituted benzenesulfonyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, nitro, C.sub.1 to C.sub.6 alkyl and C.sub.1 C.sub.6 alkoxy;
and an inorganic or an organic cation selected from the alkali metals, the alkaline earth metals the transition metals the ammonium ion and the tri- and tetra(alkyl)ammonium ions wherein alkyl is selected from C.sub.1 to C.sub.6 alkyl and C.sub.1 to C.sub.6 hydroxyalkyl;
R.sup.2 is selected from the group consisting of:
C.sub.1 to C.sub.6 alkyl;
C.sub.2 to C.sub.6 alkenyl;
C.sub.2 to C.sub.6 haloalkenyl;
C.sub.2 to C.sub.6 alkynyl, C.sub.3 to C.sub.6 haloalkynyl;
and substituted C.sub.1 to C.sub.6 alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of halogen, C.sub.1 to C.sub.6 alkoxy, C.sub.1 to C.sub.6 alkylthio, phenyl and substituted phenyl wherein the benzene ring is substituted with from one to three substituents selected 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, and C.sub.1 to C.sub.6 alkylthio;
R.sup.3 is selected from the group consisting of:
C.sub.1 to C.sub.6 alkyl;
C.sub.1 to C.sub.6 fluoroalkyl;
C.sub.2 to C.sub.6 alkenyl;
C.sub.2 to C.sub.6 alkynyl;
and phenyl;
and
R.sub.4 is selected from the group consisting of:
hydrogen;
halogen;
cyano;
C.sub.1 to C.sub.6 alkyl;
and (C.sub.1 to C.sub.6 alkoxy)carbonyl.

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Herbicidal cyclohexane-1,3-dione derivatives

Life of this patent

Herbicidal cyclohexane-1,3-dione derivatives

Life of this patent

Abstract

Claims12