N-(substituted amino)imide derivatives, preparation process thereof, and herbicidal composition

A process for preparation of an N-(substituted amino)imide derivative represented by the formula (I-a), which comprises reacting an N-aminoimide derivative of the formula (II-a) with an (azinylureylene)sulfonyl halide of the formula (III):

• ##STR13## wherein Aa is a structure selected from the group consisting of the following formulas (1), (2), (3) and (4) ##STR14## wherein R.sup.2 and R.sup.3 in the formula (1) are independently a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, but not R.sup.2.dbd.R.sup.3 .dbd.H;
• X.sup.1 and X.sup.2 are independently a hydrogen atom, a halogen atom, C.sub.1 -C.sub.4 alkyl group, C.sub.1 -C.sub.4 alkoxy group, C.sub.1 -C.sub.4 alkylthio group, C.sub.1 -C.sub.4 haloalkyl group, C.sub.1 -C.sub.4 haloalkoxy group, C.sub.1 -C.sub.4 haloalkylthio group, C.sub.1 -C.sub.4 alkoxyalkyl group, C.sub.2 -C.sub.4 thioalkoxyalkyl group or NR.sup.7 R.sup.8, wherein R.sup.7 and R.sup.8 are independently a hydrogen atom, C.sub.1 -C.sub.4 alkyl group or C.sub.1 -C.sub.4 alkoxy group;
• Z is a nitrogen atom or CH;
• and Y.sup.1 is a halogen atom.

A process for preparation of an N-(substituted amino) imide derivative represented by the formula (I-b1), which comprises reacting an N-(substituted amino)imide derivative of the formula (I-b2) with a compound represented by the formula (IV) in the presence of a base to replace the hydrogen atom on N-amino group with R.sup.1 b:

• ##STR15## wherein Aa is a structure selected from the group consisting of the following formulas (1), (2) or (3) ##STR16## wherein R.sup.2 and R.sup.3 in the formula (1) are independently a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, but not R.sup.2 .dbd.R.sup.3 .dbd.H;
• X.sup.1 and X.sup.2 are independently a hydrogen atom, a halogen atom, C.sub.1 -C.sub.4 alkyl group, C.sub.1 -C.sub.4 alkoxy group, C.sub.1 -C.sub.4 alkylthio group, C.sub.1 -C.sub.4 haloalkyl group, C.sub.1 -C.sub.4 haloalkoxy group, C.sub.1 -C.sub.4 haloalkylthio group, C.sub.2 -C.sub.4 alkoxyalkyl group, C.sub.2 -C.sub.4 thioalkoxyalkyl group or NR.sup.7 R.sup.8, wherein R.sup.7 and R.sup.8 are independently hydrogen atom, C.sub.1 -C.sub.4 alkyl group or C.sub.1 -C.sub.4 alkoxy group;
• Z is a nitrogen atom or CH;
• R.sup.1 b is C.sub.1 -C.sub.4 alkyl group, C.sub.7 -C.sub.9 aralkyl group, C.sub.1 -C.sub.4 haloalkyl group, (C.sub.1 -C.sub.4 alkyl)carbonyl group or (C.sub.1 -C.sub.4 alkyl)sulfonyl group;
• and Y.sup.2 is a halogen atom or ›C.sub.1 -C.sub.4 alkyl) carbonyl!oxy group.

A herbicidal composition which comprises a herbicidally effective amount of an N-(substituted amino)imide derivative represented by the formula (I) as an active ingredient and a carrier therefor, ##STR18## wherein, R.sup.1 is a hydrogen atom, C.sub.7 -C.sub.9 alkyl group, C.sub.1 -C.sub.4 aralkyl group, C.sub.1 -C.sub.4 haloalkyl group, (C.sub.1 -C.sub.4 alkyl)carbonyl group or (C.sub.1 -C.sub.4 alkyl)sulfonyl group;

• A represents a structure selected from the group consisting of the following formulas (1), (2), (3) and (4) ##STR19## wherein R.sup.2 and R.sup.3 in the (1) are independently a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, but not R.sup.2 .dbd.R.sup.3 .dbd.H;
• X.sup.1 and X.sup.2 are independently a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, C.sub.1 -C.sub.4 alkoxy group, C.sub.1 -C.sub.4 alkylthio group, C.sub.1 -C.sub.4 haloalkyl group, C.sub.1 -C.sub.4 haloalkoxy group, C.sub.1 -C.sub.4 haloalkylthio group, C.sub.2 -C.sub.4 alkoxyalkyl group, C.sub.2 -C.sub.4 thioalkoxyalkyl group or NR.sup.7 ;
• R.sup.8, wherein R.sup.7 and R.sup.8 are independently a hydrogen atom, C.sub.1 -C.sub.4 alkyl group or C.sub.1 -C.sub.4 alkoxy group;
• and Z is a nitrogen atom or CH.