6-chloro-2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid imino ester derivatives, processes for their production and a method for their application as herbicides

A process of preparing a 6-chloro-2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid imino ester compound of formula (I):

• ##STR136## wherein Q represents a straight or branched alkyl group having from 1 to 10 carbon atoms, a straight or branched alkenyl group having 2 to 10 carbon atoms, or a cycloalkyl group having from 3 to 10 carbon atoms, which may be substituted with a (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio group;
• a (C.sub.1 -C.sub.4)alkyl or (C.sub.2 -C.sub.4)alkenylthio group;
• a phenylthio group;
• a phenyl(C.sub.1 -C.sub.4)alkyl or phenyl(C.sub.2 -C.sub.4)alkenylthio group;
• or a radical of the following formula:
• ##STR137## wherein R.sup.1 and R.sup.2 are the same or different from each other and represent hydrogen or a halogen atom;
• or a group selected from the groups consisting of a (C.sub.1 -C.sub.4)alkyl, a (C.sub.2 -C.sub.4)alkenyl, an acyl, an acyloxy, a (C.sub.1 -C.sub.4)alkylthio, a nitro, a cyano, a phenyl and a phenoxy group, and which, if necessary, may be substituted with a halogen atom, a (C.sub.1 -C.sub.4)alkyl, a (C.sub.1 -C.sub.4)alkoxy or an acetal group;
• or R.sup.1 and R.sup.2 may constitute an acetal structure with carbon atoms to which R.sup.1 and R.sup.2 are linked;
• and, n is 0 or 1;
• or R.sup.1 and R.sup.2 together form 3', 4'-methylenedioxy;
• and
• R represents hydrogen or a halogen atom, a cyano group, or -Z-R.sup.3, wherein R.sup.3 represents a (C.sub.1 -C.sub.4)alkyl, an alkoxy group having from 1 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, or a phenyl, a phenoxy or an amino group, or 5-6 membered hetero or aromatic ring system which is a phenyl, a furyl, a thienyl, a pyrrolyl or a pyranyl group, connecting to Z through a (C.sub.1 -C.sub.2)alkyl or alkoxy bridge, which may have one or more proper substituents selected from the group consisting of a halogen atom, a (C.sub.1 -C.sub.4)alkyl, a hydroxy, a nitro or a cyano group on its certain positions, or in some cases, R.sup.3 may be cyclized with Z to form a morpholine or R.sup.3 may be cyclized with Z and Q, to form ##STR138## and which may have methyl and/or phenyl substituents;
• and, Z represents --O--, --S--, ##STR139## wherein R.sup.4 is a hydrogen atom, a (C.sub.1 -C.sub.4)alkyl or a phenyl group, or constitutes a 5-6 membered cyclic system containing an oxygen atom with R.sup.3 which comprises reacting the compound of the following formula (II) and the compound of the following formula (III) in the presence of a solvent ##STR140## wherein, R and Q are as defined above.

A 6-chloro-2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid imino ester compound of the formula (I):

• ##STR141## wherein Q represents a straight or branched alkyl group having from 1 to 10 carbon atoms, a straight or branched alkenyl group having 2 to 10 carbon atoms, or a cycloalkyl group having from 3 to 10 carbon atoms, which may be substituted with a (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio group;
• a (C.sub.1 -C.sub.4)alkyl or (C.sub.2 -C.sub.4)alkenylthio group;
• a phenylthio group;
• a phenyl(C.sub.1 -C.sub.4)alkyl or phenyl(C.sub.2 -C.sub.4)alkenylthio group;
• or a radical of the following formula:
• ##STR142## wherein R.sup.1 and R.sup.2 are the same or different from each other and represent hydrogen or a halogen atom, or a first group selected from the groups consisting of a (C.sub.1 -C.sub.4)alkyl, a (C.sub.2 -C.sub.4)alkenyl, an acyl, an acyloxy, a (C.sub.1 -C.sub.4)alkylthio, a nitro, a cyano, a phenyl and a phenoxy group;
• or R.sup.1 and R.sup.2 may constitute an acetal structure with carbon atoms to which R.sup.1 and R.sup.2 are linked;
• and, n is 0 or 1;
• or R.sup.1 and R.sup.2 together form 3',4'-methylenedioxy;
• and
• R represents a hydrogen or a halogen atom, a cyano group, or -Z-R.sup.3, wherein R.sup.3 represents a (C.sub.1 -C.sub.4)alkyl group, an alkoxy group having from 1 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, or a phenyl, a phenoxy or an amino group, or a 5-6 membered hetero or aromatic ring system, which is a phenyl, a furyl, a thienyl, a pyrrolyl or a pyranyl group, connecting to Z through a (C.sub.1 -C.sub.2)alkyl or alkoxy bridge, which may have one or more substituents selected from the group consisting of a halogen atom, a (C.sub.1 -C.sub.4)alkyl, a hydroxy, a nitro or a cyano group;
• and, Z represents --O--, --S--, ##STR143## wherein R.sup.4 is a hydrogen atom, a (C.sub.1 -C.sub.4)alkyl or a phenyl group, or a 5-6 membered cyclic system containing an oxygen atom with R.sup.3.

A process of preparing a 6-chloro-2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid imino ester compound of formula (I):

• ##STR144## wherein, Q represents a straight or branched alkyl group having from 1 to 10 carbon atoms, a straight or branched alkenyl group having 2 to 10 carbon atoms or a cycloalkyl group having from 3 to 10 carbon atoms, which may be substituted with a (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio group;
• a (C.sub.1 -C.sub.4)alkyl or (C.sub.2 -C.sub.4)alkenylthio group;
• a phenylthio group;
• a phenyl(C.sub.1 -C.sub.4)alkyl or phenyl(C.sub.2 -C.sub.4)alkenylthio group;
• or a radical of the following formula:
• ##STR145## wherein R.sup.1 and R.sup.2 are the same or different from each other and represent hydrogen or a halogen atom;
• or a first group selected from the groups consisting of a (C.sub.1 -C.sub.4)alkyl, a (C.sub.2 -C.sub.4)alkenyl, an acyl, an acyloxy, a (C.sub.1 -C.sub.4)alkylthio, a nitro, a cyano, a phenyl and a phenoxy group;
• or R.sup.1 and R.sup.2 may constitute an acetal structure with carbon atoms to which R.sup.1 and R.sup.2 are linked;
• and, n is 0 or 1;
• or R.sup.1 and R.sup.2 together form 3,40 ,4'-methylenedioxy;
• and,
• R represents a hydrogen or a halogen atom, a cyano group, or -Z-R.sup.3, wherein R.sup.3 includes a (C.sub.1 -C.sub.4)alkyl group, an alkoxy group having from 1 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, or a phenyl, a phenoxy or an amino group, or a 5-6 membered hetero or aromatic ring system, which is a phenyl, a furyl, a thienyl, a pyrrolyl or a pyranyl group, connecting to Z through a (C.sub.1 -C.sub.2)alkyl or alkoxy bridge, which may have one or more substituents selected from the group consisting of a halogen atom, a (C.sub.1 -C.sub.4)alkyl, a hydroxy, a nitro or a cyano group;
• and, Z represents --O--, --S--, ##STR146## wherein R.sup.4 is a hydrogen atom, a (C.sub.1 -C.sub.4)alkyl or a phenyl group, or a 5-6 membered cyclic system containing an oxygen atom with R.sup.3 which comprises reacting the compound of the following formula (II) and the compound of the following formula (III) in the presence of a solvent ##STR147## wherein, R and Q are as defined above.