Milbemycin ether derivatives, their preparation and their therapeutic and agrochemical uses

A compound of the formula (I):

• ##STR28## in which:
• R.sup.1 represents:
• a cycloalkyl group having from 4 to 8 carbon atoms;
• an alkyl group having from 1 to 4 carbon atoms and substituted by a cycloalkyl group having from 3 to 8 carbon atoms, said cycloalkyl group being unsubtituted or having at least one substituent selected from the group consisting of substituents (c);
• or a group having the following formula:
• ##STR29## wherein:
• R.sup.2 represents:
• a hydrogen atom;
• a halogen atom;
• a cyano group;
• a nitro group;
• an alkyl group having from 1 to 4 carbon atoms;
• a substituted alkyl group which has from 1 to 4 carbon atoms and which has at least one substituent selected from the group consisting of substituents (a);
• an alkoxy group having from 1 to 4 carbon atoms;
• an alkoxyalkoxy group having a total of from 2 to 6 carbon atoms;
• or a group having one of the following formulae:
• --(CH.sub.2).sub.n NHR.sup.9
• --(CH.sub.2).sub.n NR.sup.9 COR.sup.6
• --(CH.sub.2).sub.n NR.sup.9 COCOR.sup.6
• --(CH.sub.2).sub.n NR.sup.9 COCOOR.sup.7
• --(CH.sub.2).sub.n NR.sup.9 CHR.sup.6 NHCOR.sup.6
• --(CH.sub.2).sub.n NR.sup.9 CHR.sup.6 NHCONHR.sup.6
• --(CH.sub.2).sub.n NR.sup.9 CHR.sup.6 NHCOOR.sup.7
• --(CH.sub.2).sub.n NR.sup.9 C(=Y)YR.sup.6
• --(Ch.sub.2).sub.n NR.sup.9 C(=Y)NR.sup.6 R.sup.6
• --(CH.sub.2).sub.n NR.sup.9 C(=Y)NR.sup.6 NR.sup.6 R.sup.6
• --(CH.sub.2).sub.n NR.sup.9 C(=Y)NR.sup.6 NHZ
• --(CH.sub.2).sub.n NR.sup.9 C(=NR.sup.10)NHR.sup.10
• --(CH.sub.2).sub.n NR.sup.9 C(=NR.sup.10)R.sup.6 or
• --(CH.sub.2).sub.n NR.sup.9 SO.sub.m R.sup.6
• wherein:
• m is 1 or 2;
• n is 0, 1 or 2;
• R.sup.6 represents a hydrogen atom;
• an alkyl group having from 1 to 8 carbon atoms;
• a substituted alkyl group having from 1 to 8 carbon atoms and having at least one substituent selected from the group consisting of substituents (b);
• an aliphatic hydrocarbon group having from 2 to 8 carbon atoms and having one or two carbon-carbon double or triple bonds;
• a cycloalkyl group having from 3 to 8 carbon atoms;
• a substituted cycloalkyl group having from 3 to 8 carbon atoms and having at least one substituent selected from the group consisting of substituents (c);
• an aryl group which has from 6 to 14 ring carbon atoms and which is unsubstituted or which has at least one substituent selected from the group consisting of substituents (c);
• an aryloxy group which has from 6 to 14 ring carbon atoms and which is unsubstituted or which has at least one substituent selected from the group consisting of substituents (c);
• an arylthio group which has from 6 to 14 ring carbon atoms and which is unsubstituted or which has at least one substituent selected from the group consisting of substituents (c);
• and, where there are two or more groups or atoms represented by R.sup.6, these are the same or different from each other;
• R.sup.7 represents an alkyl group having from 1 to 4 carbon atoms, a cycloalkyl group having from 3 to 7 carbon atoms, or an aralkyl group in which an alkyl group having from 1 to 4 carbon atoms is substituted by from 1 to 3 aryl groups which have from 6 to 10 ring carbon atoms and which have at least one substituent selected from the group consisting of substituents (c);
• R.sup.9 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
• R.sup.10 represents any of the groups or atoms defined above for R.sup.6, or it represents a cyano group, a nitro group, a group of formula --COOR.sup.7, wherein R.sup.7 is as defined above, or a group of formula --COR.sup.6, wherein R.sup.6 is as defined above;
• Y represents an oxygen atom or a sulfur atom;
• and, where there are two or more groups represented by Y, these are the same or different from each other;
• Z represents a group of formula --COOR.sup.7, wherein R.sup.7 is as defined above, a group of formula --COR.sup.6, wherein R.sup.6 is as defined above, or a group of formula --SO.sub.2 R.sup.6, wherein R.sup.6 is as defined above;
• Q represents a methylene group, an ethylene group or a group of formula --OCH.sub.2 --;
• R.sup.5 represents a methyl group, an ethyl group, an isopropyl group or a sec-butyl group;
• and
• X represents:
• a hydroxy group;
• an alkanoyloxy group which has from 1 to 5 carbon atoms, and which is unsubstituted or has at least one substituent selected from the group consisting of substituents (d);
• or a hydroxyimino group;
• substituents (a):
• halogen atomes, alkoxy groups having from 1 to 4 carbon atoms, alkylthio groups having from 1 to 4 carbon atoms, and alkanoyloxy groups having from 1 to 5 carbon atoms;
• substituents (b):
• cycloalkyl groups having from 3 to 8 carbon atoms;
• alkoxy groups having from 1 to 4 carbon atoms;
• alkylthio groups having from 1 to 4 carbon atoms;
• cyanoalkylthio groups having from 2 to 5 carbon atoms;
• alkoxycarbonyl groups having from 2 to 5 carbon atoms;
• halogen atoms;
• cyano groups;
• nitro groups;
• amino groups;
• aryl groups which have from 6 to 14 ring carbon atoms and which are unsubstituted or have at least one substitutent selected from the group consisting of substituents (c);
• aryloxy groups which have from 6 to 14 ring carbon atoms and which are unsubstituted or have at least one substituent selected from the group consisting of substituents (c);
• and arylthio groups which have from 6 to 14 ring carbon atoms and which are unsubstituted or have at least one substituent selected from the group consisting of substitutents (c);
• substituents (c):
• alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, alkylthio groups having from 1 to 4 carbon atoms, alkanoyloxy groups having from 1 to 5 carbon atoms, alkoxycarbonyl groups having from 2 to 5 carbon atoms, halogen atoms, cyano groups, nitro groups, amino groups, alkylamino groups in which the alkyl parts has from 1 to 4 carbon atoms, dialkylamino groups in which each alkyl part is independently selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, carbamoyl groups, alkylcarbamoyl groups in which the alkyl part has from 1 to 4 carbon atoms, dialkylcarbamoyl groups in which each alkyl part is independently selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, and alkanoylamino groups having from 1 to 5 carbon atoms;
• substituents (d):
• halogen atoms, alkoxy groups having from 1 to 4 carbon atoms, alkoxycarbonyl groups having from 2 to 5 carbon atoms, and carboxy groups.