Milbemycin derivatives, their preparation and their use

A method of protecting animals or plants from damage by parasites selected from the group consisting of acarids, helminths and insects, which comprises applying an effective parasiticidal amount of an active compound to said animals, to said plants or to seeds of said plants or to a locus including said animals, plants or seeds, wherein the active compound is selected from the group consisting of at least one compound of formula (I).sub.w or a salt thereof ##STR23## in which:

• R.sub.w.sup.1 and R.sup.2.sub.w are independently selected from the group consisting of:
• hydrogen atoms;
• halogen atoms;
• cyano groups;
• nitro groups;
• C.sub.1 -C.sub.4 alkyl groups;
• substituted C.sub.1 -C.sub.4 alkyl groups having at least one substituent selected from the group consisting of substituents (a), defined below;
• C.sub.1 -C.sub.4 alkoxy groups;
• C.sub.2 -C.sub.6 alkoxyalkoxy groups;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NHR.sub.w.sup.9,
• in which:
• n.sub.w represents 0 or the integer 1 or 2, and R.sub.w.sup.9 represents a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 C(.dbd.O)R.sub.w.sup.6,
• in which:
• n.sub.w and R.sub.w.sup.9 are as defined above, and
• R.sub.w.sup.6 represents:
• a hydrogen atom:
• a C.sub.1 -C.sub.4 alkyl group;
• a substituted C.sub.1 -C.sub.4 alkyl group having at least one substituent selected from the group consisting of substituents (b), defined below;
• a C.sub.2 -C.sub.8 aliphatic hydrocarbon group having one or two ethylenically unsaturated carbon-carbon double bonds, said group being unsubstituted or having at least one substituent selected from the group consisting of substituents (b).sub.w, defined below;
• a C.sub.2 -C.sub.8 alkynyl group;
• a substituted C.sub.2 -C.sub.8 alkynyl group having at least one substituent selected from the group consisting of substituents (b).sub.w, defined below;
• a C.sub.3 -C.sub.8 cycloalkyl group;
• a substituted C.sub.3 -C.sub.8 cycloalkyl group having at least one substituent selected from the group consisting of substituents (c).sub.w, defined below;
• a carbocyclic aryl group having from 6 to 14 ring carbon atoms and being unsubstituted or having at least one substituent selected from the group consisting of substituents (c).sub.w, defined below;
• or a heterocyclic group selected from the group consisting of oxiranyl, oxetanyl, aziridinyl, azetidinyl, thiranyl, thietanyl, furyl, thienyl, pyrrolyl, pyridyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, pyranyl, pyrazinyl, piperidinyl, pyridazinyl, pyrimidinyl, benzofuranyl, isobenzofuranyl, benzothienyl, isobenzothienyl, indolyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridynyl, xanthenyl, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, thiazolidinyl, imidazolidinyl, imidazolinyl, oxazolinyl, oxazolidinyl, pyrazolidinyl, piperazyl, tetrahydropyrimidinyl, dihydropyridazinyl, morpholinyl, thiomorpholinyl, indolinyl, tetrahydroquinolyl, pyrrolidonyl, piperidonyl, pyridonyl, thianthrenyl, chromenyl, phenoxathiinyl, 2H-pyrrolyl, isoindolyl, 3H-indolyl, indazolyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, perimidinyl, phenazinylphenothiazinyl, furazanyl, phenoxazinyl, isochromanyl, chromanyl, pyrazolinyl, indolinyl and isoindolinyl said heterocyclic group being unsubstituted or having at least one substituent selected from the group consisting of substituents (c).sub.w, defined below;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 COCOR.sub.w.sup.6
• in which
• n.sub.w, R.sub.w.sup.6 and R.sub.w.sup.9 are as defined above;
• groups of formula --(CH.sub.2).sub.n.sbsb.w R.sub.w.sup.9 COCOOR.sub.w.sup.7
• in which
• n.sub.w and R.sub.w.sup.9 are as defined above and R.sub.w.sup.7 represents a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.8 cycloalkyl group or an aralkyl group as defined below;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 CHR.sub.w.sup.6 NHCOR.sub.w.sup.6
• in which
• n.sub.w, R.sub.w.sup.6 and R.sub.w.sup.9 are as defined above;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 CHR.sub.w.sup.6 NHCONHR.sub.w.sup.6
• in which
• n.sub.w, R.sub.w.sup.6 and R.sub.w.sup.9 are as defined above;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 CHR.sub.w.sup.6 NHCOOR.sub.w.sup.7
• in which
• n.sub.w, R.sup.6, R.sub.w.sup.7 and R.sub.w.sup.9 are as defined above;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 C(.dbd.Y.sub.w)Y.sub.w R.sub.w.sup.6
• in which
• n.sub.w, R.sub.w.sup.6 and R.sub.w.sup.9 are as defined above and the two symbols Y are independently selected from the group consisting of oxygen and sulfur atoms;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 C(.dbd.Y)NR.sub.w.sup.6' R.sub.w.sup.6'
• in which
• n.sub.w, Y.sub.w and R.sub.w.sup.9 are as defined above, and the two symbols R.sub.w.sup.6' are independently selected from the group consisting of R.sub.w.sup.6, or the two, together with the nitrogen atom to which they are attached, form a heterocyclic group selected from the group consisting of aziridinyl, azetidinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrrolidinyl, thiazolidinyl, imidazolidinyl, imidazolonyl, oxazolinyl, oxazolidinyl, pyrazolidinyl, piperazyl, tetrahydropyrimidinyl, dihydropyridazinyl, pyrrolidonyl, piperidonyl, pyridonyl, pyrazolinyl, azepinyl, perhydroazepinyl, oxazepinyl and thiazepinyl;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 C(.dbd.Y.sub.w)NR.sub.w.sup.6" NR.sub.w.sup.6" R.sub.w.sup.6"
• in which
• n.sub.w, Y.sub.w and R.sub.w.sup.9 are as defined above, and each of the symbols R.sub.w.sup.6" is independently selected from the group consisting of R.sub.w.sup.6, or any two of the symbols R.sub.w.sup.6", together with the nitrogen atom to which each is attached, forms a heterocyclic group selected from the group consisting of diaziridine, diazete, diazetidine, pyrazolidine, pyrazoline, 1,2-dihydropyridazine, 1,2,3,4-tetrahydropyridazine, 1,2,5,6-tetrahydropyridazine, perhydropyridazine, 1,2-dihydro-1,2-diazepine and perhydro-1,2-diazepine;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 C(.dbd.Y.sub.w)NR.sub.w.sup.6 NHZ.sub.w
• in which
• n.sub.w, Y.sub.w, R.sub.w.sup.6 and R.sub.w.sup.9 are as defined above and Z represents
• a group of formula --COOR.sub.w.sup.7, in which R.sub.w.sup.7 is as defined above,
• a group of formula --COR.sub.w.sup.6, in which R.sub.w.sup.6 is as defined above, or
• a group of formula --SO.sub.2 R.sub.w.sup.6, in which R.sub.w.sup.6 is as defined above;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 C(.dbd.NR.sub.w.sup.10)NHR.sub.w.sup.10
• in which
• n and R.sub.w.sup.9 are as defined above and the two symbols R.sub.w.sup.10 are independently selected from the group consisting of R.sub.w.sup.6, cyano groups, nitro groups, groups of formula --COOR.sub.w.sup.7, in which R.sub.w.sup.7 is as defined above, and groups of formula --COR.sub.w.sup.6, in which R.sub.w.sup.6 is as defined above;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 C(.dbd.NR.sub.w.sup.10)R.sub.w.sup.6
• in which
• n.sub.w, R.sub.w.sup.6, R.sub.w.sup.9 and R.sub.w.sup.10 are as defined above;
• groups of formula --(CH.sub.2).sub.n.sbsb.w NR.sub.w.sup.9 SO.sub.m.sbsb.w R.sup.6.sub.w
• in which
• n.sub.w, R.sub.w.sup.6 and R.sub.w.sup.9 are as defined above and m is 1 or 2;
• groups of formula --CONHR.sup.6.sub.w
• in which
• R.sub.w.sup.6 is as defined above;
• and
• groups of formula --COOR.sup.7.sub.w
• in which
• R.sup.7.sub.w is as defined above;
• R.sub.w.sup.3 and R.sub.w.sup.4 are independently selected from the group consisting of hydrogen atoms, C.sub.1 -C.sub.4 alkyl groups and C.sub.1 -C.sub.4 alkoxy groups;
• R.sub.w.sup.5 represents a methyl group, an ethyl group, an isopropyl group or a sec-butyl group;
• and
• X.sub.w represents a hydroxy group, a C.sub.1 -C.sub.5 alkanoyloxy group, a substituted C.sub.1 -C.sub.5 alkanoyloxy group having at least one substituent selected from the group consisting of substituents (d), defined below, or a hydroxyimino group;
• said aralkyl groups have from 1 to 4 carbon atoms in the alkyl part from 6 to 10 ring atoms in the aryl part, which is a carbocyclic aryl group which is unsubstituted or has at least one substituent selected from the group consisting of substituents (c), defined below;
• substituents (a)w:
• halogen atoms, C.sub.1 -C.sub.4 alkoxy groups, C.sub.1 -C.sub.4 alkylthio groups and C.sub.1 -C.sub.5 alkanoyloxy groups;
• substituents (b)w:
• C.sub.3 -C.sub.8 cycloalkyl groups;
• C.sub.1 -C.sub.4 alkoxy groups;
• C.sub.1 -C.sub.4 alkylthio groups:
• C.sub.2 -C.sub.5 cyanoalkylthio groups:
• C.sub.2 -C.sub.5 alkoxycarbonyl groups;
• halogen atoms;
• cyano groups;
• nitro groups;
• amino groups;
• carbocyclic aryl groups having from 6 to 10 carbon atoms and being unsubstituted or having at least one substituent selected from the group consisting of substituents (c).sub.w, defined below;
• aromatic heterocyclic groups having from 5 to 8 ring atoms of which from 1 to 4 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur hetero-atoms, said heterocyclic group being monocyclic or fused either to a benzene ring or to a heterocyclic group which has 5 or 6 ring atoms of which from 1 to 3 are nitrogen hetero-atoms and being unsubstituted or having at least one substituent selected from the group consisting of substituents (c).sub.w, defined below;
• and aryloxy and arylthio groups in which the aryl part has from 6 to 10 carbon atoms and is unsubstituted or has at least one substituent selected from the group consisting of substituents (c).sub.w, defined below;
• substituents (c)w:
• C.sub.1 -C.sub.4 alkyl groups, C.sub.1 -C.sub.4 alkoxy groups, C.sub.1 -C.sub.4 alkylthio groups, C.sub.1 -C.sub.5 alkanoyloxy groups, C.sub.2 -C.sub.5 alkoxycarbonyl groups, halogen atoms, cyano groups, nitro groups, amino groups, mono- and di- alkylamino groups in which the or each alkyl part is C.sub.1 -C.sub.4, carbamoyl groups, mono- and di- alkylcarbamoyl groups in which the or each alkyl part is C.sub.1 -C.sub.4, and C.sub.1 -C.sub.5 alkanoylamino groups;
• substituents (d)w:
• halogen atoms, C.sub.1 -C.sub.4 alkoxy groups, C.sub.2 -C.sub.5 alkoxycarbonyl groups and carboxy groups.