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Details
Inventors: Okazaki, Takao; Takahashi, Shuji; Iwado, Seigo; Tanaka, Keiji; Yanai, Toshiaki; Kajino, Hisaki;
Assignee: Sankyo Company Limited (Tokyo, JP)
Primary Examiner: Rollins; John W.
Assistant Examiner:
Attorney, Agent or Firm: Frishauf, Holtz Goodman & Woodward

Compounds with acaricidal, insecticidal and anthelmintic activities have the formula: ##STR1## wherein: --X--Y-- is selected from the group consisting of --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CHOH--, --CH.dbd.CH--, and --CH.sub.2 --C(.dbd.O)--; R.sup.1 is selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, a sec-butyl group and groups of formula --C(CH.sub.3).dbd.CHR.sup.5 in which R.sup.5 is selected from the group consisting of a methyl group, an ethyl group and an isopropyl group; R.sup.2 represents a group of formula --(CH.sub.2).sub.n --C(R.sup.6).dbd.C(R.sup.7)(R.sup.8) in which n is 0, 1 or 2, R.sup.6 and R.sup.7 each is selected from the group consisting of a hydrogen atom and a methyl group and R.sup.8 is selected from the group consisting of a hydrogen atom, a C.sub.1-4 alkyl group, a phenyl group and a phenyl group substituted with at least one substituent selected from the group consisting of halogen, methyl and nitro substitutents; R.sup.3 is selected from the group consisting of a hydrogen atom, a methyl group, a hydroxy-protecting group, an ester-forming carboxylic acid residue, and an ester-forming carbonic acid residue; and R.sup.4 is selected from the group consisting of a hydrogen atom and an .alpha.-L-oleandrosyl-.alpha.-L-oleandrosyloxy group, with the proviso that R.sup.4 represents a hydrogen atom when the group R.sup.1 is selected from the group consisting of a methyl group, an ethyl group, and groups of formula --C(CH.sub.3).dbd.CHR.sup.5 in which R.sup.5 is selected from the group consisting of a methyl group, an ethyl group and an isopropyl group.

DETAILED DESCRIPTION OF THE PRESENT INVENTION In the compounds of formula (I), where R.
sup.
2 represents a group of the formula --C(CH.
sub.
3).
dbd.
CHR.
sup.
5, the group R.
sup.
2 is a 1-methyl-1-propenyl, 1-methyl-1-butenyl or 1,3-dimethyl-1-butenyl group.
Where R.
sup.
3 is a hydroxy-protecting group, it may be any of those conventionally employed for this purpose.
For example, the protecting group may be a silyl group represented by the formula Si(R')(R")(R'") in which R', R" and R'" each represents a C.
sub.
1-4 alkyl group, a benzyl group or a phenyl group.
Examples of the silyl group include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, diisopropylmethylsilyl, t-butyldimethylsilyl, dimethylphenylsilyl, t-butyldiphenylsilyl, triphenylsilyl and tribenzylsilyl groups.
Amongst these groups, trimethylsilyl, triethylsilyl and t-butyldimethylsilyl groups are preferred.
The protecting group can also be a residue of a carboxylic or carbonic acid residue, as separately mentioned.
When R.
sup.
3 is an acid residue, there is no particular limitation on the nature of the acid, and it can be selected from a wide variety of carboxylic acids and carbonic acids, since it appears that the biological activity of compounds of formula (I) is attributable to the formation of compounds in which --OR.
sup.
3 is a hydroxy group.
As mentioned above, the literature contains many examples of suitable acids for forming 5-esterified milbemycins, and such acids can readily be adopted for the compounds of the present invention.
Without being exhaustive, R.
sup.
3 when a residue of an ester-forming carboxylic or carbonic acid can be of the formula --CO--(O).
sub.
n --R.
sup.
11, wherein is 0 or 1; and R.
sup.
11 represents a straight or branched chain C.
sub.
1-18 alkyl group, a C.
sub.
3-7 cycloalkyl group, a C.
sub.
7-9 aralkyl group, a C.
sub.
2-6 alkenyl or alkynyl group, a C.
sub.
6-10 aryl group or a monocyclic or fused heterocyclic group having from 5 to 10 ring atoms and containing at least one oxygen, sulfur or nitrogen atom



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