American Cyanamid Company

Michael V Ramsay

Derek R Sutherland

David Noble

Richard A Fletton

John B Ward

Hazel M Noble

Neil Porter

Edward P Tiley

Oswy Z Pereira

Richard Bell

Brian M Bain

Gordon C Lawrence

Michael J Dawson

Peter D Howes

Stephen Freeman

Stephen J Lane

Simon C Dolan

Derek N Evans

Paul F Lambeth

Alison C Rosemeyer

Compounds of formula (I) ##STR1## and salts thereof wherein R.sup.1 is a methyl, ethyl or isopropyl group;

Macrolide compounds

Compounds of formula (I) ##STR1## and salts thereof, wherein R.sup.1 represents a methyl, ethyl or ispropyl group; R.sup.2 represents a C.sub.2-7 alkyl group interrupted by an oxygen or sulphur atom or an aryl, aryl C.sub.1-7 alkyl or heteroaryl C.sub.1-7 alkyl group; OR.sup.3 is a hydroxyl group or a substituted hydroxyl group having up to 25 carbon atoms; and the group .dbd.NOR.sup.2 is in the E configuration. These compounds may be used for controlling insect, acarine, nematode or other pests.

Compounds of formula (1) ##STR1## wherein R represents a sugar residue or an acylated derivative thereof;

Compounds of formula (1) ##STR1## wherein R.sup.1 represents a methyl, ethyl or isopropyl group; Y.sup.1 is --CH.sub.2 --, Y.sup.2 is --CH-- and X represents ##STR2## [where R.sup.2 represents a hydrogen atom or a group OR.sup.6 (where OR.sup.6 is a hydroxy group or a substituted hydroxyl group having up to 25 carbon atoms) and R.sup.3 represents a hydrogen atom, or R.sup.2 and R.sup.3 together with the carbon atom to which they are attached represent &gt;C.dbd.O, &gt;C.dbd.CH.sub.2 or &gt;C.dbd.NOR.sup.7 (where R.sup.7 represents a hydrogen atom, a C.sub.1-8 alkyl group or a C.sub.3-8 alkenyl group and the group &gt;C.dbd.NOR.sup.7 is in the E configuration)] or --Y.sup.1 --X--Y.sup.2 represents --CH.dbd.CH--CH-- or --CH.sub.2 --CH.dbd.C--; R.sup.4 represents a group OR.sup.6 as defined above and R.sup.5 represents a hydrogen atom, or R.sup.4 and R.sup.5 together with the carbon atom to which they are attached represent &gt;C.dbd.O or &gt;C.dbd.NOR.sup.7a ( where R.sup.7a is as defined above for R.sup.7); and one of R.sup.8 and R.sup.9 represents an alkoxyalkoxy group optionally interrupted by an oxygen atom or an alkoxy group and the other represents a hydrogen atom or R.sup.8 and R.sup.9 together with the carbon atom to which they are attached represent &gt;C.dbd.NOR.sup.7b (where R.sup.7b is as defined above for R.sup.7), and salts thereof. These compounds may be used to control nematode, acarine, insect or other pests.

Compounds of formula (I) ##STR1## and salts thereof, wherein R is a C.sub.1-4 alkyl group, R.sup.1 is a methyl, ethyl or isopropyl group; and OR.sup.2 is a hydroxyl or substituted hydroxyl group having up to 25 carbon atoms. These compounds may be used for controlling insect, acarine, nematode or other pests.

Compounds of formula (1) ##STR1## and salts thereof, wherein R.sup.1 represents a methyl, ethyl or isopropyl group;

A process for the preparation of a compound of formula (I) ##STR1## (in which R.sup.1 is methyl, ethyl or isopropyl) by hydrogenation of a corresponding compound having a double bond at the 22,23-position, for example in the presence of a rhodium catalyst.

Preparation of macrolide compounds

A process for preparing a compound of formula (I) ##STR1## (where (i) R.sup.1 is an ethoxy group and R.sup.2 is a hydrogen atom, (ii) R.sup.1 is a hydrogen atom and R.sup.2 is a bromine atom or (iii) (R.sup.1 and R.sup.2 together with the carbon atom to which they are attached represent&gt;C.dbd.O) which comprises stereoselectively reducing the corresponding 5-keto compound.

Process for the preparation of macrolide compounds

Compounds are described of formula (1) ##STR1## and salts thereof wherein R.sup.1 is a methyl, ethyl or isopropyl group;

Compounds are described of formula (I) ##STR1## and salts therof, wherein R.sup.1 represents a methyl, ethyl or isopropyl group;

Macrolide antibiotics

Compounds are described of formula (II) ##STR1## and salts thereof, wherein R.sup.1 reprsents a methyl, ethyl or isopropyl group;

Macrolide antibiotics and their preparation

Compounds are described of formula (I) ##STR1## and salts thereof, wherein OR is a hydroxyl group or a substituted hydroxyl group having up to 25 carbon atoms, R.sup.1 represents a methyl, ethyl or isopropyl group and the broken line represents a double bond at the 22,23-position or at the 23,24-position. These compounds may be used for controlling insect, acarine, nematode or other pests.

A process is described for preparing a compound of formula (I) ##STR1## (in which R.sup.1 represents a methyl, ethyl or isopropyl group, R.sup.2 represents a hydrogen atom or a methyl or acetyl group and R.sup.3 represents a hydrogen atom, or OR.sup.2 and R.sup.3 together with the carbon atom to which they are attached represent the group &gt;C.dbd.0) which comprises treating a corresponding 23.alpha.- compound with a triethyloxonium salt.

A process for preparing the compound of formula (I) ##STR1## which comprises treating the corresponding 23.alpha.-compound sequentially with (i) oxalyl chloride and (ii) 2-mercaptopyridine-N-oxide, a catalytic amount of an organic base, and a thiol.

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South Harrow, United Kingdom

Michael V Ramsay