Sankyo Company, Limited

Ciba-geigy Corporation

Toshimitsu Toyama

Akio Saito

Yasuhiro Morisawa

Susumu Kaneko

Kazuo Sato

Anthony Cornelius O'Sullivan

Toshiaki Yanai

Bruno Frei

Takao Kinoto

Keiji Tanaka

Akira Nishida

Jean-Claude Gehret

Satoru Naito

Louis-Pierre Molleyres

Toshihiko Nanba

Yoko Sugiyama

13-substituted milbemycin derivatives, their preparation and their use against insects and other pests

Compounds of formula (I): ##STR1## wherein: R.sup.1 is methyl, ethyl, isopropyl or sec-butyl; X is carbonyl or methylene; Z is .dbd.C.dbd.(R.sup.2).sub.2 or .dbd.C.dbd.(CH.sub.2).sub.m, in which R.sup.2 is alkyl, and m is integer of from 2 to 5); n is 0 or 1; R.sup.3 is nitro, amino, alkylamino, dialkylamino, alkoxy, alkoxyalkoxy, or a group (iii), (iv), (v), (vi), (vii), (viii) or (ix): ##STR2## , wherein: R.sup.4 represents: alkyl; substituted alkyl; cycloalkyl having from 3 to 6 carbon atoms; substituted cycloalkyl; alkenyl; alkynyl; carbocyclic aryl; or heterocyclic; R.sup.5 is hydrogen atom or alkyl; R.sup.6 represents: hydrogen; alkyl; or cycloalkyl; R.sup.7 represents: alkyl; cycloalkyl; carbocyclic aryl; or aralkyl; or R.sup.6 and R.sup.7, together with the nitrogen atom to which they are attached, are fuised to form heterocyclic ring; Y is oxygen or sulfur; r is 1, 2 or 3; Q is methylene or carbonyl; R.sup.8 is: alkyl or carbocyclic aryl; R.sup.9 is: alkyl; cycloalkyl; carbocyclic aryl; or aralkyl; R.sup.10 is heterocyclic; and R.sup.11 is aLkyl; have valuable acaricidal, insecticidal and anthelmintic activities.

13-substituted milbemycin 5-oxime derivatives, their preparation and

Compounds of formula (I): ##STR1## and of formula (I).sub.w : ##STR2## in which: A represents group having one of the following formulae: ##STR3## wherein R.sup.2, R.sup.3 and R.sup.4 are independently selected from the group consisting of hydrogen atoms, halogen atoms, alkyl groups having from 1 to 4 carbon atoms, and alkoxy groups having from 1 to 4 carbon atoms;

Milbemycin derivatives, their preparation and their use

Compounds of formula (I): ##STR1## and salts and esters thereof have valuable anthelmintic, acaricidal and insecticidal activities. Methods of preparing the compounds are also provided.

Milbemycin ether derivatives, their preparation and their therapeutic

Compounds of formula (I): ##STR1## thereof have valuable anthelmintic, acaricidal and insecticidal activities.

Compounds having a 16-membered macrolide ring, and related to the milbemycins and avermectins, with substituents at positions 5.13, 25 and optionally also 23, have acaricidal, insecticidal and anthelmintic properties. They are useful for treating various pests in plants and animals.

Macrolide compounds, their preparation and their use

Compounds of formula (I): ##STR1## in which: R.sup.1 is a variety of organic groups; R.sup.5 is methyl, ethyl, isopropyl or sec-butyl; and X is hydroxy, alkanoyloxy or hydroxyimino and salts and esters thereof have valuable anthelmintic, acaricidal and insecticidal activities. Methods of preparing the compounds are also provided.

Compounds having a 16-membered macrolide ring, and related to the milbemycins and avermectins, with substituents at positions 5, 13, 25 and optionally also 23, have acaricidal, insecticidal and anthelmintic properties. They are useful for treating various pests in plants and animals.

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Tokyo, Japan

Toshimitsu Toyama