Ciba-geigy Corporation

Sankyo Company, Limited

Bruno Frei

Anthony Cornelius O'Sullivan

Kazuo Sato

Toshiaki Yanai

Akira Nishida

Peter Maienfisch

Jean-Claude Gehret

Toshimitsu Toyama

Keiji Tanaka

Takao Kinoto

Noritoshi Kitano

Oreste Ghisalba

Hans-Peter Schar

Hari B Mereyala

Anthony C Sullivan

Gerado Ramos

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

The present invention relates to a one-step microbial process for the preparation of 13.beta.-hydroxy- or 14,15-epoxy-milbemycins of the following formulae I and II ##STR1## in which R.sub.1 and R.sub.1 ' represent methyl, ethyl, isopropyl or sec.-butyl or represent the group ##STR2## in which X represents methyl, ethyl or isopropyl, and A and A' represent the group ##STR3## in which R.sub.2 represents hydrogen, --C(O)-CH.sub.2 O-C(O)-CH.sub.2 CH.sub.2 -COOH or --C(O)-CH.sub.2 CH.sub.2 -COOH, or mixtures of compounds of the formulae I and II, which process comprises bringing a milbemycin of the formula III ##STR4## dissolved in a liquid phase, in which R.sub.3 represents R.sub.1 or R.sub.1 ' and R.sub.4 represents A or A', and R.sub.1, R.sub.1 ', A and A' have the meanings given for formulae I and II, into contact with a microorganism that is capable of 13.beta.-hydroxylation or 14,15-epoxidation or of both reactions, or into contact with active constituents thereof. The microorganism or its active constituents may be either in free form or immobilized form.

Microbial process for the preparation of milbemycin derivatives

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.

The present invention relates to novel compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, a silyl group or an acyl group,

Pesticides

Novel compounds of formula I ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3, R.sup.7, R.sup.8 and R.sup.9, independently of the others, is H or halogen,

3-aminobenzoylphenylureas useful for controlling parasites and insects

Derivatives of milbemycins D, A.sub.3 and A.sub.4 and of the corresponding sec-butyl compound have a halogen atom at the 13-position; at the 5-position, they have an oxygen (keto) atom, an oxime group or a substituted oxime group. They may be prepared from known compounds by any appropriate combination of halogenation, ketonization and oximation.

13-Halomilbemycin derivatives, their preparation and compositions

The present invention relates to novel 5-oximino-13.beta.-carbonylthiomilbemycin derivatives of formula I, to their preparation and to the use thereof for controlling pests. The invention further relates to pesticidal compositions which contain at least one of these compounds as active ingredient. The novel compounds have the general formula I ##STR1## wherein R.sub.1 is hydrogen or an alkyl, cycloalkyl or acyl group,

Insecticides and parasiticides

Novel compounds of the formula ##STR1## in which R.sub.1 is a hydrogen or a silyl or acyl group, R.sub.2 is methyl, ethyl, isopropyl or sec.-butyl and R is hydrogen, unsubstituted or substituted, linear or branched-chain C.sub.1 -C.sub.18 -alkyl groups, unsubstituted or substituted cycloaliphatic groups having 3 to 10 carbon atoms, unsubstituted or substituted C.sub.2 -C.sub.6 -alkenyl groups, unsubstituted or substituted C.sub.2 -C.sub.6 -alkynyl groups, unsubstituted or substituted phenyl groups or unsubstituted or substituted benzyl groups. The active compounds possess advantageous pesticidal properties. They are particularly suitable for the control of pests in agriculture and the management of stored products.

The invention relates to parasiticidally and insecticidally highly active compounds of formula I ##STR1## wherein R is C.sub.1 -C.sub.10 alkyl;

13.beta.-alkylmilbemycin derivatives for controlling parasites of

The invention relates to parasiticidally and insecticidally highly active compounds of formula I ##STR1## wherein R.sub.1 is hydrogen or a protecting group;

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Liestal, Switzerland

Bruno Frei