Abstract: Novel substituted and unsubstituted 13-(alkoxy)methoxy derivatives of the avermectin aglycones are useful as anthelmintic and antiparasitic agents. The compounds are also useful as pesticides and insecticides against agricultural pests. Included herein are novel intermediates useful in the process for preparing said avermectin aglycone derivatives. Compositions of said derivatives and methods of administering said compositions are also disclosed.

Abstract: There are disclosed novel avermectin and milbemycin compounds wherein the 13-position is oxidized to a keto function. The 13-keto derivatives are prepared from the 13-hydroxy compounds by oxidizing the 13-position with a suitable oxidizing agent. The avermectin and milbemycin 13-keto derivatives are active in their own right and also serve as intermediates in the preparation of 13-imino and 13-amino derivatives. The 13-keto, imino and amino compounds have utility as anti-parasitic agents and compositions for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests.

Abstract: The C-076 compounds are a series of four pairs of macrolides in which the members of each pair are homologous. The instant processes convert the C-076 A2 and B2 compounds isolated from a fermentation broth into the biologically preferred B1 and A1 compounds or into the dihydro derivatives thereof.

Abstract: There are disclosed novel avermectin and milbemycin compounds wherein the 8a position is oxidized to a ketone group. The 8a-oxo compounds are prepared by oxidizing an avermectin or milbemycin compound. The avermectin and milbemycin 8a-oxo compounds have utility as anti-parasitic agents and compositions for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests.

Abstract: There are disclosed novel avermectin compounds wherein certain double bonds are oxidized to epoxides. The epoxides are prepared by oxidizing an avermectin compound with a mild oxidizing agent. The avermectin epoxide compounds have utility as anti-parasitic agents and compositions for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests.

Abstract: There are disclosed novel avermectin and milbemycin compounds wherein the various hydroxy groups are substituted with a phosphate ester group. The phosphate esters are prepared by reacting an avermectin or milbemycin compound with one or more unprotected hydroxy groups with a disubstituted halo phosphate. The avermectin and milbemycin phosphate esters have increased water solubility when compared with the parent compounds. The phosphate ester compounds have utility as anti-parasitic agents and compositions for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests.

Abstract: There are disclosed novel avermectin compounds wherein the 4-methyl group is substituted with hydroxy or various groups connected through the hydroxy oxygen atom. The hydroxy compounds are prepared by oxidation of the 4-methyl group and the hydroxy substituents prepared by a substitution process selective for primary alcohols. The compounds have utility as antiparasitic agents and compositions for that use are also disclosed.

Abstract: There are disclosed novel avermectin compounds wherein the 4" hydroxy group is oxidized to a keto group or replaced with an amino or substituted amino group. The keto compounds are prepared by oxidation with reagents such as oxalyl chloride in dimethylsulfoxide. The amino compounds are prepared from the ketone using a reducing agent and an aminating agent. Substituted amino compounds are prepared from the thus produced unsubstituted amino compounds. The keto compounds and amino compounds have utility as anti-parasitic agents and compositions for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests. In addition the amino compounds have anti-bacterial activity which is not found in any of the precursors.

Abstract: There is disclosed a process for converting avermectin compounds (formerly identified as C-076 compounds) of the A-type, into avermectin compounds of the B-type. The process is carried out on the naturally occuring avermectin compounds as well as on derivatives thereof. The process involves selectively cleaving the 5-methoxy group, converting it into the hydroxy group, through the intermediate 5-keto group.

Abstract: The C-076 compounds are a series of four pairs of macrolides in which the members of each pair are homologous. The instant processes convert the C-076 A2 and B2 compounds isolated from a fermentation broth into the biologically preferred B1 and A1 compounds or into the dihydro derivatives thereof.

Abstract: Derivatives of C-076 compounds are described in which the C-076 molecule, a series of macrolides, has the 23-hydroxy group thereof oxidized to the 23-keto group. The 23-keto compounds are prepared by selectively oxidizing the suitably protected 23-hydroxy compound using such oxidizing agents as pyridinium dichromate, chromic acid-dimethyl pyrazole, chromic acid, chromic acid-acetic acid, and the like. Alternatively, selective oxidation of the unprotected 23-hydroxy compound may be accomplished by placing the compound in soil. Further reaction of the oxidized C-076 compounds is also possible. The compounds thus produced have profound anthelmintic, insecticidal, ectoparasiticidal, and acaricidal activity. Compositions containing the described C-076 derivatives as the active ingredient thereof are also disclosed.

Abstract: Derivatives of C-076 are described in which the C-076 molecule, a series of macrolides in which one of the substituents is a 4-(.alpha.-L-oleandrosyl)-.alpha.-L-oleandrose has one or both of the carbohydrate moieties removed therefrom. The compounds thus produced have profound anthelmintic, insecticidal, ectoparasiticidal and acaracidal activity and compositions for such use are also disclosed.

Abstract: Derivatives of C-076, a series of macrolides, are described in which the substituents are acyl groups. The acyl substituents may be aromatic of non-aromatic. The acyl derivatives are prepared by various procedures depending upon the particular C-076 compound being substituted. The compounds thus produced have profound anthelmintic, insecticidal, ectoparasiticidal and acaracidal activity and compositions for such uses are also disclosed.

Abstract: Derivatives of the C-076 compounds are disclosed wherein the 13-position is unsubstituted. The compounds are prepared by removing the glycosyl groups on the 13-position of the C-076 compounds isolated from the fermentation broth of Streptomyces avermitilis, followed by halogenation and subsequent removal of the halogen. The disclosed compounds are antiparasitic, anthelmintic, insecticidal and acaricidal agents.

Abstract: Derivatives of the C-076 compounds are disclosed wherein the 13-position is unsubstituted or substituted by a halogen atom. The compounds are prepared by removing the glycosyl groups on the 13-position of the C-076 compounds isolated from the fermentation broth of Streptomyces avermitilis. This is followed by substitution of the 13-hydroxy group with a halogen, and subsequent removal of the halogen. The disclosed compounds are antiparasitic, anthelmintic, insecticidal and acaracidal agents.

Abstract: Dihydroxybenzisoxazolin-3-yl-substituted-1-methyl-5-nitroimidazoles having the hydroxy- groups on adjacent 4,5-; 5,6- or 6,7-positions of the isoxazolin group. These compounds have antibacterial and antiprotozoal activity in humans and animals. They are particularly active against trypanosomiasis and trichomoniasis.

Abstract: Novel substituted benzoylacrylanilides are prepared by reacting a substituted benzoylacrylic acid with a substituted aniline in the presence of a coupling agent. These acrylanilides have significant anticoccidial activity.

Abstract: Novel substituted benzenedisulfonamides are disclosed which compounds are active anthelmintic agents being particularly useful against fascioliasis in sheep and cattle. Specifically the active compounds are 4-amino-1,3-benzenedisulfonamide with an unsaturated substituted alkyl group. Compositions and methods containing the novel substituted benzenedisulfonamides for use in anthelmintic therapy particularly against liver fluke are also disclosed.

Abstract: Derivatives of the C-076 compounds are disclosed wherein the 13-position is unsubstituted or substituted by a halogen atom. The compounds are prepared by removing the glycosyl groups on the 13-position of the C-076 compounds isolated from the fermentation broth of Streptomyces avermitilis. This is followed by substitution of the 13-hydroxy group with a halogen, and subsequent removal of the halogen. The disclosed compounds are antiparasitic, anthelmintic, insecticidal and acaracidal agents.

Abstract: Derivatives of the C-076 compounds are disclosed wherein the 13-position is unsubstituted. The compounds are prepared by removing the glycosyl groups on the 13-position of the C-076 compounds isolated from the fermentation broth of Streptomyces avermitilis, followed by halogenation and subsequent removal of the halogen. The disclosed compounds are antiparasitic, anthelmintic, insecticidal and acaricidal agents.