13-Halo and 13-deoxy C-076 compounds

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.

What is claimed is: 
     
       1. A compound having the formula: ##STR3## wherein the broken line indicates a single or a double bond; R is halogen or hydrogen; R 1  is hydroxy and is present only when said broken line indicates a single bond;   R 2  is .[.n-propyl.]. .Iadd.isopropyl .Iaddend.or sec-butyl; and   R 3  is methoxy or hydroxy.   
     
     
       2. The compound of claim 1 wherein R 2  is .[.n-propyl.]. .Iadd.isopropyl.Iaddend.. 
     
     
       3. The compound of claim 1 wherein R 2  is sec-butyl. 
     
     
       4. The compound of claim 3 wherein R is hydrogen. 
     
     
       5. The compound of claim 4 wherein R is hydrogen; R 1  is a 22,23 double bond; R 2  is sec-butyl; and R 3  is methoxy, which is 13-deoxy C-076 A1a-aglycone. 
     
     
       6. The compound of claim 4 wherein R is hydrogen; R 1  is hydroxy; R 2  is sec-butyl; and R 3  is methoxy which is 13-deoxy C-076 A2a-aglycone. 
     
     
       7. The compound of claim 4 wherein R is hydrogen; R 1  is a 22,23 double bond; R 2  is sec-butyl; and R 3  is hydroxy, which is 13-deoxy C-076 B1a-aglycone. 
     
     
       8. The compound of claim 4 wherein R is hydrogen; R 1  is hydroxy; R 2  is sec-butyl; and R 3  is hydroxy, which is 13-deoxy C-076 B2a-aglycone. 
     
     
       9. The compound of claim 3 wherein R is chlorine. 
     
     
       10. The compound of claim 9 wherein R is chlorine. R 1  is a 22,23-double bond; R 2  is sec-butyl; and R 3  is methoxy, which is 13-chloro-13-deoxy-C-076 A1a-aglycone. 
     
     
       11. The compound of claim 9 wherein R is chlorine; R 1  is hydroxy; R 2  is sec-butyl; and R 3  is methoxy, which is 13-chloro-13-deoxy-C-076-A2a-aglycone. 
     
     
       12. The compound of claim 9 wherein R is chlorine; R 1  is a 22,23 double bond; R 2  is sec-butyl; and R 3  is hydroxy, which is 13-chloro-13-deoxy-C-076-B1a-aglycone. 
     
     
       13. The compound of claim 9 wherein R is chlorine; R 1  is hydroxy; R 2  is sec-butyl; and R 3  is hydroxy, which is 13-chloro-13-deoxy-C-076-B2a-aglycone.