Reduced avermectin derivatives
First Claim
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1. A compound having the formula:
- ##STR6## wherein A is a single bond, B and C each represent a double bond, and D represents a single bond or a double bond;
R1 is hydrogen, hydroxy or a ketone provided that R1 is present only when D indicates a single bond;
R2 is methyl, ethyl, iso-propyl or sec-butyl or --C(CH3)=CHR10 where R10 is methyl, ethyl or isopropyl;
R3 is hydroxy, loweralkoxy, lower-alkanoyloxy or otherwise protected hydroxy or R3, together with the adjacent carbon atom and the hydrogen attached thereto, form a carbonyl group;
R4 is hydrogen, hydroxy, halogen, loweralkoxy, loweralkanoyloxy, ##STR7## R5 is hydroxy, or --NR6 R7 or R5, together with the adjacent carbon atom and the hydrogen attached thereto, form a carbonyl group;
R6 and R7 are independently hydrogen, loweralkyl, or lowerlkanoyl;
R8 is hydrogen or bromo;
R9 is hydrogen, halogen, hydroxy, or R9 together with the adjacent carbon atom and the hydrogen attached thereto, form a carbonyl group; and
the 4" and 5 position trisubstituted silyl protected hydroxy derivatives thereof.
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Abstract
There are disclosed novel avermectin reduction products. The compounds are prepared by selective catalytic hydrogenation of avermectin-like compounds or by reaction of selected double bonds with electrophylic reagents. The reduced avermectin 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. The reduced avermectin compounds have increased stability towards light which prolongs their insecticidal activities when applied to field crops subject to irradiation by sunlight.
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11 Claims
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1. A compound having the formula:
- ##STR6## wherein A is a single bond, B and C each represent a double bond, and D represents a single bond or a double bond;
R1 is hydrogen, hydroxy or a ketone provided that R1 is present only when D indicates a single bond; R2 is methyl, ethyl, iso-propyl or sec-butyl or --C(CH3)=CHR10 where R10 is methyl, ethyl or isopropyl; R3 is hydroxy, loweralkoxy, lower-alkanoyloxy or otherwise protected hydroxy or R3, together with the adjacent carbon atom and the hydrogen attached thereto, form a carbonyl group; R4 is hydrogen, hydroxy, halogen, loweralkoxy, loweralkanoyloxy, ##STR7## R5 is hydroxy, or --NR6 R7 or R5, together with the adjacent carbon atom and the hydrogen attached thereto, form a carbonyl group; R6 and R7 are independently hydrogen, loweralkyl, or lowerlkanoyl; R8 is hydrogen or bromo; R9 is hydrogen, halogen, hydroxy, or R9 together with the adjacent carbon atom and the hydrogen attached thereto, form a carbonyl group; and
the 4" and 5 position trisubstituted silyl protected hydroxy derivatives thereof. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)
- ##STR6## wherein A is a single bond, B and C each represent a double bond, and D represents a single bond or a double bond;
Specification