Spinosyn-producing polyketide synthases
View Patent ↗The invention provides, biologically active spinosyns, hybrid spinosyn polyketide synthases capable of functioning in Saccharopolyspora spinosa to produce the spinosyns, and methods of controlling insects using the spinosyns.
1. A compound of the formula (I)
wherein
R1 is hydrogen, methyl, or ethyl;
R2 is hydrogen, methyl, or ethyl;
R3 is hydrogen,
R4 is methyl or ethyl, either of which may be substituted with one or more groups selected from halo, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, or cyano; or
R4 is an alpha-branched C 3 -C 5 alkyl group, C 3 -C 8 cycloalkyl group, or C 3 -C 8 cycloalkenyl group, any of which may be substituted with one or more groups selected from halo, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, or cyano; or
R4 is a 3-6 membered heterocyclic group that contains O or S, that is saturated or fully or partially unsaturated, and that may be substituted with one or more groups selected from halo, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, or cyano;
R5 is hydrogen or methyl;
R6 is hydrogen or methyl;
R7 is hydrogen or methyl;
R8 is hydrogen, methyl, or ethyl; and
R9 is hydrogen, methyl, or ethyl,
and/or
a 5,6-dihydro derivative of the compound of formula (I), provided that the compound of formula (I) has at least one of the following features:
a) R4 is n-propyl, iso-propyl, cyclopropyl, methylcyclopropyl, sec-butyl, cyclobutyl, methylthio, or furyl, or
b) R1 or R2 is ethyl.
2. The compound of claim 1 , wherein R1 is ethyl.
3. The compound of claim 1 , wherein R2 is ethyl.
4. The compound of claim 1 , wherein R4 is n-propyl, iso-propyl, cyclopropyl, methylcyclopropyl, sec-butyl, cyclobutyl, methylthio, or furyl.
5. A compound selected from the group consisting of:
21-desethyl-21-cyclopropyl spinosyn A;
21-desethyl-21-cyclopropyl spinosyn D;
21-desethyl-21-cyclobutyl spinosyn A;
21-desethyl-21-cyclobutyl spinosyn D;
21-desethyl-21-methylthiomethyl spinosyn A;
21-desethyl-21-methylthiomethyl spinosyn D;
21-desethyl-21-cyanomethyl spinosyn A;
5,6-dihydro-21-desethyl-21-cyclobutyl spinosyn A;
21-desethyl-21-isopropyl spinosyn A;
21-desethyl-21-isopropyl spinosyn D;
21-desethyl-21-sec-butyl spinosyn A;
21-desethyl-21-sec-butyl spinosyn D;
21-desethyl-21-methylcyclopropyl spinosyn A;
21-desethyl-21-methylcyclopropyl spinosyn D;
21-desethyl-21-(3-furyl) spinosyn A;
21-desethyl-21-(3-furyl) spinosyn D;
21-desethyl-21-cyclopropyl spinosyn A 17-pseudoaglycone;
21-desethyl-21-cyclopropyl spinosyn D 17-pseudoaglycone;
21-desethyl-21-cyclobutyl spinosyn A 17-pseudoaglycone;
21-desethyl-21-cyclobutyl spinosyn D 17-pseudoaglycone;
16-desmethyl spinosyn D;
16-desmethyl spinosyn D 17-pseudoaglycone;
21-desethyl-21-n-propyl spinosyn A;
6-ethyl spinosyn A;
6-ethyl-21-desethyl-21-n-propyl spinosyn A;
16-desmethyl-16-ethyl spinosyn A;
16-desmethyl-16-ethyl spinosyn D; and
21-desethyl-21-n-propyl spinosyn D.
6. A pesticide composition comprising an effective amount of the compound of claim 1 as active ingredient in combination with an appropriate diluent or carrier.
7. The pesticide composition of claim 6 , wherein R1 is ethyl.
8. The pesticide composition of claim 6 , wherein R2 is ethyl.
9. The pesticide composition of claim 6 , wherein R4 is n-propyl, iso-propyl, cyclopropyl, methylcyclopropyl, sec-butyl, cyclobutyl, methylthio, or furyl.
10. A pesticide composition comprising an effective amount of the compound of claim 5 as active ingredient in combination with an appropriate diluent or carrier.