Thiazolo[5,4-d] pyrimidines and their use as agrochemicals
The present disclosure relates to thiazolo[5,4-d]pyrimidines and their use as agrochemicals and animal health products. In some embodiments, the disclosure relates to compounds of the formula (I-A) and of the formula (I-B):
1. A compound of Formula (I-A):
wherein:
R is H, lower alkyl, phenyl, pyridine N-oxide, or a heterocycle comprising a 5 or 6 membered single ring, wherein the lower alkyl, phenyl, pyridine N-oxide, or 5 or 6 membered single ring heterocycle are optionally substituted with halo, lower alkyl, lower alkoxy, benzyloxy, lower alkenyl, lower alkynyl, haloalkyl, haloalkoxy, NO 2 , CN, lower alkoxycarbonyl, lower alkanoyl, lower alkyl-SO q , and aldoximes and lower alkyloximes optionally substituted on oxygen by lower alkyl;
Z is a single bond between the phenyl ring and a carbon atom of R, CH 2 , NH, O, S, CH 2 O, OCH 2 , CH 2 CH 2 , or OCH 2 CH 2 ;
m is 4;
p is 0 or 1;
q is an integer from 0 to 2;
R 1 is independently H, halo, lower alkyl, lower alkenyl, lower alkynyl, hydroxy, lower alkoxy, haloalkyl, haloalkoxy, NO 2 , CN, lower alkanoyl, lower alkoxycarbonyl, mercapto, lower alkylthio, aldoximes and lower alkyloximes optionally substituted on oxygen by lower alkyl;
Y is a single bond, C((R 5 ) n )O or C((R 5 ) n );
n is 2;
R 2 are independently H or lower alkyl;
R 4 is H, halogen, lower alkyl, lower alkoxy or lower haloalkyl;
R 5 are independently H or lower alkyl; and
X is NR 3 , or O, where R 3 is selected from H, lower alkyl, lower alkanoyl, lower alkoxycarbonyl, hydroxy, lower alkoxy, lower alkyl-SO q , phenyl-SO q or substituted phenyl-SO q .
2. The compound of claim 1 , wherein R 3 and R 4 are H and X is NR 3 .
3. The compound of claim 2 , wherein Y is C((R 5 ) n ).
4. The compound of claim 3 , wherein R 1 is H, lower alkyl, lower alkoxy, or halo.
5. The compound of claim 4 , wherein Z is O and p is 1.
6. The compound of claim 5 , wherein R is an N containing 5 or 6 membered single ring optionally substituted with halo, lower alkyl, and haloalkyl.
7. The compound of claim 2 , wherein Y is a single bond, Z is O and p is 1.
8. The compound of claim 7 , wherein R 1 is H, lower alkyl, lower alkoxy, or halo.
9. The compound of claim 7 , wherein R is an N containing 5 or 6 membered single ring optionally substituted with halo, lower alkyl, and haloalkyl.
10. The compound of claim 2 , wherein Y is a C((R 5 ) n )O.
11. The compound of claim 10 , wherein R 1 is H, lower alkyl, lower alkoxy, or halo.
12. The compound of claim 11 , wherein Z is O and p is 1.
13. The compound of claim 12 , wherein R is an N containing 5 or 6 membered single ring optionally substituted with halo, lower alkyl, and haloalkyl.
14. A process of controlling insects, parasites, and/or fungi, said process comprising applying a compound according to claim 1 to an area where control of insects, parasites, and/or fungi is desired.
15. A composition comprising a mixture of a compound according to claim 1 with at least one other pesticide.
16. A composition comprising a compound according to claim 1 and at least one of antimicrobials, bactericides, defoliants, safeners, synergists, algaecides, attractants, desiccants, pheromones, repellants, avicides, disinfectants, semiochemicals, or molluscicides.
17. A compound of Formula (I-B):
wherein:
R is H, lower alkyl, phenyl, pyridine N-oxide, or a heterocycle comprising a 5 or 6 membered single ring, wherein the lower alkyl, phenyl, pyridine N-oxide, or 5 or 6 membered single ring heterocycle are optionally substituted with halo, lower alkyl, lower alkoxy, benzyloxy, lower alkenyl, lower alkynyl, haloalkyl, haloalkoxy, NO 2 , CN, lower alkoxycarbonyl, lower alkanoyl, lower alkyl-SO q , aldoximes and lower alkyloximes optionally substituted on oxygen by lower alkyl;
Z is H, a single bond between the phenyl ring and a carbon atom of R, CH 2 , NH, O, S, CH 2 O, OCH 2 , CH 2 CH 2 O, or OCH 2 CH 2 ;
m is 4;
p is 0 or 1;
q is an integer from 0 to 2;
R 1 is independently H, halo, lower alkyl, lower alkenyl, lower alkynyl, hydroxy, lower alkoxy, haloalkyl, haloalkoxy, NO 2 , CN, lower alkanoyl, lower alkoxycarbonyl, mercapto, lower alkylthio, aldoximes and lower alkyloximes optionally substituted on oxygen by lower alkyl;
Y is a single bond, C((R 5 ) n )O or C((R 5 ) n );
n is 2;
R 2 are independently H or lower alkyl;
R 4 is H, halogen, lower alkyl, lower alkoxy or lower haloalkyl;
R 5 are independently H or lower alkyl; and
X is NR 3 , O, and S, where R 3 is selected from H, lower alkyl, lower alkanoyl, lower alkoxycarbonyl, hydroxy, lower alkoxy, lower alkyl-SO q , phenyl-SO q or substituted phenyl-SO q .
18. The compound of claim 1 , wherein the compound is:
19. The compound of claim 1 , wherein Z is O and p is 1.
20. The compound of claim 19 , R is an N containing 5 or 6 membered single ring optionally substituted with halo, lower alkyl, and haloalkyl.