Fungicidal compositions
The instant invention describes tetrazole compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
1. A compound of Formula I, or salt, solvate, hydrate or prodrug thereof, wherein:
MBG is
R 1 is H, alkyl, haloalkyl, cycloalkyl, benzyl, or (heteroaryl)alkyl;
R 2 is halo, aryl, heteroaryl, aryloxy, alkoxy, haloalkoxy, heteoaryloxy, alkyl, cycloalkyl, cycloalkoxy, halocycloalkoxy, haloalkyl, (alkoxy)alkyl, (haloalkoxy)alkyl, (aryl)alkyl, (aryl)alkenyl, (aryl)alkynyl, or (heteroaryl)alkyl wherein each of the aryls and heteroaryls can independently be substituted with 1, 2 or 3 groups from R 4 ;
R 3 is aryl, heteroaryl, alkyl or cycloalkyl optionally substituted with 0, 1, 2 or 3 independent R 4 ; and
R 4 is independently halo, alkyl, haloalkyl, thioalkyl, thiohaloalkyl, NO 2 , CN, alkoxy, haloalkoxy, or thioamide ((C═S)NH 2 ).
2. A compound of claim 1 wherein R 1 is H, benzyl or alkyl.
3. A compound of claim 2 wherein R 1 is H.
4. A compound of claim 1 wherein R 2 is aryloxy, heteoaryloxy, alkyl, cycloalkyl, haloalkyl, (alkoxy)alkyl, (haloalkoxy)alkyl, alkoxy, haloalkoxy or halocycloalkoxy wherein each of the aryls and heteroaryls can independently be substituted with 1, 2 or 3 groups from R 4 .
5. A compound of claim 1 wherein R 3 is phenyl optionally substituted with 0, 1, 2 or 3 independent halo.
6. A compound of claim 5 wherein R 3 is 2,4-difluorophenyl or 2-fluoro-4-chlorophenyl.
7. A compound of claim 1 wherein R 4 is independently F, Cl, Br, CF 3 , OCF 3 , CN or thioamide ((C═S)NH 2 ).
8. A compound of claim 1 wherein:
R 1 is H, benzyl or alkyl;
R 2 is aryloxy, heteoaryloxy, alkyl, cycloalkyl, haloalkyl, (alkoxy)alkyl, (haloalkoxy)alkyl, alkoxy, haloalkoxy or halocycloalkoxy wherein each of the aryls and heteroaryls can independently be substituted with 1, 2 or 3 groups from R 4 ;
R 3 is phenyl optionally substituted with 0, 1, 2 or 3 independent halo; and
R 4 is independently F, Cl, Br, CF 3 , OCF 3 , CN or thioamide ((C═S)NH 2 ).
9. A composition comprising a compound of claim 1 and an agriculturally acceptable carrier.
10. A method of treating or preventing a fungal disease or disorder in or on a plant comprising contacting a compound of claim 1 with the plant or seeds.
11. A method of treating or preventing fungal growth in or on a plant comprising contacting a compound of claim 1 with the plant or seeds.
12. The composition according to claim 9 , further comprising an azole fungicide selected from epoxyconazole, tebuconazole, fluquinconazole, flutriafol, metconazole, myclobutanil, cycproconazole, prothioconazole and propiconazole.
13. The composition according to claim 9 , further comprising a strobilurin fungicide from the group trifloxystrobin, pyraclostrobin, orysastrobin, fluoxastrobin and azoxystrobin.
14. A compound of Formula II wherein:
R 5 is halo, aryl, heteroaryl, aryloxy, alkoxy, haloalkoxy, heteoaryloxy, alkyl, cycloalkyl, cycloalkoxy, halocycloalkoxy, haloalkyl, (alkoxy)alkyl, (haloalkoxy)alkyl, (aryl)alkyl, (aryl)alkenyl, (aryl)alkynyl, or (heteroaryl)alkyl wherein each of the aryls and heteroaryls can independently be substituted with 1, 2 or 3 groups from R 6 ; and
R 6 is independently halo, alkyl, haloalkyl, thioalkyl, thiohaloalkyl, NO 2 , CN, alkoxy, haloalkoxy, or thioamide ((C═S)NH 2 );
with the proviso that R 5 cannot be
15. The compound of claim 1 , that is one of the following compounds:
No.
Structure
F1
F2
F3
F4
F5
F6
F7
F8
F9
F10
F11
F12
F13
F14
or salt, solvate, hydrate or prodrug thereof.
16. The compound of claim 14 , that is one of the following compounds:
Compound No.
R
F15
F16
F17
F18
F19
F20
F21
or salt, solvate, hydrate or prodrug thereof.