Germination promoters
The present invention relates to new compounds of formula (I) for the promotion of seed germination, to processes for preparing the compounds, to seeds comprising the compounds, to seed germination promoting compositions comprising the compounds and to methods of using the compounds for promoting the germination of seeds. In particular, the compounds are useful in promoting germination of corn under cold stress conditions.
1. A compound of formula (I)
wherein X is oxygen or N—R 1 ;
R 1 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 8 alkylcarbonyl, C 1 -C 8 alkoxycarbonyl, aryl, heteroaryl, heterocyclyl and benzyl each optionally substituted with one or more R 2 ;
each R 2 is independently selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, carboxylic acid, aminocarbonyl, C 1 -C 4 aminocarbonyl and C 3 -C 4 cycloalkyl;
W, Y and Z are each independently hydrogen, methyl, trifluoromethyl or fluorine; and
U is hydrogen or methyl; or salts thereof.
2. A compound according to claim 1 , wherein X is N—R 1 , and R 1 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 8 alkylcarbonyl, C 1 -C 8 alkoxycarbonyl and heteroaryl each optionally substituted with one or more R 2 .
3. A compound according to claim 1 , wherein R 1 is selected from the group consisting of hydrogen, methyl, acetyl, thiazoyl and C(O)OtBu.
4. A compound according to claim 1 , wherein W and Y are independently selected from the group consisting of trifluoromethyl, fluorine and methyl, and wherein Z is fluorine or hydrogen.
5. A compound according to claim 1 , wherein W and Y are CF 3 .
6. A compound according to claim 1 , wherein Z is H.
7. A compound according to claim 1 , wherein U is H.
8. A compound of formula (II-1):
9. A compound selected from a compound of formula (III-1):
a compound of formula (III-15):
10. The compound of claim 9 , wherein the compound is the compound of formula (III-15):
11. The compound of claim 9 , wherein the compound is the compound of formula (III-1):
12. A compound according to claim 3 , wherein W and Y are independently selected from the group consisting of trifluoromethyl, fluorine and methyl, and wherein Z is fluorine or hydrogen.
13. A compound according to claim 12 , wherein W and Y are CF 3 .
14. A compound according to claim 13 , wherein Z is H and R 1 is H.
15. A composition comprising a compound according to claim 1 , and an agriculturally acceptable formulation adjuvant.
16. A mixture comprising a compound as defined in claim 1 , and a further active ingredient.
17. A method for promoting seed germination of a plant, wherein the method comprises applying to the plant, plant part, plant propagation material or plant growing locus a compound according claim 1 .
18. A method for improving the tolerance of a plant to abiotic stress, wherein the method comprises applying to the plant, plant part, plant propagation material, or plant growing locus a compound according to claim 1 .
19. A method for regulating or improving the growth of a plant, wherein the method comprises applying to the plant, plant part, plant propagation material, or plant growing locus a compound according to claim 1 .
20. Plant propagation material comprising a compound according to claim 1 .