1461138263-dad7cd44-f7b5-442c-b2d7-6961178a55de

1. A process for producing a cyclopropanecarboxylate of formula (1):
which process comprises reacting cyclopropanecarboxylic acid of formula (2):
with a monohydroxy compound of formula (3):
R6OH\u2003\u2003(3),

in the presence of
a zirconium compound,

wherein R1, R2, R3, R4, and R5 independently represent
a hydrogen atom,
an alkyl group which may be substituted,
an alkenyl group which may be substituted,
an alkynyl group which may be substituted, or
an aryl group which may be substituted; and
R6 represents
an alkyl group which may be substituted, or
an aryl group which may be substituted.
2. A process according to claim 1, wherein
R1, R2, R3, R4, and R5 independently represent
a hydrogen atom,
an alkyl group,
an alkenyl group,
an alkynyl group, or
an aryl group, and
wherein the alkyl, alkenyl, and alkynyl groups may be independently substituted with at least one member selected from
a halogen atom, an alkoxy group,
an alkoxy-carbonyl group,
a haloalkoxy-carbonyl group,
an aryl group,
a halocycloalkylidene group,
an alkoxyimino group,
an alkylsulfonyl group,
an alkylsulfonyloxy group, and
a hydroxysulfinyl group; and
R6 represents
an alkyl group, which may be substituted with a member selected from
a halogen atom, a cyano group, a nitro group,
an alkenyl group, a haloalkenyl group,
an alkynyl group,
an aryl or heterocyclic group which may be substituted with at lest one member selected from:
an alkyl group, a haloalkyl group,
an alkoxy group, a haloalkoxy group,
an alkoxyalkyl group,
an alkenyl group, an alkynyl group,
an aryl group, an aryoxy group,
a haloaryloxy group,
an aralkyl group,
an acyl group,
a haloacyloxyalkyl group,
an amino group, and a halogen atom; or

R6 represents:
a 1-, or 2-indanyl group which may be substituted with an alkynyl group or an aryl or heteraryl group;
a cycloalkenyl group substituted with at least one member selected from an oxo group, an alkyl group, an alkenyl and an alkynyl group; or
an aryl group which may be substituted with a phenyl, an alkynyl group, an acyl group, halogen atom, an alkoxy group, or an alkyl group.
3. A process according to claim 2, wherein
R1, R2, R3, R4, and R5independently represent
a hydrogen atom,
an (C1-C10) alkyl group,
an (C2-C5) alkenyl group,
an (C2-C5) alkynyl group, or
an (C6-C14) aryl group, and
wherein the alkyl, alkenyl, and alkynyl groups may be independently substituted with at least one member selected from
a halogen atom, an (C1-C4) alkoxy group,
an (C1-C4) alkoxy-carbonyl group,
a halo (C1-C4) alkoxy-carbonyl group,
an (C6-C14) aryl group,
a halo (C3-C5) cycloalkylidene group,
an (C1-C3) alkoxyimino group,
an (C1-C4) alkylsulfonyl group,
an (C1-C4) alkylsulfonyloxy group, and
a hydroxysulfinyl group; and
R6 represents
an (C1-C10) alkyl group, which may be substituted with a member selected from
a halogen atom, a cyano group, a nitro group,
an (C2-C5) alkynyl group, a halo (C2-C5) alkenyl group,
an (C2-C5) alkynyl group,
an (C6-C14) aryl or heterocyclic group which may be substituted with at lest one member selected from:
an (C1-C14) alkyl group, a halo (C1-C14) alkyl group,
an (C1-C4) alkoxy group, a halo (C1-C4) alkoxy group,
an (C1-C4) alkoxy (C1-C14) alkyl group,
an (C2-C5) alkenyl group, an (C2-C5) alkynyl group,
an (C6-C14) aryl group, an (C6-C14) aryoxy group,
a halo (C6-C14) aryloxy group,
an (C7-C8) aralkyl group,
an (C1-C2) acyl group,
a haloacyloxy (C1-C14) alkyl group,
an amino group, and a halogen atom; or

in the presence of
a catalyst compound comprising an element of Group 4 of the Periodic Table of Elements,
wherein either R1 or R2 represents 2,2-dichlorovinyl or 2-methyl-1-propenyl group, and the other group represents a hydrogen atom,
R3 and R4 represent a methyl group,
R5 represents a hydrogen atom, and
R6 represents
an alkyl group which may be substituted, or
an aryl group which may be substituted.
7. A process according to claim 6, wherein
R6 represents
an alkyl group, which may be substituted with a member selected from
a halogen atom, a cyano group, a nitro group,
an alkenyl group, a haloalkenyl group,
an alkynyl group,
an aryl or heterocyclic group which may be substituted with at least one member selected from:
an alkyl group, a haloalkyl group,
an alkoxy group, a haloalkoxy group,
an alkoxyalkyl group,
an alkenyl group, an alkynyl group,
an aryl group, an aryoxy group,
a haloaryloxy group,
an aralkyl group,
an acyl group,
a haloacyloxyalkyl group,
an amino group, and a halogen atom; or

R6 represents:
a 1-, or 2-indanyl group which may be substituted with an (C2-C5)alkynyl group or an (C6-C14)aryl or 5-membered heteroaryl group;
a cycloalkenyl group substituted with at least one member selected from an oxo group, an (C1-C14)alkyl group, an (C2-C5)alkenyl and an (C2-C5)alkynyl group; or
an (C6-C14)aryl group which may be substituted with a phenyl, an (C2-C5)alkynyl group, a (C1-C2)acyl group, a halogen atom, a (C1-C4)alkoxy group, or a (C1-C14)alkyl group.
9. A process according to claim 6, 7 or 8, wherein the catalyst compound is a zirconium, hafnium or titanium compound.
10. A process according to claim 9, wherein the catalyst compound is a zirconium, hafnium or titanium compound having Lewis acidity.
11. A process according to claim 9, wherein the catalyst compound is a compound represented by formula (4):
M(O)m(X)n(Y)4-2m-n\u2003\u2003(4)
wherein M represents an element of Group 4 of the Periodic Table of Elements; X and Y independently represent a halogen atom, an alkoxy group, an acetylacetonate group, an acyloxy group, an amino group which may be substituted with up to two alkyl groups, or a cyclopentadienyl group; and m is equal to 0 or 1, and n is equal to 0, 1, or 2.
12. A process according to claim 11, wherein M represents zirconium.
13. A process according to claim 11, wherein M represents hafnium or titanium.
14. A process according to claim 12, wherein the zirconium compound is zirconium tetrachloride, a zirconocene compound, or zirconium alkoxide.
15. A process according to claim 13, wherein the hafnium or titanium compound is hafnium or titanium halide, a hafnium or titanium alkoxide, or an amide compound of hafnium or titanium.
16. A process according to claim 6, wherein the monohydroxy compound of formula (3) is a primary alcohol.
17. A process according to claim 7, wherein the monohydroxy compound is a compound of formula (3), wherein R6 represents a methyl or ethyl group substituted with at least one member selected from the aryl group which may be substituted, a cyano group, and the alkynyl group.
18. A process according to claim 7, wherein the monohydroxy compound of formula (3) is 3-phenoxybenzyl alcohol.
19. A process according to claim 8, wherein the monohydroxy compound of formula (3) is 4 -hydroxy-3-methyl-2-(2-propenyl)-2-cyclopentene-1-one.
20. A process according to claim 8, wherein the monohydroxy compound of formula (3) is 4-hydroxy-3methyl-2-(2-propynyl)-2-cyclopentene-1-one.
21. A process for producing a cyclopropanecarboxylate of formula (1):
which process comprises reacting cyclopropanecarboxylic acid of formula (2):
with a monohydroxy compound of formula (3):
R6OH\u2003\u2003(3)

in the presence of
a catalyst compound comprising an element of Group 4 of the Periodic Table of Elements,

wherein R1, R2, R3, R4, and R5 independently represent
a hydrogen atom, a halogen atom,
an alkyl group which may be substituted,
an alkenyl group which may be substituted,
an alkynyl group which may be substituted, or
an aryl group which may be substituted; and
R6 represents
3-methyl-2-(2-propenyl)-2-cyclopentene-1-one-4-yl group, or 3-methyl-2-(2-propeynyl)-2-cyclopentene-1-one-4-yl group.
22. A process according to claim 21, wherein
R1, R2, R3, R4, and R5 independently represent
a hydrogen atom, a halogen atom,
an alkyl group,
an alkenyl group,
an alkynyl group, or
an aryl group, and
wherein the alkyl, alkenyl, and alkynyl groups may be independently substituted with at least one member selected from
a halogen atom, an alkoxy group,
an alkoxy-carbonyl group,
a haloalkoxy-carbonyl group,
an aryl group,
a halocycloalkylidene group,
an alkoxyimino group,
an alkylsulfonyl group,
an alkylsulfonyloxy group, and
a hydroxysulfinyl group.
23. A process according to claim 22, wherein
R1, R2, R3, R4, and R5 independently represent
a hydrogen atom, a halogen atom,
an (C1-C10)alkyl group,
an (C2-C5)alkenyl group,
an (C2-C5)alkynyl group, or
an (C6-C14)aryl group, and
wherein the alkyl, alkenyl, and alkynyl groups may be independently substituted with at least one member selected from
a halogen atom, an (C1-C4)alkoxy group,
an (C1-C4)alkoxy-carbonyl group,
a halo (C1-C4)alkoxy-carbonyl group,
an (C6-C14)aryl group,
a halo(C3-C5)cycloalkylidene group,
an (C1-C3)alkoxyimino group,
an (C1-C4)alkylsulfonyl group,
an (C1-C4)alkylsulfonyloxy group, and
a hydroxysulfinyl group.
24. A process according to claim 22, or 23, wherein the catalyst compound is a zirconium, hafnium or titanium compound.
25. A process according to claim 24, wherein the catalyst compound is a zirconium, hafnium or titanium compound having Lewis acidity.
26. A process according to claim 24, wherein the catalyst compound is a compound represented by formula (4):
M(O)m(X)n(Y)4-2m-n\u2003\u2003(4)
wherein M represents an element of Group 4 of the Periodic Table of Elements; X and Y independently represent a halogen atom, an alkoxy group, an acetylacetonate group, an acyloxy group, an amino group which may be substituted with up to two alkyl groups, or a cyclopentadienyl group; and m is equal to 0 or 1, and n is equal to 0, 1, or 2.
27. A process according to claim 26, wherein M represents zirconium.
28. A process according to claim 26, wherein M represents hafnium or titanium.
29. A process according to claim 27, wherein the zirconium compound is zirconium tetrachloride, a zirconocene compound, or zirconium alkoxide.
30. A process according to claim 28, wherein the hafnium or titanium compound is hafnium or titanium halide, a hafnium or titanium alkoxide, or an amide compound of hafnium or titanium.
31. A process for producing a 2,2-dimethyl-3-(1-propenyl)cyclopropanecarboxylate, which process comprises:
reacting a 2,2-dimethyl-3-(1-propenyl)cyclopropanecarboxylic acid with a monohydroxy compound of formula (3):
R6OH\u2003\u2003(3),
in the presence of
a zirconium compound,

wherein R6 represents
an alkyl group which may be substituted, or
an aryl group which may be substituted.

The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.

1. A method for increasing seed yield in a plant, said method comprising increasing the level andor activity of a cytokinin oxidase (CKX) in the embryo andor aleurone of a plant seed, wherein said embryo andor aleurone have increased levels andor activity of cytokinin oxidase relative to other parts of said seed.
2. The method according to claim 1, wherein said increased expression in the embryo andor aleurone is effected by introducing a genetic modification.
3. The method according to claim 2, wherein said genetic modification is effected by one of: T-DNA activation, TILLING, site-directed mutagenesis or directed evolution.
4. A method for increasing seed yield in a plant, said method comprising introducing into a plant cell a genetic construct comprising an isolated nucleic acid molecule encoding a cytokinin oxidase wherein said isolated nucleic acid molecule is operably linked to a promoter capable of driving expression in the embryo andor aleurone of a seed.
5. A method for producing a plant having increased seed yield and increased expression of a cytokinin oxidase in the embryo andor aleurone of a seed, said method comprising introducing into a plant cell a genetic construct comprising an isolated nucleic acid molecule encoding a cytokinin oxidase wherein said isolated nucleic acid molecule is operably linked to a promoter capable of driving expression in the embryo andor aleurone of a seed.
6. A method for producing a plant having increased seed yield and increased expression of a cytokinin oxidase in the embryo andor aleurone of a seed, said method comprising:
(a) introducing into a plant cell a genetic construct comprising an isolated nucleic acid molecule encoding a cytokinin oxidase, wherein said isolated nucleic acid molecule is operably linked to a promoter capable of driving expression in the embryo andor aleurone of a seed;
(b) regenerating a plant therefrom;
(c) growing the regenerated plant to seed set; and
(d) selecting a plant with increased seed yield compared to a corresponding wild type plant.
7. The method of any of claim 4 wherein the promoter capable of driving expression in the embryo andor aleurone comprises nucleotides 1-1256 of SEQ ID NO: 41.
8. The method of claim 2 wherein the nucleic acid molecule encoding a cytokinin oxidase is selected from the group consisting of:
(a) nucleic acids comprising a DNA sequence as given in any of SEQ ID NOs: 42, 37, 27, 1, 3, 5, 7, 9, 11, 25, 26, 28 to 30, 33 or 34, or the complement thereof,
(b) nucleic acids comprising the RNA sequences corresponding to any of SEQ ID NOs: 42, 37, 27, 1, 3, 5, 7, 9, 11, 25, 26, 28 to 30, 33 or 34, or the complement thereof,
(c) nucleic acids specifically hybridizing to the complement of any of SEQ ID NOs: 42, 37, 27, 1, 3, 5, 7, 9, 11, 25, 26, 28 to 30, 33 or 34,
(d) nucleic acids encoding a protein comprising the amino acid sequence as given in any of SEQ ID NOs: 2, 4, 6, 8, 10, 12, 35, 36 or 38, or the complement thereof,
(e) nucleic acids as defined in any of (a) to (d) characterized in that said nucleic acid is DNA, genomic DNA, cDNA, synthetic DNA or RNA wherein T is replaced by U,
(f) nucleic acid which is degenerate compared to a nucleic acid as given in any of SEQ ID NOs: 42, 37, 27, 1, 3, 5, 7, 9, 11, 25, 26, 28 to 30, 33 or 34, or which is degenerate compared to a nucleic acid as defined in any of (a) to (e) as a result of the genetic code,
(g) nucleic acids which are divergent from a nucleic acid encoding a protein as given in any of SEQ ID NOs: 2, 4, 6, 8, 10, 12, 35, 36 or 38, or which is divergent from a nucleic acid as defined in any of (a) to (e), due to the differences in codon usage between the organisms,
(h) nucleic acids encoding a protein as given in SEQ ID NOs: 2, 4, 6, 8, 10, 12, 35, 36 or 38, or nucleic acids as defined in (a) to (e) which are divergent due to the differences between alleles,
(i) nucleic acids encoding a protein as given in any of SEQ ID NOs: 2, 4, 6, 8, 10, 12, 35, 36 or 38,
(j) functional fragments of nucleic acids as defined in any of (a) to (i) having the biological activity of a cytokinin oxidase, and
(k) nucleic acids encoding a plant cytokinin oxidase, comprising the consensus sequence hTDYLhholGGTLSssG and cLFxushGsLGQFGIIstA or comprising expression in seeds of a nucleic acid encoding a protein that reduces the level of active cytokinins in plants or plant parts.
9. The method of claim 4, wherein the isolated nucleic acid molecule operably linked to a promoter capable of driving expression in the embryo andor aleurone comprises the nucleotide sequence as set forth in SEQ ID NO: 41.
10. The method of claim 1 wherein the increase in seed yield comprises at least one of: total weight of seeds, total number of seeds, total number of filled seeds, harvest index, and thousand kernel weight.
11. An isolated nucleic acid molecule encoding a cytokinin oxidase operably linked to a promoter capable of driving overexpression of said nucleic acid molecule in the embryo andor aleurone of a seed relative to other parts of said seed.
12. The isolated nucleic acid molecule of claim 11 wherein the nucleic acid molecule encoding a cytokinin oxidase is selected from the group consisting of:
(a) nucleic acids comprising a DNA sequence as given in any of SEQ ID NOs: 42, 37, 27, 1, 3, 5, 7, 9, 11, 25, 26, 28 to 30, 33 or 34, or the complement thereof,
(b) nucleic acids comprising the RNA sequences corresponding to any of SEQ ID NOs: 42, 37, 27, 1, 3, 5, 7, 9, 11, 25, 26, 28 to 30, 33 or 34, or the complement thereof,
(c) nucleic acids specifically hybridizing to the complement of any of SEQ ID NOs: 42, 37, 27, 1, 3, 5, 7, 9, 11, 25, 26, 28 to 30, 33 or 34,
(d) nucleic acids encoding a protein comprising the amino acid sequence as given in any of SEQ ID NOs: 2, 4, 6, 8, 10, 12, 35, 36 or 38, or the complement thereof,
(e) nucleic acids as defined in any of (a) to (d) characterized in that said nucleic acid is DNA, genomic DNA, cDNA, synthetic DNA or RNA wherein T is replaced by U,
(f) nucleic acid which is degenerate compared to a nucleic acid as given in any of SEQ ID NOs: 42, 37, 27, 1, 3, 5, 7, 9, 11, 25, 26, 28 to 30, 33 or 34, or which is degenerate compared to a nucleic acid as defined in any of (a) to (e) as a result of the genetic code,
(g) nucleic acids which are divergent from a nucleic acid encoding a protein as given in any of SEQ ID NOs: 2, 4, 6, 8, 10, 12, 35, 36 or 38, or which is divergent from a nucleic acid as defined in any of (a) to (e), due to the differences in codon usage,
(h) nucleic acids encoding a protein as given in SEQ ID NOs: 2, 4, 6, 8, 10, 12, 35, 36 or 38 or nucleic acids as defined in (a) to (e) which are divergent due to the differences between alleles,
(i) nucleic acids encoding a protein as given in any of SEQ ID NOs: 2, 4, 6, 8, 10, 12, 35, 36 or 38,
(j) functional fragments of nucleic acids as defined in any of (a) to (i) having the biological activity of a cytokinin oxidase, and
(k) nucleic acids encoding a plant cytokinin oxidase, comprising the consensus sequence hTDYLhholGGTLSssG and cLFxushGsLGQFGIIstA or comprising expression, preferably in seeds, of a nucleic acid encoding a protein that reduces the level of active cytokinins in plants or plant parts.
13. A vector comprising the isolated nucleic acid molecule of claim 11.
14. A vector comprising the isolated nucleic acid molecule having the sequence set forth in SEQ ID NO: 41.
15. A host cell comprising the isolated nucleic acid molecule of claim 11.
16. A host cell comprising a vector of claims 13.
17. The host cell of claim 16, which is a bacterial, fungal, or plant cell.
18. Plant having increased seed yield, comprising a genetic modification, which genetic modification results in increased expression of cytokinin oxidase in the aleurone andor embryo of a seed, relative to other parts of said seed.
19. A transgenic plant, plant part, or plant tissue comprising plant cells of claim 17.
20. The transgenic plant of claim 19 which is a dicotyledonous or monocotyledonous plant.
21. Transgenic plant according to claim 20, wherein said monocotyledonous plant is selected from a group consisting of sugarcane, rice, maize, wheat, barley, millet, rye, oats, and sorghum.
22. A transgenic harvestable part, or a product directly derived from a transgenic harvestable part of the transgenic plant of claim 19.
23. A transgenic harvestable part of the transgenic plant of claim 22 selected from the group consisting of seeds, leaves, fruits, stem cultures, rhizomes, roots, tubers and bulbs.
24. Transgenic progeny of the plant or plant part of claim 19.
25. Harvestable parts of the plant according to claim 18, or products directly derived from said harvestable parts.
26-29. (canceled)
30. A method for increasing seed yield in a plant, said method comprises introducing into a plant cell the vector according to claim 13.
31. The method according to claim 1, wherein said increased expression in the embryo andor aleurone is effected by introducing a genetic modification in the locus of the cytokinin oxidase-encoding gene.