Plant growth regulator compounds

Patent metadata

Field	Value
Publication number	US-11136292-B2
Application number	US-201716332673-A
Country	US
Kind code	B2
Filing date	Sep 5, 2017
Priority date	Sep 13, 2016
Publication date	Oct 5, 2021
Grant date	Oct 5, 2021

Abstract

The present invention relates to relates to novel strigolactone derivatives of formula (I), to processes for preparing these derivatives including intermediate compounds, to seeds comprising these derivatives, to plant growth regulator or seed germination promoting compositions comprising these derivatives and to methods of using these derivatives in controlling the growth of plants and/or promoting the germination of seeds.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
R 1 and R 2 are independently selected from the group consisting of hydrogen, C 1 -C 3 alkyl and C 1 -C 3 alkoxy;
X is O(R 3 );
R 3 is selected from the group consisting of hydrogen and C 1 -C 4 alkyl;
Y is O;
Z is selected from the group consisting of a bond, CH 2 , CH 2 -CH 2 , CH 2 (wherein the oxygen atom is bonded to the carbon positioned alpha to the A 1 substituent) and oxygen;
A 1 to A 4 are each independently selected from the group consisting of a bond, CR 8 , N, S and O, wherein A 1 to A 4 together with the atoms to which they are joined form a 5 to 6 membered aryl or heteroaryl; and
each R 8 is selected from the uroup consisting of hydrogen, halogen, methyl, ethyl, methoxy, ethoxy, fluoromethyl and trifluoromethyl; or two R 8 groups are joined via —OCH 2 O—to form a dioxolane ring;
or salts thereof.

2. A compound according to claim 1 , wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl and methoxy.

3. A compound according to claim 1 , wherein R 1 is methyl and R 2 is hydrogen or methyl.

4. A compound according to claim 3 , wherein R 2 is methyl.

5. A compound according to claim 1 , wherein R 3 is selected from the group consisting of hydrogen, methyl and ethyl.

6. A compound according to claim 1 , wherein A 1 to A 4 are each independently selected from the group consisting of a bond, CR 8 , N, S and O, and A 1 to A 4 together with the atoms to which they are joined form a 5 to 6 membered aryl or heteroaryl.

7. A compound according to claim 1 , wherein A 1 to A 4 are each CR 8 .

8. A composition comprising a compound according to claim 1 , and an agriculturally acceptable formulation adjuvant.

9. A mixture comprising a compound as defined in claim 1 , and a further active ingredient.

10. A crop yield enhancing composition, comprising a compound according to claim 1 .

11. A method for improving the tolerance of a plant to abiotic stress, promoting seed germination of a plant, or 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 .

12. A compound according to claim 1 , wherein Z is CH 2 .

13. A compound according to claim 1 , selected from: ethyl (E)-2-indan-1 -yl-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxy]prop-2-enoate; ethyl (E)-3-[(3,4-dimethyl-5-oxo-2H-furan-2-yl)oxy]-2-indan-l-yl-prop-2-enoate; methyl (E)-2-indan-l-yl-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxy]prop-2-enoate; methyl (E)-3-[(3,4-dimethyl-5-oxo-2H-furan-2-yl)oxy]-2-indan-l-yl-prop-2-enoate; ethyl (E)-2-(5,6-dimethoxyindan-l-yl)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxy]prop-2-enoate; ethyl (E)-2-(5,6-dimethoxyindan-1 -yl)-3-[(3,4-dimethyl-5-oxo-2H-furan-2-yl)oxy]prop-2-enoate; ethyl (E)-2-(6,7-dihydro-5H-cyclopenta[f[[1,3]benzodioxol-7-yl)-3-[(4-methyl-5-oxo-2H-furan-2-y 1)oxy]prop-2-enoate; ethyl (E)-2-(4-methylindan-l-yl)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxy]prop-2-enoate; ethyl (E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxy]-2-[4-(trifluoromethyl)indan-l-yl]prop-2-enoate; ethyl (E)-3-[(3,4-dimethyl-5-oxo-2H-furan-2-yl)oxy]-2-(6-hydroxyindan-l-yl)prop-2-enoate; ethyl (E)-3-[(3,4-dimethyl-5-oxo-2H-furan-2-yl)oxy]-2-tetralin-l-yl-prop-2-enoate; ethyl (E)-2-(7-bicyclo[4.2.0]octa-l(6),2,4-trienyl)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxy]prop-2-enoate; ethyl (E)-2-(5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl)-3-[(3,4-dimethyl-5-oxo-2H-furan-2-yl)oxy]prop-2-enoate; ethyl (E)-2-chroman-4-yl-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxy]prop-2-enoate; ethyl (E)-2-chroman-4-yl-3-[(3,4-dimethyl-5-oxo-2H-furan-2-yl)oxy]prop-2-enoate; and ethyl (E)-2-(2,3-dihydrobenzofuran-3-yl)-3-[(3,4-dimethyl-5-oxo-2H-furan-2-yl)oxy]prop-2-enoate.

Assignees

• Syngenta Participations Ag

Inventors

• Lumbroso Alexandre Franco Jean Camille
• De Mesmaeker Alain
• Screpanti Claudio
• Rendine Stefano

Classifications

• C07D409/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D407/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D307/33

  in position 2, the oxygen atom being in its keto or unsubstituted enol form · CPC title

• C07D207/38 Primary

  2-Pyrrolones · CPC title

• A01P21/00

  Plant growth regulators · CPC title