Pyrabactin analogues to modulate plant development

Patent metadata

Field	Value
Publication number	US-2016333035-A1
Application number	US-201515112539-A
Country	US
Kind code	A1
Filing date	Jan 27, 2015
Priority date	Jan 28, 2014
Publication date	Nov 17, 2016
Grant date	—

Abstract

The present invention relates to compounds which can be used to control plant development. Indeed, the present invention discloses a new class of pyrabactin analogues which have a physiological effect on—for example—seed germination, and/or stomatal closure, and/or have developmental effects on root and shoot development and organogenesis. Hence, the latter compounds can be used to control plant development such as—for example—increasing the tolerance of plants to drought stress or to control physiological phenomena such as pre-harvest sprouting, tolerance to pathogens etc.

First claim

1 . A compound—or its salt—of the formula:

2 . A compound of the formula as given for E2, E3, E5 or E8:

3 . A method to synthesize a compound according to claim 1 , the method comprising:
phosphonylating a suitable halogenated benzene or naphthalene precursor via lithium halogen exchange and subsequent diethylchlorophosphate quench in order to obtain diethyl phenyl- or naphtylphosphonate intermediates, monodealkylating said diethyl phenyl- or naphtylphosphonate intermediates in basic hydrolysis conditions in order to obtain phosphonic acid intermediates, activating said phosphonic acid intermediates to their corresponding chlorophosphonates with thionylchloride, and, performing a nucleophilic displacement of said thionylchloride under basic conditions by means of a suitable benzyl-(n=1) or phenyl-(n=0) amine (Y═NH) or alcohol (Y═O), and interchanging the remaining phosphonate alkoxy group for a hydroxyl group via basic, lithium hydroxide mediated hydrolysis.

4 .- 5 . (canceled)

6 . An agricultural chemical formulation formulated for contacting to plants, the formulation comprising a compound according to claim 1 .

7 . A formulation according to claim 6 further comprising at least one of a herbicide, fungicide, pesticide, fertilizer or surfactant.

8 . A method of modulating plant development, the method comprising contacting a plant with a sufficient amount of the formulation according to claim 6 to modulate the development of said plant compared to not contacting the plant with said formulation.

9 . A method according to claim 8 wherein said modulation is increasing the tolerance to drought stress.

10 . A method of specifically inducing stomatal closure in a plant without affecting root or shoot growth, the method comprising contacting the plant with a sufficient amount of at least one of the compound E2, E3 or E8 of claim 2 .

11 . A method of specifically inhibiting seed germination in a plant, the method comprising contacting the plant with a sufficient amount of the compound E5 of claim 2 .

Assignees

• Univ Gent

Inventors

• Stevens Christian
• Geelen Danny
• Heugebaert Thomas
• Verstraeten Inge

Classifications

• A01N57/32

  containing heterocyclic radicals · CPC title

• C07F9/581 Primary

  Chemistry & Metallurgy · mapped topic

• A01N57/30

  containing aromatic radicals · CPC title

• A01N57/06

  containing aromatic radicals · CPC title

• C07F9/58 Primary

  Pyridine rings · CPC title