Methionine metabolic pathway inhibitors
Inventors
Bloch, Itai • Cohen, Elad • Amir, Rachel • GAL, Maayan
Assignees
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Publication Number
US-11639345-B2
Publication Date
2023-05-02
Expiration Date
Abstract
The present invention provides novel inhibitors of cystathionin gamma synthase (CGS), their use as selective and non-selective herbicides, agricultural and non-agricultural herbicides, herbicides in integrated pest management, herbicides for gardening, clearing waste ground, clearing industrial or constructions sites, clearing railways and railway embankments, pesticide, fungicide, agricultural plant stimulant or antimicrobial agent. Also provided is a method for the control of undesired vegetation or clearing areas from the undesired vegetation comprising applying to the locus of said undesired vegetation, to the undesired plants or to a habitat thereof, a herbicidally effective amount of the compound of the present invention.
Core Innovation
The invention relates to methionine metabolic pathway inhibition by inhibiting cystathionin γ-synthase (CGS) using small-molecule CGS inhibitors. It is described in the context of the trans-sulphuration pathway and the metB gene, and positions CGS inhibition as a way to interfere with methionine metabolic pathway activity in plants, fungi, and bacteria.
The core chemical innovation is a structural invention around Formula (I), Formula (IA1), and Formula (ID), with compounds defined by substituent constraints. X and Y are independently CH or N, Z is C—R8 or N, R8 is hydrogen, L is N—R9, and R9 is phenyl or pyridinyl optionally substituted with one to three halogen atoms, together with selected options for R15 and R16.
The document describes exemplary compound embodiments such as IML-223, IML-224, IMS-13, IML-202, IML-221/IMS-198, IML-30/31/32/162, IML-120/121/253, IML-124, IML-125, IML-161, IML-163, IML-164, IML-166 to IML-183, IML-238, IML-24, IML-64, IML-69, IML-215, IML-216, IML-229, IML-230, and IML-232. These members are presented in the context of biological activity readouts in E. coli and plant assays, including MST Tobacco, Arabidopsis, TEV, tobacco BY-2 cells, and Roquette tobacco assays.
Claims Coverage
The consolidated claim coverage includes 1 independent claim directed to a compound of Formula (ID), together with dependent claims that narrow the compound selection and recite agricultural and biocidal uses and vegetation control methods. Across the inventive features, the claims focus on the constrained Formula (ID) structure, selection of depicted exemplified compounds, and use as herbicide, pesticide, fungicide, agricultural plant stimulant, or antimicrobial agent. The method claims further recite controlling undesired vegetation by applying a herbicidally effective amount to specified plants or loci.
Compound of formula (id) with constrained substituents
A compound of Formula (ID) wherein X and Y are independently CH or N; Z is C—R8 or N; R8 is hydrogen; L is N—R9; R9 is phenyl or pyridinyl optionally substituted with one to three halogen atoms; R15 is selected from hydrogen, halogen, nitro and carboxylic acid group; and R16 is hydrogen or carboxylic acid group.
Specific exemplified formula (id) compounds
A compound selected from the compounds depicted in the provided structures and identified in the partial claim material, including named embodiments such as IML-30, IML-33, IML-31, IML-32, IML-162, IML-120, IML-121, and IML253.
Use as herbicide, pesticide, fungicide, agricultural plant stimulant, or antimicrobial agent
Use of the compound of Formula (ID) as one or more specified types of herbicide, pesticide, fungicide, agricultural plant stimulant, or antimicrobial agent.
Herbicidal control method by applying a herbicidally effective amount
A method of controlling undesired vegetation by applying a herbicidally effective amount of the compound to undesired plants, their habitat, or the location where they grow.
Herbicidal control limited to specified loci
The method further specifies that the locus is located in agricultural areas, crop fields, gardens, waste grounds, industrial or construction sites, railways, or railway embankments.
Claim coverage centers on a compound of Formula (ID) with specific constraints on X, Y, Z, R8, L/R9 aromatic substitution, and the R15/R16 groups. Dependent claims narrow the compound to specific exemplified structures and expand coverage to herbicide/pesticide/fungicide/agricultural plant stimulant/antimicrobial uses and to controlling undesired vegetation by applying a herbicidally effective amount to plants, habitat, or specified loci.
Stated Advantages
Stronger root-shortening effect is indicated by a lower ratio of root length versus the non-treated DMSO control in the Arabidopsis root-length evaluation context.
Documented Applications
Herbicide use for controlling undesired vegetation by applying a herbicidally effective amount to undesired plants, their habitat, or the site where they grow.
Herbicide use across specified loci including agricultural areas, crop fields, gardens, waste grounds, industrial or construction sites, railways, and railway embankments.
Use as one or more specified types of herbicide, pesticide, fungicide, agricultural plant stimulant, or antimicrobial agent.
Selective or non-selective herbicide use, including herbicide in integrated pest management, gardening, clearing waste ground, clearing industrial or constructions sites, and clearing railways and railway embankments.
Seed treatment.
Biological activity evaluation of exemplified Formula (ID) compound members in E. coli assays.
Biological activity evaluation of exemplified Formula (ID) compound members in plant assays including MST Tobacco and Arabidopsis.
Biological activity evaluation of exemplified Formula (ID) compound members in TEV assays.
Biological activity evaluation of exemplified Formula (ID) compound members in tobacco BY-2 cells.
Biological activity evaluation of exemplified Formula (ID) compound members in Roquette tobacco assays.
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