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Heterocyclic inhibitors of lysine biosynthesis via the diaminopimelate pathway

A diaminopimelic acid, biosynthesis technology, applied in the directions of biocides, animal repellents, plant growth regulators, etc., can solve the problems of herbicide-resistant weeds and the like

Inactive Publication Date: 2019-12-27
LA TROBE UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Unfortunately, repeated applications of herbicides with the same mechanism of action to crops or fields have resulted in the development of herbicide-resistant weeds

Method used

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  • Heterocyclic inhibitors of lysine biosynthesis via the diaminopimelate pathway
  • Heterocyclic inhibitors of lysine biosynthesis via the diaminopimelate pathway
  • Heterocyclic inhibitors of lysine biosynthesis via the diaminopimelate pathway

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0214] Embodiment 1-(Z)-2-(5-(4-fluorobenzylidene)-2,4-dioxothiazolidine-3-yl)acetic acid

[0215]

[0216] Step 1 - Synthesis of (Z)-2-(5-(4-fluorobenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl acetate

[0217]

[0218] To a solution of 4-fluorobenzaldehyde (0.211 mL, 1.97 mmol) and (Starting Material A) (0.400 g, 1.97 mmol) in toluene (8 mL) were added six drops of piperidine and four drops of acetic acid. The reaction was heated at reflux for 18 hours, after which time a yellow precipitate formed was allowed to cool. The precipitate was collected by vacuum filtration and washed with a small amount of toluene to give the desired compound (0.323 g, 53%).

[0219] δ H (400MHz, CDCl 3 ) 7.91 (s, 1H, CH), 7.53 (dd, J 8.0, 4.0, 2H, ArH), 7.19 (t, J 8.0, 2H, ArH), 4.48 (s, 2H, CH 2 ), 4.45 (q, J 16.0, 8.0, 2H, CH 2 ), 1, 30(t, J 8.0, 3H, CH 3 ).δ C (100MHz, CDCl 3 ) 167.2, 166.2, 165.5, 165.1, 162.5, 133.3, 132.4, 132.3, 129.42, 129.39, 120.8, 120.7, 116.7, 116.5, 62.2...

Embodiment 2

[0223] Synthesis of embodiment 2-(Z)-2-(5-benzylidene-2,4-dioxothiazolidin-3-yl)acetic acid

[0224]

[0225] Step 1 - Synthesis of (Z)-2-(5-benzylidene-2,4-dioxothiazolidin-3-yl) ethyl acetate

[0226]

[0227] To a solution of benzaldehyde (0.303 mL, 2.98 mmol) and (Starting Material A) (0.605 g, 2.98 mmol) in toluene (6 mL) were added three drops of piperidine and two drops of acetic acid. The reaction was heated at reflux for 18 hours, then concentrated in vacuo. The crude solid was washed with a small amount of methanol and collected by vacuum filtration to give the desired compound (0.532 g, 61%).

[0228] δ H (400MHz, CDCl 3 ) 7.94 (s, 1H, CH), 7.54-7.44 (m, 5H, ArH), 4.48 (s, 2H, CH 2 ), 4.25 (q, J 12, 0, 8.0, 2H, CH 2 ), 1.30 (t, J 6.0, 3H, CH 3 ).δ C (100MHz, CDCl 3 ) 167.5, 166.2, 165.6, 134.7, 133.1, 130.7, 130.3, 129.3, 121.1, 62.2, 42.1, 14.1.

[0229] Step 2 - Synthesis of (Z)-2-(5-benzylidene-2,4-dioxothiazolidin-3-yl)acetic acid

[0230] Ethyl ...

Embodiment 3

[0232] Synthesis of embodiment 3-(Z)-2-(5-(2-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetic acid

[0233]

[0234] Step 1 - Synthesis of (Z)-2-(5-(2-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl acetate

[0235]

[0236] To a solution of 2-methoxybenzaldehyde (0.402 g, 2.95 mmol) and starting material A (0.600 g, 2.95 mmol) in toluene (10 mL) were added six drops of piperidine and four drops of acetic acid. The reaction was heated at reflux for 18 hours, then concentrated in vacuo. The crude solid was washed with a small amount of methanol and collected by vacuum filtration to give the desired compound (0.639 g, 67%).

[0237] δ H (400MHz, CDCl 3 ) 8.31 (s, 1H, CH), 7.45 (t, J 8.0, 2H, ArH), 7.05 (t, J 8.0, 1H, ArH), 6.96 (d, J 8.0, 1H, ArH), 4.48 (s, 2H, CH 2 ), 4.25 (q, J 16.0, 8.0, 2H, CH 2 ), 3.91 (s, 3H, CH 3 ), 1.30(t, J 8.0, 3H, CH 3 ).δ C (100MHz, CDCl 3 ) 168.0, 166.3, 165.7, 158.6, 132.5, 130.5, 129.5, 122.3, 121.0, 120.9, 111.2, 62.1, 55....

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Abstract

The present invention relates to certain heterocyclic compounds of formula (1) that have the ability to inhibit lysine biosynthesis via the diaminopimelate biosynthesis pathway in certain organisms. As a result of this activity these compounds can be used in applications where inhibition of lysine biosynthesis is useful. Applications of this type include the use of the compounds as herbicides.

Description

technical field [0001] The present invention relates to substituted heterocyclic compounds capable of inhibiting lysine biosynthesis via the diaminopimelate pathway in certain organisms. As a result of this activity, these compounds are useful in applications where inhibition of lysine biosynthesis is useful. Applications of this type include the use of compounds as herbicides. Background technique [0002] During the 20th century, chemical agents were widely used in many applications, including as pharmaceuticals, herbicides, pesticides, etc. Unfortunately, due to the widespread use of these agents, many compounds that exhibit useful activity are no longer functional because the target species has developed some form of resistance to the active agent. [0003] The development and use of herbicides has a significant impact on the ability to feed a growing world population. Herbicides have helped farmers with weed management in crops and have also facilitated no-till crop ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/426A61K31/417A61K31/4166A01N43/74A01N43/76A01N43/78A01N43/50C07D233/96C07D263/02C07D277/24C07D277/26C07D277/28C07D277/30A61P31/04
CPCA01N43/50A01N43/74A01N43/76A01N43/78A61K31/4166A61K31/417A61K31/426A61P31/04A61K31/427
Inventor 马修·A·佩鲁吉尼别林达·阿沃特塔蒂亚娜·苏亚雷斯达科斯塔
Owner LA TROBE UNIVERSITY
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