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1-(4-(4-(5-phenyl-4, 5-dihydroisoxazol-3-yl) thiazol-2-yl) piperidin-1-yl)-ethane-1-one derivatives and related compounds as fungicides for crop protection

A compound, C1-C6 technology, applied in the control or prevention of phytopathogenic fungi, the preparation of 6-membered heteroaryl piperidinyl ethyl ketone, the field of intermediates of 6-membered heteroaryl piperidinyl ethyl ketone, Can solve the problem of toxicity, residue formation, etc.

Pending Publication Date: 2022-07-15
PI IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The effects of the oxazole-thiazopyridine heterocyclic compounds described in the prior art are relatively satisfactory, but problems remain to be solved, such as biological and ecological characteristics, fungicidal activity, activity profile, toxicity, selectivity , application rates, residue formation, and resistance

Method used

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  • 1-(4-(4-(5-phenyl-4, 5-dihydroisoxazol-3-yl) thiazol-2-yl) piperidin-1-yl)-ethane-1-one derivatives and related compounds as fungicides for crop protection
  • 1-(4-(4-(5-phenyl-4, 5-dihydroisoxazol-3-yl) thiazol-2-yl) piperidin-1-yl)-ethane-1-one derivatives and related compounds as fungicides for crop protection
  • 1-(4-(4-(5-phenyl-4, 5-dihydroisoxazol-3-yl) thiazol-2-yl) piperidin-1-yl)-ethane-1-one derivatives and related compounds as fungicides for crop protection

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0311] Example 1: 1-(4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidine-1- Preparation of yl)-2-((3-(trifluoromethyl)pyrazin-2-yl)oxy)ethane-1-one (compound 3)

[0312] Step A: Preparation of ethyl 2-bromo-1,3-thiazole-4-carboxylate

[0313] To a solution of ethyl 2-aminothiazole-4-carboxylate (100 g, 581 mmol) and copper(II) bromide (195 g, 871 mmol) in acetonitrile (1 L) at 0 °C was added tert-butyl nitrite (104 mL) dropwise , 871 mmol)). The reaction mixture was heated to 25°C and stirred for 12 hours. The reaction mixture was diluted with ethyl acetate (1 L) and water (3 L) and acidified to pH 2 using 1 N hydrochloric acid. The layers were separated and the aqueous layer was extracted three times with ethyl acetate (500 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, concentrated, and purified by recrystallization from hexane to obtain ethyl 2-bromo-1,3-thiazole-4-carboxylate (115 g, 84% yield). ).

[0314] ...

example 2

[0340] Example 2: 3-Chloro-2-(3-(2-(1-(2-((3-(trifluoromethyl)pyrazin-2-yl)oxy)acetyl)piperidin-4-yl) Preparation of Thiazol-4-yl)-4,5-dihydroisoxazol-5-yl) phenylmethanesulfonate

[0341] Step A: 3-Chloro-2-(3-(2-(1-(2-((3-(trifluoromethyl)pyrazin-2-yl)oxy)acetyl)piperidin-4-yl ) thiazol-4-yl)-4,5-dihydroisoxazol-5-yl) phenylmethanesulfonate preparation

[0342] To (E / Z)-tert-butyl 4-(4-((hydroxyimino)methyl)thiazol-2-yl)piperidine-1-carboxylate (4 g, 12.8 mmol) in ethyl acetate (500 mL) To the stirred solution was added N-chlorosuccinimide (2.57 g, 19.27 mmol) followed by sodium bicarbonate (7.55 g, 90 mmol). To the reaction mixture was added 3-chloro-2-vinylphenylmethanesulfonate (4.48 g, 19.27 mmol) and water (10 mL). The reaction mixture was heated to 65°C for 3 hours, cooled to 15°C and then quenched with water. The aqueous layer was extracted twice with ethyl acetate (50 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, concentrated a...

example 3

[0349] Example 3: Preparation of 2-((3-(trifluoromethyl)pyrazin-2-yl)oxy)acetic acid

[0350] Step A: Preparation of 3-(trifluoromethyl)pyrazin-2-ol

[0351] To a solution of pyrazin-2-ol (5 g, 52.0 mmol) and sodium trifluoromethanesulfinate (20.3 g, 130 mmol) in acetic acid (100 mL) was added manganese acetate dihydrate (41.9 g, 156 mmol) portionwise. The mixture was stirred at 25°C for 12 hours. Water (20 mL) was added to the reaction mixture and extracted twice with ethyl acetate. The combined ethyl acetate layers were dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (using 70% ethyl acetate in hexanes as eluent) to give 3-(trifluoromethyl)pyrazine-2 - Alcohol (2.2 g, 13.41 mmol, 26% yield).

[0352] MS: m / z=165.10 (M+1)

[0353] Step B: Preparation of tert-butyl 2-((3-(trifluoromethyl)pyrazin-2-yl)oxy)acetate

[0354]To a solution of 3-(trifluoromethyl)pyrazin-2-ol (0.9 g, 5.48 mmol) in toluene (50 mL) at 25 °C was added silver c...

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Abstract

The invention relates to a 1-(4-(4-(5-phenyl-4, 5-dihydroisoxazole-3-yl) thiazole-2-yl) piperidine-1-yl)-ethane-1-one derivative used as a crop protection bactericide and a related compound, and a preparation method of the 1-(4-(4-(5-phenyl-4, 5-dihydroisoxazole-3-yl) thiazole-2-yl) piperidine-1-yl)-ethane-1-one derivative. This specification discloses synthesis and characterization of exemplary compounds and their biological data (e.g., pages 55 to 94; embodiments 1 to 4; compounds 1 to 194; table 1).

Description

technical field [0001] The present invention relates to novel substituted 6-membered heteroarylpiperidinyl ethanones and agrochemically active salts, combinations, compositions and methods of using these compounds for the control or prevention of phytopathogenic fungi. The present invention also relates to a preparation method for the preparation of novel substituted 6-membered heteroarylpiperidinyl ethanones and intermediates for the preparation of novel substituted 6-membered heteroarylpiperidinyl ethanones. Background technique [0002] It is known from the prior art (eg WO2008013925, WO2012020060, WO2016024434, WO2019048988 and WO2019048989) that oxazole-thiazolepiperidine heterocyclic compounds are useful as fungicidal crop protection agents. [0003] The oxazole-thiazole piperidine heterocyclic compounds described in the prior art are more satisfactory but leave problems to be solved, such as biological and ecological characteristics, fungicidal activity, activity, tox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14A01N43/78A01N43/40A01N43/80A01N43/48A01N43/54A01N43/58A01N43/60A01N43/64A01N43/66A01N43/707A01N43/24
CPCC07D417/14A01N43/78A01N43/48A01N43/54A01N43/58A01N43/60A01N43/64A01N43/66A01N43/707A01N43/80A01N43/40A01N43/24
Inventor 加贾南·尚巴格辛加博埃纳·普拉巴卡尔阿南坦·巴克塔瓦查拉姆德亚内什瓦·安纳塔拉·瓦赫拉克什·迪克卡·库尔卡尼莫汉·库马尔·史瓦尼·普塔斯瓦米桑托什·什里达尔·奥特加鲁芝·加尔嘉维什瓦纳·加德亚历山大·G·M·克劳泽纳
Owner PI IND LTD
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