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Macrocyclic-2-picolin amides as fungicides

A fungus, alkyl technology, applied in the direction of fungicides, biocides, biocides, etc.

Inactive Publication Date: 2015-03-25
DOW AGROSCIENCES LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Often, a single fungicide cannot be used in all situations

Method used

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  • Macrocyclic-2-picolin amides as fungicides
  • Macrocyclic-2-picolin amides as fungicides
  • Macrocyclic-2-picolin amides as fungicides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Example 1, Step 1: Preparation of (3R,4S,5S)-5-methyl-3,4-bis(2-methylallyloxy)dihydrofuran-2(3H)-one

[0104]

[0105] In nitrogen (N 2 ), to the stirred (3R, 4R, 5S)-3,4-dihydroxy-5-methyldihydrofuran-2(3H)-one (1.3 g (g), 9.84 millimoles (mmol)) and Pd(Ph 3 P) 4 (0.569 g, 0.492 mmol) was added bis(2-methylallyl) carbonate to a solution in dry THF (9 milliliters (mL)). Stir the solution at 60°C for 1 hour (h) (CO 2 After the escape ceases), the reaction mixture is cooled and the solvent is evaporated. By flash chromatography (silica gel (SiO 2 )) Purification of the crude product to obtain the title compound as a colorless oil (2.3g, 97%): 1 H NMR(400MHz, CDCl 3 )δ5.04(dd,J=1.9,0.9Hz,1H),5.00-4.98(m,1H),4.97-4.93(m,2H),4.47-4.38(m,1H),4.36-4.27(m, 1H), 4.23-4.00 (m, 4H), 3.82 (t, J = 7.2 Hz, 1H), 1.78 (s, 3H), 1.75 (s, 3H), 1.48 (d, J = 6.3 Hz, 3H); 13 C NMR(101MHz, CDCl 3 )δ172.65,141.07,140.92,113.54,113.14,84.19,79.31,76.57,74.53,74.51,19.48,19.35,19.00; EIMS m / z 240...

Embodiment 2

[0127] Example 2, Step 1: (S)-2-(Benzyloxycarbonylamino)-3-((2S,3S)-2,3-bis(benzyloxy)-4-hydroxybutoxy) Preparation of methyl propionate:

[0128]

[0129] At -78°C, to (2S,3S)-2,3-bis(benzyloxy)butane-1,4-diol (283mg, 0.935mmol) (such as Journal of Organic Chemistry 1991, 56(3) , Prepared as described in 1321-1322) and (S)-aziridine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (110 mg, 0.468 mmol) in CH 2 Cl 2 (1.5mL) add BF to the solution 3 -OEt 2 (10 μL, 0.081 mmol), and the reaction mixture was stirred at -78°C for 1 h, slowly warmed to 0°C, and then stirred at 0°C for 3 h. Through flash chromatography (SiO 2 ) The reaction mixture was directly purified to obtain the title compound as a colorless oil (208mg, 83%): 1 H NMR(400MHz, CDCl 3 )δ7.45-7.20(m,16H), 5.70(d,J=8.5Hz,1H), 4.70-4.54(m,6H), 4.53-4.46(m,1H), 3.93(dd,J=9.5, 3.2Hz, 1H), 3.80-3.53 (m, 9H), 2.09-1.96 (m, 1H); 13 C NMR(101MHz, CDCl 3 )δ170.72,156.04,138.16,138.08,136.24,128.54,128.49,128.47,128.20,128.13...

Embodiment 3

[0143] Example 3, Step 1: Preparation of dimethyl (2R,3R)-2,3-bis((2-methylallyl)oxy)succinate:

[0144]

[0145] Over a period of 30 minutes, to the cooled (-10°C) NaH (60% dispersion in mineral oil, 6.73g, 168mmol) suspension in DMF (240mL) was added dropwise (+)-L-dimethyl tartrate ( 15.0 g, 84.0 mmol) in DMF (40 mL). After the addition was complete, the mixture was stirred at -10°C for another 30 min, and then 3-bromo-2-methylpropene (25.5 mL, 253 mmol) was added while keeping the reaction temperature below 0°C. Stir the mixture at -10°C for 1.5h, use H 2 It was quenched with O and saturated aqueous sodium chloride (NaCl, brine) and extracted with EtOAc. The two phases were separated and the aqueous phase was further extracted with EtOAc. The combined organic phase was washed with brine, and magnesium sulfate (MgSO 4 ) Dry, filter and concentrate to obtain a yellow oil. Through flash chromatography (SiO 2 , Hexane / EtOAc gradient) to obtain the title compound as a colorless...

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Abstract

The present disclosure relates to macrocyclic-2-picolin amides and a use as a fungicide. The compounds of the present disclosure may offer protection against ascomycetes, basidiomycetes, deuteromycetes and oomycetes. The present disclosure presents a method for the control or prevention of fungal attack on a plant, the method including the steps of applying a fungicidally effective amount of one or more of the compounds described to at least one of the fungus, the plant, and an area adjacent to the plant.

Description

[0001] Cross-references to related applications [0002] This application claims the benefit of U.S. Provisional Application 61 / 643753, filed on May 7, 2012, which is expressly incorporated by reference into this application. Background technique [0003] Fungicides are compounds of natural or synthetic origin that protect and / or treat plants from damage caused by agriculturally relevant fungi. Often, a single fungicide cannot be used in all situations. Therefore, research is ongoing to produce fungicides that may have better performance, easier use, and lower cost. Contents of the invention [0004] The present invention relates to macrocyclic picolinamides and their use as fungicides. The compounds of the present invention provide protection against the ascomycetes, basidiomycetes, deuteromycetes and oomycetes. [0005] One embodiment of the invention may include compounds of formula I: [0006] [0007] R is H or C(O)R 6 ; [0008] R 1 is H, C(O)R 6 or Q; [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D321/00C07D405/12C07D493/04A01N43/24A01N43/40A01N47/18A01N43/90A01P3/00
CPCA01N43/24A01N43/40A01N43/90A01N47/18C07D321/00C07D405/12C07D493/04A01N2300/00
Inventor K·G·迈耶J·M·伦加B·M·纽金特F·李W·J·欧文C·姚K·布拉沃-阿尔塔米拉诺J·赫里克T·A·伯贝尔N·X·王P·R·格劳普纳R·J·希姆斯特拉
Owner DOW AGROSCIENCES LLC
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