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Macrocyclic pyridine‑2‑amides as fungicides

A technology of fungi and pesticides, applied in the direction of fungicides, biocides, biocides, etc.

Inactive Publication Date: 2017-03-29
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 pyridine‑2‑amides as fungicides
  • Macrocyclic pyridine‑2‑amides as fungicides
  • Macrocyclic pyridine‑2‑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-methallyloxy)dihydrofuran-2(3H)-one

[0104]

[0105] In nitrogen (N 2 ), to stirred (3R,4R,5S)-3,4-dihydroxy-5-methyldihydrofuran-2(3H)-one (1.3 grams (g), 9.84 millimoles (mmol)) and Pd(Ph 3 P) 4 (0.569 g, 0.492 mmol) in anhydrous THF (9 milliliters (mL)) was added bis(2-methallyl) carbonate. Stir the solution at 60°C for 1 hour (h) (CO 2 After evolution ceased), the reaction mixture was cooled and the solvent was evaporated. By flash chromatography (silica gel (SiO 2 )) Purification of the crude product afforded the title compound as a colorless oil (2.3 g, 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=7.2Hz, 1H), 1.78(s, 3H), 1.75(s, 3H), 1.48(d, J=6.3Hz, 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[M + ]...

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-dicarboxylate 1-benzyl 2-methyl ester (110 mg, 0.468 mmol) in CH 2 Cl 2 (1.5 mL) was added BF 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, then stirred at 0 °C for 3 h. By flash chromatography (SiO 2 ) directly purified the reaction mixture to afford the title compound as a colorless oil (208 mg, 83%): 1 HNMR (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 )δ170.72,156.04,138.16,138.08,136.24,128.54,128.49,128.47,128.20,128.13,127.99,127.91,127.89,12...

Embodiment 3

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

[0144]

[0145] To a cooled (-10 °C) suspension of NaH (60% dispersion in mineral oil, 6.73 g, 168 mmol) in DMF (240 mL) was added dropwise (+)-dimethyltartrate (+)-L-tartrate over 30 min. 15.0 g, 84.0 mmol) in DMF (40 mL). After the addition was complete, the mixture was stirred at -10 °C for an additional 30 min, then 3-bromo-2-methylpropene (25.5 mL, 253 mmol) was added while keeping the reaction temperature below 0 °C. The mixture was stirred at -10 °C for 1.5 h, washed with 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 phases were washed with brine, washed with magnesium sulfate (MgSO 4 ) was dried, filtered and concentrated to give a yellow oil. By flash chromatography (SiO 2 , hexane / EtOAc gradient) to a...

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Abstract

The present invention relates to macrocyclic pyridine-2-amides of formula I and their use as fungicides. The compounds disclosed herein provide protection against Ascomycetes, Basidiomycetes, Deuteromycetes and Oomycetes. The present invention provides a method of controlling or preventing fungal attack on a plant, said method comprising the step of applying to at least one of the fungus, the plant and an area adjacent the plant a fungicidally effective amount of one or more Compounds described herein.

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 Patents(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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