4-amino-6-(halo-substituted-alkyl)-picolinates and their use as herbicides

A technology of alkyl and halogen atoms, applied in 4-amino-6-(halogen-substituted alkyl)-picolinate and their use as herbicides, can solve problems such as affecting crop yields

Inactive Publication Date: 2016-09-07
DOW AGROSCIENCES LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Weeds compete with crops, adversely affecting crop yields

Method used

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  • 4-amino-6-(halo-substituted-alkyl)-picolinates and their use as herbicides
  • 4-amino-6-(halo-substituted-alkyl)-picolinates and their use as herbicides
  • 4-amino-6-(halo-substituted-alkyl)-picolinates and their use as herbicides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] Embodiment 1: Preparation of methyl 4-amino-3-chloro-6-vinylpicolinate (C1)

[0096]

[0097] Methyl 4-amino-3,6-dichloropicolinate (2.50 g, 11.3 mmol), vinyltributyltin (7.17 g, 22.6 mmol), and bis(triphenylphosphine)palladium(II) dichloride (1.19g, 1.70mmol) in 1,2-dichloroethane (12mL) into a 25-mL vial and seal the cap, which was placed in the Biotage Heat at 120° C. for 30 minutes in a microwave reactor with an external IR-sensor temperature monitored from the side of the vessel. The mixture was loaded directly onto a silica gel column and purified by flash column chromatography (0-40% ethyl acetate / hexanes) to give the title compound (2.03 g, 84%) as a yellow solid: mp 74.5 - 76.5 °C; 1 H NMR (400MHz, CDCl 3 ( s, 2H), 3.98(s, 3H); 13 C NMR (400MHz, CDCl 3 )δ165.8, 154.0, 150.3, 148.0, 135.8, 119.3, 113.5, 107.7, 52.9; ESIMS m / z 213 ([M+H] + ).

[0098] The following compounds were prepared according to the procedure in Example 1:

[0099] Methyl 4-amin...

Embodiment 2

[0111] Example 2: Preparation of methyl 4-amino-3-chloro-6-(1-fluorovinyl)picolinate (F6)

[0112]

[0113] Methyl 4-acetylamino-3,6-dichloropicolinate (0.528g, 2.01mmol), tributyl(1-fluorovinyl)stannane (1.00g, 3.00mmol), and bis(triphenyl A mixture of phosphine)palladium(II) dichloride (0.225g, 0.320mmol) in 1,2-dichloroethane (4mL) was heated at 80°C for 8 hours. The reaction mixture was directly purified by flash column chromatography (0-50% ethyl acetate / hexanes) to give methyl 4-acetamido-3-chloro-6-(1-fluorovinyl)picolinate as an impure mixture (0.512g). To the crude intermediate at 0 °C in methanol (19 mL) was added acetyl chloride (2.90 mL, 37.6 mmol) dropwise. After 30 minutes the ice bath was removed and the reaction mixture was allowed to warm to room temperature and stirred overnight. Methanol was removed in vacuo, and the reaction mixture was neutralized with saturated aqueous sodium bicarbonate. The aqueous solution was extracted three times with ethyl ac...

Embodiment 3

[0114] Example 3: Preparation of methyl 4-amino-3-chloro-5-fluoro-6-(1-fluorovinyl)picolinate (F22)

[0115]

[0116] Methyl 4-amino-3,6-dichloro-5-fluoropicolinate (0.374g, 1.57mmol), tributyl(1-fluorovinyl)stannane (0.590g, 1.76mmol), and bis( A mixture of triphenylphosphine)palladium(II) dichloride (0.175 g, 0.250 mmol) in 1,2-dichloroethane (7 mL) was heated at 70° C. for 3 hours. The reaction mixture was directly purified by flash column chromatography (0-60% ethyl acetate / hexanes). A second purification by reverse phase flash column chromatography (0-40%, 40-40%, 40-100% acetonitrile / water) afforded the title compound (0.0810 g, 21%) as a white powder.

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PUM

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Abstract

Provided herein are 4-amino-6-(halo-substituted-alkyl)-picolinic acids and their derivatives, compositions comprising the acids and their derivatives, and methods of use thereof as herbicides. The compositions can include herbicide safeners, adjuvants, and carriers. Also provided are methods controlling undesirable vegetation in glyphosate tolerant crops, glufosinate tolerant crops, dicamba tolerant crops 2,4-D tolerant crops, ALS tolerant crops, or ACCase tolerant crops.

Description

Background technique [0001] The appearance of unwanted vegetation such as weeds is a constant problem faced by farmers of crops, pastures and other environments. Weeds compete with crops, adversely affecting crop yields. The use of chemical herbicides is an important tool in controlling unwanted vegetation. [0002] There remains a need for new chemical herbicides that provide broad-spectrum weed control, selectivity, minimal crop injury, storage stability, ease of handling, high activity against weeds, and / or address issues developed for currently used herbicides. approach to herbicide tolerance. Contents of the invention [0003] The application provides a compound of formula (I) or its N-oxide or agricultural salt: [0004] [0005] in [0006] R 1 is C optionally substituted with one or more halogen atoms 1 -C 4 Alkyl or C 1 -C 4 alkenyl with the proviso that R 1 is not 1,1-difluoroethyl or trifluoromethyl; [0007] R 2 is H, Cl or F; [0008] R 3 is hal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/79
CPCA01N47/20A01N43/40C07D213/79
Inventor J·B·埃普L·G·费希尔J·基斯特N·M·萨奇维P·R·施米策
Owner DOW AGROSCIENCES LLC
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