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Synergistic fungicide compositions containing at least one N-(2-pyridinyl) 1-3-pyridinecarboxamide derivative and one or more further fungicides useful for controlling fungal plant diseases

A plant disease and composition technology, applied in the field of pyridyl amides, can solve problems such as increased consumer costs and reduced yields

Inactive Publication Date: 2005-09-07
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Plant diseases Damage to ornamentals, vegetables, field crops, cereals, and fruit crops can lead to significant yield reductions and consequently increased costs to consumers

Method used

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  • Synergistic fungicide compositions containing at least one N-(2-pyridinyl) 1-3-pyridinecarboxamide derivative and one or more further fungicides useful for controlling fungal plant diseases
  • Synergistic fungicide compositions containing at least one N-(2-pyridinyl) 1-3-pyridinecarboxamide derivative and one or more further fungicides useful for controlling fungal plant diseases
  • Synergistic fungicide compositions containing at least one N-(2-pyridinyl) 1-3-pyridinecarboxamide derivative and one or more further fungicides useful for controlling fungal plant diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] 2,4-Dichloro- N- [[3-Chloro-5-(trifluoromethyl)-2-pyridyl]methyl]-6-methyl-3-

[0083] Preparation of pyridinecarboxamide

[0084] Step A: 2,4-Dichloro- N- [[3-Chloro-5-(trifluoromethyl)-2-pyridyl]methyl]-6-methyl-3-pyridine Preparation of pyridine carboxamide

[0085] To a solution of 2,4-dichloro-6-methyl-3-pyridinecarbonyl chloride (0.65 g) in 2 mL of dichloromethane was added 2-aminomethyl-3-chloro-5-trifluoromethyl - A solution of pyridine hydrochloride (prepared as described in WO99 / 42447) (0.79 g) and triethylamine (0.68 g) in 10 mL of dichloromethane. The reaction mixture was stirred overnight at room temperature. The reaction mixture was then poured onto a 1 inch plug of silica gel, eluted with 30 mL of dichloromethane, and the eluate was concentrated to give 0.69 g of the title compound, a compound of the present invention.

[0086] 1 H NMR (CDCl 3 )δ2.57(s, 3H), 4.96(m, 2H), 7.22(s, LH), 7.48(bs, 1H), 8.00(s, LH), 8.71(s, 1H).

Embodiment 2

[0088] 2,4-Dichloro- N- Preparation of [[3-chloro-5-(trifluoromethyl)-2-pyridyl]methyl]-3-pyridinecarboxamide

[0089] Step A: Preparation of 2,4-dichloropyridine

[0090] 6.7g 4-nitropyridine N-oxide in POCl 3 The solution in was refluxed for 3 hours and then cooled to room temperature. The solvent was removed in vacuo to leave an oily residue. Saturated aqueous sodium bicarbonate (200 mL) was added carefully, followed by extraction with dichloromethane (2X). The dichloromethane was then removed in vacuo to give an oil which was filtered through a plug of silica gel eluting with 20% ethyl acetate in hexanes. The solvent was removed in vacuo to leave 1.6 g of an oil.

[0091] 1 H NMR (CDCl 3 ) δ 7.25 (dd, 1H, J=1.7 and 5.4Hz), 7.38 (d, 1H, J=1.7Hz), 8.31 (d, 1H, J=5.4HZ).

[0092] Step B: Preparation of 2,4-dichloro-3-pyridinecarboxaldehyde

[0093] To a solution of 1.6 g of 2,4-dichloropyridine (the product of Step A) in 5 mL of dry THF was added a solution of...

Embodiment 3

[0101] 2,4-Dichloro- N- [1-[3-Chloro-5-(trifluoromethyl)-2-pyridyl]ethyl]-3-pyridine

[0102] Preparation of carboxamides

[0103] Step A: Preparation of 3-chloro-α-methyl-5-(trifluoromethyl)-2-pyridinemethanamine

[0104] Add N-(diphenylmethylene)glycine ethyl ester (2.25 g) to a suspension of sodium hydride (0.74 g of a 60% oil dispersion) in 20 mL of dry N,N-dimethylformamide at room temperature During, gas was evolved violently. After stirring at room temperature for 5 minutes, 2 g of 2,3-dichloro-5-trifluoromethylpyridine was added, followed by stirring at room temperature for 1 hour. Then 0.80 mL of methyl iodide was added, followed by stirring overnight at room temperature. The reaction mixture was poured into ice water, extracted with diethyl ether (2X), and the solvent was distilled off in vacuo to give an oil. The oil was then refluxed overnight in 6N HCl. The reaction mixture was cooled to room temperature, made basic with solid sodium carbonate, and ex...

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Abstract

Compositions for controlling plant diseases caused by fungal plant pathogens are described, comprising: (a) at least one compound of Formula I, including all geometric and stereoisomers, N-oxides and agriculturally suitable salts thereof: I-wherein R1, R2, R5 and R6, m and n are as defined in the disclosure; and (b) at least one compound selected from the group consisting of (b1) alkylenebis(dithiocarbamate) fungicides; (b2) compounds acting at the bc1 complex of the fungal mitochondrial respiratory electron transfer site; (b3) cymoxanil; (b4) compounds acting at the demethylase enzyme of the sterol biosynthesis pathway; (b5) morpholine and piperidine compounds that act on the sterol biosynthesis pathway; (b6) phenylamide fungicides; (b7) pyrimidinone fungicides; (b8) phthalimides; and (b9) fosetyl-aluminum. Also disclosed are methods for controlling plant diseases caused by fungal plant pathogens that involves applying an effective amount of the combinations described.

Description

technical field [0001] The present invention relates to certain pyridylamides, their N-oxides, agriculturally suitable salts, certain beneficial compositions comprising mixtures of pyridylamides and other fungicides, and methods of their use as fungicides. Background technique [0002] In order to achieve high crop efficiency, the control of plant diseases caused by fungal phytopathogens is extremely important. Damage by plant diseases to ornamentals, vegetables, field crops, cereals, and fruit tree crops can lead to a significant reduction in yield and thus to increased costs to the consumer. For the control of plant diseases, many products are already commercially available, but there is still a need for new products that are more effective, less expensive, less toxic, or safer for the environment. [0003] Certain pyridylamides of the formula i of WO 01 / 11966 as fungicides: [0004] [0005] Among them, in particular, [0006] A 1 is 2-pyridyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/40A01N25/04A01N25/12A01N25/14A01N43/54A01N43/76A01N43/84A01N47/10A01N47/14A01N47/34A01N55/02A01P3/00C07DC07D401/12
CPCA01N43/40A01N43/76A01N47/14A01N47/34A01N57/12A01N2300/00
Inventor 斯蒂芬·雷·弗奥迈克尔·保罗·沃克
Owner EI DU PONT DE NEMOURS & CO
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