N-2-(hetero)arylethylcarboxamide derivative, and pest-controlling agent comprising the same

一种芳基乙基甲酰胺、衍生物的技术，应用在杀生物剂、用于生物控制的化学品、杀生剂等方向

Active Publication Date: 2009-04-08
NIHON NOHYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, in the prior art, the effect and control range of plant disease control agents are not entirely sufficient

Method used

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  • N-2-(hetero)arylethylcarboxamide derivative, and pest-controlling agent comprising the same
  • N-2-(hetero)arylethylcarboxamide derivative, and pest-controlling agent comprising the same
  • N-2-(hetero)arylethylcarboxamide derivative, and pest-controlling agent comprising the same

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0627] Preparation method of intermediate product 1 (when R 1 And R 2 When it is a hydrogen atom)

[0628]

[0629] Where R 3 , R 4 , E, Y and n are as defined above.

[0630] The above reaction can be carried out according to the method described in known publications (for example, Tetrahedron, 2002, 58(11), page 2211, etc.) or a method similar thereto. That is, the 2-(hetero)arylethylamine derivative represented by formula (III-1) can be produced as follows: in the presence of a base in an inert solvent, the acetonitrile derivative represented by formula (IV) and the corresponding The alkylating agent reacts to obtain the (hetero)arylacetonitrile derivative represented by the formula (V), and then, with or without separating the (hetero)arylacetonitrile derivative (V), the catalyst (for example, In the presence of Raney-nickel, etc., the hydrogenation reaction is carried out in an inert solvent, or the reduction reaction is carried out using a reducing agent (for example, lith...

Embodiment 1

[0782] Example 1. Preparation of N-[2-(2,4-Dichloro-phenyl)-1-methylethyl]-2-trifluoromethylbenzamide (Compound No. 1-32)

[0783] 1-1)

[0784]A mixture of 2,4-dichlorobenzaldehyde (1.45 g, 8.3 mmol), ammonium acetate (0.64 g, 8.3 mmol) and nitroethane (6 g, 80 mmol) was heated to reflux for 6 hours. The mixture was cooled to room temperature and ethyl acetate was added. The mixture was washed with water and saturated brine, then the mixture was dried with anhydrous magnesium sulfate, and then the mixture was concentrated. The concentrated mixture was recrystallized from ethanol to obtain 2,4-dichloro-1-(2-nitro-1-propenyl)benzene (yellow needle crystals, yield: 1.0 g, 52%).

[0785] 1-2)

[0786] At room temperature, a solution of 2,4-dichloro-1-(2-nitro-1-propenyl)benzene (1.0 g, 4.3 mmol) in tetrahydrofuran (5 ml) was added dropwise to the solution containing lithium aluminum hydride ( 0.33 g, 8.9 mmol) in tetrahydrofuran (20 ml) suspension. After that, reflux was started slow...

Embodiment 2

[0791] Example 2. N-[2-(2,4-Dichlorophenyl)-1-methylethyl]-2-trifluoromethylpyrazine-3-carboxamide (Compound No. 3-43) preparation

[0792] Add 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.3 g, 1.6 mmol) to the 2-trifluoromethylpyrazine-3-carboxylic acid ( 0.25 g, 1.3 mmol), [2-(2,4-dichlorophenyl)-1-methylethyl]amine (0.27 g, 1.3 mmol) and 4-dimethylaminopyridine (0.19 g , 1.6 mmol) in chloroform (10 ml) and the mixture was stirred at room temperature for 12 hours. After adding water and chloroform, the mixture was separated into layers, and the organic layer was washed successively with water and saturated brine and dried over anhydrous sodium sulfate. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) ​​to obtain the desired compound (yield: 0.31 g, 63%).

[0793] Properties: The melting point is 163 to 164°C.

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Abstract

Disclosed is an N-2-(hetero)arylethylcarboxamide derivative represented by the general formula (I) or a salt thereof: (I) wherein R<1> and R<2> independently represent a hydrogen atom or the like; R<3> and R<4> independently represent a hydrogen atom or the like; Y represents a halogen atom, a (C1-C6)alkyl group which may be substituted by a halogen atom, or the like; n is an integer of 1 to 5; A represents a specific substituted cyclic group; and E represents C-H, C-Y (wherein Y is as defined above) or a nitrogen atom. Also disclosed is a pest-controlling agent comprising the derivative or the salt as an active ingredient. The derivative, the salt and the pest-controlling agent have superior properties to conventional ones, and are particularly useful as an excellent plant disease-controlling agent or nematocidal agent which can show a wide controlling spectrum at a low dose.

Description

Technical field [0001] The present invention relates to N-2-(hetero)arylethylformamide derivatives, their salts and insect pest control agents containing the compound as an active ingredient, in particular to a plant disease control agent, nematicide, and Instructions. Background technique [0002] Generally, certain kinds of N-2-(hetero)arylethylformamide derivatives are known to have fungicidal activity (for example, see JP-A-1-151546, WO 04 / 016088, WO 04 / 074280 or WO 06 / 016708). [0003] However, the phenethylformamide derivative described in JP-A-1-151546 is difficult to exhibit activity against plant diseases on a practical level. Although the carboxamide derivatives described in WO 04 / 016088, WO 04 / 074280 and WO 06 / 016708 sometimes exhibit high fungicidal activity, these carboxamide derivatives do not have a satisfactory fungicidal range. There are still problems in such areas. Therefore, in the prior art, the effect and control range of plant disease control agents are not...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/66A01N37/18A01N43/08A01N43/10A01N43/32A01N43/40A01N43/56A01N43/60A01N43/78A01N47/02A01P3/00C07C233/65C07C233/73C07D213/82C07D231/14C07D241/24C07D277/20C07D277/56C07D307/56C07D327/06C07D333/38
CPCC07D241/24A01N37/18A01N43/08A01N43/56A01N43/60A01N37/40C07D327/06A01N43/10C07D277/20C07D277/56A01N47/02A01N43/78C07D333/38C07D307/56A01N43/40C07D231/14A01N43/32C07D213/82C07C233/66
Inventor 织田雅次松崎义广田中浩二泷泽英二长谷部元宏黑木信孝诹访明之大岛贤治
Owner NIHON NOHYAKU CO LTD
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