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Oxime-substituted amide compound and pest control agent

A technology of oxime-substituted amides and compounds, applied in the field of pest control agents, can solve problems such as changing the lifespan of eukaryotes

Active Publication Date: 2015-03-18
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In addition, known 2-chloro-N-[2-(4-chlorophenyl)-2-(methoxyimino)ethyl]benzamide, N-[2-(4-chlorophenyl)- 2-(methoxyimino)ethyl]-2,4-dichlorobenzamide, etc. will change the lifespan of eukaryotic organisms (see Patent Document 3)

Method used

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  • Oxime-substituted amide compound and pest control agent
  • Oxime-substituted amide compound and pest control agent
  • Oxime-substituted amide compound and pest control agent

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Embodiment

[0926] Hereinafter, the present invention will be further described in detail by specifically describing the synthesis examples and test examples of the compounds of the present invention as examples, but the present invention is not limited thereto.

Synthetic example 1

[0929] (Z)-N-[2-(2,4-dichlorophenyl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide (compound No. 1-004).

[0930] Step 1; Production of 2-bromo-1-(2,4-dichlorophenyl)ethanone-O-methyloxime

[0931] To a solution of 4.00 g of 2-bromo-1-(2,4-dichlorophenyl)ethanone in 20 ml of ethanol was added 1.25 g of methoxyamine hydrochloride, followed by stirring at room temperature for 12 hours. After the reaction, the solvent was distilled off under reduced pressure, 20 ml of water was added to the residue, and extraction was performed with ethyl acetate (20 ml×2). The organic layers were combined, washed with water (20ml×1), dehydrated and dried in the order of saturated brine, followed by anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the crude target compound 3.85 in the form of a light yellow oily substance. g. It was used directly in the next procedure without further purification.

[0932] 1 H NMR (CDCl 3 , Me 4 Si, 300MHz)...

Synthetic example 2

[0945] (Z)-N-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide (the present invention Compound No. 2-120).

[0946] Step 1; Production of 1-(3,5-dichloropyridin-2-yl)ethanone

[0947] To a solution of 20 g of 3,5-dichloropyridine-2-carbonitrile in 150 ml of tetrahydrofuran, 139 ml of a 1 M tetrahydrofuran solution of methylmagnesium bromide was added dropwise with stirring under ice cooling, and stirred at this temperature for 1 hour. After the reaction, 15ml of concentrated hydrochloric acid and 100ml of water were added to the reaction mixture, extracted with ethyl acetate (100ml×2), the organic layers were combined, washed with water (100ml×1), followed by saturated saline, followed by anhydrous sulfuric acid Dehydration and drying were performed sequentially with sodium, and the solvent was distilled off under reduced pressure. The residue was dissolved in 40 ml of ethyl acetate and 10 ml of hexane, 20 g of silica gel was added, stirred at ...

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Abstract

Provided is a novel pest control agent, particularly a fungicide and nematicide. An oxime-substituted amide compound represented by formula (I) [where G1 represents a structure represented by G1-1 or the like; G2 represents a structure represented by G2-2 or the like; W represents an oxygen atom or the like; X1 represents a halogen atom, methyl, trifluoromethyl, or the like; X2, X3, X4, and X5 each independently represent a hydrogen atom, halogen atom, or the like; Y1 and Y3 each independently represent a halogen atom, cyano, methyl, trifluoromethyl, C2-C6 alkynyl, or the like; Y2 and Y4 each independently represent a hydrogen atom, halogen atom, or the like; R1 represents a C1-C6 alkyl, C1-C4 haloalkyl, (C1-C4) alkyl substituted by R18, C3-C6 cycloalkyl, C3-C6 alkenyl, or the like; R2 and R3 each independently represent a hydrogen atom, methyl, or the like; R4 represents a hydrogen atom or the like; R18 represents a C3-C6 cycloalkyl, phenyl, phenyl substituted by (Z)m, or the like; Z represents a halogen atom or the like; and m represents an integer 1, 2, or 3] or a salt thereof, and a pest control agent containing these.

Description

Technical field [0001] The present invention relates to novel oxime-substituted amide compounds and salts thereof, and pest control agents containing the compounds as active ingredients. Background technique [0002] Conventionally, as oxime-substituted amide compounds, N-[2-(methoxyimino)-2-phenylethyl]-4-(trifluoromethyl)nicotinamide and 3-iodo-N have been known 2 -[2-(methoxyimino)-2-phenylethyl]-N 1 -[2-Methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]phthalic acid diamide exhibits insecticidal activity (e.g., see Patent Document 1 and Patent Document 2). [0003] In addition, 2-chloro-N-[2-(4-chlorophenyl)-2-(methoxyimino)ethyl]benzamide, N-[2-(4-chlorophenyl)- 2-(Methoxyimino)ethyl]-2,4-dichlorobenzamide and the like change the life span of eukaryotes (see Patent Document 3). [0004] Furthermore, it is known that certain pyrazole-4-carbonylamine derivatives have bactericidal activity (for example, see Patent Documents 4 to 7). [0005] However, there...

Claims

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Application Information

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IPC IPC(8): C07C251/48A01N35/10A01N43/10A01N43/40A01P3/00A01P5/00A61K31/381A61K31/44A61K31/4433A61K31/4436A61P31/04A61P33/00A61P33/10C07C251/52C07D213/42C07D213/61C07D213/82C07D333/38C07D407/12C07D409/12
CPCC07C251/52A01N43/56A01N43/84C07D409/12A01N43/76A01N43/60C07D213/61A01N43/80C07D407/12A01N43/10C07C251/48C07D213/42A01N37/20A01N43/78C07D333/38A01N43/40A01N47/12A01N43/713C07D213/82C07D213/65C07D401/12C07D213/53C07D241/24C07D405/12C07D413/12C07D417/12A61P31/00A61P31/04A61P31/10A61P33/00A61P33/02A61P33/06A61P33/10A61P33/12A61P33/14A01N35/10A61K31/381A61K31/44A61K31/4433A01N37/18A01N37/34A01N41/10A01N41/12A01N55/00C07C255/64C07C317/32C07C321/28C07D411/12C07F7/08C07F7/0814
Inventor 岩佐基悦辻敬介富泽光贵三田猛志桑原秀仁旭美穗今仲穗高
Owner NISSAN CHEM IND LTD
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