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Oxime substituted amide compounds and pest control agents
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An amide compound, oxime-substituted amide technology, applied in the field of pest control agents, can solve problems such as changing the lifespan of eukaryotes
Active Publication Date: 2017-10-20
NISSAN CHEM IND LTD
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[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)
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[0926] Hereinafter, the present invention will be explained in further detail by using 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. of the present invention) 1-004).
[0930] Step 1: Production of 2-bromo-1-(2,4-dichlorophenyl)ethanone-O-methyloxime
[0931] 1.25 g of methoxyamine hydrochloride was added to a solution of 4.00 g of 2-bromo-1-(2,4-dichlorophenyl)ethanone in 20 ml of ethanol, and the mixture was stirred 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), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the crude target product 3.85 in the form of a pale yellow oily substance g. It was used directly in the following process without further purification.
[0932] 1 H NMR(CD...
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] Under ice-cold stirring, 139 ml of a 1M tetrahydrofuran solution of methylmagnesium bromide was added dropwise to a solution of 20 g of 3,5-dichloropyridine-2-carbonitrile in 150 ml of tetrahydrofuran, and the mixture was 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 brine, followed by anhydrous sulfuric acid The sodium is dehydrated and dried in this order, and the solvent is 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 room temperatu...
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Abstract
The present invention provides novel pest control agents, particularly fungicides and nematicides. The present invention provides an oxime-substituted amide compound represented by formula (I) or a salt thereof, and a pest control agent containing them [in the formula, G1 represents a structure represented by G1-1, etc., and G2 represents a structure represented by G2-2, etc. The structure; W represents oxygen atom, etc., X1 represents halogen atom, methyl group, trifluoromethyl, etc., X2, X3, X4 and , cyano group, methyl, trifluoromethyl, C2~C6 alkynyl, etc., Y2 and Y4 each independently represent a hydrogen atom, a halogen atom, etc., R1 represents a C1~C6 alkyl group, C1~C4 haloalkyl group, substituted with R18 (C1~C4) alkyl, C3~C6 cycloalkyl, C3~C6 alkenyl, etc., R2 and R3 each independently represent a hydrogen atom, methyl, etc., R4 represents a hydrogen atom, etc., R18 represents a C3~C6 ring Alkyl group, phenyl group, phenyl group substituted with (Z)m, etc., Z represents a halogen atom, etc., and m represents an integer of 1, 2 or 3].
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...
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