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Substituted isoxazoline compound and pest control agent

A compound, isoxazoline technology, applied in plant growth regulators, biocides, animal repellents, etc., can solve problems such as unknown usefulness of pest control agents

Active Publication Date: 2009-04-01
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no disclosure about the substituted 4-(5-substituted-5-substituted aryl-4,5-dihydroisoxazol-3-yl)benzylamine compound of the present invention, and the compound is used as a pest control agent The usefulness of is also completely unknown

Method used

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  • Substituted isoxazoline compound and pest control agent
  • Substituted isoxazoline compound and pest control agent
  • Substituted isoxazoline compound and pest control agent

Examples

Experimental program
Comparison scheme
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Embodiment

[5764] Hereinafter, as examples, the synthesis examples and test examples of the present invention will be described in more detail, but the present invention is not limited to these.

Synthetic example 1

[5767] Preparation of the compound of the present invention using L-COS (a parallel liquid phase synthesis device manufactured by MORITEX).

[5768] Step 1: Preparation of 3,5-dichloro-1-(1-trifluoromethylvinyl)benzene

[5769] In a solution of 3,5-dichlorophenylboronic acid 25.0g in 200ml tetrahydrofuran and 100ml water, add 27.5g 2-bromo-3,3,3-trifluoropropene, 38.0g potassium carbonate and 1.84g dichlorobis(three Phenylphosphine) palladium(II) was stirred under heating and reflux for 3 hours. After the reaction is completed, let it cool to room temperature, add 500ml ice water, and extract with ethyl acetate (500ml×1). The organic layer was washed with water, then dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography in which the residue was eluted with hexane to obtain 25.7 g of the colorless oily target product.

[5770] 1 H NMR(CDCl 3 , Me 4 Si, 300MHz) δ7.41(t, J=2.0Hz, 1H)...

Synthetic example 2

[5806] 1-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenylmethyl]-3-(2 , 2,2-Trifluoroethyl)urea (Compound No. 5-001 of the present invention).

[5807] 0.20 g of 2,2,2-trifluoroethylamine was added to a 7.0 mL solution of 0.32 g of 1,1'-carbonyldi-1H-imidazole in tetrahydrofuran, and the mixture was stirred at room temperature for 1.5 hours. Next, 0.39 g of 3-[4-(aminomethyl)phenyl]-5-(3,5-dichlorophenyl)-5- synthesized in Step 6 of Synthesis Example 1 was added to the reaction mixture. A 5.0 mL solution of trifluoromethyl-4,5-dihydroisoxazole in tetrahydrofuran was stirred at room temperature for 2.5 hours. After the completion of the reaction, the reaction mixture was diluted with 20 mL of ethyl acetate, washed with water (15 mL×2), and then dehydrated and dried with saturated brine and anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (Y...

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Abstract

There is provided a novel pesticide, particularly an insecticide or an acaricide. A substituted isoxazoline compound of formula (1) or a salt thereof: wherein A 1 , A 2 and A 3 independently of one another are carbon atom or nitrogen atom, G is benzene ring, etc., L is -CH 2 -, -C(CH 3 )-, -CH(CN)-, etc., X is halogen atom, C 1 -C 6 haloalkyl, etc., Y ia halogen atm, C 1 -C 6 alkyl, etc., R 1 is -C(O)R 1a , -C(O)OR 1a , -C(O)NHR 1a , etc., R 2 is hydrogen atom, C 1 -C 6 haloalkyl, -C 1 -C 4 alkoxy C 1 -C 4 alkyl, cyano C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, -C(O)R 15 , -C(O)OR 15 , etc., R 3 is C 1 -C 6 haloalkyl, etc., m is an integer of 0 to 5, n is an integer of 0 to 4. The pesticide containing these compounds.

Description

Technical field [0001] The present invention relates to novel substituted isoxazoline compounds and salts thereof, and pest control agents characterized by containing the compounds as active ingredients. The pest control agent of the present invention refers to an agent for controlling internal or external parasites of mammals or birds that are domestic animals or pets in the fields of agriculture and horticulture or livestock and hygiene fields, or sanitary pests for household and work use, and unpleasant pests. A pest control agent that targets harmful arthropods such as Pest Control Agent). In addition, the pesticide of the present invention refers to insecticides and acaricides, nematicides, herbicides, fungicides, etc. in the agricultural and horticultural fields. Background technique [0002] As for the substituted isoxazoline compounds so far, it is known that 4-(5-substituted-5-substituted aryl-4,5-dihydroisoxazol-3-yl)benzamide compounds show activity against harmf...

Claims

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Application Information

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IPC IPC(8): C07D261/04C07D413/04C07D413/10C07D413/12C07D417/10A01N43/80A01P7/02A01P7/04C07C251/48
CPCC07D261/04C07D413/04C07D413/10C07D413/12C07D417/10C07C251/48A01N43/80A61P33/14
Inventor 三田猛志前田兼成菰田充阳
Owner NISSAN CHEM IND LTD
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