Substituted isoxazoline compound and pest control agent

An isoxazoline and compound technology, which is applied in the field of pest control agents and can solve problems such as unknown usefulness of pest control agents

Active Publication Date: 2013-04-10
NISSAN CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, regarding the specific N-[4-(5-substituted-5-substituted aryl-4,5-dihydroisoxazol-3-yl)phenylmethyl]sulfur-containing alkylamide compound involved in the present invention etc. without any disclosure, and in turn, its usefulness as a pest control agent is 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

[0610] Hereinafter, the present invention will be described in more detail by specifically describing 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

[0613] N-[2-Chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl]methanol -2-(methylthio)acetamide (Compound No. 1-005 of the present invention).

[0614] Step 1: Production of 3-chloro-4-methylbenzaldehyde oxime

[0615] To a solution of 5.0 g of 3-chloro-4-methylbenzaldehyde in 40 ml of methanol and 30 ml of water was added 4.7 g of hydroxylamine hydrochloride, followed by stirring at room temperature for 2 hours. After the reaction was finished, the reaction mixture was diluted with 70ml of ethyl acetate and washed with water (30ml×1), dehydrated and dried with saturated brine and anhydrous sodium sulfate successively, and the solvent was distilled off under reduced pressure to obtain the target product as white crystals. Compound 5.1g. The target product was directly used in the next step without further purification.

[0616] Melting point 66.0~68.0℃

[0617] 1 H NMR (CDCl 3 , Me 4 Si, 300MHz) δ8.12(bs, 1H), 8.07(s, 1H), 7.56(s, 1H)...

Synthetic example 2

[0633] N-[1-[4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl ]ethyl]-2-(methylthio)acetamide (Compound No. 1-001 of the present invention).

[0634] Step 1: Production of 5-[3,5-bis(trifluoromethyl)phenyl]-3-(4-ethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

[0635] To a solution of 1.49 g of 4-ethylbenzaldoxime in 10 ml of N,N-dimethylformamide was added 1.60 g of N-chlorosuccinimide, followed by stirring at room temperature for 2 hours. Next, 3.00 g of 3,5-bis(trifluoromethyl)-1-(1-trifluoromethylvinyl)benzene and 3.00 g of potassium bicarbonate were added to the reaction mixture, and stirring was continued at room temperature for 14 hours. . After the reaction was completed, 10 ml of water was added to the reaction mixture and extracted with ethyl acetate (50 ml × 1), the organic layer was washed with 20 ml of water, then dehydrated with saturated brine, anhydrous sodium sulfate, dried, and distilled under reduced pressure. So...

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Abstract

There is provided a novel pest control agent, particularly an insecticide or miticide. A substituted isoxazoline compound of General Formula (1): where A 1 , A 2 and A 3 independently are CH or N, etc., X 1 , X 2 and X 3 are independently are H, a halogen atom, etc., Y 1 is H, etc., R 1 is -C(O)R 1a , -C(S)R 1a , R 1a is -C(R 9 )(R 9a )-S(O) r R 10 , -C(R 9 )(R 9a )-S(O) t (R 10 )=NR 11 , etc., R 2 is H, etc., R 3 is CF 3 , CClF 2 , etc., R 4 is H, etc., R 9 is H, etc., R 9a is H, etc., R 10 is C 1-2 alkyl, etc., R 11 is H, etc., r is an integer of 0-2, t is an integer of 0 or 1; and a pest control agent comprising the compound or the salt thereof.

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 in the present invention refers to internal or external parasites of mammals or birds used in the agricultural and horticultural fields or the livestock and sanitation fields (livestock and / or pets), and / or sanitary pests in homes and workplaces. , unpleasant pests) and other harmful arthropods. In addition, the pesticide in the present invention refers to insecticides, acaricides, nematicides, herbicides, fungicides, etc. in the agricultural and horticultural fields. Background technique [0002] Conventionally, as a substituted isoxazoline compound, a 4-(5-substituted-5-substituted aryl-4,5-dihydroisoxazol-3-yl)benzamide compound has been known (refer to Patent Document 1 and 2) and N-[4-(5-substituted-5-substituted aryl-4,5-dihydroisoxazol-3-yl)ph...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D261/04A01N43/80A01P7/02A01P7/04A61K31/42A61K31/422A61K31/506A61P33/00A61P33/14C07D413/04C07D413/10C07D413/12
CPCC07D261/04C07D413/10C07D413/04C07D413/12A01N43/80A61P33/00A61P33/14
Inventor 三田猛志前田兼成山田阳子池田荣达外山贤一菰田充阳
Owner NISSAN CHEM CORP
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