Amide derivatives, process for production of the same, and method for application thereof as insecticide

Abstract

The purpose of the present invention is to provide a kind of high-efficiency insecticide. A compound represented by the general formula (1), an insecticide using the compound as an active ingredient, and a preparation method thereof, wherein, A 1 、A 2 、A 3 、A 4 represent carbon atom, nitrogen atom or oxidized nitrogen atom respectively, R 1 , R 2 Respectively represent a hydrogen atom, an alkyl group that may be substituted, etc., G 1 , G 2 represent oxygen atom or sulfur atom respectively, X is the same or different, represent hydrogen atom, halogen atom, C1-C3 alkyl group, trifluoromethyl group, n represents an integer from 0 to 4, Q 1 Represents a phenyl group that may be substituted, a heterocyclic group that may be substituted, etc., Q 2 represents a phenyl group or a heterocyclic group having one or more substituents, and at least one of the substituents represents a C1-C4 haloalkoxy group or the like.

Description

Technical field

[0001] The present invention relates to a compound represented by the general formula (1), an insecticide containing the compound as an active ingredient, and a method for preparing and using the compound.

[0002]

[0003] (In the formula, A 1 , A 2 , A 3 , A 4 Respectively represent carbon atom, nitrogen atom or oxidized nitrogen atom, R 1 , R 2 Respectively represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted C1-C4 alkylcarbonyl group, G 1 , G 2 Each represents an oxygen atom or a sulfur atom, X is the same or different, represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a trifluoromethyl group, n represents an integer from 0 to 4, and Q 1 , Q 2 Represents an optionally substituted phenyl group, an optionally substituted naphthyl group, and an optionally substituted heterocyclic group. ) Background technique

[0004] In International Publication No. 2000 / 55120 and U.S. Patent No. 6,548,514, compounds simila...

Examples

Embodiment 1-1

[0574] Preparation of N-(2,6-Dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide

[0575] Add 20.0g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 11.0g of pyridine to 100ml of tetrahydrofuran, stir at room temperature to make a solution, and slowly drop 3 dissolved in 20ml of tetrahydrofuran into the solution. -Nitrobenzoyl chloride 13.0g. After stirring for 10 hours at room temperature, ethyl acetate and water were added to the reaction solution. After the liquid separation operation, the organic layer was separated and dried with anhydrous magnesium sulfate. The above solution was filtered, the filtrate was collected, and the residue obtained by distilling off the solvent under reduced pressure was washed with a hexane-diisopropyl ether mixed solvent to obtain 26.0 g (yield 85%) of a white solid of the target product.

[0576] 1 H-NMR(CDCl 3 , Ppm) δ 2.33 (6H, s), 7.37 (2H, s), 7.68 (1H, s), 7.72 (1H, t, J = 8.1 Hz), 8.28 (1H, d, J = 8.1 Hz), 8.44 (1H, dd, J = 1.2, 8.1 H...

Embodiment 1-2

[0578] Preparation of N-(2,6-Dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide (Compound No. I-2)

[0579] Add 0.90 g of N-(2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-nitrobenzamide and 1.56 g of stannous chloride anhydride to 25 ml of ethanol, and at room temperature Stir to make a solution, add 2ml of concentrated hydrochloric acid to the solution, and stir at 60°C for 1 hour. After returning to room temperature, the reaction solution was poured into water, and potassium carbonate was used for neutralization. After adding ethyl acetate and removing insoluble matter by filtration, the organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, the filtrate was collected, and the residue obtained by distilling off the solvent under reduced pressure was washed with hexane to obtain 0.44 g (yield 53%) of a white solid of the target product.

[0580] 1 H-NMR(CDCl 3 , Ppm) δ 2.34 (6H, s), 3.87 (2H, broad), 6.86-6.89 (1H, m), 7.20-7.35 (6...

Embodiment 1-3

[0582] Preparation of N-(2,6-Dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzoylamino)benzamide (Compound No. 10)

[0583] Add 0.25 g of N-(2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-aminobenzamide and 0.06 g of pyridine to 5 ml of tetrahydrofuran and stir at room temperature to make a solution. 0.09 g of benzoyl chloride dissolved in 1 ml of tetrahydrofuran was added dropwise. After stirring for 1 hour at room temperature, ethyl acetate and 1N hydrochloric acid were added, the organic layer was separated, and the organic layer was washed once with a saturated sodium bicarbonate aqueous solution, and dried with anhydrous magnesium sulfate. The above solution was filtered, the filtrate was collected, and the solid precipitated by distilling off the solvent under reduced pressure was washed with diisopropyl ether to obtain 0.29 g (yield: 92%) of a white solid of the target product.

[0584] 1 H-NMR(DMSO-d 6 , Ppm) δ 2.37 (6H, s), 7.34 (2H, s), 7.46-7.57 (4H, m), 7.75 (1H, d, J=7.8 ...

Technical field

[0001] The present invention relates to a compound represented by the general formula (1), an insecticide containing the compound as an active ingredient, and a method for preparing and using the compound.

[0002]

[0003] (In the formula, A 1 , A 2 , A 3 , A 4 Respectively represent carbon atom, nitrogen atom or oxidized nitrogen atom, R 1 , R 2 Respectively represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted C1-C4 alkylcarbonyl group, G 1 , G 2 Each represents an oxygen atom or a sulfur atom, X is the same or different, represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a trifluoromethyl group, n represents an integer from 0 to 4, and Q 1 , Q 2 Represents an optionally substituted phenyl group, an optionally substituted naphthyl group, and an optionally substituted heterocyclic group. ) Background technique

[0004] In International Publication No. 2000 / 55120 and U.S. Patent No. 6,548,514, compounds simila...

Examples

Embodiment 1-1

[0574] Preparation of N-(2,6-Dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide

[0575] Add 20.0g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 11.0g of pyridine to 100ml of tetrahydrofuran, stir at room temperature to make a solution, and slowly drop 3 dissolved in 20ml of tetrahydrofuran into the solution. -Nitrobenzoyl chloride 13.0g. After stirring for 10 hours at room temperature, ethyl acetate and water were added to the reaction solution. After the liquid separation operation, the organic layer was separated and dried with anhydrous magnesium sulfate. The above solution was filtered, the filtrate was collected, and the residue obtained by distilling off the solvent under reduced pressure was washed with a hexane-diisopropyl ether mixed solvent to obtain 26.0 g (yield 85%) of a white solid of the target product.

[0576] 1 H-NMR(CDCl 3 , Ppm) δ 2.33 (6H, s), 7.37 (2H, s), 7.68 (1H, s), 7.72 (1H, t, J = 8.1 Hz), 8.28 (1H, d, J = 8.1 Hz), 8.44 (1H, dd, J = 1.2, 8.1 H...

Embodiment 1-2

[0578] Preparation of N-(2,6-Dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide (Compound No. I-2)

[0579] Add 0.90 g of N-(2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-nitrobenzamide and 1.56 g of stannous chloride anhydride to 25 ml of ethanol, and at room temperature Stir to make a solution, add 2ml of concentrated hydrochloric acid to the solution, and stir at 60°C for 1 hour. After returning to room temperature, the reaction solution was poured into water, and potassium carbonate was used for neutralization. After adding ethyl acetate and removing insoluble matter by filtration, the organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, the filtrate was collected, and the residue obtained by distilling off the solvent under reduced pressure was washed with hexane to obtain 0.44 g (yield 53%) of a white solid of the target product.

[0580] 1 H-NMR(CDCl 3 , Ppm) δ 2.34 (6H, s), 3.87 (2H, broad), 6.86-6.89 (1H, m), 7.20-7.35 (6...

Embodiment 1-3

[0582] Preparation of N-(2,6-Dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzoylamino)benzamide (Compound No. 10)

[0583] Add 0.25 g of N-(2,6-dimethyl-4-heptafluoroisopropyl) phenyl 3-aminobenzamide and 0.06 g of pyridine to 5 ml of tetrahydrofuran and stir at room temperature to make a solution. 0.09 g of benzoyl chloride dissolved in 1 ml of tetrahydrofuran was added dropwise. After stirring for 1 hour at room temperature, ethyl acetate and 1N hydrochloric acid were added, the organic layer was separated, and the organic layer was washed once with a saturated sodium bicarbonate aqueous solution, and dried with anhydrous magnesium sulfate. The above solution was filtered, the filtrate was collected, and the solid precipitated by distilling off the solvent under reduced pressure was washed with diisopropyl ether to obtain 0.29 g (yield: 92%) of a white solid of the target product.

[0584] 1 H-NMR(DMSO-d 6 , Ppm) δ 2.37 (6H, s), 7.34 (2H, s), 7.46-7.57 (4H, m), 7.75 (1H, d, J=7.8 ...

Images