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Amide derivative and pesticide containing such compound

A compound, C1-C4 technology, applied in the field of insecticides, can solve problems such as unrecorded insect activity

Active Publication Date: 2008-06-18
MITSUI CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the specification of U.S. Patent Publication No. 2002-032238 describes the medical use of a compound similar to the compound of the present invention, it does not describe the activity against insects at all.

Method used

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  • Amide derivative and pesticide containing such compound
  • Amide derivative and pesticide containing such compound
  • Amide derivative and pesticide containing such compound

Examples

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preparation example Construction

[0434] In the general formula shown in the following preparation method, Q 2 It represents the meaning described in [1] or general formula (2) or general formula (3).

[0435]

[0436] (In the formula, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 Indicates the same meaning as [1]. )

[0437]

[0438] (In the formula, Y 6 , Y 7 , Y 8 , Y 9Indicates the same meaning as [1]. )

[0439] Preparation method 1

[0440]

[0441] (In the formula, E represents -C(=G 1 )-Or-SO 2 -, A 1 , A 2 , A 3 , A 4 , G 1 , G 2 , R 1 , R 2 , X, n, Q 1 , Q 2 It has the same meaning as [1], and L represents a functional group having a leaving ability such as a halogen atom and a hydroxyl group. )

[0442] 1-(i): General formula (19) + General formula (20) → General formula (21)

[0443] The m-nitroaromatic carboxylic acid derivative having a leaving group represented by the general formula (19) and the aromatic amine derivative represented by the general formula (20) are reacted in a solvent or without a solvent, the...

Embodiment 1-1

[0829] Preparation of 5-amino-6-bromo-8-heptafluoroisopropylquinoline

[0830] Stir the solution of 1.21g 5-amino-8-heptafluoroisopropylquinoline in 5ml N,N-dimethylformamide under an ice-water bath, and then add dropwise the solution dissolved in 10ml N,N-dimethylformamide 0.69g N-bromosuccinimide. After stirring for 1 hour in an ice-water bath and 4 hours at room temperature, ethyl acetate and water were added to the reaction solution, and the organic phase was separated. It was washed twice with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1→4:1) to obtain 1.09 g (yield 72%) of the title compound as a light brown solid.

[0831] 1 H NMR(CDCl 3 )δ 4.98 (2H, broad-s), 7.43 (1H, dd, J=3.9, 8.3Hz), 8.08 (1H, d, J=1.0Hz), 8.13 (1H, dd, J=1.5, 8.3Hz) ), 8.91 (1H, dd, J=1.5, 3.9Hz).

Embodiment 1-2

[0833] Preparation of N-(6-bromo-8-heptafluoroisopropylquinolin-5-yl) 3-nitrobenzamide

[0834] 0.47 g of 3-nitrobenzoyl chloride and 1.5 g of 5-amino-6-bromo-8-heptafluoroisopropylquinoline were added to 5 ml of pyridine and stirred at room temperature. After 5 hours, ethyl acetate and 1N hydrochloric acid were added to the reaction solution, the organic phase was separated, washed twice with water, and washed three times with saturated sodium bicarbonate water. The solvent was distilled off under reduced pressure, and the obtained residue was dissolved in a mixed solvent of 8 ml of tetrahydrofuran and 2 ml of methanol. While stirring in an ice-water bath, 0.10 g of sodium hydroxide was added and stirred for 1 hour, and further stirred at room temperature for 4 hours. Ethyl acetate and water were added to the reaction solution, the organic phase was separated, and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residu...

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Abstract

The present invention provides a compound represented by the general formula (1) exhibiting a high insecticidal effect, and an insecticide containing the compound as an active ingredient. In the formula, A 1 、A 2 、A 3 、A 4 Indicates carbon atoms, etc., R 1 , R 2 Indicates a hydrogen atom, etc., G 1 , G 2 Represents an oxygen atom, etc., X represents a hydrogen atom, a halogen atom, etc., n represents an integer from 0 to 4, Q 1 Represents substituted phenyl, substituted heterocyclic group, etc., Q 2 Represents a substituted phenyl group, a substituted heterocyclic group, and the like.

Description

Technical field [0001] The present invention relates to a novel amide derivative and an insecticide containing the compound as an effective ingredient. Background technique [0002] Although the specifications of International Publication No. 2000 / 55120 and U.S. Patent No. 6,548,514 describe the medical use of compounds similar to the compounds of the present invention, they do not describe the activity against insects. It is obviously a compound outside the scope of the claims of the present invention. [0003] Although the specification of International Publication No. 2000 / 7980 describes the medical use of compounds similar to the compounds of the present invention, it does not describe the activity against insects at all. It is obviously a compound outside the scope of the claims of the present invention. [0004] Although the specification of U.S. Patent Publication No. 2002-032238 describes the medical use of compounds similar to the compounds of the present invention, it d...

Claims

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Application Information

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IPC IPC(8): C07C237/42A01N37/46A01N41/04A01N41/10A01N43/10A01N43/32A01N43/40A01N43/42A01N43/76A01N43/78A01P7/04C07C309/65C07C309/73C07C317/40C07D213/75C07D213/82C07D215/38C07D277/62
CPCA01N43/42C07C311/08C07D215/38A01N37/46C07C311/09C07C323/42A01N43/10A01N43/36A01N41/10C07C2102/08A01N43/40C07C237/42C07C255/57C07D213/82C07C2103/74A01N43/56C07D213/75C07C311/21A01N43/76C07C2102/42C07C317/40C07D277/62C07C309/73C07C311/11A01N43/78A01N41/04A01N43/32C07C309/65C07C2103/18C07C2602/08C07C2602/42C07C2603/18C07C2603/74C07D257/02
Inventor 甲斐章义肋田健夫胜田裕之吉田圭塚田英孝高桥祐介河原信行野村路一大同英则
Owner MITSUI CHEM INC
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