Pyrazole derivative and harmful organism-controlling agent

A technology of pyrazole derivatives and alkyl groups, applied in biocides, animal repellents, plant growth regulators, etc., can solve the problems of unrecorded pest control activity and unrevealed carboxylic acid amides

Active Publication Date: 2021-01-15
KUMIAI CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Although Patent Document 1 describes a pyrazole derivative having a pest control effect, it does not specifically disclose a compound having a carboxylic acid amide at the 3-position of the pyrazole ring.
[0003] Although Non-Patent Document 1 describes a pyrazole derivative in which the phenyl group is substituted at the 4-position of the pyrazole ring, its pest control activity is not described.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[1059]Production of 1-(pyridin-3-yl)-4-[2-(trifluoromethyl)phenyl]-1H-pyrazole-3-carboxamide (the compound number of the present invention: A-0044)

[1060]1) 4-{[(Nafluorobutyl)sulfonyl]oxy}-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid ethyl ester (the compound number of the present invention: D-0008)

[1061]4-hydroxy-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid ethyl ester (15.0g, 64.3mmol) synthesized by the methods described in Reference Examples 1 and 2 of WO 2016 / 027790A , Triethylamine (13.0 g, 128.5 mmol) and nonafluorobutanesulfonic acid fluoride (27.2 g, 90.0 mmol) were sequentially added to dichloromethane (300 mL) under ice cooling, and stirred at room temperature overnight. The reaction solution was poured into saturated brine, and extracted with dichloromethane. After drying the obtained organic layer with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was washed with diisopropyl ether to obtain 4-{[(nonafluorobutyl)sulfon...

Embodiment 2

[1073]Production of 4-(4-methylpyridin-3-yl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxamide (the compound number of the present invention: B-100)

[1074]1) 4-(4-Methylpyridin-3-yl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid ethyl ester (the compound number of the present invention: D-0108)

[1075]The 4-{[(nonafluorobutyl)sulfonyl]oxy}-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid ethyl ester (3.4g, 6.6mmol), 4-( Methylpyridin-3-yl)boronic acid (1.0g, 7.3mmol), sodium carbonate (1.6g, 15.1mmol) and tetrakis (triphenylphosphine) palladium (0.38g, 0.33mmol) are added to 1,2-dimethyl In a mixed solvent of oxyethane (30 mL) and water (6 mL), the mixture was heated to reflux for 9 hours under a nitrogen atmosphere. After the reaction, the reaction solution was poured into saturated brine and extracted with ethyl acetate. After drying the obtained organic layer with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column...

Embodiment 3

[1087]Production of 4-(4-chloro-2-methoxyphenyl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxamide (the compound number of the present invention: A-0634)

[1088]1) 4-(4-Chloro-2-methoxyphenyl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid ethyl ester (the compound number of the present invention: C-0634)

[1089]The 4-{[(nonafluorobutyl)sulfonyl]oxy}-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid ethyl ester (0.42g, 0.82mmol), 4-chloro -2-Methoxyphenylboronic acid (0.20g, 1.1mmol), sodium carbonate (0.19g, 1.8mmol) and tetrakis (triphenylphosphine) palladium (0.050g, 0.043mmol) were added to tetrahydrofuran (5.0mL) and water (0.50 mL) in a mixed solvent and heated to reflux for 3 hours under a nitrogen atmosphere. After the reaction, the reaction solution was poured into saturated brine and extracted with ethyl acetate. After drying the obtained organic layer with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column ch...

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Abstract

The present invention provides a harmful organism-controlling agent having excellent safety, controlling effect, residual efficacy, etc. Provided are: a pyrazole derivative represented by general formula [1][wherein p represents an integer of 0 or 1, R1, R2, R3, R4 and R5 represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, and the like, A represents an oxygen atom or a sulfur atom, Q represents a halogen atom, an unsubstituted or (R8)m-substituted C6-C10 aryl group, and the like, and R6 and R7 represent a hydrogen atom, a C1-C6 alkyl group, and the like], or an agriculturally acceptable salt thereof; and a harmful organism-controlling agent comprising the pyrazole derivative as an active ingredient.

Description

Technical field[0001]The present invention relates to a novel pyrazole derivative or an agriculturally acceptable salt thereof, and a pest control agent containing the derivative as an active ingredient.Background technique[0002]Although Patent Document 1 describes a pyrazole derivative having a pest control effect, it does not specifically disclose a compound having a carboxylic acid amide at the 3-position of the pyrazole ring.[0003]Although Non-Patent Document 1 describes a pyrazole derivative in which the phenyl group is substituted at the 4-position of the pyrazole ring, it does not describe its pest control activity.[0004][Patent Document 1] WO 2012 / 102387 A[0005][Non-Patent Document 1] International Journal of Chem Tech Research, 2013, Volume 5, Issue 1, Pages 80-84Summary of the invention[0006]Problems to be solved by the invention[0007]The pest control agent used for useful crops needs to be an agent that can exhibit a sufficient pest control effect with a low dose when app...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A01N43/56A01N47/02A01P7/04A61K31/4439A61P33/14C07D401/14C07D409/14
CPCA01N43/56A61P33/14C07D401/14C07D401/04C07D409/14C07D405/14C07D417/14C07D413/14A01N47/04A01N43/78A01N43/76A01N43/80A01N43/66A01N43/707A01N47/02A61K31/4439A01N25/04A01N25/14A01N25/30
Inventor 石川谅金原明鸟谷部启二渡部彬中谷昌央高根泽阳松田武
Owner KUMIAI CHEM IND CO LTD
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