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Cyclopropyl-pyrazole derivative and application thereof in agriculture

A technology of cycloalkyl and alkyl, which is applied in the field of cyclopropyl-pyrazole derivatives and its preparation, can solve the problems of low selectivity, insufficient herbicidal effect, narrow spectrum of weed plants, etc., and achieve good control effect Effect

Active Publication Date: 2021-11-09
宁夏苏融达化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The active ingredients known from the documents cited above have disadvantages in use such as (a) no or only insufficient herbicidal action on weed plants, (b) excessive spectrum of weed plants to be controlled. Narrow or (c) too low selectivity in useful plant crops

Method used

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  • Cyclopropyl-pyrazole derivative and application thereof in agriculture
  • Cyclopropyl-pyrazole derivative and application thereof in agriculture
  • Cyclopropyl-pyrazole derivative and application thereof in agriculture

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0186] Example 1: Compound 3-(((5-chloro-3-(cyclopropyl)-1-ethyl-1H-pyrazol-4-yl)methyl)sulfonyl)-5,5-dimethyl Synthesis of -4,5-dihydroisoxazole

[0187]

[0188] Step 1: Synthesis of compound 5,5-dimethyl-4,5-dihydroisoxazol-3-ylisothiouronium hydrobromide

[0189] Thiourea (6 g, 79 mmol) was dissolved in acetonitrile (65 mL) at room temperature, hydrobromic acid (48%, 10 mL) was added dropwise, and stirred at room temperature for 1 h. 3-Chloro-5,5-dimethyl-4,5-dihydroisoxazole (12.6 g, 95 mmol) was added dropwise to the above mixed solution, and the temperature was raised to 40° C. and stirred overnight. The solvent was distilled off under pressure, and the obtained solid was recrystallized from ethyl acetate to obtain 19.2 g of white crystals, yield: 96.0%.

[0190] Step 2: Compounds 5-chloro-3-(cyclopropyl)-1-ethyl-1H-pyrazole-4-carbaldehyde and 3-chloro-5-(cyclopropyl)-1-ethyl-1H-pyridine Synthesis of azole-4-carbaldehyde

[0191]

[0192] Dissolve ethyl cyclop...

Embodiment 2

[0216] Example 2: Compound 3-(((3-chloro-5-(cyclopropyl)-1-ethyl-1H-pyrazol-4-yl)methyl)sulfonyl)-5,5-dimethyl Synthesis of -4,5-dihydroisoxazole

[0217]

[0218] Step 1: Synthesis of compound (3-chloro-5-(cyclopropyl)-1-ethyl-1H-pyrazol-4-yl)methanol

[0219]

[0220] Dissolve 3-chloro-5-(cyclopropyl)-1-ethyl-1H-pyrazole-4-carbaldehyde (0.80g, 4mmol) in anhydrous methanol (50mL) under ice bath, stir, add sodium borohydride (0.23g, 6.0mmol), raised to room temperature and stirred for 4h, removed methanol after the reaction, washed with water (50mL), extracted three times with ethyl acetate (50mL), combined the organic phases, and removed the solvent under reduced pressure to obtain colorless Liquid product 0.49g, yield: 61.0%.

[0221] MS-ESI:m / z 201.0[M+H] + .

[0222] Step 2: Synthesis of compound 4-(chloromethyl)-3-chloro-5-(cyclopropyl)-1-ethyl-1H-pyrazole

[0223]

[0224] (3-Chloro-5-(cyclopropyl)-1-ethyl-1H-pyrazol-4-yl)methanol (0.46g, 2.3mmol) was disso...

Embodiment 3

[0235] Example 3: Compound 3-(((5-(difluoromethoxy)-3-(cyclopropyl)-1-methyl-1H-pyrazol-4-yl)methyl)sulfonyl)-5 , Synthesis of 5-Dimethyl-4,5-dihydroisoxazole

[0236]

[0237] Step 1: Synthesis of compound 3-(cyclopropyl)-1-methyl-1H-pyrazol-5-ol

[0238]

[0239] Dissolve ethyl 3-cyclopropyl-3-oxopropionate (15.60g, 0.1mol) in absolute ethanol (100mL) under ice-cooling, stir, and slowly add 40% methylhydrazine aqueous solution (12.70g, 0.11 mol), the dropwise addition was completed, raised to room temperature and reacted for 4 hours, then raised to 80°C and reacted overnight. The ethanol was removed, washed with water (300 mL), extracted three times with ethyl acetate (150 mL), the organic phases were combined, and the solvent was removed under reduced pressure to obtain 12.70 g of a light yellow solid product with a yield of 92.0%.

[0240] MS-ESI: m / z 139.1[M+H] + .

[0241] Step 2: Synthesis of compound 5-(difluoromethoxy)-3-(cyclopropyl)-1-methyl-1H-pyrazole

...

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Abstract

The invention provides a cyclopropyl-pyrazole derivative and application thereof in agriculture. Specifically, the invention provides a compound as shown in a formula (Ia) or a stereoisomer, nitrogen oxide or salt of the compound as shown in the formula (Ia), a preparation method, a composition containing the compounds and application of the compounds in agriculture, especially application of the compounds as an active ingredient of a herbicide for preventing and treating unwanted plants. In the formulas, R1, R2, R3, R4, R5, R6, R7, n and Y have the meanings as described in the invention.

Description

technical field [0001] The present invention provides novel cyclopropyl-pyrazole derivatives and methods for their preparation; compositions containing these compounds and their use in agriculture. Background technique [0002] Pyrazole compounds are a class of compounds with excellent biological activity, and their herbicidal activity is reported in, for example, WO2002062770, WO 2003000686 and WO 2003010165. However, the compounds of the present invention described in detail hereinafter are not described in these documents. [0003] The active ingredients known from the documents cited above have disadvantages in use such as (a) no or only insufficient herbicidal action on weed plants, (b) excessive spectrum of weed plants to be controlled. Narrow or (c) too low selectivity in useful plant crops. [0004] Therefore, there is a need to provide chemically active ingredients which can be advantageously used as herbicides or plant growth regulators. Contents of the inventi...

Claims

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Application Information

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IPC IPC(8): C07D413/12A01N43/80A01P13/02
CPCC07D413/12A01N43/80
Inventor 李义涛林健曾水明吴双志伍阳池伟林
Owner 宁夏苏融达化工有限公司
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