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4-(quinoline-4-methyl)piperidine amide compound and application thereof to plant nematodes diseases

A piperidine amide, plant nematode technology, applied in the application, nematicide, plant growth regulator and other directions, can solve the problems of ecological environment damage, high toxicity, long lasting effect and the like

Inactive Publication Date: 2018-05-29
田元强
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemical control is a routine control method in production. In the early 1990s, some highly toxic chemicals, such as aldicarb, became the first choice pesticides for controlling root-knot nematodes, and the dosage increased year by year. Due to its high toxicity (some are highly toxic) and It has a long duration in the soil, long-term use has caused root-knot nematodes to develop high drug resistance, and the ecological environment has been severely damaged. It is currently strictly prohibited to use on crops.

Method used

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  • 4-(quinoline-4-methyl)piperidine amide compound and application thereof to plant nematodes diseases
  • 4-(quinoline-4-methyl)piperidine amide compound and application thereof to plant nematodes diseases
  • 4-(quinoline-4-methyl)piperidine amide compound and application thereof to plant nematodes diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Synthesis of 2-((ethoxycarbonyl)amino)-4,4,4-trifluorobutyric acid

[0022]

[0023] 2-Amino-4,4,4-trifluorobutanoic acid (1.2 g, 7.64 mmol) was dissolved in anhydrous CH 2 Cl 2 (15 mL) was cooled in an ice bath. Ethyl chloroformate (0.80 mL, 8.40 mmol) was added and the reaction was stirred at 0 °C for 10 minutes. After this time, the reaction was allowed to warm to room temperature and stirring was continued for 2 hours. Evaporate the solvent, add 50ml of NaHCO with a mass fraction of 5% in the reactant 3 The solution was stirred for five minutes, and then 50ml of CH was added to the system 2 Cl 2 Stir for five minutes, separate the layers, and wash the aqueous layer with 50 mL of CH 2 Cl 2 were extracted twice, and then the combined organic layers were washed with anhydrous MgSO 4 The crystals were dried and concentrated to obtain 2-((ethoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid as a white solid, yield 1.69 g, 7.40 mmol, yield 96.8%. 1 H-...

Embodiment 2

[0024] Example 2: Synthesis of (1-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-1-oxobutane-2-yl)carbamate tert-butyl ester

[0025]

[0026] 2-((ethoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid (1.3g, 5.67mmol) obtained in Example 1, 4-(bromomethyl)piperidine (0.75g, 4.21 mmole), HOAT (0.74 g, 5.47 mmole), EDCI (1.05 g, 5.47 mmole) and triethylamine (1.4 mL, 10 mmole) were dissolved in DMF (30 mL) and stirred at room temperature overnight. All volatiles were distilled off under high vacuum, and the residue was dissolved in a 4:1 chloroform / isopropanol mixture solvent. The organic solution was washed twice with brine and washed with anhydrous MgSO 4 Dry and concentrate in vacuo. flash chromatography on silica gel (SiO 2 , DCM:MeOH:10% ammonia solution=80:10:10) to give white solid (1-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-1 -Oxobutan-2-yl) tert-butyl carbamate, 1.29 g, 92% yield. 1 H-NMR (400MHz, CDCl3) δ: 1.04(t, 3H), 1.51(m, 2H), 1.79-2.08(m, 3H), 2.67(m...

Embodiment 3

[0027] Example 3: Synthesis of 1-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-2-(methylamino)butan-1-one

[0028]

[0029] At room temperature, under nitrogen atmosphere, to LiAlH 4 (1.2g, 31.62mmol) in tetrahydrofuran solution was added 1-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-1-oxobutan-2-yl) A solution of tert-butyl carbamate (1.1 g, 2.83 mmol) in tetrahydrofuran (50 mL). The resulting solution was heated to reflux overnight in an oil bath. The reaction was then quenched by adding 200 mL of ice water. The solid was filtered off. The filtrate was extracted with 2 x 200 mL ethyl acetate. The combined organic layers were washed with Na 2 SO 4 Dry and concentrate in vacuo. Apply the residue to Al 2 o 3On column and eluted sequentially with EtOAc / petroleum ether (5:1), DCM / MeOH (80:1-20:1) to give 1-(4-(bromomethyl)piperidin-1-yl) as a yellow solid -4,4,4-Trifluoro-2-(methylamino)butan-1-one, 0.89 g, yield 95%. 1 H-NMR(400 MHz, CDCl3)δ:1.39-1.51(m,3H),1...

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Abstract

The invention discloses a 4-(quinoline-4-methyl)piperidine amide compound, which has a structural formula shown in the description. The inhibition rate of the compound on the meloidogyne incognita eggincubation is 65.88; the insecticidal activity is realized on meloidogyne incognita second stage juveniles, cereal cyst nematode and heterodera glycines; the LD90 is respectively 67.5mu g / mL, 53.4mug / mL and 98.7mu g / mL. The poisoning and killing capability on the cereal cyst nematode is more obvious. The compound provided by the invention can be used for preventing and treating the plant nematode diseases.

Description

technical field [0001] The invention belongs to the field of prevention and control of agricultural diseases and insect pests, and in particular relates to a 4-(quinoline-4-methyl)piperidine amide compound and its application in the prevention and treatment of plant nematode diseases. technical background [0002] Root-knot nematode Meloidogyne spp. is the most diverse, most widely distributed, and most serious nematode among plant pathogenic nematodes. The nematode overwinters in soil, diseased plants, and organic residues. The nematode not only directly damages the roots and stems of plants, but also induces and aggravates the occurrence of other soil-borne pathogens, such as Fusatium oxysporum, Verticillium dahliae and Rhizoctonia solani, etc. With the adjustment of my country's industrial structure, the planting area of ​​crops in protected areas has increased year by year, and the suitable temperature and humidity in protected areas have created good environmental condi...

Claims

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Application Information

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IPC IPC(8): C07D215/12A01N43/42A01P5/00
CPCC07D215/12A01N43/42
Inventor 田元强
Owner 田元强
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